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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 17:05:36 UTC
Update Date2022-11-23 22:29:18 UTC
HMDB IDHMDB0256572
Secondary Accession NumbersNone
Metabolite Identification
Common NamePiperaquine
Descriptionpiperaquine belongs to the class of organic compounds known as pyridinylpiperazines. Pyridinylpiperazines are compounds containing a pyridinylpiperazine skeleton, which consists of a pyridine linked (not fused) to a piperazine by a bond by a single bond that is not part of a ring. Based on a literature review a significant number of articles have been published on piperaquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piperaquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piperaquine 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
1,3-Bis[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propaneChEBI
PiperaquinolineChEBI
1,3-Bis(4-(7'-chloro-4'-quinoline)-1-piperazine)MeSH
1,3-Bis(1-(7-chloro-4'-quinolyl)-4'-piperazinyl)propaneMeSH
Chemical FormulaC29H32Cl2N6
Average Molecular Weight535.52
Monoisotopic Molecular Weight534.2065505
IUPAC Name7-chloro-4-(4-{3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl}piperazin-1-yl)quinoline
Traditional Namepiperaquine
CAS Registry NumberNot Available
SMILES
ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1
InChI Identifier
InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2
InChI KeyUCRHFBCYFMIWHC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinylpiperazines. Pyridinylpiperazines are compounds containing a pyridinylpiperazine skeleton, which consists of a pyridine linked (not fused) to a piperazine by a bond by a single bond that is not part of a ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPyridinylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Pyridinylpiperazine
  • Aminoquinoline
  • 4-aminoquinoline
  • Haloquinoline
  • Chloroquinoline
  • Quinoline
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Aminopyridine
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • 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
logP5.53ALOGPS
logP5.27ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.74 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity153.42 m³·mol⁻¹ChemAxon
Polarizability59.56 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+219.14930932474
DeepCCS[M-H]-216.75430932474
DeepCCS[M-2H]-249.63730932474
DeepCCS[M+Na]+225.06230932474
AllCCS[M+H]+225.332859911
AllCCS[M+H-H2O]+224.032859911
AllCCS[M+NH4]+226.632859911
AllCCS[M+Na]+226.932859911
AllCCS[M-H]-207.932859911
AllCCS[M+Na-2H]-208.732859911
AllCCS[M+HCOO]-209.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
piperaquineClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC15041.3Standard polar33892256
piperaquineClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC14403.9Standard non polar33892256
piperaquineClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC15041.8Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 10V, Positive-QTOFsplash10-000i-0000090000-40d0298556f035a4963a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 20V, Positive-QTOFsplash10-000i-0061090000-ecdf8ed3a4dfb85171912019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 40V, Positive-QTOFsplash10-00kn-1392010000-3bc550beefebd13e07212019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 10V, Negative-QTOFsplash10-001i-0000090000-5e72099d2aeaf91b81bb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 20V, Negative-QTOFsplash10-001i-0000090000-5574c2a1d5df4f47b36e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperaquine 40V, Negative-QTOFsplash10-00kb-2292130000-af9efeea5070f4f588712019-02-23Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID109031
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperaquine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID91231
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 ]