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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:40:35 UTC
Update Date2022-03-07 02:55:44 UTC
HMDB IDHMDB0038371
Secondary Accession Numbers
  • HMDB38371
Metabolite Identification
Common Nameent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate
Descriptionent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 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''. ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate has been detected, but not quantified in, fruits. This could make ent-epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate.
Structure
Data?1563863186
Synonyms
ValueSource
ent-Epicatechin-(4a->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallateGenerator
ent-Epicatechin-(4a->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallic acidGenerator
ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallic acidGenerator
ent-Epicatechin-(4α->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallateGenerator
ent-Epicatechin-(4α->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4beta->8)-3-O-galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Procyanidin C1 3',3''-di-O-gallateHMDB
2-(3,4-Dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-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->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallateGenerator
Epicatechin-(4b->8)-ent-epicatechin-(4a->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4beta->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallic acidGenerator
Epicatechin-(4β->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallateGenerator
Epicatechin-(4β->8)-ent-epicatechin-(4α->8)-ent-epicatechin 3',3''-digallic acidGenerator
Chemical FormulaC59H46O26
Average Molecular Weight1170.9809
Monoisotopic Molecular Weight1170.227731644
IUPAC Name2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
CAS Registry Number106533-61-3
SMILES
OC1C(OC2=CC(O)=CC(O)=C2C1C1=C2OC(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(C3=C(O)C=C(O)C4=C3OC(C(C4)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC(O)=C(O)C=C3)C2=C(O)C=C1O)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C59H46O26/c60-24-14-33(68)43-41(15-24)81-53(20-2-5-27(62)31(66)8-20)51(78)47(43)44-35(70)18-36(71)46-48(57(85-59(80)23-12-39(74)50(77)40(75)13-23)54(84-56(44)46)21-3-6-28(63)32(67)9-21)45-34(69)17-29(64)25-16-42(82-58(79)22-10-37(72)49(76)38(73)11-22)52(83-55(25)45)19-1-4-26(61)30(65)7-19/h1-15,17-18,42,47-48,51-54,57,60-78H,16H2
InChI KeyCSQVLCNLSUIXDX-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
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin gallate
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.28 g/LALOGPS
logP4.25ALOGPS
logP7.61ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area464.66 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity290.55 m³·mol⁻¹ChemAxon
Polarizability111.39 ųChemAxon
Number of Rings11ChemAxon
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]+331.77330932474
DeepCCS[M-H]-330.04930932474
DeepCCS[M-2H]-364.08130932474
DeepCCS[M+Na]+338.10230932474
AllCCS[M+H]+310.032859911
AllCCS[M+H-H2O]+310.732859911
AllCCS[M+NH4]+309.432859911
AllCCS[M+Na]+309.132859911
AllCCS[M-H]-310.532859911
AllCCS[M+Na-2H]-316.032859911
AllCCS[M+HCOO]-322.132859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 10V, Positive-QTOFsplash10-0uxr-5800000090-a3febf930788e2295eff2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 20V, Positive-QTOFsplash10-0f92-4800053692-b64d0831842e157343612015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 40V, Positive-QTOFsplash10-0udj-1800093260-193e3ed96ce76b469a832015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 10V, Negative-QTOFsplash10-014i-2900000000-eabc7f3469d3847a48792015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 20V, Negative-QTOFsplash10-0ftu-4911200211-5122fbbb04ac8de342492015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 40V, Negative-QTOFsplash10-002r-1940000000-0c3d556c2aea45c437f62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 10V, Negative-QTOFsplash10-014i-2900000004-be9723a2b4699f2adacd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 20V, Negative-QTOFsplash10-0wmm-5900000001-d14a35e98db9a51a2b8d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 40V, Negative-QTOFsplash10-004i-2901100000-013b032a0da88764fd502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 10V, Positive-QTOFsplash10-0w90-9800000020-3c5802e7b527a83319e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 20V, Positive-QTOFsplash10-0ukc-4910100020-6e0da4a7fcfc771beafd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin-(4alpha->8)-ent-epicatechin 3',3''-digallate 40V, Positive-QTOFsplash10-0fk9-5910000030-3f309ce8494cf5777d212021-09-24Wishart 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 IDFDB021146
KNApSAcK IDC00009228
Chemspider ID35014555
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73822578
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.. .