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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014851

Secondary Accession Numbers

HMDB14851

Metabolite Identification

Common Name

Oxacillin

Description

Oxacillin is only found in individuals that have used or taken this drug. It is an antibiotic similar to flucloxacillin used in resistant staphylococci infections. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin 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 Oxacillin interferes with an autolysin inhibitor.

Structure

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

713
  Mrv0541 02231214572D          

 29 32  0  0  1  0            999 V2000
    6.4193    0.0644    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -1.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222   -2.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4812   -2.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -0.6108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    1.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -1.0155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    0.3975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    1.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -0.1905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9042   -0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -1.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8029   -0.1870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8029   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6742   -2.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261    0.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    1.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988    1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885    3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327    0.4616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 14  2  0  0  0  0
  3 17  1  0  0  0  0
  4 17  2  0  0  0  0
  5 18  2  0  0  0  0
  6  9  1  0  0  0  0
  6 21  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  0  0  0  0
 13  8  1  1  0  0  0
  8 18  1  0  0  0  0
  9 20  2  0  0  0  0
 10 13  1  0  0  0  0
 10 29  1  6  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  6  0  0  0
 13 14  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014851
     RDKit          3D
Oxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.2737    2.9754    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    2.4692    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    3.2386    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480    2.5413    0.4547 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    1.2312    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4758    0.1077    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317    0.0002    1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   -0.9960    1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3991   -1.9505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702   -1.8761   -0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -0.8554   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1611    1.1793    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968   -0.0403    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.1309    0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.0861   -0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.3984   -0.3476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3515   -1.5053   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.8359   -2.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.0899   -0.9787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.5721   -0.7464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7733   -1.6743   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -1.4606   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -2.9669   -0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    0.5391    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.8719   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.6793    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.0684    1.3206 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.5022    0.2776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2944    2.4144    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476    4.0204    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    3.0614   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    0.7403    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -1.0202    2.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1347   -2.7502    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5107   -2.6366   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8203   -0.8049   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4669    0.7762   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -2.2322   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2628   -0.1362   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -3.7368    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    2.4310    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583    2.5468   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479    1.7652   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268    1.6157    1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9400    0.8039    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558   -0.2094    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -2.4729    0.6704 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
  5 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 12  2  2  0
 28 16  1  0
 11  6  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  1
 20 39  1  6
 23 40  1  0
 25 41  1  0
 25 42  1  0
 25 43  1  0
 26 44  1  0
 26 45  1  0
 26 46  1  0
 28 47  1  1
M  END

713
  Mrv0541 02231214572D          

 29 32  0  0  1  0            999 V2000
    6.4193    0.0644    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -1.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222   -2.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4812   -2.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -0.6108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    1.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -1.0155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207    0.3975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    1.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -0.1905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9042   -0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4193   -1.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8029   -0.1870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8029   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717   -1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6742   -2.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4234    0.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261    0.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    1.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526    2.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988    1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885    3.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327    0.4616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 14  2  0  0  0  0
  3 17  1  0  0  0  0
  4 17  2  0  0  0  0
  5 18  2  0  0  0  0
  6  9  1  0  0  0  0
  6 21  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  0  0  0  0
 13  8  1  1  0  0  0
  8 18  1  0  0  0  0
  9 20  2  0  0  0  0
 10 13  1  0  0  0  0
 10 29  1  6  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  6  0  0  0
 13 14  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014851

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

> <INCHI_KEY>
UWYHMGVUTGAWSP-JKIFEVAISA-N

> <FORMULA>
C19H19N3O5S

> <MOLECULAR_WEIGHT>
401.436

> <EXACT_MASS>
401.104541423

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.60884583075184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.6976949820000002

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.650808618295354

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.750966590256605

> <JCHEM_PKA_STRONGEST_BASIC>
-0.11723067800138864

> <JCHEM_POLAR_SURFACE_AREA>
112.74

> <JCHEM_REFRACTIVITY>
101.83230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxacillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014851
     RDKit          3D
Oxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.2737    2.9754    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    2.4692    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    3.2386    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480    2.5413    0.4547 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    1.2312    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4758    0.1077    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317    0.0002    1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   -0.9960    1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3991   -1.9505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702   -1.8761   -0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -0.8554   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1611    1.1793    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968   -0.0403    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.1309    0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.0861   -0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.3984   -0.3476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3515   -1.5053   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.8359   -2.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.0899   -0.9787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.5721   -0.7464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7733   -1.6743   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -1.4606   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -2.9669   -0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    0.5391    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.8719   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.6793    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.0684    1.3206 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.5022    0.2776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2944    2.4144    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476    4.0204    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    3.0614   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    0.7403    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -1.0202    2.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1347   -2.7502    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5107   -2.6366   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8203   -0.8049   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4669    0.7762   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -2.2322   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2628   -0.1362   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -3.7368    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    2.4310    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583    2.5468   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479    1.7652   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268    1.6157    1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9400    0.8039    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558   -0.2094    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -2.4729    0.6704 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
  5 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 12  2  2  0
 28 16  1  0
 11  6  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  1
 20 39  1  6
 23 40  1  0
 25 41  1  0
 25 42  1  0
 25 43  1  0
 26 44  1  0
 26 45  1  0
 26 46  1  0
 28 47  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 713                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.983   0.120   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.879  -2.993   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.428  -4.981   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.965  -4.156   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.989  -1.140   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.086   2.574   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      10.518  -1.896   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.879   0.742   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.177   3.660   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.518  -0.356   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.888  -1.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.983  -2.371   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.965  -0.349   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.965  -1.902   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.134  -0.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.134  -2.031   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.459  -3.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.390   0.346   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.304   1.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.548   2.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.782   1.200   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.921   3.655   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -0.171   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.005   5.192   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.211   2.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.379   5.889   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.585   3.510   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.668   5.047   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      10.328   0.862   0.000  0.00  0.00           H+0
CONECT    1   10   11                                                       
CONECT    2   14                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6    9   21                                                       
CONECT    7   10   12   14                                                  
CONECT    8   13   18                                                       
CONECT    9    6   20                                                       
CONECT   10    1    7   13   29                                             
CONECT   11    1   12   15   16                                             
CONECT   12    7   11   17                                                  
CONECT   13    8   10   14                                                  
CONECT   14    2    7   13                                                  
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    3    4   12                                                  
CONECT   18    5    8   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20    9   19   22                                                  
CONECT   21    6   19   23                                                  
CONECT   22   20   24   25                                                  
CONECT   23   21                                                            
CONECT   24   22   26                                                       
CONECT   25   22   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   28                                                       
CONECT   28   26   27                                                       
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0014851
HETATM    1  C1  UNL     1       0.274   2.975   0.368  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.686   2.469   0.372  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.770   3.239   0.476  1.00  0.00           O  
HETATM    4  N1  UNL     1       3.848   2.541   0.455  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.563   1.231   0.331  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.476   0.108   0.280  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.432   0.000   1.297  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.361  -0.996   1.340  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.399  -1.951   0.373  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.470  -1.876  -0.648  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.523  -0.855  -0.687  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.161   1.179   0.279  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.397  -0.040   0.139  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.010  -1.131   0.398  1.00  0.00           O  
HETATM   15  N2  UNL     1       0.043  -0.086  -0.261  1.00  0.00           N  
HETATM   16  C12 UNL     1      -0.584  -1.398  -0.348  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.351  -1.505  -1.601  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.060  -1.836  -2.773  1.00  0.00           O  
HETATM   19  N3  UNL     1      -2.555  -1.090  -0.979  1.00  0.00           N  
HETATM   20  C14 UNL     1      -3.886  -0.572  -0.746  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.773  -1.674  -0.373  1.00  0.00           C  
HETATM   22  O4  UNL     1      -5.982  -1.461  -0.142  1.00  0.00           O  
HETATM   23  O5  UNL     1      -4.302  -2.967  -0.268  1.00  0.00           O  
HETATM   24  C16 UNL     1      -3.777   0.539   0.243  1.00  0.00           C  
HETATM   25  C17 UNL     1      -3.452   1.872  -0.353  1.00  0.00           C  
HETATM   26  C18 UNL     1      -5.052   0.679   1.038  1.00  0.00           C  
HETATM   27  S1  UNL     1      -2.419  -0.068   1.321  1.00  0.00           S  
HETATM   28  C19 UNL     1      -1.944  -1.502   0.278  1.00  0.00           C  
HETATM   29  H1  UNL     1      -0.294   2.414   1.124  1.00  0.00           H  
HETATM   30  H2  UNL     1       0.348   4.020   0.835  1.00  0.00           H  
HETATM   31  H3  UNL     1      -0.164   3.061  -0.625  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.430   0.740   2.080  1.00  0.00           H  
HETATM   33  H5  UNL     1       7.082  -1.020   2.167  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.135  -2.750   0.397  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.511  -2.637  -1.406  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.820  -0.805  -1.502  1.00  0.00           H  
HETATM   37  H9  UNL     1      -0.467   0.776  -0.490  1.00  0.00           H  
HETATM   38  H10 UNL     1       0.068  -2.232  -0.089  1.00  0.00           H  
HETATM   39  H11 UNL     1      -4.263  -0.136  -1.694  1.00  0.00           H  
HETATM   40  H12 UNL     1      -4.830  -3.737   0.106  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.699   2.431   0.265  1.00  0.00           H  
HETATM   42  H14 UNL     1      -4.358   2.547  -0.349  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.148   1.765  -1.395  1.00  0.00           H  
HETATM   44  H16 UNL     1      -5.027   1.616   1.661  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.940   0.804   0.389  1.00  0.00           H  
HETATM   46  H18 UNL     1      -5.256  -0.209   1.685  1.00  0.00           H  
HETATM   47  H19 UNL     1      -2.222  -2.473   0.670  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   12   12
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   32
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   36
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   37
CONECT   16   17   28   38
CONECT   17   18   18   19
CONECT   19   20   28
CONECT   20   21   24   39
CONECT   21   22   22   23
CONECT   23   40
CONECT   24   25   26   27
CONECT   25   41   42   43
CONECT   26   44   45   46
CONECT   27   28
CONECT   28   47
END

HMDB0014851
     RDKit          3D
Oxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    0.2737    2.9754    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859    2.4692    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699    3.2386    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480    2.5413    0.4547 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    1.2312    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4758    0.1077    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317    0.0002    1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   -0.9960    1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3991   -1.9505    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702   -1.8761   -0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -0.8554   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1611    1.1793    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968   -0.0403    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -1.1309    0.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.0861   -0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.3984   -0.3476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3515   -1.5053   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0603   -1.8359   -2.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.0899   -0.9787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.5721   -0.7464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7733   -1.6743   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -1.4606   -0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -2.9669   -0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    0.5391    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.8719   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.6793    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.0684    1.3206 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440   -1.5022    0.2776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2944    2.4144    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476    4.0204    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    3.0614   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    0.7403    2.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -1.0202    2.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1347   -2.7502    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5107   -2.6366   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8203   -0.8049   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4669    0.7762   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -2.2322   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2628   -0.1362   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -3.7368    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    2.4310    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583    2.5468   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479    1.7652   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268    1.6157    1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9400    0.8039    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558   -0.2094    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -2.4729    0.6704 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
  5 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 12  2  2  0
 28 16  1  0
 11  6  1  0
 28 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  1
 20 39  1  6
 23 40  1  0
 25 41  1  0
 25 42  1  0
 25 43  1  0
 26 44  1  0
 26 45  1  0
 26 46  1  0
 28 47  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(5-Methyl-3-phenyl-4-isoxazolyl)penicillin	ChEBI
5-Methyl-3-phenyl-4-isoxazolyl-penicillin	ChEBI
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid	ChEBI
Oxazocillin	ChEBI
Oxacilina	Kegg
(2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid	Generator
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanate	Generator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid	Generator
Oxacillin sodium	HMDB
Oxacillin, monosodium salt, anhydrous	HMDB
Oxazocilline	HMDB
Penicillin, methylphenylisoxazolyl	HMDB
Prostaphlin	HMDB
Methylphenylisoxazolyl penicillin	HMDB
Oxacillin, sodium	HMDB
Sodium oxacillin	HMDB
Oxacillin, monosodium salt, monohydrate	HMDB
Sodium, oxacillin	HMDB

Chemical Formula

C₁₉H₁₉N₃O₅S

Average Molecular Weight

401.436

Monoisotopic Molecular Weight

401.104541423

IUPAC Name

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

Traditional Name

oxacillin

CAS Registry Number

66-79-5

SMILES

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

InChI Identifier

InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

InChI Key

UWYHMGVUTGAWSP-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
Benzenoid
Monocyclic benzene moiety
Isoxazole
Tertiary carboxylic acid amide
Azole
Thiazolidine
Heteroaromatic compound
Beta-lactam
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azetidine
Oxacycle
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:7809 )

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

Cytoplasm (HMDB: HMDB0014851)
Membrane (HMDB: HMDB0014851)

Source

Exogenous

Exogenous (HMDB: HMDB0014851)

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	0.086 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	189.001	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001277

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.7	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-0.12	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	101.83 m³·mol⁻¹	ChemAxon
Polarizability	39.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.763	31661259
DarkChem	[M-H]-	179.639	31661259
DeepCCS	[M-2H]-	220.28	30932474
DeepCCS	[M+Na]+	195.705	30932474
AllCCS	[M+H]+	190.5	32859911
AllCCS	[M+H-H2O]+	188.0	32859911
AllCCS	[M+NH4]+	192.7	32859911
AllCCS	[M+Na]+	193.3	32859911
AllCCS	[M-H]-	192.8	32859911
AllCCS	[M+Na-2H]-	192.8	32859911
AllCCS	[M+HCOO]-	192.8	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.	5.37 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9763 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2323.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.6 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	559.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	973.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	494.4 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	1438.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	280.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	150.3 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	66.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O	4467.3	Standard polar	33892256
Oxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O	2930.1	Standard non polar	33892256
Oxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O	3301.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxacillin,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=C2)=NO1	3230.8	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3219.7	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3167.4	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3045.5	Standard non polar	33892256
Oxacillin,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=C2)=NO1	3893.2	Standard polar	33892256
Oxacillin,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=C2)=NO1	3437.1	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3414.8	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3527.6	Semi standard non polar	33892256
Oxacillin,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=C2)=NO1	3469.2	Standard non polar	33892256
Oxacillin,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=C2)=NO1	4054.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxacillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9756000000-f6bf977e3f72e4a53daf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxacillin GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9422200000-f8a5f80c92e02cdcee18	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxacillin 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 - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-0a4i-0090000000-79c009ac45201875c809	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-0a4i-1290000000-4d46550a2c9c9f77458a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-00di-8890000000-4a47690fda1171ea9191	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-00e9-9530000000-81bb9ec609f6a7e8c6dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-00e9-9410000000-b5c01a94c4b433924722	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-00e9-9200000000-4bfc7a848a77bc668c0a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-01b9-9000000000-927fa2d2be3c33adb44c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-3661f69f0fee17d6a499	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-f568ba02b1720f9fd951	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-03dl-0980000000-62551643a67b5e9a21f8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-03dl-0920000000-69978fc6eeaa10c71f81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-92b22bc2f96b5f612718	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-03di-1900000000-4dceea173f6174da433d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-03di-3900000000-3ee73f5cb610870dbdb1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-0ikj-9800000000-fbc9b294222787b35a80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-0k92-9200000000-a405a812cf5f1a2f17e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-0udj-9100000000-451b59b916ee627de317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin LC-ESI-QFT , positive-QTOF	splash10-0udi-9000000000-21eb1aa369a09320f715	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxacillin 45V, Negative-QTOF	splash10-00di-8890000000-be778bbb3e94437c3383	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 10V, Positive-QTOF	splash10-0ikc-1972400000-1b4711e093e9f42ab804	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 20V, Positive-QTOF	splash10-03du-1930000000-b12c4b362713b4bb04cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 40V, Positive-QTOF	splash10-0903-3910000000-8b5cc5bea864dcaf596d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 10V, Negative-QTOF	splash10-0a4i-0091000000-b65dbdc0c5b20e629677	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 20V, Negative-QTOF	splash10-0a4i-0692000000-6c32b8616abd8c887bd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxacillin 40V, Negative-QTOF	splash10-0a4i-1910000000-2ad85244337188941840	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00713	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00713	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00713

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5961

KEGG Compound ID

C07334

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxacillin

METLIN ID

Not Available

PubChem Compound

6196

PDB ID

Not Available

ChEBI ID

7809

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 ]

Showing metabocard for Oxacillin (HMDB0014851)

MOL for HMDB0014851 (Oxacillin)

3D MOL for HMDB0014851 (Oxacillin)

3D SDF for HMDB0014851 (Oxacillin)

3D-SDF for HMDB0014851 (Oxacillin)

PDB for HMDB0014851 (Oxacillin)

3D PDB for HMDB0014851 (Oxacillin)

SMILES for HMDB0014851 (Oxacillin)

INCHI for HMDB0014851 (Oxacillin)

Structure for HMDB0014851 (Oxacillin)

3D Structure for HMDB0014851 (Oxacillin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References

References