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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:51:51 UTC
Update Date2017-12-07 04:30:04 UTC
HMDB IDHMDB0041989
Secondary Accession Numbers
  • HMDB41989
Metabolite Identification
Common NamePipemidic acid
DescriptionPipemidic acid, also known as nuril or acide pipemidique, 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. Pipemidic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral.
Structure
Thumb
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
5,8-dihydro-8-Ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylateGenerator
PipemidateGenerator
8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-D)pyrimidine-6-carboxylateGenerator
Pipemidic acid hydrateHMDB
PPAHMDB
DeblastonMeSH
PalinMeSH
UrisanMeSH
AF brand OF pipemidic acidMeSH
Acid, pipemidicMeSH
Aventis brand OF pipemidic acidMeSH
Madaus brand OF pipemidic acidMeSH
Acid, piperamicMeSH
GalusanMeSH
NurilMeSH
Piperamic acidMeSH
Rhône-poulenc brand OF pipemidic acidMeSH
Tedec meiji brand OF pipemidic acidMeSH
UropipemidMeSH
Almirall brand OF pipemidic acidMeSH
PipramMeSH
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
DescriptionThis compound 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
Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point253 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 mg/mL at 25 °CNot Available
LogP-2.15Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP-1.5ALOGPS
logP-1.8ChemAxon
logS-2.6ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-2890000000-fa2626fd59959165a510View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03ka-4094000000-78fcdd6a223856eb0752View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0009000000-f346d0fa8518f6309a43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxr-0069000000-ffff1a7a9577a098fda0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0294000000-545852783e7d4b0ad314View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014r-0592000000-b4be933137c73df3a355View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kr-0950000000-28374d85a72be7c7b33eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01pa-1920000000-a1ae9ea00fc1f7248971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0079000000-5a013f059de02bd43b1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ly9-0091000000-2c533b71f29aaba42ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007p-2290000000-96fe0e6b043582a86bb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0094000000-2b7d148c2a2a3d9a7edeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090000000-67a70251083cbdc67405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01sl-2590000000-bc4f2f1768f8d07890f1View in MoNA
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
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 ]