NP-MRD: Showing NP-Card for (2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0293574)

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Record Information

Version

2.0

Created at

2022-09-10 01:39:07 UTC

Updated at

2022-09-10 01:39:08 UTC

NP-MRD ID

NP0293574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

Cloxacillin, also known as MCIPC or orbenin, 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. Cloxacillin is a drug which is used to treat infections caused by penicillinase-producing staphylococci, including pneumococci, group a beta-hemolytic streptococci, and penicillin g-sensitive and penicillin g-resistant staphylococci. Cloxacillin is an extremely weak basic (essentially neutral) compound (based on its pKa). (2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Apis cerana. (2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 2005 (PMID: 16853954). A semisynthetic penicillin antibiotic carrying a 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido group at position 6 (PMID: 16540070) (PMID: 24858821) (PMID: 25305230).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -0.4863    1.5957   -2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    1.4296   -1.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175    1.9959   -2.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0015    1.6761   -1.8983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7290    0.8502   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6471    0.2744    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8534   -1.0790    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289   -1.6480    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4582   -0.8395    1.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2827    0.5301    1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917    1.0845    0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1780    2.8160    0.8652 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3305    0.6819   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620   -0.0882    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942   -0.8239    0.8477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -0.1455    0.1357 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.9678    1.1121 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3628   -0.1394    2.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.3478    3.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938   -0.1984    1.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    0.2731    0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6732    0.3849    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946    0.0414    2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000    0.8760    0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824   -0.5989   -0.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613   -1.6549   -0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    0.1466   -1.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -1.4642   -1.0365 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649   -1.4865    0.7495 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1105    2.2577   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    0.6364   -2.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107    2.1270   -3.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107   -1.7553   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8369   -2.7243    1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1557   -1.2573    2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8767    1.1299    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4513    0.4106   -0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1078   -1.6912    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990    1.3157    0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5561    0.3954    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4520   -2.6899   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7716   -1.5775   -0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -1.5337    0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620    0.4282   -1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1173   -0.5185   -2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    1.0292   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2402   -2.3497    1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 25  1  0
 25 26  1  0
 25 27  1  0
 25 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13  2  2  0
  2  1  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
 21 22  1  0
 22 24  1  0
 22 23  2  0
 20 29  1  0
  5 13  1  0
 11  6  1  0
 17 29  1  0
 29 47  1  1
 26 41  1  0
 26 42  1  0
 26 43  1  0
 27 44  1  0
 27 45  1  0
 27 46  1  0
 21 39  1  6
 17 38  1  1
 16 37  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
 24 40  1  0
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>
NP0293574

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

435.8810 Da

Monoisotopic Mass

435.06557 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015278

DrugBank ID

DB01147

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Dominguez-Ortega J, Martinez-Alonso JC, Marcos-Perez MC, Kindelan C, Frades A: Allergy to cloxacillin with normal tolerance to amoxicillin and cefuroxime. Allergol Immunopathol (Madr). 2006 Jan-Feb;34(1):37-8. doi: 10.1157/13084226. [PubMed:16540070 ]
Barbosa S, Taboada P, Mosquera V: Thermodynamic study of the effect of ethanol on two amphiphilic penicillins. J Phys Chem B. 2005 Dec 1;109(47):22692-8. doi: 10.1021/jp052631r. [PubMed:16853954 ]
Jonsson TB, Nilsson TK, Breimer LH, Schneede J, Arfvidsson B, Norgren L: Cloxacillin concentrations in serum, subcutaneous fat, and muscle in patients with chronic critical limb ischemia. Eur J Clin Pharmacol. 2014 Aug;70(8):957-63. doi: 10.1007/s00228-014-1695-9. Epub 2014 May 27. [PubMed:24858821 ]
Lewin R, Elander A, Thorarinsson A, Kolby L, Sahlin PE, Lundberg J, Panczel A, Liden M: A randomized prospective study of prophylactic cloxacillin in breast reduction surgery. Ann Plast Surg. 2015 Jan;74(1):17-21. doi: 10.1097/SAP.0000000000000352. [PubMed:25305230 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0293574)

MOL for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0293574 ((2s,5r,6r)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl](hydroxy)methylidene}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)