You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-12 01:49:35 UTC
Update Date2016-02-11 03:34:31 UTC
HMDB IDHMDB40293
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Epigallocatechin 3-(4-methyl-gallate)
Description(-)-Epigallocatechin 3-(4-methyl-gallate) is found in tea. (-)-Epigallocatechin 3-(4-methyl-gallate) is a constituent of oolong tea (Camellia sinensis).
Structure
Thumb
Synonyms
ValueSource
3-O-(4-O-Methylgalloyl)epigallocatechinHMDB
4"-methyl-(-)-epigallocatechin 3-gallateHMDB
4''-O-Methylepigallocatechin 3-O-gallateHMDB
Epigallocatechin 3-(4-methylgallate)HMDB
Epigallocatechin 3-O-(4-methylgallate)HMDB
Chemical FormulaC23H20O11
Average Molecular Weight472.3983
Monoisotopic Molecular Weight472.100561482
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoate
Traditional Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(C=C1O)C(=O)O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1/C23H20O11/c1-32-22-16(28)4-10(5-17(22)29)23(31)34-19-8-12-13(25)6-11(24)7-18(12)33-21(19)9-2-14(26)20(30)15(27)3-9/h2-7,19,21,24-30H,8H2,1H3/t19-,21-/s2
InChI KeyInChIKey=BMJHAAZDURGGSC-VCZXBEBONA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechin gallates
Alternative Parents
Substituents
  • Catechin gallate
  • Epigallocatechin
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Gallic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Chromane
  • Benzoate ester
  • Pyrogallol derivative
  • Benzylether
  • Benzoic acid or derivatives
  • Benzenetriol
  • Methoxybenzene
  • Resorcinol
  • Phenol ether
  • 1,2-diphenol
  • Benzoyl
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Food
Biofunction
  • Nutrient
Application
  • Nutrient
Cellular locations
  • Membrane
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 Solubility0.051 mg/mLALOGPS
logP2.65ALOGPS
logP3.22ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.57ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.23 m3·mol-1ChemAxon
Polarizability45.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 774
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 774
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID774
FoodDB IDFDB020014
KNApSAcK IDNot Available
Chemspider ID355453
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB40293
Metagene LinkHMDB40293
METLIN IDNot Available
PubChem Compound401129
PDB IDNot Available
ChEBI 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.