Epigallocatechin 3-p-coumarate (CHEM031707)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:51:36 UTC
Update Date2016-11-09 01:19:19 UTC
Accession NumberCHEM031707
Identification
Common NameEpigallocatechin 3-p-coumarate
ClassSmall Molecule
Description(-)-Epigallocatechin 3-p-coumaroate is found in tea. (-)-Epigallocatechin 3-p-coumaroate is isolated from leaves of green tea (Thea sinensis).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epigallocatechin 3-p-coumaroic acidGenerator
(-)-Epigallocatechin 3-O-P-coumaroateHMDB
3-O-P-CoumaroylepigallocatechinHMDB
Epigallocatechin 3-O-P-coumarateHMDB
Epigallocatechin 3-O-p-coumaric acidGenerator
Epigallocatechin 3-p-coumaric acidGenerator
Chemical FormulaC24H20O9
Average Molecular Mass452.410 g/mol
Monoisotopic Mass452.111 g/mol
CAS Registry Number89013-65-0
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILESOC1=CC=C(\C=C\C(=O)O[C@@H]2CC3=C(O[C@@H]2C2=CC(O)=C(O)C(O)=C2)C=C(O)C=C3O)C=C1
InChI IdentifierInChI=1S/C24H20O9/c25-14-4-1-12(2-5-14)3-6-22(30)32-21-11-16-17(27)9-15(26)10-20(16)33-24(21)13-7-18(28)23(31)19(29)8-13/h1-10,21,24-29,31H,11H2/b6-3+/t21-,24-/m1/s1
InChI KeyHKPGWUPXXPIOAN-XMTAIGAMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentEpigallocatechins
Alternative Parents
Substituents
  • Epigallocatechin
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.013 g/LALOGPS
logP3.11ALOGPS
logP4.22ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.57ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity117.53 m³·mol⁻¹ChemAxon
Polarizability45 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, Positivesplash10-014s-0920000000-385d357a7f2880a54ad6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-2420139000-14d67c485cb251d30a5aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0911300000-e8b33772e8365a93b3c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059j-0911000000-309416b341b21078f967Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-9d05aa480764ca79d69aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0404900000-df6796aaf0868491bf0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r00-0914200000-c31773809390588e2ff7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ta-0900000000-a916fde482bc1a9042c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0911600000-43c89f38157fb31753dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0910100000-485fd5527eebdd9bb6aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0920200000-bb2e62100283ece93833Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100900000-75df5794ee83db37e5afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fri-0922400000-da2f53ffecbdc68e6393Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2913000000-8e61c28268e1c4e83fabSpectrum
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 IDHMDB0038362
FooDB IDFDB017701
Phenol Explorer IDNot Available
KNApSAcK IDC00008905
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4976697
ChEBI IDNot Available
PubChem Compound ID6474788
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.