Epicatechin-(4beta->6)-epicatechin-(4beta->8)-catechin 3,3'-digallate (CHEM031171)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:26:45 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031171
Identification
Common NameEpicatechin-(4beta->6)-epicatechin-(4beta->8)-catechin 3,3'-digallate
ClassSmall Molecule
DescriptionEpicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-catechin is found in green vegetables. Epicatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate-(4beta->8)-catechin is isolated from Rheum sp.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin 3-O-gallate-(4b->6)-epicatechin 3-O-gallate-(4b->8)-catechinGenerator
Epicatechin 3-O-gallate-(4β->6)-epicatechin 3-O-gallate-(4β->8)-catechinGenerator
Epicatechin 3-O-gallic acid-(4b->6)-epicatechin 3-O-gallic acid-(4b->8)-catechinGenerator
Epicatechin 3-O-gallic acid-(4beta->6)-epicatechin 3-O-gallic acid-(4beta->8)-catechinGenerator
Epicatechin 3-O-gallic acid-(4β->6)-epicatechin 3-O-gallic acid-(4β->8)-catechinGenerator
3-O-Galloylepicatechin-(4beta->6)-3-O-galloylepicatechin-(4beta->8)-catechinHMDB
Epicatechin 3-O-gallate-(4b->6)-epicatechin-3-O-gallate-(4b->8)-catechinHMDB
2-(3,4-Dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-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-trihydroxybenzoic acidGenerator
Epicatechin-(4b->6)-epicatechin-(4b->8)-catechin 3,3'-digallateGenerator
Epicatechin-(4b->6)-epicatechin-(4b->8)-catechin 3,3'-digallic acidGenerator
Epicatechin-(4beta->6)-epicatechin-(4beta->8)-catechin 3,3'-digallic acidGenerator
Epicatechin-(4β->6)-epicatechin-(4β->8)-catechin 3,3'-digallateGenerator
Epicatechin-(4β->6)-epicatechin-(4β->8)-catechin 3,3'-digallic acidGenerator
Chemical FormulaC59H46O26
Average Molecular Mass1170.981 g/mol
Monoisotopic Mass1170.228 g/mol
CAS Registry Number106548-99-6
IUPAC Name2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-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]-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
SMILESOC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C(C1C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC3=C1C(O)=C(C1C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C14)C1=CC(O)=C(O)C=C1)C(O)=C3)C1=CC(O)=C(O)C=C1)=C(O)C=C2O
InChI IdentifierInChI=1S/C59H46O26/c60-24-14-33(68)43-41(15-24)81-53(20-2-5-27(62)31(66)8-20)56(84-58(79)22-10-36(71)49(76)37(72)11-22)47(43)44-35(70)18-42-46(51(44)78)48(45-34(69)17-29(64)25-16-40(75)52(83-55(25)45)19-1-4-26(61)30(65)7-19)57(54(82-42)21-3-6-28(63)32(67)9-21)85-59(80)23-12-38(73)50(77)39(74)13-23/h1-15,17-18,40,47-48,52-54,56-57,60-78H,16H2
InChI KeyOZYIPNROAOYGSW-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
  • 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
  • Benzoate ester
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Catechol
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP4.23ALOGPS
logP7.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
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
Polarizability112.01 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000041-0cfde5681b2a50403d4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-4700034192-f6ea0272e7f3331abb0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3900060141-d8d45799d88aa721ddceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-a54ba9e98334f41832f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v0a-4920100101-e7e85ae93e61c6b82ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-1900310101-fe41ccafcf5f29d94b0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9500000031-0b98663535de3a97fbb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4j-8900010332-a7ee014e93f512880536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wta-3900000010-5af508d24f9cf34cc397Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-2d8beae361bce1aaab8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ikd-3900000000-6124e4515496fb911b0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2930000000-9f1e2b1284f2bae57d2aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0037665
FooDB IDFDB016790
Phenol Explorer IDNot Available
KNApSAcK IDC00009221
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014452
ChEBI IDNot Available
PubChem Compound ID73822580
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.