You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:39:47 UTC
Update Date2018-05-20 20:41:49 UTC
HMDB IDHMDB0038361
Secondary Accession Numbers
  • HMDB38361
Metabolite Identification
Common Name(-)-Epigallocatechin
DescriptionEpigallocatechin, also known as EGC, 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. Epigallocatechin exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Epigallocatechin has been primarily detected in urine. Within the cell, epigallocatechin is primarily located in the cytoplasm. Epigallocatechin exists in all eukaryotes, ranging from yeast to humans. Epigallocatechin is also a parent compound for other transformation products, including but not limited to, (+)-catechin-(4alpha->8)-(-)-epigallocatechin, (-)-epigallocatechin-(4beta->8)-(-)-epicatechin, and (-)-epicatechin-(4beta->8)-(-)-epigallocatechin. Epigallocatechin is a bitter tasting compound that can be found in a number of food items such as european plum, common grape, cocoa bean, and red raspberry. This makes epigallocatechin a potential biomarker for the consumption of these food products.
Structure
Thumb
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
L-EpigallocatecholHMDB
Chemical FormulaC15H14O7
Average Molecular Weight306.2675
Monoisotopic Molecular Weight306.073952802
IUPAC Name(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameepigallocatechin
CAS Registry Number970-74-1
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of organic compounds known as epigallocatechins. These 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
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Pyrogallol derivative
  • Benzenetriol
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0978700000-567c7251027c80e91a01View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0978700000-567c7251027c80e91a01View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0940000000-a9630fe8d1a042f59c2aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0udi-3110049000-8b1040defcae8063c769View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0900000000-4e9ebbe814af2f8c284dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-05r0-0913000000-be7d3c4d9b40f51414e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0529000000-0036b0386a7ade78fcacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-702c5a1e065692895b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-7844ed1a917693a67b37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00p0-0951000000-95142c4b42b35c4bdac9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c79003b472daf421e492View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-f92cf1606a46a5b16f4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-2026f33ac95d368b5268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0729000000-fffbd456b9b51c7d0274View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-203a6a86214265bc09e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-2900000000-023b154fc2d731ecee10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0219000000-db1826421845ecab1485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n0-0922000000-86fb5a0b2fc660815604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2910000000-2375ce05cd5da757763cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 127 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 127 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 127 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 127 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID127
FoodDB IDFDB017700
KNApSAcK IDC00008818
Chemspider ID65231
KEGG Compound IDC12136
BioCyc IDCPD-10411
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72277
PDB IDEGT
ChEBI ID42255
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16131288 ]
  2. 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. [PubMed:12375264 ]
  3. Davies SL, Bozzo J: Spotlight on tNOX: a tumor-selective target for cancer therapies. Drug News Perspect. 2006 May;19(4):223-5. [PubMed:16823496 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .