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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:38:41 UTC
Update Date2019-07-23 06:23:44 UTC
HMDB IDHMDB0037400
Secondary Accession Numbers
  • HMDB37400
Metabolite Identification
Common Name(+)-Catechin 6-C-glucoside
Description(+)-Catechin 6-C-glucoside, also known as 6-C-glucopyranosylcatechin, belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone (+)-Catechin 6-C-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (+)-Catechin 6-C-glucoside has been detected, but not quantified in, green vegetables. This could make (+)-catechin 6-C-glucoside a potential biomarker for the consumption of these foods.
Structure
Data?1563863024
Synonyms
ValueSource
6-C-GlucopyranosylcatechinHMDB
6-Glucopyranosyl-(+)-catechinHMDB
6-Glucosyl-(+)-catechinHMDB
Chemical FormulaC21H24O11
Average Molecular Weight452.4087
Monoisotopic Molecular Weight452.13186161
IUPAC Name2-(3,4-dihydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name2-(3,4-dihydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry Number105371-27-5
SMILES
OCC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(C(O)C2)C2=CC(O)=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C21H24O11/c22-6-14-17(28)18(29)19(30)21(32-14)15-11(25)5-13-8(16(15)27)4-12(26)20(31-13)7-1-2-9(23)10(24)3-7/h1-3,5,12,14,17-30H,4,6H2
InChI KeyPWMSPKVTJLJDDS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Catechin
  • Flavonoid c-glycoside
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.77 g/LALOGPS
logP-0.64ALOGPS
logP-0.96ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.78ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area200.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity107.12 m³·mol⁻¹ChemAxon
Polarizability44.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-3109300000-2e3407a578c7bf35984eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1400549000-3d3bc28c449b945d7638Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0142900000-8d746a1077f9cb353c7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uei-2896700000-7d8b17efd0cd408493baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-1921100000-0d2a91cf683d65477be0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0112900000-191af36c2ca65cdd5264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4934400000-183477aeb3f38fb5cd64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k95-3920000000-880ca4f155bea3cfedd8Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016444
KNApSAcK IDC00006358
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound59010767
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
(+)-Catechin 6-C-glucoside → 2-(4-hydroxy-3-methoxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-trioldetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
(+)-Catechin 6-C-glucoside → ({6-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
(+)-Catechin 6-C-glucoside → {6-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
(+)-Catechin 6-C-glucoside → {2-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
(+)-Catechin 6-C-glucoside → {2-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
(+)-Catechin 6-C-glucoside → 3,4,5-trihydroxy-6-(2-hydroxy-5-{3,5,7-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-yl}phenoxy)oxane-2-carboxylic aciddetails
(+)-Catechin 6-C-glucoside → 6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
(+)-Catechin 6-C-glucoside → (2-hydroxy-5-{3,5,7-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-yl}phenyl)oxidanesulfonic aciddetails