Record Information
Creation date2010-04-08 22:04:26 UTC
Update date2019-11-26 02:54:32 UTC
Primary IDFDB000122
Secondary Accession Numbers
  • FDB000123
Chemical Information
FooDB NameProdelphinidin trimer GC-C-C
DescriptionProdelphinidin trimer gc-c-c is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Prodelphinidin trimer gc-c-c is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Prodelphinidin trimer gc-c-c can be found in beer, which makes prodelphinidin trimer gc-c-c a potential biomarker for the consumption of this food product.
CAS Number99-76-3
Predicted Properties
Water Solubility0.36 g/LALOGPS
pKa (Strongest Acidic)8.45ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area371.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity222.98 m³·mol⁻¹ChemAxon
Polarizability88.26 ųChemAxon
Number of Rings9ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
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
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
  • C-type proanthocyanidin
  • B-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzenetriol
  • Pyrogallol derivative
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0100000970-3843eab241d0865e909eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0200044910-588eb85c8b1b499c482dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-0100090600-3669222e3f9d48b050fbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0100000290-29a2d61fe0ed5cf24262Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0931120210-d82bc08080e96ea43567Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0905200100-ba9ff47cc9ac75bfbf3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-303dbcf327aa16128f11Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0000000390-0520a3c3c5eb88df3488Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00g0-0880000390-32c65e0eea00bc7ed443Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0000000790-bba067a193fe70db9f8bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0121030490-f4e6c8cef889fa2e52f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06yn-0521001390-3548af2641515760e25eSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID191
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
Food Biomarker OntologyNot Available
VMH 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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
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.