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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:14:50 UTC
Update Date2022-03-07 02:55:59 UTC
HMDB IDHMDB0038899
Secondary Accession Numbers
  • HMDB38899
Metabolite Identification
Common Name2',4',5,7-Tetrahydroxy-8-prenylisoflavone
Description2',4',5,7-Tetrahydroxy-8-prenylisoflavone 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. 2',4',5,7-Tetrahydroxy-8-prenylisoflavone has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), pulses, lima beans (Phaseolus lunatus), mung beans (Vigna radiata), and yellow wax beans (Phaseolus vulgaris). This could make 2',4',5,7-tetrahydroxy-8-prenylisoflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2',4',5,7-Tetrahydroxy-8-prenylisoflavone.
Structure
Data?1563863277
Synonyms
ValueSource
2,3-DehydrokievitoneHMDB
5,7,2',4'-Tetrahydroxy-8-prenylisoflavoneHMDB
Chemical FormulaC20H18O6
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
IUPAC Name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Name2,3-dehydrokievitone
CAS Registry Number74161-25-4
SMILES
CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+184.75730932474
DeepCCS[M-H]-182.39930932474
DeepCCS[M-2H]-216.65130932474
DeepCCS[M+Na]+191.8830932474
AllCCS[M+H]+184.632859911
AllCCS[M+H-H2O]+181.432859911
AllCCS[M+NH4]+187.632859911
AllCCS[M+Na]+188.432859911
AllCCS[M-H]-183.232859911
AllCCS[M+Na-2H]-182.732859911
AllCCS[M+HCOO]-182.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2',4',5,7-Tetrahydroxy-8-prenylisoflavoneCC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C15023.8Standard polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavoneCC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C13160.3Standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavoneCC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C13425.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TMS,isomer #1CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3378.9Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3370.5Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3354.4Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TMS,isomer #4CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3372.5Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3262.2Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3253.9Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3255.5Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3235.0Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #5CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3249.4Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TMS,isomer #6CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3257.6Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C2=O3177.3Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C2=O3171.4Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3176.4Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3170.2Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,4TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C2=O3148.1Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3680.5Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3672.3Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3644.1Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,1TBDMS,isomer #4CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3653.6Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O)C2=O3793.1Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3799.1Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3770.7Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3778.2Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #5CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3754.6Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,2TBDMS,isomer #6CC(C)=CCC1=C(O)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O3770.9Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C2=O3880.1Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C2=O3837.5Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O3876.0Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,3TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O3859.9Semi standard non polar33892256
2',4',5,7-Tetrahydroxy-8-prenylisoflavone,4TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C2=O4004.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-2029000000-78a62be5f9533fc4668a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1000039000-c1dfcf161be27153f3812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 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 - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 10V, Positive-QTOFsplash10-0a4i-0019000000-27668c14920ba765e3bc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 20V, Positive-QTOFsplash10-05mk-3159000000-454b754ad4c9036748532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 40V, Positive-QTOFsplash10-014i-7293000000-9a00f5669a29a5fc07e22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 10V, Negative-QTOFsplash10-0udi-0009000000-c7c5c2e3f41a0258f63e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 20V, Negative-QTOFsplash10-0udi-0339000000-7c56cc7591c0e37abac32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 40V, Negative-QTOFsplash10-0a4i-5911000000-931b17d012cfa1139eed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 10V, Negative-QTOFsplash10-0udi-0009000000-b3503695056246b53ddc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 20V, Negative-QTOFsplash10-0udi-0019000000-37b553eed305d5793f422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 40V, Negative-QTOFsplash10-00lr-0592000000-9b78159c86fe1b5a649d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 10V, Positive-QTOFsplash10-0a4j-0069000000-e51562cdfec738228d482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 20V, Positive-QTOFsplash10-0002-0090000000-beec669836f276570b9f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2',4',5,7-Tetrahydroxy-8-prenylisoflavone 40V, Positive-QTOFsplash10-00gj-0191000000-7e50690e2c68e43855902021-09-22Wishart 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 IDFDB018363
KNApSAcK IDC00009502
Chemspider ID4677038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5746354
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1872531
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.. .