Survey with prize
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:14:05 UTC
Update Date2019-01-11 19:54:34 UTC
HMDB IDHMDB0037965
Secondary Accession Numbers
  • HMDB37965
Metabolite Identification
Common Nameent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate
Descriptionent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate is found in fruits. ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate is a constituent of Byrsonima crassifolia (nance).
Structure
Data?1547236474
Synonyms
ValueSource
3-Galloylprocyanidin b1HMDB
Procyanidin dimer b1 3-O-gallateHMDB
Chemical FormulaC37H30O16
Average Molecular Weight730.6245
Monoisotopic Molecular Weight730.153384912
IUPAC Name2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry NumberNot Available
SMILES
OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2
InChI KeyBXWABJPTCUDBMM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • B-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin gallate
  • Catechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Benzoyl
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.087 g/LALOGPS
logP3.33ALOGPS
logP4.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area287.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity182.27 m³·mol⁻¹ChemAxon
Polarizability69.9 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w4i-0900030100-12cb7c59426319aa7026JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0in9-0610390800-81623953ceca8f3ecad3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0953821100-fcafbea2f9d2cea070e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0972010000-8a5bb4d6b0534651ba29JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0in9-0610390800-81623953ceca8f3ecad3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0953821100-fcafbea2f9d2cea070e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0972010000-8a5bb4d6b0534651ba29JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0in9-0610390800-81623953ceca8f3ecad3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0953821100-fcafbea2f9d2cea070e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0972010000-8a5bb4d6b0534651ba29JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400020900-15c1d892670c625835a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbi-0920012100-f4b930a3016c013db44aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0911000000-9862fd11a465aba5dcb1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400020900-15c1d892670c625835a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbi-0920012100-f4b930a3016c013db44aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0911000000-9862fd11a465aba5dcb1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400020900-15c1d892670c625835a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbi-0920012100-f4b930a3016c013db44aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0911000000-9862fd11a465aba5dcb1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID172
FoodDB IDFDB017143
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12795889
PDB IDNot Available
ChEBI IDNot Available
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.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate → ent-Epicatechin(4alpha->8)catechindetails
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3,3'-digallate → ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallatedetails