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Pyrazinic acid (M2MDB000435)

Record Information
Version2.0
Creation Date2012-05-31 13:55:22 -0600
Update Date2015-06-03 15:54:14 -0600
Secondary Accession Numbers
  • ECMDB02069
Identification
Name:Pyrazinic acid
DescriptionPyrazinic acid is a member of the chemical class known as Pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazinamide (PZA), an analog of nicotinamide, is a prodrug that requires conversion to the bactericidal compound pyrazinoic acid (POA) by the bacterial pyrazinamidase (PZase) activity of nicotinamidase to show activity against Mycobacterium tuberculosis. (PMID 10049264)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 2-Pyrazine carboxylate
  • 2-Pyrazine carboxylic acid
  • 2-Pyrazinecarboxylate
  • 2-Pyrazinecarboxylic
  • 2-Pyrazinecarboxylic acid
  • 2-Pyrazinoate
  • 2-Pyrazinoic acid
  • Paradiazinecarboxylate
  • Paradiazinecarboxylic acid
  • Piazinecarboxylate
  • Piazinecarboxylic acid
  • Pyrazinate
  • Pyrazine-2-carboxylate
  • Pyrazine-2-carboxylic acid
  • Pyrazinecarboxylate
  • Pyrazinecarboxylic acid
  • Pyrazinemonocarboxylate
  • Pyrazinemonocarboxylic acid
  • Pyrazinoate
  • Pyrazinoic acid
  • Pyrazoate
  • Pyrazoic acid
Chemical Formula:C5H4N2O2
Weight:Average: 124.0975
Monoisotopic: 124.027277382
InChI Key:NIPZZXUFJPQHNH-UHFFFAOYSA-N
InChI:InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
CAS number:98-97-5
IUPAC Name:pyrazine-2-carboxylic acid
Traditional IUPAC Name:pyrazinoic acid
SMILES:OC(=O)C1=CN=CC=N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrazine carboxylic acids. These are heterocyclic compounds containing a pyrazine ring substituted by one or more carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazine carboxylic acids
Alternative Parents
Substituents
  • Pyrazine carboxylic acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:225 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility30.5 g/LALOGPS
logP-0.52ALOGPS
logP-0.42ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.08 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.63 m³·mol⁻¹ChemAxon
Polarizability10.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
+ Water Hydrogen ion + Pyrazinic acid + Ammonia
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fc0-9100000000-0d1d9343efa8efa99226View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fc0-9100000000-0d1d9343efa8efa99226View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-9300000000-5d851f8b3e99335027a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9700000000-dc1a24b248b553898896View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9e64f2293e46344d81edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-af86c6152381383e33e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-cafc4cffd9f796c532e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-576cc0731c2413e5e0d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-d888658b0a8673ea88feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-9000000000-eb742c3177bfe29f72e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-90831ac2a79e645518baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-90831ac2a79e645518baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-9000000000-11eb44f98f6f9300db58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-fc721474e0fad99dcba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9100000000-3bc909318a437df6cd91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-c78d399db63d85709c22View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Sun, Z., Zhang, Y. (1999). "Reduced pyrazinamidase activity and the natural resistance of Mycobacterium kansasii to the antituberculosis drug pyrazinamide." Antimicrob Agents Chemother 43:537-542. Pubmed: 10049264
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID71311
HMDB IDHMDB0059734
Pubchem Compound ID1047
Kegg IDC19915
ChemSpider ID1018
Wikipedia IDPyrazinoic_acid
BioCyc IDPYRAZINOIC-ACID
EcoCyc IDPYRAZINOIC-ACID
Ligand ExpoVGL

Enzymes

Protein Details
1. Pyrazinamidase/nicotinamidase
General function:
Involved in catalytic activity
Specific function:
Nicotinamide + H(2)O = nicotinate + NH(3)
Gene Name:
pncA
Uniprot ID:
P21369
Molecular weight:
23362
Reactions
Nicotinamide + H(2)O = nicotinate + NH(3).