Record Information
Version1.0
Creation date2010-04-08 22:11:43 UTC
Update date2019-11-26 03:11:18 UTC
Primary IDFDB015221
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVitisin A
DescriptionVitisin A 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''. Vitisin A is found, on average, in the highest concentration within grape wine. Vitisin A has also been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes (Vitis vinifera), and red wine. This could make vitisin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vitisin A.
CAS Number184362-09-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP2.05ALOGPS
logP0.39ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area217.97 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.39 m³·mol⁻¹ChemAxon
Polarizability53.88 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H25O14
IUPAC name7-carboxy-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/C26H24O14/c1-35-14-3-9(4-15(36-2)19(14)29)23-24(40-26-22(32)21(31)20(30)17(8-27)39-26)11-7-16(25(33)34)37-12-5-10(28)6-13(38-23)18(11)12/h3-7,17,20-22,26-27,30-32H,8H2,1-2H3,(H2-,28,29,33,34)/p+1/t17-,20-,21+,22-,26+/m1/s1
InChI KeyQVULQDHVHOUFCX-AQFMKAHKSA-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)C(O)=O)=CC(O)=C2
Average Molecular Weight561.4683
Monoisotopic Molecular Weight561.124430508
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
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Anthocyanidin-3-o-glycoside
  • Anthocyanin
  • Flavonoid o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • 1-benzopyran
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVitisin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abc-9300350000-9a87afcd8c7a911597adSpectrum
Predicted GC-MSVitisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0avi-9200037000-377e9278f6800932334eSpectrum
Predicted GC-MSVitisin A, "Vitisin A,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitisin A, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100090000-db62db54a92394f4b01d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-1200090000-9b8b3dbfe9cb7d9459852016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-7902030000-a13b6d39987edfce2a852016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300090000-41f4fa71d6e8862274fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5700090000-4656c50bef5697b84b242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9500000000-37349fe117dc8607bc162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w2d-0008590000-1bd578101ffdda52fb5f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0009320000-abd37ec220c242d2fd222021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-5309210000-f9feb2c8ca6061dadd652021-09-22View 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 ID63
DrugBank IDNot Available
HMDB IDHMDB36348
CRC / DFC (Dictionary of Food Compounds) IDBOX04-R:JYT18-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00011186
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
Processing...
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. Fulcrand H, Benabdeljalil C, Rigaud J, Cheynier V, Moutounet M: A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry. 1998 Apr;47(7):1401-7. 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.