Record Information
Version1.0
Creation date2010-04-08 22:04:27 UTC
Update date2017-04-03 04:51:50 UTC
Primary IDFDB000123
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProdelphinidin trimer C-GC-C
DescriptionNot Available
CAS Number99-76-3
Structure
Thumb
Synonyms
SynonymSource
C-GC-Cdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.36 mg/mLALOGPS
logP3.1ALOGPS
logP3.83ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.45ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area371.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity222.98 m3·mol-1ChemAxon
Polarizability88.26 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H38O20
IUPAC name(2R,3S,4R)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C45H38O20/c46-16-8-21(50)31-30(9-16)63-42(14-4-25(54)37(59)26(55)5-14)39(61)35(31)33-23(52)12-24(53)34-36(40(62)43(65-45(33)34)15-6-27(56)38(60)28(57)7-15)32-22(51)11-19(48)17-10-29(58)41(64-44(17)32)13-1-2-18(47)20(49)3-13/h1-9,11-12,29,35-36,39-43,46-62H,10H2/t29-,35-,36+,39-,40-,41+,42+,43+/m0/s1
InChI KeyRJFFPCHJOFXZQD-YTSXHMEESA-N
Isomeric SMILES[H][C@]1(O)CC2=C(O[C@]1([H])C1=CC(O)=C(O)C=C1)C(=C(O)C=C2O)[C@]1([H])C2=C(O)C=C(O)C(=C2O[C@]([H])(C2=CC(O)=C(O)C(O)=C2)[C@@]1([H])O)[C@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC(O)=C(O)C(O)=C2)[C@@]1([H])O
Average Molecular Weight898.779
Monoisotopic Molecular Weight898.195643624
Classification
DescriptionThis compound belongs to the class of organic compounds known as proanthocyanidins. These are molecules containing an oligomeric moiety of C4-C8 and/or C4-C6 and/or C2-C7 oligo/polymers of flavan-3-ols.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassProanthocyanidins
Direct ParentProanthocyanidins
Alternative Parents
Substituents
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Epigallocatechin
  • Catechin
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • Flavan
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID192
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. McMurrough I, Madigan D, Smyth MR. Semipreparative Chromatographic Procedure for the Isolation of Dimeric and Trimeric Proanthocyanidins from Barley. J. Agric. Food Chem. 1996;44(7):1731-1735. [Isolation]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.