(-)-Epiafzelechin 3-gallate (CHEM032189)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:12:15 UTC
Update Date2016-11-09 01:19:25 UTC
Accession NumberCHEM032189
Identification
Common Name(-)-Epiafzelechin 3-gallate
ClassSmall Molecule
DescriptionA gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epiafzelechin.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epiafzelechin 3-O-gallateChEBI
Epiafzelechin 3-O-gallateChEBI
(-)-Epiafzelechin 3-O-gallic acidGenerator
Epiafzelechin 3-O-gallic acidGenerator
(-)-Epiafzelechin 3-gallic acidGenerator
(-)-Epiafzelechin gallateChEMBL, HMDB
(-)-Epiafzelechin gallic acidGenerator, HMDB
3-Galloyl-(-)-epiafzelechinHMDB
(-)-Epiafzelechin 3-gallateChEBI
Chemical FormulaC22H18O9
Average Molecular Mass426.373 g/mol
Monoisotopic Mass426.095 g/mol
CAS Registry Number108907-43-3
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Nameepiafzelechin 3-O-gallate
SMILESOC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C2
InChI IdentifierInChI=1S/C22H18O9/c23-12-3-1-10(2-4-12)21-19(9-14-15(25)7-13(24)8-18(14)30-21)31-22(29)11-5-16(26)20(28)17(27)6-11/h1-8,19,21,23-28H,9H2/t19-,21-/m1/s1
InChI KeySDZPYNMXGUHFMZ-TZIWHRDSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavan-3-ols
Alternative Parents
Substituents
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • 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 Solubility0.024 g/LALOGPS
logP2.74ALOGPS
logP3.68ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.78 m³·mol⁻¹ChemAxon
Polarizability41.25 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, Positivesplash10-0ufr-0930000000-49a61f43c54f5b8cd754Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ufr-0900121000-d2ea5029d7ff2cf33f36Spectrum
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, Positivesplash10-002r-0920400000-26bc012ba94e75ded8f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fki-0910000000-9aaf820c6fcff2c0d7adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-3900000000-87d95cedf72475332b66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0310900000-5a0d5da96ff90679f69bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0951300000-e56c605bb0f7c08029a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-1900000000-ebf59da24ada4ffef234Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0150900000-b1a03a175652e31d2043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kbr-0952300000-70aa7b9e2e90c768c2a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0553-1942000000-15d94da7924a9f8adf17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0030900000-8ffa4234223e962af026Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r0-0933400000-484e49d715ff3b9f99d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002u-3913100000-a363bf1373dc138b7f1eSpectrum
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 IDHMDB0038846
FooDB IDFDB018281
Phenol Explorer IDNot Available
KNApSAcK IDC00008864
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID410660
ChEBI ID136552
PubChem Compound ID467295
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=23187287
2.
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.