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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015543

Secondary Accession Numbers

HMDB15543

Metabolite Identification

Common Name

Pivmecillinam

Description

Pivmecillinam is only found in individuals that have used or taken this drug. It is a mecillinam prodrug, a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [PubChem]Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins

Structure

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

  Mrv0541 04191212182D          

 32 34  0  0  1  0            999 V2000
   -0.8250    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0800    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -0.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    2.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    1.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3273    2.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7398    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -1.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  1  4  1  0  0  0  0
  4  2  1  0  0  0  0
 28  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  6  1  0  0  0  0
  9  4  2  0  0  0  0
  5 28  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  3 10  1  6  0  0  0
  1 11  1  1  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 17 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 12 20  1  4  0  0  0
 23 21  1  0  0  0  0
 22 21  1  0  0  0  0
 25 21  2  0  0  0  0
 26 22  1  0  0  0  0
 27 22  1  0  0  0  0
 24 30  1  0  0  0  0
 24 23  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  0  0  0  0
 31 29  2  0  0  0  0
 22 32  1  0  0  0  0
M  END

HMDB0015543
     RDKit          3D
Pivmecillinam
 63 65  0  0  0  0  0  0  0  0999 V2000
    5.3162   -0.4062   -2.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -1.5456   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -2.3470   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -2.4248   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8720   -0.9589    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074   -1.1497    1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -0.1686    0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969    0.4269    1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.1504    1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020    2.1758    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    2.4885   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464    2.9414    0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1431    2.4590    1.2326 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    2.4704    2.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    3.0912    3.4247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    1.3574    1.7197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0077    1.7091    1.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453    0.8407    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.5710    0.7672 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7138   -1.2203    2.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121   -2.3633    2.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459   -2.0058    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568   -2.6540   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8868   -1.6261   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.2320   -0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702    1.1307    0.8759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8312    1.3957   -0.9169 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    2.7870   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    2.4410   -2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3865    4.0441   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3145   -2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.5223   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -0.5786   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3335   -1.7324   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -2.7548    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4419   -3.1718   -1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -1.9296   -1.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -2.5372   -2.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -3.3976   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436   -0.3835    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    1.0526    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    4.0214    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    0.5393    2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    1.1882    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0243   -0.4933    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308   -1.6798    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -2.4219    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.3202    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.9161    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8275   -2.3946    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4918   -2.9564   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964   -3.5328   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605   -0.7560   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.0461   -2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -2.1723   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201   -0.6025   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    0.2893    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1894    3.2578   -2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679    1.4577   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    2.3414   -3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    3.9668   -1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    4.3662   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    4.8530   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 12  1  0
 26 13  1  0
 25 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  1
 16 43  1  1
 18 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  6
 29 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
M  END

  Mrv0541 04191212182D          

 32 34  0  0  1  0            999 V2000
   -0.8250    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0800    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -0.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    2.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    1.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3273    2.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7398    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -1.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  1  4  1  0  0  0  0
  4  2  1  0  0  0  0
 28  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  6  1  0  0  0  0
  9  4  2  0  0  0  0
  5 28  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  3 10  1  6  0  0  0
  1 11  1  1  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 17 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 12 20  1  4  0  0  0
 23 21  1  0  0  0  0
 22 21  1  0  0  0  0
 25 21  2  0  0  0  0
 26 22  1  0  0  0  0
 27 22  1  0  0  0  0
 24 30  1  0  0  0  0
 24 23  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  0  0  0  0
 31 29  2  0  0  0  0
 22 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015543

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1

> <INCHI_KEY>
NPGNOVNWUSPMDP-HLLBOEOZSA-N

> <FORMULA>
C21H33N3O5S

> <MOLECULAR_WEIGHT>
439.569

> <EXACT_MASS>
439.214091871

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.70248610180789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.9085426906666667

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.660257128507617

> <JCHEM_PKA_STRONGEST_BASIC>
7.914073683805415

> <JCHEM_POLAR_SURFACE_AREA>
88.50999999999999

> <JCHEM_REFRACTIVITY>
113.0317

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pivmecilinamo

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015543
     RDKit          3D
Pivmecillinam
 63 65  0  0  0  0  0  0  0  0999 V2000
    5.3162   -0.4062   -2.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -1.5456   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -2.3470   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -2.4248   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8720   -0.9589    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074   -1.1497    1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -0.1686    0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969    0.4269    1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.1504    1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020    2.1758    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    2.4885   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464    2.9414    0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1431    2.4590    1.2326 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    2.4704    2.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    3.0912    3.4247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    1.3574    1.7197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0077    1.7091    1.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453    0.8407    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.5710    0.7672 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7138   -1.2203    2.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121   -2.3633    2.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459   -2.0058    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568   -2.6540   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8868   -1.6261   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.2320   -0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702    1.1307    0.8759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8312    1.3957   -0.9169 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    2.7870   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    2.4410   -2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3865    4.0441   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3145   -2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.5223   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -0.5786   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3335   -1.7324   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -2.7548    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4419   -3.1718   -1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -1.9296   -1.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -2.5372   -2.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -3.3976   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436   -0.3835    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    1.0526    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    4.0214    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    0.5393    2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    1.1882    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0243   -0.4933    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308   -1.6798    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -2.4219    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.3202    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.9161    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8275   -2.3946    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4918   -2.9564   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964   -3.5328   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605   -0.7560   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.0461   -2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -2.1723   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201   -0.6025   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    0.2893    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1894    3.2578   -2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679    1.4577   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    2.3414   -3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    3.9668   -1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    4.3662   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    4.8530   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 12  1  0
 26 13  1  0
 25 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  1
 16 43  1  1
 18 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  6
 29 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.540   1.540   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       1.465   2.016   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       3.711   0.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.711   1.526   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.629  -1.089   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   11  N   UNK     0      -2.874   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.207   1.540   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -5.541   2.310   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -6.814   1.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.426   3.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.555   4.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.285   1.896   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.078   4.664   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.848   3.330   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -4.207   0.000   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       6.799  -2.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.466  -2.786   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.132  -2.016   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.467  -2.016   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.133  -4.326   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.798  -2.786   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.131  -2.786   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.467  -3.556   0.000  0.00  0.00           C+0
CONECT    1    3    4   11                                                  
CONECT    2    4   28    3                                                  
CONECT    3    1    2    6   10                                             
CONECT    4    1    2    9                                                  
CONECT    5   28    6    7    8                                             
CONECT    6    3    5                                                       
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    3                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   17                                                       
CONECT   15   13   16                                                       
CONECT   16   15   18                                                       
CONECT   17   14   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18                                                       
CONECT   20   12                                                            
CONECT   21   23   22   25                                                  
CONECT   22   21   26   27   32                                             
CONECT   23   21   24                                                       
CONECT   24   30   23                                                       
CONECT   25   21                                                            
CONECT   26   22                                                            
CONECT   27   22                                                            
CONECT   28    2    5   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   24   29                                                       
CONECT   31   29                                                            
CONECT   32   22                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0015543
HETATM    1  C1  UNL     1       5.316  -0.406  -2.020  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.148  -1.546  -1.058  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.429  -2.347  -0.944  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.972  -2.425  -1.441  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.872  -0.959   0.301  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.607  -1.150   1.282  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.729  -0.169   0.426  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.397   0.427   1.687  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.199   1.150   1.465  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.102   2.176   0.552  1.00  0.00           C  
HETATM   11  O4  UNL     1       3.109   2.489  -0.114  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.846   2.941   0.313  1.00  0.00           C  
HETATM   13  N1  UNL     1      -0.143   2.459   1.233  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.023   2.470   2.350  1.00  0.00           C  
HETATM   15  O5  UNL     1      -1.176   3.091   3.425  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.784   1.357   1.720  1.00  0.00           C  
HETATM   17  N2  UNL     1      -3.008   1.709   1.118  1.00  0.00           N  
HETATM   18  C11 UNL     1      -3.845   0.841   0.700  1.00  0.00           C  
HETATM   19  N3  UNL     1      -3.687  -0.571   0.767  1.00  0.00           N  
HETATM   20  C12 UNL     1      -3.714  -1.220   2.044  1.00  0.00           C  
HETATM   21  C13 UNL     1      -4.712  -2.363   2.081  1.00  0.00           C  
HETATM   22  C14 UNL     1      -5.846  -2.006   1.148  1.00  0.00           C  
HETATM   23  C15 UNL     1      -5.557  -2.654  -0.200  1.00  0.00           C  
HETATM   24  C16 UNL     1      -4.887  -1.626  -1.058  1.00  0.00           C  
HETATM   25  C17 UNL     1      -3.514  -1.232  -0.526  1.00  0.00           C  
HETATM   26  C18 UNL     1      -0.570   1.131   0.876  1.00  0.00           C  
HETATM   27  S1  UNL     1      -0.831   1.396  -0.917  1.00  0.00           S  
HETATM   28  C19 UNL     1       0.323   2.787  -1.098  1.00  0.00           C  
HETATM   29  C20 UNL     1       1.442   2.441  -2.063  1.00  0.00           C  
HETATM   30  C21 UNL     1      -0.387   4.044  -1.528  1.00  0.00           C  
HETATM   31  H1  UNL     1       4.375  -0.314  -2.604  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.559   0.522  -1.467  1.00  0.00           H  
HETATM   33  H3  UNL     1       6.133  -0.579  -2.754  1.00  0.00           H  
HETATM   34  H4  UNL     1       7.334  -1.732  -1.167  1.00  0.00           H  
HETATM   35  H5  UNL     1       6.504  -2.755   0.088  1.00  0.00           H  
HETATM   36  H6  UNL     1       6.442  -3.172  -1.675  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.025  -1.930  -1.141  1.00  0.00           H  
HETATM   38  H8  UNL     1       3.927  -2.537  -2.560  1.00  0.00           H  
HETATM   39  H9  UNL     1       4.003  -3.398  -0.943  1.00  0.00           H  
HETATM   40  H10 UNL     1       3.244  -0.384   2.400  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.235   1.053   2.017  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.078   4.021   0.529  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.874   0.539   2.469  1.00  0.00           H  
HETATM   44  H14 UNL     1      -4.792   1.188   0.242  1.00  0.00           H  
HETATM   45  H15 UNL     1      -4.024  -0.493   2.815  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.731  -1.680   2.229  1.00  0.00           H  
HETATM   47  H17 UNL     1      -5.106  -2.422   3.113  1.00  0.00           H  
HETATM   48  H18 UNL     1      -4.248  -3.320   1.764  1.00  0.00           H  
HETATM   49  H19 UNL     1      -5.968  -0.916   1.070  1.00  0.00           H  
HETATM   50  H20 UNL     1      -6.828  -2.395   1.533  1.00  0.00           H  
HETATM   51  H21 UNL     1      -6.492  -2.956  -0.721  1.00  0.00           H  
HETATM   52  H22 UNL     1      -4.896  -3.533  -0.021  1.00  0.00           H  
HETATM   53  H23 UNL     1      -5.560  -0.756  -1.162  1.00  0.00           H  
HETATM   54  H24 UNL     1      -4.773  -2.046  -2.088  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.931  -2.172  -0.447  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.020  -0.603  -1.269  1.00  0.00           H  
HETATM   57  H27 UNL     1       0.066   0.289   1.124  1.00  0.00           H  
HETATM   58  H28 UNL     1       2.189   3.258  -2.103  1.00  0.00           H  
HETATM   59  H29 UNL     1       1.868   1.458  -1.794  1.00  0.00           H  
HETATM   60  H30 UNL     1       1.049   2.341  -3.107  1.00  0.00           H  
HETATM   61  H31 UNL     1      -1.482   3.967  -1.518  1.00  0.00           H  
HETATM   62  H32 UNL     1      -0.024   4.366  -2.543  1.00  0.00           H  
HETATM   63  H33 UNL     1      -0.091   4.853  -0.829  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    5
CONECT    3   34   35   36
CONECT    4   37   38   39
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   40   41
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   28   42
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   16   17   26   43
CONECT   17   18   18
CONECT   18   19   44
CONECT   19   20   25
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   23   49   50
CONECT   23   24   51   52
CONECT   24   25   53   54
CONECT   25   55   56
CONECT   26   27   57
CONECT   27   28
CONECT   28   29   30
CONECT   29   58   59   60
CONECT   30   61   62   63
END

HMDB0015543
     RDKit          3D
Pivmecillinam
 63 65  0  0  0  0  0  0  0  0999 V2000
    5.3162   -0.4062   -2.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -1.5456   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -2.3470   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -2.4248   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8720   -0.9589    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074   -1.1497    1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -0.1686    0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969    0.4269    1.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    1.1504    1.4653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020    2.1758    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    2.4885   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8464    2.9414    0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1431    2.4590    1.2326 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    2.4704    2.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765    3.0912    3.4247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    1.3574    1.7197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0077    1.7091    1.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453    0.8407    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.5710    0.7672 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7138   -1.2203    2.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121   -2.3633    2.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459   -2.0058    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568   -2.6540   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8868   -1.6261   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.2320   -0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702    1.1307    0.8759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8312    1.3957   -0.9169 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    2.7870   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    2.4410   -2.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3865    4.0441   -1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3145   -2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.5223   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -0.5786   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3335   -1.7324   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -2.7548    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4419   -3.1718   -1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -1.9296   -1.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -2.5372   -2.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -3.3976   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436   -0.3835    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    1.0526    2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    4.0214    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    0.5393    2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    1.1882    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0243   -0.4933    2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308   -1.6798    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063   -2.4219    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.3202    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9677   -0.9161    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8275   -2.3946    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4918   -2.9564   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964   -3.5328   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605   -0.7560   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -2.0461   -2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -2.1723   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201   -0.6025   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656    0.2893    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1894    3.2578   -2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679    1.4577   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    2.3414   -3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    3.9668   -1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    4.3662   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    4.8530   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
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 16 26  1  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
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 30 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	ChEBI
Amdinocillin pivoxil	ChEBI
Amdinocillin, pivaloyloxymethyl ester	ChEBI
Pivmecilinamo	ChEBI
Pivmecillinamum	ChEBI
[(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	Generator
Leo brand OF pivmecillinam hydrochloride	HMDB
Pivamdinocillin	HMDB
Hydrochloride, pivmecillinam	HMDB
Mecillinam pivaloyl ester	HMDB
Pivmecillinam hydrochloride	HMDB
Pivaloyl ester, mecillinam	HMDB
Pivoxil, amdinocillin	HMDB
Selexid	HMDB

Chemical Formula

C₂₁H₃₃N₃O₅S

Average Molecular Weight

439.569

Monoisotopic Molecular Weight

439.214091871

IUPAC Name

[(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

Traditional Name

pivmecilinamo

CAS Registry Number

32886-97-8

SMILES

[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1

InChI Identifier

InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1

InChI Key

NPGNOVNWUSPMDP-HLLBOEOZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Penam
Azepane
Acylal
Dicarboxylic acid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Carboxylic acid ester
Lactam
Acetal
Amidine
Formamidine
Carboxylic acid amidine
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Hemithioaminal
Thioether
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

penicillanic acid ester (CHEBI:51210 )
penicillin (CHEBI:51210 )

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: HMDB0015543)

Source

Exogenous

Exogenous (HMDB: HMDB0015543)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.053 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.053 g/L	ALOGPS
logP	3.23	ALOGPS
logP	2.91	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.03 m³·mol⁻¹	ChemAxon
Polarizability	47.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	198.617	31661259
DarkChem	[M-H]-	188.361	31661259
DeepCCS	[M-2H]-	242.405	30932474
DeepCCS	[M+Na]+	217.431	30932474
AllCCS	[M+H]+	199.3	32859911
AllCCS	[M+H-H2O]+	197.5	32859911
AllCCS	[M+NH4]+	200.9	32859911
AllCCS	[M+Na]+	201.3	32859911
AllCCS	[M-H]-	197.8	32859911
AllCCS	[M+Na-2H]-	199.1	32859911
AllCCS	[M+HCOO]-	200.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pivmecillinam	[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1	3243.9	Standard polar	33892256
Pivmecillinam	[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1	2878.1	Standard non polar	33892256
Pivmecillinam	[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1	2923.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pivmecillinam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9012000000-ea9d35d8c75e4246ab91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pivmecillinam 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 - Pivmecillinam 10V, Positive-QTOF	splash10-0lkc-0933100000-207d607d624521759c4a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 20V, Positive-QTOF	splash10-066r-2911000000-e698803b355747dc85ad	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 40V, Positive-QTOF	splash10-0a4i-9400000000-4c251e4b9870f1bb8e2e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 10V, Negative-QTOF	splash10-001i-0911000000-0118b6d73875ca106ecc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 20V, Negative-QTOF	splash10-001i-1931000000-ced5e83f734188289e15	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 40V, Negative-QTOF	splash10-00c0-9612000000-5d2b3043f24082963710	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 10V, Positive-QTOF	splash10-0006-0010900000-76b3918141d7d2d0d18c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 20V, Positive-QTOF	splash10-0a4r-5922100000-010f81553366b87ff596	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 40V, Positive-QTOF	splash10-0cdi-3900000000-1058b7a1dbaa55f96dc3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 10V, Negative-QTOF	splash10-03fr-0033900000-bc636cd9795ad82fa708	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 20V, Negative-QTOF	splash10-004j-3966200000-0506d8a084039adb337d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivmecillinam 40V, Negative-QTOF	splash10-00di-9653100000-76e29891ae64774b4657	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB01605	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01605	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01605

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16735658

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pivmecillinam

METLIN ID

Not Available

PubChem Compound

115163

PDB ID

Not Available

ChEBI ID

51210

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

Authors unspecified: Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. [PubMed:214285 ]
Sjovall J, Huitfeldt B, Magni L, Nord CE: Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. [PubMed:3547627 ]
Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [PubMed:14527775 ]

Showing metabocard for Pivmecillinam (HMDB0015543)

MOL for HMDB0015543 (Pivmecillinam)

3D MOL for HMDB0015543 (Pivmecillinam)

3D SDF for HMDB0015543 (Pivmecillinam)

3D-SDF for HMDB0015543 (Pivmecillinam)

PDB for HMDB0015543 (Pivmecillinam)

3D PDB for HMDB0015543 (Pivmecillinam)

SMILES for HMDB0015543 (Pivmecillinam)

INCHI for HMDB0015543 (Pivmecillinam)

Structure for HMDB0015543 (Pivmecillinam)

3D Structure for HMDB0015543 (Pivmecillinam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra