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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:19:09 UTC
Update Date2021-09-26 23:01:43 UTC
HMDB IDHMDB0250315
Secondary Accession NumbersNone
Metabolite Identification
Common NameClebopride
DescriptionClebopride, also known as cleboril, belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom. Based on a literature review very few articles have been published on Clebopride. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clebopride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clebopride is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
CleborilKegg
CLEBOPRIDE malATEChEMBL
LAS 9273ChEMBL
CLEBOPRIDE malic acidGenerator
Clebopride mono-hydrochlorideMeSH
N-1-Benzyl-4 piperidil-3-methoxy-4-amino-5-chlorobenzamideMeSH
Clebopride fumarate (1:1)MeSH
Clebopride maleateMeSH
Clebopride maleate (1:1)MeSH
Chemical FormulaC20H24ClN3O2
Average Molecular Weight373.88
Monoisotopic Molecular Weight373.1557047
IUPAC Name4-amino-N-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxybenzamide
Traditional Nameclebopride
CAS Registry NumberNot Available
SMILES
COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC1
InChI Identifier
InChI=1S/C20H24ClN3O2/c1-26-19-12-18(22)17(21)11-16(19)20(25)23-15-7-9-24(10-8-15)13-14-5-3-2-4-6-14/h2-6,11-12,15H,7-10,13,22H2,1H3,(H,23,25)
InChI KeyBVPWJMCABCPUQY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassBenzylpiperidines
Direct ParentN-benzylpiperidines
Alternative Parents
Substituents
  • N-benzylpiperidine
  • Methoxyaniline
  • Aminophenyl ether
  • Anisole
  • Benzylamine
  • Phenol ether
  • Phenylmethylamine
  • Aniline or substituted anilines
  • Phenoxy compound
  • Methoxybenzene
  • Aralkylamine
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • 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
logP2.69ALOGPS
logP2.42ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)14.61ChemAxon
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.07 m³·mol⁻¹ChemAxon
Polarizability39.81 ųChemAxon
Number of Rings3ChemAxon
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]+188.56330932474
DeepCCS[M-H]-186.00630932474
DeepCCS[M-2H]-220.49730932474
DeepCCS[M+Na]+196.18730932474
AllCCS[M+H]+188.632859911
AllCCS[M+H-H2O]+186.032859911
AllCCS[M+NH4]+191.132859911
AllCCS[M+Na]+191.832859911
AllCCS[M-H]-187.532859911
AllCCS[M+Na-2H]-187.732859911
AllCCS[M+HCOO]-188.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CleboprideCOC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC14006.7Standard polar33892256
CleboprideCOC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13243.2Standard non polar33892256
CleboprideCOC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13490.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clebopride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13334.1Semi standard non polar33892256
Clebopride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC12070.9Standard non polar33892256
Clebopride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13999.8Standard polar33892256
Clebopride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C3160.8Semi standard non polar33892256
Clebopride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C2021.6Standard non polar33892256
Clebopride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C4218.4Standard polar33892256
Clebopride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13215.7Semi standard non polar33892256
Clebopride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC12244.1Standard non polar33892256
Clebopride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13861.5Standard polar33892256
Clebopride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C3223.2Semi standard non polar33892256
Clebopride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C2062.7Standard non polar33892256
Clebopride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C3882.1Standard polar33892256
Clebopride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C3140.4Semi standard non polar33892256
Clebopride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C2280.0Standard non polar33892256
Clebopride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C3697.0Standard polar33892256
Clebopride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13515.1Semi standard non polar33892256
Clebopride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC12269.4Standard non polar33892256
Clebopride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC14090.8Standard polar33892256
Clebopride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C3353.9Semi standard non polar33892256
Clebopride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C2198.8Standard non polar33892256
Clebopride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C4263.5Standard polar33892256
Clebopride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13626.3Semi standard non polar33892256
Clebopride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC12676.3Standard non polar33892256
Clebopride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CCN(CC2=CC=CC=C2)CC13963.9Standard polar33892256
Clebopride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C3603.7Semi standard non polar33892256
Clebopride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C2524.5Standard non polar33892256
Clebopride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C4012.9Standard polar33892256
Clebopride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C3694.7Semi standard non polar33892256
Clebopride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C2975.7Standard non polar33892256
Clebopride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CCN(CC2=CC=CC=C2)CC1)[Si](C)(C)C(C)(C)C3852.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clebopride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9741000000-ef5fce10744ade1e093a2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clebopride 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 - Clebopride 10V, Positive-QTOFsplash10-00dl-3309000000-a1a51e9c4a09d6db5d852017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 20V, Positive-QTOFsplash10-0006-9812000000-fd4961a2b80d337c8f782017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 40V, Positive-QTOFsplash10-0006-9100000000-e77f234761451d0c7f272017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 10V, Negative-QTOFsplash10-00di-0119000000-e57ac8d9598bcc8dc8732017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 20V, Negative-QTOFsplash10-05fr-1549000000-46f88985ade25be1cd122017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 40V, Negative-QTOFsplash10-054n-6920000000-d9d32cd679178a5d07522017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 10V, Positive-QTOFsplash10-00di-0009000000-bebb020dfacd37095aa72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 20V, Positive-QTOFsplash10-0089-1908000000-7c91ae1864a4be36bb492021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 40V, Positive-QTOFsplash10-0006-9301000000-07ad9a8b55d060fc33172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 10V, Negative-QTOFsplash10-00di-0109000000-2c22786e7b3e575b844e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 20V, Negative-QTOFsplash10-00di-2009000000-b517791206da69b787632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clebopride 40V, Negative-QTOFsplash10-0fl3-5395000000-077ea36b3d74740c1f2a2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13511
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2678
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClebopride
METLIN IDNot Available
PubChem CompoundNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]