Epicatechin-(4beta->6)-epigallocatechin 3,3'-digallate (CHEM032633)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:35:09 UTC
Update Date2016-11-09 01:20:45 UTC
Accession NumberCHEM032633
Identification
Common NameEpicatechin-(4beta->6)-epigallocatechin 3,3'-digallate
ClassSmall Molecule
DescriptionEpicatechin 3-O-gallate-(4beta->6)-epigallocatechin 3-O-gallate is found in tea. Epicatechin 3-O-gallate-(4beta->6)-epigallocatechin 3-O-gallate is isolated from oolong tea Camellia sinensis var. viridis.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin 3-O-gallate-(4b->6)-epigallocatechin 3-O-gallateGenerator
Epicatechin 3-O-gallate-(4β->6)-epigallocatechin 3-O-gallateGenerator
Epicatechin 3-O-gallic acid-(4b->6)-epigallocatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4beta->6)-epigallocatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4β->6)-epigallocatechin 3-O-gallic acidGenerator
3-O-Galloylepicatechin-(4beta->6)-epigallocatechin-3-O-gallateHMDB
Epicatechin 3-O-gallate (4b->6)epigallocatechin 3-O-gallateHMDB
(2R,3R)-6-[(2R,3R,4S)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Epicatechin-(4b->6)-epigallocatechin 3,3'-digallateGenerator
Epicatechin-(4b->6)-epigallocatechin 3,3'-digallic acidGenerator
Epicatechin-(4beta->6)-epigallocatechin 3,3'-digallic acidGenerator
Epicatechin-(4β->6)-epigallocatechin 3,3'-digallateGenerator
Epicatechin-(4β->6)-epigallocatechin 3,3'-digallic acidGenerator
Chemical FormulaC44H34O21
Average Molecular Mass898.728 g/mol
Monoisotopic Mass898.159 g/mol
CAS Registry Number126715-91-1
IUPAC Name(2R,3R,4S)-4-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R,4S)-4-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
SMILESOC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC(O)=C(O)C(O)=C3)C=C2O)C(O)=C1
InChI IdentifierInChI=1S/C44H34O21/c45-18-10-22(48)33-31(11-18)63-41(14-1-2-20(46)21(47)3-14)42(65-44(61)17-8-28(54)39(59)29(55)9-17)35(33)34-23(49)13-30-19(36(34)56)12-32(40(62-30)15-4-24(50)37(57)25(51)5-15)64-43(60)16-6-26(52)38(58)27(53)7-16/h1-11,13,32,35,40-42,45-59H,12H2/t32-,35-,40-,41-,42-/m1/s1
InChI KeyMCKUYLHAXMDCFO-XREIVNNOSA-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
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-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
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • Catechol
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.16 g/LALOGPS
logP3.76ALOGPS
logP5.98ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area374.51 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity220.02 m³·mol⁻¹ChemAxon
Polarizability85.94 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-004j-0510190450-e6b942111246a9f97b4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfu-0960341110-557fe17c88d4c03ea1f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0980110000-df016723e310d7b69deaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0300100390-37f38f22051fe915ce3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0914300440-0e3f87c560dddae5b267Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0900000100-b01b78e4aa5293fd618dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fis-0100003950-a781e150033f9a64827dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0200221980-b70702152415c3d1188eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001d-0800122490-f59aa66e6abf8a2dae70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000490-e1e3312dcb8bf1a94262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0600010890-bb1f29ece6df1bc9c7c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p3-0300010190-2b28d53c2185a35dea96Spectrum
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 IDHMDB0039302
FooDB IDFDB018848
Phenol Explorer IDNot Available
KNApSAcK IDC00009217
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777343
ChEBI ID169229
PubChem Compound ID101834717
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.