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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:32 UTC
Update Date2021-09-14 15:02:27 UTC
HMDB IDHMDB0060549
Secondary Accession Numbers
  • HMDB60549
Metabolite Identification
Common NameNorketamine
DescriptionNorketamine is the main metabolite of Ketamine. Ketamine is a drug used in human and veterinary medicine, primarily for the induction and maintenance of general anesthesia, usually in combination with a sedative. When administered orally, it undergoes first-pass metabolism, where it is biotransformed in the liver by CYP3A4 (major), CYP2B6 (minor), and CYP2C9 (minor) isoenzymes into norketamine (through N-demethylation) and finally dehydronorketamine. (Wikipedia )
Structure
Data?1563866074
Synonyms
ValueSource
2-Amino-2-(O-chlorophenyl)cyclohexanoneHMDB
DHNKHMDB
DehydronorketamineHMDB
Norketamine, (+-)-isomerHMDB
N-DesmethylketamineMeSH
(+--)-NorketamineMeSH
N-DemethylketamineMeSH
Chemical FormulaC12H14ClNO
Average Molecular Weight223.699
Monoisotopic Molecular Weight223.076391782
IUPAC Name2-amino-2-(2-chlorophenyl)cyclohexan-1-one
Traditional Name2-amino-2-(2-chlorophenyl)cyclohexan-1-one
CAS Registry NumberNot Available
SMILES
NC1(CCCCC1=O)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C12H14ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-2,5-6H,3-4,7-8,14H2
InChI KeyBEQZHFIKTBVCAU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Ketone
  • Cyclic ketone
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.22ALOGPS
logP2.91ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)18.74ChemAxon
pKa (Strongest Basic)7.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.78 m³·mol⁻¹ChemAxon
Polarizability22.78 ųChemAxon
Number of Rings2ChemAxon
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]+148.15130932474
DeepCCS[M-H]-145.77730932474
DeepCCS[M-2H]-181.06330932474
DeepCCS[M+Na]+156.60230932474
AllCCS[M+H]+149.432859911
AllCCS[M+H-H2O]+145.432859911
AllCCS[M+NH4]+153.232859911
AllCCS[M+Na]+154.332859911
AllCCS[M-H]-151.632859911
AllCCS[M+Na-2H]-151.932859911
AllCCS[M+HCOO]-152.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorketamineNC1(CCCCC1=O)C1=CC=CC=C1Cl2413.5Standard polar33892256
NorketamineNC1(CCCCC1=O)C1=CC=CC=C1Cl1876.2Standard non polar33892256
NorketamineNC1(CCCCC1=O)C1=CC=CC=C1Cl1851.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norketamine,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl1937.1Semi standard non polar33892256
Norketamine,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl1851.8Standard non polar33892256
Norketamine,1TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl2736.9Standard polar33892256
Norketamine,1TMS,isomer #2C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O1924.5Semi standard non polar33892256
Norketamine,1TMS,isomer #2C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O1931.1Standard non polar33892256
Norketamine,1TMS,isomer #2C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O2462.7Standard polar33892256
Norketamine,2TMS,isomer #1C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C1975.1Semi standard non polar33892256
Norketamine,2TMS,isomer #1C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C2007.5Standard non polar33892256
Norketamine,2TMS,isomer #1C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C2415.6Standard polar33892256
Norketamine,2TMS,isomer #2C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C2023.5Semi standard non polar33892256
Norketamine,2TMS,isomer #2C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C2116.0Standard non polar33892256
Norketamine,2TMS,isomer #2C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C2465.4Standard polar33892256
Norketamine,3TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C2074.6Semi standard non polar33892256
Norketamine,3TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C2113.1Standard non polar33892256
Norketamine,3TMS,isomer #1C[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C2371.3Standard polar33892256
Norketamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl2158.9Semi standard non polar33892256
Norketamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl2022.5Standard non polar33892256
Norketamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(N)C1=CC=CC=C1Cl2900.6Standard polar33892256
Norketamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O2154.4Semi standard non polar33892256
Norketamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O2185.5Standard non polar33892256
Norketamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCCC1=O2584.5Standard polar33892256
Norketamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2415.0Semi standard non polar33892256
Norketamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2332.3Standard non polar33892256
Norketamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2607.7Standard polar33892256
Norketamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2478.9Semi standard non polar33892256
Norketamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2575.9Standard non polar33892256
Norketamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2578.7Standard polar33892256
Norketamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2756.7Semi standard non polar33892256
Norketamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2588.7Standard non polar33892256
Norketamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCCCC1(C1=CC=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2598.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norketamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-3900000000-634f9a2fc456876553612017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norketamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norketamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Norketamine LC-ESI-QTOF , positive-QTOFsplash10-004i-0910000000-bf7767d5610fb89d11632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norketamine -1V, Positive-QTOFsplash10-004i-0910000000-31e439bc58fec1dca3d32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 10V, Positive-QTOFsplash10-00di-0190000000-34d7dbeba5517cc4d4332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 20V, Positive-QTOFsplash10-05g3-2970000000-a2d6a08741e2682c278c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 40V, Positive-QTOFsplash10-000l-2900000000-12ec681e1efb87105add2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 10V, Negative-QTOFsplash10-00di-0190000000-660fd586450712acfd622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 20V, Negative-QTOFsplash10-00di-0690000000-d9e376a6423971536f9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 40V, Negative-QTOFsplash10-08fr-3910000000-39136f1d4f3df9d0bfba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 10V, Positive-QTOFsplash10-0ab9-0190000000-41b295d69ca0110a190d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 20V, Positive-QTOFsplash10-0a4r-0960000000-dbf224f9560e0e536ff12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 40V, Positive-QTOFsplash10-000f-5900000000-9c3593706147f884d0322021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 10V, Negative-QTOFsplash10-00di-0090000000-604d972afe0057708dd02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 20V, Negative-QTOFsplash10-022c-6980000000-d8497d3e0e9cf8a537d62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norketamine 40V, Negative-QTOFsplash10-001i-9300000000-a6e7f53d610b37821bea2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorketamine
METLIN IDNot Available
PubChem Compound123767
PDB IDNot Available
ChEBI ID91519
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 ReferencesNot Available