Flavan-3-ol metabolic pathway (Homo sapiens)

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Isoferulic acidDihydroferulic acid1-(3'-4',5-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxy)propan-2-ol3-Hydroxybenzoic acid5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone(-)-Epicatechin3-(3-hydroxyphenyl)-3-hydroxypropanoic acid(-)-Epicatechin-3'-O-glucuronide(-)EpigallocatechinCoumaric Acid 4'-O-glucuronide5'-(4'-hydroxyphenyl)-gamma-valerolactone-3-'sulfate5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphateIsoferulic acid-3'-sulfateDihydrocaffeic acid 3-sulfatePyrocatechol(S)-4-hydroxy-5-(3,5-dihydroxyphenyl) valeric acid5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-glucuronidep-Coumaric acidBenzoic acid-4-sulfate3-(4'hydroxyphenyl)-propionic acid 3'-sulfate5-(3,4,5-trihydroxyphenyl)valeric acidFerulic acid-4'-sulfateHomovanillic acid5-(3',5')-Dihydroxyphenyl-gamma-valerolactoneIsoferulic acid-3'-O-glucuronideCaffeic acid3-Phenylpropionic acidPyrogallol3-Hydroxyhippuric acid(+)Epiatechinp-Hydroxyphenylacetic acidFerulic acid-4'-O-glucuronideHomoprotocatechuic acidTheaflavin3-(4'-hydroxyphenyl)propionic acidm-Coumaric acid5-[(4-hydroxyphenyl)methyl]oxolan-2-one4-hydroxy-5-(3',4'-dihydroxyphenyl)valeric acidFerulic acidHippuric acid5-[(3-hydroxyphenyl)methyl]oxolan-2-oneTheaflavin-3-gallate1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-olp-hydroxybenzoic acid5-(3,4-dihydroxyphenyl)pentanoic acid4-O-Methylgallic acidProcyanidin(Dimer)Theaflavin-3'-gallateDihydroferulic acid-4'-O-glucuronide4-hydroxy-5-(3'-hydroxyphenyl)valeric acid3-(3-Hydroxyphenyl)propionic acid4-hydroxyhippuric acid5-(3'hydroxyphenyl)-gamma-hydroxyvaleric acid 4'-O-glucuronideCaffeic acid-3'-sulfateDihydroferulic acid-4'-O-sulfateVanillic acidGallic acid(+)-CatechinDihydroferulic acid-4'-O-glucuronide5-(3''-4''-Dihydroxyphenyl)-gamma-valerolactonep-hydroxyphenylacetic acid(-)-Epicatechin 3-O-gallate3-Hydroxyphenyl propionic acidω-Phenylacetic acid(S)-4-Hydroxy-5-(3,4,5-trihydroxyphenyl) valeric acidBenzoic acid4-[(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 acid3-(3,4-dihydroxyphenyl)propanoic acid3,4-Dihydroxybenzoic acidTheaflavin-3,3'-digallate1, 2238, 196, 8, 18, 231323231, 2, 216, 19, 2312, 237, 10, 175, 181, 2, 213, 7-96, 233, 86, 7, 12, 236, 21, 23193, 198, 18, 19194, 6, 8, 19, 237, 2012, 14, 20, 2321121912, 2310, 11, 15, 1733, 4, 8, 18-206, 18, 238, 193, 812235, 205, 83, 83, 87, 20126, 236, 22, 234, 197, 12, 231, 2, 7, 19, 201, 2, 21123, 4, 7, 8, 18...6, 7, 10-12, 15...1288, 18, 1919, 2337, 231, 2, 7, 19, 20121, 2, 4, 5, 19...1, 2, 23233, 81, 2, 6, 8, 22...5, 7, 8, 18, 201, 2, 2123p-hydroxybenzoic acidBenzoic acid-4-sulfate4, 6, 19, 20, 234-Hydroxyhippuric acid8, 198, 19, 20PyrocatecholHomovanillic acid8, 2319, 231-(3',4'-Dihydroxyphenyl)-3-(2'',4''-6''-trihydroxyphenyl)propan-2-olCatechin6, 7, 12, 2353-(3,4-dihydroxyphenyl)propanoic acid5, 8, 183-(3-Hydroxyphenyl)propionic acid5, 18, 233-(4'-Hydroxyphenyl)propionic acid5, 18, 23ReductaseSulfuryltransferase3, 183CoA3, 18Catechol-O-methyltransferase3UDP-glucuronyltransferase3SulfuryltransferaseReductase3Sulfuryltransferase3, 183SulfuryltransferaseUDP-glucuronyltransferase33CoACoA3, 18CoA3, 183, 18CoA3, 184-Hydroxybenzoic acid 3-sulfate12Gallocatechin3-(3,4-dihydroxyphenyl)propanoic acid211, 2, 5, 7, 8, 18...3-(4'-hydroxyphenyl)propionic acid1, 2, 84-Hydroxyhippuric acid1, 2, 8, 19, 20p-hydroxybenzoic acid3-Hydroxyhippuric acid1, 2, 4, 6, 19...3-Hydroxybenzoic acid1, 2, 7, 19, 203,4-Dihydroxybenzoic acid1, 2, 7, 19, 20Homoprotocatechuic acid1, 2, 4, 5, 19...3-O-Methylgallic acid12, 20, 231, 2Pyrogallol-1-sulfate1, 2Pyrogallol-2-O-glucuronide1, 2Pyrogallol-2-sulfate1, 2(-)-Epicatechin-3'-sulfate10, 11, 15-17


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; 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. ''Identification and expression analysis of genes involved in anthocyanin and proanthocyanidin biosynthesis in the fruit of blackberry''; , 2012 PubMed Europe PMC Scholia
  2. Pereira-Caro G, Moreno-Rojas JM, Brindani N, Del Rio D, Lean MEJ, Hara Y, Crozier A; ''Bioavailability of Black Tea Theaflavins: Absorption, Metabolism, and Colonic Catabolism.''; J Agric Food Chem, 2017 PubMed Europe PMC Scholia
  3. 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 Scholia
  4. 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 Scholia
  5. 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 Scholia
  6. 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 Scholia
  7. 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 Scholia
  8. Crozier A, Del Rio D, Clifford MN; ''Bioavailability of dietary flavonoids and phenolic compounds.''; Mol Aspects Med, 2010 PubMed Europe PMC Scholia
  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 Scholia
  10. Crozier A, Jaganath IB, Clifford MN; ''Dietary phenolics: chemistry, bioavailability and effects on health.''; Nat Prod Rep, 2009 PubMed Europe PMC Scholia
  11. 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 Scholia
  12. Borges G, van der Hooft JJJ, Crozier A; ''''; , PubMed Europe PMC Scholia
  13. Kutschera M, Engst W, Blaut M, Braune A; ''Isolation of catechin-converting human intestinal bacteria.''; J Appl Microbiol, 2011 PubMed Europe PMC Scholia
  14. Del Rio D, Borges G, Crozier A; ''Berry flavonoids and phenolics: bioavailability and evidence of protective effects.''; Br J Nutr, 2010 PubMed Europe PMC Scholia
  15. 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 Scholia
  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 Scholia
  17. 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 Scholia
  18. 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 Scholia
  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 Scholia
  20. 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 Scholia
  21. 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 Scholia
  22. Schantz M, Erk T, Richling E; ''Metabolism of green tea catechins by the human small intestine.''; Biotechnol J, 2010 PubMed Europe PMC Scholia
  23. 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 DOI Scholia

History

View all...
CompareRevisionActionTimeUserComment
134329view13:13, 20 July 2024EweitzModified description
134290view05:50, 20 July 2024EgonwRemoved a template comment
125301view17:41, 31 January 2023LarsgwFix references
124168view13:26, 22 September 2022DeSlOntology Term : 'PW:0000522' removed !
124167view13:26, 22 September 2022DeSlAdded last missing metaboliute IDs
124166view13:21, 22 September 2022DeSlAdded two more missing metabolite IDs
124165view13:17, 22 September 2022DeSlFoudn another ID for missing metabolite
124164view13:16, 22 September 2022DeSlFound another ID for metabolite
124163view13:13, 22 September 2022DeSlFinal layout changes
124162view12:57, 22 September 2022DeSlConnected all enzymes properly to MIM-conversions
124161view12:51, 22 September 2022DeSlFinshed layout update on the left top
124160view12:47, 22 September 2022DeSlStarted cleaning up layout
124159view12:41, 22 September 2022DeSlAdded ID for Benzoic acid-4-sulfate
123876view09:15, 23 August 2022EgonwReplaced with an identifier of the neutral compound with Wikidata mappings
120817view19:03, 11 January 2022KhanspersModified title
111805view15:20, 7 September 2020DeSlupdated UDP-glucuronyltransferase ID (last one)
111804view15:18, 7 September 2020DeSlUpdated ID for UDP-glucuronyltransferase (2x)
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

View all...
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'-sulfateMetabolite124202088 (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'-sulfateMetaboliteMIMULQQHBAZGER-UHFFFAOYSA-M (InChIKey) AKA 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfate; foudn in PhytoHub https://phytohub.eu/entries/PHUB001753
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 acidMetabolite124202072 (PubChem-compound) AKA 4-Hydroxy-5-(3',4'-dihydroxyphenyl)-valeric acid-O-glucuronide
4-hydroxy-5-(3'-hydroxyphenyl)valeric acidMetabolite52920334 (PubChem-compound) AKA 5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid; 4-Hydroxy-5-(3-hydroxyphenyl)valeric 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-'sulfateMetaboliteCHEBI:88750 (ChEBI) Might be know under the name 5-(Hydroxyphenyl)-γ-Valerolactone-Sulfate [PMID:31694297].
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-glucuronideMetabolite124202062 (PubChem-compound)
5-(3'hydroxyphenyl)- gamma-hydroxyvaleric acid 4'-O-glucuronideMetaboliteLLKUARGHNZMSRT-UHFFFAOYNA-N (InChIKey) AKA 5-(3'hydroxyphenyl)- gamma-hydroxyvaleric acid 4'-O-glucuronide; found in PhytoHub https://phytohub.eu/entries/PHUB001745
5-(3,4,5-trihydroxyphenyl)valeric acidMetabolite101786869 (PubChem-compound) AKA 5-(3,4,5-Trihydroxyphenyl)pentanoic acid (valeric is also known as pentanoic)
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-sulfateMetabolite18690341 (PubChem-compound) AKA 4-Sulfooxybenzoic acid
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
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-glucuronyltransferaseProtein2.4.1.17 (Enzyme Nomenclature)
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

Retrieved from "https://classic.wikipathways.org/index.php/Pathway:WP4238"
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