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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:27 UTC
Update Date2022-03-07 02:52:28 UTC
HMDB IDHMDB0030207
Secondary Accession Numbers
  • HMDB30207
Metabolite Identification
Common NameKoenigine
DescriptionKoenigine 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. Based on a literature review a small amount of articles have been published on Koenigine.
Structure
Data?1563861953
Synonyms
ValueSource
3,11-Dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazol-9-ol, 9ciHMDB
KenigineHMDB
Chemical FormulaC19H19NO3
Average Molecular Weight309.3591
Monoisotopic Molecular Weight309.136493479
IUPAC Name13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol
Traditional Name13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol
CAS Registry Number28513-33-9
SMILES
COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1
InChI Identifier
InChI=1S/C19H19NO3/c1-10-7-13-12-8-16(22-4)15(21)9-14(12)20-17(13)11-5-6-19(2,3)23-18(10)11/h5-9,20-21H,1-4H3
InChI KeyCZZZOTXCAIDYOZ-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
  • Hydroxyindole
  • 1-benzopyran
  • Indole
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen 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 Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP4.37ALOGPS
logP4.04ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.48 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.35 m³·mol⁻¹ChemAxon
Polarizability35 ųChemAxon
Number of Rings4ChemAxon
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]+173.13631661259
DarkChem[M-H]-175.93231661259
DeepCCS[M+H]+182.97630932474
DeepCCS[M-H]-180.61830932474
DeepCCS[M-2H]-214.7230932474
DeepCCS[M+Na]+189.94930932474
AllCCS[M+H]+173.432859911
AllCCS[M+H-H2O]+169.932859911
AllCCS[M+NH4]+176.732859911
AllCCS[M+Na]+177.632859911
AllCCS[M-H]-179.632859911
AllCCS[M+Na-2H]-178.832859911
AllCCS[M+HCOO]-178.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KoenigineCOC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C13994.8Standard polar33892256
KoenigineCOC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C12919.1Standard non polar33892256
KoenigineCOC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C12998.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Koenigine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C1=C3C=CC(C)(C)OC3=C(C)C=C123185.6Semi standard non polar33892256
Koenigine,1TMS,isomer #2COC1=CC2=C(C=C1O)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C213118.2Semi standard non polar33892256
Koenigine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C213090.3Semi standard non polar33892256
Koenigine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C212712.6Standard non polar33892256
Koenigine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C1=C3C=CC(C)(C)OC3=C(C)C=C123340.5Semi standard non polar33892256
Koenigine,1TBDMS,isomer #2COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C213260.0Semi standard non polar33892256
Koenigine,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C213395.6Semi standard non polar33892256
Koenigine,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C213143.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Koenigine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0291000000-9181726a39da865b5be82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Koenigine GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-1119000000-511ee32d5b4b851c8fd02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Koenigine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Koenigine 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 - Koenigine 10V, Positive-QTOFsplash10-03di-0029000000-6ace861290084dedf6a92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 20V, Positive-QTOFsplash10-03di-1096000000-ef8cb7772fa70c5185122016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 40V, Positive-QTOFsplash10-0udi-1090000000-9746852717055824945b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 10V, Negative-QTOFsplash10-0a4i-0019000000-983934a0570a6bee38592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 20V, Negative-QTOFsplash10-0a4i-1089000000-8bc8c641f0d0165e7adb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 40V, Negative-QTOFsplash10-006x-0190000000-9a6ea3a6cc5719d23a122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 10V, Negative-QTOFsplash10-0a4i-0009000000-6f2b8145258635fcc7b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 20V, Negative-QTOFsplash10-0a4i-0039000000-2d6aa6a60639f4bb1a7f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 40V, Negative-QTOFsplash10-0ik9-0090000000-a652b4085a953b6e44612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 10V, Positive-QTOFsplash10-03di-0009000000-9b0e111066a4aee0da172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 20V, Positive-QTOFsplash10-03di-0039000000-ccfc460b7b6116a61bf12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Koenigine 40V, Positive-QTOFsplash10-0udl-1190000000-c6bc26802bb54998886f2021-09-23Wishart 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 IDFDB002025
KNApSAcK IDC00051146
Chemspider ID4477289
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318825
PDB IDNot Available
ChEBI ID168437
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.. .