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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:02:04 UTC

Update Date

2019-07-23 07:15:10 UTC

HMDB ID

HMDB0060826

Secondary Accession Numbers

HMDB60826

Metabolite Identification

Common Name

Hydroxynalidixic acid

Description

Hydroxynalidixic acid, also known as hydroxynalidixate, 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. In the technical sense, it is a naphthyridone, not a quinolone: its ring structure is a 1,8-naphthyridine nucleus that contains two nitrogen atoms, unlike quinoline, which has a single nitrogen atom. Hydroxynalidixic acid is a strong basic compound (based on its pKa). Hydroxynalidixic acid is a metabolite of nalidixic acid. Nalidixic acid (tradenames Nevigramon, Neggram, Wintomylon and WIN 18,320) is the first of the synthetic quinolone antibiotics.

Structure

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

HMDB0060826
     RDKit          3D
Hydroxynalidixic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
   -0.1736    2.7390    1.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    1.3377    1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335    0.4010    0.7676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0358    0.1452    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -0.7378   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087   -0.9746   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -1.7900   -1.4830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8386   -0.3104    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.3782   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -2.1979   -2.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.1331   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -1.7778   -1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949   -1.4625   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5606   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.2921   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897    0.6317    0.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074    0.0479    0.2678 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -0.2373    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    3.1768    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    2.6930    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    3.3871    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334    1.0379    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    1.4108    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589    0.6812    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.5875   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576   -2.4628   -2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766   -1.9365   -1.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911    0.0443   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447   -1.2261    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192    0.1568    1.6518 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
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv0541 07041312022D          

 18 19  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3 18  1  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060826

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=CC=C(CO)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O4/c1-2-14-5-9(12(17)18)10(16)8-4-3-7(6-15)13-11(8)14/h3-5,15H,2,6H2,1H3,(H,17,18)

> <INCHI_KEY>
FRJDYPGZHOEEKU-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O4

> <MOLECULAR_WEIGHT>
248.2347

> <EXACT_MASS>
248.079706882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.6519186925131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
0.42082061933333353

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.15824972741628

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.748969587891514

> <JCHEM_PKA_STRONGEST_BASIC>
3.5273774169668717

> <JCHEM_POLAR_SURFACE_AREA>
90.73

> <JCHEM_REFRACTIVITY>
64.5267

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-ethyl-7-(hydroxymethyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060826
     RDKit          3D
Hydroxynalidixic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
   -0.1736    2.7390    1.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    1.3377    1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335    0.4010    0.7676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0358    0.1452    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -0.7378   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087   -0.9746   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -1.7900   -1.4830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8386   -0.3104    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.3782   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -2.1979   -2.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.1331   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -1.7778   -1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949   -1.4625   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5606   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.2921   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897    0.6317    0.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074    0.0479    0.2678 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -0.2373    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    3.1768    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    2.6930    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    3.3871    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334    1.0379    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    1.4108    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589    0.6812    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.5875   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576   -2.4628   -2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766   -1.9365   -1.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911    0.0443   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447   -1.2261    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192    0.1568    1.6518 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
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    3   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060826
HETATM    1  C1  UNL     1      -0.174   2.739   1.168  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.284   1.338   1.781  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.733   0.401   0.768  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.036   0.145   0.548  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.487  -0.738  -0.406  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.909  -0.975  -0.599  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.257  -1.790  -1.483  1.00  0.00           O  
HETATM    8  O2  UNL     1      -4.839  -0.310   0.181  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.532  -1.378  -1.161  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.873  -2.198  -2.050  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.182  -1.133  -0.955  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.784  -1.778  -1.715  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.095  -1.462  -1.431  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.466  -0.561  -0.452  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.917  -0.292  -0.226  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.090   0.632   0.788  1.00  0.00           O  
HETATM   17  N2  UNL     1       1.507   0.048   0.268  1.00  0.00           N  
HETATM   18  C12 UNL     1       0.214  -0.237   0.016  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.185   3.177   1.026  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.325   2.693   0.173  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.393   3.387   1.861  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.633   1.038   2.281  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.103   1.411   2.528  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.759   0.681   1.176  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.160   0.587  -0.153  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.458  -2.463  -2.457  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.877  -1.937  -1.993  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.391   0.044  -1.187  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.445  -1.226   0.053  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.919   0.157   1.652  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   18
CONECT    4    5    5   24
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   25
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   17
CONECT   15   16   28   29
CONECT   16   30
CONECT   17   18   18
END

HMDB0060826
     RDKit          3D
Hydroxynalidixic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
   -0.1736    2.7390    1.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    1.3377    1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335    0.4010    0.7676 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0358    0.1452    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -0.7378   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087   -0.9746   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -1.7900   -1.4830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8386   -0.3104    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.3782   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8729   -2.1979   -2.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.1331   -0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -1.7778   -1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949   -1.4625   -1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.5606   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.2921   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897    0.6317    0.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074    0.0479    0.2678 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -0.2373    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    3.1768    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    2.6930    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    3.3871    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334    1.0379    2.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    1.4108    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7589    0.6812    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.5875   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576   -2.4628   -2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766   -1.9365   -1.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911    0.0443   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447   -1.2261    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192    0.1568    1.6518 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
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Hydroxynalidixate	Generator
7-Hydroxymethylnalidixic acid	HMDB
7-(Hydroxymethyl)nalidixic acid	HMDB
7-Hydroxynalidixic acid, monosodium salt	HMDB
1-Ethyl-7-(hydroxymethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate	Generator

Chemical Formula

C₁₂H₁₂N₂O₄

Average Molecular Weight

248.2347

Monoisotopic Molecular Weight

248.079706882

IUPAC Name

1-ethyl-7-(hydroxymethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Traditional Name

1-ethyl-7-(hydroxymethyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid

CAS Registry Number

3759-18-0

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC=C(CO)N=C12

InChI Identifier

InChI=1S/C12H12N2O4/c1-2-14-5-9(12(17)18)10(16)8-4-3-7(6-15)13-11(8)14/h3-5,15H,2,6H2,1H3,(H,17,18)

InChI Key

FRJDYPGZHOEEKU-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
Pyridine
Vinylogous amide
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060826)

Organ

Kidney (HMDB: HMDB0060826)
Liver (HMDB: HMDB0060826)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060826)

Cellular substructure

Cytoplasm (HMDB: HMDB0060826)

Source

Endogenous

Endogenous (HMDB: HMDB0060826)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.14 g/L	ALOGPS
logP	0.27	ALOGPS
logP	0.42	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	5.75	ChemAxon
pKa (Strongest Basic)	3.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.53 m³·mol⁻¹	ChemAxon
Polarizability	24.65 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]+	156.951	31661259
DarkChem	[M-H]-	155.868	31661259
DeepCCS	[M-2H]-	189.649	30932474
DeepCCS	[M+Na]+	165.195	30932474
AllCCS	[M+H]+	154.4	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	158.0	32859911
AllCCS	[M+Na]+	159.0	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	156.6	32859911
AllCCS	[M+HCOO]-	156.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.56 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5335 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1795.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	337.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	483.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	772.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	344.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1476.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	179.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	175.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxynalidixic acid	CCN1C=C(C(O)=O)C(=O)C2=CC=C(CO)N=C12	2947.6	Standard polar	33892256
Hydroxynalidixic acid	CCN1C=C(C(O)=O)C(=O)C2=CC=C(CO)N=C12	1881.1	Standard non polar	33892256
Hydroxynalidixic acid	CCN1C=C(C(O)=O)C(=O)C2=CC=C(CO)N=C12	2611.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxynalidixic acid,1TMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC=C(CO)N=C21	2372.2	Semi standard non polar	33892256
Hydroxynalidixic acid,1TMS,isomer #2	CCN1C=C(C(=O)O)C(=O)C2=CC=C(CO[Si](C)(C)C)N=C21	2410.4	Semi standard non polar	33892256
Hydroxynalidixic acid,2TMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC=C(CO[Si](C)(C)C)N=C21	2378.8	Semi standard non polar	33892256
Hydroxynalidixic acid,1TBDMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC=C(CO)N=C21	2624.4	Semi standard non polar	33892256
Hydroxynalidixic acid,1TBDMS,isomer #2	CCN1C=C(C(=O)O)C(=O)C2=CC=C(CO[Si](C)(C)C(C)(C)C)N=C21	2672.5	Semi standard non polar	33892256
Hydroxynalidixic acid,2TBDMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC=C(CO[Si](C)(C)C(C)(C)C)N=C21	2848.0	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 - Hydroxynalidixic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-0190000000-28f2f7f2988c55589152	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxynalidixic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0fi0-4019000000-a10444a5136d59af29a7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxynalidixic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 10V, Positive-QTOF	splash10-001j-0090000000-365c68eb53750e3a3946	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 20V, Positive-QTOF	splash10-01qi-0390000000-78daaca12050e9e8321c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 40V, Positive-QTOF	splash10-000i-0930000000-b93c37cc37c43bf9d863	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 10V, Negative-QTOF	splash10-0udj-0290000000-8eeeb403c32c462eee53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 20V, Negative-QTOF	splash10-0fmr-0920000000-b2124cd08c9905812582	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 40V, Negative-QTOF	splash10-00fr-0900000000-122cc11f732b6c39a720	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 10V, Positive-QTOF	splash10-0002-0090000000-c5fb311b8234402b13ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 20V, Positive-QTOF	splash10-001i-0090000000-0bbc16def421dfe3548d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 40V, Positive-QTOF	splash10-0udi-0590000000-24f198534a5ff724bb79	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 10V, Negative-QTOF	splash10-0ftb-0490000000-9b486fbafeb0162a41d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 20V, Negative-QTOF	splash10-00di-0900000000-bf0d9092c5b01be34aa2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxynalidixic acid 40V, Negative-QTOF	splash10-00di-0900000000-b7020ed63c54f3151501	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160716

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Not Available

Showing metabocard for Hydroxynalidixic acid (HMDB0060826)

MOL for HMDB0060826 (Hydroxynalidixic acid)

3D MOL for HMDB0060826 (Hydroxynalidixic acid)

3D SDF for HMDB0060826 (Hydroxynalidixic acid)

3D-SDF for HMDB0060826 (Hydroxynalidixic acid)

PDB for HMDB0060826 (Hydroxynalidixic acid)

3D PDB for HMDB0060826 (Hydroxynalidixic acid)

SMILES for HMDB0060826 (Hydroxynalidixic acid)

INCHI for HMDB0060826 (Hydroxynalidixic acid)

Structure for HMDB0060826 (Hydroxynalidixic acid)

3D Structure for HMDB0060826 (Hydroxynalidixic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra