Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:56 UTC
Primary IDFDB012516
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKievitone
DescriptionKievitone, also known as vignatin, belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. Thus, kievitone is considered to be a flavonoid lipid molecule. Kievitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Kievitone has been detected, but not quantified in, several different foods, such as cowpea, adzuki beans, scarlet beans, common beans, and mung beans. This could make kievitone a potential biomarker for the consumption of these foods.
CAS Number40105-60-0
Structure
Thumb
Synonyms
SynonymSource
3-(2,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
Phaseolus substance IIHMDB
VignatinHMDB
3-(2,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Kievitonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP2.99ALOGPS
logP4.15ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)7.66ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.9 m³·mol⁻¹ChemAxon
Polarizability36.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20O6
IUPAC name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C20H20O6/c1-10(2)3-5-13-16(23)8-17(24)18-19(25)14(9-26-20(13)18)12-6-4-11(21)7-15(12)22/h3-4,6-8,14,21-24H,5,9H2,1-2H3
InChI KeyMERHMOCEIBOOMA-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C2OCC(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C1
Average Molecular Weight356.3692
Monoisotopic Molecular Weight356.125988372
Classification
Description belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent8-prenylated isoflavanones
Alternative Parents
Substituents
  • 8-prenylated isoflavanone
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.41%; H 5.66%; O 26.94%DFC
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 Data340 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-3519000000-da2fbf88884ce450dacfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fir-2040049000-acf25239ce602f7d7b4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0129000000-d1b882cd2681756e738eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l70-3869000000-1063d83e3b9621bbf071JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3911000000-5c02aabd4e5e8e2882c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0109000000-f06e5345ef8f8de68374JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0947000000-ddbfd90b5c91692e7c6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3910000000-2166b37c455e5fb8d0afJSpectraViewer
ChemSpider ID106542
ChEMBL IDNot Available
KEGG Compound IDC01590
Pubchem Compound ID119269
Pubchem Substance IDNot Available
ChEBI ID16832
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34213
CRC / DFC (Dictionary of Food Compounds) IDHHQ84-X:HHQ84-X
EAFUS IDNot Available
Dr. Duke IDKIEVITONE
BIGG IDNot Available
KNApSAcK IDC00002541
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 / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.