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Showing Compound Prodelphinidin trimer GC-C-C (FDB000122)

Record Information
Version1.0
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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
GC-C-Cdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity222.98 m³·mol⁻¹ChemAxon
Polarizability88.26 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
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
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
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
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0100000970-3843eab241d0865e909e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0200044910-588eb85c8b1b499c482d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-0100090600-3669222e3f9d48b050fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0100000290-29a2d61fe0ed5cf242622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0931120210-d82bc08080e96ea435672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0905200100-ba9ff47cc9ac75bfbf3d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-303dbcf327aa16128f112021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0000000390-0520a3c3c5eb88df34882021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00g0-0880000390-32c65e0eea00bc7ed4432021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0000000790-bba067a193fe70db9f8b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0121030490-f4e6c8cef889fa2e52f22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06yn-0521001390-3548af2641515760e25e2021-10-21View Spectrum
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
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.