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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:34 UTC
Update Date2019-07-23 06:35:13 UTC
HMDB IDHMDB0041913
Secondary Accession Numbers
  • HMDB41913
Metabolite Identification
Common NameKetobemidone
DescriptionKetobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted by its metabolite norketobemidone. This makes it useful for some types of pain that don't respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection. Ketobemidone is 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. It is usually available as the hydrochloride, which is a white powder. It is synthesized by alkylating (3-methoxyphenyl)acetonitrile with bis(2-chloroethyl)methylamine, followed by reaction with ethylmagnesiumbromide, and finally O-demethylation with hydrobromic acid.
Structure
Data?1563863713
Synonyms
ValueSource
KetodurHMDB
CetobemidoneHMDB
CliradonHMDB
KetoganHMDB
CymidonHMDB
KetoraxHMDB
1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanoneHMDB
1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanoneHMDB
4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketoneHMDB
4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidineHMDB
a 21 LundbeckHMDB
CetobemidonHMDB
CliradoneHMDB
Ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketoneHMDB
Ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketoneHMDB
Ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidylHMDB
{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}HMDB
Ketobemidone hydrochlorideHMDB
Chemical FormulaC15H21NO2
Average Molecular Weight247.3327
Monoisotopic Molecular Weight247.157228921
IUPAC Name1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
Traditional Nameketobemidone
CAS Registry Number469-79-4
SMILES
CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
InChI KeyALFGKMXHOUSVAD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Gamma-aminoketone
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM159.730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.01 g/LALOGPS
logP10(2.01) g/LALOGPS
logP10(2.49) g/LChemAxon
logS10(-1.9) g/LALOGPS
pKa (Strongest Acidic)9.44ChemAxon
pKa (Strongest Basic)8.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.12 m³·mol⁻¹ChemAxon
Polarizability28.09 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
DarkChem[M+H]+159.73531661259
DarkChem[M-H]-158.5131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KetobemidoneCCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C12825.5Standard polar33892256
KetobemidoneCCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C12035.7Standard non polar33892256
KetobemidoneCCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C12066.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ketobemidone,1TMS,isomer #1CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC12024.2Semi standard non polar33892256
Ketobemidone,1TMS,isomer #2CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O)=C2)CCN(C)CC12089.0Semi standard non polar33892256
Ketobemidone,2TMS,isomer #1CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC12076.6Semi standard non polar33892256
Ketobemidone,2TMS,isomer #1CC=C(O[Si](C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C)=C2)CCN(C)CC12095.0Standard non polar33892256
Ketobemidone,1TBDMS,isomer #1CCC(=O)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN(C)CC12242.8Semi standard non polar33892256
Ketobemidone,1TBDMS,isomer #2CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O)=C2)CCN(C)CC12319.4Semi standard non polar33892256
Ketobemidone,2TBDMS,isomer #1CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN(C)CC12457.4Semi standard non polar33892256
Ketobemidone,2TBDMS,isomer #1CC=C(O[Si](C)(C)C(C)(C)C)C1(C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)CCN(C)CC12571.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ketobemidone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3910000000-6decb78c046347ae40f52017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketobemidone GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3091000000-0cf23890669092455f922017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketobemidone 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 - Ketobemidone 10V, Positive-QTOFsplash10-0002-0090000000-b0eb6846d8434b71e1632017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 20V, Positive-QTOFsplash10-0002-2390000000-41423312ecf719c689d02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 40V, Positive-QTOFsplash10-074m-5910000000-e7966d50007a351d14e92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 10V, Negative-QTOFsplash10-0002-0090000000-18564889dbd2dc37a4072017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 20V, Negative-QTOFsplash10-0002-2190000000-015e225df40c337cafe32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 40V, Negative-QTOFsplash10-000x-8940000000-c9ccc1d7e952deff93322017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 10V, Negative-QTOFsplash10-0002-0090000000-3354f6c46a82b7831c662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 20V, Negative-QTOFsplash10-0007-0390000000-315f6deebbaff449f32b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 40V, Negative-QTOFsplash10-000f-4950000000-5a925ef84d658e2cc8a52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 10V, Positive-QTOFsplash10-0002-0090000000-15bdb7d2e15247b507222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 20V, Positive-QTOFsplash10-000t-2960000000-9309f7fbca98854bbc292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketobemidone 40V, Positive-QTOFsplash10-006y-6910000000-e8a557226f34163f31e72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDDB06738
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9697
KEGG Compound IDC11792
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKetobemidone
METLIN IDNot Available
PubChem Compound10101
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