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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:10:45 UTC
Update Date2022-03-07 02:55:33 UTC
HMDB IDHMDB0037920
Secondary Accession Numbers
  • HMDB37920
Metabolite Identification
Common 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. 3'-(gamma,gamma-Dimethylallyl)genistein is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3'-(gamma,gamma-Dimethylallyl)genistein.
Structure
Data?1563863109
Synonyms
ValueSource
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
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Name5,7-dihydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
Traditional Nameisowighteone
CAS Registry Number68436-47-5
SMILES
CC(C)=CCC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point171 - 172 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+177.45130932474
DeepCCS[M-H]-175.09330932474
DeepCCS[M-2H]-209.11330932474
DeepCCS[M+Na]+184.93230932474
AllCCS[M+H]+181.332859911
AllCCS[M+H-H2O]+178.032859911
AllCCS[M+NH4]+184.432859911
AllCCS[M+Na]+185.332859911
AllCCS[M-H]-180.032859911
AllCCS[M+Na-2H]-179.332859911
AllCCS[M+HCOO]-178.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-(gamma,gamma-Dimethylallyl)genisteinCC(C)=CCC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O4797.5Standard polar33892256
3'-(gamma,gamma-Dimethylallyl)genisteinCC(C)=CCC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O3046.7Standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genisteinCC(C)=CCC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O3346.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-(gamma,gamma-Dimethylallyl)genistein,1TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O[Si](C)(C)C3405.5Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,1TMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=CC=C1O3482.8Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,1TMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O3441.0Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)=CC=C1O[Si](C)(C)C3268.6Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O[Si](C)(C)C3248.2Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O3323.8Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,3TMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O[Si](C)(C)C3220.1Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,1TBDMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O[Si](C)(C)C(C)(C)C3673.8Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,1TBDMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=CC=C1O3739.2Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,1TBDMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O3700.3Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TBDMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)=CC=C1O[Si](C)(C)C(C)(C)C3793.6Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TBDMS,isomer #2CC(C)=CCC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O[Si](C)(C)C(C)(C)C3770.5Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,2TBDMS,isomer #3CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O3821.2Semi standard non polar33892256
3'-(gamma,gamma-Dimethylallyl)genistein,3TBDMS,isomer #1CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O[Si](C)(C)C(C)(C)C3944.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein EI-B (Non-derivatized)splash10-0uel-9653000000-9e7c1c95ff1fcbcaec3b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein EI-B (Non-derivatized)splash10-0uel-9653000000-9e7c1c95ff1fcbcaec3b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abd-3049000000-40d479e643002504baee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein GC-MS (3 TMS) - 70eV, Positivesplash10-000l-2100590000-1adf0e4e0fc469ba29102017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 10V, Positive-QTOFsplash10-000i-0129000000-178123992a900c26cdf82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 20V, Positive-QTOFsplash10-00sr-4398000000-4c1e397305e1106c54262016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 40V, Positive-QTOFsplash10-0gc0-7930000000-a349909f63a88331d0702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 10V, Negative-QTOFsplash10-000i-0009000000-4129bd05d056f4001c192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 20V, Negative-QTOFsplash10-000i-0419000000-362ad613cefa30d421df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 40V, Negative-QTOFsplash10-0a73-2942000000-db007a38da29152e57102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 10V, Positive-QTOFsplash10-0019-0059000000-fb3918e8ff9e09ef6e082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 20V, Positive-QTOFsplash10-001r-0093000000-60cdd9b6a0aa06aa5ac12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 40V, Positive-QTOFsplash10-0540-2291000000-4bc6fc05971ef35b2ecb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 10V, Negative-QTOFsplash10-000i-0009000000-fba49930c01349472a4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 20V, Negative-QTOFsplash10-000i-0019000000-24bd7484b308b09754292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-(gamma,gamma-Dimethylallyl)genistein 40V, Negative-QTOFsplash10-0f96-1491000000-b51f98112042a43570a62021-09-24Wishart LabView Spectrum
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 IDFDB017077
KNApSAcK IDC00009831
Chemspider ID4592155
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5494866
PDB IDNot Available
ChEBI ID69749
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .