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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014446

Secondary Accession Numbers

HMDB14446

Metabolite Identification

Common Name

Flucloxacillin

Description

Flucloxacillin is only found in individuals that have used or taken this drug. It is an antibiotic analog of cloxacillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, flucloxacillin 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 flucloxacillin interferes with an autolysin inhibitor.

Structure

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

301
  Mrv0541 02231214352D          

 31 34  0  0  1  0            999 V2000
    3.8529   -0.4082    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1633    0.6613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014    1.9919    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646   -1.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8661   -2.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2251   -1.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815    2.5577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646    0.9944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970    1.9756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    0.4064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6481   -0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1633   -0.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5468    0.4099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5468   -0.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3156    0.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3156   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4182   -1.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673    0.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851    1.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699    1.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158    2.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772    0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4517    2.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1186   -0.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    1.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -0.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915   -0.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2767    1.0585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3 27  1  0  0  0  0
  4 16  2  0  0  0  0
  5 19  1  0  0  0  0
  6 19  2  0  0  0  0
  7 20  2  0  0  0  0
  8 11  1  0  0  0  0
  8 23  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
 15 10  1  1  0  0  0
 10 20  1  0  0  0  0
 11 22  2  0  0  0  0
 12 15  1  0  0  0  0
 12 31  1  6  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

HMDB0014446
     RDKit          3D
Flucloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.2771   -3.4627    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716   -3.4316    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996   -4.4516   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -4.1315   -1.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -2.7783   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -2.0965   -1.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323   -1.4400   -2.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -1.4512   -3.2964 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -0.8011   -3.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581   -0.7764   -3.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -1.4378   -2.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -2.0802   -1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -2.9127    0.1144 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -2.3389   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.9431    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432   -0.6222    0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -0.0147    0.4094 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    1.3401    0.7774 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3389    1.6545    2.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0424    1.5487    3.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    2.0795    1.8857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    2.4601    1.9281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4488    3.9010    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    4.6042    1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717    4.4979    1.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.5299    1.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4046    1.9780    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    0.1944    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8728    1.3495   -0.3286 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101    2.2081    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1898   -3.6161    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3651   -2.5868    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -4.3564    1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -0.2979   -4.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.2779   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -1.4261   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.4052    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    1.8858    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    2.3525    2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7093    5.3907    0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    2.6452   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    2.5814    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    1.1241    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.3936    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.3690    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6553    0.3449    2.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    3.2290    0.1529 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 14  2  2  0
 30 18  1  0
 12  6  1  0
 30 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 17 37  1  0
 18 38  1  6
 22 39  1  1
 25 40  1  0
 27 41  1  0
 27 42  1  0
 27 43  1  0
 28 44  1  0
 28 45  1  0
 28 46  1  0
 30 47  1  6
M  END

301
  Mrv0541 02231214352D          

 31 34  0  0  1  0            999 V2000
    3.8529   -0.4082    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1633    0.6613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014    1.9919    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646   -1.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8661   -2.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2251   -1.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9521   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815    2.5577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646    0.9944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970    1.9756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    0.4064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6481   -0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1633   -0.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5468    0.4099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5468   -0.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3156    0.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3156   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4182   -1.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673    0.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851    1.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699    1.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158    2.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772    0.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4517    2.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1186   -0.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    1.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -0.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915   -0.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2767    1.0585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3 27  1  0  0  0  0
  4 16  2  0  0  0  0
  5 19  1  0  0  0  0
  6 19  2  0  0  0  0
  7 20  2  0  0  0  0
  8 11  1  0  0  0  0
  8 23  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
 15 10  1  1  0  0  0
 10 20  1  0  0  0  0
 11 22  2  0  0  0  0
 12 15  1  0  0  0  0
 12 31  1  6  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014446

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1

> <INCHI_KEY>
UIOFUWFRIANQPC-JKIFEVAISA-N

> <FORMULA>
C19H17ClFN3O5S

> <MOLECULAR_WEIGHT>
453.872

> <EXACT_MASS>
453.056147271

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.690961987456426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-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>
2.69

> <JCHEM_LOGP>
2.444441594666667

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.638424587889514

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7475461225499553

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9312708633797547

> <JCHEM_POLAR_SURFACE_AREA>
112.74

> <JCHEM_REFRACTIVITY>
106.85350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flucloxacillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014446
     RDKit          3D
Flucloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.2771   -3.4627    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716   -3.4316    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996   -4.4516   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -4.1315   -1.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -2.7783   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -2.0965   -1.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323   -1.4400   -2.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -1.4512   -3.2964 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -0.8011   -3.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581   -0.7764   -3.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -1.4378   -2.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -2.0802   -1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -2.9127    0.1144 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -2.3389   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.9431    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432   -0.6222    0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -0.0147    0.4094 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    1.3401    0.7774 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3389    1.6545    2.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0424    1.5487    3.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    2.0795    1.8857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    2.4601    1.9281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4488    3.9010    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    4.6042    1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717    4.4979    1.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.5299    1.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4046    1.9780    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    0.1944    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8728    1.3495   -0.3286 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101    2.2081    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1898   -3.6161    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3651   -2.5868    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -4.3564    1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -0.2979   -4.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.2779   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -1.4261   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.4052    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    1.8858    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    2.3525    2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7093    5.3907    0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    2.6452   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    2.5814    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    1.1241    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.3936    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.3690    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6553    0.3449    2.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    3.2290    0.1529 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 14  2  2  0
 30 18  1  0
 12  6  1  0
 30 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 17 37  1  0
 18 38  1  6
 22 39  1  1
 25 40  1  0
 27 41  1  0
 27 42  1  0
 27 43  1  0
 28 44  1  0
 28 45  1  0
 28 46  1  0
 30 47  1  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 301                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       7.192  -0.762   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      15.238   1.234   0.000  0.00  0.00           S+0
HETATM    3  F   UNK     0       4.296   3.718   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0      11.134  -1.879   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.683  -3.866   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      17.220  -3.042   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.244  -0.026   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.432   4.774   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      13.773  -0.781   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      11.134   1.856   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       6.341   3.688   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      13.773   0.759   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.143  -0.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.238  -1.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.221   0.765   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.221  -0.788   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.389   0.894   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.389  -0.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.714  -2.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.646   1.461   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.559   2.552   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.037   2.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.803   4.072   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.744   1.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.177   4.769   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.821  -0.060   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.373   2.180   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.528  -0.896   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080   1.344   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.157  -0.194   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      13.583   1.976   0.000  0.00  0.00           H+0
CONECT    1   26                                                            
CONECT    2   12   13                                                       
CONECT    3   27                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6   19                                                            
CONECT    7   20                                                            
CONECT    8   11   23                                                       
CONECT    9   12   14   16                                                  
CONECT   10   15   20                                                       
CONECT   11    8   22                                                       
CONECT   12    2    9   15   31                                             
CONECT   13    2   14   17   18                                             
CONECT   14    9   13   19                                                  
CONECT   15   10   12   16                                                  
CONECT   16    4    9   15                                                  
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19    5    6   14                                                  
CONECT   20    7   10   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   11   21   24                                                  
CONECT   23    8   21   25                                                  
CONECT   24   22   26   27                                                  
CONECT   25   23                                                            
CONECT   26    1   24   28                                                  
CONECT   27    3   24   29                                                  
CONECT   28   26   30                                                       
CONECT   29   27   30                                                       
CONECT   30   28   29                                                       
CONECT   31   12                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0014446
HETATM    1  C1  UNL     1       4.277  -3.463   1.068  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.072  -3.432   0.196  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.500  -4.452  -0.366  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.472  -4.132  -1.065  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.301  -2.778  -0.993  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.278  -2.097  -1.732  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.632  -1.440  -2.906  1.00  0.00           C  
HETATM    8  F1  UNL     1       1.956  -1.451  -3.296  1.00  0.00           F  
HETATM    9  C6  UNL     1      -0.320  -0.801  -3.661  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.658  -0.776  -3.302  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.969  -1.438  -2.136  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.060  -2.080  -1.364  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -1.576  -2.913   0.114  1.00  0.00          CL  
HETATM   14  C10 UNL     1       2.322  -2.339  -0.187  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.641  -0.943   0.169  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.843  -0.622   0.260  1.00  0.00           O  
HETATM   17  N2  UNL     1       1.604  -0.015   0.409  1.00  0.00           N  
HETATM   18  C12 UNL     1       1.712   1.340   0.777  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.339   1.654   2.176  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.042   1.549   3.269  1.00  0.00           O  
HETATM   21  N3  UNL     1       0.038   2.079   1.886  1.00  0.00           N  
HETATM   22  C14 UNL     1      -1.346   2.460   1.928  1.00  0.00           C  
HETATM   23  C15 UNL     1      -1.449   3.901   1.605  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.434   4.604   1.608  1.00  0.00           O  
HETATM   25  O5  UNL     1      -2.672   4.498   1.298  1.00  0.00           O  
HETATM   26  C16 UNL     1      -2.092   1.530   1.045  1.00  0.00           C  
HETATM   27  C17 UNL     1      -3.405   1.978   0.540  1.00  0.00           C  
HETATM   28  C18 UNL     1      -2.247   0.194   1.757  1.00  0.00           C  
HETATM   29  S1  UNL     1      -0.873   1.350  -0.329  1.00  0.00           S  
HETATM   30  C19 UNL     1       0.510   2.208   0.485  1.00  0.00           C  
HETATM   31  H1  UNL     1       5.190  -3.616   0.419  1.00  0.00           H  
HETATM   32  H2  UNL     1       4.365  -2.587   1.733  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.238  -4.356   1.722  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.010  -0.298  -4.570  1.00  0.00           H  
HETATM   35  H5  UNL     1      -2.422  -0.278  -3.894  1.00  0.00           H  
HETATM   36  H6  UNL     1      -3.042  -1.426  -1.828  1.00  0.00           H  
HETATM   37  H7  UNL     1       0.614  -0.405   0.292  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.667   1.886   0.499  1.00  0.00           H  
HETATM   39  H9  UNL     1      -1.742   2.353   2.966  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.709   5.391   0.814  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.274   2.645  -0.331  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.978   2.581   1.308  1.00  0.00           H  
HETATM   43  H13 UNL     1      -4.033   1.124   0.193  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.323  -0.394   1.721  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.025  -0.369   1.195  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.655   0.345   2.784  1.00  0.00           H  
HETATM   47  H17 UNL     1       0.700   3.229   0.153  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   14   14
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   14
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   37
CONECT   18   19   30   38
CONECT   19   20   20   21
CONECT   21   22   30
CONECT   22   23   26   39
CONECT   23   24   24   25
CONECT   25   40
CONECT   26   27   28   29
CONECT   27   41   42   43
CONECT   28   44   45   46
CONECT   29   30
CONECT   30   47
END

HMDB0014446
     RDKit          3D
Flucloxacillin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.2771   -3.4627    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716   -3.4316    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996   -4.4516   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -4.1315   -1.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -2.7783   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -2.0965   -1.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323   -1.4400   -2.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -1.4512   -3.2964 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202   -0.8011   -3.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581   -0.7764   -3.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -1.4378   -2.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -2.0802   -1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -2.9127    0.1144 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -2.3389   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.9431    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432   -0.6222    0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -0.0147    0.4094 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    1.3401    0.7774 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3389    1.6545    2.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0424    1.5487    3.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    2.0795    1.8857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460    2.4601    1.9281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4488    3.9010    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    4.6042    1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717    4.4979    1.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.5299    1.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4046    1.9780    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    0.1944    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8728    1.3495   -0.3286 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101    2.2081    0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1898   -3.6161    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3651   -2.5868    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383   -4.3564    1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -0.2979   -4.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.2779   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424   -1.4261   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.4052    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673    1.8858    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    2.3525    2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7093    5.3907    0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    2.6452   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778    2.5814    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0325    1.1241    0.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.3936    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.3690    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6553    0.3449    2.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999    3.2290    0.1529 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 14  2  2  0
 30 18  1  0
 12  6  1  0
 30 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 17 37  1  0
 18 38  1  6
 22 39  1  1
 25 40  1  0
 27 41  1  0
 27 42  1  0
 27 43  1  0
 28 44  1  0
 28 45  1  0
 28 46  1  0
 30 47  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin	ChEBI
Floxacillin	ChEBI
Floxapen	ChEBI
Flucloxacilina	ChEBI
Flucloxacilline	ChEBI
Flucloxacillinum	ChEBI
MFIPC	Kegg
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Flucloxacillin-sodium	HMDB
Fluorochloroxacillin	HMDB

Chemical Formula

C₁₉H₁₇ClFN₃O₅S

Average Molecular Weight

453.872

Monoisotopic Molecular Weight

453.056147271

IUPAC Name

(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-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

flucloxacillin

CAS Registry Number

5250-39-5

SMILES

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

InChI Identifier

InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1

InChI Key

UIOFUWFRIANQPC-JKIFEVAISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as mitomycins. These are polycyclic compounds with a structure based on an aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolequinones

Direct Parent

Mitomycins

Alternative Parents

Substituents

Mitomycin
Indole
Quinone
Pyrrolizine
1,4-diazinane
Piperazine
Pyrrolidine
Vinylogous amide
Pyrroline
Ketone
Aziridine
Carboximidic acid derivative
Secondary aliphatic amine
Enamine
Azacycle
Secondary amine
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Imine
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Primary amine
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

mitomycin (CHEBI:27504 )
Quinones (C06681 )

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: HMDB0014446)
Membrane (HMDB: HMDB0014446)

Source

Exogenous

Exogenous (HMDB: HMDB0014446)

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	0.054 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.44	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-0.93	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	3	ChemAxon
Refractivity	106.85 m³·mol⁻¹	ChemAxon
Polarizability	41.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	228.362	30932474
DeepCCS	[M+Na]+	203.786	30932474
AllCCS	[M+H]+	195.6	32859911
AllCCS	[M+H-H2O]+	193.4	32859911
AllCCS	[M+NH4]+	197.5	32859911
AllCCS	[M+Na]+	198.1	32859911
AllCCS	[M-H]-	197.8	32859911
AllCCS	[M+Na-2H]-	197.9	32859911
AllCCS	[M+HCOO]-	198.1	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.	5.45 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7121 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2234.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	101.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	494.0 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	629.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1005.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.4 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	1494.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	286.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	142.3 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	63.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flucloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O	4541.4	Standard polar	33892256
Flucloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O	2925.1	Standard non polar	33892256
Flucloxacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl)C(O)=O	3311.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3276.9	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3295.9	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3273.4	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3093.9	Standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3939.7	Standard polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3471.9	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3471.6	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3593.5	Semi standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	3495.8	Standard non polar	33892256
Flucloxacillin,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=C(F)C=CC=C2Cl)=NO1	4067.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flucloxacillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9342300000-7f180b75f0b193e6a2bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flucloxacillin GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9101010000-2499cba418eeed4ea1e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flucloxacillin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 10V, Positive-QTOF	splash10-0ika-1980600000-c09913017680462d6167	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 20V, Positive-QTOF	splash10-03dr-1890100000-189280e6a5ebaeff7bcb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 40V, Positive-QTOF	splash10-0900-3930000000-082278659456539aa269	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 10V, Negative-QTOF	splash10-03di-0029100000-f63d442cb388e6e6a1fe	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 20V, Negative-QTOF	splash10-03di-0179100000-cc81474beec5e49ab711	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 40V, Negative-QTOF	splash10-03di-2943000000-01ada58e630c1108bd3b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 10V, Positive-QTOF	splash10-0udi-0110900000-0d61735c2eb814141c04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 20V, Positive-QTOF	splash10-0w2i-0590300000-b1e7d7edf8865b92c33a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 40V, Positive-QTOF	splash10-01p9-2590000000-21280c81506029576bdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 10V, Negative-QTOF	splash10-0udi-0030900000-0ee6d1f66c3759d652fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 20V, Negative-QTOF	splash10-0f6x-4190100000-fc1930da2cf7aa599457	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flucloxacillin 40V, Negative-QTOF	splash10-0006-9170000000-0fa52b5f4e2c50ce52ad	2021-09-23	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 DB00301	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00301	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00301

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20037

KEGG Compound ID

C11748

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flucloxacillin

METLIN ID

Not Available

PubChem Compound

21319

PDB ID

Not Available

ChEBI ID

5098

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Flucloxacillin (HMDB0014446)

MOL for HMDB0014446 (Flucloxacillin)

3D MOL for HMDB0014446 (Flucloxacillin)

3D SDF for HMDB0014446 (Flucloxacillin)

3D-SDF for HMDB0014446 (Flucloxacillin)

PDB for HMDB0014446 (Flucloxacillin)

3D PDB for HMDB0014446 (Flucloxacillin)

SMILES for HMDB0014446 (Flucloxacillin)

INCHI for HMDB0014446 (Flucloxacillin)

Structure for HMDB0014446 (Flucloxacillin)

3D Structure for HMDB0014446 (Flucloxacillin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References