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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:46:37 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041895

Secondary Accession Numbers

HMDB41895

Metabolite Identification

Common Name

Flumequine

Description

Ciprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division. Flumequine is a 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The molecular formula is C14H12FNO3 It is a white powder, odorless, flavorless, insoluble in water but soluble in organic solvent. Flumequine is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed. It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries. It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone. However this was a limited indication because only minimal serum levels were achieved. The first quinolone used was nalidixic acid (was marketed in many countries as Negram) followed by the fluoroquinolone flumequine. The first-generation fluoroquinolone agents, such as flumequine, had poor distribution into the body tissues and limited activity. As such they were used mainly for treatment of urinary tract infections. Flumequine (benzo quinolizine) was first patented in 1973, (German Patent) by Rikker Labs. Flumequine is a known antimicrobial compound described and claimed in U.S. Pat. No. 3,896,131 (Example 3), July 22, 1975. Flumequine is the first quinolone compound with a fluorine atom at the C6-position of the related quinolone basic molecular structure. Even though this was the first fluoroquinolone, it is oftentimes overlooked when classifying the drugs within this class by generations and excluded from such a list. There continues to be considerable debate as to whether or not this DNA damage is to be considered one of the mechanisms of action concerning the severe adverse reactions experienced by some patients following fluoroquinolone therapy.

Structure

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

HMDB0041895
     RDKit          3D
Flumequine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.1114   -2.5177   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.7125    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871   -1.0801    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6426   -0.0138    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    0.9843   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625    2.2811   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    3.2449   -0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    4.5029   -0.8424 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127    2.8894   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7261    1.5871   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.2655   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    2.1522   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636   -0.0258    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -0.4103    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259    0.4892   -0.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.7113    0.4391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.9607    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.6582    0.2625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    0.6151   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922   -1.9409   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680   -2.8436   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -3.4658   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542   -2.4149    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -1.8633    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -0.5487    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.4441    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.4325   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    2.5245   -0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    3.6227   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437   -2.0320    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8087   -1.9703    0.5270 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 19  5  2  0
 19 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv0541 09131211462D          

 19 21  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041895

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)

> <INCHI_KEY>
DPSPPJIUMHPXMA-UHFFFAOYSA-N

> <FORMULA>
C14H12FNO3

> <MOLECULAR_WEIGHT>
261.2484

> <EXACT_MASS>
261.08012146

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.246669797951256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0⁵,¹³]trideca-2,5(13),6,8-tetraene-3-carboxylic acid

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
2.416839571

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.004770867103982

> <JCHEM_PKA_STRONGEST_BASIC>
-4.310946343966191

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
67.8736

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flumequine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041895
     RDKit          3D
Flumequine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.1114   -2.5177   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.7125    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871   -1.0801    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6426   -0.0138    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    0.9843   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625    2.2811   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    3.2449   -0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    4.5029   -0.8424 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127    2.8894   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7261    1.5871   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.2655   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    2.1522   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636   -0.0258    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -0.4103    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259    0.4892   -0.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.7113    0.4391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.9607    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.6582    0.2625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    0.6151   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922   -1.9409   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680   -2.8436   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -3.4658   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542   -2.4149    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -1.8633    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -0.5487    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.4441    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.4325   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    2.5245   -0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    3.6227   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437   -2.0320    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8087   -1.9703    0.5270 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 19  5  2  0
 19 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  F   UNK     0       1.334   8.470   0.000  0.00  0.00           F+0
HETATM   16  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    8    9                                                       
CONECT    5    9   10                                                       
CONECT    6   11   16                                                       
CONECT    7    1    2   16                                                  
CONECT    8    3    4   12                                                  
CONECT    9    4    5   15                                                  
CONECT   10    5   12   13                                                  
CONECT   11    6   13   14                                                  
CONECT   12    8   10   16                                                  
CONECT   13   10   11   17                                                  
CONECT   14   11   18   19                                                  
CONECT   15    9                                                            
CONECT   16    6    7   12                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0041895
HETATM    1  C1  UNL     1      -1.111  -2.518  -0.731  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.838  -1.712   0.505  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.087  -1.080   1.073  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.643  -0.014   0.158  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.570   0.984  -0.073  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.963   2.281  -0.351  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.015   3.245  -0.574  1.00  0.00           C  
HETATM    8  F1  UNL     1      -1.435   4.503  -0.842  1.00  0.00           F  
HETATM    9  C8  UNL     1       0.313   2.889  -0.513  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.726   1.587  -0.235  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.067   1.265  -0.182  1.00  0.00           C  
HETATM   12  O1  UNL     1       2.947   2.152  -0.387  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.464  -0.026   0.094  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.873  -0.410   0.160  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.726   0.489  -0.048  1.00  0.00           O  
HETATM   16  O3  UNL     1       4.216  -1.711   0.439  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.455  -0.961   0.311  1.00  0.00           C  
HETATM   18  N1  UNL     1       0.146  -0.658   0.263  1.00  0.00           N  
HETATM   19  C14 UNL     1      -0.229   0.615  -0.010  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.792  -1.941  -1.636  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.168  -2.844  -0.822  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.505  -3.466  -0.750  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.454  -2.415   1.278  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.808  -1.863   1.316  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.770  -0.549   2.009  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.508   0.444   0.680  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.033  -0.432  -0.792  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.030   2.524  -0.390  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.073   3.623  -0.683  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.144  -2.032   0.206  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.809  -1.970   0.527  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   18   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   19   19
CONECT    6    7    7   28
CONECT    7    8    9
CONECT    9   10   10   29
CONECT   10   11   19
CONECT   11   12   12   13
CONECT   13   14   17   17
CONECT   14   15   15   16
CONECT   16   30
CONECT   17   18   31
CONECT   18   19
END

HMDB0041895
     RDKit          3D
Flumequine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.1114   -2.5177   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.7125    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871   -1.0801    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6426   -0.0138    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    0.9843   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9625    2.2811   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    3.2449   -0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    4.5029   -0.8424 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127    2.8894   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7261    1.5871   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.2655   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471    2.1522   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636   -0.0258    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -0.4103    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259    0.4892   -0.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.7113    0.4391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.9607    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.6582    0.2625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    0.6151   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922   -1.9409   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680   -2.8436   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -3.4658   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542   -2.4149    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -1.8633    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -0.5487    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.4441    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.4325   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    2.5245   -0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    3.6227   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437   -2.0320    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8087   -1.9703    0.5270 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 19  5  2  0
 19 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
FLM	Kegg
Apurone	Kegg
9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate	HMDB
Flumequine	MeSH

Chemical Formula

C₁₄H₁₂FNO₃

Average Molecular Weight

261.2484

Monoisotopic Molecular Weight

261.08012146

IUPAC Name

7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0⁵,¹³]trideca-2,5(13),6,8-tetraene-3-carboxylic acid

Traditional Name

flumequine

CAS Registry Number

42835-25-6

SMILES

CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O

InChI Identifier

InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)

InChI Key

DPSPPJIUMHPXMA-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
Fluoroquinolone
Dihydroquinolone
Haloquinoline
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Benzenoid
Pyridine
Aryl fluoride
Aryl halide
Vinylogous amide
Heteroaromatic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:85269 )
quinolone antibiotic (CHEBI:85269 )
3-oxo monocarboxylic acid (CHEBI:85269 )
pyridoquinoline (CHEBI:85269 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041895)

Source

Exogenous

Exogenous (HMDB: HMDB0041895)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	253 - 255 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2186 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.60	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	149.762	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001009

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	1.62	ALOGPS
logP	2.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.87 m³·mol⁻¹	ChemAxon
Polarizability	25.25 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+H]+	161.224	30932474
DeepCCS	[M-H]-	158.866	30932474
DeepCCS	[M-2H]-	191.752	30932474
DeepCCS	[M+Na]+	167.317	30932474
AllCCS	[M+H]+	157.9	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	160.1	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.	6.17 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6937 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1849.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	462.8 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	635.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	936.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.7 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	1418.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	333.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.6 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	34.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flumequine	CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O	2870.4	Standard polar	33892256
Flumequine	CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O	2053.3	Standard non polar	33892256
Flumequine	CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O	2766.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flumequine,1TMS,isomer #1	CC1CCC2=C3C(=CC(F)=C2)C(=O)C(C(=O)O[Si](C)(C)C)=CN31	2430.4	Semi standard non polar	33892256
Flumequine,1TBDMS,isomer #1	CC1CCC2=C3C(=CC(F)=C2)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN31	2645.1	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 - Flumequine GC-MS (Non-derivatized) - 70eV, Positive	splash10-02td-0190000000-d99bc59675d12cd5e4a9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flumequine GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9166000000-57d63f1f1cfe90f640bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flumequine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flumequine 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 - Flumequine LC-ESI-qTof , Positive-QTOF	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-4562bd1b09907dc3b700	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOF	splash10-0uk9-0190000000-0bac3ec6458648a725c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOF	splash10-0fk9-0980000000-91b57386bd019dd7838b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-938a6d39c487a729e57e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-03dl-0090000000-73779217b6427d238ce0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-01ox-0090000000-13657a0f167139ce56f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0h2f-0090000000-def6112d5472cfde4da7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0fk9-0190000000-56e0b22aa033cf49c8c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0fk9-0980000000-e04498a4742bec91275e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0ufs-2900000000-068e7a9b1ae656d70d01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0f92-9800000000-b99a0e425235a9128533	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-0f6t-9300000000-164deed4d2600172d871	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine , positive-QTOF	splash10-01ox-0090000000-7b3c06efa7853de57efb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine , positive-QTOF	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-9604f2662310bea2bfe7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine 90V, Positive-QTOF	splash10-0fk9-0890000000-c7445bd8c0c09c1feef7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine 20V, Positive-QTOF	splash10-03dl-0090000000-305e228c2c2a38446f19	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flumequine 35V, Positive-QTOF	splash10-03di-0090000000-4565c8d43013294a9ff4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 10V, Positive-QTOF	splash10-03di-0090000000-3bd1178d60063e7ccbde	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 20V, Positive-QTOF	splash10-02tc-0090000000-dd8fd2eb769868a3ed15	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 40V, Positive-QTOF	splash10-0gbd-0490000000-b900a0ae75214bdfabee	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 10V, Negative-QTOF	splash10-02t9-0090000000-dfabe88649d6507b3599	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 20V, Negative-QTOF	splash10-014i-0290000000-8169716cf15c21437036	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flumequine 40V, Negative-QTOF	splash10-0hn1-1950000000-cb83bcde14854f583e5d	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08972

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flumequine

METLIN ID

Not Available

PubChem Compound

3374

PDB ID

Not Available

ChEBI ID

85269

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1080101

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Flumequine (HMDB0041895)

MOL for HMDB0041895 (Flumequine)

3D MOL for HMDB0041895 (Flumequine)

3D SDF for HMDB0041895 (Flumequine)

3D-SDF for HMDB0041895 (Flumequine)

PDB for HMDB0041895 (Flumequine)

3D PDB for HMDB0041895 (Flumequine)

SMILES for HMDB0041895 (Flumequine)

INCHI for HMDB0041895 (Flumequine)

Structure for HMDB0041895 (Flumequine)

3D Structure for HMDB0041895 (Flumequine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra