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Showing NP-Card for 5-Hydroxypyrazinamide (NP0086831)

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Record Information
Version2.0
Created at2022-05-11 16:32:13 UTC
Updated at2022-05-11 16:32:13 UTC
NP-MRD IDNP0086831
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxypyrazinamide
Description5-Hydroxypyrazinamide belongs to the class of organic compounds known as pyrazinecarboxamides. Pyrazinecarboxamides are compounds containing a pyrazine ring which bears a carboxamide. Pyrazinamide is a generic drug and is available in a wide variety of presentations. 5-Hydroxypyrazinamide is an extremely weak basic (essentially neutral) compound (based on its pKa). It crosses inflamed meninges and is an essential part of the treatment of tuberculous meningitis. M. Tuberculosis has the enzyme pyrazinamidase which is only active at acidic pH. 5-Hydroxypyrazinamide was first documented in 1987 (PMID: 3437007). Pyrazinamidase converts pyrazinamide to the active form, pyrazinoic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086831 (5-Hydroxypyrazinamide)


  Mrv0541 02231219182D          

 10 10  0  0  0  0            999 V2000
   19.3162   -4.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7437   -5.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6018   -3.1859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1728   -5.6609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1728   -4.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6018   -4.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4583   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8872   -4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8872   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4583   -4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
Download

3D MOL for NP0086831 (5-Hydroxypyrazinamide)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.8321    0.4418    0.1509 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8428   -0.5722    0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2064   -1.7611    0.2798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4312   -0.1963   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -1.1562   -0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -0.8278   -0.1474 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335    0.4527   -0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4522    0.7735   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    1.4104   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    1.0784   -0.1417 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259    0.8813   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1962    0.7759    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -2.1939    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6192   -1.5628   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273    2.4564   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0086831 (5-Hydroxypyrazinamide)


  Mrv0541 02231219182D          

 10 10  0  0  0  0            999 V2000
   19.3162   -4.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7437   -5.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6018   -3.1859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1728   -5.6609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1728   -4.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6018   -4.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4583   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8872   -4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8872   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4583   -4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CNC(=O)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)

> <INCHI_KEY>
XENWQEOTDAQROM-UHFFFAOYSA-N

> <FORMULA>
C5H5N3O2

> <MOLECULAR_WEIGHT>
139.1121

> <EXACT_MASS>
139.038176419

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.05002277799318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-oxo-4,5-dihydropyrazine-2-carboxamide

> <ALOGPS_LOGP>
-1.60

> <JCHEM_LOGP>
-1.4731802386666664

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.318802364829853

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.91079243014455

> <JCHEM_PKA_STRONGEST_BASIC>
-1.380686002592657

> <JCHEM_POLAR_SURFACE_AREA>
84.55

> <JCHEM_REFRACTIVITY>
33.7088

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-oxo-4H-pyrazine-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086831 (5-Hydroxypyrazinamide)

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PDB for NP0086831 (5-Hydroxypyrazinamide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      36.057  -8.257   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      29.388 -10.567   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      34.723  -5.947   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      32.056 -10.567   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      32.056  -7.487   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      34.723  -7.487   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.722  -9.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.389  -8.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.389  -9.797   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.722  -8.257   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    7    9                                                       
CONECT    5    8   10                                                       
CONECT    6    1    3    8                                                  
CONECT    7    2    4   10                                                  
CONECT    8    5    6    9                                                  
CONECT    9    4    8                                                       
CONECT   10    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0086831 (5-Hydroxypyrazinamide)
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SMILES for NP0086831 (5-Hydroxypyrazinamide)
NC(=O)C1=CNC(=O)C=N1
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INCHI for NP0086831 (5-Hydroxypyrazinamide)
InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-Carboxamido-5-hydroxypyrazineHMDB
5-Hydroxy-(8ci)-pyrazinecarboxamideHMDB
5-HydroxypyrazinecarboxamideHMDB
5-oxo-4,5-Dihydropyrazine-2-carboximidateHMDB
5-HydroxypyrazinamideMeSH
Chemical FormulaC5H5N3O2
Average Mass139.1121 Da
Monoisotopic Mass139.03818 Da
IUPAC Name5-oxo-4,5-dihydropyrazine-2-carboxamide
Traditional Name5-oxo-4H-pyrazine-2-carboxamide
CAS Registry NumberNot Available
SMILES
NC(=O)C1=CNC(=O)C=N1
InChI Identifier
InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)
InChI KeyXENWQEOTDAQROM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazinecarboxamides. Pyrazinecarboxamides are compounds containing a pyrazine ring which bears a carboxamide.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazines  
Sub ClassPyrazines  
Direct ParentPyrazinecarboxamides  
Alternative Parents
Substituents
  • Pyrazinecarboxamide
    • 

  • 2-heteroaryl carboxamide
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Primary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.71 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001978  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022776  
KNApSAcK IDNot Available
Chemspider ID133812  
KEGG Compound IDC01956  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6413  
PubChem Compound151823  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lacroix C, Poncet P, Laine G, Guyonnaud C, Ray M, Menager S, Lafont O: [Microdetermination of pyrazinamide and its metabolites (pyrazinoic acid, 5-hydroxypyrazinoic acid, 5-hydroxypyrazinamide and pyrazinuric acid) in plasma and urine with liquid chromatography]. J Chromatogr. 1987 Nov 27;422:217-25. [PubMed:3437007  ]