4',4''-Dimethylepigallocatechin 3-gallate (CHEM041535)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:33:41 UTC
Update Date2016-11-09 01:22:29 UTC
Accession NumberCHEM041535
Identification
Common Name4',4''-Dimethylepigallocatechin 3-gallate
ClassSmall Molecule
Description4'-Methyl-(-)-epigallocatechin 3-(4-methyl-gallate) is a polyphenol metabolite detected in biological fluids (PMID: 20428313).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4'-Methyl-(-)-epigallocatechin 3-(4-methyl-gallic acid)Generator
4',4"-dimethyl-(-)-epigallocatechin 3-gallateHMDB
4',4"-O-dimethylepigallocatechin 3-O-gallateHMDB
4',4''-Di-O-methyl-egcgMeSH, HMDB
4',4''-Di-O-methyl-epigallocatechin-3-gallateMeSH, HMDB
(2R,3R)-2-(3,5-Dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoic acidGenerator
4',4''-Dimethylepigallocatechin 3-gallic acidGenerator
Chemical FormulaC24H22O11
Average Molecular Mass486.425 g/mol
Monoisotopic Mass486.116 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoate
Traditional Name(2R,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,5-dihydroxy-4-methoxybenzoate
SMILESCOC1=C(O)C=C(C=C1O)[C@H]1OC2=CC(O)=CC(O)=C2C[C@H]1OC(=O)C1=CC(O)=C(OC)C(O)=C1
InChI IdentifierInChI=1S/C24H22O11/c1-32-22-15(27)3-10(4-16(22)28)21-20(9-13-14(26)7-12(25)8-19(13)34-21)35-24(31)11-5-17(29)23(33-2)18(30)6-11/h3-8,20-21,25-30H,9H2,1-2H3/t20-,21-/m1/s1
InChI KeyHFWSXNDMKGHKRD-NHCUHLMSSA-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
  • Epigallocatechin
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-methoxybenzoic acid or derivatives
  • Benzoate ester
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Benzoic acid or derivatives
  • Resorcinol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.034 g/LALOGPS
logP2.94ALOGPS
logP3.37ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.71 m³·mol⁻¹ChemAxon
Polarizability47.37 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0913100000-b1ee5a87a91ce8cf97d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-2374019000-4b330e0d39bafe4e054bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901400000-2708af26a40a70e19585Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-9ad719d5a35bf4859ee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-2900000000-3598cfcef946b0dff5d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0201900000-23d594b45a82584ace7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m1-0605900000-f363764df8038df2d150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-0901100000-037cf374b5b3228645e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0301900000-aebeed444611ca2c198aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f80-0811900000-96c5ddcd09aec1f4a693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-029i-2903200000-1b6346a9d488d9b214b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0105900000-256204dbc537960c40eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0905800000-2a2f7075eb023d400c7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-1927300000-e7f9d0e83108d0404989Spectrum
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 IDHMDB0041668
FooDB IDFDB029827
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID28477210
ChEBI IDNot Available
PubChem Compound ID23583136
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.