Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2019-11-26 03:06:24 UTC
Primary IDFDB012215
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyclokievitone
DescriptionCyclokievitone 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, cyclokievitone is considered to be a flavonoid lipid molecule. Cyclokievitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cyclokievitone has been detected, but not quantified in, several different foods, such as green beans, lima beans, yellow wax beans, scarlet beans, and gram beans. This could make cyclokievitone a potential biomarker for the consumption of these foods.
CAS Number74175-82-9
Structure
Thumb
Synonyms
SynonymSource
1'',2''-DehydrocyclokievitoneHMDB
3-(2,4-Dihydroxyphenyl)-2,3-dihydro-5-hydroxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ciHMDB
3-(2,4-Dihydroxyphenyl)-2,3-dihydro-5-hydroxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.5ALOGPS
logP3.63ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.07 m³·mol⁻¹ChemAxon
Polarizability36.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O6
IUPAC name3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one
InChI IdentifierInChI=1S/C20H18O6/c1-20(2)6-5-12-16(26-20)8-15(23)17-18(24)13(9-25-19(12)17)11-4-3-10(21)7-14(11)22/h3-8,13,21-23H,9H2,1-2H3
InChI KeyAWLFGFDTGPLHKG-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2=CC(O)=C3C(=O)C(COC3=C2C=C1)C1=CC=C(O)C=C1O
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
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
  • Pyranoisoflavonoid
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 67.79%; H 5.12%; O 27.09%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 Data355 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0918000000-8bb552f798878973f2d4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0pi1-2290450000-7967e00c2405a2f38a88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0139000000-2959f9c5d663f64ce16eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cki-1779000000-a9888803e31401760c58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-4930000000-da1c93e03cd7567f2fadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-da6759113e9aedaf7428JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0359000000-306ce9e150dce00e2e6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3920000000-68b3f9eab5cc0965d46dJSpectraViewer
ChemSpider ID138019
ChEMBL IDNot Available
KEGG Compound IDC10207
Pubchem Compound ID156777
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33983
CRC / DFC (Dictionary of Food Compounds) IDHFF37-U:HFF37-U
EAFUS IDNot Available
Dr. Duke ID1",2"-DEHYDROCYCLOKIEVITONE|CYCLOKIEVITONE
BIGG IDNot Available
KNApSAcK IDC00009558
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
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
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
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.