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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:12:45 UTC
Update Date2020-11-09 23:29:47 UTC
HMDB IDHMDB0037944
Secondary Accession Numbers
  • HMDB37944
Metabolite Identification
Common Name(-)-Epicatechin 3-O-gallate
Description(-)-Epicatechin 3-O-gallate, also known as 3-O-galloylepicatechin or ECG, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epicatechin 3-O-gallate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (-)-Epicatechin 3-O-gallate is a bitter tasting compound. Outside of the human body, (-)-Epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as tea, peppermints, and common grapes and in a lower concentration in grape wines, german camomiles, and sweet cherries (-)-Epicatechin 3-O-gallate has also been detected, but not quantified in, several different foods, such as common walnuts, carrots, european cranberries, rubus (blackberry, raspberry), and pecan nuts. This could make (-)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin.
Structure
Data?1563863113
Synonyms
ValueSource
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallateChEBI
3-Gallate(-)-epicatecholChEBI
3-O-GalloylepicatechinChEBI
ECGChEBI
TeatanninChEBI
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallic acidGenerator
3-Gallic acid(-)-epicatecholGenerator
(-)-Epicatechin 3-O-gallic acidGenerator
(-)-Epicatechin gallateHMDB
(-)-Epicatechin-3-gallateHMDB
(-)-Epicatechin-3-O-gallateHMDB
Epicatechin gallateHMDB
Epicatechin gallate, (2R-cis)-isomerHMDB
Epicatechol, gallateHMDB
L-Epicatechin gallateHMDB
Epicatechin-3-O-gallateHMDB
Epicatechin-3-gallateHMDB
Epicatechin-3-galloyl esterHMDB
Epicatechin 3-gallic acidGenerator
Chemical FormulaC22H18O10
Average Molecular Weight442.376
Monoisotopic Molecular Weight442.08999678
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(-)-epicatechin 3-O-gallate
CAS Registry Number1257-08-5
SMILES
OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChI KeyLSHVYAFMTMFKBA-TZIWHRDSSA-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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point257 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.55ALOGPS
logP3.38ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.76 m³·mol⁻¹ChemAxon
Polarizability41.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0umi-0920000000-718b2102383cc9dc533eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004l-1490224000-de77e2646c7aba3a8defSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-ece704ccdb047a088d28Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-d89b96c676e7c3398d8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0170-0950000000-685c095616785cc82303Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0940200000-84b58b678cc59833a025Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-440ff7c7a589e1c058b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-8f606522637d9033c95fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0098500000-0c0b2ca06b9e49aa356bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0097500000-7a41879feecb968154e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-77ceea44aa3ce7f822f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-7f271696d73430ee7463Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-21da01e01ba7fa12d6cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0920400000-e7005e91544f51f7efe1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0910000000-a428a4e56e1884d5b86aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-d86fe441a677946b2205Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0310900000-98e9c41598a749627127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdl-0913300000-af1ea1d6588fca8f1f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-60192713dbf412058de2Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 128 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 128 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017114
KNApSAcK IDC00008866
Chemspider ID97034
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpicatechin_gallate
METLIN IDNot Available
PubChem Compound107905
PDB IDNot Available
ChEBI ID70255
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .