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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:23:55 UTC
Update Date2022-03-07 02:55:38 UTC
HMDB IDHMDB0038114
Secondary Accession Numbers
  • HMDB38114
Metabolite Identification
Common Name4'-O-Methylkievitone
Description4'-O-Methylkievitone 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, 4'-O-methylkievitone is considered to be a flavonoid. 4'-O-Methylkievitone has been detected, but not quantified in, pulses. This could make 4'-O-methylkievitone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4'-O-Methylkievitone.
Structure
Data?1563863142
Synonyms
ValueSource
2',5,7-Trihydroxy-4'-methoxy-8-prenylisoflavanoneHMDB
Chemical FormulaC21H22O6
Average Molecular Weight370.3958
Monoisotopic Molecular Weight370.141638436
IUPAC Name5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name4'-O-methylkievitone
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C(C=C1)C1COC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C21H22O6/c1-11(2)4-6-14-17(23)9-18(24)19-20(25)15(10-27-21(14)19)13-7-5-12(26-3)8-16(13)22/h4-5,7-9,15,22-24H,6,10H2,1-3H3
InChI KeyUWWHTKLNJDNLDI-UHFFFAOYSA-N
Chemical Taxonomy
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
  • 4p-methoxyisoflavonoid
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.11ALOGPS
logP4.3ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.71ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.38 m³·mol⁻¹ChemAxon
Polarizability38.7 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
DarkChem[M+H]+186.02331661259
DarkChem[M-H]-188.69431661259
DeepCCS[M+H]+187.35830932474
DeepCCS[M-H]-185.030932474
DeepCCS[M-2H]-219.20830932474
DeepCCS[M+Na]+194.92730932474
AllCCS[M+H]+190.132859911
AllCCS[M+H-H2O]+187.132859911
AllCCS[M+NH4]+192.932859911
AllCCS[M+Na]+193.732859911
AllCCS[M-H]-190.732859911
AllCCS[M+Na-2H]-190.532859911
AllCCS[M+HCOO]-190.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4'-O-MethylkievitoneCOC1=CC(O)=C(C=C1)C1COC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O4491.9Standard polar33892256
4'-O-MethylkievitoneCOC1=CC(O)=C(C=C1)C1COC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O3256.8Standard non polar33892256
4'-O-MethylkievitoneCOC1=CC(O)=C(C=C1)C1COC2=C(CC=C(C)C)C(O)=CC(O)=C2C1=O3361.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4'-O-Methylkievitone,1TMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C13157.0Semi standard non polar33892256
4'-O-Methylkievitone,1TMS,isomer #2COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O)=C13138.2Semi standard non polar33892256
4'-O-Methylkievitone,1TMS,isomer #3COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C13185.4Semi standard non polar33892256
4'-O-Methylkievitone,2TMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C13062.2Semi standard non polar33892256
4'-O-Methylkievitone,2TMS,isomer #2COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C13085.0Semi standard non polar33892256
4'-O-Methylkievitone,2TMS,isomer #3COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C13076.8Semi standard non polar33892256
4'-O-Methylkievitone,3TMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C13038.0Semi standard non polar33892256
4'-O-Methylkievitone,1TBDMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13393.6Semi standard non polar33892256
4'-O-Methylkievitone,1TBDMS,isomer #2COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O)=C13375.5Semi standard non polar33892256
4'-O-Methylkievitone,1TBDMS,isomer #3COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13438.1Semi standard non polar33892256
4'-O-Methylkievitone,2TBDMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13525.7Semi standard non polar33892256
4'-O-Methylkievitone,2TBDMS,isomer #2COC1=CC=C(C2COC3=C(CC=C(C)C)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13551.4Semi standard non polar33892256
4'-O-Methylkievitone,2TBDMS,isomer #3COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13530.4Semi standard non polar33892256
4'-O-Methylkievitone,3TBDMS,isomer #1COC1=CC=C(C2COC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13693.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylkievitone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-2609000000-9e83b9f2d49e66b897072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylkievitone GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1320090000-af8f226b73c37ba9953c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylkievitone 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 - 4'-O-Methylkievitone 10V, Positive-QTOFsplash10-00di-0129000000-7681ffdf8e3ade6a57612016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 20V, Positive-QTOFsplash10-0gi9-2659000000-6f2e0bc20876bdf859242016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 40V, Positive-QTOFsplash10-0gb9-3921000000-7296a533a3f0a21bf4762016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 10V, Negative-QTOFsplash10-014i-0109000000-9d340e8f35d710bb46562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 20V, Negative-QTOFsplash10-014l-1729000000-d311e0d7fd0be5dcd0402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 40V, Negative-QTOFsplash10-00dl-7911000000-48674bc9ef8bbdd417802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 10V, Negative-QTOFsplash10-014i-0009000000-123d5a2cf35418de157f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 20V, Negative-QTOFsplash10-014i-0119000000-aeda74e227e036fb68be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 40V, Negative-QTOFsplash10-0g29-1396000000-14028751fbaafc61dd6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 10V, Positive-QTOFsplash10-00di-0219000000-1a79f54609c7ee8725e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 20V, Positive-QTOFsplash10-00kf-0926000000-3a929f03685cc1bff6352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylkievitone 40V, Positive-QTOFsplash10-0wmr-0920000000-5fdfa8443336938528f82021-09-22Wishart 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 IDFDB017339
KNApSAcK IDC00009959
Chemspider ID24842922
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257389
PDB IDNot Available
ChEBI IDNot Available
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.. .