Record Information
Version1.0
Creation date2010-04-08 22:04:25 UTC
Update date2020-02-24 19:10:06 UTC
Primary IDFDB000052
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePinotin A
DescriptionPinotin A belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Pinotin A is found, on average, in the highest concentration within grape wine. Pinotin A has also been detected, but not quantified in, common grapes (Vitis vinifera). This could make pinotin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pinotin A.
CAS Number663910-41-6
Structure
Thumb
Synonyms
SynonymSource
Malvidin 3-glucoside-4-vinylcatecholHMDB
Malvidin 3-O-glucoside caffeic acidHMDB
Malvidin 3-O-glucoside caffeic adductHMDB
Pinotin aMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.63ALOGPS
logP0.99ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area221.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity164.73 m³·mol⁻¹ChemAxon
Polarizability61.97 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]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 KeyRFTHDRVOYDHSOC-BGXVWEPQSA-O
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=C3C=C(OC4=CC(O)=CC([O+]=C2C2=CC(OC)=C(O)C(OC)=C2)=C34)C2=CC=C(O)C(O)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight625.5536
Monoisotopic Molecular Weight625.155730636
Classification
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • O-benzoquinone
  • Quinone
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPinotin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9300053000-5e28699fe21ecbdfa33aSpectrum
Predicted GC-MSPinotin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9720038000-c4217e375f0a28e80f9dSpectrum
Predicted GC-MSPinotin A, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPinotin A, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100009000-c439f81d9d5ff7e824e0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1300009000-831ac503eb2b8a47f164Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-9820311000-4b9b31d8a10e27b17220Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2300009000-881a35e5d2de25cabeaaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-6700009000-7eaec23bc91abe011816Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9200100000-9aeffcae19eb24937d0cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0000913000-45e49d0f093462a3e997Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000921000-fdaaeb41a1b0873599d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-6200952000-18b11f9320c10fda42beSpectrum
NMRNot 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
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. 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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.