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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:15 UTC
Update Date2022-03-07 02:53:26 UTC
HMDB IDHMDB0032696
Secondary Accession Numbers
  • HMDB32696
Metabolite Identification
Common NameCajanin
DescriptionCajanin belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, cajanin is considered to be a flavonoid. Cajanin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, pigeon peas (Cajanus cajan), pulses, and robusta coffees (Coffea canephora). This could make cajanin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cajanin.
Structure
Data?1563862294
Synonyms
ValueSource
2',4',5-Trihydroxy-7-methoxyisoflavoneHMDB
CajininHMDB
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one
Traditional Namecajanin
CAS Registry Number32884-36-9
SMILES
COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C16H12O6/c1-21-9-5-13(19)15-14(6-9)22-7-11(16(15)20)10-3-2-8(17)4-12(10)18/h2-7,17-19H,1H3
InChI KeyALFNTRJPGFNJQV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent7-O-methylisoflavones
Alternative Parents
Substituents
  • 7-o-methylisoflavone
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Point208 - 210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility147.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP3.01ALOGPS
logP2.92ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.22ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.15 m³·mol⁻¹ChemAxon
Polarizability29.53 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]+174.08230932474
DeepCCS[M-H]-171.72430932474
DeepCCS[M-2H]-205.77430932474
DeepCCS[M+Na]+181.00130932474
AllCCS[M+H]+168.632859911
AllCCS[M+H-H2O]+164.932859911
AllCCS[M+NH4]+171.932859911
AllCCS[M+Na]+172.932859911
AllCCS[M-H]-169.532859911
AllCCS[M+Na-2H]-168.932859911
AllCCS[M+HCOO]-168.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CajaninCOC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C14546.9Standard polar33892256
CajaninCOC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C12859.5Standard non polar33892256
CajaninCOC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C12980.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cajanin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13084.8Semi standard non polar33892256
Cajanin,1TMS,isomer #2COC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C13027.4Semi standard non polar33892256
Cajanin,1TMS,isomer #3COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O)=COC2=C13080.0Semi standard non polar33892256
Cajanin,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O)=COC2=C12955.6Semi standard non polar33892256
Cajanin,2TMS,isomer #2COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C12929.7Semi standard non polar33892256
Cajanin,2TMS,isomer #3COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)=COC2=C12962.3Semi standard non polar33892256
Cajanin,3TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)=COC2=C12891.1Semi standard non polar33892256
Cajanin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13358.0Semi standard non polar33892256
Cajanin,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13307.2Semi standard non polar33892256
Cajanin,1TBDMS,isomer #3COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)=COC2=C13342.2Semi standard non polar33892256
Cajanin,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)=COC2=C13484.7Semi standard non polar33892256
Cajanin,2TBDMS,isomer #2COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13440.6Semi standard non polar33892256
Cajanin,2TBDMS,isomer #3COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13467.2Semi standard non polar33892256
Cajanin,3TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13591.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cajanin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0591000000-2d725dedc079e3bf5cc42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cajanin GC-MS (3 TMS) - 70eV, Positivesplash10-0fkc-2170950000-8a37dcc2d7e2a3c24a672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cajanin 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 - Cajanin 10V, Positive-QTOFsplash10-0udi-0009000000-9de62c366ea45b58088f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 20V, Positive-QTOFsplash10-0udi-0019000000-faebb53f0f824f475c3f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 40V, Positive-QTOFsplash10-0uy0-3790000000-1a6c3965725a8acc19212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 10V, Negative-QTOFsplash10-0002-0090000000-f9e2a2f74f45fb1e1fe42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 20V, Negative-QTOFsplash10-0002-0090000000-85b3c09fa13b64ca415e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 40V, Negative-QTOFsplash10-0159-3690000000-fcc07e28e468be59704f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 10V, Negative-QTOFsplash10-0002-0090000000-fb4a565723d52a1e46242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 20V, Negative-QTOFsplash10-0002-0090000000-fb4a565723d52a1e46242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 40V, Negative-QTOFsplash10-00mo-0590000000-c12ad5716ba473535f982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 10V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 20V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cajanin 40V, Positive-QTOFsplash10-0a7i-0390000000-9e3fdcbbe9204f317f212021-09-24Wishart 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 IDFDB010653
KNApSAcK IDC00002512
Chemspider ID4445023
KEGG Compound IDC10203
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281706
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1830961
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Cajanin → 3,4,5-trihydroxy-6-[3-hydroxy-4-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)phenoxy]oxane-2-carboxylic aciddetails