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Showing Compound 3'-(gamma,gamma-Dimethylallyl)genistein (FDB017077)

Record Information
Version1.0
Creation date2010-04-08 22:12:49 UTC
Update date2019-11-26 03:14:10 UTC
Primary IDFDB017077
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3'-(gamma,gamma-Dimethylallyl)genistein
Description3'-(gamma,gamma-Dimethylallyl)genistein, also known as 3'-isoprenylgenistein or 3'-prenyl-5,7,4'-trihydroxyisoflavone, 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, 3'-(gamma,gamma-dimethylallyl)genistein is considered to be a flavonoid. 3'-(gamma,gamma-Dimethylallyl)genistein has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make 3'-(gamma,gamma-dimethylallyl)genistein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3'-(gamma,gamma-Dimethylallyl)genistein.
CAS Number68436-47-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3'-IsoprenylgenisteinChEBI
3'-Prenyl-5,7,4'-trihydroxyisoflavoneChEBI
5,7,4'-Trihydroxy-3'-prenylisoflavoneChEBI
3'-(g,g-Dimethylallyl)genisteinGenerator
3'-(Γ,γ-dimethylallyl)genisteinGenerator
3'-PrenylgenisteinHMDB
5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9ciHMDB
IsowighteoneHMDB
3'-(gamma,gamma-Dimethylallyl)genisteinChEBI
3'-(γ,γ-dimethylallyl)genisteinGenerator
5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP4.04ALOGPS
logP4.81ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.93 m³·mol⁻¹ChemAxon
Polarizability36.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O5
IUPAC name5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H18O5/c1-11(2)3-4-13-7-12(5-6-16(13)22)15-10-25-18-9-14(21)8-17(23)19(18)20(15)24/h3,5-10,21-23H,4H2,1-2H3
InChI KeySWDSVBNAMCDHTF-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
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
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • 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 71.00%; H 5.36%; O 23.64%DFC
Melting PointMp 171-172°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data330 (sh) () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3'-(gamma,gamma-Dimethylallyl)genistein, non-derivatized, GC-MS Spectrumsplash10-0uel-9653000000-9e7c1c95ff1fcbcaec3bSpectrum
GC-MS3'-(gamma,gamma-Dimethylallyl)genistein, non-derivatized, GC-MS Spectrumsplash10-0uel-9653000000-9e7c1c95ff1fcbcaec3bSpectrum
Predicted GC-MS3'-(gamma,gamma-Dimethylallyl)genistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abd-3049000000-40d479e643002504baeeSpectrum
Predicted GC-MS3'-(gamma,gamma-Dimethylallyl)genistein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-2100590000-1adf0e4e0fc469ba2910Spectrum
Predicted GC-MS3'-(gamma,gamma-Dimethylallyl)genistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0129000000-178123992a900c26cdf82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00sr-4398000000-4c1e397305e1106c54262016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-7930000000-a349909f63a88331d0702016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-4129bd05d056f4001c192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0419000000-362ad613cefa30d421df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-2942000000-db007a38da29152e57102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0059000000-fb3918e8ff9e09ef6e082021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0093000000-60cdd9b6a0aa06aa5ac12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-2291000000-4bc6fc05971ef35b2ecb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-fba49930c01349472a4d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000000-24bd7484b308b09754292021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-1491000000-b51f98112042a43570a62021-09-24View Spectrum
NMRNot Available
ChemSpider ID4592155
ChEMBL IDCHEMBL464460
KEGG Compound IDNot Available
Pubchem Compound ID5494866
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37920
CRC / DFC (Dictionary of Food Compounds) IDKWC09-U:KWC09-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009831
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.