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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:15 UTC
Update Date2023-02-21 17:30:18 UTC
HMDB IDHMDB0061008
Secondary Accession Numbers
  • HMDB61008
Metabolite Identification
Common Namem-chlorophenylpiperazine (m-CPP)
Descriptionm-chlorophenylpiperazine (m-CPP) is a metabolite of trazodone. Trazodone (also sold under the brand names Desyrel, Oleptro, Beneficat, Deprax, Desirel, Molipaxin, Thombran, Trazorel, Trialodine, Trittico, and Mesyrel) is an antidepressant of the serotonin antagonist and reuptake inhibitor (SARI) class. It is a phenylpiperazine compound. Trazodone also has anxiolytic and hypnotic effects. Trazodone has considerably fewer prominent anticholinergic and sexual side effects than most of the tricyclic antidepressants (TCAs). (Wikipedia )
Structure
Data?1677000618
Synonyms
ValueSource
(m-CPP)ChEBI
m-ChlorophenylpiperazineChEBI
1-(3-Chlorophenyl)piperazineKegg
MCPPKegg
1-(3-Chlorophenyl)piperazine monohydrochlorideHMDB
1-3-CPPHMDB
3-ChlorophenylpiperazineHMDB
Dihydrochloro phenyl piperazineHMDB
m-CPPHMDB
Meta-chlorophenylpiperazineHMDB
1-(3-Chlorophenyl)piperazine dihydrochlorideHMDB
1-(m-Chlorophenyl)piperazineHMDB
Chemical FormulaC10H13ClN2
Average Molecular Weight196.677
Monoisotopic Molecular Weight196.076726133
IUPAC Name1-(3-chlorophenyl)piperazine
Traditional Namem-chlorophenylpiperazine
CAS Registry NumberNot Available
SMILES
ClC1=CC(=CC=C1)N1CCNCC1
InChI Identifier
InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2
InChI KeyVHFVKMTVMIZMIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Chlorobenzene
  • Halobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Tertiary amine
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility3.12 g/LALOGPS
logP2.07ALOGPS
logP2.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.05 m³·mol⁻¹ChemAxon
Polarizability20.87 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]+143.43830932474
DeepCCS[M-H]-141.0830932474
DeepCCS[M-2H]-176.22630932474
DeepCCS[M+Na]+150.95730932474
AllCCS[M+H]+141.632859911
AllCCS[M+H-H2O]+137.432859911
AllCCS[M+NH4]+145.632859911
AllCCS[M+Na]+146.832859911
AllCCS[M-H]-142.432859911
AllCCS[M+Na-2H]-143.032859911
AllCCS[M+HCOO]-143.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
m-chlorophenylpiperazine (m-CPP)ClC1=CC(=CC=C1)N1CCNCC12302.7Standard polar33892256
m-chlorophenylpiperazine (m-CPP)ClC1=CC(=CC=C1)N1CCNCC11746.9Standard non polar33892256
m-chlorophenylpiperazine (m-CPP)ClC1=CC(=CC=C1)N1CCNCC11732.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
m-chlorophenylpiperazine (m-CPP),1TMS,isomer #1C[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC11883.6Semi standard non polar33892256
m-chlorophenylpiperazine (m-CPP),1TMS,isomer #1C[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC11943.1Standard non polar33892256
m-chlorophenylpiperazine (m-CPP),1TMS,isomer #1C[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC12368.7Standard polar33892256
m-chlorophenylpiperazine (m-CPP),1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC12113.6Semi standard non polar33892256
m-chlorophenylpiperazine (m-CPP),1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC12175.1Standard non polar33892256
m-chlorophenylpiperazine (m-CPP),1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN(C2=CC=CC(Cl)=C2)CC12549.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - m-chlorophenylpiperazine (m-CPP) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0hig-3900000000-e12b3691e17f670a79f12017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-chlorophenylpiperazine (m-CPP) 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 - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-a6d6490a3774995747732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-dacdc382bd4b60551efd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-c498b22640780e85d0c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-6188e12d6302f0aac6ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0udj-0900000000-0307be5cc27e8b5e3d6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0900000000-4f1ffdc6559ba8ef8ab02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-ffa868d7cd2f5dd55b0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-036e27cc7151ed5587e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-cf09b776cfded257a89e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-8119dafe7571a20d6ce82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0udj-0900000000-0826be5530cb871f35762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0900000000-a55042eda43832b42f682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0900000000-c3dd0b695bc65a727bf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-ce6c9c7155861aeb31be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-QFT , positive-QTOFsplash10-0gb9-0900000000-04b37011a6b6e19ca4242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-QFT , positive-QTOFsplash10-014i-1900000000-5ea27eb4735ba042f7d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-04afb01877e4cfc977622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-2391d33f985d617108cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) LC-ESI-QFT , positive-QTOFsplash10-0f6t-0900000000-46eb898a4634d282ad5d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 10V, Positive-QTOFsplash10-0002-0900000000-cc01729cf1c20ee6abe82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 20V, Positive-QTOFsplash10-0002-1900000000-82b2d05237a59abd03c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 40V, Positive-QTOFsplash10-0f6x-4900000000-77c637b0dd1d4634a85f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 10V, Negative-QTOFsplash10-0002-0900000000-9ba38c9f09c2c942abb22016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 20V, Negative-QTOFsplash10-0002-0900000000-06af6833e772a609c5fd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-chlorophenylpiperazine (m-CPP) 40V, Negative-QTOFsplash10-0006-9600000000-7cf87f3c1c0512459bec2016-08-04Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDDB12110
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11738
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMeta-Chlorophenylpiperazine
METLIN IDNot Available
PubChem Compound1355
PDB IDNot Available
ChEBI ID10588
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