(-)-Epigallocatechin (CHEM021929)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:15:57 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021929
Identification
Common Name(-)-Epigallocatechin
ClassSmall Molecule
DescriptionA flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-3,3',4',5,5',7-FlavanhexolChEBI
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolChEBI
2,3-cis-EpigallocatechinChEBI
EpigallocatecholChEBI
L-EpigallocatechinChEBI
(-)-cis-3,3',4',5,5',7-HexahydroxyflavanHMDB
(-)-cis-3,3',4',5,5',7-HexahydroxyflavaneHMDB
(-)-EpigallocatecholHMDB
Antiscurvy factor C2HMDB
EGCHMDB
EpigallocatechinHMDB, MeSH
l-EpigallocatecholHMDB
Gallocatechol, (2R-trans)-isomerMeSH, HMDB
GallocatecholMeSH, HMDB
Gallocatechol, (2R-cis)-isomerMeSH, HMDB
GallocatechinMeSH, HMDB
(-)-3,3’,4’,5,5’,7-FlavanhexolHMDB
(-)-EpigallocatechinHMDB
(-)-epi-GallocatechinHMDB
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychromanHMDB
(2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triolHMDB
1-epi-3',4',5',5,7-Pentahydroxy-3-flavanolHMDB
1-epi-3’,4’,5’,5,7-Pentahydroxy-3-flavanolHMDB
3,3',4',5,5',7-FlavanhexolHMDB
3,3’,4’,5,5’,7-FlavanhexolHMDB
GalloepicatechinHMDB
epi-GallocatechinHMDB
Chemical FormulaC15H14O7
Average Molecular Mass306.268 g/mol
Monoisotopic Mass306.074 g/mol
CAS Registry Number970-74-1
IUPAC Name(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameepigallocatechin
SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
InChI IdentifierInChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
InChI KeyXMOCLSLCDHWDHP-IUODEOHRSA-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
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen 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 Solubility0.87 g/LALOGPS
logP0.71ALOGPS
logP1.49ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area130.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.98 m³·mol⁻¹ChemAxon
Polarizability29.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0978700000-567c7251027c80e91a01Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0978700000-567c7251027c80e91a01Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0940000000-a9630fe8d1a042f59c2aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0udi-3110049000-8b1040defcae8063c769Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0900000000-4e9ebbe814af2f8c284dSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-05r0-0913000000-be7d3c4d9b40f51414e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0529000000-0036b0386a7ade78fcacSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-702c5a1e065692895b3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-7844ed1a917693a67b37Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c79003b472daf421e492Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-f92cf1606a46a5b16f4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-2026f33ac95d368b5268Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0729000000-fffbd456b9b51c7d0274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-203a6a86214265bc09e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-2900000000-023b154fc2d731ecee10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0219000000-db1826421845ecab1485Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n0-0922000000-86fb5a0b2fc660815604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2910000000-2375ce05cd5da757763cSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDDB03823
HMDB IDHMDB0038361
FooDB IDFDB017700
Phenol Explorer ID127
KNApSAcK IDC00008818
BiGG IDNot Available
BioCyc IDCPD-10411
METLIN IDNot Available
PDB IDEGT
Wikipedia LinkNot Available
Chemspider ID65231
ChEBI ID42255
PubChem Compound ID72277
Kegg Compound IDC12136
YMDB IDYMDB01682
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10775337
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19653629
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19937856
4. Cooper R, Morre DJ, Morre DM: Medicinal benefits of green tea: part II. review of anticancer properties. J Altern Complement Med. 2005 Aug;11(4):639-52.
5. Lin SC, Wang CP, Chen YM, Lu SY, Fann MJ, Liu CJ, Kao SY, Chang KW: Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes. J Pathol. 2002 Nov;198(3):317-25.
6. Davies SL, Bozzo J: Spotlight on tNOX: a tumor-selective target for cancer therapies. Drug News Perspect. 2006 May;19(4):223-5.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.