Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:55:13 UTC
Update Date2022-03-07 02:55:27 UTC
HMDB IDHMDB0037664
Secondary Accession Numbers
  • HMDB37664
Metabolite Identification
Common NameEpicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate
DescriptionEpicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 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''. Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate has been detected, but not quantified in, green vegetables. This could make epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate.
Structure
Data?1563863069
Synonyms
ValueSource
Epicatechin 3-O-gallate-(4b->6)-epicatechin 3-O-gallate-(4b->8)-epicatechin 3-O-gallateGenerator
Epicatechin 3-O-gallate-(4β->6)-epicatechin 3-O-gallate-(4β->8)-epicatechin 3-O-gallateGenerator
Epicatechin 3-O-gallic acid-(4b->6)-epicatechin 3-O-gallic acid-(4b->8)-epicatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4beta->6)-epicatechin 3-O-gallic acid-(4beta->8)-epicatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4β->6)-epicatechin 3-O-gallic acid-(4β->8)-epicatechin 3-O-gallic acidGenerator
3-O-Galloylepicatechin-(4beta->6)-3-O-galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
2-(3,4-Dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Epicatechin-(4b->6)-epicatechin-(4b->8)-epicatechin 3,3',3''-trigallateGenerator
Epicatechin-(4b->6)-epicatechin-(4b->8)-epicatechin 3,3',3''-trigallic acidGenerator
Epicatechin-(4beta->6)-epicatechin-(4beta->8)-epicatechin 3,3',3''-trigallic acidGenerator
Epicatechin-(4β->6)-epicatechin-(4β->8)-epicatechin 3,3',3''-trigallateGenerator
Epicatechin-(4β->6)-epicatechin-(4β->8)-epicatechin 3,3',3''-trigallic acidGenerator
Chemical FormulaC66H50O30
Average Molecular Weight1323.0852
Monoisotopic Molecular Weight1322.23869026
IUPAC Name2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-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)-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number106533-64-6
SMILES
OC1=CC(O)=C2C(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC2=C1)C1=CC(O)=C(O)C=C1)C1=C(O)C2=C(OC(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C2C2=C(O)C=C(O)C3=C2OC(C(C3)OC(=O)C2=CC(O)=C(O)C(O)=C2)C2=CC(O)=C(O)C=C2)C2=CC(O)=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C66H50O30/c67-27-16-36(75)48-45(17-27)91-59(22-2-5-30(69)34(73)8-22)62(95-65(89)25-12-41(80)55(85)42(81)13-25)52(48)49-38(77)20-46-51(57(49)87)53(63(60(92-46)23-3-6-31(70)35(74)9-23)96-66(90)26-14-43(82)56(86)44(83)15-26)50-37(76)19-32(71)28-18-47(93-64(88)24-10-39(78)54(84)40(79)11-24)58(94-61(28)50)21-1-4-29(68)33(72)7-21/h1-17,19-20,47,52-53,58-60,62-63,67-87H,18H2
InChI KeyMHDUITHKUVVZLK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin gallate
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Tricarboxylic acid or derivatives
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Catechol
  • Benzoyl
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP4.62ALOGPS
logP9.19ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.64ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count21ChemAxon
Polar Surface Area531.42 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity326.31 m³·mol⁻¹ChemAxon
Polarizability126.16 ųChemAxon
Number of Rings12ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+335.92430932474
DeepCCS[M-H]-334.20730932474
DeepCCS[M-2H]-368.23830932474
DeepCCS[M+Na]+342.08130932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 10V, Positive-QTOFsplash10-0uxr-7903000012-a2308a172f1286e84ef32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 20V, Positive-QTOFsplash10-0uea-9510003065-28308d43cdf7ea5718552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 40V, Positive-QTOFsplash10-00kb-9500007135-1aa59e13c941be144d802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 10V, Negative-QTOFsplash10-00xr-0918000010-11d39eb09d3f1cbcc9e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 20V, Negative-QTOFsplash10-0gb9-0902100110-9e037bf786424de448412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 40V, Negative-QTOFsplash10-016u-0900200000-5cb6c7a9a6df2eeda11f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 10V, Positive-QTOFsplash10-0mb9-3947000000-7ab6f7d42f388c8575462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 20V, Positive-QTOFsplash10-01b9-0795000250-51fc30060c017252f10e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 40V, Positive-QTOFsplash10-0311-0392000212-059293e83638274872d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 10V, Negative-QTOFsplash10-00di-0309000000-7c091bd9059e935fe1cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 20V, Negative-QTOFsplash10-0udi-0973000000-f9b7e859760dc0038b482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate 40V, Negative-QTOFsplash10-00or-2970000000-9fbd4d4430d24bc1eff22021-09-22Wishart LabView Spectrum
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 IDNot Available
FooDB IDFDB016788
KNApSAcK IDC00009222
Chemspider ID35014451
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73822577
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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
Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-epicatechin 3-O-gallate → Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-catechindetails