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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:28 UTC
Update Date2018-03-12 22:01:34 UTC
HMDB IDHMDB0030210
Secondary Accession Numbers
  • HMDB30210
Metabolite Identification
Common NameKoenimbine
DescriptionKoenimbine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Koenimbine exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, koenimbine is primarily located in the membrane (predicted from logP). Outside of the human body, koenimbine can be found in herbs and spices. This makes koenimbine a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
3,11-dihydro-8-Methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ciHMDB
KenimbineHMDB
KoenimbinHMDB
Chemical FormulaC19H19NO2
Average Molecular Weight293.3597
Monoisotopic Molecular Weight293.141578857
IUPAC Name13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene
Traditional Name13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene
CAS Registry Number21087-98-9
SMILES
COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1
InChI Identifier
InChI=1S/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3
InChI KeyOSERHKINMDLESD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassCarbazoles
Direct ParentCarbazoles
Alternative Parents
Substituents
  • Carbazole
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Indole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 - 195 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00079 g/LALOGPS
logP5.33ALOGPS
logP4.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area34.25 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.37 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0290000000-dfd9f19a83c8266db33eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4270e2965a99d1c5e3daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-20b4f72c40f10fa290cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nr-2190000000-8bcf2a6a33863e5eb320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-91c46a3905540c41e5e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-c3c87733ef889c4e7fa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pk9-0290000000-16d0f35388ab0bf60a2bView in MoNA
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
FoodDB IDFDB002028
KNApSAcK IDNot Available
Chemspider ID87989
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97487
PDB IDNot Available
ChEBI 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.. .