Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate (CHEM033092)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:55:31 UTC
Update Date2016-11-09 01:20:50 UTC
Accession NumberCHEM033092
Identification
Common NameEpigallocatechin-(4beta->6)-epicatechin 3,3'-digallate
ClassSmall Molecule
DescriptionEpigallocatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate is found in tea. Tannin constituent of oolong tea Camellia sinensis var. viridis.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epigallocatechin 3-O-gallate-(4b->6)-epicatechin 3-O-gallateGenerator
Epigallocatechin 3-O-gallate-(4β->6)-epicatechin 3-O-gallateGenerator
Epigallocatechin 3-O-gallic acid-(4b->6)-epicatechin 3-O-gallic acidGenerator
Epigallocatechin 3-O-gallic acid-(4beta->6)-epicatechin 3-O-gallic acidGenerator
Epigallocatechin 3-O-gallic acid-(4β->6)-epicatechin 3-O-gallic acidGenerator
3-O-Galloylepigallocatechin-(4beta->6)-epicatechin-3-O-gallateHMDB
Epigallocatechin 3-O-gallate(4b->6)-epicatechin 3-O-gallateHMDB
(2R,3R)-6-[(2R,3R,4S)-5,7-Dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Epigallocatechin-(4b->6)-epicatechin 3,3'-digallateGenerator
Epigallocatechin-(4b->6)-epicatechin 3,3'-digallic acidGenerator
Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallic acidGenerator
Epigallocatechin-(4β->6)-epicatechin 3,3'-digallateGenerator
Epigallocatechin-(4β->6)-epicatechin 3,3'-digallic acidGenerator
Chemical FormulaC44H34O21
Average Molecular Mass898.728 g/mol
Monoisotopic Mass898.159 g/mol
CAS Registry Number126715-92-2
IUPAC Name(2R,3R,4S)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R,4S)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-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(O)=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=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(15-4-24(50)37(57)25(51)5-15)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)14-1-2-20(46)21(47)3-14)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 KeyKRHJUZZZEMFSIW-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 Solubility0.17 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
Polarizability85.95 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, Positivesplash10-002b-0510190550-e441f0565a2bdd01470bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0961450210-af17d13114afde04df82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0980100000-72b028d2cdad23c19828Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0300100390-756d61e8616c22c52d83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-0914300440-0e2b9ef4e352dd0d548aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0901000100-31008d3364cef8d68f0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fmj-0100004930-efbcb5c7ca6701932b72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-0200220890-d48573c4cb345705486aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0096-0400030590-9f8f30d161ef6da87295Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010000790-7f95aac19777900f86afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0700010980-6569ed302a8ea72bc972Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-0400010390-7fc91c8eb95ebb5203aeSpectrum
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 IDHMDB0039772
FooDB IDFDB019420
Phenol Explorer IDNot Available
KNApSAcK IDC00009230
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9832739
ChEBI IDNot Available
PubChem Compound ID11658004
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.