Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015278

Secondary Accession Numbers

HMDB15278

Metabolite Identification

Common Name

Cloxacillin

Description

Cloxacillin is only found in individuals that have used or taken this drug. It is a semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cloxacillin interferes with an autolysin inhibitor.

Structure

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

1147
  Mrv0541 02231215172D          

 30 33  0  0  1  0            999 V2000
    3.0617    3.1935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4193    0.0256    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -1.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222   -2.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4812   -2.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -0.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    1.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    0.3586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    1.9219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -0.2294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9042   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -1.3093    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8029   -0.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8029   -1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6742   -2.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    0.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988    1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885    3.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    2.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327    0.4227    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 15  2  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6 19  2  0  0  0  0
  7 10  1  0  0  0  0
  7 22  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
 14  9  1  1  0  0  0
  9 19  1  0  0  0  0
 10 21  2  0  0  0  0
 11 14  1  0  0  0  0
 11 30  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

HMDB0015278
     RDKit          3D
Cloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.5538   -0.3769   -2.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220   -0.3462   -2.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442   -0.3520   -3.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778   -0.3180   -2.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069   -0.2864   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790   -0.2570    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058    0.7777    0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    0.7564    2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.2885    2.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310   -1.3266    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589   -1.3128    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -2.6480   -0.8816 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -0.3060   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.3104    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -0.2724    1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -0.3522    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109   -0.3469    1.4075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6024   -1.4580    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.6538    1.9358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -0.6457    1.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811   -0.2013    0.7646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6774    0.4591    1.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141    0.5838    3.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9381    0.9780    1.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137    0.6586   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113   -0.1067   -1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101    1.7898   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.4128   -0.1278 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.5168    1.4452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0306    0.5493   -2.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915   -0.3965   -4.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -1.3165   -2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.6244    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936    1.5839    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0294   -0.2657    3.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -2.1626    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -0.3896   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.2518    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138   -1.0611    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3760    1.6961    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    0.5629   -2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -1.0699   -1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -0.3195   -1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.4801    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    1.4561   -0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4269   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    1.0864    2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 13  2  2  0
 29 17  1  0
 11  6  1  0
 29 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 16 37  1  0
 17 38  1  1
 21 39  1  6
 24 40  1  0
 26 41  1  0
 26 42  1  0
 26 43  1  0
 27 44  1  0
 27 45  1  0
 27 46  1  0
 29 47  1  1
M  END

1147
  Mrv0541 02231215172D          

 30 33  0  0  1  0            999 V2000
    3.0617    3.1935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.4193    0.0256    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -1.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222   -2.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4812   -2.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -0.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    1.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    0.3586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    1.9219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -0.2294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9042   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -1.3093    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8029   -0.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8029   -1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6742   -2.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    0.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    1.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988    1.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885    3.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    2.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327    0.4227    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 15  2  0  0  0  0
  4 18  1  0  0  0  0
  5 18  2  0  0  0  0
  6 19  2  0  0  0  0
  7 10  1  0  0  0  0
  7 22  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
 14  9  1  1  0  0  0
  9 19  1  0  0  0  0
 10 21  2  0  0  0  0
 11 14  1  0  0  0  0
 11 30  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015278

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1

> <INCHI_KEY>
LQOLIRLGBULYKD-JKIFEVAISA-N

> <FORMULA>
C19H18ClN3O5S

> <MOLECULAR_WEIGHT>
435.881

> <EXACT_MASS>
435.065569098

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.637534371820784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.301739658333334

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.646550253027858

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7497843753671107

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4133461786577338

> <JCHEM_POLAR_SURFACE_AREA>
112.74

> <JCHEM_REFRACTIVITY>
106.6371

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cloxacillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015278
     RDKit          3D
Cloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.5538   -0.3769   -2.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220   -0.3462   -2.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442   -0.3520   -3.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778   -0.3180   -2.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069   -0.2864   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790   -0.2570    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058    0.7777    0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    0.7564    2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.2885    2.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310   -1.3266    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589   -1.3128    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -2.6480   -0.8816 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -0.3060   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.3104    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -0.2724    1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -0.3522    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109   -0.3469    1.4075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6024   -1.4580    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.6538    1.9358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -0.6457    1.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811   -0.2013    0.7646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6774    0.4591    1.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141    0.5838    3.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9381    0.9780    1.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137    0.6586   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113   -0.1067   -1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101    1.7898   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.4128   -0.1278 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.5168    1.4452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0306    0.5493   -2.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915   -0.3965   -4.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -1.3165   -2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.6244    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936    1.5839    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0294   -0.2657    3.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -2.1626    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -0.3896   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.2518    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138   -1.0611    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3760    1.6961    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    0.5629   -2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -1.0699   -1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -0.3195   -1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.4801    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    1.4561   -0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4269   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    1.0864    2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 13  2  2  0
 29 17  1  0
 11  6  1  0
 29 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 16 37  1  0
 17 38  1  1
 21 39  1  6
 24 40  1  0
 26 41  1  0
 26 42  1  0
 26 43  1  0
 27 44  1  0
 27 45  1  0
 27 46  1  0
 29 47  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1147                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.715   5.961   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      11.983   0.048   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       7.879  -3.066   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.428  -5.053   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.965  -4.229   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.989  -1.213   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.086   2.501   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      10.518  -1.968   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.879   0.669   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.177   3.588   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.518  -0.428   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.888  -1.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.983  -2.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.965  -0.422   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.965  -1.974   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.134  -0.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.134  -2.103   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.459  -3.909   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.390   0.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.304   1.365   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.548   2.886   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.782   1.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.921   3.582   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -0.243   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.005   5.120   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.211   2.741   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.379   5.816   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.585   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.668   4.975   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      10.328   0.789   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   11   12                                                       
CONECT    3   15                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7   10   22                                                       
CONECT    8   11   13   15                                                  
CONECT    9   14   19                                                       
CONECT   10    7   21                                                       
CONECT   11    2    8   14   30                                             
CONECT   12    2   13   16   17                                             
CONECT   13    8   12   18                                                  
CONECT   14    9   11   15                                                  
CONECT   15    3    8   14                                                  
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    4    5   13                                                  
CONECT   19    6    9   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   10   20   23                                                  
CONECT   22    7   20   24                                                  
CONECT   23   21   25   26                                                  
CONECT   24   22                                                            
CONECT   25    1   23   27                                                  
CONECT   26   23   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
CONECT   30   11                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015278
HETATM    1  C1  UNL     1       0.554  -0.377  -2.997  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.922  -0.346  -2.429  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.044  -0.352  -3.133  1.00  0.00           O  
HETATM    4  N1  UNL     1       4.078  -0.318  -2.383  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.707  -0.286  -1.107  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.579  -0.257   0.066  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.606   0.778   0.968  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.487   0.756   2.045  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.360  -0.288   2.254  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.331  -1.327   1.347  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.459  -1.313   0.274  1.00  0.00           C  
HETATM   12 CL1  UNL     1       5.428  -2.648  -0.882  1.00  0.00          CL  
HETATM   13  C10 UNL     1       2.304  -0.306  -1.102  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.489  -0.310   0.092  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.096  -0.272   1.217  1.00  0.00           O  
HETATM   16  N2  UNL     1       0.101  -0.352   0.142  1.00  0.00           N  
HETATM   17  C12 UNL     1      -0.611  -0.347   1.408  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.602  -1.458   1.576  1.00  0.00           C  
HETATM   19  O3  UNL     1      -1.398  -2.654   1.936  1.00  0.00           O  
HETATM   20  N3  UNL     1      -2.703  -0.646   1.195  1.00  0.00           N  
HETATM   21  C14 UNL     1      -3.981  -0.201   0.765  1.00  0.00           C  
HETATM   22  C15 UNL     1      -4.677   0.459   1.883  1.00  0.00           C  
HETATM   23  O4  UNL     1      -4.214   0.584   3.035  1.00  0.00           O  
HETATM   24  O5  UNL     1      -5.938   0.978   1.633  1.00  0.00           O  
HETATM   25  C16 UNL     1      -3.814   0.659  -0.451  1.00  0.00           C  
HETATM   26  C17 UNL     1      -3.811  -0.107  -1.746  1.00  0.00           C  
HETATM   27  C18 UNL     1      -4.810   1.790  -0.526  1.00  0.00           C  
HETATM   28  S1  UNL     1      -2.168   1.413  -0.128  1.00  0.00           S  
HETATM   29  C19 UNL     1      -1.832   0.517   1.445  1.00  0.00           C  
HETATM   30  H1  UNL     1       0.031   0.549  -2.716  1.00  0.00           H  
HETATM   31  H2  UNL     1       0.691  -0.396  -4.132  1.00  0.00           H  
HETATM   32  H3  UNL     1       0.038  -1.317  -2.737  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.957   1.624   0.848  1.00  0.00           H  
HETATM   34  H5  UNL     1       5.494   1.584   2.747  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.029  -0.266   3.107  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.005  -2.163   1.484  1.00  0.00           H  
HETATM   37  H8  UNL     1      -0.487  -0.390  -0.697  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.028  -0.252   2.289  1.00  0.00           H  
HETATM   39  H10 UNL     1      -4.614  -1.061   0.462  1.00  0.00           H  
HETATM   40  H11 UNL     1      -6.376   1.696   2.175  1.00  0.00           H  
HETATM   41  H12 UNL     1      -3.455   0.563  -2.555  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.298  -1.070  -1.702  1.00  0.00           H  
HETATM   43  H14 UNL     1      -4.878  -0.320  -1.998  1.00  0.00           H  
HETATM   44  H15 UNL     1      -4.698   2.480   0.354  1.00  0.00           H  
HETATM   45  H16 UNL     1      -5.846   1.456  -0.667  1.00  0.00           H  
HETATM   46  H17 UNL     1      -4.548   2.427  -1.414  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.057   1.086   2.340  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   13   13
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   13
CONECT    6    7    7   11
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   37
CONECT   17   18   29   38
CONECT   18   19   19   20
CONECT   20   21   29
CONECT   21   22   25   39
CONECT   22   23   23   24
CONECT   24   40
CONECT   25   26   27   28
CONECT   26   41   42   43
CONECT   27   44   45   46
CONECT   28   29
CONECT   29   47
END

HMDB0015278
     RDKit          3D
Cloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.5538   -0.3769   -2.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220   -0.3462   -2.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0442   -0.3520   -3.1329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778   -0.3180   -2.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069   -0.2864   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790   -0.2570    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058    0.7777    0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    0.7564    2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.2885    2.2542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310   -1.3266    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589   -1.3128    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -2.6480   -0.8816 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3044   -0.3060   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.3104    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -0.2724    1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -0.3522    0.1423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6109   -0.3469    1.4075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6024   -1.4580    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -2.6538    1.9358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -0.6457    1.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811   -0.2013    0.7646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6774    0.4591    1.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141    0.5838    3.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9381    0.9780    1.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137    0.6586   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113   -0.1067   -1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8101    1.7898   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681    1.4128   -0.1278 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.5168    1.4452 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0306    0.5493   -2.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915   -0.3965   -4.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -1.3165   -2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.6244    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936    1.5839    2.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0294   -0.2657    3.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -2.1626    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -0.3896   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.2518    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138   -1.0611    0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3760    1.6961    2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    0.5629   -2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -1.0699   -1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776   -0.3195   -1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    2.4801    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8461    1.4561   -0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4269   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    1.0864    2.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 13  2  2  0
 29 17  1  0
 11  6  1  0
 29 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 16 37  1  0
 17 38  1  1
 21 39  1  6
 24 40  1  0
 26 41  1  0
 26 42  1  0
 26 43  1  0
 27 44  1  0
 27 45  1  0
 27 46  1  0
 29 47  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin	ChEBI
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid	ChEBI
Cloxacilina	ChEBI
Cloxacilline	ChEBI
Cloxacillinum	ChEBI
MCIPC	Kegg
Orbenin	Kegg
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanate	Generator
Cloxacillin sodium	HMDB
Chloroxacillin	HMDB
Tegopen	HMDB
Cloxacillin, sodium	HMDB
Syntarpen	HMDB
Sodium, cloxacillin	HMDB
Sodium cloxacillin	HMDB

Chemical Formula

C₁₉H₁₈ClN₃O₅S

Average Molecular Weight

435.881

Monoisotopic Molecular Weight

435.065569098

IUPAC Name

(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

cloxacillin

CAS Registry Number

61-72-3

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O

InChI Identifier

InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1

InChI Key

LQOLIRLGBULYKD-JKIFEVAISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Penam
Halobenzene
Chlorobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Tertiary carboxylic acid amide
Thiazolidine
Beta-lactam
Isoxazole
Lactam
Secondary carboxylic acid amide
Azetidine
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid
Dialkylthioether
Hemithioaminal
Thioether
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organohalogen compound
Organochloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:49566 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015278)

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	0.053 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.053 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.3	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-0.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.64 m³·mol⁻¹	ChemAxon
Polarizability	41.64 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-2H]-	224.756	30932474
DeepCCS	[M+Na]+	200.18	30932474
AllCCS	[M+H]+	194.1	32859911
AllCCS	[M+H-H2O]+	191.8	32859911
AllCCS	[M+NH4]+	196.1	32859911
AllCCS	[M+Na]+	196.7	32859911
AllCCS	[M-H]-	196.3	32859911
AllCCS	[M+Na-2H]-	196.4	32859911
AllCCS	[M+HCOO]-	196.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.48 minutes	32390414
Predicted by Siyang on May 30, 2022	13.574 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	83.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2259.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	605.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1017.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	524.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1465.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	281.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	142.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O	4615.1	Standard polar	33892256
Cloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O	2947.3	Standard non polar	33892256
Cloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O	3384.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cloxacillin,1TMS,isomer #1	CC1=C(C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)C(C2=CC=CC=C2Cl)=NO1	3307.8	Semi standard non polar	33892256
Cloxacillin,1TMS,isomer #2	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3312.3	Semi standard non polar	33892256
Cloxacillin,2TMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3279.3	Semi standard non polar	33892256
Cloxacillin,2TMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3150.0	Standard non polar	33892256
Cloxacillin,2TMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C)C(C2=CC=CC=C2Cl)=NO1	4091.7	Standard polar	33892256
Cloxacillin,1TBDMS,isomer #1	CC1=C(C(=O)N[C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)C(C2=CC=CC=C2Cl)=NO1	3508.2	Semi standard non polar	33892256
Cloxacillin,1TBDMS,isomer #2	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3484.9	Semi standard non polar	33892256
Cloxacillin,2TBDMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3618.5	Semi standard non polar	33892256
Cloxacillin,2TBDMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2Cl)=NO1	3582.7	Standard non polar	33892256
Cloxacillin,2TBDMS,isomer #1	CC1=C(C(=O)N([C@@H]2C(=O)N3[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]23)[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2Cl)=NO1	4195.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cloxacillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9442300000-e216b172b6089bc0b628	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cloxacillin GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9201100000-8c62d7bf4821412834e5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cloxacillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cloxacillin 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 - Cloxacillin LC-ESI-qTof , Positive-QTOF	splash10-03fr-0980100000-1acb1c4e617b9afd066c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cloxacillin LC-ESI-qTof , Positive-QTOF	splash10-03fr-0980100000-1acb1c4e617b9afd066c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cloxacillin LC-ESI-qTof , Positive-QTOF	splash10-03fr-0980100000-1acb1c4e617b9afd066c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cloxacillin , positive-QTOF	splash10-0a5a-0560910000-05dcf2cead0bc1f49482	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cloxacillin , positive-QTOF	splash10-01q9-1900000000-a2a9637ec3640b22d439	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 10V, Positive-QTOF	splash10-03g0-1981500000-b5aa89e8243c95661294	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 20V, Positive-QTOF	splash10-03mi-1980000000-5959a8cd3ff0d7b69e86	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 40V, Positive-QTOF	splash10-0900-4940000000-4f39d56cd5b7d76c29f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 10V, Negative-QTOF	splash10-0006-0092000000-f42335fd75afb22d0d5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 20V, Negative-QTOF	splash10-0006-0795000000-0f4a7aa6aa6b6709cf76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 40V, Negative-QTOF	splash10-0006-2920000000-e0da457c632e3e5d44da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 10V, Negative-QTOF	splash10-001i-1051900000-02e2b7b8281ef5861490	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 20V, Negative-QTOF	splash10-0006-9250100000-ed86f55f0155aa43591c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 40V, Negative-QTOF	splash10-001m-9632000000-a8ea4618ee5a92c98b3e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 10V, Positive-QTOF	splash10-000i-0110900000-7f26bb1ece4516994fc6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 20V, Positive-QTOF	splash10-022i-0590300000-7f87c7e79e0101a13c0d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cloxacillin 40V, Positive-QTOF	splash10-00dl-1950000000-43f0f287563f32d24bb4	2021-10-11	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 DB01147	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01147	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01147

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5873

KEGG Compound ID

C06923

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cloxacillin

METLIN ID

Not Available

PubChem Compound

6098

PDB ID

Not Available

ChEBI ID

49566

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

Transporters

Enzyme Details

1. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Enzyme Details

2. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Enzyme Details

3. 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

Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

Showing metabocard for Cloxacillin (HMDB0015278)

MOL for HMDB0015278 (Cloxacillin)

3D MOL for HMDB0015278 (Cloxacillin)

3D SDF for HMDB0015278 (Cloxacillin)

3D-SDF for HMDB0015278 (Cloxacillin)

PDB for HMDB0015278 (Cloxacillin)

3D PDB for HMDB0015278 (Cloxacillin)

SMILES for HMDB0015278 (Cloxacillin)

INCHI for HMDB0015278 (Cloxacillin)

Structure for HMDB0015278 (Cloxacillin)

3D Structure for HMDB0015278 (Cloxacillin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References

References

References