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Showing Compound 2',4',5,7-Tetrahydroxy-8-prenylisoflavone (FDB018363)

Record Information
Version1.0
Creation date2010-04-08 22:13:40 UTC
Update date2019-11-26 03:16:04 UTC
Primary IDFDB018363
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2',4',5,7-Tetrahydroxy-8-prenylisoflavone
Description2',4',5,7-Tetrahydroxy-8-prenylisoflavone, also known as 2,3-dehydrokievitone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 2',4',5,7-tetrahydroxy-8-prenylisoflavone is considered to be a flavonoid lipid molecule. 2',4',5,7-Tetrahydroxy-8-prenylisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2',4',5,7-Tetrahydroxy-8-prenylisoflavone has been detected, but not quantified in, several different foods, such as lima beans, green beans, common beans, yellow wax beans, and mung beans. This could make 2',4',5,7-tetrahydroxy-8-prenylisoflavone a potential biomarker for the consumption of these foods.
CAS Number74161-25-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,3-DehydrokievitoneHMDB
5,7,2',4'-Tetrahydroxy-8-prenylisoflavoneHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.32ALOGPS
logP4.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)6.41ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.91 m³·mol⁻¹ChemAxon
Polarizability36.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O6
IUPAC name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H18O6/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/h3-4,6-9,21-24H,5H2,1-2H3
InChI KeyRWDSADRZXTYPMY-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C1
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
Classification
Description belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • 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 Data[base] lmax 281 () (MeOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-2029000000-78a62be5f9533fc4668aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1000039000-c1dfcf161be27153f381JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-27668c14920ba765e3bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-3159000000-454b754ad4c903674853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7293000000-9a00f5669a29a5fc07e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-c7c5c2e3f41a0258f63eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0339000000-7c56cc7591c0e37abac3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5911000000-931b17d012cfa1139eedJSpectraViewer
ChemSpider ID4677038
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5746354
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38899
CRC / DFC (Dictionary of Food Compounds) IDLJX88-Q:LJX88-Q
EAFUS IDNot Available
Dr. Duke ID2,3-DEHYDROKIEVITONE
BIGG IDNot Available
KNApSAcK IDC00009502
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.