Epicatechin 3-(3-methylgallate) (CHEM031367)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:35:50 UTC
Update Date2016-11-09 01:19:15 UTC
Accession NumberCHEM031367
Identification
Common NameEpicatechin 3-(3-methylgallate)
ClassSmall Molecule
DescriptionA gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epicatechin 3-(3'-O-methylgallate)ChEBI
(-)-Epicatechin 3-O-(3'-O-methylgallate)ChEBI
Epicatechin 3-(3'-O-methylgallate)ChEBI
(-)-Epicatechin 3-(3'-O-methylgallic acid)Generator
(-)-Epicatechin 3-O-(3'-O-methylgallic acid)Generator
Epicatechin 3-(3'-O-methylgallic acid)Generator
Epicatechin 3-O-(3-O-methylgallic acid)Generator
3-O-(3-Methylgalloyl)epicatechinHMDB
Epicatechin 3-(3-O-methylgallate)MeSH, HMDB
Epicatechin 3-O-(3-O-methylgallate)ChEBI
Epicatechin 3-(3-methylgallic acid)Generator
Chemical FormulaC23H20O10
Average Molecular Mass456.399 g/mol
Monoisotopic Mass456.106 g/mol
CAS Registry Number83104-86-3
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate
Traditional Name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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=C1)C=C(O)C=C2O
InChI IdentifierInChI=1S/C23H20O10/c1-31-19-6-11(5-17(28)21(19)29)23(30)33-20-9-13-15(26)7-12(24)8-18(13)32-22(20)10-2-3-14(25)16(27)4-10/h2-8,20,22,24-29H,9H2,1H3/t20-,22-/m1/s1
InChI KeyXGTBMCGGGJLOPS-IFMALSPDSA-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
  • 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
  • Methoxyphenol
  • 1-benzopyran
  • Benzoic acid or derivatives
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility0.028 g/LALOGPS
logP2.86ALOGPS
logP3.53ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.25 m³·mol⁻¹ChemAxon
Polarizability44.06 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, Positivesplash10-01bi-0920000000-b51513c9dfb5e293aac8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1340109000-700022084225bff8ec4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920400000-80860baf9e8ba6ee5465Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0910100000-af3d16871d4ac72ce1e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-d190f1915ae7dca82e07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0310900000-924351b5e510ca79ca10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-067r-0913500000-be4e61640d346d602bbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05s0-0900000000-c74eebcd13aea8810eb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-6ee1368a77d0bbee6f96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-1091-0916800000-da6cc070e5cc13dbc904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uei-0409400000-4b90b273229ea6417364Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0670-0506900000-eff006fdf560fcb29c8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dr-0933300000-61f873e6159f83b015ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-0942100000-2f317cd5b9691d0f8c7cSpectrum
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 IDHMDB0037945
FooDB IDFDB017115
Phenol Explorer IDNot Available
KNApSAcK IDC00008869
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID410661
ChEBI ID136553
PubChem Compound ID21146793
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19353533
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.