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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:28 UTC
Update Date2022-03-07 02:52:28 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, koenimbine has been detected, but not quantified in, herbs and spices. This could make koenimbine a potential biomarker for the consumption of these foods.
Structure
Data?1563861954
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
Description 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.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 195 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.67931661259
DarkChem[M-H]-174.33531661259
DeepCCS[M-2H]-213.75730932474
DeepCCS[M+Na]+189.27730932474
AllCCS[M+H]+169.732859911
AllCCS[M+H-H2O]+166.032859911
AllCCS[M+NH4]+173.032859911
AllCCS[M+Na]+174.032859911
AllCCS[M-H]-176.932859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-175.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KoenimbineCOC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C13673.9Standard polar33892256
KoenimbineCOC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C12789.4Standard non polar33892256
KoenimbineCOC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C12824.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Koenimbine,1TMS,isomer #1COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C2977.3Semi standard non polar33892256
Koenimbine,1TMS,isomer #1COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C2481.3Standard non polar33892256
Koenimbine,1TBDMS,isomer #1COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C3094.3Semi standard non polar33892256
Koenimbine,1TBDMS,isomer #1COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C2694.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Koenimbine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0290000000-dfd9f19a83c8266db33e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Koenimbine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Koenimbine 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 - Koenimbine 10V, Positive-QTOFsplash10-0006-0090000000-4270e2965a99d1c5e3da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 20V, Positive-QTOFsplash10-0006-0090000000-20b4f72c40f10fa290cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 40V, Positive-QTOFsplash10-05nr-2190000000-8bcf2a6a33863e5eb3202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 10V, Negative-QTOFsplash10-0006-0090000000-91c46a3905540c41e5e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 20V, Negative-QTOFsplash10-0006-0090000000-c3c87733ef889c4e7fa02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 40V, Negative-QTOFsplash10-0pk9-0290000000-16d0f35388ab0bf60a2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 10V, Positive-QTOFsplash10-0006-0090000000-c0ae6c1ee6eacc17ae1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 20V, Positive-QTOFsplash10-0006-0090000000-1a0b237e4e93652f5fb92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 40V, Positive-QTOFsplash10-002r-1190000000-db3b177d0f4f971c7b9b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 10V, Negative-QTOFsplash10-0006-0090000000-80f6742b4f6b5e8352cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 20V, Negative-QTOFsplash10-002f-0090000000-907aa049544222e8b63b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenimbine 40V, Negative-QTOFsplash10-001i-0090000000-2550143bbf44789f8f062021-09-24Wishart 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 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
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.. .