Proanthocyanidin B2 3,3'-digallate (CHEM031388)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:36:51 UTC
Update Date2016-11-09 01:19:15 UTC
Accession NumberCHEM031388
Identification
Common NameProanthocyanidin B2 3,3'-digallate
ClassSmall Molecule
Description3,3'-Digalloylprocyanidin B2 is found in common grape. 3,3'-Digalloylprocyanidin B2 is isolated from Rheum rhizome and Thea sinensis (tea).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-Galloylepicatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Proanthocyanidin b2 3,3'-O-gallateHMDB
Procyanidin b2 3,3'-di-O-gallateHMDB
Procyanidin b2-3,3'-di-O-gallateMeSH, HMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4R)-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-trihydroxybenzoic acidGenerator
Proanthocyanidin b2 3,3'-digallic acidGenerator
Chemical FormulaC44H34O20
Average Molecular Mass882.729 g/mol
Monoisotopic Mass882.164 g/mol
CAS Registry Number79907-44-1
IUPAC Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-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 Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-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
SMILESOC1=CC(O)=C2[C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1)C1=C2O[C@@H]([C@@H](CC2=C(O)C=C1O)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
InChI KeyKTLUHRSHFRODPS-RIQPQZJCSA-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
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-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
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen 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 Solubility0.11 g/LALOGPS
logP3.9ALOGPS
logP6.28ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area354.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity218.04 m³·mol⁻¹ChemAxon
Polarizability83.51 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, Positivesplash10-0h0r-0510090450-397db369cb5854acd45fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0941260210-03ac03f6d42738a5f198Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0981110010-928d1c64ced9334e4260Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0300000390-b8be6162d05537078f36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-0903100430-a69a03fb5779753ab28eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0900001000-34b545b4afc98d2d4ec1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0043-0090600580-bda7af02a32c22ca6e1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0200000690-3409a8495fb4fdaf7304Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000360-9b9ea0ecf9a2af888ffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-0100003980-43ce8ef4caabdf963579Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0210311390-530307e1a46cd4e3d7c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rr-0400040590-7b1370f207f6cbff3c2cSpectrum
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 IDHMDB0037967
FooDB IDFDB017141
Phenol Explorer IDNot Available
KNApSAcK IDC00009213
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110532
ChEBI IDNot Available
PubChem Compound ID124016
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.