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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:34:23 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033806
Secondary Accession Numbers
  • HMDB33806
Metabolite Identification
Common Name2'-O-Methylcajanone
Description2'-O-Methylcajanone belongs to the class of organic compounds known as 3'-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 3'-position. Thus, 2'-O-methylcajanone is considered to be a flavonoid. 2'-O-Methylcajanone has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make 2'-O-methylcajanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2'-O-Methylcajanone.
Structure
Data?1563862463
SynonymsNot Available
Chemical FormulaC26H28O6
Average Molecular Weight436.4969
Monoisotopic Molecular Weight436.188588628
IUPAC Name9-hydroxy-6-[4-hydroxy-2-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),9,11-tetraen-7-one
Traditional Name2'-O-methylcajanone
CAS Registry Number71765-79-2
SMILES
COC1=C(C=C(CC=C(C)C)C(O)=C1)C1COC2=C(C1=O)C(O)=C1C=CC(C)(C)OC1=C2
InChI Identifier
InChI=1S/C26H28O6/c1-14(2)6-7-15-10-17(20(30-5)11-19(15)27)18-13-31-22-12-21-16(8-9-26(3,4)32-21)24(28)23(22)25(18)29/h6,8-12,18,27-28H,7,13H2,1-5H3
InChI KeyREBVXJPVOISSEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent3'-prenylated isoflavanones
Alternative Parents
Substituents
  • 3'-prenylated isoflavanone
  • 2p-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Aryl ketone
  • Aryl alkyl ketone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Point85 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP4.18ALOGPS
logP5.5ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity124.8 m³·mol⁻¹ChemAxon
Polarizability47.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.52731661259
DarkChem[M-H]-206.1231661259
DeepCCS[M+H]+209.2930932474
DeepCCS[M-H]-206.93230932474
DeepCCS[M-2H]-239.82530932474
DeepCCS[M+Na]+215.38330932474
AllCCS[M+H]+208.732859911
AllCCS[M+H-H2O]+206.132859911
AllCCS[M+NH4]+211.132859911
AllCCS[M+Na]+211.832859911
AllCCS[M-H]-207.232859911
AllCCS[M+Na-2H]-207.732859911
AllCCS[M+HCOO]-208.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2'-O-MethylcajanoneCOC1=C(C=C(CC=C(C)C)C(O)=C1)C1COC2=C(C1=O)C(O)=C1C=CC(C)(C)OC1=C24774.9Standard polar33892256
2'-O-MethylcajanoneCOC1=C(C=C(CC=C(C)C)C(O)=C1)C1COC2=C(C1=O)C(O)=C1C=CC(C)(C)OC1=C23444.1Standard non polar33892256
2'-O-MethylcajanoneCOC1=C(C=C(CC=C(C)C)C(O)=C1)C1COC2=C(C1=O)C(O)=C1C=CC(C)(C)OC1=C23622.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-O-Methylcajanone,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O)=C2C1=O3430.4Semi standard non polar33892256
2'-O-Methylcajanone,1TMS,isomer #2COC1=CC(O)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C2C1=O3482.7Semi standard non polar33892256
2'-O-Methylcajanone,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C2C1=O3368.3Semi standard non polar33892256
2'-O-Methylcajanone,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O)=C2C1=O3678.7Semi standard non polar33892256
2'-O-Methylcajanone,1TBDMS,isomer #2COC1=CC(O)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3728.1Semi standard non polar33892256
2'-O-Methylcajanone,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C=C1C1COC2=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3826.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-O-Methylcajanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1432900000-a4ff119a8a013d041c312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-O-Methylcajanone GC-MS (2 TMS) - 70eV, Positivesplash10-014i-1030090000-64576a7ae7ad8c8dc13f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-O-Methylcajanone 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'-O-Methylcajanone 10V, Positive-QTOFsplash10-000i-1043900000-79972c6d583f9534bb9b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 20V, Positive-QTOFsplash10-014r-4489500000-d116813f10c9807dbe312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 40V, Positive-QTOFsplash10-014i-8971200000-51205c022b8097794f402016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 10V, Negative-QTOFsplash10-000i-0010900000-d1d16e1800d3ef40f5222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 20V, Negative-QTOFsplash10-000e-0491500000-419722fd68b0ef45cad82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 40V, Negative-QTOFsplash10-004i-0921000000-3484a233d6f572b3ed312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 10V, Negative-QTOFsplash10-000i-0010900000-9db46200d7d239ff72342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 20V, Negative-QTOFsplash10-001a-0041900000-178d73be51d80f8a98092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 40V, Negative-QTOFsplash10-004i-0339100000-a271826fdc2a42e95fbb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 10V, Positive-QTOFsplash10-000i-0004900000-f5ce18e075f80f6bcb552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 20V, Positive-QTOFsplash10-001a-0129600000-5791146de86f906aa35d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-O-Methylcajanone 40V, Positive-QTOFsplash10-0006-3945100000-4e0112e7e7af43e7a0de2021-09-25Wishart 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 IDFDB011969
KNApSAcK IDC00009563
Chemspider ID551063
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound634867
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.. .