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Showing Compound Epicatechin-(4beta->8)-epicatechin 3'-gallate (FDB001640)

Record Information
Version1.0
Creation date2010-04-08 22:05:03 UTC
Update date2019-11-26 02:56:37 UTC
Primary IDFDB001640
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpicatechin-(4beta->8)-epicatechin 3'-gallate
DescriptionEpicatechin-(4beta->8)-epicatechin 3'-gallate is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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-(4beta->8)-epicatechin 3'-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin-(4beta->8)-epicatechin 3'-gallate can be synthesized from gallic acid. Epicatechin-(4beta->8)-epicatechin 3'-gallate can also be synthesized into procyanidin B2. Epicatechin-(4beta->8)-epicatechin 3'-gallate can be found in common buckwheat, common grape, and tea, which makes epicatechin-(4beta->8)-epicatechin 3'-gallate a potential biomarker for the consumption of these food products.
CAS Number73086-04-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP3.32ALOGPS
logP4.7ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area287.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity182.27 m³·mol⁻¹ChemAxon
Polarizability68.5 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC37H30O16
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31-,33-,34-,35-/m1/s1
InChI KeyVLFKNLZNDSEVBZ-BTWXELLASA-N
Isomeric SMILESO[C@H]1[C@H](OC2=CC(O)=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](C2)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1
Average Molecular Weight730.6245
Monoisotopic Molecular Weight730.153384912
Classification
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
  • 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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u0-0510940600-86b1b7089e99f624871a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0972511100-dfee234fea53ce5f1e332016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-0691000000-ef5b24d7cb68459abc482016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0300111900-27b6457ff92e592149052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-0923202200-42e7a77963f6441053b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0910000000-749f45a9d688840195ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0100153900-41a928c12f5b41f3c09e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl3-0641916500-1898991c3855716ce9212021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0960344100-9ea07afc55b5ea9c64532021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0300070900-132b4b350214afa8d79b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0900023300-dca9be94836b87320d822021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-2822609100-fffd213c35ea07cc7bb72021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009212
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Black teaExpected but not quantifiedNot AvailableKNAPSACK
Common buckwheatExpected but not quantifiedNot AvailableKNAPSACK
Common grapeExpected but not quantifiedNot AvailableKNAPSACK
Green teaExpected but not quantifiedNot AvailableKNAPSACK
Herbal teaExpected but not quantifiedNot AvailableKNAPSACK
Red teaExpected but not quantifiedNot AvailableKNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.