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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:14 UTC
Update Date2019-07-23 07:15:20 UTC
HMDB IDHMDB0060902
Secondary Accession Numbers
  • HMDB60902
Metabolite Identification
Common Name4-(4-chlorophenyl)-4-hydroxypiperidine
Description4-(4-chlorophenyl)-4-hydroxypiperidine, also known as 4-CPPO, 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. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. 4-(4-chlorophenyl)-4-hydroxypiperidine is a metabolite of haloperidol. 4-(4-chlorophenyl)-4-hydroxypiperidine is a very strong basic compound (based on its pKa). Haloperidol is an older antipsychotic used in the treatment of schizophrenia and acute psychotic states and delirium. Haloperidol is a typical antipsychotic.
Structure
Data?1563866120
Synonyms
ValueSource
4-(4'-Chlorophenyl)-4-piperidinolHMDB
4-CPPOHMDB
HCL OF 4-(4'-Chlorophenyl)-4-piperidinolHMDB
4-(4-Chlorophenyl)-4-hydroxypiperidineMeSH
Chemical FormulaC11H14ClNO
Average Molecular Weight211.688
Monoisotopic Molecular Weight211.076391782
IUPAC Name4-(4-chlorophenyl)piperidin-4-ol
Traditional Name4-(4-chlorophenyl)piperidin-4-ol
CAS Registry NumberNot Available
SMILES
OC1(CCNCC1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C11H14ClNO/c12-10-3-1-9(2-4-10)11(14)5-7-13-8-6-11/h1-4,13-14H,5-8H2
InChI KeyLZAYOZUFUAMFLD-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
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility1.26 g/LALOGPS
logP1.82ALOGPS
logP1.38ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.72 m³·mol⁻¹ChemAxon
Polarizability22.22 ųChemAxon
Number of Rings2ChemAxon
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]+143.51930932474
DeepCCS[M-H]-140.66730932474
DeepCCS[M-2H]-176.82730932474
DeepCCS[M+Na]+152.36230932474
AllCCS[M+H]+146.132859911
AllCCS[M+H-H2O]+142.032859911
AllCCS[M+NH4]+150.032859911
AllCCS[M+Na]+151.232859911
AllCCS[M-H]-148.732859911
AllCCS[M+Na-2H]-149.332859911
AllCCS[M+HCOO]-149.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(4-chlorophenyl)-4-hydroxypiperidineOC1(CCNCC1)C1=CC=C(Cl)C=C12456.6Standard polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidineOC1(CCNCC1)C1=CC=C(Cl)C=C11825.1Standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidineOC1(CCNCC1)C1=CC=C(Cl)C=C11834.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(4-chlorophenyl)-4-hydroxypiperidine,1TMS,isomer #1C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCNCC11825.1Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,1TMS,isomer #2C[Si](C)(C)N1CCC(O)(C2=CC=C(Cl)C=C2)CC11959.3Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TMS,isomer #1C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C)CC11946.0Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TMS,isomer #1C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C)CC12039.4Standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TMS,isomer #1C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C)CC12300.9Standard polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCNCC12069.1Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1CCC(O)(C2=CC=C(Cl)C=C2)CC12218.3Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C(C)(C)C)CC12431.7Semi standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C(C)(C)C)CC12506.9Standard non polar33892256
4-(4-chlorophenyl)-4-hydroxypiperidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)CCN([Si](C)(C)C(C)(C)C)CC12524.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine EI-B (Non-derivatized)splash10-052f-9400000000-5958c2e8aa283789e1612017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine EI-B (Non-derivatized)splash10-052f-9400000000-5958c2e8aa283789e1612018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-7900000000-c95e892ebee768e25bd72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9750000000-7b8e4e49a99c60714cd52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 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 - 4-(4-chlorophenyl)-4-hydroxypiperidine 10V, Positive-QTOFsplash10-01ox-0970000000-5fcb13002dd132f70c1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 20V, Positive-QTOFsplash10-01ox-3940000000-a3d6f6302e652bb008222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 40V, Positive-QTOFsplash10-0a5c-9700000000-1ba1fad6dc2bb8f72d942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 10V, Negative-QTOFsplash10-03di-0290000000-be9280d8a1a2e2ea20272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 20V, Negative-QTOFsplash10-03di-3890000000-302b4b057a9009642bc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 40V, Negative-QTOFsplash10-03k9-6900000000-a8610fe6ece9f56ae4d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 10V, Positive-QTOFsplash10-01ox-0970000000-aac2f9206a393eb46a402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 20V, Positive-QTOFsplash10-03xu-1940000000-e1c38d61c6ea3b593ff12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 40V, Positive-QTOFsplash10-03dr-1900000000-6247ae622f98bb01297c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 10V, Negative-QTOFsplash10-03di-1090000000-2b240f39959ae1c8f5052021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 20V, Negative-QTOFsplash10-01ox-2960000000-cab59a7f489df7fc9b912021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-chlorophenyl)-4-hydroxypiperidine 40V, Negative-QTOFsplash10-0ue9-4900000000-a351d543534730ba03b82021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 Compound38282
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