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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:51:51 UTC
Update Date2019-07-23 06:35:20 UTC
HMDB IDHMDB0041989
Secondary Accession Numbers
  • HMDB41989
Metabolite Identification
Common NamePipemidic acid
DescriptionPipemidic acid, also known as acide pipemidique or nuril, belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group. Based on a literature review a significant number of articles have been published on Pipemidic acid.
Structure
Data?1563863720
Synonyms
ValueSource
5,8-Dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylic acidChEBI
8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylic acidChEBI
Acide pipemidiqueChEBI
Acido pipemidicoChEBI
Acidum pipemidicumChEBI
NurilKegg
5,8-Dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylateGenerator
8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylateGenerator
PipemidateGenerator
Pipemidic acid hydrateHMDB
PPAHMDB
DeblastonHMDB
PalinHMDB
UrisanHMDB
AF brand OF pipemidic acidHMDB
Acid, pipemidicHMDB
Aventis brand OF pipemidic acidHMDB
Madaus brand OF pipemidic acidHMDB
Acid, piperamicHMDB
GalusanHMDB
Piperamic acidHMDB
Rhône-poulenc brand OF pipemidic acidHMDB
Tedec meiji brand OF pipemidic acidHMDB
UropipemidHMDB
Almirall brand OF pipemidic acidHMDB
PipramHMDB
Chemical FormulaC14H17N5O3
Average Molecular Weight303.3165
Monoisotopic Molecular Weight303.133139435
IUPAC Name8-ethyl-5-oxo-2-(piperazin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid
Traditional Namepipemidic acid
CAS Registry Number51940-44-4
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCNCC1
InChI Identifier
InChI=1S/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22)
InChI KeyJOHZPMXAZQZXHR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Pyrido[2,3-d]pyrimidine
  • Pyridopyrimidine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyrimidine
  • Pyridine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point253 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 mg/mL at 25 °CNot Available
LogP-2.15Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available171.01http://allccs.zhulab.cn/database/detail?ID=AllCCS00001116
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP10(-1.5) g/LALOGPS
logP10(-1.8) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)5.31ChemAxon
pKa (Strongest Basic)8.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.18 m³·mol⁻¹ChemAxon
Polarizability30.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.84431661259
DarkChem[M-H]-172.86831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pipemidic acidCCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCNCC13250.8Standard polar33892256
Pipemidic acidCCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCNCC12769.5Standard non polar33892256
Pipemidic acidCCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCNCC13172.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pipemidic acid,1TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CN=C(N3CCNCC3)N=C212874.4Semi standard non polar33892256
Pipemidic acid,1TMS,isomer #2CCN1C=C(C(=O)O)C(=O)C2=CN=C(N3CCN([Si](C)(C)C)CC3)N=C213119.2Semi standard non polar33892256
Pipemidic acid,2TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CN=C(N3CCN([Si](C)(C)C)CC3)N=C212995.7Semi standard non polar33892256
Pipemidic acid,2TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CN=C(N3CCN([Si](C)(C)C)CC3)N=C213058.1Standard non polar33892256
Pipemidic acid,1TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CN=C(N3CCNCC3)N=C213081.2Semi standard non polar33892256
Pipemidic acid,1TBDMS,isomer #2CCN1C=C(C(=O)O)C(=O)C2=CN=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213343.6Semi standard non polar33892256
Pipemidic acid,2TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CN=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213377.7Semi standard non polar33892256
Pipemidic acid,2TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CN=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213444.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pipemidic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-2890000000-fa2626fd59959165a5102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipemidic acid GC-MS (1 TMS) - 70eV, Positivesplash10-03ka-4094000000-78fcdd6a223856eb07522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipemidic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pipemidic acid 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 - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-0udi-0009000000-f346d0fa8518f6309a432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-0uxr-0069000000-ffff1a7a9577a098fda02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-0gb9-0294000000-545852783e7d4b0ad3142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-014r-0592000000-b4be933137c73df3a3552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-00kr-0950000000-28374d85a72be7c7b33e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid LC-ESI-QFT , positive-QTOFsplash10-01pa-1920000000-a1ae9ea00fc1f72489712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 45V, Positive-QTOFsplash10-0gb9-0194000000-f6db3736a8f17fd279c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 30V, Positive-QTOFsplash10-0uxr-0069000000-45ebd376bace5bfd88b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 75V, Positive-QTOFsplash10-00kr-0950000000-3a6f73ec7e09a3d411b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 60V, Positive-QTOFsplash10-014r-0592000000-1db74d5d3d057d54dd812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 90V, Positive-QTOFsplash10-01pa-1920000000-69758e718c3313dea3142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pipemidic acid 15V, Positive-QTOFsplash10-0udi-0009000000-20bf825f337370ca206e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 10V, Positive-QTOFsplash10-0udi-0079000000-5a013f059de02bd43b1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 20V, Positive-QTOFsplash10-0ly9-0091000000-2c533b71f29aaba42ae62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 40V, Positive-QTOFsplash10-007p-2290000000-96fe0e6b043582a86bb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 10V, Negative-QTOFsplash10-0pb9-0094000000-2b7d148c2a2a3d9a7ede2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 20V, Negative-QTOFsplash10-053r-0090000000-67a70251083cbdc674052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 40V, Negative-QTOFsplash10-01sl-2590000000-bc4f2f1768f8d07890f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 10V, Positive-QTOFsplash10-0udi-0029000000-cabcb3cf1aa477a1bb272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 20V, Positive-QTOFsplash10-000i-0090000000-6cc5acde39ab0e0d48f42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 40V, Positive-QTOFsplash10-0a4l-0090000000-4922b0b51bbfdd6f9b2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 10V, Negative-QTOFsplash10-0pc0-0092000000-4f0b52545c468b781cef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 20V, Negative-QTOFsplash10-0059-0090000000-ab98a90941c608d79b972021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pipemidic acid 40V, Negative-QTOFsplash10-01u0-0690000000-2c7c1c62a3923e9b609f2021-09-25Wishart 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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13823
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4665
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPipemidic_acid
METLIN IDNot Available
PubChem Compound4831
PDB IDNot Available
ChEBI ID75250
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. Llorent-Martinez EJ, Ortega-Barrales P, Molina-Diaz A: Multicommuted optosensor for the determination of pipemidic acid in biological fluids. Anal Biochem. 2005 Dec 15;347(2):330-2. Epub 2005 Oct 7. [PubMed:16259938 ]
  2. Sun H, Li L, Su M: Simultaneous determination of proline and pipemidic acid in human urine by capillary electrophoresis with electrochemiluminescence detection. J Clin Lab Anal. 2010;24(5):327-33. doi: 10.1002/jcla.20284. [PubMed:20872568 ]
  3. Iacovino R, Rapuano F, Caso JV, Russo A, Lavorgna M, Russo C, Isidori M, Russo L, Malgieri G, Isernia C: beta-Cyclodextrin inclusion complex to improve physicochemical properties of pipemidic acid: characterization and bioactivity evaluation. Int J Mol Sci. 2013 Jun 25;14(7):13022-41. doi: 10.3390/ijms140713022. [PubMed:23799358 ]
  4. Azanza Perea JR, Honorato Perez JM, Cuena Boy R: [Pipemidic acid]. Rev Med Univ Navarra. 1982 Jun;26(2):55-6. [PubMed:7178752 ]