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Record Information
Version3.6
Creation Date2006-05-22 15:12:09 UTC
Update Date2016-02-11 01:05:48 UTC
HMDB IDHMDB02780
Secondary Accession NumbersNone
Metabolite Identification
Common NameCatechin
DescriptionCatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. -- Pubchem.
Structure
Thumb
Synonyms
ValueSource
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-olChEBI
(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-olChEBI
(+)-CatecholChEBI
(+)-Cyanidan-3-olChEBI
(2R,3S)-(+)-CatechinChEBI
(2R,3S)-CatechinChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolChEBI
Catechuic acidChEBI
CianidanolChEBI
CyanidanolChEBI
D-CatechinChEBI
(+)-Catechin hydrateHMDB
(+)-CyanidanolHMDB
(+/-)-catechinHMDB
(+/-)-catechin hydrateHMDB
3,3',4',5,7-FlavanpentolHMDB
BiocatechinHMDB
CatechinateHMDB
Catechinic acidHMDB
CatechuateHMDB
CatergenHMDB
CianidanolumHMDB
CianidolHMDB
D-(+)-CatechinHMDB
trans3,3,4,5,7 PentahydroxyflavaneHMDB
YK-85 light yellow powder 85HMDB
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(+)-catechol
CAS Registry Number154-23-4
SMILES
O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
InChI KeyInChIKey=PFTAWBLQPZVEMU-DZGCQCFKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catechins. These are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.51PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.65 mg/mLALOGPS
logP1.02ALOGPS
logP1.8ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74 m3·mol-1ChemAxon
Polarizability27.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0190000000-0b55363090666c3a1f0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ab9-0900000000-5dfb75ce17e0aea0642bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-003r-9000000000-ae956114187e6320ae3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-dd93ef481c2fea84d4a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0980000000-97f9a54412368150d277View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Intestine
  • Platelet
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.650 +/- 0.009 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.223 +/- 0.147 uMAdult (>18 years old)Female
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124
  • Not Applicable
details
UrineDetected and Quantified0.0058 +/- 0.011 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID124
Phenol Explorer Metabolite ID124
FoodDB IDFDB002571
KNApSAcK IDC00000947
Chemspider ID8711
KEGG Compound IDC06562
BioCyc IDCPD-1961
BiGG IDNot Available
Wikipedia LinkCatechin
NuGOwiki LinkHMDB02780
Metagene LinkHMDB02780
METLIN ID3419
PubChem Compound9064
PDB IDKXN
ChEBI ID15600
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yang CS, Lee MJ, Chen L: Human salivary tea catechin levels and catechin esterase activities: implication in human cancer prevention studies. Cancer Epidemiol Biomarkers Prev. 1999 Jan;8(1):83-9. [9950244 ]
  2. Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ: Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr. 2003 Jun;77(6):1466-73. [12791625 ]
  3. Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003 May;67(5):1140-3. [12834296 ]
  4. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. [11823574 ]
  5. Lhoste EF, Ouriet V, Bruel S, Flinois JP, Brezillon C, Magdalou J, Cheze C, Nugon-Baudon L: The human colonic microflora influences the alterations of xenobiotic-metabolizing enzymes by catechins in male F344 rats. Food Chem Toxicol. 2003 May;41(5):695-702. [12659723 ]
  6. Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. [11603654 ]
  7. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. [16197573 ]
  8. Roura E, Andres-Lacueva C, Estruch R, Lamuela-Raventos RM: Total polyphenol intake estimated by a modified Folin-Ciocalteu assay of urine. Clin Chem. 2006 Apr;52(4):749-52. Epub 2006 Feb 9. [16469857 ]
  9. Li C, Lee MJ, Sheng S, Meng X, Prabhu S, Winnik B, Huang B, Chung JY, Yan S, Ho CT, Yang CS: Structural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion. Chem Res Toxicol. 2000 Mar;13(3):177-84. [10725114 ]
  10. Pignatelli P, Di Santo S, Buchetti B, Sanguigni V, Brunelli A, Violi F: Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006 Jun;20(8):1082-9. [16770007 ]
  11. Tsuchiya H, Sato M, Kato H, Okubo T, Juneja LR, Kim M: Simultaneous determination of catechins in human saliva by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):253-8. [9448083 ]
  12. Lotito SB, Fraga CG: Ascorbate protects (+)-catechin from oxidation both in a pure chemical system and human plasma. Biol Res. 2000;33(2):151-7. [15693282 ]
  13. Filipe P, Silva JN, Haigle J, Freitas JP, Fernandes A, Santus R, Morliere P: Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic. Photochem Photobiol Sci. 2005 May;4(5):420-8. Epub 2005 Apr 5. [15875075 ]
  14. Lotito SB, Fraga CG: (+)-Catechin as antioxidant: mechanisms preventing human plasma oxidation and activity in red wines. Biofactors. 1999;10(2-3):125-30. [10609873 ]
  15. Farivar-Mohseni H, Kandzari SJ, Zaslau S, Riggs DR, Jackson BJ, McFadden DW: Synergistic effects of Cox-1 and -2 inhibition on bladder and prostate cancer in vitro. Am J Surg. 2004 Nov;188(5):505-10. [15546559 ]