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

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014630

Secondary Accession Numbers

HMDB14630

Metabolite Identification

Common Name

Pefloxacin

Description

Pefloxacin is only found in individuals that have used or taken this drug. It is a synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria. [PubChem]The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.

Structure

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

HMDB0014630
     RDKit          3D
Pefloxacin
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.3048    2.2765   -2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    2.2105   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    0.8856   -0.3201 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318    0.5419   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4100   -0.7129    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283   -1.0698    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7355   -0.2431    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -2.3349    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -1.6750    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601   -2.8238    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1394   -1.3434    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -2.2720    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -1.8902    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -2.7751    0.7559 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.6306    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -0.2685   -0.0873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7635   -0.9817   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -0.9631   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6421    0.3964   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057    0.5297    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    1.3663   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    0.8265    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.2531   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -0.0797   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3343    2.0873   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138    3.2947   -2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    1.5003   -2.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    2.7089   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057    2.8556   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2727   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0523   -3.0962    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4333   -3.2476    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561   -0.5412   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.0450   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -1.6315   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749   -1.2964    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -0.4723    0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5849    1.1916   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8708    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    2.2833    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    1.6200   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    1.6604    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.5054    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189    1.2564   -0.5221 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  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 15 23  1  0
 23 24  2  0
 24  3  1  0
 24 11  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
M  END

487
  Mrv0541 02231214432D          

 24 26  0  0  0  0            999 V2000
    7.1488    1.0653    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -0.6246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5746   -1.4551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456   -1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8649   -0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5778   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884   -0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2874   -1.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884    1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 20  2  0  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 15  1  0  0  0  0
  7 13  1  0  0  0  0
  7 19  1  0  0  0  0
  7 21  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 14  2  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014630

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)

> <INCHI_KEY>
FHFYDNQZQSQIAI-UHFFFAOYSA-N

> <FORMULA>
C17H20FN3O3

> <MOLECULAR_WEIGHT>
333.3574

> <EXACT_MASS>
333.148869726

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.42486699048514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
0.8768125676894498

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.664761411657647

> <JCHEM_PKA_STRONGEST_BASIC>
6.472901788448982

> <JCHEM_POLAR_SURFACE_AREA>
64.09

> <JCHEM_REFRACTIVITY>
90.77149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pefloxacin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014630
     RDKit          3D
Pefloxacin
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.3048    2.2765   -2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    2.2105   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    0.8856   -0.3201 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318    0.5419   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4100   -0.7129    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283   -1.0698    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7355   -0.2431    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -2.3349    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -1.6750    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601   -2.8238    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1394   -1.3434    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -2.2720    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -1.8902    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -2.7751    0.7559 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.6306    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -0.2685   -0.0873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7635   -0.9817   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -0.9631   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6421    0.3964   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057    0.5297    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    1.3663   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    0.8265    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.2531   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -0.0797   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3343    2.0873   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138    3.2947   -2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    1.5003   -2.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    2.7089   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057    2.8556   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2727   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0523   -3.0962    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4333   -3.2476    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561   -0.5412   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.0450   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -1.6315   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749   -1.2964    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -0.4723    0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5849    1.1916   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8708    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    2.2833    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    1.6200   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    1.6604    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.5054    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189    1.2564   -0.5221 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  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 15 23  1  0
 23 24  2  0
 24  3  1  0
 24 11  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 487                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0      13.344   1.989   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.908   3.491   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   1.181   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241   3.491   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.344  -1.166   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      16.006  -2.716   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.908  -1.129   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.338  -2.706   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.681  -0.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.669  -3.481   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.012  -1.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.014  -0.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242  -0.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.618  -1.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.336  -3.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.014   1.213   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.242   1.181   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.618   2.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908  -2.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.908   1.951   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.574  -0.359   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.574   1.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.574  -3.439   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.241   1.951   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   20                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    8    9   12                                                  
CONECT    6   10   11   15                                                  
CONECT    7   13   19   21                                                  
CONECT    8    5   10                                                       
CONECT    9    5   11                                                       
CONECT   10    6    8                                                       
CONECT   11    6    9                                                       
CONECT   12    5   14   16                                                  
CONECT   13    7   14   17                                                  
CONECT   14   12   13                                                       
CONECT   15    6                                                            
CONECT   16    1   12   18                                                  
CONECT   17   13   18   20                                                  
CONECT   18   16   17                                                       
CONECT   19    7   23                                                       
CONECT   20    2   17   22                                                  
CONECT   21    7   22                                                       
CONECT   22   20   21   24                                                  
CONECT   23   19                                                            
CONECT   24    3    4   22                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0014630
HETATM    1  C1  UNL     1       2.305   2.277  -2.289  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.401   2.211  -0.760  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.722   0.886  -0.320  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.032   0.542  -0.168  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.410  -0.713   0.254  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.828  -1.070   0.414  1.00  0.00           C  
HETATM    7  O1  UNL     1       6.736  -0.243   0.171  1.00  0.00           O  
HETATM    8  O2  UNL     1       6.202  -2.335   0.840  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.465  -1.675   0.541  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.760  -2.824   0.926  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.139  -1.343   0.392  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.128  -2.272   0.664  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.182  -1.890   0.498  1.00  0.00           C  
HETATM   14  F1  UNL     1      -1.179  -2.775   0.756  1.00  0.00           F  
HETATM   15  C10 UNL     1      -0.546  -0.631   0.074  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.887  -0.269  -0.087  1.00  0.00           N  
HETATM   17  C11 UNL     1      -2.763  -0.982  -1.025  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.167  -0.963  -0.462  1.00  0.00           C  
HETATM   19  N3  UNL     1      -4.642   0.396  -0.523  1.00  0.00           N  
HETATM   20  C13 UNL     1      -5.806   0.530   0.296  1.00  0.00           C  
HETATM   21  C14 UNL     1      -3.620   1.366  -0.245  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.523   0.826   0.645  1.00  0.00           C  
HETATM   23  C16 UNL     1       0.483   0.253  -0.183  1.00  0.00           C  
HETATM   24  C17 UNL     1       1.819  -0.080  -0.031  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.334   2.087  -2.658  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.014   3.295  -2.553  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.590   1.500  -2.662  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.579   2.709  -0.252  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.306   2.856  -0.538  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.807   1.273  -0.384  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.052  -3.096   0.200  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.433  -3.248   0.993  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.756  -0.541  -2.021  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.447  -2.045  -1.077  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.793  -1.632  -1.084  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.175  -1.296   0.601  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.268  -0.472   0.412  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.585   1.192  -0.155  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.553   0.871   1.326  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.067   2.283   0.144  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.133   1.620  -1.221  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.769   1.660   0.736  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.902   0.505   1.629  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.219   1.256  -0.522  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   24
CONECT    4    5    5   30
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   31
CONECT    9   10   10   11
CONECT   11   12   12   24
CONECT   12   13   32
CONECT   13   14   15   15
CONECT   15   16   23
CONECT   16   17   22
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   20   21
CONECT   20   37   38   39
CONECT   21   22   40   41
CONECT   22   42   43
CONECT   23   24   24   44
END

HMDB0014630
     RDKit          3D
Pefloxacin
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.3048    2.2765   -2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    2.2105   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    0.8856   -0.3201 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318    0.5419   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4100   -0.7129    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283   -1.0698    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7355   -0.2431    0.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -2.3349    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -1.6750    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601   -2.8238    0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1394   -1.3434    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -2.2720    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -1.8902    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -2.7751    0.7559 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.6306    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -0.2685   -0.0873 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7635   -0.9817   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665   -0.9631   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6421    0.3964   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057    0.5297    0.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    1.3663   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    0.8265    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.2531   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -0.0797   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3343    2.0873   -2.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138    3.2947   -2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    1.5003   -2.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    2.7089   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057    2.8556   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2727   -0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0523   -3.0962    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4333   -3.2476    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561   -0.5412   -2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.0450   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -1.6315   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1749   -1.2964    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -0.4723    0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5849    1.1916   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529    0.8708    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674    2.2833    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    1.6200   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    1.6604    0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.5054    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189    1.2564   -0.5221 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  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 15 23  1  0
 23 24  2  0
 24  3  1  0
 24 11  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Labocton	ChEBI
Pefloxacine	ChEBI
Pefloxacino	ChEBI
Pefloxacinum	ChEBI
Perfloxacin	ChEBI
PFLX	ChEBI
2589 R.B.	HMDB
Dihydrate, pefloxacin mesylate	HMDB
Mesylate dihydrate, pefloxacin	HMDB
Mesylate, pefloxacin	HMDB
Pefloxacin, silver	HMDB
R.B., 2589	HMDB
Silver pefloxacin	HMDB
Abactal	HMDB
Peflacine	HMDB
Pefloxacin mesylate dihydrate	HMDB
Pefloxacin mesylate	HMDB

Chemical Formula

C₁₇H₂₀FN₃O₃

Average Molecular Weight

333.3574

Monoisotopic Molecular Weight

333.148869726

IUPAC Name

1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

pefloxacin

CAS Registry Number

70458-92-3

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1

InChI Identifier

InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)

InChI Key

FHFYDNQZQSQIAI-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
N-arylpiperazine
Aminoquinoline
Haloquinoline
Dihydroquinolone
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
N-alkylpiperazine
N-methylpiperazine
Benzenoid
Pyridine
Aryl fluoride
Piperazine
Aryl halide
1,4-diazinane
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organofluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:50199 )
N-alkylpiperazine (CHEBI:50199 )
quinolone antibiotic (CHEBI:50199 )
fluoroquinolone antibiotic (CHEBI:50199 )
quinolone (CHEBI:50199 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014630)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	271 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.23 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.23 g/L	ALOGPS
logP	0.2	ALOGPS
logP	0.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.66	ChemAxon
pKa (Strongest Basic)	6.47	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.77 m³·mol⁻¹	ChemAxon
Polarizability	34.42 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]-	208.455	30932474
DeepCCS	[M+Na]+	183.683	30932474
AllCCS	[M+H]+	176.2	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	179.1	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	180.9	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pefloxacin	CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1	3186.5	Standard polar	33892256
Pefloxacin	CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1	2420.4	Standard non polar	33892256
Pefloxacin	CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1	3403.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pefloxacin,1TMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C21	2816.4	Semi standard non polar	33892256
Pefloxacin,1TBDMS,isomer #1	CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C21	3028.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pefloxacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-2097000000-370bf9179a4cf52fec75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pefloxacin GC-MS (1 TMS) - 70eV, Positive	splash10-006x-3029000000-4dd5ce82a9202f9b5560	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pefloxacin 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 - Pefloxacin LC-ESI-qTof , Positive-QTOF	splash10-014i-0910000000-593baa616326abe5f576	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pefloxacin , positive-QTOF	splash10-001i-0198000000-230c93f5eaf4301ff8c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pefloxacin , positive-QTOF	splash10-014i-0910000000-593baa616326abe5f576	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pefloxacin 35V, Positive-QTOF	splash10-014i-0059000000-1866d360f2e81f4ba9c1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 10V, Positive-QTOF	splash10-001i-0019000000-25fe5a0dc40207dfef6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 20V, Positive-QTOF	splash10-00m0-1096000000-bc6a3c8df7f8e0b0b7e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 40V, Positive-QTOF	splash10-05fu-3190000000-796270374d7a22abcfd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 10V, Negative-QTOF	splash10-0019-0096000000-70569962374bf90574ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 20V, Negative-QTOF	splash10-000i-1090000000-962550d8a22c796bf083	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 40V, Negative-QTOF	splash10-06yd-2290000000-bd24e2048e0f6663993d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 10V, Negative-QTOF	splash10-00m0-0095000000-5a58bbc5df0e4a799193	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 20V, Negative-QTOF	splash10-0900-0090000000-c09507865afbb9b7d996	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 40V, Negative-QTOF	splash10-0c00-0090000000-fafb6f2ecd67dea79db2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 10V, Positive-QTOF	splash10-001i-0009000000-6d1487a779cd72a057aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 20V, Positive-QTOF	splash10-014i-0039000000-69403be99674b7fc55a6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pefloxacin 40V, Positive-QTOF	splash10-000j-2091000000-246d3633a80de308b831	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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 DB00487	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00487	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00487

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

46291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pefloxacin

METLIN ID

Not Available

PubChem Compound

51081

PDB ID

Not Available

ChEBI ID

50199

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

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Pefloxacin (HMDB0014630)

MOL for HMDB0014630 (Pefloxacin)

3D MOL for HMDB0014630 (Pefloxacin)

3D SDF for HMDB0014630 (Pefloxacin)

3D-SDF for HMDB0014630 (Pefloxacin)

PDB for HMDB0014630 (Pefloxacin)

3D PDB for HMDB0014630 (Pefloxacin)

SMILES for HMDB0014630 (Pefloxacin)

INCHI for HMDB0014630 (Pefloxacin)

Structure for HMDB0014630 (Pefloxacin)

3D Structure for HMDB0014630 (Pefloxacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References