Epigallocatechin 3-(3-methylgallate) (CHEM031708)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:51:39 UTC
Update Date2016-11-09 01:19:19 UTC
Accession NumberCHEM031708
Identification
Common NameEpigallocatechin 3-(3-methylgallate)
ClassSmall Molecule
Description(-)-Epigallocatechin 3-(3-methyl-gallate) is found in tea. (-)-Epigallocatechin 3-(3-methyl-gallate) is isolated from green tea (Thea sinensis) and oolong tea (Camellia sinensis).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epigallocatechin 3-(3-methyl-gallic acid)Generator
3-O-(3-O-Methylgalloyl)epigallocatechinHMDB
Epigallocatechin 3-(3-methyl-gallate)HMDB
Epigallocatechin 3-(3-O-methyl-gallate)HMDB
Epigallocatechin 3-O-(3-O-methylgallate)HMDB
Epigallocatechin-3-O-(3''-O-methyl)-gallateMeSH, HMDB
Epigallocatechin 3-O-(3-O-methylgallic acid)Generator
EGCG3''meMeSH
Epigallocatechin 3-(3-methylgallic acid)Generator
Chemical FormulaC23H20O11
Average Molecular Mass472.398 g/mol
Monoisotopic Mass472.101 g/mol
CAS Registry Number83104-87-4
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate
Traditional Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate
SMILESCOC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
InChI IdentifierInChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1
InChI KeyWVRDOLPMKOCJRJ-DENIHFKCSA-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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Tannin
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • M-methoxybenzoic acid or derivatives
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Phenol ether
  • Methoxybenzene
  • Anisole
  • Catechol
  • Phenoxy compound
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP2.66ALOGPS
logP3.22ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.23 m³·mol⁻¹ChemAxon
Polarizability45.05 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-0920000000-5e5ab0ec4c7967465bf1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1230109000-6b178dc40065f0f3e3c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0910400000-85a31cdd283340c1a2fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0910100000-b4374fde3acf214207d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-886bd53b917ddc368075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0301900000-36fddc6b86e792823d41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0913500000-cda8bf3a3292ac048a30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057r-0900000000-a351ce366e3d756f2faeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-0513900000-a8ea9e75925b11d844e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-0933400000-ae8ed72a60d5ca5840abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0912200000-a1694e271d7cd78e3a8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a12cf827574b709971ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0911500000-44b22da3f1b72b3bb2cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-0506900000-a7d37859817344d1b3a4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038363
FooDB IDFDB017703
Phenol Explorer IDNot Available
KNApSAcK IDC00008883
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7980602
ChEBI IDNot Available
PubChem Compound ID9804842
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.