NCBI Taxonomy: 169642

Scopoletin

C10H8O4 (192.0423)

Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

Geniposide

C17H24O10 (388.1369)

Geniposide is a terpene glycoside. Geniposide is a natural product found in Feretia apodanthera, Gardenia jasminoides, and other organisms with data available. See also: Gardenia jasminoides whole (part of). Origin: Plant; SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids Annotation level-1 Geniposide is an iridoid glucoside extracted from Gardenia jasminoidesEllis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities. Geniposide is an iridoid glucoside extracted from Gardenia jasminoidesEllis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities.

Vanillic acid

C8H8O4 (168.0423)

Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity (PMID: 16899266). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity. (PMID: 16899266). Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate. Vanillic acid is a natural product found in Ficus septica, Haplophyllum cappadocicum, and other organisms with data available. Vanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. Vanillic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=121-34-6 (retrieved 2024-06-29) (CAS RN: 121-34-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

Protocatechuic acid

C7H6O4 (154.0266)

Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

Scoparone

C11H10O4 (206.0579)

Scoparone is a member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities. It has a role as a plant metabolite, an anti-inflammatory agent, an antilipemic drug, an immunosuppressive agent, an antihypertensive agent and an anti-allergic agent. It is a member of coumarins and an aromatic ether. It is functionally related to an esculetin. Scoparone is a natural product found in Haplophyllum ramosissimum, Haplophyllum thesioides, and other organisms with data available. A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities. D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics Scoparone is found in anise. Scoparone is found in several citrus oil D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents Found in several citrus oils Scoparone is isolated from Artemisia capillaris Thunb., has anticoagulant, vasorelaxant antioxidant, anti-inflammatory activities[1]. Scoparone is isolated from Artemisia capillaris Thunb., has anticoagulant, vasorelaxant antioxidant, anti-inflammatory activities[1].

Ursolic acid

C30H48O3 (456.3603)

Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Chlorogenic acid

C16H18O9 (354.0951)

Chlorogenic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. It is functionally related to a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate. Chlorogenic Acid has been used in trials studying the treatment of Advanced Cancer and Impaired Glucose Tolerance. Chlorogenic Acid is a natural product found in Pavetta indica, Fragaria nipponica, and other organisms with data available. Chlorogenic Acid is a polyphenol and the ester of caffeic acid and quinic acid that is found in coffee and black tea, with potential antioxidant and chemopreventive activities. Chlorogenic acid scavenges free radicals, which inhibits DNA damage and may protect against the induction of carcinogenesis. In addition, this agent may upregulate the expression of genes involved in the activation of the immune system and enhances activation and proliferation of cytotoxic T-lymphocytes, macrophages, and natural killer cells. Chlorogenic acid also inhibits the activity of matrix metalloproteinases. A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68). See also: Arctium lappa Root (part of); Cynara scolymus leaf (part of); Lonicera japonica flower (part of) ... View More ... Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinsons disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID:16507475, 17368041). A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. [Raw Data] CBA08_Chlorogenic-aci_pos_10eV_1-1_01_209.txt [Raw Data] CBA08_Chlorogenic-aci_neg_30eV_1-1_01_218.txt [Raw Data] CBA08_Chlorogenic-aci_neg_20eV_1-1_01_217.txt [Raw Data] CBA08_Chlorogenic-aci_pos_30eV_1-1_01_211.txt [Raw Data] CBA08_Chlorogenic-aci_neg_40eV_1-1_01_219.txt [Raw Data] CBA08_Chlorogenic-aci_pos_20eV_1-1_01_210.txt [Raw Data] CBA08_Chlorogenic-aci_pos_50eV_1-1_01_213.txt [Raw Data] CBA08_Chlorogenic-aci_neg_50eV_1-1_01_220.txt [Raw Data] CBA08_Chlorogenic-aci_neg_10eV_1-1_01_216.txt [Raw Data] CBA08_Chlorogenic-aci_pos_40eV_1-1_01_212.txt Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

Caffeic acid

C9H8O4 (180.0423)

Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Salicin

C13H18O7 (286.1052)

Salicin, also known as salicoside or delta-salicin, is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It derives from a salicyl alcohol. Salicin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Salicin exists in all living organisms, ranging from bacteria to humans. Salicin is a bitter tasting compound. Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a prodrug, an antipyretic, a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is an aryl beta-D-glucoside, an aromatic primary alcohol and a member of benzyl alcohols. It is functionally related to a salicyl alcohol. Salicin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Salicin is a natural product found in Salix candida, Populus tremula, and other organisms with data available. Salicin is an alcoholic β-glycoside that contains D-glucose. Salicin is an anti-inflammatory agent that is produced from willow bark. Salicin is closely related in chemical make-up to aspirin and has a very similar action in the human body. When consumed by humans, Salicin is metabolized into salicylic acid. [HMDB] An aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D004791 - Enzyme Inhibitors Salicin is a natural COX inhibitor. Salicin is a natural COX inhibitor.

Ferulic acid

C10H10O4 (194.0579)

trans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID:17127365, 1398220, 15453708, 9878519). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID:8395165). Ferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. It has a role as an antioxidant, a MALDI matrix material, a plant metabolite, an anti-inflammatory agent, an apoptosis inhibitor and a cardioprotective agent. It is a conjugate acid of a ferulate. Ferulic acid is a natural product found in Haplophyllum griffithianum, Visnea mocanera, and other organisms with data available. Ferulic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Angelica sinensis root (part of). Widely distributed in plants, first isolated from Ferula foetida (asafoetida). Antioxidant used to inhibit oxidn. of fats, pastry products, etc. Antifungal agent used to prevent fruit spoilage. trans-Ferulic acid is found in many foods, some of which are deerberry, peach, shea tree, and common bean. A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D002491 - Central Nervous System Agents > D000700 - Analgesics D000975 - Antioxidants > D016166 - Free Radical Scavengers D006401 - Hematologic Agents > D000925 - Anticoagulants D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H074 (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

Benzoic acid

C7H6O2 (122.0368)

Benzoic acid appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate. A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21\\\\\% compared to placebo. Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. See also: Salicylic Acid (active moiety of); Benzoyl Peroxide (active moiety of); Sodium Benzoate (active moiety of) ... View More ... Widespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). It can be found in Serratia (PMID:23061754). Benzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=65-85-0 (retrieved 2024-06-28) (CAS RN: 65-85-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

Scopolin

C16H18O9 (354.0951)

Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a monosaccharide derivative, a member of coumarins and a beta-D-glucoside. It is functionally related to a scopoletin. Scopolin is a natural product found in Artemisia ordosica, Astragalus onobrychis, and other organisms with data available. See also: Chamaemelum nobile flower (part of). A member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

DL-Mannitol

C6H14O6 (182.079)

D-mannitol appears as odorless white crystalline powder or free-flowing granules. Sweet taste. (NTP, 1992) D-mannitol is the D-enantiomer of mannitol. It has a role as an osmotic diuretic, a sweetening agent, an antiglaucoma drug, a metabolite, an allergen, a hapten, a food bulking agent, a food anticaking agent, a food humectant, a food stabiliser, a food thickening agent, an Escherichia coli metabolite and a member of compatible osmolytes. Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid. On October 30, 2020, mannitol was approved by the FDA as add-on maintenance therapy for the control of pulmonary symptoms associated with cystic fibrosis in adult patients and is currently marketed for this indication under the name BRONCHITOL® by Chiesi USA Inc. Mannitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Mannitol is an Osmotic Diuretic. The mechanism of action of mannitol is as an Osmotic Activity. The physiologic effect of mannitol is by means of Increased Diuresis. Mannitol is a natural product found in Pavetta indica, Scoparia dulcis, and other organisms with data available. Mannitol is a naturally occurring alcohol found in fruits and vegetables and used as an osmotic diuretic. Mannitol is freely filtered by the glomerulus and poorly reabsorbed from the renal tubule, thereby causing an increase in osmolarity of the glomerular filtrate. An increase in osmolarity limits tubular reabsorption of water and inhibits the renal tubular reabsorption of sodium, chloride, and other solutes, thereby promoting diuresis. In addition, mannitol elevates blood plasma osmolarity, resulting in enhanced flow of water from tissues into interstitial fluid and plasma. D-mannitol is a metabolite found in or produced by Saccharomyces cerevisiae. A diuretic and renal diagnostic aid related to sorbitol. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. See also: Mannitol; sorbitol (component of); Mannitol; menthol (component of). Mannitol, or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6), is an alcohol and a sugar (sugar alcohol), or a polyol, it is a stereoisomer of sorbitol and is similar to the C5 xylitol. The structure of mannitol is made of a straight chain of six carbon atoms, each of which is substituted with a hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, it is produced by a wide range of organisms such as bacteria, fungi and plants (PMID: 19578847). In medicine, mannitol is used as a diuretic and renal diagnostic aid. Mannitol has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a weak base, such as sodium bicarbonate, to the solution to adjust its pH. Mannitol is a non-permeating molecule i.e., it cannot cross biological membranes. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. Mannitol is found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312; PMID: 29480337). Mannitol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=85085-15-0 (retrieved 2024-07-01) (CAS RN: 69-65-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity.

Quercetin

C15H10O7 (302.0427)

Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Pinoresinol

C20H22O6 (358.1416)

Epipinoresinol is an enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. It has a role as a plant metabolite and a marine metabolite. Epipinoresinol is a natural product found in Pandanus utilis, Abeliophyllum distichum, and other organisms with data available. An enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. (+)-pinoresinol is an enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. It has a role as a hypoglycemic agent, a plant metabolite and a phytoestrogen. Pinoresinol is a natural product found in Pandanus utilis, Zanthoxylum beecheyanum, and other organisms with data available. See also: Acai fruit pulp (part of). An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.907 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.905 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.897 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.895 Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Genipin

C11H14O5 (226.0841)

Genipin is found in beverages. Genipin is a constituent of Genipa americana (genipap) Genipin is an aglycone derived from an iridoid glycoside called geniposide present in fruit of Gardenia jasminoides. Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with LD50 i.v. 382 mg/kg in mice, therefore, much less toxic than glutaraldehyde and many other commonly used synthetic cross-linking regents. It is also used for pharmaceutical purposes, such as choleretic action for liver diseases control Genipin is an iridoid monoterpenoid. It has a role as an uncoupling protein inhibitor, a hepatotoxic agent, an apoptosis inhibitor, an antioxidant, an anti-inflammatory agent and a cross-linking reagent. Genipin is a natural product found in Gardenia jasminoides, Rothmannia globosa, and other organisms with data available. D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics Constituent of Genipa americana (genipap) Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2]. Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2]. Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2].

Palmitic acid

C16H32O2 (256.2402)

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Campesterol

C28H48O (400.3705)

Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Lupeol

C30H50O (426.3861)

Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

Betulinic acid

C30H48O3 (456.3603)

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

Oleanolic acid

C30H48O3 (456.3603)

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

Crocin

C44H64O24 (976.3787)

Crocin is a water-soluble carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. Crocin suppresses tumor necrosis factor (TNF)alpha-induced apoptosis of pheochromocytoma (PC12) cells by modulating mRNA expressions of Bcl-2 family proteins, which trigger downstream signals culminating in caspase-3 activation followed by cell death. Depriving cultured PC12 cells of serum/glucose causes a rapid increase in cellular ceramide levels, followed by an increase in the risk of cell death. The accumulation of ceramide was found to depend on the activation of neutral sphingomyelinase (nSMase). Crocin prevented the activation of nSMase by enhancing the transcription of gamma-glutamylcysteinyl synthase, which contributes to a stable glutathione supply that blocks the activity of nSMase. (PMID: 17215084). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211). Crocin-1 is a diester that is crocetin in which both of the carboxy groups have been converted to their gentiobiosyl esters. It is one of the water-soluble yellow-red pigments of saffron and is used as a spice for flavouring and colouring food. Note that in India, the term Crocin is also used by GlaxoSmithKline as a brand-name for paracetamol. It has a role as an antioxidant, a food colouring, a plant metabolite and a histological dye. It is a diester, a disaccharide derivative and a diterpenoid. It is functionally related to a beta-D-gentiobiosyl crocetin and a gentiobiose. Crocin has been investigated for the treatment of Hyperglycemia, Metabolic Syndrome, Hypertriglyceridemia, and Hypercholesterolemia. Crocin is a natural product found in Gardenia jasminoides, Calycanthus, and other organisms with data available. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids The colouring principle of saffron Crocin (Crocin I) is a nutraceutical and the main constituent isolated from the stigmas of Crocus sativus with immense pharmacological properties as anti-inflammatory, anticancer, antidepressant and anticonvulsant[1]. Crocin (Crocin I) is a nutraceutical and the main constituent isolated from the stigmas of Crocus sativus with immense pharmacological properties as anti-inflammatory, anticancer, antidepressant and anticonvulsant[1].

Tricrocin

C38H54O19 (814.3259)

Tricrocin is a water soluble crocetin glycoside, a carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. (PMID: 17215084). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211). Beta-D-gentiobiosyl beta-D-glucosyl crocetin is a diester resulting from the formal condensation of the carboxylic acid group of beta-D-gentiobiosyl crocetin with the anomeric hydroxy group of beta-D-glucopyranose. It is a beta-D-glucoside and a diester. Crocetin gentiobiosylglucosyl ester is a natural product found in Gardenia jasminoides and Crocus sativus with data available. Isolated from saffron (Crocus sativus) Crocin II is isolated from the fruit of Gardenia jasminoides with antioxidant, anticancer, and antidepressant activity. Crocin II inhibits NO production with an IC50 value of 31.1 μM. Crocin II suppresses the expressions of protein and m-RNA of iNOS and COX-2[1]. Crocin II is isolated from the fruit of Gardenia jasminoides with antioxidant, anticancer, and antidepressant activity. Crocin II inhibits NO production with an IC50 value of 31.1 μM. Crocin II suppresses the expressions of protein and m-RNA of iNOS and COX-2[1].

(2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol

C10H18O (154.1358)

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. It has a role as a volatile oil component and a metabolite. Isoborneol is a natural product found in Xylopia sericea, Eupatorium capillifolium, and other organisms with data available. Both Borneol and Isoborneol and their acetates and formates are used as flavouring agents. 2-Bornanol is found in turmeric. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Secoisolariciresinol

C20H26O6 (362.1729)

Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\\\% . (-)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration. It has a role as an antidepressant, a plant metabolite and a phytoestrogen. It is an enantiomer of a (+)-secoisolariciresinol. Secoisolariciresinol has been used in trials studying the prevention of Breast Cancer. Secoisolariciresinol is a natural product found in Fitzroya cupressoides, Crossosoma bigelovii, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Gardoside

C16H22O10 (374.1213)

Gardoside is a glycoside. Gardoside is a natural product found in Plantago atrata, Gardenia jasminoides, and other organisms with data available.

Stearic acid

C18H36O2 (284.2715)

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Syringic acid

C9H10O5 (198.0528)

Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID:18767860). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563). Syringic acid is a dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. It has a role as a plant metabolite. It is a member of benzoic acids, a dimethoxybenzene and a member of phenols. It is functionally related to a gallic acid. It is a conjugate acid of a syringate. Syringic acid is a natural product found in Visnea mocanera, Pittosporum illicioides, and other organisms with data available. Syringic acid is a metabolite found in or produced by Saccharomyces cerevisiae. Present in various plants free and combined, e.g. principal phenolic constituent of soyabean meal (Glycine max) A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents KEIO_ID S018 Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

Oleic acid

C18H34O2 (282.2559)

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Eugenol

C10H12O2 (164.0837)

Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992) Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. It has a role as an allergen, a human blood serum metabolite, a sensitiser, a volatile oil component, a flavouring agent, an EC 1.4.3.4 (monoamine oxidase) inhibitor, a radical scavenger, an antibacterial agent, an antineoplastic agent, an apoptosis inducer, an anaesthetic, an analgesic, a voltage-gated sodium channel blocker, a NF-kappaB inhibitor and an anti-inflammatory agent. It is a phenylpropanoid, a monomethoxybenzene, a member of phenols and an alkenylbenzene. It is functionally related to a guaiacol. Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache. Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity. Eugenol, also called clove oil, is an aromatic oil extracted from cloves that is used widely as a flavoring for foods and teas and as an herbal oil used topically to treat toothache and more rarely to be taken orally to treat gastrointestinal and respiratory complaints. Eugenol in therapeutic doses has not been implicated in causing serum enzyme elevations or clinically apparent liver injury, but ingestions of high doses, as with an overdose, can cause severe liver injury. Eugenol is a natural product found in Dahlia sherffii, Elettaria cardamomum, and other organisms with data available. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). 4-Allyl-2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae. A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS. See also: Cinnamon (part of); Clove Oil (part of); Cinnamon Leaf Oil (part of) ... View More ... Eugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Eugenol has a very widespread occurrence in essential oils. Major component of clove oil. Also found in citrus and thyme oils. It is found in foods such as apple, apricot, banana and cherry fruits. Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054 ; PMID:935250 ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920 ). A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D000890 - Anti-Infective Agents D012997 - Solvents [Raw Data] CB226_Eugenol_pos_10eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_20eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_40eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_50eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_30eV_CB000079.txt Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation. Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

Glycerol

C3H8O3 (92.0473)

Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously. Glycerol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-81-5 (retrieved 2024-07-01) (CAS RN: 56-81-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Nevadensin

C18H16O7 (344.0896)

Nevadensin, also known as pedunculin or 5,7-hydroxy-4,6,8-trimethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, nevadensin is considered to be a flavonoid lipid molecule. Nevadensin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nevadensin can be found in peppermint and sweet basil, which makes nevadensin a potential biomarker for the consumption of these food products. Nevadensin is a naturally occurring selective inhibitor of human carboxylesterase 1 (hCE1) with an IC50 of 2.64 μM. Nevadensin has a variety of pharmacological effects such as anti-mycobacterium tuberculosis activities, antitussive, anti-inflammatory and anti-hypertensive[1][2]. Nevadensin is a naturally occurring selective inhibitor of human carboxylesterase 1 (hCE1) with an IC50 of 2.64 μM. Nevadensin has a variety of pharmacological effects such as anti-mycobacterium tuberculosis activities, antitussive, anti-inflammatory and anti-hypertensive[1][2].

Geniposidic acid

C16H22O10 (374.1213)

Geniposidic acid is found in beverages. Geniposidic acid is a constituent of Genipa americana (genipap) Constituent of Genipa americana (genipap). Geniposidic acid is found in beverages and fruits. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

Gardenoside

C17H24O11 (404.1319)

A cyclopentapyran that is 7-deoxyloganin with a methyl and hydrogen replaced by hydroxy and hydroxymethyl groups at position 7. Gardenoside is a natural product found in Gardenia jasminoides, Catunaregam obovata, and other organisms with data available. Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2]. Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2]. Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2].

Benzyl alcohol

C7H8O (108.0575)

Benzyl alcohol is a colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with Lidocaine injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutical aid, and in perfumery and flavoring. Benzyl Alcohol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. Benzyl alcohol is metabolized to Benzoic Acid, which reacts with glycine and excreted as hippuric acid in the human body. Acceptable daily intakes were established by the World Health Organization at 5 mg/kg for Benzyl alcohol. No adverse effects of benzyl alcohol have been seen in chronic exposure animal studies using rats and mice. Effects of Benzyl Alcohol in chronic exposure animal studies are limited to reduced feed intake and reduced growth. Some differences have been noted in one reproductive toxicity study using mice, but these were limited to lower maternal body weights and decreased mean litter weights. Another study also noted that fetal weight was decreased compared to controls, but a third study showed no differences between control and benzyl alcohol-treated groups. Benzyl alcohol has been associated with an increased number of resorptions and malformations in hamsters, but there have been no reproductive or developmental toxicity findings in studies using mice and rats. Genotoxicity tests for benzyl alcohol are mostly negative, but there were some assays that were positive. Carcinogenicity studies, however, were negative. Clinical data indicates that benzyl alcohol can produce nonimmunologic contact urticaria and nonimmunologic immediate contact reactions, characterized by the appearance of wheals, erythema, and pruritis. 5\\\\% benzyl alcohol can elicit a reaction. Benzyl alcohol is not a sensitizer at 10\\\\%. Benzyl alcohol could be used safely at concentrations up to 5\\\\%, but that manufacturers should consider the nonimmunologic phenomena when using benzyl alcohol in cosmetic formulations designed for infants and children. Additionally, Benzyl alcohol is considered safe up to 10\\\\% for use in hair dyes. The limited body exposure, the duration of use, and the frequency of use are considered in concluding that the nonimmunologic reactions would not be a concern. Because of the wide variety of product types in which benzyl alcohol may be used, it is likely that inhalation may be a route of exposure. The available safety tests are not considered sufficient to support the safety of benzyl alcohol in formulations where inhalation is a route of exposure. Inhalation toxicity data are needed to complete the safety assessment of benzyl alcohol where inhalation can occur. (PMID:11766131). Constituent of jasmine and other ethereal oils, both free and as estersand is also present in cherry, orange juice, mandarin peel oil, guava fruit, feijoa fruit, pineapple, leek, cinnamon, cloves, mustard, fermented tea, basil and red sage. Flavouring ingredient P - Antiparasitic products, insecticides and repellents > P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents > P03A - Ectoparasiticides, incl. scabicides D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Benzyl alcohol is an aromatic alcohol, a colorless liquid with a mild aromatic odor. Benzyl alcohol is an aromatic alcohol, a colorless liquid with a mild aromatic odor.

Ethyl octanoate

C10H20O2 (172.1463)

Ethyl octanoate is a fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol. It has a role as a metabolite. It is a fatty acid ethyl ester and an octanoate ester. Ethyl octanoate is found in alcoholic beverages. Ethyl octanoate is used in many fruit flavourings. Ethyl octanoate is a constituent of plant oils. Also present in Swiss cheese, Camembert cheese, wheat bread, port wine, plum brandy, sparkling wine, apple, apricot, banana, cherry, orange, grapefruit, plum and other fruits. It is used in many fruit flavourings. Constituent of plant oilsand is) also present in Swiss cheese, Camembert cheese, wheat bread, port wine, plum brandy, sparkling wine, apple, apricot, banana, cherry, orange, grapefruit, plum and other fruits. Ethyl octanoate is found in many foods, some of which are milk and milk products, guava, cereals and cereal products, and pepper (c. frutescens).

Arvensoside D

C48H78O18 (942.5188)

Arvensoside D is a constituent of Calendula officinalis (pot marigold). Constituent of Calendula officinalis (pot marigold)

Acerosin

C18H16O8 (360.0845)

Acerosin is found in citrus. Acerosin is isolated from fruit peel of mandarin orange (Citrus reticulata

Tarennoside

C16H22O9 (358.1264)

Gardenin B

C19H18O7 (358.1052)

Gardenin b, also known as demethyltangeretin or 5-hydroxy-4,6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1]. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].

Clionasterol

C29H50O (414.3861)

Clionasterol is a triterpenoid isolated from the Indian marine red alga Gracilaria edulis, the sponge Veronica aerophoba and the Kenyan Marine Green. Macroalga Halimeda macroloba. It is a potent inhibitor of complement component C1. (PMID 12624828). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

Tartaric acid

C4H6O6 (150.0164)

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20\\\\\\% of consumed tartaric acid is secreted in the urine unchanged. Tartaric acid is a biomarker for the consumption of wine and grapes (PMID:24507823). Tartaric acid is also a fungal metabolite, elevated levels in the urine (especially in children) may be due to the presence of yeast (in the gut or bladder). It can be produced by Agrobacterium, Nocardia, Rhizobium, Saccharomyces as well (PMID:7628083) (https://link.springer.com/article/10.1023/A:1005592104426). High levels of tartaric acid have been found in autistic children. In adults, tartaric acid may be due to the consumption of wine (https://www.greatplainslaboratory.com/articles-1/2015/11/13/candida-and-overgrowth-the-problem-bacteria-by-products) (PMID:15738524; PMID:24507823; PMID:7628083). Present in many fruits, wines and coffee. Acidulant for beverages, foods and pharmaceuticals,used to enhance natural and synthetic fruit flavours, especies in grape- and lime-flavoured drinks and candies. Firming agent, humectant. It is used in leavening systems including baking powders. Stabiliising agent for ground spices and cheeses to prevent discoloration. Chelating agent in fatty foods. Synergist with antioxidants, pH control agent in milk, jams and jellies, moisture-control agent. *Metatartaric* acid (a mixture of polyesters obtained by the controlled dehydration of (+)-tartaric acid, together with unchanged (+)-tartaric acid) is permitted in wine in UK (+)-Tartaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-69-4 (retrieved 2024-07-01) (CAS RN: 87-69-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Tartaric acid is a non-racemic mixture of L- and D-tartaric acids with antioxidant activities[1][2]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1].

Syringaldehyde

C9H10O4 (182.0579)

Syringaldehyde is a hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a plant metabolite. It is a hydroxybenzaldehyde and a dimethoxybenzene. Syringaldehyde is a natural product found in Ficus septica, Mikania laevigata, and other organisms with data available. Syringaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae. A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

3-Epioleanolic acid

C30H48O3 (456.3603)

3-epioleanolic acid is a triterpenoid. It has a role as a metabolite. 3-Epioleanolic acid is a natural product found in Conandron ramondioides, Gardenia ternifolia, and other organisms with data available. 3-Epioleanolic acid is found in common sage. 3-Epioleanolic acid is isolated from sage Salvia officinalis and other plants. Isolated from sage Salvia officinalis and other plants. 3-Epioleanolic acid is found in common sage. A natural product found in Radermachera boniana. 3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1]. 3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1].

Pinoresinol

C20H22O6 (358.1416)

4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol is a natural product found in Zanthoxylum riedelianum, Forsythia suspensa, and other organisms with data available. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Dicaffeoylquinic acid

C25H24O12 (516.1268)

Isolated from coffee and maté, globe artichoke (Cynara scolymus) and caucasian whortleberry (Vaccinium arctostaphylos). 3,5-Di-O-caffeoylquinic acid is found in many foods, some of which are potato, green vegetables, coffee and coffee products, and carrot. Dicaffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313) Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antioxidant and anti-inflammatory activities . Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antioxidant and anti-inflammatory activities .

Pomolic acid

C30H48O4 (472.3552)

Constituent of apple peel. Pomolic acid is found in many foods, some of which are rosemary, lemon balm, pomes, and spearmint. Pomolic acid is found in apple. Pomolic acid is a constituent of apple peel Randialic acid A (Pomolic acid) is a pentacyclic triterpene isolated from?Euscaphis japonica?(Tunb.). Randialic acid A (Pomolic acid) inhibits tumor cells growth and induces cell apoptosis. Randialic acid A (Pomolic acid) has a potential for the treatment of prostate cancer (PC)[2]. Randialic acid A (Pomolic acid) is a pentacyclic triterpene isolated from?Euscaphis japonica?(Tunb.). Randialic acid A (Pomolic acid) inhibits tumor cells growth and induces cell apoptosis. Randialic acid A (Pomolic acid) has a potential for the treatment of prostate cancer (PC)[2].

Rhamnazin 3-rutinoside

C29H34O16 (638.1847)

Rhamnazin 3-rutinoside is found in fruits. Rhamnazin 3-rutinoside is isolated from Cucurbita pepo. Isolated from Cucurbita pepo. Rhamnazin 3-rutinoside is found in fruits.

L-Linalool 3-[xylosyl-(1->6)-glucoside]

C21H36O10 (448.2308)

L-Linalool 3-[xylosyl-(1->6)-glucoside] is found in tea. L-Linalool 3-[xylosyl-(1->6)-glucoside] is an aroma precursor from tea (Camellia sinensis var. sinensis). Aroma precursor from tea (Camellia sinensis variety sinensis). L-Linalool 3-[xylosyl-(1->6)-glucoside] is found in tea.

Genipic acid

C9H12O4 (184.0736)

Genipic acid is found in beverages. Genipic acid is isolated from the jagua fruit Genipa american Isolated from the jagua fruit Genipa americana. Genipic acid is found in beverages and fruits.

(3b,24x)-Cycloartane-3-oxo-24,25-diol

C30H50O3 (458.376)

(3b,24x)-Cycloartane-3-oxo-24,25-diol is found in fruits. (3b,24x)-Cycloartane-3-oxo-24,25-diol is a constituent of Artocarpus heterophyllus (jackfruit). Constituent of Artocarpus heterophyllus (jackfruit). (3b,24x)-Cycloartane-3-oxo-24,25-diol is found in fruits.

Queretaroic acid

C30H48O4 (472.3552)

Queretaroic acid is found in cereals and cereal products. Queretaroic acid is a constituent of Chenopodium quinoa (quinoa), Stenocereus thurberi (organ pipe cactus) Constituent of Chenopodium quinoa (quinoa), Stenocereus thurberi (organ pipe cactus). Queretaroic acid is found in cereals and cereal products and fruits.

Epijasminoside A

C16H26O7 (330.1678)

Epijasminoside A is a constituent of Saffron (Crocus sativus). Constituent of Saffron (Crocus sativus).

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one

C22H22O11 (462.1162)

Genipinic acid

C11H14O6 (242.079)

Genipinic acid is found in beverages. Genipinic acid is isolated from the jagua fruit Genipa americana. Isolated from the jagua fruit Genipa americana. Genipinic acid is found in beverages and fruits.

Calycopterin

C19H18O8 (374.1002)

Sarothrin

C18H16O8 (360.0845)

Carissic acid

C30H48O3 (456.3603)

Ustiloxin E is found in cereals and cereal products. Ustiloxin E is isolated from the false smut balls caused by Ustilaginoidea virens on rice. Constituent of Carissa carandas (karanda). Carissic acid is found in beverages and fruits.

beta-Amyrin

C30H50O (426.3861)

Beta-amryin, also known as B-amryin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amryin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amryin can be found in pigeon pea, which makes beta-amryin a potential biomarker for the consumption of this food product.

beta-Amyrin acetate

C32H52O2 (468.3967)

Beta-amyrin acetate, also known as B-amyrin acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amyrin acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-amyrin acetate can be found in burdock and guava, which makes beta-amyrin acetate a potential biomarker for the consumption of these food products. β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

Crocetin

C20H24O4 (328.1675)

Deacetylasperulosidic acid

C16H22O11 (390.1162)

Epipinoresinol

C20H22O6 (358.1416)

(+)-pinoresinol is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-pinoresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-pinoresinol can be found in a number of food items such as chanterelle, pecan nut, pine nut, and common hazelnut, which makes (+)-pinoresinol a potential biomarker for the consumption of these food products. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Scandoside methyl ester

C17H24O11 (404.1319)

Flaxseeds extract

C20H26O6 (362.1729)

Secoisolariciresinol is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as barley, wheat bread, broad bean, and poppy, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\% .

Gardenoside

C17H24O11 (404.1319)

Genipin 1-gentiobioside

C23H34O15 (550.1898)

Geniposide

C17H24O10 (388.1369)

Hederagenin

C30H48O4 (472.3552)

Hederagenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Hederagenin is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hederagenin can be found in a number of food items such as rye, dill, european cranberry, and black salsify, which makes hederagenin a potential biomarker for the consumption of these food products. Hederagenin is the aglycone part of numerous saponins found in Hedera helix (common ivy). The most prevalent of these being hederacoside C and alpha-hederin. It is also one of three primary triterpenoids extracted from the Chenopodium quinoa plant categorized by the EPA as a biopesticide. HeadsUp Plant Protectant is made up of approximately equal ratios of the saponin aglycones oleanolic acid, hederagenin, and phytolaccagenic acid and is intended for use as a seed treatment on tuber (e.g. potato seed pieces), legume, and cereal seeds or as a pre-plant root dip for roots of transplants, at planting, to prevent fungal growth, bacterial growth, and viral plant diseases .

Lupenone

C30H48O (424.3705)

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Lupenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lupenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Rohitukine

C16H19NO5 (305.1263)

Shanzhiside

C16H24O11 (392.1319)

Syringaldehyde

C9H10O4 (182.0579)

4-hydroxy-3,5-dimethoxybenzaldehyde, also known as sinapaldehyde or 2,6-dimethoxy-4-formylphenol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-hydroxy-3,5-dimethoxybenzaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxy-3,5-dimethoxybenzaldehyde is a mild, sweet, and plastic tasting compound and can be found in a number of food items such as whisky, common grape, garden tomato (variety), and coriander, which makes 4-hydroxy-3,5-dimethoxybenzaldehyde a potential biomarker for the consumption of these food products. 4-hydroxy-3,5-dimethoxybenzaldehyde may be a unique S.cerevisiae (yeast) metabolite. Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53 . Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

Scopolin

C16H18O9 (354.0951)

Scopolin is a member of the class of compounds known as coumarin glycosides. Coumarin glycosides are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Scopolin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Scopolin can be found in a number of food items such as sweet potato, oat, wild celery, and potato, which makes scopolin a potential biomarker for the consumption of these food products. Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase . Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

Hispidulin

C16H12O6 (300.0634)

Hispidulin is a monomethoxyflavone that is scutellarein methylated at position 6. It has a role as an apoptosis inducer, an anti-inflammatory agent, an antioxidant, an anticonvulsant, an antineoplastic agent and a plant metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a scutellarein. Hispidulin (4,5,7-trihydroxy-6-methoxyflavone) is a potent benzodiazepine (BZD) receptor ligand with positive allosteric properties. Hispidulin is a natural product found in Eupatorium cannabinum, Eupatorium perfoliatum, and other organisms with data available. See also: Arnica montana Flower (part of). A monomethoxyflavone that is scutellarein methylated at position 6. 6-methylscutellarein, also known as 4,5,7-trihydroxy-6-methoxyflavone or dinatin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 6-methylscutellarein is considered to be a flavonoid lipid molecule. 6-methylscutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-methylscutellarein can be found in a number of food items such as italian oregano, common sage, sunflower, and common thyme, which makes 6-methylscutellarein a potential biomarker for the consumption of these food products. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM.

5,7,3-rihydroxy-6,4,5-rimethoxyflavone

C18H16O8 (360.0845)

5,7,3-Trihydroxy-6,4,5-trimethoxyflavone is a natural product found in Eupatorium capillifolium, Artemisia kurramensis, and other organisms with data available. 5,7,3'-Trihydroxy-6,4',5'-trimethoxyflavone is a methylated flavones from Artemisia frigida. 5,7,3'-Trihydroxy-6,4',5'-trimethoxyflavone is a methylated flavones from Artemisia frigida.

Geniposidic_acid

C16H22O10 (374.1213)

Geniposidic acid is a terpene glycoside. Geniposidic acid is a natural product found in Avicennia officinalis, Gardenia jasminoides, and other organisms with data available. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

Hederagenin

C30H48O4 (472.3552)

Hederagenin is a sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer). It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a dihydroxy monocarboxylic acid and a sapogenin. It is functionally related to an oleanolic acid. It is a conjugate acid of a hederagenin(1-). It derives from a hydride of an oleanane. Hederagenin is a natural product found in Zygophyllum obliquum, Sapindus emarginatus, and other organisms with data available. See also: Paeonia lactiflora root (part of); Caulophyllum robustum Root (part of); Medicago sativa whole (part of). A sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer). Hederagenin is a triterpenoid saponin that can inhibit the expression of iNOS, COX-2, and NF-κB in cells caused by LPS stimulation. Hederagenin is a triterpenoid saponin that can inhibit the expression of iNOS, COX-2, and NF-κB in cells caused by LPS stimulation.

Ursolic Acid

C30H48O3 (456.3603)

Origin: Plant; SubCategory_DNP: Triterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.640 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.638 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.642 Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Rohitukine

C16H19NO5 (305.1263)

A member of the class of chromones that is 4H-chromen-4-one in which the hydrogens at positions 2,5,7 and 8 are replaced by methyl, hydroxy, hydroxy, and (3S,4R)-3-hydroxy-1-methylpiperidin-4-yl groups, respectively. It is an alkaloid initially isolated from Amoora rohituka and is a precursor of the anti-cancer compound flavopiridol.

Ethyl ferulate

C12H14O4 (222.0892)

Ethyl ferulate, a naturally lipophilic derivative of ferulic acid originally derived from Rhizoma Chuanxiong, induces heme oxygenase-1 (HO-1) and protects rat neurons against oxidative stress[1]. Ethyl ferulate also protects neurons against amyloid β peptide (1-42)-induced oxidative stress and neurotoxicity[2]. Ethyl ferulate, a naturally lipophilic derivative of ferulic acid originally derived from Rhizoma Chuanxiong, induces heme oxygenase-1 (HO-1) and protects rat neurons against oxidative stress[1]. Ethyl ferulate also protects neurons against amyloid β peptide (1-42)-induced oxidative stress and neurotoxicity[2].

Jasminodiol

C10H16O3 (184.1099)

β-Amyrin

C30H50O (426.3861)

Beta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee . β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Palmitic Acid

C16H32O2 (256.2402)

COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Deacetylasperulosidic acid

C16H22O11 (390.1162)

Deacetylasperulosidic acid (DAA) is a major phytochemical constituent of Morinda citrifolia fruit. Deacetylasperulosidic acidhas antioxidant activity by increasing superoxide dismutase activity. Deacetylasperulosidic acid has anticlastogenic activity, suppressing the induction of chromosome aberrations in hamster ovary cells and mice[1]. Deacetylasperulosidic acid prevents 4-nitroquinoline 1-oxide (4NQO) induced DNA damage in vitro, suppresses IL-2 production along with the activation of natural killer cells[2]. Deacetylasperulosidic acid (DAA) is a major phytochemical constituent of Morinda citrifolia fruit. Deacetylasperulosidic acidhas antioxidant activity by increasing superoxide dismutase activity. Deacetylasperulosidic acid has anticlastogenic activity, suppressing the induction of chromosome aberrations in hamster ovary cells and mice[1]. Deacetylasperulosidic acid prevents 4-nitroquinoline 1-oxide (4NQO) induced DNA damage in vitro, suppresses IL-2 production along with the activation of natural killer cells[2].

Umuhengerin

C20H20O8 (388.1158)

Gardenin E

C19H18O9 (390.0951)

Gardenin A

C21H22O9 (418.1264)

Calycopterin

C19H18O8 (374.1002)

Lethedocin

C18H16O7 (344.0896)

sitosterol

C29H50O (414.3861)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

Conyzatin

C20H20O9 (404.1107)

Sarothrin

C18H16O8 (360.0845)

Acerosin

C18H16O8 (360.0845)

A trihydroxyflavone that is 5,7,3-trihydroxyflavone with methoxy substituents at positions 6, 8 and 4 respectively.

Gardenin B

C19H18O7 (358.1052)

Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1]. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].

Desmethoxysudachitin

C17H14O7 (330.0739)

Nevadensin

C18H16O7 (344.0896)

Nevadensin is a naturally occurring selective inhibitor of human carboxylesterase 1 (hCE1) with an IC50 of 2.64 μM. Nevadensin has a variety of pharmacological effects such as anti-mycobacterium tuberculosis activities, antitussive, anti-inflammatory and anti-hypertensive[1][2]. Nevadensin is a naturally occurring selective inhibitor of human carboxylesterase 1 (hCE1) with an IC50 of 2.64 μM. Nevadensin has a variety of pharmacological effects such as anti-mycobacterium tuberculosis activities, antitussive, anti-inflammatory and anti-hypertensive[1][2].

Quercetin

C15H10O7 (302.0427)

Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Isoquercetin

C21H20O12 (464.0955)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor.

Syringaldehyde

C9H10O4 (182.0579)

Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 303; CONFIDENCE confident structure Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

β-Amyrin acetate

C32H52O2 (468.3967)

β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

Chlorogenic Acid

C16H18O9 (354.0951)

IPB_RECORD: 1901; CONFIDENCE confident structure Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

lupeol

C30H50O (426.3861)

D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

Lupenone

C30H48O (424.3705)

Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2]. Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3]. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

5,7-dihydroxy-2-(2,3,4,5,6-pentamethoxyphenyl)chromen-4-one

C20H20O9 (404.1107)

betulinic acid

C30H48O3 (456.3603)

Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

Esculin

C15H16O9 (340.0794)

Origin: Plant; Formula(Parent): C15H16O9; Bottle Name:Esculin sesquihydrate; PRIME Parent Name:6,7-Dihydroxycoumarin-6-glucoside; PRIME in-house No.:V0125, Coumarins relative retention time with respect to 9-anthracene Carboxylic Acid is 0.391 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.385 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.384 Esculin, a fluorescent coumarin glucoside, is an active ingredient of ash bark[1]. Esculin ameliorates cognitive impairment in experimental diabetic nephropathy (DN), and exerts anti?oxidative stress and anti?inflammatory effects, via the MAPK signaling pathway[2]. Esculin, a fluorescent coumarin glucoside, is an active ingredient of ash bark[1]. Esculin ameliorates cognitive impairment in experimental diabetic nephropathy (DN), and exerts anti?oxidative stress and anti?inflammatory effects, via the MAPK signaling pathway[2].

Oleanolic Acid

C30H48O3 (456.3603)

Balanophonin

C20H20O6 (356.126)

(+)-Balanophonin is a natural product found in Balanophora japonica, Catunaregam spinosa, and other organisms with data available. Balanophonin is a natural product found in Lonicera insularis, Carya cathayensis, and other organisms with data available.

5-hydroxy-7-methoxy-2-(2,3,4,5,6-pentamethoxyphenyl)chromen-4-one

C21H22O9 (418.1264)

5-hydroxy-7-methoxy-2-(2,3,4,5-tetramethoxyphenyl)chromen-4-one

C20H20O8 (388.1158)

2-METHYLHEPTADECANE

C18H38 (254.2973)

β-Amyrin acetate

C32H52O2 (468.3967)

Beta-amyrin acetate is a triterpenoid. beta-Amyrin acetate is a natural product found in Euphorbia decipiens, Euphorbia larica, and other organisms with data available. β-Amyrin acetate is a triterpenoid with potent anti-inflammatory, antifungal, anti-diabetic, anti-hyperlipidemic activities. β-Amyrin acetate can inhibit HMG-CoA reductase activity by locating in the hydrophobic binding cleft of HMG CoA reductase[1][2][3][4].

Scopoletin

C10H8O4 (192.0423)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

Campesterol

C28H48O (400.3705)

Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Geniposidic acid

C16H22O10 (374.1213)

Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

Scoparone

C11H10O4 (206.0579)

Annotation level-1 D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents Scoparone is isolated from Artemisia capillaris Thunb., has anticoagulant, vasorelaxant antioxidant, anti-inflammatory activities[1]. Scoparone is isolated from Artemisia capillaris Thunb., has anticoagulant, vasorelaxant antioxidant, anti-inflammatory activities[1].

Salicin

C13H18O7 (286.1052)

D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D004791 - Enzyme Inhibitors relative retention time with respect to 9-anthracene Carboxylic Acid is 0.253 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.247 Salicin is a natural COX inhibitor. Salicin is a natural COX inhibitor.

Genipin

C11H14O5 (226.0841)

Genipin is an iridoid monoterpenoid. It has a role as an uncoupling protein inhibitor, a hepatotoxic agent, an apoptosis inhibitor, an antioxidant, an anti-inflammatory agent and a cross-linking reagent. Genipin is a natural product found in Gardenia jasminoides, Rothmannia globosa, and other organisms with data available. D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics relative retention time with respect to 9-anthracene Carboxylic Acid is 0.593 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.589 Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2]. Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2]. Genipin ((+)-Genipin) is a natural crosslinking reagent derived from Gardenia jasminoides Ellis fruits. Genipin inhibits UCP2 (uncoupling protein 2) in cells. Genipin has a variety of bioactivities, including modulation on proteins, antitumor, anti-inflammation, immunosuppression, antithrombosis, and protection of hippocampal neurons. Genipin also can be used for type 2 diabetes research[1][2].

Secoisolariciresinol

C20H26O6 (362.1729)

Annotation level-1 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.816 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.813 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.806 Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Trigonelline

C7H7NO2 (137.0477)

MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WWNNZCOKKKDOPX-UHFFFAOYSA-N_STSL_0022_Trigonelline (chloride)_0125fmol_180416_S2_LC02_MS02_26; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis. Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis.

benzyl alcohol

C7H8O (108.0575)

Benzyl alcohol is an aromatic alcohol, a colorless liquid with a mild aromatic odor. Benzyl alcohol is an aromatic alcohol, a colorless liquid with a mild aromatic odor.

L(+)-Tartaric acid

C4H6O6 (150.0164)

L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1].

Ferulic acid

C10H10O4 (194.0579)

(E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

Vanillic Acid

C8H8O4 (168.0423)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

stearic acid

C18H36O2 (284.2715)

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Oleic acid

C18H34O2 (282.2559)

An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. Oleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=112-80-1 (retrieved 2024-07-16) (CAS RN: 112-80-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-dimethoxychromen-4-one

C17H14O8 (346.0689)

Benzoic Acid

C7H6O2 (122.0368)

Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

3,4-dicaffeoylquinic acid

C25H24O12 (516.1268)

3,5-dicaffeoylquinic acid

C25H24O12 (516.1268)

Genipin 1-gentiobioside

C23H34O15 (550.1898)

Genipin 1-β-D-gentiobioside (Genipin 1-gentiobioside) is one of the most abundant and bioactive iridoid glycosides in Gardenia jasminoides Ellis, which possesses hepatoprotective, anti-inflammatory, antioxidant, and antithrombotic activities. Genipin 1-β-D-gentiobioside (Genipin 1-gentiobioside) is one of the most abundant and bioactive iridoid glycosides in Gardenia jasminoides Ellis, which possesses hepatoprotective, anti-inflammatory, antioxidant, and antithrombotic activities.

glycerol

C3H8O3 (92.0473)

A triol with a structure of propane substituted at positions 1, 2 and 3 by hydroxy groups.

Syringic acid

C9H10O5 (198.0528)

Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266)

Crocin

C44H64O24 (976.3787)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Crocin (Crocin I) is a nutraceutical and the main constituent isolated from the stigmas of Crocus sativus with immense pharmacological properties as anti-inflammatory, anticancer, antidepressant and anticonvulsant[1]. Crocin (Crocin I) is a nutraceutical and the main constituent isolated from the stigmas of Crocus sativus with immense pharmacological properties as anti-inflammatory, anticancer, antidepressant and anticonvulsant[1].

Eugenol

C10H12O2 (164.0837)

C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D000890 - Anti-Infective Agents D012997 - Solvents Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation. Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-dimethoxychromen-4-one

C17H14O8 (346.0689)

2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

C20H26O6 (362.1729)

(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1268)

Crocetin

C20H24O4 (328.1675)

Crocetin is a 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement. It has a role as a nutraceutical, a metabolite and an antioxidant. It is a carotenoic acid, a diterpenoid and a polyunsaturated dicarboxylic acid. It is a conjugate acid of a crocetin(2-). Vitamin A-analog that increases diffusivity of oxygen in aqueous solutions, including plasma. Crocetin is a natural product found in Verbascum lychnitis, Gardenia jasminoides, and other organisms with data available. A 20-carbon dicarboxylic acid which is a diterpenoid and natural carotenoid. Found in the crocus flower, it has been administered as an anti-fatigue dietary supplement. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Crocetin is a natural carotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides (fruits).

Hexadecanoic acid

C16H32O2 (256.2402)

Octadecanoic acid

C18H36O2 (284.2715)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

4-Hydroxy-3,5-dimethoxybenzaldehyde

C9H10O4 (182.0579)

Neohancoside a

C21H36O10 (448.2308)

4,5-DCQA

C25H24O12 (516.1268)

3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3]. 3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3]. 4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3]. 4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3].

Epijasminoside A

C16H26O7 (330.1678)

Monomethyl fumarate

C5H6O4 (130.0266)

A dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. C26170 - Protective Agent > C1509 - Neuroprotective Agent Monomethyl fumarate, an active metabolite of Dimethyl fumarate (DMF), is a potent GPR109A agonist. Monomethyl fumarate has the potential for multiple neuroprotective pathways and other models of retinal disease[1][2][3].

Queretaroic acid

C30H48O4 (472.3552)

borneol

C10H18O (154.1358)

Flavouring agent. (±)-Borneol is found in many foods, some of which are pot marjoram, pepper (spice), saffron, and german camomile. Constituent of Curcuma aromatica and other plants. (+)-Borneol is found in nutmeg, herbs and spices, and ginger. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Genipic acid

C9H12O4 (184.0736)

Epi-Oleanolic Acid

C30H48O3 (456.3603)

3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1]. 3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1].

Genipinic acid

C11H14O6 (242.079)

Carissic acid

C30H48O3 (456.3603)

clionasterol

C29H50O (414.3861)

A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

Methyl 7-formylcyclopenta[c]pyran-4-carboxylate

C11H8O4 (204.0423)

Vanillate

C8H8O4 (168.0423)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

linoleic

C18H32O2 (280.2402)

Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

Deacetylasperulosidic acid

C16H22O11 (390.1162)

Borneol

C10H18O (154.1358)

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. It has a role as a volatile oil component and a metabolite. Isoborneol is a natural product found in Xylopia sericea, Eupatorium capillifolium, and other organisms with data available. A bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Octadec-9-enoic acid

C18H34O2 (282.2559)

An octadecenoic acid with a double bond at C-9.

2,3-Dihydroxybutanedioic acid

C4H6O6 (150.0164)

A tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3.

(1s,3ar,3br,5ar,9ar,9br,11ar)-3a,3b,6,6,9a-pentamethyl-1-[(2s,5s)-2,5,6-trihydroxy-6-methylheptan-2-yl]-dodecahydrocyclopenta[a]phenanthren-7-one

C30H52O4 (476.3865)

methyl (1s,4r,7s,8r,9s,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

10-[(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C41H66O14 (782.4452)

7-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-5-hydroxy-2-methylchromen-4-one

C21H26O13 (486.1373)

methyl (1r,4r,7s,8s,9s,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

(3r,4as,6ar,6bs,8ar,12ar,14as,14br)-3-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-3,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-2h-picen-1-one

C30H48O2 (440.3654)

methyl (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H26O10 (390.1526)

(4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2r,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C48H78O18 (942.5188)

methyl (1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H26O10 (390.1526)

(2r,3r,4s,5s,6r)-2-[(3r)-oct-1-en-3-yloxy]-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C19H34O10 (422.2152)

ethyl (1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxy-5-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

C29H32O13 (588.1843)

methyl 10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1-oxo-4,5,6,7,8,8a,10,11,12,12b,13,14b-dodecahydro-3h-picene-4a-carboxylate

C33H50O5 (526.3658)

(1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C27H32O14 (580.1792)

(1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-4-oxohept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,14-dione

C30H44O3 (452.329)

4-(5,7-dihydroxy-2-methyl-4-oxochromen-6-yl)-1-methylpiperidin-2-one

C16H17NO5 (303.1107)

1-(5,6-dihydroxy-6-methylhept-2-en-2-yl)-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-7-one

C30H50O3 (458.376)

(1s,3r,4s,4as,7s,7as)-3-(acetyloxy)-7-[(acetyloxy)methyl]-1-{[(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,3h,4h,4ah,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C28H36O17 (644.1952)

methyl 7-(hydroxymethyl)-5-methoxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C18H26O11 (418.1475)

methyl (1s,4ar,5r,7ar)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O11 (404.1319)

7-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-methoxychromen-2-one

C21H26O13 (486.1373)

methyl 5-butoxy-1-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C36H48O18 (768.2841)

methyl (1s,4r,7s,8s,9s,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one

C17H14O8 (346.0689)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1s,4ar,6as,6br,8ar,9r,10s,12ar,12br,14bs)-1-hydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-10-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5,6,7,8,8a,10,11,12,12b,13,14b-dodecahydro-3h-picene-4a-carboxylate

C41H64O14 (780.4296)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 2,6,6-trimethylcyclohex-1-ene-1-carboxylate

C22H36O12 (492.2207)

(3ar,4r,6s,7r)-7-hydroxy-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,3a,4,5,6,8-hexahydroazulen-2-one

C21H34O9 (430.2203)

1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)

3-[(1r,4s,5s,8r,9r,12r,13s)-4,8-dimethyl-5-[(2s)-6-methylhept-5-en-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

C30H48O2 (440.3654)

7-oxooctadec-11-enoic acid

C18H32O3 (296.2351)

methyl 3-[11,15-dimethyl-14-(6-methyl-4-oxohept-5-en-2-yl)-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H44O5 (496.3189)

3-ethoxy-7,7-dimethyl-hexahydro-2-benzofuran-5-one

C12H20O3 (212.1412)

methyl (1s,5s)-5-[(2s)-3-hydroxy-1-methoxy-1-oxopropan-2-yl]-2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate

C12H18O6 (258.1103)

5-hydroxy-2-methyl-1,11-dioxa-8-azatetraphene-4,10-dione

C16H9NO5 (295.0481)

methyl (1s,4ar,7r,7as)-7-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O11 (404.1319)

methyl (1s,4as,5s,7as)-5-butoxy-1-{[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C36H48O18 (768.2841)

methyl (1s,4ar,7ar)-7-oxo-1-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C16H20O10 (372.1056)

methyl (1r,4ar,7ar)-1,7a-dihydroxy-7-(hydroxymethyl)-1h,4ah,5h-cyclopenta[c]pyran-4-carboxylate

C11H14O6 (242.079)

7-{[(2s,3s,4r,5r,6s)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-methoxychromen-2-one

C21H26O13 (486.1373)

ethyl (1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

C29H32O13 (588.1843)

3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl 4-(acetyloxy)-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

C26H36O13 (556.2156)

2-(2,5-dihydroxy-3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one

C18H16O8 (360.0845)

methyl 3-[(1s,4r,5r,8s,9s,12r,13r)-12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[(2r,5e)-6-methyl-7-oxohept-5-en-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoate

C31H48O4 (484.3552)

(2r,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C54H88O22 (1088.5767)

methyl 1-hydroxy-7-(hydroxymethyl)-4ah,5h,7ah-cyclopenta[c]pyridine-4-carboxylate

C11H13NO4 (223.0845)

methyl (1r,4r,7s,8r,9s,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

(2s,3r,4s,5s,6r)-2-{[(3r)-3,7-dimethylocta-1,6-dien-3-yl]oxy}-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C21H36O10 (448.2308)

(4s)-3-(hydroxymethyl)-5,5-dimethyl-4-({[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C16H26O8 (346.1628)

{1-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C19H22O6 (346.1416)

(3,4,5-trihydroxy-6-{[6-(hydroxymethyl)-5,5-dimethyl-3-oxocyclohex-1-en-1-yl]methoxy}oxan-2-yl)methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

C27H36O12 (552.2207)

15-(7-hydroxy-6-methylhept-5-en-2-yl)-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-5,6-diol

C30H50O3 (458.376)

3-[(1s,4r,5r,8s,9s,12r,13r)-12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[(2r)-1-(4-methylfuran-2-yl)propan-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

C30H44O4 (468.3239)

4-{[(1s,2r,4s,6r)-2,6-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4-hydroxy-4-(methoxycarbonyl)cyclohexyl]oxy}-3-hydroxy-3-methyl-4-oxobutanoic acid

C31H32O16 (660.169)

2-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}-6-({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}oxy)oxane-3,4,5-triol

C21H36O10 (448.2308)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,2r,4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2s,3r,4s,5s)-4,5-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C47H76O17 (912.5082)

4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-1,10-diol

C30H50O3 (458.376)

[(3s,4s)-3-hydroxy-1h,3h,4h,5h,6h-cyclopenta[c]furan-4-yl]acetic acid

C9H12O4 (184.0736)

6-hydroxy-7,12,16-trimethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid

C31H50O3 (470.376)

methyl (1s,4as,7s,7as)-7-formyl-7-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C17H22O11 (402.1162)

(4ar,7r,7ar)-5,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C16H24O11 (392.1319)

methyl 3-[(1s,3r,4r,8r,10s,11s,14r,15r)-11,15-dimethyl-14-[(2r)-6-methylhept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H46O4 (482.3396)

methyl (4as,7as)-2-(2-hydroxyethyl)-7-(hydroxymethyl)-1-oxo-4ah,5h,7ah-cyclopenta[c]pyridine-4-carboxylate

C13H17NO5 (267.1107)

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

C27H28O13 (560.153)

methyl 3-[(1s,3r,4r,8r,10s,11s,14r,15r)-11,15-dimethyl-14-[(2r,5e)-6-methyl-7-oxohept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H44O5 (496.3189)

(4as,6as,6br,8as,12ar,12bs,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,12b,13,14b-dodecahydro-1h-picene-4a-carbaldehyde

C30H46O2 (438.3498)

3-[(1r,3s,4s,8s,10r,11r,14s,15s)-11,15-dimethyl-14-[(2s)-6-methylhept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoic acid

C30H44O4 (468.3239)

(1r,2s,3s,8r,10s)-4-(hydroxymethyl)-7,9,11-trioxatetracyclo[6.4.0.0²,⁶.0³,¹⁰]dodec-4-en-12-one

C10H10O5 (210.0528)

methyl 3-{11,15-dimethyl-14-[1-(4-methylfuran-2-yl)propan-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl}propanoate

C31H42O5 (494.3032)

(1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C16H24O10 (376.1369)

methyl 2,2,6a,6b,9,9,12a-heptamethyl-1,10-dioxo-3,4,5,6,7,8,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylate

C31H46O4 (482.3396)

6-methoxy-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

C16H18O9 (354.0951)

3,5-dicaffeoylquinic acid

C25H24O12 (516.1268)

{"Ingredient_id": "HBIN007602","Ingredient_name": "3,5-dicaffeoylquinic acid","Alias": "NA","Ingredient_formula": "C25H24O12","Ingredient_Smile": "C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O","Ingredient_weight": "516.4 g/mol","OB_score": "NA","CAS_id": "NA","SymMap_id": "NA","TCMID_id": "41070","TCMSP_id": "NA","TCM_ID_id": "21406","PubChem_id": "13604688","DrugBank_id": "NA"}

7-o-acetylloganicacid

C18H26O11 (418.1475)

{"Ingredient_id": "HBIN013373","Ingredient_name": "7-o-acetylloganicacid","Alias": "NA","Ingredient_formula": "C18H26O11","Ingredient_Smile": "CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C","Ingredient_weight": "418.4 g/mol","OB_score": "NA","CAS_id": "NA","SymMap_id": "SMIT14154","TCMID_id": "457","TCMSP_id": "NA","TCM_ID_id": "NA","PubChem_id": "101147141","DrugBank_id": "NA"}

(2r,3r,4s,5s,6r)-2-methoxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C13H24O11 (356.1319)

scopolin

C16H20O9 (356.1107)

(3s,4r,5r,6s)-2-ethoxy-6-(hydroxymethyl)oxane-3,4,5-triol

C8H16O6 (208.0947)

2-(3,5-dihydroxy-4-methoxyphenyl)-5-hydroxy-7-methoxychromen-4-one

C17H14O7 (330.0739)

7-{[(2s,3s,4s,5s,6s)-6-({[(2s,3s,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-methoxychromen-2-one

C21H26O13 (486.1373)

(1s,3r,9r,12s,13s,16r,17r)-13,17-dimethyl-16-[(2r)-6-methylhept-5-en-2-yl]-8-methylidene-7-oxapentacyclo[10.7.0.0¹,³.0³,⁹.0¹³,¹⁷]nonadecan-6-one

C29H44O2 (424.3341)

4-{[(1s,4as,7as)-4-(methoxycarbonyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methoxy}-4-oxobutanoic acid

C21H28O13 (488.153)

(1s,4as,7s,7as)-4-(methoxycarbonyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7h,7ah-cyclopenta[c]pyran-7-carboxylic acid

C17H22O11 (402.1162)

(1r,2s,4as,6as,6br,8as,10s,12ar,12br,14br)-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O4 (472.3552)

methyl 1,5-bis(acetyloxy)-7-[(acetyloxy)methyl]-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H20O9 (368.1107)

[1-(acetyloxy)-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-yl]methyl acetate

C14H20O5 (268.1311)

3-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-3,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-2h-picen-1-one

C30H48O2 (440.3654)

7,7,12,16-tetramethyl-15-(6-methyl-4-oxohept-5-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H46O2 (438.3498)

4-(methoxycarbonyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7h,7ah-cyclopenta[c]pyran-7-carboxylic acid

C17H22O11 (402.1162)

7,7,12,16-tetramethyl-15-(6-methylhepta-3,5-dien-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H46O (422.3548)

2-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C22H38O11 (478.2414)

2-(2,5-dihydroxy-3,4-dimethoxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one

C19H18O9 (390.0951)

(4s)-4-(5,7-dihydroxy-2-methyl-4-oxochromen-6-yl)-1-methylpiperidin-2-one

C16H17NO5 (303.1107)

methyl 7-(hydroxymethyl)-7-methoxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C18H26O11 (418.1475)

methyl 10-[(4-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl)oxy]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C48H78O17 (926.5239)

[(2r,3s,4s,5r,6r)-6-[(5,5-dimethyl-6-methylidene-3-oxocyclohex-1-en-1-yl)methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

C27H34O11 (534.2101)

methyl (1r,4s,7s,8s,9s,11s)-4-hydroxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-ene-11-carboxylate

C17H24O11 (404.1319)

(4r)-3,5,5-trimethyl-4-({[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C16H26O7 (330.1678)

methyl 7-formyl-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C17H22O11 (402.1162)

3-(hydroxymethyl)-5,5-dimethyl-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C16H26O8 (346.1628)

(2r,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-carbaldehyde

C18H18O6 (330.1103)

{3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

C27H36O11 (536.2258)

bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2e,4e,6z,8e,10e,12e,14e)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

C44H64O24 (976.3787)

(4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C42H68O13 (780.466)

(2r,3s,4s,5r,6r)-2-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-6-{[(1s,2s,4s)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]oxy}oxane-3,4,5-triol

C21H36O10 (448.2308)

(1s,4as,5r,7s,7as)-5,7-dihydroxy-7-methyl-1-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C16H24O11 (392.1319)

3,4-bis(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

C10H16O3 (184.1099)

methyl (1s,4ar,6as,6br,8ar,10r,12ar,12bs,14bs)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C31H50O4 (486.3709)

methyl 3-[(1r,3s,4s,8s,10r,11r,14s,15s)-11,15-dimethyl-14-[(2s)-6-methylhept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H46O4 (482.3396)

methyl 2-(2-hydroxyethyl)-7-(hydroxymethyl)-1-oxo-4ah,5h,7ah-cyclopenta[c]pyridine-4-carboxylate

C13H17NO5 (267.1107)

(1r,2r,4as,6as,6br,8ar,9r,10s,12as,12br,14bs)-10-{[(2s,3r,4s,5s)-3,5-dihydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C41H66O14 (782.4452)

methyl (1s,5s)-5-(3-hydroxy-1-methoxy-1-oxopropan-2-yl)-2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate

C12H18O6 (258.1103)

1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxopyridine-3-carboximidic acid

C11H14N2O6 (270.0852)

methyl 7-hydroxy-7-[(7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy)methyl]-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C33H46O20 (762.2582)

(4s)-3,5,5-trimethyl-4-({[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C16H26O7 (330.1678)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

C16H26O8 (346.1628)

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C41H66O14 (782.4452)

methyl 3-[12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-(6-methylhept-5-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoate

C31H50O3 (470.376)

(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carboxylic acid

C16H26O8 (346.1628)

(1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C16H24O10 (376.1369)

(4s)-3,5,5-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C16H26O7 (330.1678)

7,7,12,16-tetramethyl-15-(6-methyl-5-oxoheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O2 (440.3654)

3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}benzoic acid

C25H28O13 (536.153)

3-[(1r,3s,4s,8s,10r,11r,14s,15s)-11,15-dimethyl-14-[(2s,5e)-6-methyl-7-oxohept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoic acid

C30H42O5 (482.3032)

methyl 1,10-bis(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C35H54O6 (570.392)

methyl 4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

(1r,3as,3bs,7s,9bs)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H48O (400.3705)

methyl (1s,4as,7r,7as)-7-(hydroxymethyl)-7-methoxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C18H26O11 (418.1475)

(1s,3ar,3br,5as,9ar,9bs,11ar)-1-[(2s,5s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a-tetramethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-one

C29H48O3 (444.3603)

methyl (1s,7s,8r,9s,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

methyl 7-(hydroxymethyl)-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C26H30O13 (550.1686)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,2r,4as,6as,6br,8ar,9r,10s,12ar,12br,14br)-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C42H68O15 (812.4558)

(3ar,4s,7r)-1,4-dimethyl-7-(2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-3a,4,5,6,7,8-hexahydro-3h-azulen-2-one

C21H34O7 (398.2304)

methyl (1s,4s,7s,8s,9r,11s)-4,9-dihydroxy-2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undec-5-ene-8-carboxylate

C11H14O6 (242.079)

hexacosyl 3-(4-hydroxyphenyl)prop-2-enoate

C35H60O3 (528.4542)

2-[(2,6-dimethylhepta-1,5-dien-1-yl)oxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

C20H34O10 (434.2152)

3-[(1s,4r,5r,8s,9r,12r,13r)-12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[(2r)-6-methylhept-5-en-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

C30H48O3 (456.3603)

(2r,4as,6as,6br,8ar,10s,12ar,12br)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,7,8,8a,10,11,12,12b,13-dodecahydro-2h-picene-4a-carboxylic acid

C30H46O3 (454.3447)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1s,4ar,6as,6br,8ar,10s,12ar,12bs,14bs)-10-{[(2s,3r,4s,5s)-4,5-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C47H76O17 (912.5082)

8-hydroxy-3-(2-hydroxypropyl)-3,4-dihydro-2-benzopyran-1-one

C12H14O4 (222.0892)

[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-{[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]methoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

C27H36O11 (536.2258)

7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,8,8-trimethyl-5,6-dioxo-7h-1,11-dioxa-8-azatetracen-8-ium

[C30H36NO15]+ (650.2085)

methyl (1s,4as,7s,7as)-7-{[(1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy]methyl}-7-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C33H46O20 (762.2582)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,2r,4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C41H66O14 (782.4452)

3-[(1r,4s,5s,8r,9r,12s,13s)-12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[(2s)-6-methylhept-5-en-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

C30H48O3 (456.3603)

3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

C20H20O6 (356.126)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,2r,4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2s,3r,4s,5s)-3,5-dihydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C47H76O18 (928.5031)

(acetyloxy)[(3s,4r)-3-hydroxy-1h,3h,4h,5h,6h-cyclopenta[c]furan-4-yl]acetic acid

C11H14O6 (242.079)

(2r,3r,4s,5s,6r)-2-{[(1z)-2,6-dimethylhepta-1,5-dien-1-yl]oxy}-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C20H34O10 (434.2152)

3-{11,15-dimethyl-14-[1-(4-methylfuran-2-yl)propan-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl}propanoic acid

C30H40O5 (480.2876)

2-(3,5-dihydroxy-4-methoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one

C19H18O9 (390.0951)

(1s,3r,8s,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methyl-5-oxoheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O2 (440.3654)

methyl (1s,4as,7as)-1-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C32H40O18 (712.2215)

(12s,13r,18s)-8,12-dihydroxy-4,15-dimethyl-3,11-dioxa-15-azatetracyclo[8.8.0.0²,⁷.0¹³,¹⁸]octadeca-1,4,7,9-tetraene-6,14-dione

C17H17NO6 (331.1056)

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C42H68O15 (812.4558)

7-hydroxy-5-methoxychromen-4-one

C10H8O4 (192.0423)

methyl (1r,4as,7as)-7-(hydroxymethyl)-1-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O10 (388.1369)

methyl (4ar,7as)-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O10 (388.1369)

(4s,4as,7as)-4,7-bis(hydroxymethyl)-4-methyl-1h,4ah,5h,7ah-cyclopenta[c]pyran-3-one

C11H16O4 (212.1049)

methyl (1s,4ar)-7-oxo-1-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C16H20O10 (372.1056)

(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(acetyloxy)-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

C26H36O13 (556.2156)

(3r,3as,7ar)-3-ethoxy-7,7-dimethyl-hexahydro-2-benzofuran-5-one

C12H20O3 (212.1412)

5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one

C19H18O8 (374.1002)

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,7as)-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O8 (330.1315)

methyl 3-[11,15-dimethyl-14-(6-methylhept-5-en-2-yl)-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H46O4 (482.3396)

3-[(1s,3r,4r,8r,10s,11s,14r,15r)-11,15-dimethyl-14-[(2r)-6-methylhept-5-en-2-yl]-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoic acid

C30H44O4 (468.3239)

1,2,6b,9,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a,6a-dicarboxylic acid

C36H56O10 (648.3873)

3-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,3h,4h,4ah,7h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C16H24O11 (392.1319)

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1s,4ar,6as,6br,8ar,9r,10s,12ar,12br,14bs)-1-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C42H68O15 (812.4558)

(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2r)-6-methyl-4-oxohept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid

C30H46O5 (486.3345)

2,4,4-trimethyl-3-({[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C22H36O12 (492.2207)

(1r,2r,4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-{[(2s,3r,4s,5s)-3,5-dihydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C41H66O14 (782.4452)

methyl 10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1-oxo-4,5,6,7,8,8a,10,11,12,12b,13,14-dodecahydro-3h-picene-4a-carboxylate

C33H50O5 (526.3658)

(4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-{[(2r,3r,4s,5r,6r)-5-hydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C47H76O17 (912.5082)

(1s,2r,4as,6ar,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-1,2,6b,9,9,12a-hexamethyl-4a-({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-6a-carboxylic acid

C36H56O10 (648.3873)

methyl 1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C31H50O4 (486.3709)

ethyl 3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

C18H22O9 (382.1264)

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxychromen-4-one

C18H16O8 (360.0845)

bis[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

C44H64O24 (976.3787)

(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,2s,4as,6as,6bs,8as,10s,12as,12br,14br)-10-{[(2r,3s,4r,5s)-4,5-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C47H76O17 (912.5082)

(1s,3r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

C27H28O13 (560.153)

(1s,3r,8r,11r,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O (424.3705)

methyl 7-oxo-1-{[3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C24H28O14 (540.1479)

(1s,4as,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylic acid

C27H32O14 (580.1792)

(1s,3r,8r,11s,12s,15r,16r)-7,7,12,16-tetramethyl-15-[(2r,3z)-6-methylhepta-3,5-dien-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H46O (422.3548)

(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,6as,6br,8ar,10s,12ar,12bs,14bs)-10-{[(2r,3s,4r,5s)-4,5-dihydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

C47H76O17 (912.5082)

methyl (1s,4as,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C32H40O17 (696.2265)

methyl 1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

C23H34O15 (550.1898)

2,4,4-trimethyl-3-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]methoxy}cyclohex-2-en-1-one

C22H36O12 (492.2207)

3-(hydroxymethyl)-2,4,4-trimethylcyclohex-2-en-1-one

C10H16O2 (168.115)

methyl 7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7h,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O10 (388.1369)

methyl 3-[(1s,4r,5r,8s,9s,12r,13r)-12-(3-hydroxyprop-1-en-2-yl)-4,8-dimethyl-5-[(2r)-6-methylhept-5-en-2-yl]tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoate

C31H50O3 (470.376)

methyl 3-[14-(7-hydroxy-6-methylhept-5-en-2-yl)-11,15-dimethyl-5-methylidene-6-oxo-7-oxapentacyclo[8.7.0.0¹,³.0⁴,⁸.0¹¹,¹⁵]heptadecan-3-yl]propanoate

C31H46O5 (498.3345)

n-[2-(5-methoxy-1h-indol-3-yl)ethyl]ethanimidic acid

C13H16N2O2 (232.1212)

6-methoxy-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C16H18O9 (354.0951)

methyl (1s,4as,7s,7as)-7-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,7ah-cyclopenta[c]pyran-4-carboxylate

C17H24O11 (404.1319)