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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:13:35 UTC

Update Date

2021-09-26 23:11:21 UTC

HMDB ID

HMDB0255996

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxolinic acid

Description

Oxolinic acid, also known as OA or acide oxolinique, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Based on a literature review a significant number of articles have been published on Oxolinic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Oxolinic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Oxolinic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255996
     RDKit          3D
Oxolinic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3719    2.9330    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817    1.9297    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    0.6283    0.6482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658   -0.1495    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550   -1.4148    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -2.2099   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -3.3647   -0.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.7319    0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8593   -1.9094   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535   -3.0436   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -1.1448   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5049   -1.6464   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -0.8858   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    0.3694   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.8627    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035    0.1125    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8651    0.9087   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -0.1480   -0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.1573   -1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    3.0619   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    3.9244    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8630    2.6057   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    2.3056    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0134    1.9718    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0027    0.2489    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077   -1.9335   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5431   -2.6362   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3589    1.8492    0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6026    0.1573   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1652   -0.4933    0.4671 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
  4 25  1  0
  8 26  1  0
 12 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
M  END


  Mrv0541 05041409062D          

 19 21  0  0  0  0            999 V2000
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18  6  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255996

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

> <INCHI_KEY>
KYGZCKSPAKDVKC-UHFFFAOYSA-N

> <FORMULA>
C13H11NO5

> <MOLECULAR_WEIGHT>
261.2301

> <EXACT_MASS>
261.063722467

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.521229530139497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
1.3531468610000004

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.579866110343406

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282722549478013

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
65.84330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ossian

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255996
     RDKit          3D
Oxolinic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3719    2.9330    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817    1.9297    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    0.6283    0.6482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658   -0.1495    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550   -1.4148    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -2.2099   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -3.3647   -0.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.7319    0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8593   -1.9094   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535   -3.0436   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -1.1448   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5049   -1.6464   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -0.8858   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    0.3694   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.8627    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035    0.1125    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8651    0.9087   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -0.1480   -0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.1573   -1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    3.0619   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    3.9244    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8630    2.6057   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    2.3056    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0134    1.9718    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0027    0.2489    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077   -1.9335   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5431   -2.6362   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3589    1.8492    0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6026    0.1573   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1652   -0.4933    0.4671 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
  4 25  1  0
  8 26  1  0
 12 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    7   10                                                       
CONECT    4    9   11                                                       
CONECT    5    8   14                                                       
CONECT    6   18   19                                                       
CONECT    7    3    9   12                                                  
CONECT    8    5   12   13                                                  
CONECT    9    4    7   14                                                  
CONECT   10    3   11   18                                                  
CONECT   11    4   10   19                                                  
CONECT   12    7    8   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14    2    5    9                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18    6   10                                                       
CONECT   19    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0255996
HETATM    1  C1  UNL     1      -1.372   2.933   0.121  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.082   1.930   1.238  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.947   0.628   0.648  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.066  -0.150   0.553  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.055  -1.415   0.016  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.266  -2.210  -0.067  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.227  -3.365  -0.562  1.00  0.00           O  
HETATM    8  O2  UNL     1      -4.482  -1.732   0.389  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.859  -1.909  -0.442  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.753  -3.044  -0.943  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.311  -1.145  -0.363  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.505  -1.646  -0.828  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.678  -0.886  -0.755  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.584   0.369  -0.206  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.357   0.863   0.262  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.204   0.113   0.190  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.865   0.909  -0.250  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.770  -0.148  -0.530  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.986  -1.157  -1.146  1.00  0.00           O  
HETATM   20  H1  UNL     1      -2.458   3.062  -0.033  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.966   3.924   0.407  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.863   2.606  -0.829  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.209   2.306   1.782  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.013   1.972   1.890  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.003   0.249   0.917  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.308  -1.933  -0.183  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.543  -2.636  -1.253  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.359   1.849   0.674  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.603   0.157  -1.164  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.165  -0.493   0.467  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   16
CONECT    4    5    5   25
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   27
CONECT   13   14   14   19
CONECT   14   15   17
CONECT   15   16   16   28
CONECT   17   18
CONECT   18   19   29   30
END

HMDB0255996
     RDKit          3D
Oxolinic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.3719    2.9330    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817    1.9297    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468    0.6283    0.6482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658   -0.1495    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550   -1.4148    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -2.2099   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -3.3647   -0.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.7319    0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8593   -1.9094   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535   -3.0436   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -1.1448   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5049   -1.6464   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775   -0.8858   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    0.3694   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.8627    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035    0.1125    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8651    0.9087   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -0.1480   -0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.1573   -1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    3.0619   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    3.9244    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8630    2.6057   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    2.3056    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0134    1.9718    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0027    0.2489    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077   -1.9335   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5431   -2.6362   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3589    1.8492    0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6026    0.1573   -1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1652   -0.4933    0.4671 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
  4 25  1  0
  8 26  1  0
 12 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid	ChEBI
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid	ChEBI
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid	ChEBI
Acide oxolinique	ChEBI
Acido oxolinico	ChEBI
Acidum oxolinicum	ChEBI
OA	ChEBI
Aqualinic	Kegg
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylate	Generator
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylate	Generator
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylate	Generator
Oxolinate	Generator
Acid, oxolinic	MeSH
Gramurin	MeSH
Oxolinate, sodium	MeSH
Sodium oxolinate	MeSH

Chemical Formula

C₁₃H₁₁NO₅

Average Molecular Weight

261.2301

Monoisotopic Molecular Weight

261.063722467

IUPAC Name

5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

Traditional Name

ossian

CAS Registry Number

Not Available

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

InChI Key

KYGZCKSPAKDVKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-3-carboxylic acid
Dihydroquinolone
Dihydroquinoline
Benzodioxole
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:138856 )
oxacycle (CHEBI:138856 )
quinolone antibiotic (CHEBI:138856 )
quinolinemonocarboxylic acid (CHEBI:138856 )
aromatic carboxylic acid (CHEBI:138856 )
Quinone fungicides (C11342 )

Ontology

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
logP	0.86	ALOGPS
logP	1.35	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	5.58	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.84 m³·mol⁻¹	ChemAxon
Polarizability	25.52 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
DeepCCS	[M-2H]-	189.726	30932474
DeepCCS	[M+Na]+	165.291	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]-	159.4	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxolinic acid	CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	3376.6	Standard polar	33892256
Oxolinic acid	CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	2226.3	Standard non polar	33892256
Oxolinic acid	CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12	2937.3	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 - Oxolinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l6-0490000000-237ab4e22ca8c87c87f9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolinic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolinic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-42a1a31f158e9bef1a7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QTOF , positive-QTOF	splash10-03di-0790000000-0196f4b3fe02d848ac04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QTOF , positive-QTOF	splash10-03di-0920000000-8df3687ee0c2e91f987f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-24298432855bfc523660	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-0511184317d1b6d18d3f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-95faf056ba91e8007c9b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03dl-0290000000-db6274d8128c051d14b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03e9-0960000000-c51deba0c41087d2cab2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-03e9-0910000000-bb9589ba074c27740963	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-0ho0-4900000000-a825bf27d8d3c0aee71f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-02di-9500000000-bccf49f73f4aeba1dfa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid LC-ESI-QFT , positive-QTOF	splash10-004i-9100000000-55f0b933bb95b8ac1a52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 90V, Positive-QTOF	splash10-03e9-0910000000-3c81458019c3bf0c9692	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 75V, Positive-QTOF	splash10-03e9-0960000000-f0f7c0d17b8af04334ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 60V, Positive-QTOF	splash10-03dl-0290000000-bf8142d91cf36f4709f4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 30V, Positive-QTOF	splash10-03di-0090000000-0511184317d1b6d18d3f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 45V, Positive-QTOF	splash10-03di-0090000000-9000f1dd05ac3d9ad631	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 50V, Positive-QTOF	splash10-03di-0920000000-741ae3bcdfd5e8398bf6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxolinic acid 40V, Positive-QTOF	splash10-03di-0790000000-a21c32a280f959c2466b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 10V, Positive-QTOF	splash10-03di-0090000000-37dc156faa14512ceaab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 20V, Positive-QTOF	splash10-0296-0090000000-4381353df0b7e7aeee1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 40V, Positive-QTOF	splash10-0wtc-0790000000-e290c90d551c56e1ef77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 10V, Negative-QTOF	splash10-02t9-0090000000-8aae635e5bdea056ef12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 20V, Negative-QTOF	splash10-014i-0590000000-4a91cc6c672c3b18ada6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolinic acid 40V, Negative-QTOF	splash10-000l-0920000000-cd83ad14bff62acfdf66	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13627

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4467

KEGG Compound ID

C11342

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxolinic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

138856

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Oxolinic acid (HMDB0255996)

MOL for HMDB0255996 (Oxolinic acid)

3D MOL for HMDB0255996 (Oxolinic acid)

3D SDF for HMDB0255996 (Oxolinic acid)

3D-SDF for HMDB0255996 (Oxolinic acid)

PDB for HMDB0255996 (Oxolinic acid)

3D PDB for HMDB0255996 (Oxolinic acid)

SMILES for HMDB0255996 (Oxolinic acid)

INCHI for HMDB0255996 (Oxolinic acid)

Structure for HMDB0255996 (Oxolinic acid)

3D Structure for HMDB0255996 (Oxolinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra