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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:08 UTC
Update Date2019-07-23 07:15:50 UTC
HMDB IDHMDB0061135
Secondary Accession Numbers
  • HMDB61135
Metabolite Identification
Common NameDemonomethylchlorpromazine
DescriptionDemonomethylchlorpromazine is a metabolite of chlorpromazine. Chlorpromazine (as chlorpromazine hydrochloride, abbreviated CPZ; marketed in the United States as Thorazine and elsewhere as Largactil) is a typical antipsychotic. First synthesized on December 11, 1950, chlorpromazine was the first drug developed with specific antipsychotic action, and would serve as the prototype for the phenothiazine class of drugs, which later grew to comprise several other agents. (Wikipedia)
Structure
Data?1563866150
Synonyms
ValueSource
Norchlorpromazine perchlorate, ion(1+)HMDB
N-MonodesmethylchlorpromazineHMDB
Norchlorpromazine, ion(1+)HMDB
Norchlorpromazine maleateHMDB
N-DesmethylchlorpromazineHMDB
Norchlorpromazine hydrochlorideHMDB
Norchlorpromazine monomaleateHMDB
Chemical FormulaC16H17ClN2S
Average Molecular Weight304.838
Monoisotopic Molecular Weight304.080096951
IUPAC Name[3-(2-chloro-10H-phenothiazin-10-yl)propyl](methyl)amine
Traditional Name[3-(2-chlorophenothiazin-10-yl)propyl](methyl)amine
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2
InChI Identifier
InChI=1S/C16H17ClN2S/c1-18-9-4-10-19-13-5-2-3-6-15(13)20-16-8-7-12(17)11-14(16)19/h2-3,5-8,11,18H,4,9-10H2,1H3
InChI KeyYHFXGBOUSIKGMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Tertiary aliphatic/aromatic amine
  • Aryl thioether
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Para-thiazine
  • Tertiary amine
  • Thioether
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.0051 g/LALOGPS
logP4.27ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.46 m³·mol⁻¹ChemAxon
Polarizability32.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+167.34330932474
DeepCCS[M-H]-164.98530932474
DeepCCS[M-2H]-197.87130932474
DeepCCS[M+Na]+173.43630932474
AllCCS[M+H]+166.532859911
AllCCS[M+H-H2O]+163.332859911
AllCCS[M+NH4]+169.532859911
AllCCS[M+Na]+170.432859911
AllCCS[M-H]-166.432859911
AllCCS[M+Na-2H]-165.732859911
AllCCS[M+HCOO]-165.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemonomethylchlorpromazineCNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C23624.5Standard polar33892256
DemonomethylchlorpromazineCNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C22531.1Standard non polar33892256
DemonomethylchlorpromazineCNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C22553.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demonomethylchlorpromazine,1TMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C2704.2Semi standard non polar33892256
Demonomethylchlorpromazine,1TMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C2821.2Standard non polar33892256
Demonomethylchlorpromazine,1TMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C3404.4Standard polar33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C2925.2Semi standard non polar33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3050.7Standard non polar33892256
Demonomethylchlorpromazine,1TBDMS,isomer #1CN(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3488.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demonomethylchlorpromazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6190000000-7064bdabc610ca9935f52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demonomethylchlorpromazine 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 - Demonomethylchlorpromazine 10V, Positive-QTOFsplash10-0ab9-1059000000-f303e6242cff85b0f9df2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Positive-QTOFsplash10-00di-6094000000-7b134b7d8070a91bd7ac2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Positive-QTOFsplash10-000x-9140000000-39465a7f6fe6a1a2470a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Negative-QTOFsplash10-0udi-0019000000-6c714d0b3a8c7f6d1fa82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Negative-QTOFsplash10-0zgl-0955000000-d24dce6613357abb00222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Negative-QTOFsplash10-001i-2190000000-1220ae1f2fdd7f153d922017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Positive-QTOFsplash10-0a4i-0019000000-f03d078306d1b29f51742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Positive-QTOFsplash10-00di-2093000000-ecda4ce97a5cd75afdc32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Positive-QTOFsplash10-008m-0090000000-f3c65ad967db394beacf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 10V, Negative-QTOFsplash10-0udi-0009000000-bb22079884d9b4d9be3a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 20V, Negative-QTOFsplash10-0ue9-1079000000-9c070ebad6ae191c4cdc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demonomethylchlorpromazine 40V, Negative-QTOFsplash10-001i-2190000000-f3969c8556a31959e7702021-09-23Wishart 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 LinkNot Available
METLIN IDNot Available
PubChem Compound62875
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