Vanillic acid

4-hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


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].

   

Coniferaldehyde

(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal

C10H10O3 (178.062991)


Coniferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, 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. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223). Coniferyl aldehyde, also known as 4-hydroxy-3-methoxycinnamaldehyde or 4-hm-ca, 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. Coniferyl aldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Coniferyl aldehyde can be found in a number of food items such as pear, common walnut, kelp, and citrus, which makes coniferyl aldehyde a potential biomarker for the consumption of these food products. Coniferyl aldehyde is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine . Coniferyl aldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamaldehyde. 4-Hydroxy-3-methoxycinnamaldehyde is a natural product found in Pandanus utilis, Microtropis japonica, and other organisms with data available. A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. Acquisition and generation of the data is financially supported in part by CREST/JST. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells Coniferaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=458-36-6 (retrieved 2024-09-04) (CAS RN: 458-36-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Salicylic acid

2-hydroxybenzoic acid

C7H6O3 (138.0316926)


Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. It is a conjugate acid of a salicylate. It is a colorless solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone. The name is from Latin salix for willow tree. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates. Salicylic acid modulates COX1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation. Salicylates antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis. Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana, it can be synthesized via a phenylalanine-independent pathway. Salicylic acid is an odorless white to light tan solid. Sinks and mixes slowly with water. (USCG, 1999) Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. It is a conjugate acid of a salicylate. A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. Salicylic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Salicylic Acid is a beta hydroxy acid that occurs as a natural compound in plants. It has direct activity as an anti-inflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation. A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. A compound obtained from the bark of the white willow and wintergreen leaves. It has bacteriostatic, fungicidal, and keratolytic actions. See also: Benzoic Acid (has active moiety); Methyl Salicylate (active moiety of); Benzyl salicylate (is active moiety of) ... View More ... A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. Salicylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=69-72-7 (retrieved 2024-06-29) (CAS RN: 69-72-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Salicylic acid (2-Hydroxybenzoic acid) inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation[1]. Salicylic acid (2-Hydroxybenzoic acid) inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation[1].

   

L-Leucine

(2S)-2-amino-4-methylpentanoic acid

C6H13NO2 (131.0946238)


Leucine (Leu) or L-leucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-leucine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Leucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Leucine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. Leucine is the most important ketogenic amino acid in humans. The vast majority of l-leucine metabolism is initially catalyzed by the branched-chain amino acid aminotransferase enzyme, producing alpha-ketoisocaproate (alpha-KIC). alpha-KIC is metabolized by the mitochondrial enzyme branched-chain alpha-ketoacid dehydrogenase, which converts it to isovaleryl-CoA. Isovaleryl-CoA is subsequently metabolized by the enzyme isovaleryl-CoA dehydrogenase and converted to beta-methylcrotonyl-CoA (MC-CoA), which is used in the synthesis of acetyl-CoA and other compounds. During biotin deficiency, HMB can be synthesized from MC-CoA via enoyl-CoA hydratase and an unknown thioesterase enzyme, which convert MC-CoA into HMB-CoA and HMB-CoA into HMB respectively. Leucine has the capacity to directly stimulate myofibrillar muscle protein synthesis (PMID 15051860). This effect of leucine arises results from its role as an activator of the mechanistic target of rapamycin (mTOR) (PMID 23551944) a serine-threonine protein kinase that regulates protein biosynthesis and cell growth. The activation of mTOR by leucine is mediated through Rag GTPases. Leucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of leucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). BCAAs such as leucine have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Persistently low leucine levels can result in decreased appetite, poor feeding, lethargy, poor growth, weight loss, skin rashes, hair loss, and desquamation. Many types of inborn errors of BCAA metabolism exist and these are marked by various abnormalities. The most common form is maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary res... L-leucine is the L-enantiomer of leucine. It has a role as a plant metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a leucine and a L-alpha-amino acid. It is a conjugate base of a L-leucinium. It is a conjugate acid of a L-leucinate. It is an enantiomer of a D-leucine. It is a tautomer of a L-leucine zwitterion. An essential branched-chain amino acid important for hemoglobin formation. L-Leucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Leucine is one of nine essential amino acids in humans (provided by food), Leucine is important for protein synthesis and many metabolic functions. Leucine contributes to regulation of blood-sugar levels; growth and repair of muscle and bone tissue; growth hormone production; and wound healing. Leucine also prevents breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. Leucine is available in many foods and deficiency is rare. (NCI04) Leucine (abbreviated as Leu or L)[2] is a branched-chain л±-amino acid with the chemical formulaHO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin, and other buffer proteins. Leucine is an essential amino acid, meaning that the human body cannot synthesize it, and it therefore must be ingested. It is important for hemoglobin formation. An essential branched-chain amino acid important for hemoglobin formation. See also: Isoleucine; Leucine (component of) ... View More ... Dietary supplement, nutrient [DFC]. (±)-Leucine is found in many foods, some of which are green bell pepper, italian sweet red pepper, green zucchini, and red bell pepper. L-Leucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=61-90-5 (retrieved 2024-07-01) (CAS RN: 61-90-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

   

Ferulic acid

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

C10H10O4 (194.057906)


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.

   

Pinoresinol

PHENOL, 4,4-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-, (1S-(1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.))-

C20H22O6 (358.1416312)


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].

   

Afzelin

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C21H20O10 (432.105642)


Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. [Raw Data] CBA27_Afzelin_neg_30eV_1-1_01_1585.txt [Raw Data] CBA27_Afzelin_pos_20eV_1-1_01_1549.txt [Raw Data] CBA27_Afzelin_pos_10eV_1-1_01_1540.txt [Raw Data] CBA27_Afzelin_neg_10eV_1-1_01_1576.txt [Raw Data] CBA27_Afzelin_neg_20eV_1-1_01_1584.txt [Raw Data] CBA27_Afzelin_neg_40eV_1-1_01_1586.txt [Raw Data] CBA27_Afzelin_pos_30eV_1-1_01_1550.txt [Raw Data] CBA27_Afzelin_pos_50eV_1-1_01_1552.txt [Raw Data] CBA27_Afzelin_pos_40eV_1-1_01_1551.txt [Raw Data] CBA27_Afzelin_neg_50eV_1-1_01_1587.txt Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

Stigmastanol

(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H52O (416.4017942)


Stigmastanol is a 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. It has a role as an anticholesteremic drug and a plant metabolite. It is a 3-hydroxy steroid and a member of phytosterols. It derives from a hydride of a 5alpha-stigmastane. Stigmastanol is a natural product found in Alnus japonica, Dracaena cinnabari, and other organisms with data available. Stigmastanol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and a saturated bond in position 5-6 of the B ring. See also: Saw Palmetto (part of). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents C1907 - Drug, Natural Product > C28178 - Phytosterol > C68422 - Saturated Phytosterol D009676 - Noxae > D000963 - Antimetabolites Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2]. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].

   

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715156)


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.

   

Delphinidin 3-glucoside

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

[C21H21O12]+ (465.1032966)


Delphinidin 3-glucoside is found in adzuki bean. Delphinidin 3-glucoside is isolated from grapes and many other plant species Delphinidin 3-glucoside is present in red wine. Delphinidin 3-glucoside is isolated from grapes and many other plant spp. It is found in red wine, redcurrant, summer grape, strawberry, and green bean. Acquisition and generation of the data is financially supported in part by CREST/JST.

   

Cyanidin 3-glucoside

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

[C21H21O11]+ (449.10838160000003)


Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Acquisition and generation of the data is financially supported in part by CREST/JST. Found in many plants and fruits, e.g. cherries, olives and grapes

   

Dehydroabietic acid

(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

C20H28O2 (300.2089188)


Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

   

Benzyl alcohol

Hydroxymethylpolystyrene resin

C7H8O (108.0575118)


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.

   

gamma-Humulene

(1E,6Z)-1,8,8-trimethyl-5-methylidenecycloundeca-1,6-diene (1E,6Z)-humula-1(11),4(13),5-triene

C15H24 (204.18779039999998)


   

Himachalol

1H-Benzocyclohepten-9-ol, 2,4a-.beta.,5,6,7,8,9,9a-.beta.-octahydro-3,5,5,9-.beta.-tetramethyl-

C15H26O (222.1983546)


   

Juvabione

(+)-Juvabione

C16H26O3 (266.1881846)


   

fenchone

(1R,4S)-(+)-fenchone;(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

C10H16O (152.12010859999998)


A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare). Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

   

Dihydroconiferyl alcohol

3-(4-hydroxy-3-methoxyphenyl)-propan-1-ol

C10H14O3 (182.0942894)


Dihydroconiferyl alcohol, also known as 3-(4-guaiacyl)propanol or 3-(4-hydroxy-3-methoxyphenyl)-propan-1-ol, 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. Dihydroconiferyl alcohol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Dihydroconiferyl alcohol can be found in lettuce and romaine lettuce, which makes dihydroconiferyl alcohol a potential biomarker for the consumption of these food products. Dihydroconiferyl alcohol is a cell division factor that can be found in pring sap of Acer pseudoplatanus L. Dihydroconiferyl alcohol can stimulate growth of soybean callus[1].

   

3',4'-Dihydroxyacetophenone

1-(3,4-Dihydroxyphenyl)ethanone, 9CI

C8H8O3 (152.0473418)


3,4-Dihydroxyacetophenone is found in coffee and coffee products. 3,4-Dihydroxyacetophenone is extracted from coffee residues. Potential component of FEMA 3662. 3,4-Dihydroxyacetophenone is a mixture of dihydroxyacetophenone isomers is used in food flavourin D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents 3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2]. 3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2].

   

Levopimaric acid

.DELTA.6,8(14)-Abietadienoic acid

C20H30O2 (302.224568)


Origin: Plant; SubCategory_DNP: Diterpenoids, Pimarine diterpenoids

   

Neoabietic acid

Podocarp-8(14)-en-15-oic acid, 13-isopropylidene-

C20H30O2 (302.224568)


   

8,13-Abietadien-18-al

1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,9,10,10a-decahydrophenanthrene-1-carbaldehyde

C20H30O (286.229653)


8,13-Abietadien-18-al is found in fruits. 8,13-Abietadien-18-al is isolated from Pinus koraiensis (Korean pine) and other conifers. Isolated from Pinus koraiensis (Korean pine) and other conifers. 8,13-Abietadien-18-al is found in herbs and spices and fruits.

   

Fenchyl acetate

(1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl acetic acid

C12H20O2 (196.14632200000003)


(-)-alpha-Fenchyl acetate is a flavouring ingredient, together with stereoisomers. Flavouring ingredient, together with stereoisomers Same as: D09740

   

Pinoresinol

Phenol,4-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2-methoxy-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-

C20H22O6 (358.1416312)


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].

   

Petunidin 3-galactoside

2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

C22H23O12+ (479.1189458)


Pigment from whortleberry, blackberry, etc. Petunidin 3-galactoside is found in many foods, some of which are common grape, bilberry, black chokeberry, and sweet cherry. Petunidin 3-galactoside is found in american cranberry. Petunidin 3-galactoside is a pigment from whortleberry, blackberry, etc.

   

Floribundoside

7-hydroxy-2-(4-hydroxyphenyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

C21H22O10 (434.1212912)


Floribundoside is found in fruits. Floribundoside occurs in Persica vulgaris (peach). Occurs in Persica vulgaris (peach). Naringenin 5-glucoside is found in fruits.

   

7-Ketocholesterol

(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

C27H44O2 (400.3341124)


7-Ketocholesterol is a major oxidation product of cholesterol (oxysterol) found in human atherosclerotic plaque and is more atherogenic than cholesterol in some animal studies. Oxysterols (oxygenated forms of cholesterol) are present at low levels in the circulation and accumulate is plasma and tissues in some pathologies. In atherosclerotic lesions, 7-oxygenated oxysterols, predominantly 7-ketocholesterol, accumulate and have been implicated in the pathology of the disease. There is some in vivo and in vitro evidence that sterol 27-hydroxylase acts on 7-ketocholesterol to initiate its degradation to more polar, water-soluble products. Recent studies indicate an alternative mechanism, in which 7-ketocholesterol is reduced to 7 beta-hydroxycholesterol by 11 beta-hydroxysteroid dehydrogenase type 1. 7-Ketocholesterol can inhibit cholesterol 7 alpha-hydroxylase, the rate-limiting step in bile acid biosynthesis, as well as strongly inhibiting HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis. It has even been suggested that 7-ketocholesterol is formed enzymically as an endogenous regulator of cholesterol biosynthesis. However, when tested as a pharmacological cholesterol-lowering agent, inhibition of HMG-CoA reductase was rapidly overcome and the 7-ketocholesterol metabolised. In vitro, 7-ketocholesterol has wide-ranging and potent effects, most of which have the potential to contribute to atherosclerosis. For example, 7-ketocholesterol can be cytotoxic and can induce apoptosis in vascular cells. These effects, either individually or more likely, in combination, all implicate 7-ketocholesterol in the initiation and development of atherosclerosis, but further work is needed to establish whether or not its role is a direct causal one. 7-Ketocholesterol is the second most abundant oxysterol found in human atherosclerotic plaque, after the enzymically formed 27-hydroxycholesterol (cholest-5-ene-3beta,27-diol). 7-Ketocholesterol differs from cholesterol by a ketone functional group present at the 7-position. It is produced from cholesterol via the epimeric cholesterol 7-hydroperoxides (cholest-5-ene-3beta-ol-7-hydroperoxide) which decompose to the epimeric 7-hydroxycholesterols (cholest-5-ene-3beta,7-diol) and 7-ketocholesterol. 7-Ketocholesterol is a major dietary oxysterol. It has also been widely suggested that 7-ketocholesterol present in atherosclerotic tissue may be derived from the diet. Certainly, 7-ketocholesterol is a major oxysterol found in cholesterol-rich processed foodstuffs. Dietary 7-ketocholesterol is rapidly metabolised by the liver to 7beta-hydroxycholesterol (cholest-5-ene-3beta,7beta-diol), unusual bile acids and perhaps even cholesterol itself. Its conversion to 7beta-hydroxycholesterol is well documented. (PMID: 15798369, 10224662). 7-Ketocholesterol is a major oxidation product of cholesterol (oxysterol) found in human atherosclerotic plaque and is more atherogenic than cholesterol in some animal studies. Oxysterols (oxygenated forms of cholesterol) are present at low levels in the circulation and accumulate is plasma and tissues in some pathologies. In atherosclerotic lesions, 7-oxygenated oxysterols, predominantly 7-ketocholesterol, accumulate and have been implicated in the pathology of the disease. There is some in vivo and in vitro evidence that sterol 27-hydroxylase acts on 7-ketocholesterol to initiate its degradation to more polar, water-soluble products. Recent studies indicate an alternative mechanism, in which 7-ketocholesterol is reduced to 7 beta-hydroxycholesterol by 11 beta-hydroxysteroid dehydrogenase type 1. 7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].

   

(-)-Borneol

1,7,7-Trimethyl-(1R,2S,4R)-rel-bicyclo[2.2.1]heptan-2-ol

C10H18O (154.1357578)


(-)-Borneol is found in common thyme and in turmeric. (-)-Borneol is a constituent of Blumea balsamifera (sambong). Both Borneol and Isoborneol and their acetates and formates are used as flavouring agents Constituent of Blumea balsamifera (sambong). (-)-Borneol is found in many foods, some of which are tea, coriander, common thyme, and cornmint. 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].

   

N-Heptane

N-Heptane, ion (1+)

C7H16 (100.1251936)


N-Heptane, also known as heptan or CH3-[CH2]5-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, N-heptane is considered to be a hydrocarbon lipid molecule. N-Heptane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. N-Heptane is a sweet, alkane, and ethereal tasting compound. N-heptane has been detected, but not quantified, in cardamoms and gingers. This could make N-heptane a potential biomarker for the consumption of these foods. This is done by shaking the stained paper in a heptane solution for about half a minute. N-Heptane is a potentially toxic compound. It was originally chosen as the zero point of the scale because of the availability of very high purity n-heptane, unmixed with other isomers of heptane or other alkanes, distilled from the resin of Jeffrey pine and from the fruit of Pittosporum resiniferum. As a liquid, it is ideal for transport and storage. The 2,2-dimethylpentane isomer can be prepared by reacting tert-butyl chloride with n-propyl magnesium bromide. The linear n-heptane can be obtained from Jeffrey pine oil. In water, both bromine and iodine appear brown. n-Heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. Heptane is an alkane hydrocarbon with the chemical formula CH3(CH2)8CH3. Heptane has 9 isomers, or 11 if enantiomers are counted. N-Heptane is found in cardamom and ginger.

   

4-(3-hydroxybutyl)-2-methoxyphenol

4-(3-hydroxybutyl)-2-methoxyphenol

C11H16O3 (196.1099386)


   

Abietic acid

1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid

C20H30O2 (302.224568)


   

Afzelin

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

C21H20O10 (432.105642)


5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

Epipinoresinol

4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol

C20H22O6 (358.1416312)


(+)-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].

   

alpha-Himachalene

3,5,5-trimethyl-9-methylidene-2,4a,5,6,7,8,9,9a-octahydro-1H-benzo[7]annulene

C15H24 (204.18779039999998)


Alpha-himachalene is a member of the class of compounds known as himachalane and lippifoliane sesquiterpenoids. Himachalane and lippifoliane sesquiterpenoids are diterpenoids with a structure based on either the himachalane or the lippifoliane skeleton. Alpha-himachalene can be found in anise and common oregano, which makes alpha-himachalene a potential biomarker for the consumption of these food products.

   

alpha-Fenchyl acetate

1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate

C12H20O2 (196.14632200000003)


Fenchyl acetate, also known as fenchyl acetic acid, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fenchyl acetate is a sweet, citrus, and fir tasting compound found in sweet basil, which makes fenchyl acetate a potential biomarker for the consumption of this food product.

   

D-Camphor

1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one

C10H16O (152.12010859999998)


(+)-camphor, also known as formosa camphor or 2-bornanone, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-camphor is considered to be an isoprenoid lipid molecule (+)-camphor is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-camphor is a bitter, camphor, and herbal tasting compound and can be found in a number of food items such as sugar apple, sunflower, fennel, and cardamom, which makes (+)-camphor a potential biomarker for the consumption of these food products. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2]. Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2].

   

Piceatannol

4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

C14H12O4 (244.0735552)


Piceatannol, also known as (Z)-3,5,3,4-tetrahydroxystilbene, is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Piceatannol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Piceatannol can be synthesized from cis-stilbene. Piceatannol can also be synthesized into cis-astringin. Piceatannol can be found in common grape and grape wine, which makes piceatannol a potential biomarker for the consumption of these food products. Piceatannol is a stilbenoid, a type of phenolic compound .

   

Dehydroabietic acid

InChI=1/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s

C20H28O2 (300.2089188)


Dehydroabietic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. It has a role as a metabolite and an allergen. It is an abietane diterpenoid, a monocarboxylic acid and a carbotricyclic compound. It is functionally related to an abietic acid. It is a conjugate acid of a dehydroabietate. Dehydroabietic acid is a natural product found in Nostoc, Relhania corymbosa, and other organisms with data available. Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

   

alpha-Fenchyl acetate

1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate

C12H20O2 (196.14632200000003)


Fenchyl acetate, also known as fenchyl acetic acid, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fenchyl acetate is a sweet, citrus, and fir tasting compound found in sweet basil, which makes fenchyl acetate a potential biomarker for the consumption of this food product.

   

Abietic acid

7,13-Abietadien-18-oic acid

C20H30O2 (302.224568)


Abietic acid, a diterpene isolated from Colophony, possesses antiproliferative, antibacterial, and anti-obesity properties. Abietic acid inhibits lipoxygenase activity for allergy treatment[1][2]. Abietic acid, a diterpene isolated from Colophony, possesses antiproliferative, antibacterial, and anti-obesity properties. Abietic acid inhibits lipoxygenase activity for allergy treatment[1][2].

   

Afzelin

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C21H20O10 (432.105642)


Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. Acquisition and generation of the data is financially supported in part by CREST/JST. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

3,3-DIMETHYLPENTANE

3,3-DIMETHYLPENTANE

C7H16 (100.1251936)


   

3',4'-Dihydroxyacetophenone

3 inverted exclamation mark ,4 inverted exclamation mark -Dihydroxyacetophenone

C8H8O3 (152.0473418)


3,4-Dihydroxyacetophenone is found in coffee and coffee products. 3,4-Dihydroxyacetophenone is extracted from coffee residues. Potential component of FEMA 3662. 3,4-Dihydroxyacetophenone is a mixture of dihydroxyacetophenone isomers is used in food flavourin 3,4-dihydroxyacetophenone is a member of acetophenones. It has a role as a metabolite. 3,4-Dihydroxyacetophenone is a natural product found in Vincetoxicum atratum, Picea obovata, and other organisms with data available. D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents 3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2]. 3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2].

   

Stigmastanol

(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H52O (416.4017942)


Stigmastanol is a 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. It has a role as an anticholesteremic drug and a plant metabolite. It is a 3-hydroxy steroid and a member of phytosterols. It derives from a hydride of a 5alpha-stigmastane. Stigmastanol is a natural product found in Alnus japonica, Dracaena cinnabari, and other organisms with data available. Stigmastanol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and a saturated bond in position 5-6 of the B ring. See also: Saw Palmetto (part of). A 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents C1907 - Drug, Natural Product > C28178 - Phytosterol > C68422 - Saturated Phytosterol D009676 - Noxae > D000963 - Antimetabolites 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. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2]. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].

   

benzyl alcohol

benzyl alcohol

C7H8O (108.0575118)


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.

   

Ferulic acid

4-hydroxy-3-methoxycinnamic acid

C10H10O4 (194.057906)


(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.

   

L-Leucine

L-Leucine, (Cell Culture Reagent, Crystalline)

C6H13NO2 (131.0946238)


Flavouring ingredient; dietary supplement, nutrient. L-Leucine is found in many foods, some of which are lettuce, common bean, pacific herring, and kefir. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ROHFNLRQFUQHCH-YFKPBYRVSA-N_STSL_0102_Leucine_8000fmol_180425_S2_LC02_MS02_19; 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 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. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

   

Catechol

(+)-Catechin Hydrate

C15H14O6 (290.0790344)


Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

Vanillic Acid

Vanillic acid hexoside

C8H8O4 (168.0422568)


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

stearic acid

C18H36O2 (284.2715156)


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.

   

Dehydroabietic acid

(+)-Dehydroabietic acid

C20H28O2 (300.2089188)


Origin: Plant; SubCategory_DNP: Diterpenoids, Abietane diterpenoids

   

7-KETOCHOLESTEROL

7-oxo-cholest-5-en-3beta-ol

C27H44O2 (400.3341124)


A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7. D004791 - Enzyme Inhibitors 7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].

   

Piceatannol

1,2-Benzenediol, {4-[2-(3,} 5-dihydroxyphenyl)ethenyl]-, (E)-

C14H12O4 (244.0735552)


C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor Piceatannol is a well-known Syk inhibitor and reduces the expression of iNOS induced by TNF. Piceatannol is an effective agent for research of acute lung injury (ALI)[1]. Piceatannol is a naturally occurring polyphenolic stilbene found in various fruits and vegetables and exhibits anticancer and anti-inflammatory properties[2]. Piceatannol induces apoptosis in DLBCL cell lines[3]. Piceatannol induces autophagy and apoptosis in MOLT-4 human leukemia cells[4]. Piceatannol is a well-known Syk inhibitor and reduces the expression of iNOS induced by TNF. Piceatannol is an effective agent for research of acute lung injury (ALI)[1]. Piceatannol is a naturally occurring polyphenolic stilbene found in various fruits and vegetables and exhibits anticancer and anti-inflammatory properties[2]. Piceatannol induces apoptosis in DLBCL cell lines[3]. Piceatannol induces autophagy and apoptosis in MOLT-4 human leukemia cells[4].

   

(1R,4aS,10aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid

(1R,4aS,10aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid

C20H26O4 (330.18309960000005)


   

coniferaldehyde

coniferaldehyde

C10H10O3 (178.062991)


CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 13

   

Octadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715156)


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.

   

N-Heptane

Dipropyl methane

C7H16 (100.1251936)


A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).

   

Sabinene hydrate

(1R,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

C10H18O (154.1357578)


   

Isointermedeol

1,4a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-1-ol

C15H26O (222.1983546)


   

g-Muurolene

7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.18779039999998)


   

palustral

1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,9,10,10a-decahydrophenanthrene-1-carbaldehyde

C20H30O (286.229653)


   
   

3,4-Dimethoxy cinnamaldehyde

3,4-Dimethoxy cinnamaldehyde

C11H12O3 (192.0786402)


   

3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

C20H22O6 (358.1416312)


   

Vanillate

4-Hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


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].

   

CHEBI:15385

(1S,8AR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene

C15H24 (204.18779039999998)


   

linoleic

9,12-Octadecadienoic acid, (9E,12E)-

C18H32O2 (280.2402172)


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].

   

Eptani

InChI=1\C7H16\c1-3-5-7-6-4-2\h3-7H2,1-2H

C7H16 (100.1251936)


   

D-CAMPHOR

(±)-Camphor

C10H16O (152.12010859999998)


(+)-camphor, also known as formosa camphor or 2-bornanone, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-camphor is considered to be an isoprenoid lipid molecule (+)-camphor is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-camphor is a bitter, camphor, and herbal tasting compound and can be found in a number of food items such as sugar apple, sunflower, fennel, and cardamom, which makes (+)-camphor a potential biomarker for the consumption of these food products. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative.

   

Cyanidin 3-glucoside

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

C21H21O11+ (449.10838160000003)


Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Found in many plants and fruits, e.g. cherries, olives and grapes

   

Delphinidin 3-glucoside

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

C21H21O12+ (465.1032966)


Delphinidin 3-glucoside is found in adzuki bean. Delphinidin 3-glucoside is isolated from grapes and many other plant species Delphinidin 3-glucoside is present in red wine. Delphinidin 3-glucoside is isolated from grapes and many other plant spp. It is found in red wine, redcurrant, summer grape, strawberry, and green bean.

   

Ligraminol E

Ligraminol E

C20H26O6 (362.17292960000003)


A natural product found in Acorus gramineus.

   
   

2-(4-methylphenyl)propan-2-ol

2-(4-methylphenyl)propan-2-ol

C10H14O (150.1044594)


   

Fenchyl acetate

2-Norbornanol, 1,3,3-trimethyl-, acetate

C12H20O2 (196.14632200000003)


   

myrtillin

delphinidin 3-O-beta-D-glucopyranoside

C21H21O12+ (465.1032966)


   

Petunidin 3-galactoside

Petunidin 3-galactoside

C22H23O12+ (479.1189458)


   

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

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

C10H10O4 (194.057906)


   

4-(3-hydroxybutyl)-2-methoxyphenol

4-(3-hydroxybutyl)-2-methoxyphenol

C11H16O3 (196.1099386)


   

delta-Cadinene

delta-Cadinene

C15H24 (204.18779039999998)


A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (position 8a).

   

5-(2-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyl-5h-furan-2-one

5-(2-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyl-5h-furan-2-one

C30H46O3 (454.34467659999996)


   

2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

C16H14O8 (334.0688644)


   

2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

C30H26O13 (594.1373346)


   

(5s)-5-[(2r)-2-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

(5s)-5-[(2r)-2-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

C30H44O4 (468.3239424)


   

(1r,2s,6r,7s,12r)-12-isopropyl-2,6-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0²,⁷]hexadec-10-ene-6-carboxylic acid

(1r,2s,6r,7s,12r)-12-isopropyl-2,6-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0²,⁷]hexadec-10-ene-6-carboxylic acid

C20H30O4 (334.214398)


   

methyl 2,5-dihydroxy-4-(6-methyl-4-oxoheptan-2-yl)benzoate

methyl 2,5-dihydroxy-4-(6-methyl-4-oxoheptan-2-yl)benzoate

C16H22O5 (294.1467162)


   

5-(2-{7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyloxolan-2-one

5-(2-{7-methoxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyloxolan-2-one

C31H50O3 (470.37597500000004)


   

methyl 4-(6-methyl-4-oxoheptan-2-yl)cyclohex-1-ene-1-carboxylate

methyl 4-(6-methyl-4-oxoheptan-2-yl)cyclohex-1-ene-1-carboxylate

C16H26O3 (266.1881846)


   

(3r,6r)-6-[(1s,3r,6s,8r,11s,12s,15r,16r)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-2-methylheptane-2,3-diol

(3r,6r)-6-[(1s,3r,6s,8r,11s,12s,15r,16r)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-2-methylheptane-2,3-diol

C30H52O3 (460.3916242)


   

(4ar,10as)-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2h-phenanthren-9-one

(4ar,10as)-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2h-phenanthren-9-one

C20H28O (284.2140038)


   

[4-hydroxy-2-(2-methoxyphenoxy)-4-(2-methoxyphenoxymethyl)oxolan-3-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

[4-hydroxy-2-(2-methoxyphenoxy)-4-(2-methoxyphenoxymethyl)oxolan-3-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C30H32O10 (552.1995372)


   

(1s,5s)-1,8-dimethyl-4-(propan-2-ylidene)spiro[4.5]dec-7-ene

(1s,5s)-1,8-dimethyl-4-(propan-2-ylidene)spiro[4.5]dec-7-ene

C15H24 (204.18779039999998)


   

methyl 6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h-cyclopenta[a]naphthalen-3-yl]-2-methyl-4-oxoheptanoate

methyl 6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h-cyclopenta[a]naphthalen-3-yl]-2-methyl-4-oxoheptanoate

C32H50O5 (514.365805)


   

(3s,3as,5ar,5br,7ar,9r,11ar,11br,13ar,13bs)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol

(3s,3as,5ar,5br,7ar,9r,11ar,11br,13ar,13bs)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H52O2 (444.3967092)


   

(1r,4as,9r,10ar)-1-(hydroxymethyl)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol

(1r,4as,9r,10ar)-1-(hydroxymethyl)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol

C20H30O2 (302.224568)


   

(1s,4as,10as)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-ol

(1s,4as,10as)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-ol

C19H28O (272.2140038)


   

methyl (4r)-4-[(2s)-6-methyl-4-oxoheptan-2-yl]-3-oxocyclohex-1-ene-1-carboxylate

methyl (4r)-4-[(2s)-6-methyl-4-oxoheptan-2-yl]-3-oxocyclohex-1-ene-1-carboxylate

C16H24O4 (280.1674504)


   

methyl (1r,2s,6r,7s,12r)-12-isopropyl-2,6-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0²,⁷]hexadec-10-ene-6-carboxylate

methyl (1r,2s,6r,7s,12r)-12-isopropyl-2,6-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0²,⁷]hexadec-10-ene-6-carboxylate

C21H32O4 (348.2300472)


   

16-isopropyl-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadec-15-ene-5-carboxylic acid

16-isopropyl-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadec-15-ene-5-carboxylic acid

C20H30O4 (334.214398)


   

4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-2-yl]-2-methoxyphenol

4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-2-yl]-2-methoxyphenol

C20H22O6 (358.1416312)


   

2,12'-bis(3,4-dihydroxyphenyl)-4,6,8',11'-tetrahydroxy-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

2,12'-bis(3,4-dihydroxyphenyl)-4,6,8',11'-tetrahydroxy-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

C30H22O12 (574.1111212000001)


   

(1r,2s,7s,8s,9s,10s)-2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

(1r,2s,7s,8s,9s,10s)-2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

C15H24 (204.18779039999998)


   

(2s,3r,4s,5r)-2-{4-[(2r)-3-hydroxy-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propyl]-2-methoxyphenoxy}oxane-3,4,5-triol

(2s,3r,4s,5r)-2-{4-[(2r)-3-hydroxy-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propyl]-2-methoxyphenoxy}oxane-3,4,5-triol

C25H34O10 (494.2151864)


   

24-ethyl coprostanol

24-ethyl coprostanol

C29H52O (416.4017942)


   

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]chromen-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]chromen-4-one

C20H18O10 (418.0899928)


   

methyl (4r)-4-[(2s,4s)-4-hydroxy-6-methylheptan-2-yl]cyclohex-1-ene-1-carboxylate

methyl (4r)-4-[(2s,4s)-4-hydroxy-6-methylheptan-2-yl]cyclohex-1-ene-1-carboxylate

C16H28O3 (268.2038338)


   

(4as,7s,8as)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

(4as,7s,8as)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

C15H24 (204.18779039999998)


   

(1s,2r,4ar,8ar)-2,5,5,8a-tetramethyl-1-[(2e)-3-methylpenta-2,4-dien-1-yl]-hexahydro-1h-naphthalen-2-ol

(1s,2r,4ar,8ar)-2,5,5,8a-tetramethyl-1-[(2e)-3-methylpenta-2,4-dien-1-yl]-hexahydro-1h-naphthalen-2-ol

C20H34O (290.2609514)


   

(1r,4ar,4br,6s,10as)-7-isopropyl-6-methoxy-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

(1r,4ar,4br,6s,10as)-7-isopropyl-6-methoxy-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

C21H32O3 (332.23513219999995)


   

3-{2,4'-dimethyl-2-[1-(4-methyl-5-oxofuran-2-ylidene)propan-2-yl]-5-methylidene-5'-(prop-1-en-2-yl)-3',3'a,5',6'-tetrahydro-2'h-spiro[cyclopentane-1,1'-inden]-4'-yl}propanoic acid

3-{2,4'-dimethyl-2-[1-(4-methyl-5-oxofuran-2-ylidene)propan-2-yl]-5-methylidene-5'-(prop-1-en-2-yl)-3',3'a,5',6'-tetrahydro-2'h-spiro[cyclopentane-1,1'-inden]-4'-yl}propanoic acid

C30H40O4 (464.29264400000005)


   

5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,1,4a-trimethyl-6-methylidene-hexahydro-2h-naphthalen-2-ol

5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,1,4a-trimethyl-6-methylidene-hexahydro-2h-naphthalen-2-ol

C20H34O2 (306.2558664)


   

2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

C15H24 (204.18779039999998)


   

2-[8-(hydroxymethyl)-4b,8-dimethyl-5,6,7,8a,9,10-hexahydrophenanthren-2-yl]propan-2-yl acetate

2-[8-(hydroxymethyl)-4b,8-dimethyl-5,6,7,8a,9,10-hexahydrophenanthren-2-yl]propan-2-yl acetate

C22H32O3 (344.23513219999995)


   

[9-(acetyloxy)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl acetate

[9-(acetyloxy)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl acetate

C24H34O4 (386.24569640000004)


   

(5r,6r)-6-hydroxy-2-methyl-5-[(2s)-1-(4-methylfuran-2-yl)propan-2-yl]cyclohex-2-en-1-one

(5r,6r)-6-hydroxy-2-methyl-5-[(2s)-1-(4-methylfuran-2-yl)propan-2-yl]cyclohex-2-en-1-one

C15H20O3 (248.14123700000002)


   

(2s,3r,4r,5r,6s)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-4-hydroxy-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

(2s,3r,4r,5r,6s)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-4-hydroxy-5-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C39H32O14 (724.1791972)


   

6-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid

6-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid

C30H48O3 (456.36032579999994)


   

(1r,4as,9r,10ar)-9-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

(1r,4as,9r,10ar)-9-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

C20H28O3 (316.2038338)


   

methyl 4-(6-hydroxy-6-methylhept-4-en-2-yl)cyclohex-1-ene-1-carboxylate

methyl 4-(6-hydroxy-6-methylhept-4-en-2-yl)cyclohex-1-ene-1-carboxylate

C16H26O3 (266.1881846)


   

2,5,9,9-tetramethyl-4,4a,5,6,7,8-hexahydrobenzo[7]annulene

2,5,9,9-tetramethyl-4,4a,5,6,7,8-hexahydrobenzo[7]annulene

C15H24 (204.18779039999998)


   

1-methyl-4-(6-methylheptan-2-ylidene)cyclohex-1-ene

1-methyl-4-(6-methylheptan-2-ylidene)cyclohex-1-ene

C15H26 (206.2034396)


   

(2e,6r)-6-[(1s,5ar,7r,9ar,9bs,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxohept-2-enoic acid

(2e,6r)-6-[(1s,5ar,7r,9ar,9bs,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxohept-2-enoic acid

C30H44O4 (468.3239424)


   

(+)-α-fenchene

(+)-α-fenchene

C10H16 (136.1251936)


   

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

C20H34O (290.2609514)


   

(2r)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

(2r)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

C17H16O5 (300.0997686)


   

citronellol, (+-)-

citronellol, (+-)-

C10H20O (156.151407)


   

(1r,2s,7r,8s,9s,10s)-2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

(1r,2s,7r,8s,9s,10s)-2,6,6,9-tetramethyltetracyclo[5.4.0.0²,⁹.0⁸,¹⁰]undecane

C15H24 (204.18779039999998)


   

(2s)-2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3h-1-benzopyran-4-one

(2s)-2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3h-1-benzopyran-4-one

C15H12O6 (288.06338519999997)


   

(4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

(4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

C15H24O (220.18270539999997)


   

(7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2h-phenanthren-1-yl)methanol

(7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2h-phenanthren-1-yl)methanol

C20H32O (288.24530219999997)


   

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

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

C22H22O13 (494.1060362)


   

(4r)-4-[(2r)-6-methyl-4-oxoheptan-2-yl]cyclohex-1-ene-1-carboxylic acid

(4r)-4-[(2r)-6-methyl-4-oxoheptan-2-yl]cyclohex-1-ene-1-carboxylic acid

C15H24O3 (252.1725354)


   

(3s)-5-[(1s,4ar,5r,8ar)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-1-en-3-ol

(3s)-5-[(1s,4ar,5r,8ar)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-1-en-3-ol

C20H34O2 (306.2558664)


   

(2e,4r,6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-2-methylhept-2-enoic acid

(2e,4r,6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-2-methylhept-2-enoic acid

C30H46O4 (470.3395916)


   

(1s,2s,3r,4s,6r,7r,8s)-8-isopropyl-1,2-dimethyltetracyclo[4.4.0.0²,⁴.0³,⁷]decane

(1s,2s,3r,4s,6r,7r,8s)-8-isopropyl-1,2-dimethyltetracyclo[4.4.0.0²,⁴.0³,⁷]decane

C15H24 (204.18779039999998)


   

(4as,7s,8as)-7-isopropyl-4a-methyl-1-methylidene-octahydronaphthalene

(4as,7s,8as)-7-isopropyl-4a-methyl-1-methylidene-octahydronaphthalene

C15H26 (206.2034396)


   

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2h-phenanthrene-1-carboxylic acid

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2h-phenanthrene-1-carboxylic acid

C20H26O4 (330.18309960000005)


   

7-isopropyl-6-methoxy-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

7-isopropyl-6-methoxy-1,4a-dimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid

C21H32O3 (332.23513219999995)


   

(1r,4ar,4br,7s,10ar)-7-hydroxy-7-isopropyl-1,4a,10a-trimethyl-9-oxo-3,4,4b,5,6,10-hexahydro-2h-phenanthrene-1-carboxylic acid

(1r,4ar,4br,7s,10ar)-7-hydroxy-7-isopropyl-1,4a,10a-trimethyl-9-oxo-3,4,4b,5,6,10-hexahydro-2h-phenanthrene-1-carboxylic acid

C21H32O4 (348.2300472)


   

[(2s,3r,4s)-2-(2-methoxyphenoxy)-4-(2-methoxyphenoxymethyl)oxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

[(2s,3r,4s)-2-(2-methoxyphenoxy)-4-(2-methoxyphenoxymethyl)oxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

C28H30O9 (510.18897300000003)


   

(5r)-5-[(2r)-2-[(3as,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

(5r)-5-[(2r)-2-[(3as,5ar,7r,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

C30H44O4 (468.3239424)


   

(3r,6r)-6-[(1s,3r,6r,8r,11s,12s,15r,16r)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-2-methylheptane-2,3-diol

(3r,6r)-6-[(1s,3r,6r,8r,11s,12s,15r,16r)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-2-methylheptane-2,3-diol

C30H52O3 (460.3916242)


   

(2r,3r,11'r,12'r)-2,12'-bis(3,4-dihydroxyphenyl)-4,6,8',11'-tetrahydroxy-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

(2r,3r,11'r,12'r)-2,12'-bis(3,4-dihydroxyphenyl)-4,6,8',11'-tetrahydroxy-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

C30H22O12 (574.1111212000001)


   

(e)-4,4'-dihydroxychalcone

(e)-4,4'-dihydroxychalcone

C15H12O3 (240.0786402)


   

7,7,12,16-tetramethyl-15-[1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

7,7,12,16-tetramethyl-15-[1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H48O4 (496.3552408)


   

(5r)-5-[(2r)-2-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one

(5r)-5-[(2r)-2-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-3-methyl-5h-furan-2-one

C30H44O3 (452.3290274)


   

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

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

C22H22O13 (494.1060362)


   

7-hydroxy-3a,6,6,9a,11a-pentamethyl-1-[1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]-1h,2h,3h,5h,5ah,7h,8h,11h-cyclopenta[a]phenanthrene-4,9,10-trione

7-hydroxy-3a,6,6,9a,11a-pentamethyl-1-[1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]-1h,2h,3h,5h,5ah,7h,8h,11h-cyclopenta[a]phenanthrene-4,9,10-trione

C30H40O6 (496.28247400000004)


   

(1r,4as,5r,8ar)-5-[(2e)-3-isopropyl-4-oxobut-2-en-1-yl]-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalene-1-carboxylic acid

(1r,4as,5r,8ar)-5-[(2e)-3-isopropyl-4-oxobut-2-en-1-yl]-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalene-1-carboxylic acid

C20H30O4 (334.214398)


   

(1''s,2s,3''r,4r,4's,5's,6''s,8''r,11''s,12''r,16''s)-6''-methoxy-4,4',7'',7'',12'',16''-hexamethyldispiro[bis(oxolane)-2,2':5',15''-pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan]-5-one

(1''s,2s,3''r,4r,4's,5's,6''s,8''r,11''s,12''r,16''s)-6''-methoxy-4,4',7'',7'',12'',16''-hexamethyldispiro[bis(oxolane)-2,2':5',15''-pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan]-5-one

C31H48O4 (484.3552408)


   

methyl (2e,6r)-6-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxohept-2-enoate

methyl (2e,6r)-6-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxohept-2-enoate

C31H46O4 (482.3395916)


   

methyl (4r)-4-[(2s)-6-methyl-4-oxohept-5-en-2-yl]cyclohex-1-ene-1-carboxylate

methyl (4r)-4-[(2s)-6-methyl-4-oxohept-5-en-2-yl]cyclohex-1-ene-1-carboxylate

C16H24O3 (264.1725354)


   

nonadeca-5,9-dienoic acid

nonadeca-5,9-dienoic acid

C19H34O2 (294.2558664)


   

(1r,4as,10ar)-7-(2-ethoxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

(1r,4as,10ar)-7-(2-ethoxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

C22H32O3 (344.23513219999995)


   

1,4,4,8-tetramethylcycloundeca-2,8-dien-1-ol

1,4,4,8-tetramethylcycloundeca-2,8-dien-1-ol

C15H26O (222.1983546)


   

6-{2',5',6,6,9a-pentamethyl-7-oxo-2,5,5a,8,9,9b-hexahydro-1h-spiro[cyclopenta[a]naphthalene-3,1'-cyclopentan]-2'-en-5'-yl}-2-methyl-4-oxohept-2-enoic acid

6-{2',5',6,6,9a-pentamethyl-7-oxo-2,5,5a,8,9,9b-hexahydro-1h-spiro[cyclopenta[a]naphthalene-3,1'-cyclopentan]-2'-en-5'-yl}-2-methyl-4-oxohept-2-enoic acid

C30H42O4 (466.30829320000004)


   

methyl 6-{3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylidene-4-oxoheptanoate

methyl 6-{3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylidene-4-oxoheptanoate

C31H46O4 (482.3395916)


   

4-{[(1r,4as,10ar)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methoxy}-4-oxobutanoic acid

4-{[(1r,4as,10ar)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methoxy}-4-oxobutanoic acid

C24H32O6 (416.2198772)


   

5-(2-{3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyl-5h-furan-2-one

5-(2-{3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}propyl)-3-methyl-5h-furan-2-one

C30H44O3 (452.3290274)


   

(6r)-6-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid

(6r)-6-[(1r,3ar,5ar,9ar,9bs,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid

C30H44O4 (468.3239424)


   

methyl 16-isopropyl-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadec-15-ene-5-carboxylate

methyl 16-isopropyl-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadec-15-ene-5-carboxylate

C21H32O4 (348.2300472)


   

6-[6-(2-carboxyethyl)-3,3a,6-trimethyl-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-3-yl]-2-methyl-4-oxohept-2-enoic acid

6-[6-(2-carboxyethyl)-3,3a,6-trimethyl-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-3-yl]-2-methyl-4-oxohept-2-enoic acid

C30H42O5 (482.30320820000003)


   

10,10-dimethyl-2,6-dimethylidenebicyclo[7.2.0]undecan-5-ol

10,10-dimethyl-2,6-dimethylidenebicyclo[7.2.0]undecan-5-ol

C15H24O (220.18270539999997)


   

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

C27H30O16 (610.153378)


   

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one

C20H18O10 (418.0899928)


   

(3s)-5-[(1r,4ar,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-1-en-3-ol

(3s)-5-[(1r,4ar,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-1-en-3-ol

C20H34O (290.2609514)


   

(1r,2s,3s,6s,8s)-3-isopropyl-6-methyl-7-methylidenetricyclo[4.4.0.0²,⁸]decane

(1r,2s,3s,6s,8s)-3-isopropyl-6-methyl-7-methylidenetricyclo[4.4.0.0²,⁸]decane

C15H24 (204.18779039999998)


   

methyl 4-(3-hydroxy-6-methyl-4-oxoheptan-2-yl)cyclohex-1-ene-1-carboxylate

methyl 4-(3-hydroxy-6-methyl-4-oxoheptan-2-yl)cyclohex-1-ene-1-carboxylate

C16H26O4 (282.1830996)


   

methyl 3-{3a,6,9b-trimethyl-3-[1-(4-methyl-5-oxooxolan-2-yl)propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h-cyclopenta[a]naphthalen-6-yl}propanoate

methyl 3-{3a,6,9b-trimethyl-3-[1-(4-methyl-5-oxooxolan-2-yl)propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,3h,4h,5h,5ah,7h,8h-cyclopenta[a]naphthalen-6-yl}propanoate

C31H48O4 (484.3552408)


   

(1r,4ar,7r,8ar)-1-methoxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalene

(1r,4ar,7r,8ar)-1-methoxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalene

C16H28O (236.2140038)


   

3-[(1r,2s,3'as,4'r,5's)-2,4'-dimethyl-2-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-5-methylidene-5'-(prop-1-en-2-yl)-3',3'a,5',6'-tetrahydro-2'h-spiro[cyclopentane-1,1'-inden]-4'-yl]propanoic acid

3-[(1r,2s,3'as,4'r,5's)-2,4'-dimethyl-2-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-5-methylidene-5'-(prop-1-en-2-yl)-3',3'a,5',6'-tetrahydro-2'h-spiro[cyclopentane-1,1'-inden]-4'-yl]propanoic acid

C30H40O4 (464.29264400000005)


   

5-[(2r)-2-[(3as,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

5-[(2r)-2-[(3as,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-3h,4h,5h,5ah,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]propyl]-5-hydroxy-3-methylfuran-2-one

C30H42O4 (466.30829320000004)