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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014965

Secondary Accession Numbers

HMDB14965

Metabolite Identification

Common Name

Cinoxacin

Description

Cinoxacin, also known as CINX or cinobac, belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring. Within the most recent package insert (circa 1999) Cinobac is listed as being contraindicated in patients with a history of hypersensitivity to cinoxacin or other quinolones. Cinoxacin is a drug which is used for the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: escherichia coli, proteus mirabilis, proteus vulgaris, klebsiella species (including k. pneumoniae), and enterobacter species. There are reports that cinoxacin had also been used to treat initial and recurrent urinary tract infections and bacterial prostatitis in dogs. Cinoxacin is an extremely weak basic (essentially neutral) compound (based on its pKa). Relative to nalidixic acid, cinoxacin was found to have a slightly greater inhibitory and bactericidal activity.

Structure

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

HMDB0014965
     RDKit          3D
Cinoxacin
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.9278   -2.5807    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.6116   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -0.3251   -0.4821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623    0.6015   -0.2256 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493    1.8354    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    2.8010    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    3.9595    0.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2261    2.5723    0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144    2.1207    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1812    3.2661    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.1697    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078    1.4191    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765    0.4657   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996   -0.7885   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395   -1.0414   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -0.0859   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5470   -1.5656   -0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.9392    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664    0.4221    0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.6997    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -3.5515   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.1889    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -2.0544   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -1.4787   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7999    2.2339    1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.3961    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653   -2.0089   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261   -1.2394    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -1.1037   -0.3181 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  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 16  3  1  0
 16 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  8 25  1  0
 12 26  1  0
 15 27  1  0
 18 28  1  0
 18 29  1  0
M  END

827
  Mrv0541 02231215022D          

 19 21  0  0  0  0            999 V2000
    7.2157   -0.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2157    0.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    1.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    0.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8112    1.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685   -0.6433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210   -0.2193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060    0.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205   -0.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350    0.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205    1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    1.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6972    0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5684   -1.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081    1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 17  1  0  0  0  0
  2 12  1  0  0  0  0
  2 17  1  0  0  0  0
  3 15  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  7 16  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 13  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014965

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

> <INCHI_KEY>
VDUWPHTZYNWKRN-UHFFFAOYSA-N

> <FORMULA>
C12H10N2O5

> <MOLECULAR_WEIGHT>
262.2182

> <EXACT_MASS>
262.05897144

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
24.72192384473809

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.716116835333333

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.930532150363794

> <JCHEM_PKA_STRONGEST_BASIC>
-4.626802411018023

> <JCHEM_POLAR_SURFACE_AREA>
88.43

> <JCHEM_REFRACTIVITY>
73.6022

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinoxacin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014965
     RDKit          3D
Cinoxacin
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.9278   -2.5807    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.6116   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -0.3251   -0.4821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623    0.6015   -0.2256 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493    1.8354    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    2.8010    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    3.9595    0.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2261    2.5723    0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144    2.1207    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1812    3.2661    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.1697    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078    1.4191    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765    0.4657   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996   -0.7885   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395   -1.0414   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -0.0859   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5470   -1.5656   -0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.9392    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664    0.4221    0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.6997    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -3.5515   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.1889    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -2.0544   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -1.4787   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7999    2.2339    1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.3961    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653   -2.0089   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261   -1.2394    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -1.1037   -0.3181 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  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 16  3  1  0
 16 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  8 25  1  0
 12 26  1  0
 15 27  1  0
 18 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 827                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.469  -0.847   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.469   1.632   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.986   3.526   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.905   1.205   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.248   3.510   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.968  -1.201   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.573  -0.409   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.345  -0.377   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.345   1.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.012  -0.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.678  -1.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.012   1.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.678   1.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.986  -2.741   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.968   1.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.573   1.195   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.368   0.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.661  -3.526   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.242   1.970   0.000  0.00  0.00           C+0
CONECT    1   10   17                                                       
CONECT    2   12   17                                                       
CONECT    3   15                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    7    8   14                                                  
CONECT    7    6   16                                                       
CONECT    8    6    9   11                                                  
CONECT    9    8   13   15                                                  
CONECT   10    1   11   12                                                  
CONECT   11    8   10                                                       
CONECT   12    2   10   13                                                  
CONECT   13    9   12                                                       
CONECT   14    6   18                                                       
CONECT   15    3    9   16                                                  
CONECT   16    7   15   19                                                  
CONECT   17    1    2                                                       
CONECT   18   14                                                            
CONECT   19    4    5   16                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014965
HETATM    1  C1  UNL     1      -1.928  -2.581   0.226  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.684  -1.612  -0.933  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.248  -0.325  -0.482  1.00  0.00           N  
HETATM    4  N2  UNL     1      -2.162   0.601  -0.226  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.849   1.835   0.199  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.880   2.801   0.462  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.530   3.960   0.863  1.00  0.00           O  
HETATM    8  O2  UNL     1      -4.226   2.572   0.314  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.514   2.121   0.365  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.181   3.266   0.761  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.462   1.170   0.104  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.808   1.419   0.260  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.776   0.466  -0.001  1.00  0.00           C  
HETATM   14  C9  UNL     1       2.400  -0.789  -0.435  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.040  -1.041  -0.593  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.080  -0.086  -0.331  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.547  -1.566  -0.628  1.00  0.00           O  
HETATM   18  C12 UNL     1       4.594  -0.939   0.128  1.00  0.00           C  
HETATM   19  O5  UNL     1       4.166   0.422   0.061  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.047  -2.700   0.857  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.187  -3.551  -0.234  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.819  -2.189   0.769  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.083  -2.054  -1.738  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.709  -1.479  -1.391  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.800   2.234   1.065  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.110   2.396   0.599  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.765  -2.009  -0.926  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.526  -1.239   1.203  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.573  -1.104  -0.318  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   16
CONECT    4    5    5
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   25
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   26
CONECT   13   14   14   19
CONECT   14   15   17
CONECT   15   16   16   27
CONECT   17   18
CONECT   18   19   28   29
END

HMDB0014965
     RDKit          3D
Cinoxacin
 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.9278   -2.5807    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.6116   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -0.3251   -0.4821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623    0.6015   -0.2256 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493    1.8354    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795    2.8010    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    3.9595    0.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2261    2.5723    0.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144    2.1207    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1812    3.2661    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.1697    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078    1.4191    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765    0.4657   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996   -0.7885   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395   -1.0414   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802   -0.0859   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5470   -1.5656   -0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.9392    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664    0.4221    0.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.6997    0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1872   -3.5515   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.1889    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -2.0544   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -1.4787   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7999    2.2339    1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098    2.3961    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653   -2.0089   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261   -1.2394    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -1.1037   -0.3181 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  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 16  3  1  0
 16 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  8 25  1  0
 12 26  1  0
 15 27  1  0
 18 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid	ChEBI
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acid	ChEBI
Cinoxacine	ChEBI
Cinoxacino	ChEBI
Cinoxacinum	ChEBI
CINX	Kegg
Cinobac	Kegg
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylate	Generator
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylate	Generator
64716, Compound	HMDB
Azolinic acid	HMDB
Acid, azolinic	HMDB
Compound 64716	HMDB
Clinoxacin	HMDB

Chemical Formula

C₁₂H₁₀N₂O₅

Average Molecular Weight

262.2182

Monoisotopic Molecular Weight

262.05897144

IUPAC Name

1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

Traditional Name

cinoxacin

CAS Registry Number

28657-80-9

SMILES

CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

InChI Key

VDUWPHTZYNWKRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Cinnolines

Alternative Parents

Substituents

Cinnoline
Benzodioxole
Pyridazine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Oxacycle
Azacycle
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxacycle (CHEBI:3716 )
oxo carboxylic acid (CHEBI:3716 )
cinnolines (CHEBI:3716 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014965)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	261 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.96 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	148.476	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000973

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.96 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.72	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.6 m³·mol⁻¹	ChemAxon
Polarizability	24.72 Å³	ChemAxon
Number of Rings	3	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]+	159.816	31661259
DarkChem	[M-H]-	157.524	31661259
DeepCCS	[M-2H]-	188.14	30932474
DeepCCS	[M+Na]+	163.688	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.3	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.7	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	157.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinoxacin	CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	3070.0	Standard polar	33892256
Cinoxacin	CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	2281.8	Standard non polar	33892256
Cinoxacin	CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	2614.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinoxacin,1TMS,isomer #1	CCN1N=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC3=C(C=C21)OCO3	2503.2	Semi standard non polar	33892256
Cinoxacin,1TBDMS,isomer #1	CCN1N=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC3=C(C=C21)OCO3	2706.8	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 - Cinoxacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0970000000-d6e7abdaf83ac6915d9c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinoxacin GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4934000000-f98fd908e7ab28b030cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinoxacin 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 - Cinoxacin LC-ESI-qTof , Positive-QTOF	splash10-00kr-2930000000-d8548621f53001ee222d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinoxacin , positive-QTOF	splash10-00kr-2930000000-d8548621f53001ee222d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 10V, Positive-QTOF	splash10-03di-0090000000-334244d6a89f0ca6b546	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 20V, Positive-QTOF	splash10-02ta-0190000000-4212f062c3b83386b041	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 40V, Positive-QTOF	splash10-0gi0-0890000000-25eee1869a982bf913fc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 10V, Negative-QTOF	splash10-02t9-0290000000-79e8373fadc199462102	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 20V, Negative-QTOF	splash10-014i-0790000000-7942d2310d6730a23c27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 40V, Negative-QTOF	splash10-03dl-1900000000-05b7716167bca8f2dd58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 10V, Positive-QTOF	splash10-03di-0090000000-4fd0af9aad9b9655f431	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 20V, Positive-QTOF	splash10-0002-0090000000-4e532ea6a8a7a3dfc2f7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 40V, Positive-QTOF	splash10-03xr-1950000000-5d613602c0ff21ac9ab5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 10V, Negative-QTOF	splash10-03xr-0090000000-4920e9eef443d07b78d7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 20V, Negative-QTOF	splash10-000i-0920000000-9e4a8c05b0c3ecae8d01	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinoxacin 40V, Negative-QTOF	splash10-0909-0980000000-b400ebb127f6687745bf	2021-10-11	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 DB00827	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00827	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00827

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2660

KEGG Compound ID

C08052

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinoxacin

METLIN ID

Not Available

PubChem Compound

2762

PDB ID

Not Available

ChEBI ID

3716

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

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

Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

Showing metabocard for Cinoxacin (HMDB0014965)

MOL for HMDB0014965 (Cinoxacin)

3D MOL for HMDB0014965 (Cinoxacin)

3D SDF for HMDB0014965 (Cinoxacin)

3D-SDF for HMDB0014965 (Cinoxacin)

PDB for HMDB0014965 (Cinoxacin)

3D PDB for HMDB0014965 (Cinoxacin)

SMILES for HMDB0014965 (Cinoxacin)

INCHI for HMDB0014965 (Cinoxacin)

Structure for HMDB0014965 (Cinoxacin)

3D Structure for HMDB0014965 (Cinoxacin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References