Record Information
Version1.0
Creation date2010-04-08 22:04:25 UTC
Update date2015-07-20 21:30:21 UTC
Primary IDFDB000052
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePinotin A
DescriptionIsol. from red wine incl. Pinotage (CCD)
CAS Number663910-41-6
Structure
Thumb
Synonyms
SynonymSource
Malvidin 3-glucoside-4-vinylcatecholmanual
Malvidin 3-O-glucoside caffeic aciddb_source
Malvidin 3-O-glucoside caffeic adductdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP2.63ALOGPS
logP0.99ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area221.13 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity164.73 m3·mol-1ChemAxon
Polarizability61.84 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC31H29O14
IUPAC name7-(3,4-dihydroxyphenyl)-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
InChI IdentifierInChI=1S/C31H28O14/c1-40-21-6-13(7-22(41-2)25(21)36)29-30(45-31-28(39)27(38)26(37)23(11-32)44-31)15-10-18(12-3-4-16(34)17(35)5-12)42-19-8-14(33)9-20(43-29)24(15)19/h3-10,23,26-28,31-32,37-39H,11H2,1-2H3,(H3-,33,34,35,36)/p+1/t23-,26-,27+,28-,31+/m1/s1
InChI KeyInChIKey=RFTHDRVOYDHSOC-BGXVWEPQSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C(O)=C1)=CC(O)=C2
Average Molecular Weight625.5536
Monoisotopic Molecular Weight625.155730636
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
  • Anthocyanin
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Flavonoid o-glycoside
  • Methoxyflavonoid skeleton
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • O-glycosyl compound
  • Glycosyl compound
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Methoxybenzene
  • Phenol ether
  • 1,2-diphenol
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • 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 CompositionC 59.52%; H 4.67%; O 35.81%CCD
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 ID10286568
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21674154
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID72
DrugBank IDNot Available
HMDB IDHMDB29240
CRC / DFC (Dictionary of Food Compounds) IDOJL40-V:NJO97-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00011188
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. de Villiers A, Vanhoenacker G, Majek P, Sandra P: Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. J Chromatogr A. 2004 Oct 29;1054(1-2):195-204. Pubmed [Structure]
Content Reference[3] Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
[2] 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.