Np mrd loader

Showing NP-Card for Isonicotinic acid (NP0002621)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2020-11-23 18:25:27 UTC
Updated at2024-09-03 04:22:20 UTC
NP-MRD IDNP0002621
Natural Product DOIhttps://doi.org/10.57994/2824
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsonicotinic acid
Provided ByBMRBBMRB logo
DescriptionIsonicotinic acid, also known as 4-carboxypyridine or gamma-picolinic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Isonicotinic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Isonicotinic acid is found in Aloe africana, Arabidopsis thaliana and Chlamydomonas reinhardtii. Isonicotinic acid was first documented in 1953 (PMID: 13115353). Based on a literature review a small amount of articles have been published on Isonicotinic acid (PMID: 22537922) (PMID: 23832340) (PMID: 23929452).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002621 (Isonicotinic acid)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.2776   -1.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -0.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    0.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475   -0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    1.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    0.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1237   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -1.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858    0.3208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885    2.3723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0457    2.9970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.0852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1936   -2.7100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
M  END
Download

3D MOL for NP0002621 (Isonicotinic acid)

NP0002621
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.3247   -1.2217   -0.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -0.3001   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192    0.5640    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963   -0.0827   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581    0.9293    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.1069    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324    0.2357    0.0793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529   -0.7835   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.9455   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    0.2255    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968    1.6073    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9670    1.9080    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -1.4783   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.7647   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
M  END
Download

3D SDF for NP0002621 (Isonicotinic acid)


     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.2776   -1.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -0.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    0.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475   -0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    1.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    0.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1237   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -1.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858    0.3208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885    2.3723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0457    2.9970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.0852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1936   -2.7100    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
M  END
> <DATABASE_ID>
NP0002621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)

> <INCHI_KEY>
TWBYWOBDOCUKOW-UHFFFAOYSA-N

> <FORMULA>
C6H5NO2

> <MOLECULAR_WEIGHT>
123.1094

> <EXACT_MASS>
123.032028409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.286762629868125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-4-carboxylic acid

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.15446222091268916

> <ALOGPS_LOGS>
-0.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.732221977879659

> <JCHEM_PKA_STRONGEST_BASIC>
2.3463604455988625

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
31.157299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isonicotinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002621 (Isonicotinic acid)

NP0002621
     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.3247   -1.2217   -0.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -0.3001   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192    0.5640    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963   -0.0827   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581    0.9293    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.1069    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3324    0.2357    0.0793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8529   -0.7835   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.9455   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    0.2255    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968    1.6073    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9670    1.9080    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -1.4783   -1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1275   -1.7647   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
M  END
Download

PDB for NP0002621 (Isonicotinic acid)

HEADER    PROTEIN                                 11-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAR-19         0                                  
HETATM    1  C   UNK     0      47.691 -31.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      47.687 -29.653   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      46.367 -31.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      49.029 -31.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.354 -28.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      44.957 -31.208   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      49.034 -33.496   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      50.359 -31.184   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      45.021 -29.670   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0002621 (Isonicotinic acid)

COMPND    NP0002621
HETATM    1  O1  UNL     1       2.325  -1.222  -0.955  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.822  -0.300  -0.285  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.719   0.564   0.353  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.396  -0.083  -0.135  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.158   0.929   0.601  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.531   1.107   0.721  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.332   0.236   0.079  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.853  -0.784  -0.662  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.469  -0.946  -0.772  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.184   0.226   1.194  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.497   1.607   1.100  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.967   1.908   1.304  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.506  -1.478  -1.175  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.127  -1.765  -1.368  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5    9
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   14
END
Download

SMILES for NP0002621 (Isonicotinic acid)

OC(=O)C1=CC=NC=C1
Download

INCHI for NP0002621 (Isonicotinic acid)

InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
Download
View in JSmol
Synonyms
ValueSource
4-CarboxypyridineChEBI
4-Pyridinecarboxylic acidChEBI
gamma-Picolinic acidChEBI
gamma-Pyridinecarboxylic acidChEBI
p-Pyridinecarboxylic acidChEBI
4-PyridinecarboxylateGenerator
g-PicolinateGenerator
g-Picolinic acidGenerator
gamma-PicolinateGenerator
Γ-picolinateGenerator
Γ-picolinic acidGenerator
g-PyridinecarboxylateGenerator
g-Pyridinecarboxylic acidGenerator
gamma-PyridinecarboxylateGenerator
Γ-pyridinecarboxylateGenerator
Γ-pyridinecarboxylic acidGenerator
p-PyridinecarboxylateGenerator
IsonicotinateGenerator
Acid, isonicotinicHMDB
Acids, isonicotinicHMDB
Isonicotinic acidsHMDB
Chemical FormulaC6H5NO2
Average Mass123.1094 Da
Monoisotopic Mass123.03203 Da
IUPAC Namepyridine-4-carboxylic acid
Traditional Nameisonicotinic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=NC=C1
InChI Identifier
InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
InChI KeyTWBYWOBDOCUKOW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Arabidopsis thalianaLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Kandelia candelKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.28ALOGPS
logP0.15ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)2.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060665
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00009101
Chemspider ID5709
KEGG Compound IDC07446
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsonicotinic_Acid
METLIN IDNot Available
PubChem Compound5922
PDB IDNot Available
ChEBI ID6032
Good Scents IDNot Available
References
General References
  1. CUTHBERTSON WF, IRELAND DM, WOLFF W: Detection and identification of some metabolites of isonicotinic acid hydrazide (isoniazid) in human urine. Biochem J. 1953 Nov;55(4):669-71. doi: 10.1042/bj0550669. [PubMed:13115353 ]
  2. Sharma NN, Sharma M, Bhalla TC: Nocardia globerula NHB-2 nitrilase catalysed biotransformation of 4-cyanopyridine to isonicotinic acid. AMB Express. 2012 Apr 26;2(1):25. doi: 10.1186/2191-0855-2-25. [PubMed:22537922 ]
  3. Ida C, Ogata S: Changes in NAD content induced by nicotinic acid-related compounds in K562 cells during differentiation. Biosci Biotechnol Biochem. 2013;77(7):1583-5. doi: 10.1271/bbb.130131. Epub 2013 Jul 7. [PubMed:23832340 ]
  4. Hong SP, Lusiak BD, Burback BL, Johnson JD: Evaluations of in vitro metabolism, drug-drug interactions mediated by reversible and time-dependent inhibition of CYPs, and plasma protein binding of MMB4 DMS. Int J Toxicol. 2013 Jul-Aug;32(4 Suppl):75S-87S. doi: 10.1177/1091581813487226. [PubMed:23929452 ]