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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:41:54 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033924
Secondary Accession Numbers
  • HMDB33924
Metabolite Identification
Common NameCajanol
DescriptionCajanol belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, cajanol is considered to be a flavonoid. Cajanol has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make cajanol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cajanol.
Structure
Data?1563862482
Synonyms
ValueSource
4',5-Dihydroxy-2',7-dimethoxyisoflavanoneHMDB
Chemical FormulaC17H16O6
Average Molecular Weight316.3053
Monoisotopic Molecular Weight316.094688244
IUPAC Name5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namecajanol
CAS Registry Number61020-70-0
SMILES
COC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C1
InChI Identifier
InChI=1S/C17H16O6/c1-21-10-6-13(19)16-15(7-10)23-8-12(17(16)20)11-4-3-9(18)5-14(11)22-2/h3-7,12,18-19H,8H2,1-2H3
InChI KeyRYYWWFXWFMYKJM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent7-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
  • 7-methoxyisoflavonoid-skeleton
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavanone
  • Isoflavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • 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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility62.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP2.78ALOGPS
logP2.72ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.62 m³·mol⁻¹ChemAxon
Polarizability31.68 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]+174.24931661259
DarkChem[M-H]-174.45831661259
DeepCCS[M+H]+178.82130932474
DeepCCS[M-H]-176.46330932474
DeepCCS[M-2H]-210.51630932474
DeepCCS[M+Na]+185.74330932474
AllCCS[M+H]+173.732859911
AllCCS[M+H-H2O]+170.332859911
AllCCS[M+NH4]+177.032859911
AllCCS[M+Na]+177.932859911
AllCCS[M-H]-176.332859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-175.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CajanolCOC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C14092.7Standard polar33892256
CajanolCOC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C12890.1Standard non polar33892256
CajanolCOC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C13005.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cajanol,1TMS,isomer #1COC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3OC)CO2)C(O[Si](C)(C)C)=C12894.3Semi standard non polar33892256
Cajanol,1TMS,isomer #2COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3OC)COC2=C12848.0Semi standard non polar33892256
Cajanol,2TMS,isomer #1COC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3OC)CO2)C(O[Si](C)(C)C)=C12791.4Semi standard non polar33892256
Cajanol,1TBDMS,isomer #1COC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3OC)CO2)C(O[Si](C)(C)C(C)(C)C)=C13146.0Semi standard non polar33892256
Cajanol,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)COC2=C13103.4Semi standard non polar33892256
Cajanol,2TBDMS,isomer #1COC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)CO2)C(O[Si](C)(C)C(C)(C)C)=C13290.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cajanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0962000000-1f286a9d768f17f227ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cajanol GC-MS (2 TMS) - 70eV, Positivesplash10-006t-5743900000-66dcacacf6409e3d921b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cajanol 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 - Cajanol 10V, Positive-QTOFsplash10-014i-0439000000-9178972eb0df1ac5bbd92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 20V, Positive-QTOFsplash10-014r-0943000000-a6bbc67ee5ad791006a62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 40V, Positive-QTOFsplash10-014r-1910000000-4d36e1a0c0db818e2b5a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 10V, Negative-QTOFsplash10-014i-0019000000-bc5ce896443d7ccab5492015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 20V, Negative-QTOFsplash10-014i-0897000000-c3f885ce66d3c32a99502015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 40V, Negative-QTOFsplash10-00xr-8970000000-c9ad7f726a2934c55a662015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 10V, Positive-QTOFsplash10-014i-0209000000-ee2b84d4fd0a849d586a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 20V, Positive-QTOFsplash10-014m-0902000000-cf023e624af01c6e89582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 40V, Positive-QTOFsplash10-014i-0920000000-ee180313b1e9aad8cb5e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 10V, Negative-QTOFsplash10-014i-0009000000-57e0edfe40e4094c309a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 20V, Negative-QTOFsplash10-016s-0896000000-33081233015da57b7a0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanol 40V, Negative-QTOFsplash10-014i-0390000000-d3f68146d89e03e730aa2021-09-22Wishart 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 IDFDB012124
KNApSAcK IDC00002513
Chemspider ID391028
KEGG Compound IDC10204
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442670
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Liu XL, Zhang XJ, Fu YJ, Zu YG, Wu N, Liang L, Efferth T: Cajanol inhibits the growth of Escherichia coli and Staphylococcus aureus by acting on membrane and DNA damage. Planta Med. 2011 Jan;77(2):158-63. doi: 10.1055/s-0030-1250146. Epub 2010 Aug 27. [PubMed:20803417 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .