Procyanidin B2 3-gallate (CHEM023887)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:21:05 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023887
Identification
Common NameProcyanidin B2 3-gallate
ClassSmall Molecule
DescriptionA gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of procyanidin B2.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epicatechin-(4beta->8)-(-)-epicatechin-3-O-gallateChEBI
(-)-Epicatechin-(4b->8)-(-)-epicatechin-3-O-gallateGenerator
(-)-Epicatechin-(4b->8)-(-)-epicatechin-3-O-gallic acidGenerator
(-)-Epicatechin-(4beta->8)-(-)-epicatechin-3-O-gallic acidGenerator
(-)-Epicatechin-(4β->8)-(-)-epicatechin-3-O-gallateGenerator
(-)-Epicatechin-(4β->8)-(-)-epicatechin-3-O-gallic acidGenerator
Procyanidin b2 3-O-gallic acidGenerator
Procyanidin b2 3-gallic acidGenerator
Chemical FormulaC37H30O16
Average Molecular Mass730.625 g/mol
Monoisotopic Mass730.153 g/mol
CAS Registry Number109280-47-9
IUPAC Name(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-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)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C([C@@H]1[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C=C1)=C(O)C=C2O
InChI IdentifierInChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2/t27-,31-,33-,34-,36-/m1/s1
InChI KeyBXWABJPTCUDBMM-QOCBQNCISA-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
  • 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
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 Solubility0.087 g/LALOGPS
logP3.33ALOGPS
logP4.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area287.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity182.27 m³·mol⁻¹ChemAxon
Polarizability70.21 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0in9-0510390800-feb08379d62d393c9bf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0963822100-eff2eaeabd1899fd608dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0972010000-dd71d19c0af6655f5ffbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400031900-724cb0043d0c65a45983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbi-0920022100-ad8151479004ac1e19d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0911000000-735a8e11f1df71bb3bbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03l0-0100055900-29896c6c7238df91139dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gi-0100289700-ffc27760c7cddb84ccf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-1930148400-b75b64e60ce0e79f00f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-e8c2b9bbafb09cac97bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0m29-0200029700-01ed2618dd86e507234aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-0610059100-84b853a1805a15012abcSpectrum
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 IDHMDB0301929
FooDB IDFDB001637
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30785665
ChEBI ID75652
PubChem Compound ID46181828
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17226517