Flavan-3-ols (Homo sapiens)

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Isoferulic acid-3'-sulfateHippuric acidp-Coumaric acidTheaflavin-3'-gallate4-hydroxy-5-(3',4'-dihydroxyphenyl)valeric acidCaffeic acid-3'-sulfate(-)Epigallocatechin3-Hydroxybenzoic acid4-hydroxy-5-(3'-hydroxyphenyl)valeric acid(S)-4-Hydroxy-5-(3,4,5-trihydroxyphenyl) valeric acidBenzoic acid5-(3',5')-Dihydroxyphenyl-gamma-valerolactone3-(3-hydroxyphenyl)-3-hydroxypropanoic acid5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone3-Hydroxyhippuric acid4-hydroxyhippuric acid5-(3'hydroxyphenyl)-gamma-hydroxyvaleric acid 4'-O-glucuronidePyrocatecholp-Hydroxyphenylacetic acid(-)-Epicatechin 3-O-gallate(+)-Catechin3,4-Dihydroxybenzoic acidp-hydroxyphenylacetic acid3-(4'hydroxyphenyl)-propionic acid 3'-sulfate5'-(4'-hydroxyphenyl)-gamma-valerolactone-3-'sulfate3-Phenylpropionic acidIsoferulic acid-3'-O-glucuronideFerulic acid-4'-sulfate(S)-4-hydroxy-5-(3,5-dihydroxyphenyl) valeric acid5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate5-(3,4-dihydroxyphenyl)pentanoic acid4-O-Methylgallic acid3-(3-Hydroxyphenyl)propionic acidPyrogallolTheaflavin-3-gallateFerulic acid-4'-O-glucuronide(-)-Epicatechin-3'-O-glucuronideDihydroferulic acid-4'-O-glucuronide4-[(10R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]valeric acidω-Phenylacetic acidVanillic acidIsoferulic acidProcyanidin(Dimer)Gallic acid3-Hydroxyphenyl propionic acidCoumaric Acid 4'-O-glucuronidem-Coumaric acid1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-olHomoprotocatechuic acidDihydrocaffeic acid 3-sulfateTheaflavin-3,3'-digallateDihydroferulic acid-4'-O-sulfate(+)Epiatechin5-[(3-hydroxyphenyl)methyl]oxolan-2-one5-[(4-hydroxyphenyl)methyl]oxolan-2-oneFerulic acid5-(3''-4''-Dihydroxyphenyl)-gamma-valerolactonep-hydroxybenzoic acidDihydroferulic acidCaffeic acidBenzoic acid-4-sulfateDihydroferulic acid-4'-O-glucuronide1-(3'-4',5-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxy)propan-2-olTheaflavin3-(4'-hydroxyphenyl)propionic acid5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-glucuronide5-(3,4,5-trihydroxyphenyl)valeric acid3-(3,4-dihydroxyphenyl)propanoic acidHomovanillic acid(-)-Epicatechin712, 171473, 4, 12, 141412, 174, 141, 155, 15, 19, 213, 5, 12, 13, 213, 12, 191, 157, 14, 20, 21112, 13147, 143, 5, 12, 17, 18, 214, 12, 14, 18, 195, 9, 12, 17144, 5, 7, 1461512, 195, 2112, 171, 154, 1419145, 15, 19, 211714, 1573, 4, 1412, 17191, 4, 144, 14, 1914, 192, 8, 10, 222, 4, 5, 7, 8, 10...13, 15, 18, 19, 2113, 2118, 193, 12, 17-19, 214, 11, 1412, 171217, 19195, 7, 144, 11, 12, 14, 153, 1371, 157, 145, 143, 12, 1912, 1972, 5, 227145, 2117p-hydroxybenzoic acid4, 14, 18, 19, 21Benzoic acid-4-sulfate4-Hydroxyhippuric acid12, 19Pyrocatechol12, 19, 2112, 14Homovanillic acid1-(3',4'-Dihydroxyphenyl)-3-(2'',4''-6''-trihydroxyphenyl)propan-2-ol14, 194, 5, 7, 14Catechin133-(3,4-dihydroxyphenyl)propanoic acid3, 12, 133-(3-Hydroxyphenyl)propionic acid3, 13, 143-(4'-Hydroxyphenyl)propionic acidReductase3, 13, 14Sulfuryltransferase3, 1717CoA3, 17Catechol-O-methyltransferase17Catechol-O-methyltransferase17UDP-glucuronyltransferase17Sulfuryltransferase17UDP-glucuronyltransferaseSulfuryltransferase1717ReductaseSulfuryltransferase3, 1717Sulfuryltransferase17UDP-glucuronyltransferase17CoACoA3, 173, 17CoA3, 17CoA4-Hydroxybenzoic acid 3-sulfate3, 177Gallocatechin13-(3,4-dihydroxyphenyl)propanoic acid3, 5, 12, 13, 15...3-(4'-hydroxyphenyl)propionic acid4-Hydroxyhippuric acid12, 1512, 15, 19, 21p-hydroxybenzoic acid3-Hydroxyhippuric acid4, 14, 15, 18, 19, 215, 15, 19, 213-Hydroxybenzoic acid3,4-Dihydroxybenzoic acid5, 15, 19, 21Homoprotocatechuic acid13, 15, 18, 19, 217, 14, 213-O-Methylgallic acid15Pyrogallol-1-sulfatePyrogallol-2-O-glucuronide15Pyrogallol-2-sulfate1515(-)-Epicatechin-3'-sulfate2, 8, 10, 16, 22


Description

Proposed metabolic pathway of flavan-3-ols (also known as flavanols) in humans.

Flavanols are derivatives of flavans and include catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. These compounds differ considerably not only in their structural and functional properties, but also in their metabolism and bioavailability. Green arrows indicate microbiota-mediated steps, and Red arrows represent mammalian enzyme-mediated conversions. Pink arrows indicate steps that can be both microbiota- or enzyme-mediated. This pathway was developed based upon 22 papers, therefore black arrows indicate missing information regarding the nature of conversion.

Acknowledgements: This pathway is based upon work from COST Action POSITIVe, supported by COST (European Cooperation in Science and Technology.

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Bibliography

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  1. Clifford MN, van der Hooft JJ, Crozier A; ''Human studies on the absorption, distribution, metabolism, and excretion of tea polyphenols.''; Am J Clin Nutr, 2013 PubMed Europe PMC
  2. Tsang C, Auger C, Mullen W, Bornet A, Rouanet JM, Crozier A, Teissedre PL; ''The absorption, metabolism and excretion of flavan-3-ols and procyanidins following the ingestion of a grape seed extract by rats.''; Br J Nutr, 2005 PubMed Europe PMC
  3. Rodriguez-Mateos A, Vauzour D, Krueger CG, Shanmuganayagam D, Reed J, Calani L, Mena P, Del Rio D, Crozier A; ''Bioavailability, bioactivity and impact on health of dietary flavonoids and related compounds: an update.''; Arch Toxicol, 2014 PubMed Europe PMC
  4. Roowi S, Stalmach A, Mullen W, Lean ME, Edwards CA, Crozier A; ''Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans.''; J Agric Food Chem, 2010 PubMed Europe PMC
  5. Monagas M, Urpi-Sarda M, Sánchez-Patán F, Llorach R, Garrido I, Gómez-Cordovés C, Andres-Lacueva C, Bartolomé B; ''Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites.''; Food Funct, 2010 PubMed Europe PMC
  6. Kutschera M, Engst W, Blaut M, Braune A; ''Isolation of catechin-converting human intestinal bacteria.''; J Appl Microbiol, 2011 PubMed Europe PMC
  7. Borges G, van der Hooft JJJ, Crozier A; ''''; , PubMed Europe PMC
  8. Actis-Goretta L, Lévèques A, Giuffrida F, Romanov-Michailidis F, Viton F, Barron D, Duenas-Paton M, Gonzalez-Manzano S, Santos-Buelga C, Williamson G, Dionisi F; ''Elucidation of (-)-epicatechin metabolites after ingestion of chocolate by healthy humans.''; Free Radic Biol Med, 2012 PubMed Europe PMC
  9. Urpi-Sarda M, Monagas M, Khan N, Llorach R, Lamuela-Raventós RM, Jáuregui O, Estruch R, Izquierdo-Pulido M, Andrés-Lacueva C; ''The current distribution of CD4+ T-lymphocyte counts among adultsin the United States with human immunodeficiency virus infections: estimates based on the experience of the U.S. Army. U.S. Army Retrovirus Research Group.''; J Acquir Immune Defic Syndr, 1990 PubMed Europe PMC
  10. Okushio K, Suzuki M, Matsumoto N, Nanjo F, Hara Y; ''Identification of (-)-epicatechin metabolites and their metabolic fate in the rat.''; Drug Metab Dispos, 1999 PubMed Europe PMC
  11. Schantz M, Erk T, Richling E; ''Metabolism of green tea catechins by the human small intestine.''; Biotechnol J, 2010 PubMed Europe PMC
  12. Crozier A, Del Rio D, Clifford MN; ''Bioavailability of dietary flavonoids and phenolic compounds.''; Mol Aspects Med, 2010 PubMed Europe PMC
  13. Gross G, Jacobs DM, Peters S, Possemiers S, van Duynhoven J, Vaughan EE, van de Wiele T; ''In vitro bioconversion of polyphenols from black tea and red wine/grape juice by human intestinal microbiota displays strong interindividual variability.''; J Agric Food Chem, 2010 PubMed Europe PMC
  14. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J; ''Trypsin-catalyzed activation of aspartase.''; Biochem Biophys Res Commun, 1975 PubMed Europe PMC
  15. Pereira-Caro G, Moreno-Rojas JM, Brindani N, Del Rio D, Lean MEJ, Hara Y, Crozier A; ''Identification and expression analysis of genes involved in anthocyanin and proanthocyanidin biosynthesis in the fruit of blackberry''; , 2012 PubMed Europe PMC
  16. Ottaviani JI, Momma TY, Kuhnle GK, Keen CL, Schroeter H; ''Structurally related (-)-epicatechin metabolites in humans: assessment using de novo chemically synthesized authentic standards.''; Free Radic Biol Med, 2012 PubMed Europe PMC
  17. Del Rio D, Stalmach A, Calani L, Crozier A; ''Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols.''; Nutrients, 2010 PubMed Europe PMC
  18. de Ferrars RM, Czank C, Zhang Q, Botting NP, Kroon PA, Cassidy A, Kay CD; ''The pharmacokinetics of anthocyanins and their metabolites in humans.''; Br J Pharmacol, 2014 PubMed Europe PMC
  19. Kay CD, Pereira-Caro G, Ludwig IA, Clifford MN, Crozier A; ''Anthocyanins and Flavanones Are More Bioavailable than Previously Perceived: A Review of Recent Evidence.''; Annu Rev Food Sci Technol, 2017 PubMed Europe PMC
  20. Del Rio D, Borges G, Crozier A; ''Berry flavonoids and phenolics: bioavailability and evidence of protective effects.''; Br J Nutr, 2010 PubMed Europe PMC
  21. Urpi-Sarda M, Monagas M, Khan N, Llorach R, Lamuela-Raventós RM, Jáuregui O, Estruch R, Izquierdo-Pulido M, Andrés-Lacueva C; ''Targeted metabolic profiling of phenolics in urine and plasma after regular consumption of cocoa by liquid chromatography-tandem mass spectrometry.''; J Chromatogr A, 2009 PubMed Europe PMC
  22. Crozier A, Jaganath IB, Clifford MN; ''Dietary phenolics: chemistry, bioavailability and effects on health.''; Nat Prod Rep, 2009 PubMed Europe PMC

History

View all...
CompareRevisionActionTimeUserComment
107164view14:25, 17 September 2019MaintBotChEBI identifier normalization
106786view13:26, 17 September 2019MaintBotHMDB identifier normalization
97378view13:40, 12 May 2018EgonwReplaced secondary ChEBI identifiers with primary identifiers (I missed a few CoAs).
97376view09:47, 12 May 2018EgonwReplaced the last few InChIKeys with PubChem CIDs.
97375view09:42, 12 May 2018EgonwReplaced secondary ChEBI identifiers with primary identifiers.
97313view04:25, 9 May 2018Khanspersadded xrefs
97304view22:22, 8 May 2018EiriniDelData nodes annotated
96606view11:42, 23 March 2018DeSlOntology Term : 'flavonoid biosynthetic pathway' added !
96604view11:07, 23 March 2018EiriniDelReplace InChiKey with PubChemID
96601view10:52, 23 March 2018EgonwOntology Term : 'classic metabolic pathway' added !
96600view10:50, 23 March 2018EgonwModified description
96599view10:49, 23 March 2018EgonwReplace an InChIKey (no links out yet) with a PubChem compound identifier.
96584view02:24, 22 March 2018EiriniDelModified description
96583view02:18, 22 March 2018EiriniDelModified title
96582view02:16, 22 March 2018EiriniDelNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
(+)-CatechinMetabolite1203 (PubChem-compound)
(+)EpiatechinMetabolite12309508 (PubChem-compound)
(-)-Epicatechin 3-O-gallateMetabolite65064 (PubChem-compound)
  • C22H18O11
  • [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate
  • Epigallocatechingallate
(-)-Epicatechin-3'-O-glucuronideMetabolite76969982 (PubChem-compound)
(-)-Epicatechin-3'-sulfateMetabolite124202087 (PubChem-compound)
(-)-EpicatechinMetabolite72276 (PubChem-compound)
  • C15H14O6
  • (3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
  • 3,5,7,3',4'-Pentahydroxyflavane
(-)EpigallocatechinMetabolite72277 (PubChem-compound)
  • C15H14O7
  • (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol)
(S)-4-Hydroxy-5-(3,4,5-trihydroxyphenyl) valeric acidMetabolite101900149 (PubChem-compound)
(S)-4-hydroxy-5-(3,5-dihydroxyphenyl) valeric acidMetabolite101900150 (PubChem-compound)
1-(3',4'-Dihydroxyphenyl)-3-(2'',4''-6''-trihydroxyphenyl)propan-2-olMetabolite21722175 (PubChem-compound)
  • C15H16O6
  • 2-[3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]benzene-1,3,5-triol
1-(3'-4',5-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxy)propan-2-olMetabolite21722175 (PubChem-compound)
1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-olMetabolite21722175 (PubChem-compound)
3,4-Dihydroxybenzoic acidMetaboliteCHEBI:36062 (ChEBI)
  • C7H6O4
  • 3,4-Dihydroxybenzoic acid
  • Proteocatechuic acid
3-(3,4-dihydroxyphenyl)propanoic acidMetabolite348454 (PubChem-compound)
  • C9H10O4
  • 3-(3,4-dihydroxyphenyl)propanoic acid
  • Dihydrocaffeic acid
3-(3-Hydroxyphenyl)propionic acidMetabolite91 (PubChem-compound)
  • C9H10O3
  • 3-(3-hydroxyphenyl)-propionic acid
  • 3-(3'-hydroxyphenyl)propionic acid
  • 3-hydroxyphenylpropionic acid
  • 3'-hydroxy-dihydrocinnamic acid
  • m-hydroxy-dihydrocinnamic acid
3-(3-hydroxyphenyl)-3-hydroxypropanoic acidMetabolite102959 (PubChem-compound)
3-(4'-Hydroxyphenyl)propionic acidMetabolite91 (PubChem-compound)
3-(4'-hydroxyphenyl)propionic acidMetabolite91 (PubChem-compound)
3-(4'hydroxyphenyl)-propionic acid 3'-sulfateMetabolite
3-Hydroxybenzoic acidMetabolite7420 (PubChem-compound)
  • C7H6O3
  • 3-hdroxybenzoic acid
  • m-hydroxybenzoic acid
  • 3-hydroxybenzenecarboxylic acid
3-Hydroxyhippuric acidMetabolite450268 (PubChem-compound)
  • C9H9NO4
  • 3-hydroxyhippuric acid
  • 3-hydroxyhippuric acid
  • N-(3-hydroxybenzoyl)glucine
3-Hydroxyphenyl propionic acidMetabolite91 (PubChem-compound)
  • C9H10O3
  • 3-Hydroxyphenylpropionic acid
  • 3-(3'-hydroxyphenyl)propionic acid
3-O-Methylgallic acidMetaboliteCHEBI:28647 (ChEBI)
3-Phenylpropionic acidMetabolite107 (PubChem-compound)
  • C9H10O2
  • 3-phenylpropionic acid
  • 3-(phenyl)propionic acid
  • Benzenepropanoic acid
  • Dihydrocinnamic acid
4-Hydroxybenzoic acid 3-sulfateMetabolite76974408 (PubChem-compound)
4-Hydroxyhippuric acidMetabolite151012 (PubChem-compound)
  • C9H9NO4
  • [(4-hydroxyphenyl)formamido]acetic acid
  • 4-Hydroxyhippuric acid
  • 4'-Hydroxyhippuric acid
  • N-(4-hydroxybenzoyl)glycine
4-O-Methylgallic acidMetabolite78016 (PubChem-compound)
4-[(10R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]valeric acidMetaboliteCHEBI:52023 (ChEBI) 5(phenyl)-gamma-hydroxyvaleric acid-3'-sulfate
4-hydroxy-5-(3',4'-dihydroxyphenyl)valeric acidMetabolite
4-hydroxy-5-(3'-hydroxyphenyl)valeric acidMetabolite5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid
4-hydroxyhippuric acidMetabolite151012 (PubChem-compound)
  • C9H9NO4
  • [(4-hydroxyphenyl)formamido]acetic acid
  • 4-hydroxyhippuric acid
  • 4'-Hydroxyhippuric acid
  • N-(4-hydroxybenzoyl)glycine
5'-(4'-hydroxyphenyl)-gamma-valerolactone-3-'sulfateMetabolite
5-(3''-4''-Dihydroxyphenyl)-gamma-valerolactoneMetabolite89285 (PubChem-compound)
  • C11H12O4
  • 5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactoneMetabolite44389277 (PubChem-compound)
  • C11H12O5
  • 5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
5-(3',5')-Dihydroxyphenyl-gamma-valerolactoneMetaboliteHMDB0029187 (HMDB)
5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-glucuronideMetabolite
5-(3'hydroxyphenyl)-gamma-hydroxyvaleric acid 4'-O-glucuronideMetabolite
5-(3,4,5-trihydroxyphenyl)valeric acidMetabolite
5-(3,4-dihydroxyphenyl)pentanoic acidMetabolite49831816 (PubChem-compound)
  • C11H14O4
  • 5-(3,4-dihydroxyphenyl)pentanoic acid
  • 5-(3',4'-dihydroxyphenyl)valeric acid
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphateMetaboliteHMDB0059993 (HMDB)
5-[(3-hydroxyphenyl)methyl]oxolan-2-oneMetabolite3028409 (PubChem-compound)
  • C11H12O2
  • 5-[(3-hydroxyphenyl)methyl]oxolan-2-one
  • 5-(3'-hydroxyphenyl)-gamma-valerolactone
5-[(4-hydroxyphenyl)methyl]oxolan-2-oneMetabolite11550142 (PubChem-compound)
  • C11H12O3
  • 5-[(4-hydroxyphenyl)methyl]oxolan-2-one
  • 5-(4'-hydroxyphenyl)-gamma-valerolactone
Benzoic acid-4-sulfateMetabolite
Benzoic acidMetabolite243 (PubChem-compound)
  • C7H6O2
  • benzoic acid
Caffeic acid-3'-sulfateMetabolite102261219 (PubChem-compound)
Caffeic acidMetabolite689043 (PubChem-compound)
  • C9H8O4
  • (E )-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
CatechinMetabolite1203 (PubChem-compound)
  • C15H14O6
  • 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Catechol-O-methyltransferaseGeneProductENSG00000093010 (Ensembl)
CoAMetaboliteCHEBI:15346 (ChEBI)
Coumaric Acid 4'-O-glucuronideMetabolite71314996 (PubChem-compound)
Dihydrocaffeic acid 3-sulfateMetabolite49844181 (PubChem-compound)
Dihydroferulic acid-4'-O-glucuronideMetabolite190069 (PubChem-compound)
Dihydroferulic acid-4'-O-sulfateMetabolite187489 (PubChem-compound)
Dihydroferulic acidMetabolite14340 (PubChem-compound)
  • C10H12O4
  • 3-(4-hydroxy-3-methoxyphenyl)propanoic acid
  • dihydroconiferylate
Ferulic acid-4'-O-glucuronideMetabolite6443140 (PubChem-compound)
  • C16H18O10
  • (2R,3R,4R,5S,6R)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
  • trans-Ferulic acid glucuronide
Ferulic acid-4'-sulfateMetabolite6305574 (PubChem-compound)
  • C10H10O7S
  • (2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
  • trans-Ferulic acid sulfate
Ferulic acidMetabolite709 (PubChem-compound)
  • C10H10O4
  • 3-(4'-hydroxy-3-methoxyphenyl)prop-2-enoic acid
  • 3-methylcaffeic acid
Gallic acidMetabolite370 (PubChem-compound)
  • C7H6O5
  • 3,4,5-trihydroxybenzoic acid
GallocatechinMetabolite65084 (PubChem-compound)
  • C15H14O7
  • (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol)
Hippuric acidMetabolite464 (PubChem-compound)
  • C9H9NO3
  • hippuric acid
  • N-benzoylglycine
Homoprotocatechuic acidMetabolite547 (PubChem-compound) 3',4'-Dihydroxyphenylacetic acid
Homovanillic acidMetabolite1738 (PubChem-compound)
  • C9H10O4
  • Homovanillic acid
  • (4-hydroxy-3-methoxyphenyl)acetic acid
  • 3-methoxy-4-hydroxyphenylacetic acid
  • 3-methoxy-4-hydroxyphenylacetate
  • 3'-methoxy-4'-hydroxyphenylacetic
Isoferulic acid-3'-O-glucuronideMetabolite49844484 (PubChem-compound)
  • C16H18O10
  • (2S,3S,4S,5R,6S)-6-[5-[(E)-2-carboxyethenyl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Isoferulic acid-3'-sulfateMetabolite71749556 (PubChem-compound)
  • C10H10O7S
  • (2E)-3-[4-methoxy-3-(sulfooxyphenyl]propan-2-enoic acid
Isoferulic acidMetabolite736189 (PubChem-compound)
  • C10H10O4
  • (E )-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
  • 4-methylcaffeic acid
Procyanidin(Dimer)Metabolite11250133 (PubChem-compound)
PyrocatecholMetabolite289 (PubChem-compound)
  • C6H6O2
  • Benzene-1,2-diol
Pyrogallol-1-sulfateMetabolite54110629 (PubChem-compound)
Pyrogallol-2-O-glucuronideMetabolite122553541 (PubChem-compound)
Pyrogallol-2-sulfateMetabolite92013662 (PubChem-compound)
PyrogallolMetabolite1057 (PubChem-compound)
  • C6H6O3
  • Benzene-1,2,3-triol
ReductaseProtein
SulfuryltransferaseProtein
Theaflavin-3'-gallateMetabolite102115505 (PubChem-compound)
  • C36H28O16
  • [(2R,3R)-5,7-dihydroxy-2-[3,4,5-trihydroxy-6-oxo-1-[(2S,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-8-yl]-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate
Theaflavin-3,3'-digallateMetabolite21146795 (PubChem-compound)
  • C43H32O20
  • [3-hydroxy-5-oxo-4-(3,4,4-trihydroxybenzoyl)oxy-1,8-bis[(2R,3R-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-6-yl]3,4,5-trihydroxybenzoate
  • Type your comment here
Theaflavin-3-gallateMetabolite102115506 (PubChem-compound)
  • C36H28O16
  • (3R)-5,7-dihydroxy-2-{1,2,8-trihydroxy-9-oxo-4-[3S0-,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyron-2-yl]benzo[7]annuel-6-yl}-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)
TheaflavinMetabolite114777 (PubChem-compound)
  • C29H24O12
  • Theaflavin
UDP-glucuronyltransferaseProtein
UDP-glucuronyltransferaseProteinEC 2.4.1.17 (BRENDA)
Vanillic acidMetabolite8468 (PubChem-compound)
  • C8H8O4
  • vanillic acid
  • 3-methoxy-4-hydroxybenzoic acid
  • p-vanillic acid
  • 4-hydroxy-3-methoxybenzoic acid
m-Coumaric acidMetabolite637541 (PubChem-compound)
  • C9H8O3
  • m-Coumaric acid
  • 3-hydroxycinnamic acid
p-Coumaric acidMetabolite17450 (PubChem-compound)
  • C9H8O3
  • Coumaric acid
  • 4-hydroxycinnamic acid
p-Hydroxyphenylacetic acidMetabolite127 (PubChem-compound)
p-hydroxybenzoic acidMetabolite135 (PubChem-compound)
  • C7H6O8
  • p-hydroxybenzoic acid
  • 4-hydroxybenzoic acid
  • 4-hydroxybenzenecarboxylic acid
p-hydroxyphenylacetic acidMetabolite127 (PubChem-compound)
ω-Phenylacetic acidMetabolite999 (PubChem-compound)
  • C8H8O2
  • ω-Phenylacetic acid
  • Phenylacetic acid
  • 2-phenylacetic acid
  • 2-phenylethanoate

Annotated Interactions

No annotated interactions

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