NCBI Taxonomy: 217501

Ligularia dentata (ncbi_taxid: 217501)

found 98 associated metabolites at species taxonomy rank level.

Ancestor: Ligularia

Child Taxonomies: Ligularia dentata subsp. sutchuenensis

Vanillin

Vanillin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material

C8H8O3 (152.0473)


Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Vanillin appears as white or very slightly yellow needles. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. Vanillin is a natural product found in Ficus erecta var. beecheyana, Pandanus utilis, and other organisms with data available. Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). Vanillin is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of vanilla (Vanilla subspecies) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent especies in cocoa products. obtained from spent wood-pulp liquors. Vanillin is found in many foods, some of which are pomes, elderberry, common cabbage, and dock. A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; ML_ID 59 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

Caffeic acid

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic 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).

   

Ferulic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic 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.

   

Lupeol

(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

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].

   

beta-Caryophyllene

trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene

C15H24 (204.1878)


beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. (-)-Caryophyllene. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-44-5 (retrieved 2024-08-07) (CAS RN: 87-44-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   
   

cis-Caffeic acid

(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid

C9H8O4 (180.0423)


Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g). D020011 - Protective Agents > D000975 - Antioxidants Found in olive oil, peanuts and other plant sources 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).

   

Methyl ferulate

Methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C11H12O4 (208.0736)


Methyl ferulate, also known as methyl ferulic acid, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Methyl ferulate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Methyl ferulate can be found in garden onion, which makes methyl ferulate a potential biomarker for the consumption of this food product. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2]. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2].

   

3-(4-Formylphenoxy)-4-methoxybenzaldehyde

3-(4-Formylphenoxy)-4-methoxybenzaldehyde

C15H12O4 (256.0736)


   

Methyl ferulate

(E)-Methyl-4-hydroxy-3-methoxycinnamate

C11H12O4 (208.0736)


Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2]. Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2].

   

Methyl indole-3-carboxylate

Methyl indole-3-carboxylate

C10H9NO2 (175.0633)


The methyl ester of indole-3-carboxylic acid. Methyl indole-3-carboxylate is a natural product isolated from Sorangium cellulosum strain Soce895. Methyl indole-3-carboxylate shows a weak activity against the Gram-positive Nocardia sp with a MIC value of 33.33 μg/mL[1]. Methyl indole-3-carboxylate is a natural product isolated from Sorangium cellulosum strain Soce895. Methyl indole-3-carboxylate shows a weak activity against the Gram-positive Nocardia sp with a MIC value of 33.33 μg/mL[1].

   

Vanillin

4-hydroxy-3-methoxybenzaldehyde

C8H8O3 (152.0473)


CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3579; ORIGINAL_PRECURSOR_SCAN_NO 3578 D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3566; ORIGINAL_PRECURSOR_SCAN_NO 3561 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3549; ORIGINAL_PRECURSOR_SCAN_NO 3546 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3560; ORIGINAL_PRECURSOR_SCAN_NO 3556 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3573; ORIGINAL_PRECURSOR_SCAN_NO 3570 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3577; ORIGINAL_PRECURSOR_SCAN_NO 3575 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.503 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

lupeol

Lup-20(29)-en-3.beta.-ol

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].

   

4-Methoxy[3,4-oxybisbenzaldehyde]

4-Methoxy[3,4-oxybisbenzaldehyde]

C15H12O4 (256.0736)


   

Butyrospermol

(3S,5R,10R,13S,14S)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-ol

C30H50O (426.3861)


(-)-Butyrospermol is a natural product found in Euphorbia chamaesyce, Euphorbia mellifera, and other organisms with data available.

   

Caffeate

(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0423)


D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID C107 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).

   

Caffeic Acid

3,4-dihydroxy cinnamic acid

C9H8O4 (180.0423)


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. 3,4-dihydroxycinnamic acid, also known as caffeic acid or trans-caffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3,4-dihydroxycinnamic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxycinnamic acid can be found in fats and oils and nuts, which makes 3,4-dihydroxycinnamic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxycinnamic acid exists in all eukaryotes, ranging from yeast to humans. Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal components of plant biomass and its residues . Caffeic acid 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) [HMDB]. Caffeic acid is found in many foods, some of which are cardoon, coriander, common persimmon, and irish moss. D020011 - Protective Agents > D000975 - Antioxidants Annotation level-2 CONFIDENCE standard compound; INTERNAL_ID 167 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.412 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.403 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).

   

ferulate

InChI=1\C10H10O4\c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13\h2-6,11H,1H3,(H,12,13

C10H10O4 (194.0579)


Ferulic acid, also known as 4-hydroxy-3-methoxycinnamic acid or 3-methoxy-4-hydroxy-trans-cinnamic acid, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid can be found in a number of food items such as flaxseed, pepper (c. chinense), chinese cinnamon, and wakame, which makes ferulic acid a potential biomarker for the consumption of these food products. Ferulic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and stratum corneum tissues. Ferulic acid exists in all eukaryotes, ranging from yeast to humans. Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis) . 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 (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.

   

Ferulic acid

4-hydroxy-3-methoxycinnamic 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.

   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.1878)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

AI3-63211

InChI=1\C9H8O4\c10-7-3-1-6(5-8(7)11)2-4-9(12)13\h1-5,10-11H,(H,12,13)\b4-2

C9H8O4 (180.0423)


D020011 - Protective Agents > D000975 - Antioxidants 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).

   

Zimco

InChI=1\C8H8O3\c1-11-8-4-6(5-9)2-3-7(8)10\h2-5,10H,1H

C8H8O3 (152.0473)


D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   
   

Butyrospermol

Butyrospermol

C30H50O (426.3861)


   

(1r,4e,6s,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4e,6s,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

(3s,5r)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5-hydroxy-6-methylhepta-1,6-dien-3-yl (2z)-2-methylbut-2-enoate

(3s,5r)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5-hydroxy-6-methylhepta-1,6-dien-3-yl (2z)-2-methylbut-2-enoate

C30H42O10 (562.2778)


   

1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

C14H18O (202.1358)


   

(1r,3'r,4r,6r,7s)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

(1r,3'r,4r,6r,7s)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

C21H29NO8 (423.1893)


   

4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

C31H46O11 (594.304)


   

(2s)-1-[(2r,3as,4r,7as)-7a-methoxy-6-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-7-oxo-3a,4-dihydro-2h-1-benzofuran-2-yl]-3-hydroxy-3-methylbutan-2-yl (2z)-2-methylbut-2-enoate

(2s)-1-[(2r,3as,4r,7as)-7a-methoxy-6-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-7-oxo-3a,4-dihydro-2h-1-benzofuran-2-yl]-3-hydroxy-3-methylbutan-2-yl (2z)-2-methylbut-2-enoate

C26H36O8 (476.241)


   

(1r,4z,6s,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4z,6s,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

β-sitostenone

NA

C29H48O (412.3705)


{"Ingredient_id": "HBIN018272","Ingredient_name": "\u03b2-sitostenone","Alias": "NA","Ingredient_formula": "C29H48O","Ingredient_Smile": "CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(=O)C4)C)C)C(C)C","Ingredient_weight": "NA","OB_score": "NA","CAS_id": "NA","SymMap_id": "NA","TCMID_id": "19965","TCMSP_id": "NA","TCM_ID_id": "NA","PubChem_id": "NA","DrugBank_id": "NA"}

   

7,9-dihydroxy-2-(2-hydroxypropan-2-yl)-8-methyl-5-methylidene-3,4-dihydro-2h-1-benzoxepin-4-yl 2-methylbut-2-enoate

7,9-dihydroxy-2-(2-hydroxypropan-2-yl)-8-methyl-5-methylidene-3,4-dihydro-2h-1-benzoxepin-4-yl 2-methylbut-2-enoate

C20H26O6 (362.1729)


   

(3s)-2-[(1e,5r)-3-(acetyloxy)-5-hydroxy-4-methyl-2-oxocyclohex-3-en-1-ylidene]-6-methylhept-5-en-3-yl (2z)-2-methylbut-2-enoate

(3s)-2-[(1e,5r)-3-(acetyloxy)-5-hydroxy-4-methyl-2-oxocyclohex-3-en-1-ylidene]-6-methylhept-5-en-3-yl (2z)-2-methylbut-2-enoate

C22H30O6 (390.2042)


   

(1s,6s,8as)-8a-(hydroxymethyl)-4-methyl-6-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalen-1-ol

(1s,6s,8as)-8a-(hydroxymethyl)-4-methyl-6-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalen-1-ol

C15H24O2 (236.1776)


   

4-ethenyl-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-dien-7-yl acetate

4-ethenyl-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-dien-7-yl acetate

C21H27NO7 (405.1787)


   

(1r,3'r,4s,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

(1r,3'r,4s,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

C21H29NO8 (423.1893)


   

(4r,4ar,7r)-4-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4r,4ar,7r)-4-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H22O2 (234.162)


   

methyl (2z,4e)-5-[(1s)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate

methyl (2z,4e)-5-[(1s)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate

C16H22O4 (278.1518)


   

methyl (2s,4s,5r)-5-(acetyloxy)-2-[(1r)-1-methoxyethyl]-4,5-dimethyl-6-oxooxane-2-carboxylate

methyl (2s,4s,5r)-5-(acetyloxy)-2-[(1r)-1-methoxyethyl]-4,5-dimethyl-6-oxooxane-2-carboxylate

C14H22O7 (302.1365)


   

(3as,5ar,7s,9ar,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(3as,5ar,7s,9ar,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H50O (426.3861)


   

methyl (2s,3r,5e)-5-ethylidene-2,3-dimethyl-6-oxooxane-2-carboxylate

methyl (2s,3r,5e)-5-ethylidene-2,3-dimethyl-6-oxooxane-2-carboxylate

C11H16O4 (212.1049)


   

methyl 5-(acetyloxy)-2-(1-methoxyethyl)-4,5-dimethyl-6-oxooxane-2-carboxylate

methyl 5-(acetyloxy)-2-(1-methoxyethyl)-4,5-dimethyl-6-oxooxane-2-carboxylate

C14H22O7 (302.1365)


   

5-hydroxy-2-{4-hydroxy-6-methyl-2-[(2-methylbut-2-enoyl)oxy]-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl}-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

5-hydroxy-2-{4-hydroxy-6-methyl-2-[(2-methylbut-2-enoyl)oxy]-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl}-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

C26H38O9 (494.2516)


   

(3r,5r)-2-(2,3-dihydroxy-4-methylphenyl)-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

(3r,5r)-2-(2,3-dihydroxy-4-methylphenyl)-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

C21H30O6 (378.2042)


   

(1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

(1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

C29H46O2 (426.3498)


   

3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

C21H29NO8 (423.1893)


   

methyl 5-ethylidene-2,3-dimethyl-6-oxooxane-2-carboxylate

methyl 5-ethylidene-2,3-dimethyl-6-oxooxane-2-carboxylate

C11H16O4 (212.1049)


   

(2r,3s,5s)-2-(2,3-dihydroxy-4-methylphenyl)-5-(2-methoxypropan-2-yl)-2-methyloxolan-3-yl (2z)-2-methylbut-2-enoate

(2r,3s,5s)-2-(2,3-dihydroxy-4-methylphenyl)-5-(2-methoxypropan-2-yl)-2-methyloxolan-3-yl (2z)-2-methylbut-2-enoate

C21H30O6 (378.2042)


   

3-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

3-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

C30H42O10 (562.2778)


   

(1r,4e,6s,7r,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4e,6s,7r,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

(1r,4z,6r,7s,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

(1r,4z,6r,7s,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

C18H27NO5 (337.1889)


   

(1r,3'r,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

(1r,3'r,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

C21H29NO8 (423.1893)


   

(1r,11r)-6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

(1r,11r)-6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

C14H14O3 (230.0943)


   

(2s)-3-[(1r,2r,3r,4s,6s)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate

(2s)-3-[(1r,2r,3r,4s,6s)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-1-[(2s)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate

C30H42O10 (562.2778)


   

(2s)-3-[(1s,2s,3s,4r,6r)-3,4-dihydroxy-4-methyl-2,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-1-[(2r)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate

(2s)-3-[(1s,2s,3s,4r,6r)-3,4-dihydroxy-4-methyl-2,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-1-[(2r)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl (2z)-2-methylbut-2-enoate

C30H42O10 (562.2778)


   

(11s,13r)-8-hydroxy-11-(2-hydroxypropan-2-yl)-7-methyl-14-methylidene-10-oxa-3-thia-5-azatricyclo[7.5.0.0²,⁶]tetradeca-1,4,6,8-tetraen-13-yl (2z)-2-methylbut-2-enoate

(11s,13r)-8-hydroxy-11-(2-hydroxypropan-2-yl)-7-methyl-14-methylidene-10-oxa-3-thia-5-azatricyclo[7.5.0.0²,⁶]tetradeca-1,4,6,8-tetraen-13-yl (2z)-2-methylbut-2-enoate

C21H25NO5S (403.1453)


   

(2s,4r)-7,9-dihydroxy-2-(2-hydroxypropan-2-yl)-8-methyl-5-methylidene-3,4-dihydro-2h-1-benzoxepin-4-yl (2z)-2-methylbut-2-enoate

(2s,4r)-7,9-dihydroxy-2-(2-hydroxypropan-2-yl)-8-methyl-5-methylidene-3,4-dihydro-2h-1-benzoxepin-4-yl (2z)-2-methylbut-2-enoate

C20H26O6 (362.1729)


   

methyl 2-(4-ethyl-2-methyl-5-oxooxolan-2-yl)-2-hydroxypropanoate

methyl 2-(4-ethyl-2-methyl-5-oxooxolan-2-yl)-2-hydroxypropanoate

C11H18O5 (230.1154)


   

(1r,4e,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

(1r,4e,7r,11s,17r)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

C18H27NO5 (337.1889)


   

1-{7a-methoxy-6-methyl-4-[(2-methylbut-2-enoyl)oxy]-3-methylidene-7-oxo-3a,4-dihydro-2h-1-benzofuran-2-yl}-3-hydroxy-3-methylbutan-2-yl 2-methylbut-2-enoate

1-{7a-methoxy-6-methyl-4-[(2-methylbut-2-enoyl)oxy]-3-methylidene-7-oxo-3a,4-dihydro-2h-1-benzofuran-2-yl}-3-hydroxy-3-methylbutan-2-yl 2-methylbut-2-enoate

C26H36O8 (476.241)


   

ethyl (7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

ethyl (7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

C16H20O3 (260.1412)


   

4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

C18H27NO5 (337.1889)


   

3-{3,4-dihydroxy-4-methyl-2,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

3-{3,4-dihydroxy-4-methyl-2,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

C30H42O10 (562.2778)


   

(1r,3'r,4r,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

(1r,3'r,4r,6r,7s,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

C21H29NO8 (423.1893)


   

(1r,4z,6r,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4z,6r,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

(3s,5s)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5,6-dihydroxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

(3s,5s)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5,6-dihydroxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

C30H44O11 (580.2883)


   

methyl 3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

methyl 3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

C15H18O3 (246.1256)


   

(3r,5r)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

(3r,5r)-2-[(1s,2s,3s,4r,6r)-2,4-dihydroxy-4-methyl-3,6-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxocyclohexyl]-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

C31H46O11 (594.304)


   

(1r,3ar,7s,9ar,11ar)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,7s,9ar,11ar)-3a,6,6,9a,11a-pentamethyl-1-[(2r)-6-methylhept-5-en-2-yl]-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H50O (426.3861)


   

(3s)-6-hydroxy-5-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

(3s)-6-hydroxy-5-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

C14H16O2 (216.115)


   

(1r,4e,6r,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4e,6r,7s,11z)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbaldehyde

3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbaldehyde

C14H16O2 (216.115)


   

2-(2,3-dihydroxy-4-methylphenyl)-5-(2-methoxypropan-2-yl)-2-methyloxolan-3-yl 2-methylbut-2-enoate

2-(2,3-dihydroxy-4-methylphenyl)-5-(2-methoxypropan-2-yl)-2-methyloxolan-3-yl 2-methylbut-2-enoate

C21H30O6 (378.2042)


   

2-(2,3-dihydroxy-4-methylphenyl)-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

2-(2,3-dihydroxy-4-methylphenyl)-5-hydroxy-6-methoxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

C21H30O6 (378.2042)


   

5-hydroxy-6-methoxy-6-methyl-2-[(1r,3r,4r,6r)-6-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]hept-1-en-3-yl (2z)-2-methylbut-2-enoate

5-hydroxy-6-methoxy-6-methyl-2-[(1r,3r,4r,6r)-6-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]hept-1-en-3-yl (2z)-2-methylbut-2-enoate

C26H38O8 (478.2567)


   

(1r,4e,6s,7r)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4e,6s,7r)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

(3s)-6-hydroxy-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

(3s)-6-hydroxy-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

C13H14O2 (202.0994)


   

2-[3-(acetyloxy)-5-hydroxy-4-methyl-2-oxocyclohex-3-en-1-ylidene]-6-methylhept-5-en-3-yl 2-methylbut-2-enoate

2-[3-(acetyloxy)-5-hydroxy-4-methyl-2-oxocyclohex-3-en-1-ylidene]-6-methylhept-5-en-3-yl 2-methylbut-2-enoate

C22H30O6 (390.2042)


   

(3r,5r)-5-hydroxy-2-[(1r,2s,3r,4r,6r)-4-hydroxy-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

(3r,5r)-5-hydroxy-2-[(1r,2s,3r,4r,6r)-4-hydroxy-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methoxy-6-methylhept-1-en-3-yl (2z)-2-methylbut-2-enoate

C26H38O9 (494.2516)


   

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5-hydroxy-6-methylhepta-1,6-dien-3-yl 2-methylbut-2-enoate

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5-hydroxy-6-methylhepta-1,6-dien-3-yl 2-methylbut-2-enoate

C30H42O10 (562.2778)


   

4-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

4-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H22O2 (234.162)


   

(4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium

(4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium

[C21H28NO7]+ (406.1866)


   

(1s,11s)-6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

(1s,11s)-6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

C14H14O3 (230.0943)


   

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5,6-dihydroxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

2-{2,4-dihydroxy-4-methyl-3,6-bis[(2-methylbut-2-enoyl)oxy]-5-oxocyclohexyl}-5,6-dihydroxy-6-methylhept-1-en-3-yl 2-methylbut-2-enoate

C30H44O11 (580.2883)


   

8-hydroxy-11-(2-hydroxypropan-2-yl)-7-methyl-14-methylidene-10-oxa-3-thia-5-azatricyclo[7.5.0.0²,⁶]tetradeca-1,4,6,8-tetraen-13-yl 2-methylbut-2-enoate

8-hydroxy-11-(2-hydroxypropan-2-yl)-7-methyl-14-methylidene-10-oxa-3-thia-5-azatricyclo[7.5.0.0²,⁶]tetradeca-1,4,6,8-tetraen-13-yl 2-methylbut-2-enoate

C21H25NO5S (403.1453)


   

8a-(hydroxymethyl)-4-methyl-6-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalen-1-ol

8a-(hydroxymethyl)-4-methyl-6-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalen-1-ol

C15H24O2 (236.1776)


   

methyl (2s)-2-[(2r,4r)-4-ethyl-2-methyl-5-oxooxolan-2-yl]-2-hydroxypropanoate

methyl (2s)-2-[(2r,4r)-4-ethyl-2-methyl-5-oxooxolan-2-yl]-2-hydroxypropanoate

C11H18O5 (230.1154)


   

(1r,4z,6s,7s)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

(1r,4z,6s,7s)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

C21H29NO7 (407.1944)


   

(7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbaldehyde

(7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbaldehyde

C14H16O2 (216.115)


   

6-hydroxy-5-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

6-hydroxy-5-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-naphthalen-1-one

C14H16O2 (216.115)


   

6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

6-hydroxy-11-(prop-1-en-2-yl)-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-3-one

C14H14O3 (230.0943)


   

(1s,4z,6r,7r,17r)-7-(acetyloxy)-4-ethenyl-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium-17-olate

(1s,4z,6r,7r,17r)-7-(acetyloxy)-4-ethenyl-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium-17-olate

C21H27NO7 (405.1787)


   

5,6-dihydroxy-6-methyl-2-[(1r,2r,3s,4r,6r)-6-methyl-2,4-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]hept-1-en-3-yl (2z)-2-methylbut-2-enoate

5,6-dihydroxy-6-methyl-2-[(1r,2r,3s,4r,6r)-6-methyl-2,4-bis({[(2z)-2-methylbut-2-enoyl]oxy})-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]hept-1-en-3-yl (2z)-2-methylbut-2-enoate

C30H42O10 (562.2778)


   

methyl (7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

methyl (7r)-3-hydroxy-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxylate

C15H18O3 (246.1256)


   

(4e)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

(4e)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadecane-3,8-dione

C18H27NO5 (337.1889)


   

(7r)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

(7r)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

C14H18O (202.1358)