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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:42:27 UTC
Update Date2019-07-23 06:29:09 UTC
HMDB IDHMDB0039297
Secondary Accession Numbers
  • HMDB39297
Metabolite Identification
Common Name(-)-Epigallocatechin 3,3'-di-gallate
Description(-)-Epigallocatechin 3,3'-di-gallate, also known as 3,3'-di-O-galloylepigallocatechin, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epigallocatechin 3,3'-di-gallate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Epigallocatechin 3,3'-di-gallate has been detected, but not quantified in, tea. This could make (-)-epigallocatechin 3,3'-di-gallate a potential biomarker for the consumption of these foods.
Structure
Data?1563863349
Synonyms
ValueSource
(-)-Epigallocatechin 3,3'-di-gallic acidGenerator
(-)-Epigallocatechin 3,3'-di-O-gallateHMDB
3,3'-Di-O-galloylepigallocatechinHMDB
Epigallocatechin 3,3'-di-gallateHMDB
Epigallocatechin 3,3'-di-O-gallateHMDB
Epigallocatechin 3,3',-di-O-gallic acidGenerator
Epigallocatechin 3,3'-digallic acidGenerator
Chemical FormulaC29H22O15
Average Molecular Weight610.476
Monoisotopic Molecular Weight610.095870034
IUPAC Name(2R,3R)-2-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)phenyl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R)-2-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)phenyl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number89013-66-1
SMILES
OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C(O)C(O)=C2)C(O)=C1
InChI Identifier
InChI=1S/C29H22O15/c30-13-7-15(31)14-9-23(44-29(41)12-4-18(34)25(38)19(35)5-12)27(42-21(14)8-13)10-1-20(36)26(39)22(6-10)43-28(40)11-2-16(32)24(37)17(33)3-11/h1-8,23,27,30-39H,9H2/t23-,27-/m1/s1
InChI KeyLGGSDHMXURUIDJ-YIXXDRMTSA-N
Chemical Taxonomy
Description 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
  • Hydrolyzable tannin
  • Epigallocatechin
  • Depside backbone
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Tannin
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Phenol ester
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility0.043 g/LALOGPS
logP3.12ALOGPS
logP4.78ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area264.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity147.51 m³·mol⁻¹ChemAxon
Polarizability57.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900300000-a8d893e32e4ac92ed746Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-1900021000-77f3cf8c7ffa70b81b33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pc-0900313000-9af616f9f0ac0e76d1ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uki-0900100000-6cad809777481f3f10e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-1900000000-c45acfe904d69c356a8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0400219000-61e4ecadc0e92a6dfa50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0axr-0911832000-f0b5a62ab91fea906168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0901000000-b90224d2e63ca510f02dSpectrum
Biological Properties
Cellular Locations
  • Membrane
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
FooDB IDFDB018843
KNApSAcK IDC00008888
Chemspider ID410664
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound467300
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.. .