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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:50 UTC
Update Date2021-09-14 15:44:37 UTC
HMDB IDHMDB0014016
Secondary Accession Numbers
  • HMDB14016
Metabolite Identification
Common Name5-Hydroxyketamine
Description5-Hydroxyketamine is only found in individuals that have used or taken Ketamine. 5-Hydroxyketamine is a metabolite of Ketamine. 5-hydroxyketamine belongs to the family of Phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Structure
Data?1582753160
SynonymsNot Available
Chemical FormulaC13H16ClNO2
Average Molecular Weight253.725
Monoisotopic Molecular Weight253.086956468
IUPAC Name2-(2-chlorophenyl)-5-hydroxy-2-(methylamino)cyclohexan-1-one
Traditional Name2-(2-chlorophenyl)-5-hydroxy-2-(methylamino)cyclohexan-1-one
CAS Registry NumberNot Available
SMILES
CNC1(CCC(O)CC1=O)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C13H16ClNO2/c1-15-13(7-6-9(16)8-12(13)17)10-4-2-3-5-11(10)14/h2-5,9,15-16H,6-8H2,1H3
InChI KeyGJRAGJDIUMHOLU-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
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

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 Solubility0.86 g/LALOGPS
logP1.31ALOGPS
logP2.12ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.87ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.07 m³·mol⁻¹ChemAxon
Polarizability25.82 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]+156.31730932474
DeepCCS[M-H]-153.95930932474
DeepCCS[M-2H]-187.57530932474
DeepCCS[M+Na]+162.58430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxyketamineCNC1(CCC(O)CC1=O)C1=CC=CC=C1Cl2869.5Standard polar33892256
5-HydroxyketamineCNC1(CCC(O)CC1=O)C1=CC=CC=C1Cl1947.1Standard non polar33892256
5-HydroxyketamineCNC1(CCC(O)CC1=O)C1=CC=CC=C1Cl2058.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxyketamine,1TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)CC1=O2025.9Semi standard non polar33892256
5-Hydroxyketamine,1TMS,isomer #2CNC1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C2069.6Semi standard non polar33892256
5-Hydroxyketamine,1TMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)CC1=O)[Si](C)(C)C2121.3Semi standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C2080.2Semi standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C2125.1Standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C2512.1Standard polar33892256
5-Hydroxyketamine,2TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)CC1=O)[Si](C)(C)C2137.3Semi standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)CC1=O)[Si](C)(C)C2257.7Standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)CC1=O)[Si](C)(C)C2514.6Standard polar33892256
5-Hydroxyketamine,2TMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C)[Si](C)(C)C2150.8Semi standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C)[Si](C)(C)C2080.7Standard non polar33892256
5-Hydroxyketamine,2TMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C)[Si](C)(C)C2662.9Standard polar33892256
5-Hydroxyketamine,3TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C)[Si](C)(C)C2163.5Semi standard non polar33892256
5-Hydroxyketamine,3TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C)[Si](C)(C)C2160.7Standard non polar33892256
5-Hydroxyketamine,3TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C)C=C1O[Si](C)(C)C)[Si](C)(C)C2423.2Standard polar33892256
5-Hydroxyketamine,1TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)CC1=O2264.9Semi standard non polar33892256
5-Hydroxyketamine,1TBDMS,isomer #2CNC1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C(C)(C)C2293.5Semi standard non polar33892256
5-Hydroxyketamine,1TBDMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)CC1=O)[Si](C)(C)C(C)(C)C2362.1Semi standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2499.0Semi standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2498.3Standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2712.9Standard polar33892256
5-Hydroxyketamine,2TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)CC1=O)[Si](C)(C)C(C)(C)C2614.1Semi standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)CC1=O)[Si](C)(C)C(C)(C)C2734.6Standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)CC1=O)[Si](C)(C)C(C)(C)C2699.2Standard polar33892256
5-Hydroxyketamine,2TBDMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2603.7Semi standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2457.4Standard non polar33892256
5-Hydroxyketamine,2TBDMS,isomer #3CN(C1(C2=CC=CC=C2Cl)CCC(O)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2825.9Standard polar33892256
5-Hydroxyketamine,3TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2846.5Semi standard non polar33892256
5-Hydroxyketamine,3TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2691.4Standard non polar33892256
5-Hydroxyketamine,3TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCC(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2686.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyketamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-0900000000-0acaaad978af22c961cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyketamine GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-1900000000-a8ef515ad9e9c24629ad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyketamine 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 - 5-Hydroxyketamine 10V, Negative-QTOFsplash10-0udi-0190000000-7d7160489c376d10a3ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 20V, Negative-QTOFsplash10-0udi-0390000000-a848cfe5f85b17e626f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 40V, Negative-QTOFsplash10-03dr-3910000000-f49242b778fc8ab3c55d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 10V, Negative-QTOFsplash10-0udi-0190000000-23d9fb7129437be4c08b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 20V, Negative-QTOFsplash10-0nnd-6690000000-a8638289182a8c1aeb6d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 40V, Negative-QTOFsplash10-000w-9200000000-0b3fa3572f6f3bc8739e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 10V, Positive-QTOFsplash10-0f79-0190000000-88bff940906f773e2da52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 20V, Positive-QTOFsplash10-0f79-0290000000-2d55a68ad1a482a0bf4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 40V, Positive-QTOFsplash10-0v7i-2900000000-e3c1175545301b98f71a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 10V, Positive-QTOFsplash10-0udi-0090000000-a4216246b3a4c41d09562021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 20V, Positive-QTOFsplash10-0pi9-0490000000-eb4f5d63bf631bd0c3e72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyketamine 40V, Positive-QTOFsplash10-0udi-2910000000-429245294b5d55f39f752021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 ID35032781
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound118753542
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 ReferencesNot Available