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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:43:18 UTC

Update Date

2021-09-14 15:20:03 UTC

HMDB ID

HMDB0001929

Secondary Accession Numbers

HMDB01929

Metabolite Identification

Common Name

Levofloxacin

Description

Levofloxacin, also known as (S)-ofloxacin or cravit, 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. Levofloxacin is a very strong basic compound (based on its pKa). Levofloxacin is a bitter tasting compound. Outside of the human body,. Levofloxacin is a potentially toxic compound. A double mutant form of S. pneumoniae Gyr A + Par C bearing Ser-81-->Phe and Ser-79-->Phe mutations were eight to sixteen times less responsive to ciprofloxacin.

Structure

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

1137
  Mrv1652305271900192D          

 26 29  0  0  1  0            999 V2000
    5.2224    2.1733    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   -0.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3574    0.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3958   -2.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0858   -1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357   -1.1610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.1733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4948   -1.5965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9594   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4980   -2.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6460   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571   -1.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3796   -1.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 14  1  0  0  0  0
  2 17  1  0  0  0  0
  3 23  2  0  0  0  0
  4 26  1  0  0  0  0
  5 26  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 20  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 24  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 22  1  1  0  0  0
 12 14  1  0  0  0  0
 12 19  2  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 18 21  2  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 20 25  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0001929
     RDKit          3D
Levofloxacin
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.1749   -2.4391   -1.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039   -1.8636   -0.9785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724   -1.4813   -1.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -1.0549   -0.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    0.0317    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.8984    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    0.7520    0.2557 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    1.7444    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    1.4095    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.0005    0.5717 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.4081    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571   -0.5932   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.3919   -0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    1.9569    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812    2.8866    1.8002 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745    2.1073    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002    1.2201    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440    1.3757    1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    2.3593    2.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206    0.4652    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7566    0.6118    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5654    1.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -0.2884    0.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -0.5901    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -0.7445   -0.2110 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883    0.1441    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.6356   -2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.1067   -2.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592   -3.0319   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -2.6447   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.3460   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6498   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011    1.7334    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    2.7753    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247    1.6870   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    2.0072    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044   -1.3857    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3977   -0.5935   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5189    0.3182    1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.6768   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3585   -0.1335   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869   -0.4002   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -1.3099    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    2.9387    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779   -0.8840    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5655   -1.3352   -0.3751 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24 25  1  0
 25 26  1  0
 25  2  1  0
 26  5  2  0
 13  7  1  0
 26 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 23 45  1  0
 24 46  1  0
M  END

1137
  Mrv1652305271900192D          

 26 29  0  0  1  0            999 V2000
    5.2224    2.1733    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   -0.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3574    0.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3958   -2.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0858   -1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357   -1.1610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.1733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4948   -1.5965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9594   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4980   -2.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6460   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571   -1.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3796   -1.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 14  1  0  0  0  0
  2 17  1  0  0  0  0
  3 23  2  0  0  0  0
  4 26  1  0  0  0  0
  5 26  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 20  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 24  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 22  1  1  0  0  0
 12 14  1  0  0  0  0
 12 19  2  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 18 21  2  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 20 25  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001929

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1

> <INCHI_KEY>
GSDSWSVVBLHKDQ-JTQLQIEISA-N

> <FORMULA>
C18H20FN3O4

> <MOLECULAR_WEIGHT>
361.3675

> <EXACT_MASS>
361.143784348

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69213757884126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.6542797513181725

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.447057265936005

> <JCHEM_PKA_STRONGEST_BASIC>
6.20144920703161

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
94.93590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001929
     RDKit          3D
Levofloxacin
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.1749   -2.4391   -1.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039   -1.8636   -0.9785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724   -1.4813   -1.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -1.0549   -0.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    0.0317    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.8984    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    0.7520    0.2557 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    1.7444    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    1.4095    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.0005    0.5717 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.4081    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571   -0.5932   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.3919   -0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    1.9569    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812    2.8866    1.8002 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745    2.1073    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002    1.2201    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440    1.3757    1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    2.3593    2.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206    0.4652    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7566    0.6118    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5654    1.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -0.2884    0.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -0.5901    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -0.7445   -0.2110 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883    0.1441    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.6356   -2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.1067   -2.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592   -3.0319   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -2.6447   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.3460   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6498   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011    1.7334    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    2.7753    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247    1.6870   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    2.0072    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044   -1.3857    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3977   -0.5935   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5189    0.3182    1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.6768   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3585   -0.1335   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869   -0.4002   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -1.3099    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    2.9387    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779   -0.8840    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5655   -1.3352   -0.3751 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24 25  1  0
 25 26  1  0
 25  2  1  0
 26  5  2  0
 13  7  1  0
 26 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 23 45  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1137                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  F   UNK     0       9.748   4.057   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.013  -0.574   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.734   0.225   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.805  -4.366   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.093  -2.030   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081   2.517   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.773  -2.167   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414   4.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.081   4.057   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   1.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.390  -2.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -0.563   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   0.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748   4.827   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   2.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.001  -2.178   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   0.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   2.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.124  -2.880   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   1.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.396  -4.520   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.406  -0.555   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   4.827   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.427  -2.082   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.775  -2.826   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   14   17                                                       
CONECT    3   23                                                            
CONECT    4   26                                                            
CONECT    5   26                                                            
CONECT    6    9   10   12                                                  
CONECT    7   11   13   20                                                  
CONECT    8   15   16   24                                                  
CONECT    9    6   15                                                       
CONECT   10    6   16                                                       
CONECT   11    7   17   22                                                  
CONECT   12    6   14   19                                                  
CONECT   13    7   14   18                                                  
CONECT   14    2   12   13                                                  
CONECT   15    8    9                                                       
CONECT   16    8   10                                                       
CONECT   17    2   11                                                       
CONECT   18   13   21   23                                                  
CONECT   19    1   12   21                                                  
CONECT   20    7   25                                                       
CONECT   21   18   19                                                       
CONECT   22   11                                                            
CONECT   23    3   18   25                                                  
CONECT   24    8                                                            
CONECT   25   20   23   26                                                  
CONECT   26    4    5   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0001929
HETATM    1  C1  UNL     1      -3.175  -2.439  -1.876  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.104  -1.864  -0.978  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.872  -1.481  -1.746  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.064  -1.055  -0.738  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.312   0.032   0.038  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.630   0.898   0.506  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.053   0.752   0.256  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.946   1.744   0.766  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.374   1.409   0.444  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.548   0.001   0.572  1.00  0.00           N  
HETATM   11  C8  UNL     1       5.919  -0.408   0.760  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.957  -0.593  -0.614  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.469  -0.392  -0.481  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.167   1.957   1.269  1.00  0.00           C  
HETATM   15  F1  UNL     1       0.981   2.887   1.800  1.00  0.00           F  
HETATM   16  C12 UNL     1      -1.175   2.107   1.529  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.100   1.220   1.047  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.444   1.376   1.306  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.796   2.359   2.004  1.00  0.00           O  
HETATM   20  C15 UNL     1      -4.321   0.465   0.799  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.757   0.612   1.063  1.00  0.00           C  
HETATM   22  O3  UNL     1      -6.182   1.565   1.749  1.00  0.00           O  
HETATM   23  O4  UNL     1      -6.672  -0.288   0.567  1.00  0.00           O  
HETATM   24  C17 UNL     1      -3.895  -0.590   0.045  1.00  0.00           C  
HETATM   25  N3  UNL     1      -2.570  -0.745  -0.211  1.00  0.00           N  
HETATM   26  C18 UNL     1      -1.688   0.144   0.280  1.00  0.00           C  
HETATM   27  H1  UNL     1      -3.662  -1.636  -2.461  1.00  0.00           H  
HETATM   28  H2  UNL     1      -2.661  -3.107  -2.605  1.00  0.00           H  
HETATM   29  H3  UNL     1      -3.859  -3.032  -1.261  1.00  0.00           H  
HETATM   30  H4  UNL     1      -1.801  -2.645  -0.231  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.442  -2.346  -2.296  1.00  0.00           H  
HETATM   32  H6  UNL     1      -1.098  -0.650  -2.437  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.901   1.733   1.901  1.00  0.00           H  
HETATM   34  H8  UNL     1       2.687   2.775   0.409  1.00  0.00           H  
HETATM   35  H9  UNL     1       4.525   1.687  -0.639  1.00  0.00           H  
HETATM   36  H10 UNL     1       5.099   2.007   1.032  1.00  0.00           H  
HETATM   37  H11 UNL     1       5.904  -1.386   1.286  1.00  0.00           H  
HETATM   38  H12 UNL     1       6.398  -0.594  -0.240  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.519   0.318   1.317  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.164  -1.677  -0.619  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.358  -0.134  -1.544  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.087  -0.400  -1.533  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.120  -1.310   0.095  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.543   2.939   2.128  1.00  0.00           H  
HETATM   45  H19 UNL     1      -7.178  -0.884   1.192  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.566  -1.335  -0.375  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   25   30
CONECT    3    4   31   32
CONECT    4    5
CONECT    5    6   26   26
CONECT    6    7   14   14
CONECT    7    8   13
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   12
CONECT   11   37   38   39
CONECT   12   13   40   41
CONECT   13   42   43
CONECT   14   15   16
CONECT   16   17   17   44
CONECT   17   18   26
CONECT   18   19   19   20
CONECT   20   21   24   24
CONECT   21   22   22   23
CONECT   23   45
CONECT   24   25   46
CONECT   25   26
END

HMDB0001929
     RDKit          3D
Levofloxacin
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.1749   -2.4391   -1.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039   -1.8636   -0.9785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724   -1.4813   -1.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -1.0549   -0.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    0.0317    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    0.8984    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    0.7520    0.2557 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    1.7444    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742    1.4095    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.0005    0.5717 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9186   -0.4081    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571   -0.5932   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -0.3919   -0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    1.9569    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812    2.8866    1.8002 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745    2.1073    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002    1.2201    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4440    1.3757    1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    2.3593    2.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206    0.4652    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7566    0.6118    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5654    1.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -0.2884    0.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949   -0.5901    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -0.7445   -0.2110 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6883    0.1441    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.6356   -2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.1067   -2.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592   -3.0319   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -2.6447   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -2.3460   -2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -0.6498   -2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011    1.7334    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    2.7753    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247    1.6870   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    2.0072    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044   -1.3857    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3977   -0.5935   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5189    0.3182    1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.6768   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3585   -0.1335   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869   -0.4002   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -1.3099    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    2.9387    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1779   -0.8840    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5655   -1.3352   -0.3751 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24 25  1  0
 25 26  1  0
 25  2  1  0
 26  5  2  0
 13  7  1  0
 26 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 23 45  1  0
 24 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Ofloxacin	ChEBI
(3S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid	ChEBI
(S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid	ChEBI
(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid	ChEBI
(S)-Ofloxacin	ChEBI
L-Ofloxacin	ChEBI
Levofloxacine	ChEBI
Levofloxacino	ChEBI
Levofloxacinum	ChEBI
Ofloxacin S-(-)-form	ChEBI
Cravit	Kegg
Levaquin	Kegg
(3S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate	Generator
(S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylate	Generator
(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylate	Generator
Floxin	HMDB
Levofloxacin hydrate	HMDB
Ofloxacin	HMDB
Quixin	HMDB
Ofloxacin, (S)-isomer	HMDB
Anhydrous, levofloxacin	HMDB
Levofloxacin anhydrous	HMDB

Chemical Formula

C₁₈H₂₀FN₃O₄

Average Molecular Weight

361.3675

Monoisotopic Molecular Weight

361.143784348

IUPAC Name

(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

Traditional Name

(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

CAS Registry Number

100986-85-4

SMILES

C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1

InChI Identifier

InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1

InChI Key

GSDSWSVVBLHKDQ-JTQLQIEISA-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
Benzoxazine
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
N-alkylpiperazine
N-methylpiperazine
Alkyl aryl ether
Benzenoid
Pyridine
Aryl fluoride
Piperazine
Aryl halide
1,4-diazinane
Vinylogous amide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Amino acid
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organofluoride
Hydrocarbon derivative
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolone antibiotic (CHEBI:63598 )
fluoroquinolone antibiotic (CHEBI:63598 )
ofloxacin (CHEBI:63598 )

Ontology

Disposition

Biological location

Excreta

Feces

Cellular substructure

Macromolecular complex

Blood

Organ

Prostate

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	10^(-0.02) g/L	ALOGPS
logP	10^(0.65) g/L	ChemAxon
logS	10^(-2.4) g/L	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.94 m³·mol⁻¹	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+		31661259
DarkChem	[M-H]-		31661259
AllCCS	[M+H]+	182.626	32859911
AllCCS	[M-H]-	186.228	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levofloxacin	C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1	3451.5	Standard polar	33892256
Levofloxacin	C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1	2777.3	Standard non polar	33892256
Levofloxacin	C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1	3518.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levofloxacin,1TMS,isomer #1	C[C@H]1COC2=C3C(=CC(F)=C2N2CCN(C)CC2)C(=O)C(C(=O)O[Si](C)(C)C)=CN31	2995.3	Semi standard non polar	33892256
Levofloxacin,1TBDMS,isomer #1	C[C@H]1COC2=C3C(=CC(F)=C2N2CCN(C)CC2)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN31	3185.7	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 - Levofloxacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2019000000-30d77332fe9feb70a82d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levofloxacin GC-MS (1 TMS) - 70eV, Positive	splash10-01dl-7009600000-d322709717558bd09e25	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levofloxacin 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 - Levofloxacin Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-00gm-1315975420-b0c4e6cdef799fda69b4	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0abc-3459425420-e8a4ecd2f8aea93fa660	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0h9p-3513893500-1d5c8069419fa2c37ebb	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin LC-ESI-QFT , positive-QTOF	splash10-03di-0009000000-63138044688fa3ab0792	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin LC-ESI-QFT , positive-QTOF	splash10-02t9-0019000000-265eec70cbb77077fbfa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin LC-ESI-QFT , positive-QTOF	splash10-03di-1290000000-3ff2c315dfac97ded8c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin LC-ESI-QFT , positive-QTOF	splash10-0axr-1980000000-e31472e2487627c51cea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin LC-ESI-QFT , positive-QTOF	splash10-0adl-1930000000-3cd445f16118ecf3f610	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin , positive-QTOF	splash10-03di-0049000000-3cbab894a4b0d1165e7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin , positive-QTOF	splash10-03di-2492000000-62b30ac9148b06791816	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin 75V, Positive-QTOF	splash10-0axr-1980000000-aa52ed55d102e4d6142f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin 60V, Positive-QTOF	splash10-03di-1190000000-77760aedde03dab8af8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin 30V, Positive-QTOF	splash10-02t9-0019000000-21613398a8dff5fc5e57	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levofloxacin 15V, Positive-QTOF	splash10-03di-0009000000-47e7a80ef7c8861677f6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 10V, Positive-QTOF	splash10-03di-0009000000-6e3992e2c7f71e2e2d60	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 20V, Positive-QTOF	splash10-02tc-0009000000-8e0f1b0fc3b80969c0dd	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 40V, Positive-QTOF	splash10-0pi3-7097000000-363d82fc0e563a2423b0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 10V, Negative-QTOF	splash10-02t9-0009000000-bf579599f29511ea990c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 20V, Negative-QTOF	splash10-0670-0096000000-9d4af124e757cd0455bb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 40V, Negative-QTOF	splash10-014r-0091000000-c5e349004a62406fb095	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 10V, Positive-QTOF	splash10-03dl-0009000000-c49f6f12144cd4de39cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 20V, Positive-QTOF	splash10-0006-0009000000-7979df79be5019e8bd92	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 40V, Positive-QTOF	splash10-0udl-1079000000-68ac9a2c90e1aa665339	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 10V, Negative-QTOF	splash10-03di-0019000000-ae9c58f7e3ad98591163	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levofloxacin 20V, Negative-QTOF	splash10-0002-0095000000-baf3b8295498cac74a7b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.135 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	17549677	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.206 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.569 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.510 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.907 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.242 +/- 9.802 uM	Adult (>18 years old)	Both	external ventriculostomy	14506016	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	19.383 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.763 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.297 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	12.599 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.652 +/- 0.692 uM	Not Specified	Not Specified	4hrs after administration of 300mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.510 uM	Not Specified	Not Specified	2hrs after administration of 500mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.206 uM	Not Specified	Not Specified	5hrs after administration of 750mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.242 +/- 9.802 uM	Not Specified	Not Specified	2hrs after IV administration of 500mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.297 uM	Not Specified	Not Specified	2hrs after administration of 750mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.652 +/- 0.692 uM	Not Specified	Not Specified	neurosurgical operations	12016861	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Tuberculosis
Upton A, Woodhouse A, Vaughan R, Newton S, Ellis-Pegler R: Evolution of central nervous system multidrug-resistant Mycobacterium tuberculosis and late relapse of cryptic prosthetic hip joint tuberculosis: complications during treatment of disseminated isoniazid-resistant tuberculosis in an immunocompromised host. J Clin Microbiol. 2009 Feb;47(2):507-10. doi: 10.1128/JCM.01473-08. Epub 2008 Dec 24. [PubMed:19109477 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

607948 (Tuberculosis)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB01137

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022746

KNApSAcK ID

Not Available

Chemspider ID

131410

KEGG Compound ID

C07660

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levofloxacin

METLIN ID

Not Available

PubChem Compound

149096

PDB ID

Not Available

ChEBI ID

63598

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)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Norrby SR: Levofloxacin. Expert Opin Pharmacother. 1999 Nov;1(1):109-19. [PubMed:11249554 ]
Chow AT, Chen A, Lattime H, Morgan N, Wong F, Fowler C, Williams RR: Penetration of levofloxacin into skin tissue after oral administration of multiple 750 mg once-daily doses. J Clin Pharm Ther. 2002 Apr;27(2):143-50. [PubMed:11975700 ]
Bielecka-Grzela S, Klimowicz A: Evaluation of ofloxacin penetration into the skin after a single oral dose assessed by cutaneous microdialysis. Pol J Pharmacol. 2003 Jul-Aug;55(4):613-8. [PubMed:14581720 ]

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

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

Showing metabocard for Levofloxacin (HMDB0001929)

MOL for HMDB0001929 (Levofloxacin)

3D MOL for HMDB0001929 (Levofloxacin)

3D SDF for HMDB0001929 (Levofloxacin)

3D-SDF for HMDB0001929 (Levofloxacin)

PDB for HMDB0001929 (Levofloxacin)

3D PDB for HMDB0001929 (Levofloxacin)

SMILES for HMDB0001929 (Levofloxacin)

INCHI for HMDB0001929 (Levofloxacin)

Structure for HMDB0001929 (Levofloxacin)

3D Structure for HMDB0001929 (Levofloxacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes