Pyrazinecarboxamide (YMDB00976)

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Identification

YMDB ID

YMDB00976

Name

Pyrazinecarboxamide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Pyrazinamide, also known as pirazimida or PZA, belongs to the class of organic compounds known as pyrazines. Pyrazines 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 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-Carbamylpyrazine
2-Pyrazinecarboxamide
Aldinamid
Aldinamide
Eprazin
Farmizina
Novamid
Pirazimida
Pirazinamid
Pyrafat
Pyrazinamdie
Pyrazinamide
pyrazine carboxamide
Pyrazine carboxylamide
PYRAZINE-2-CARBOXAMIDE
Pyrazineamide
Pyrazinecarboxamide
Pyrazinecarboxylic acid amide
Pyrazinoic acid amide
PZA
Tebrazid
Unipyranamide
Zinamide
Pyrazinamida
Pyrazinamidum
Pyrazinoate amide
Tisamid

CAS number

98-96-4

Weight

Average: 123.1127
Monoisotopic: 123.043261797

InChI Key

IPEHBUMCGVEMRF-UHFFFAOYSA-N

InChI

InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)

IUPAC Name

pyrazine-2-carboxamide

Traditional IUPAC Name

pyrazinamide

Chemical Formula

C₅H₅N₃O

SMILES

NC(=O)C1=NC=CN=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrazines. Pyrazines 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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines (CHEBI:45285 )
monocarboxylic acid amide (CHEBI:45285 )
a carboxamide (PYRAZINAMIDE )

Physical Properties

State

Solid

Charge

Melting point

192 °C

Experimental Properties

Property	Value	Reference
Water Solubility	15 mg/mL at 25 oC [MERCK INDEX (1996)]	PhysProp
LogP	-0.60 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	93.7 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-1.2	ChemAxon
logS	-0.12	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.87 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.45 m³·mol⁻¹	ChemAxon
Polarizability	11.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-9400000000-d5dcdea97c58506b64c2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-1900000000-d29284f74cafc89d62ad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9200000000-f1f9853e24fa676ffa99	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001j-9000000000-7be5ab1fa895dc272521	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000t-9000000000-9c4235602fdfd2d2cdeb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-3009000000-ab4d0160c375af6d52ee	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-37eb3e998464288cbbf9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ai-6900000000-45087b42af5c75ada6ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9200000000-50b3f942e52f5925e0db	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2900000000-f94eb5a23c26a4c9a87e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9800000000-ea7b102e875300f2f70b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cd37c3a7e9f314fea54e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1900000000-fc4d9556025fecfd087f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-9000000000-7864651f3a9fb2904c12	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-b69c290737e737bd3aeb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9300000000-f01174d71938c1ae0455	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-9200000000-8c30490f9e058d5b04c8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5d4ecfef90d7597892e8	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Hu, G., Taylor, A. B., McAlister-Henn, L., Hart, P. J. (2007). "Crystal structure of the yeast nicotinamidase Pnc1p." Arch Biochem Biophys 461:66-75.17382284

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	45285
HMDB ID	HMDB0014483
Pubchem Compound ID	1046
Kegg ID	C01956
ChemSpider ID	1017
FOODB ID	Not Available
Wikipedia	Pyrazinamide
BioCyc ID	Not Available

Enzymes

Protein Details

1. Nicotinamidase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the deamidation of nicotinamide, an early step in the NAD(+) salvage pathway. Positively regulates SIR2-mediated silencing and longevity by preventing the accumulation of intracellular nicotinamide, an inhibitor of SIR2, during times of stress. Acts also on nicotinyl hydroxamate
Gene Name:: PNC1
Uniprot ID:: P53184
Molecular weight:: 24993.19922

Reactions

Nicotinamide + H(2)O → nicotinate + NH(3).

Structure for #<Compound:0xa9b34238>

Enzymes

Reactions