Pyrazin-2-carboxylic acid (CHEM022476)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:36:28 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022476
Identification
Common NamePyrazin-2-carboxylic acid
ClassSmall Molecule
DescriptionThe parent compound of the class of pyrazinecarboxylic acids, that is pyrazine bearing a single carboxy substituent. The active metabolite of the antitubercular drug pyrazinamide.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-CarboxypyrazineChEBI
2-Pyrazinecarboxylic acidChEBI
Paradiazinecarboxylic acidChEBI
Pyrazinecarboxylic acidChEBI
Pyrazinemonocarboxylic acidChEBI
Pyrazinic acidChEBI
Pyrazinoic acidChEBI
2-PyrazinecarboxylateGenerator
ParadiazinecarboxylateGenerator
PyrazinecarboxylateGenerator
PyrazinemonocarboxylateGenerator
PyrazinateGenerator
PyrazinoateGenerator
Pyrazin-2-carboxylateGenerator
Pyrazine-2-carboxylic acidMeSH
Pyrazine-2-carboxylateGenerator
Chemical FormulaC5H4N2O2
Average Molecular Mass124.098 g/mol
Monoisotopic Mass124.027 g/mol
CAS Registry NumberNot Available
IUPAC Namepyrazine-2-carboxylic acid
Traditional Namepyrazinoic acid
SMILESOC(=O)C1=CN=CC=N1
InChI IdentifierInChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
InChI KeyNIPZZXUFJPQHNH-UHFFFAOYSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fc0-9100000000-0d1d9343efa8efa99226Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fc0-9100000000-0d1d9343efa8efa99226Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-9300000000-5d851f8b3e99335027a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9700000000-dc1a24b248b553898896Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9e64f2293e46344d81edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-af86c6152381383e33e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9000000000-cafc4cffd9f796c532e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-576cc0731c2413e5e0d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-d888658b0a8673ea88feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-9000000000-eb742c3177bfe29f72e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-90831ac2a79e645518baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-90831ac2a79e645518baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-9000000000-11eb44f98f6f9300db58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-fc721474e0fad99dcba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9100000000-3bc909318a437df6cd91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-c78d399db63d85709c22Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0059734
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDPYRAZINOIC-ACID
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyrazinoic_acid
Chemspider ID1018
ChEBI ID71311
PubChem Compound ID1047
Kegg Compound IDC19915
YMDB IDNot Available
ECMDB IDECMDB02069
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19298694
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19963078
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20099263
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20382083
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20429806
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20879713
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21283666
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21775138
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21835980
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21876062
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22004792
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22074423
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22236853
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22372927
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22613684
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23101013
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
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20. Nakanishi T, Ohya K, Shimada S, Anzai N, Tamai I: Functional cooperation of URAT1 (SLC22A12) and URATv1 (SLC2A9) in renal reabsorption of urate. Nephrol Dial Transplant. 2013 Mar;28(3):603-11. doi: 10.1093/ndt/gfs574. Epub 2013 Jan 4.
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22. Vishweshwar P, Nangia A, Lynch VM: Recurrence of carboxylic acid-pyridine supramolecular synthon in the crystal structures of some pyrazinecarboxylic acids. J Org Chem. 2002 Jan 25;67(2):556-65.
23. Ma C, Han Y, Zhang R, Wang D: Self-assembly of diorganotin(IV) moieties and 2-pyrazinecarboxylic acid: syntheses, characterizations and crystal structures of monomeric, polymeric or trinuclear macrocyclic compounds. Dalton Trans. 2004 Jun 21;(12):1832-40. Epub 2004 May 13.
24. Dolezal M, Kesetovic D, Zitko J: Antimycobacterial evaluation of pyrazinoic acid reversible derivatives. Curr Pharm Des. 2011;17(32):3506-14.
25. Sato M, Wakayama T, Mamada H, Shirasaka Y, Nakanishi T, Tamai I: Identification and functional characterization of uric acid transporter Urat1 (Slc22a12) in rats. Biochim Biophys Acta. 2011 Jun;1808(6):1441-7. doi: 10.1016/j.bbamem.2010.11.002. Epub 2010 Nov 11.
26. Holzer W, Eller GA, Datterl B, Habicht D: Derivatives of pyrazinecarboxylic acid: 1H, 13C and 15N NMR spectroscopic investigations. Magn Reson Chem. 2009 Jul;47(7):617-24. doi: 10.1002/mrc.2437.
27. Nayak S, Harms K, Dehnen S: New three-dimensional metal-organic framework with heterometallic [Fe-Ag] building units: synthesis, crystal structure, and functional studies. Inorg Chem. 2011 Apr 4;50(7):2714-6. doi: 10.1021/ic1019636. Epub 2011 Mar 1.
28. Tanase S, Marques Gallego P, Bouwman E, Long GJ, Rebbouh L, Grandjean F, de Gelder R, Mutikainen I, Turpeinen U, Reedijk J: Versatility in the binding of 2-pyrazinecarboxylate with iron. Synthesis, structure and magnetic properties of iron(II) and iron(III) complexes. Dalton Trans. 2006 Apr 7;(13):1675-84. Epub 2005 Dec 15.
29. Dolezal M, Palek L, Vinsova J, Buchta V, Jampilek J, Kralova K: Substituted pyrazinecarboxamides: synthesis and biological evaluation. Molecules. 2006 Mar 29;11(4):242-56.
30. Sato M, Mamada H, Anzai N, Shirasaka Y, Nakanishi T, Tamai I: Renal secretion of uric acid by organic anion transporter 2 (OAT2/SLC22A7) in human. Biol Pharm Bull. 2010;33(3):498-503.
31. Servusova B, Eibinova D, Dolezal M, Kubicek V, Paterova P, Pesko M, Kralova K: Substituted N-benzylpyrazine-2-carboxamides: synthesis and biological evaluation. Molecules. 2012 Nov 6;17(11):13183-98. doi: 10.3390/molecules171113183.
32. Cuevas A, Kremer C, Hummert M, Schumann H, Lloret F, Julve M, Faus J: Magnetic properties and molecular structures of binuclear (2-pyrazinecarboxylate)-bridged complexes containing Re(IV) and M(II) (M = Co, Ni). Dalton Trans. 2007 Jan 21;(3):342-50. Epub 2006 Nov 21.
33. Dolezal M, Zitko J, Osicka Z, Kunes J, Vejsova M, Buchta V, Dohnal J, Jampilek J, Kralova K: Synthesis, antimycobacterial, antifungal and photosynthesis-inhibiting activity of chlorinated N-phenylpyrazine-2-carboxamides. Molecules. 2010 Nov 26;15(12):8567-81. doi: 10.3390/molecules15128567.
34. Knope KE, Kimura H, Yasaka Y, Nakahara M, Andrews MB, Cahill CL: Investigation of in situ oxalate formation from 2,3-pyrazinedicarboxylate under hydrothermal conditions using nuclear magnetic resonance spectroscopy. Inorg Chem. 2012 Mar 19;51(6):3883-90. doi: 10.1021/ic3000944. Epub 2012 Feb 24.