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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014917

Secondary Accession Numbers

HMDB14917

Metabolite Identification

Common Name

Nalidixic Acid

Description

Nalidixic Acid is only found in individuals that have used or taken this drug. It is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014917
     RDKit          3D
Nalidixic Acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.8307    2.9850   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.2550    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.0908    0.6255 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    1.2216    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    0.0979    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.2094    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.3101    0.8452 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180   -0.9094    0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222   -1.1016    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -2.1252    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.2274    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1388   -2.4420   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -2.5250   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -1.3835    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7475   -1.4712   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.2305    0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3174   -0.0781    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    3.6654   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069    3.6495   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    2.3026   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    1.9353    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.9661    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.1398    0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.0138   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -3.3049   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294   -3.4663   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075   -1.3085   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.7548    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904   -2.4864    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  3  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  8 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

779
  Mrv0541 02231215002D          

 17 18  0  0  0  0            999 V2000
    4.2364    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885   -0.6474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    0.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -0.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 16  1  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 12 15  2  0  0  0  0
 13 15  1  0  0  0  0
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014917

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

> <INCHI_KEY>
MHWLWQUZZRMNGJ-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O3

> <MOLECULAR_WEIGHT>
232.2353

> <EXACT_MASS>
232.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.649783745099587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.0082525712681194

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.950252968990619

> <JCHEM_PKA_STRONGEST_BASIC>
4.678220137258441

> <JCHEM_POLAR_SURFACE_AREA>
70.5

> <JCHEM_REFRACTIVITY>
62.8245

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nalidixic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014917
     RDKit          3D
Nalidixic Acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.8307    2.9850   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.2550    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.0908    0.6255 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    1.2216    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    0.0979    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.2094    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.3101    0.8452 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180   -0.9094    0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222   -1.1016    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -2.1252    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.2274    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1388   -2.4420   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -2.5250   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -1.3835    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7475   -1.4712   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.2305    0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3174   -0.0781    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    3.6654   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069    3.6495   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    2.3026   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    1.9353    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.9661    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.1398    0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.0138   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -3.3049   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294   -3.4663   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075   -1.3085   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.7548    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904   -2.4864    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  3  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  8 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 779                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.908   3.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   1.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241   3.465   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.908  -1.155   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.619  -1.208   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.242  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.619   1.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.014  -0.417   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.014   1.187   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.241   1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.344  -1.192   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4    6    8    9                                                  
CONECT    5    6   13                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6   11   12                                                  
CONECT    8    4   14                                                       
CONECT    9    4   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    1    7   10                                                  
CONECT   12    7   15                                                       
CONECT   13    5   15   17                                                  
CONECT   14    8                                                            
CONECT   15   12   13                                                       
CONECT   16    2    3   10                                                  
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014917
HETATM    1  C1  UNL     1      -0.831   2.985  -0.472  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.560   2.255   0.820  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.274   1.091   0.626  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.588   1.222   0.708  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.404   0.098   0.521  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.842   0.209   0.605  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.375   1.310   0.845  1.00  0.00           O  
HETATM    8  O2  UNL     1       4.618  -0.909   0.417  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.822  -1.102   0.259  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.565  -2.125   0.088  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.451  -1.227   0.175  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.139  -2.442  -0.091  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.509  -2.525  -0.166  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.265  -1.383   0.027  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.748  -1.471  -0.054  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.650  -0.231   0.282  1.00  0.00           N  
HETATM   17  C12 UNL     1      -0.317  -0.078   0.369  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.007   3.665  -0.759  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.707   3.650  -0.288  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.123   2.303  -1.295  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.526   1.935   1.230  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.063   2.966   1.511  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.110   2.140   0.912  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.285  -1.014  -0.345  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.482  -3.305  -0.235  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.029  -3.466  -0.375  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.007  -1.309  -1.139  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.259  -0.755   0.593  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.090  -2.486   0.227  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   17
CONECT    4    5    5   23
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   24
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   16
CONECT   15   27   28   29
CONECT   16   17   17
END

HMDB0014917
     RDKit          3D
Nalidixic Acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.8307    2.9850   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    2.2550    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.0908    0.6255 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    1.2216    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    0.0979    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.2094    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.3101    0.8452 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180   -0.9094    0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222   -1.1016    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -2.1252    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.2274    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1388   -2.4420   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -2.5250   -0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -1.3835    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7475   -1.4712   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.2305    0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3174   -0.0781    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    3.6654   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069    3.6495   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    2.3026   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    1.9353    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.9661    1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.1398    0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.0138   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -3.3049   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294   -3.4663   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075   -1.3085   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.7548    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904   -2.4864    0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  3  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  8 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure	ChEBI
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid	ChEBI
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid	ChEBI
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one	ChEBI
Acide nalidixique	ChEBI
Acido nalidixico	ChEBI
Acidum nalidixicum	ChEBI
NA	Kegg
NegGram	Kegg
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate	Generator
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylate	Generator
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate	Generator
Nalidixate	Generator
Acid, nalidixic	HMDB
Nevigramon	HMDB
Sodium, nalidixate	HMDB
Nalidixate sodium	HMDB
Nalidixin	HMDB
Sodium nalidixic acid, anhydrous	HMDB
Anhydrous, nalidixate sodium	HMDB
Nalidixate sodium anhydrous	HMDB
Sodium anhydrous, nalidixate	HMDB
Sodium nalidixic acid, monohydrate	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃

Average Molecular Weight

232.2353

Monoisotopic Molecular Weight

232.08479226

IUPAC Name

1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Traditional Name

nalidixic acid

CAS Registry Number

389-08-2

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

InChI Identifier

InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridine carboxylic acids and derivatives

Alternative Parents

Substituents

Naphthyridine carboxylic acid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Methylpyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:100147 )
1,8-naphthyridine derivative (CHEBI:100147 )
quinolone antibiotic (CHEBI:100147 )
4-Quinolones (C05079 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Blood (HMDB: HMDB0014917)
Urine (HMDB: HMDB0014917)

Cellular substructure

Cytoplasm (HMDB: HMDB0014917)

Cytoplasm (HMDB: HMDB0014917)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Anti-infective (HMDB: HMDB0014917)

Enzyme inhibitor (HMDB: HMDB0014917)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.3 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	145.251	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001033

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.3 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.01	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	5.95	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.82 m³·mol⁻¹	ChemAxon
Polarizability	23.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.938	31661259
DarkChem	[M-H]-	153.628	31661259
DeepCCS	[M+H]+	154.007	30932474
DeepCCS	[M-H]-	151.611	30932474
DeepCCS	[M-2H]-	184.593	30932474
DeepCCS	[M+Na]+	160.061	30932474
AllCCS	[M+H]+	150.2	32859911
AllCCS	[M+H-H2O]+	146.1	32859911
AllCCS	[M+NH4]+	154.0	32859911
AllCCS	[M+Na]+	155.0	32859911
AllCCS	[M-H]-	153.8	32859911
AllCCS	[M+Na-2H]-	153.8	32859911
AllCCS	[M+HCOO]-	153.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nalidixic Acid	CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2	2704.4	Standard polar	33892256
Nalidixic Acid	CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2	1856.2	Standard non polar	33892256
Nalidixic Acid	CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2	2465.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nalidixic Acid,1TMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC=C(C)N=C21	2223.6	Semi standard non polar	33892256
Nalidixic Acid,1TBDMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC=C(C)N=C21	2451.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fri-1790000000-92a3a10bfaccb41342fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalidixic Acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-8290000000-87bbcaf099e222302f02	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-qTof , Positive-QTOF	splash10-014r-0590000000-0071689427e5460e9504	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-qTof , Positive-QTOF	splash10-053i-2920000000-a81650e261062799ba89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOF	splash10-001i-0090000000-b3f65ce918413bce9fa8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOF	splash10-014i-0090000000-0ff01a82dbce74faefc6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOF	splash10-014r-0790000000-46caea0fd85329797145	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOF	splash10-000i-0900000000-3572ae3957b712815a4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOF	splash10-0zgr-0900000000-a89fdf787950fb2d88c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid LC-ESI-IT , positive-QTOF	splash10-0a4i-0290000000-db7256d80ff333bc00bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid , positive-QTOF	splash10-015i-0590000000-938c78d9d632c54cdffe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid , positive-QTOF	splash10-014r-0590000000-0071689427e5460e9504	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid , positive-QTOF	splash10-053i-2920000000-a81650e261062799ba89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 45V, Positive-QTOF	splash10-001i-0190000000-9f01c18c495b23232800	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 60V, Positive-QTOF	splash10-0a4i-0490000000-2fbf36cc9f6f88d4cd65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 30V, Positive-QTOF	splash10-001i-0090000000-1d2b6985d9b92bbb9824	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 15V, Positive-QTOF	splash10-001i-0090000000-3364d0d3d6ede5d5b1a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 75V, Positive-QTOF	splash10-0a4i-0950000000-f2b2776dbe2dc1e2e9be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 90V, Positive-QTOF	splash10-0pc0-0910000000-560515fc3b04b07a51e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 30V, Negative-QTOF	splash10-001r-3390000000-17e93f93f9a5f2cf26a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nalidixic Acid 15V, Negative-QTOF	splash10-001i-1190000000-a192d15d35dfb6d306d7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 10V, Positive-QTOF	splash10-001i-0190000000-fef5a9adccc5a0a5ec05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 20V, Positive-QTOF	splash10-00li-0890000000-c72282680d1ade35245c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 40V, Positive-QTOF	splash10-00ds-1900000000-4659dda7bb11b31ca0ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 10V, Negative-QTOF	splash10-0019-0960000000-660f38f48e34b738382d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 20V, Negative-QTOF	splash10-0a4r-0900000000-76a76cfafed1c3238f42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nalidixic Acid 40V, Negative-QTOF	splash10-0a4i-1900000000-1b71f0a68ff3448016e3	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00779	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00779	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00779

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020181

KNApSAcK ID

Not Available

Chemspider ID

4268

KEGG Compound ID

C05079

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nalidixic_Acid

METLIN ID

Not Available

PubChem Compound

4421

PDB ID

Not Available

ChEBI ID

100147

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Tryptophan 2,3-dioxygenase

General function:: Involved in tryptophan 2,3-dioxygenase activity
Specific function:: Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name:: TDO2
Uniprot ID:: P48775
Molecular weight:: 47871.215

References

Sanzey B: Modulation of gene expression by drugs affecting deoxyribonucleic acid gyrase. J Bacteriol. 1979 Apr;138(1):40-7. [PubMed:108253 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]

Showing metabocard for Nalidixic Acid (HMDB0014917)

MOL for HMDB0014917 (Nalidixic Acid)

3D MOL for HMDB0014917 (Nalidixic Acid)

3D SDF for HMDB0014917 (Nalidixic Acid)

3D-SDF for HMDB0014917 (Nalidixic Acid)

PDB for HMDB0014917 (Nalidixic Acid)

3D PDB for HMDB0014917 (Nalidixic Acid)

SMILES for HMDB0014917 (Nalidixic Acid)

INCHI for HMDB0014917 (Nalidixic Acid)

Structure for HMDB0014917 (Nalidixic Acid)

3D Structure for HMDB0014917 (Nalidixic Acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References