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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:06 UTC
Update Date2021-09-14 15:16:00 UTC
HMDB IDHMDB0029239
Secondary Accession Numbers
  • HMDB29239
Metabolite Identification
Common Namep-Coumaroyl vitisin A
Descriptionp-Coumaroyl vitisin A belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. p-Coumaroyl vitisin A is an extremely weak basic (essentially neutral) compound (based on its pKa). A polyphenol compound found in foods of plant origin (PhenolExplorer).
Structure
Data?1582753391
SynonymsNot Available
Chemical FormulaC35H31O16
Average Molecular Weight707.616
Monoisotopic Molecular Weight707.160661338
IUPAC Name{3-[7-(dihydroxymethylidene)-11-hydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),3,5,9(13),10-pentaen-3-yl]-5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene}(methyl)oxidanium
Traditional Name{3-[7-(dihydroxymethylidene)-11-hydroxy-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),3,5,9(13),10-pentaen-3-yl]-5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene}(methyl)oxidanium
CAS Registry NumberNot Available
SMILES
[H][C@]1(COC(=O)C=CC2=CC=C(O)C=C2)OC([H])(OC2=C(OC3=CC(O)=CC4=C3C2=CC(O4)=C(O)O)C2=CC(=[O+]C)C(=O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI Identifier
InChI=1S/C35H30O16/c1-45-22-9-16(10-23(46-2)28(22)39)32-33(19-13-24(34(43)44)48-20-11-18(37)12-21(49-32)27(19)20)51-35-31(42)30(41)29(40)25(50-35)14-47-26(38)8-5-15-3-6-17(36)7-4-15/h3-13,25,29-31,35,40-42H,14H2,1-2H3,(H3-,36,37,38,43,44)/p+1/t25-,29-,30+,31-,35?/m1/s1
InChI KeyPKWYUQNQUIRDOJ-CJKUAQFFSA-O
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP10(3.14) g/LALOGPS
logP10(3.07) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area265.27 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity200.49 m³·mol⁻¹ChemAxon
Polarizability67.61 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000048
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]