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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 17:30:05 UTC
Update Date2021-09-26 23:12:52 UTC
HMDB IDHMDB0256880
Secondary Accession NumbersNone
Metabolite Identification
Common NamePrucalopride
DescriptionPrucalopride belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Based on a literature review a significant number of articles have been published on Prucalopride. This compound has been identified in human blood as reported by (PMID: 31557052 ). Prucalopride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Prucalopride 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
R-093877PrucaloprideChEMBL
ResotransMeSH
ResolorMeSH
ResotranMeSH
4-Amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboximidateGenerator
4-Amino-5-chloro-N-(1-(3-methoxypropyl)-4-piperidinyl)-2,3-dihydro-1-benzofuran-7-carboxamideMeSH
Chemical FormulaC18H26ClN3O3
Average Molecular Weight367.87
Monoisotopic Molecular Weight367.1662694
IUPAC Name4-amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
Traditional Nameprucalopride
CAS Registry NumberNot Available
SMILES
COCCCN1CCC(CC1)NC(=O)C1=C2OCCC2=C(N)C(Cl)=C1
InChI Identifier
InChI=1S/C18H26ClN3O3/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14/h11-12H,2-10,20H2,1H3,(H,21,23)
InChI KeyZPMNHBXQOOVQJL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzamides
Alternative Parents
Substituents
  • Aminobenzamide
  • Coumaran
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxide
  • 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
logP2.09ALOGPS
logP0.74ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.64ChemAxon
pKa (Strongest Basic)8.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.67 m³·mol⁻¹ChemAxon
Polarizability39.08 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.29330932474
DeepCCS[M-H]-191.93530932474
DeepCCS[M-2H]-224.82130932474
DeepCCS[M+Na]+200.38630932474
AllCCS[M+H]+184.932859911
AllCCS[M+H-H2O]+182.332859911
AllCCS[M+NH4]+187.332859911
AllCCS[M+Na]+188.032859911
AllCCS[M-H]-184.932859911
AllCCS[M+Na-2H]-185.432859911
AllCCS[M+HCOO]-186.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PrucaloprideCOCCCN1CCC(CC1)NC(=O)C1=C2OCCC2=C(N)C(Cl)=C14113.7Standard polar33892256
PrucaloprideCOCCCN1CCC(CC1)NC(=O)C1=C2OCCC2=C(N)C(Cl)=C13161.5Standard non polar33892256
PrucaloprideCOCCCN1CCC(CC1)NC(=O)C1=C2OCCC2=C(N)C(Cl)=C13545.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prucalopride,1TMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)CC13172.5Semi standard non polar33892256
Prucalopride,1TMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)CC12902.2Standard non polar33892256
Prucalopride,1TMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)CC14289.8Standard polar33892256
Prucalopride,1TMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C)CC13007.0Semi standard non polar33892256
Prucalopride,1TMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C)CC12954.0Standard non polar33892256
Prucalopride,1TMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C)CC14626.8Standard polar33892256
Prucalopride,2TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC13087.9Semi standard non polar33892256
Prucalopride,2TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC12966.3Standard non polar33892256
Prucalopride,2TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC14025.6Standard polar33892256
Prucalopride,2TMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)CC13102.6Semi standard non polar33892256
Prucalopride,2TMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)CC12986.7Standard non polar33892256
Prucalopride,2TMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)CC13964.8Standard polar33892256
Prucalopride,3TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC13048.0Semi standard non polar33892256
Prucalopride,3TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC13050.6Standard non polar33892256
Prucalopride,3TMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2OCC3)[Si](C)(C)C)CC13682.5Standard polar33892256
Prucalopride,1TBDMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC13352.0Semi standard non polar33892256
Prucalopride,1TBDMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC13134.9Standard non polar33892256
Prucalopride,1TBDMS,isomer #1COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC14293.3Standard polar33892256
Prucalopride,1TBDMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13208.4Semi standard non polar33892256
Prucalopride,1TBDMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13170.9Standard non polar33892256
Prucalopride,1TBDMS,isomer #2COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC14612.4Standard polar33892256
Prucalopride,2TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13471.2Semi standard non polar33892256
Prucalopride,2TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13371.7Standard non polar33892256
Prucalopride,2TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC14055.6Standard polar33892256
Prucalopride,2TBDMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC13533.8Semi standard non polar33892256
Prucalopride,2TBDMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC13376.8Standard non polar33892256
Prucalopride,2TBDMS,isomer #2COCCCN1CCC(NC(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)CC13984.7Standard polar33892256
Prucalopride,3TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13677.9Semi standard non polar33892256
Prucalopride,3TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13577.9Standard non polar33892256
Prucalopride,3TBDMS,isomer #1COCCCN1CCC(N(C(=O)C2=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2OCC3)[Si](C)(C)C(C)(C)C)CC13822.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prucalopride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9812000000-f1bd170ac71ec919b4172021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prucalopride 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 - Prucalopride 10V, Positive-QTOFsplash10-014r-0309000000-de7dc5c7c5e8b2bd381c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prucalopride 20V, Positive-QTOFsplash10-05fs-4926000000-bc02ec523ae0053211322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prucalopride 40V, Positive-QTOFsplash10-00ym-8900000000-261664a7dcbdfbafb0b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prucalopride 10V, Negative-QTOFsplash10-014i-0109000000-463adb3809c2c0b711fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prucalopride 20V, Negative-QTOFsplash10-014i-3849000000-c813744bf4a58d6f13da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prucalopride 40V, Negative-QTOFsplash10-02td-4960000000-57970845cde3ad05051c2016-08-03Wishart 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 IDDB06480
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2314539
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrucalopride
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 ]