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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (6) Show 8 proteins XML

enzymes (2)transporters (6) Show 8 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014509

Secondary Accession Numbers

HMDB14509

Metabolite Identification

Common Name

Grepafloxacin

Description

Grepafloxacin 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. Grepafloxacin is a drug which is used for treatment of adults with mild to moderate infections caused by susceptible strains of haemophilus influenzae, streptococcus pneumoniae, or moraxella catarrhalis. Based on a literature review a significant number of articles have been published on Grepafloxacin.

Structure

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

365
  Mrv0541 02231214382D          

 26 29  0  0  1  0            999 V2000
    7.1488    1.4608    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.2092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -0.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5746   -1.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8239   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456   -1.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884   -0.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8649    0.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5778   -0.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884    1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    1.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8553   -2.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789    2.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 22  2  0  0  0  0
  3 26  1  0  0  0  0
  4 26  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 18  1  0  0  0  0
  7 17  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 16  2  0  0  0  0
 12 21  2  0  0  0  0
 13 20  2  0  0  0  0
 13 22  1  0  0  0  0
 14 16  1  0  0  0  0
 14 23  2  0  0  0  0
 15 17  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
M  END

HMDB0259429
     RDKit          3D
Grepafloxacin, (S)-
 48 51  0  0  0  0  0  0  0  0999 V2000
    1.5653   -3.5979   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -2.2317   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188   -1.9964   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -3.0414   -0.2853 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447   -0.7203    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -0.4852    0.2831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -1.1483    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3398   -1.3758    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887   -0.1371    0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.9365    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586    1.8987   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8010    0.4556   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    0.3081    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    0.0379    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -1.2334   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -1.4972   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -2.6484   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -0.4231   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342   -0.6799   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4432    0.2688   -0.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211   -1.9449   -0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    0.8226    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    1.0463    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    2.3765    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    3.2168   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991    3.5037   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -4.0577    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -4.2560   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283   -3.6915   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -0.4105    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367   -2.0675    1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -1.9238   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9858   -1.9594    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    0.1172    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    1.4650    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663    1.7647   -1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8599    1.6630   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.9415   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222    0.0772   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    1.3687   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795    1.3111    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.6771    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    1.6663    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6707    2.5719    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.8037   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039    3.9524   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    3.2138   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    4.4161    0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  5 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 15  2  1  0
 26 24  1  0
 12  6  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
 26 47  1  0
 26 48  1  0
M  END

365
  Mrv0541 02231214382D          

 26 29  0  0  1  0            999 V2000
    7.1488    1.4608    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.2092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1488   -0.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5746   -1.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8239   -1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456   -1.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884   -0.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8649    0.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5778   -0.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6884    1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359    1.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8553   -2.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789    2.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 22  2  0  0  0  0
  3 26  1  0  0  0  0
  4 26  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 18  1  0  0  0  0
  7 17  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 16  2  0  0  0  0
 12 21  2  0  0  0  0
 13 20  2  0  0  0  0
 13 22  1  0  0  0  0
 14 16  1  0  0  0  0
 14 23  2  0  0  0  0
 15 17  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014509

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)

> <INCHI_KEY>
AIJTTZAVMXIJGM-UHFFFAOYSA-N

> <FORMULA>
C19H22FN3O3

> <MOLECULAR_WEIGHT>
359.3947

> <EXACT_MASS>
359.16451979

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.692870910728004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
0.11811200672493903

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.876593176832228

> <JCHEM_PKA_STRONGEST_BASIC>
8.770720290866418

> <JCHEM_POLAR_SURFACE_AREA>
72.88

> <JCHEM_REFRACTIVITY>
97.39939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
grepafloxacin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259429
     RDKit          3D
Grepafloxacin, (S)-
 48 51  0  0  0  0  0  0  0  0999 V2000
    1.5653   -3.5979   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -2.2317   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188   -1.9964   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -3.0414   -0.2853 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447   -0.7203    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -0.4852    0.2831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -1.1483    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3398   -1.3758    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887   -0.1371    0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.9365    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586    1.8987   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8010    0.4556   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    0.3081    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    0.0379    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -1.2334   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -1.4972   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -2.6484   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -0.4231   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342   -0.6799   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4432    0.2688   -0.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211   -1.9449   -0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    0.8226    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    1.0463    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    2.3765    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    3.2168   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991    3.5037   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -4.0577    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -4.2560   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283   -3.6915   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -0.4105    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367   -2.0675    1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -1.9238   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9858   -1.9594    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    0.1172    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    1.4650    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663    1.7647   -1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8599    1.6630   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.9415   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222    0.0772   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    1.3687   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795    1.3111    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.6771    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    1.6663    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6707    2.5719    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.8037   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039    3.9524   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    3.2138   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    4.4161    0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  5 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 15  2  1  0
 26 24  1  0
 12  6  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
 26 47  1  0
 26 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 365                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0      13.344   2.727   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.908   4.229   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   1.919   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241   4.229   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.908  -0.391   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      13.344  -0.428   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      16.006  -1.978   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.908  -1.931   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.678  -3.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.138  -3.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242   0.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574   0.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242   1.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.014   0.347   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.338  -1.968   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.618  -0.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.669  -2.743   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.681   0.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.012  -0.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.618   2.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.574   1.919   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.908   2.689   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.014   1.952   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.663  -4.283   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.601   4.283   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.241   2.689   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   22                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5    8   11   12                                                  
CONECT    6   14   15   18                                                  
CONECT    7   17   19                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    8    9                                                       
CONECT   11    5   13   16                                                  
CONECT   12    5   21                                                       
CONECT   13   11   20   22                                                  
CONECT   14    6   16   23                                                  
CONECT   15    6   17                                                       
CONECT   16   11   14                                                       
CONECT   17    7   15   24                                                  
CONECT   18    6   19                                                       
CONECT   19    7   18                                                       
CONECT   20   13   23   25                                                  
CONECT   21   12   22   26                                                  
CONECT   22    2   13   21                                                  
CONECT   23    1   14   20                                                  
CONECT   24   17                                                            
CONECT   25   20                                                            
CONECT   26    3    4   21                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014509
HETATM    1  C1  UNL     1      -1.038  -3.315   1.449  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.748  -2.000   0.817  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.536  -1.548   0.624  1.00  0.00           C  
HETATM    4  F1  UNL     1       1.568  -2.321   1.013  1.00  0.00           F  
HETATM    5  C4  UNL     1       0.814  -0.321   0.035  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.143   0.113  -0.135  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.516   1.300  -0.865  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.661   0.876  -1.798  1.00  0.00           C  
HETATM    9  N2  UNL     1       4.797   0.425  -1.060  1.00  0.00           N  
HETATM   10  C7  UNL     1       4.543   0.212   0.331  1.00  0.00           C  
HETATM   11  C8  UNL     1       5.701  -0.646   0.858  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.273  -0.628   0.450  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.241   0.483  -0.376  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.533   0.045  -0.190  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.782  -1.173   0.395  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.090  -1.603   0.577  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.403  -2.697   1.101  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.153  -0.809   0.171  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.534  -1.248   0.356  1.00  0.00           C  
HETATM   20  O2  UNL     1      -5.757  -2.358   0.890  1.00  0.00           O  
HETATM   21  O3  UNL     1      -6.585  -0.472  -0.042  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.854   0.397  -0.407  1.00  0.00           C  
HETATM   23  N3  UNL     1      -2.559   0.795  -0.574  1.00  0.00           N  
HETATM   24  C17 UNL     1      -2.361   2.074  -1.190  1.00  0.00           C  
HETATM   25  C18 UNL     1      -1.852   3.247  -0.494  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.320   3.156  -0.657  1.00  0.00           C  
HETATM   27  H1  UNL     1      -1.520  -4.032   0.778  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.055  -3.798   1.733  1.00  0.00           H  
HETATM   29  H3  UNL     1      -1.556  -3.192   2.434  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.968   1.999  -0.129  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.739   1.757  -1.469  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.887   1.706  -2.491  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.312   0.018  -2.443  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.250  -0.435  -1.452  1.00  0.00           H  
HETATM   35  H9  UNL     1       4.484   1.140   0.919  1.00  0.00           H  
HETATM   36  H10 UNL     1       5.930  -0.405   1.913  1.00  0.00           H  
HETATM   37  H11 UNL     1       5.418  -1.701   0.777  1.00  0.00           H  
HETATM   38  H12 UNL     1       6.595  -0.451   0.253  1.00  0.00           H  
HETATM   39  H13 UNL     1       3.134  -0.784   1.542  1.00  0.00           H  
HETATM   40  H14 UNL     1       3.460  -1.581  -0.038  1.00  0.00           H  
HETATM   41  H15 UNL     1      -0.090   1.468  -0.846  1.00  0.00           H  
HETATM   42  H16 UNL     1      -7.158  -0.701  -0.869  1.00  0.00           H  
HETATM   43  H17 UNL     1      -4.663   1.029  -0.730  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.297   2.034  -2.296  1.00  0.00           H  
HETATM   45  H19 UNL     1      -1.446   3.228   0.534  1.00  0.00           H  
HETATM   46  H20 UNL     1      -1.359   4.033  -1.121  1.00  0.00           H  
HETATM   47  H21 UNL     1      -3.904   2.932   0.244  1.00  0.00           H  
HETATM   48  H22 UNL     1      -3.873   3.748  -1.412  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   15
CONECT    3    4    5
CONECT    5    6   13   13
CONECT    6    7   12
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34
CONECT   10   11   12   35
CONECT   11   36   37   38
CONECT   12   39   40
CONECT   13   14   41
CONECT   14   15   15   23
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   22   22
CONECT   19   20   20   21
CONECT   21   42
CONECT   22   23   43
CONECT   23   24
CONECT   24   25   26   44
CONECT   25   26   45   46
CONECT   26   47   48
END

HMDB0259429
     RDKit          3D
Grepafloxacin, (S)-
 48 51  0  0  0  0  0  0  0  0999 V2000
    1.5653   -3.5979   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -2.2317   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188   -1.9964   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -3.0414   -0.2853 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7447   -0.7203    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -0.4852    0.2831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -1.1483    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3398   -1.3758    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887   -0.1371    0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083    0.9365    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586    1.8987   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8010    0.4556   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    0.3081    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    0.0379    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -1.2334   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -1.4972   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -2.6484   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -0.4231   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342   -0.6799   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4432    0.2688   -0.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211   -1.9449   -0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    0.8226    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    1.0463    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    2.3765    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644    3.2168   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991    3.5037   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -4.0577    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -4.2560   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283   -3.6915   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -0.4105    2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367   -2.0675    1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -1.9238   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9858   -1.9594    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059    0.1172    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    1.4650    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663    1.7647   -1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8599    1.6630   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    2.9415   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222    0.0772   -1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    1.3687   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795    1.3111    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.6771    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664    1.6663    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6707    2.5719    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    2.8037   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5039    3.9524   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170    3.2138   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    4.4161    0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  5 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 15  2  1  0
 26 24  1  0
 12  6  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
 26 47  1  0
 26 48  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Raxar	ChEMBL, HMDB
Grepafloxacin hydrochloride	MeSH, HMDB
Grepafloxacin HCL	MeSH, HMDB
(+--)-1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid	MeSH, HMDB
(+--)-1-Cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid monohydrochloride	MeSH, HMDB

Chemical Formula

C₁₉H₂₂FN₃O₃

Average Molecular Weight

359.3947

Monoisotopic Molecular Weight

359.16451979

IUPAC Name

1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

grepafloxacin

CAS Registry Number

119914-60-2

SMILES

CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O

InChI Identifier

InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)

InChI Key

AIJTTZAVMXIJGM-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
Aryl fluoride
Aryl halide
1,4-diazinane
Piperazine
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Tertiary amine
Azacycle
Secondary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Secondary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:5543 )
quinolone antibiotic (CHEBI:5543 )
fluoroquinolone antibiotic (CHEBI:5543 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.63 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	0.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.88	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	37.69 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
DeepCCS	[M+H]+	191.637	30932474
DeepCCS	[M-H]-	189.279	30932474
DeepCCS	[M-2H]-	223.501	30932474
DeepCCS	[M+Na]+	198.853	30932474
AllCCS	[M+H]+	184.4	32859911
AllCCS	[M+H-H2O]+	181.5	32859911
AllCCS	[M+NH4]+	187.0	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	186.2	32859911
AllCCS	[M+Na-2H]-	186.0	32859911
AllCCS	[M+HCOO]-	186.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Grepafloxacin	CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O	3580.3	Standard polar	33892256
Grepafloxacin	CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O	2740.3	Standard non polar	33892256
Grepafloxacin	CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O	3615.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grepafloxacin,1TMS,isomer #1	CC1=C(F)C(N2CCNC(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C)=CN2C1CC1	3461.0	Semi standard non polar	33892256
Grepafloxacin,1TMS,isomer #2	CC1=C(F)C(N2CCN([Si](C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O)=CN2C1CC1	3424.8	Semi standard non polar	33892256
Grepafloxacin,2TMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C)=CN2C1CC1	3389.9	Semi standard non polar	33892256
Grepafloxacin,2TMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C)=CN2C1CC1	3147.6	Standard non polar	33892256
Grepafloxacin,2TMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C)=CN2C1CC1	3598.4	Standard polar	33892256
Grepafloxacin,1TBDMS,isomer #1	CC1=C(F)C(N2CCNC(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN2C1CC1	3641.7	Semi standard non polar	33892256
Grepafloxacin,1TBDMS,isomer #2	CC1=C(F)C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O)=CN2C1CC1	3675.7	Semi standard non polar	33892256
Grepafloxacin,2TBDMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN2C1CC1	3817.3	Semi standard non polar	33892256
Grepafloxacin,2TBDMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN2C1CC1	3548.6	Standard non polar	33892256
Grepafloxacin,2TBDMS,isomer #1	CC1=C(F)C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)=CC2=C1C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN2C1CC1	3777.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr6-1029000000-706de57181850354ad84	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (1 TMS) - 70eV, Positive	splash10-014l-4009700000-5f8c566ab4608e488a1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grepafloxacin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 10V, Positive-QTOF	splash10-03di-0009000000-2f5a30d953de1f736ea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 20V, Positive-QTOF	splash10-01ox-7029000000-5092d7ae0d6cd5b524bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 40V, Positive-QTOF	splash10-0006-9030000000-c160b8ef525b23358374	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 10V, Negative-QTOF	splash10-08fr-0009000000-21915b34d4523001f7f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 20V, Negative-QTOF	splash10-03di-2079000000-ac0604da9e8b550b1711	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 40V, Negative-QTOF	splash10-0a4i-9040000000-825d27f7dab3d78603bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 10V, Negative-QTOF	splash10-0a4i-0009000000-714280bbcfde93aa7b44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 20V, Negative-QTOF	splash10-0a4i-0019000000-5e38035e60ddc6c31a50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 40V, Negative-QTOF	splash10-0a4i-1098000000-13c3d9c32132c12b9af2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 10V, Positive-QTOF	splash10-03di-0009000000-eb6c80e8b1d8eb060c07	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 20V, Positive-QTOF	splash10-0006-0009000000-d1bdf823b553634a98a3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grepafloxacin 40V, Positive-QTOF	splash10-0a6r-1094000000-f623c32b7e5523cef0dc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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 DB00365	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00365	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00365

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

65391

KEGG Compound ID

C11368

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Grepafloxacin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Pal D, Mitra AK: MDR- and CYP3A4-mediated drug-drug interactions. J Neuroimmune Pharmacol. 2006 Sep;1(3):323-39. Epub 2006 Aug 2. [PubMed:18040809 ]
Owens RC Jr: QT prolongation with antimicrobial agents: understanding the significance. Drugs. 2004;64(10):1091-124. [PubMed:15139788 ]

Enzyme Details

2. 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

Rodighiero V: Effects of liver disease on pharmacokinetics. An update. Clin Pharmacokinet. 1999 Nov;37(5):399-431. [PubMed:10589374 ]
Bril F, Gonzalez CD, Di Girolamo G: Antimicrobial agents-associated with QT interval prolongation. Curr Drug Saf. 2010 Jan;5(1):85-92. [PubMed:20210724 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]

Enzyme Details

2. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Sasabe H, Tsuji A, Sugiyama Y: Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther. 1998 Mar;284(3):1033-9. [PubMed:9495864 ]

Enzyme Details

3. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Tamai I, Yamashita J, Kido Y, Ohnari A, Sai Y, Shima Y, Naruhashi K, Koizumi S, Tsuji A: Limited distribution of new quinolone antibacterial agents into brain caused by multiple efflux transporters at the blood-brain barrier. J Pharmacol Exp Ther. 2000 Oct;295(1):146-52. [PubMed:10991972 ]

Enzyme Details

4. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Yamaguchi H, Yano I, Hashimoto Y, Inui KI: Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther. 2000 Oct;295(1):360-6. [PubMed:10992002 ]
Naruhashi K, Tamai I, Inoue N, Muraoka H, Sai Y, Suzuki N, Tsuji A: Active intestinal secretion of new quinolone antimicrobials and the partial contribution of P-glycoprotein. J Pharm Pharmacol. 2001 May;53(5):699-709. [PubMed:11370709 ]
Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [PubMed:15032316 ]

Enzyme Details

5. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]

Enzyme Details

6. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. [PubMed:9827570 ]

Showing metabocard for Grepafloxacin (HMDB0014509)

MOL for HMDB0014509 (Grepafloxacin)

3D MOL for HMDB0014509 (Grepafloxacin)

3D SDF for HMDB0014509 (Grepafloxacin)

3D-SDF for HMDB0014509 (Grepafloxacin)

PDB for HMDB0014509 (Grepafloxacin)

3D PDB for HMDB0014509 (Grepafloxacin)

SMILES for HMDB0014509 (Grepafloxacin)

INCHI for HMDB0014509 (Grepafloxacin)

Structure for HMDB0014509 (Grepafloxacin)

3D Structure for HMDB0014509 (Grepafloxacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Transporters

References

References

References

References

References

References