MiMeDB: Showing metabocard for Pseudomonic acid A (MMDBc0006795)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:11:58 UTC

Update Date

2024-10-11 02:02:35 UTC

Metabolite ID

MMDBc0006795

Metabolite Identification

Common Name

Pseudomonic acid A

Description

Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.

Structure

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

 
  Mrv0541 02231214392D          
 
 35 36  0  0  1  0            999 V2000
   10.8277   -9.6141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8277  -10.4413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5422  -10.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2568  -10.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2568   -9.6141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5422   -9.1984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4019  -10.4454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1170  -10.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1138   -9.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5343   -8.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9686   -9.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6835   -9.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3985   -9.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1135   -9.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8243   -9.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5392   -9.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2542   -9.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9692   -9.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6841   -9.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3991   -9.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1141   -9.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8291   -9.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5398   -9.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2549   -9.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9699   -9.1652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6853  -10.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1153  -10.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2585  -10.4080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845  -10.8602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9680  -10.4437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2506  -10.8585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5341  -10.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4144  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2496  -11.6858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9690   -9.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 31 32  1  0  0  0  0
  3  4  1  0  0  0  0
  7 33  1  1  0  0  0
 29 33  1  1  0  0  0
  4  5  1  0  0  0  0
 31 34  1  1  0  0  0
  5  6  1  0  0  0  0
 30 35  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  6  0  0  0
  1  9  1  1  0  0  0
  6 10  1  1  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 26  1  0  0  0  0
 14 27  2  0  0  0  0
 24 28  2  0  0  0  0
  7 29  1  0  0  0  0
  1  2  1  0  0  0  0
 29 30  1  0  0  0  0
  1  6  1  0  0  0  0
 30 31  1  0  0  0  0
  2  3  1  0  0  0  0
M  END

HMDB0014554
     RDKit          3D
Mupirocin
 79 80  0  0  0  0  0  0  0  0999 V2000
    0.4572   -0.0279   -2.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675   -0.9213   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160   -1.4004   -0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.1201   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.3797   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -1.6652    0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5576   -1.4491    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359   -2.0072   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6005   -1.9197   -0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2843   -0.6320   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864    0.4064   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0907    1.6127   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5319    1.2493   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1036    0.6448    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    1.5177    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5641    2.6777    1.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5281    1.0319    3.1700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -1.1375   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -1.8435    0.1770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2858   -2.1392    0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.0700    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294   -0.0680    1.1743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6666    1.2256    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1179    1.3485    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0070    1.0360    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1216    0.3088    0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3329    0.5854   -0.3634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2167   -0.6733   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1475    1.7702    0.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.3275    1.8541   -0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4846    2.9811   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335    0.2286    1.3501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4087    0.9724    2.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -0.9930    1.4250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1380   -1.7512    2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -0.5903   -2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.2640   -2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    0.8866   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147   -2.0959    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146   -0.3814    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9846   -2.0034    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -3.0898   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -1.5176   -1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1066   -2.4476   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8831   -2.5988   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9597   -0.1964   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898   -0.8693   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2893    0.0717    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.9039   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842    2.3719    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7652    1.9479   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0825    2.2238   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7491    0.5802   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1836    0.4258    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6272   -0.3239    1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5081    0.0500    3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -1.7499   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.1473   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -2.7830    0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362   -1.5039   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9363   -0.5053   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.4846    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    1.6497   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871    2.0104    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3798    2.3664    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9909   -0.7667    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9813    0.7336   -1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8939   -0.6442   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5343   -1.5317   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7559   -0.8093    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5592    1.6882    1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9924    1.0082   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8917    2.7897   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9663    1.8216   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0924    3.7147   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    0.8488    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.5092    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602   -0.6767    1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330   -2.4025    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 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
 25 26  1  0
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 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 19  1  0
 26 24  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
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  9 44  1  0
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 10 47  1  0
 11 48  1  0
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 12 50  1  0
 12 51  1  0
 13 52  1  0
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 14 54  1  0
 14 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  6
 26 66  1  1
 27 67  1  6
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 32 76  1  6
 33 77  1  0
 34 78  1  1
 35 79  1  0
M  END

 
  Mrv0541 02231214392D          
 
 35 36  0  0  1  0            999 V2000
   10.8277   -9.6141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8277  -10.4413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5422  -10.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2568  -10.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2568   -9.6141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5422   -9.1984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4019  -10.4454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1170  -10.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1138   -9.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5343   -8.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9686   -9.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6835   -9.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3985   -9.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1135   -9.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8243   -9.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5392   -9.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2542   -9.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9692   -9.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6841   -9.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3991   -9.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1141   -9.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8291   -9.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5398   -9.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2549   -9.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9699   -9.1652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6853  -10.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1153  -10.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2585  -10.4080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845  -10.8602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9680  -10.4437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2506  -10.8585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5341  -10.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4144  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2496  -11.6858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9690   -9.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 31 32  1  0  0  0  0
  3  4  1  0  0  0  0
  7 33  1  1  0  0  0
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  5  6  1  0  0  0  0
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  2  8  1  6  0  0  0
  1  9  1  1  0  0  0
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 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 26  1  0  0  0  0
 14 27  2  0  0  0  0
 24 28  2  0  0  0  0
  7 29  1  0  0  0  0
  1  2  1  0  0  0  0
 29 30  1  0  0  0  0
  1  6  1  0  0  0  0
 30 31  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006795

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

> <INCHI_KEY>
MINDHVHHQZYEEK-HBBNESRFSA-N

> <FORMULA>
C26H44O9

> <MOLECULAR_WEIGHT>
500.6222

> <EXACT_MASS>
500.298533006

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
55.502431828641676

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.4513256756666664

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.10476992797675

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.834071699171744

> <JCHEM_PKA_STRONGEST_BASIC>
-2.71476683945935

> <JCHEM_POLAR_SURFACE_AREA>
146.04999999999998

> <JCHEM_REFRACTIVITY>
129.3941

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mupirocin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014554
     RDKit          3D
Mupirocin
 79 80  0  0  0  0  0  0  0  0999 V2000
    0.4572   -0.0279   -2.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675   -0.9213   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160   -1.4004   -0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.1201   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.3797   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -1.6652    0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5576   -1.4491    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359   -2.0072   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6005   -1.9197   -0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2843   -0.6320   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864    0.4064   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0907    1.6127   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5319    1.2493   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1036    0.6448    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    1.5177    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5641    2.6777    1.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5281    1.0319    3.1700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -1.1375   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -1.8435    0.1770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2858   -2.1392    0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.0700    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294   -0.0680    1.1743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6666    1.2256    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1179    1.3485    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0070    1.0360    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1216    0.3088    0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3329    0.5854   -0.3634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2167   -0.6733   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1475    1.7702    0.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.3275    1.8541   -0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4846    2.9811   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335    0.2286    1.3501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4087    0.9724    2.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -0.9930    1.4250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1380   -1.7512    2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -0.5903   -2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.2640   -2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    0.8866   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147   -2.0959    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146   -0.3814    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9846   -2.0034    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -3.0898   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -1.5176   -1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1066   -2.4476   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8831   -2.5988   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9597   -0.1964   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898   -0.8693   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2893    0.0717    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.9039   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842    2.3719    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7652    1.9479   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0825    2.2238   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7491    0.5802   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1836    0.4258    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6272   -0.3239    1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5081    0.0500    3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -1.7499   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.1473   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -2.7830    0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362   -1.5039   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9363   -0.5053   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.4846    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    1.6497   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871    2.0104    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3798    2.3664    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9909   -0.7667    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9813    0.7336   -1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8939   -0.6442   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5343   -1.5317   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7559   -0.8093    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5592    1.6882    1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9924    1.0082   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8917    2.7897   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9663    1.8216   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0924    3.7147   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    0.8488    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.5092    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602   -0.6767    1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330   -2.4025    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 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
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 19  1  0
 26 24  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  6
 26 66  1  1
 27 67  1  6
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 32 76  1  6
 33 77  1  0
 34 78  1  1
 35 79  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.212 -17.946   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.212 -19.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.545 -20.259   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      22.879 -19.490   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.879 -17.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.545 -17.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.550 -19.498   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.885 -20.274   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.879 -17.182   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      21.531 -15.626   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.208 -17.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.543 -17.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.877 -17.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.212 -17.923   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      29.539 -17.155   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      30.873 -17.915   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.208 -17.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.543 -17.907   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.877 -17.139   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.212 -17.900   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.546 -17.132   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.881 -17.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      40.208 -17.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      41.542 -17.884   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      42.877 -17.108   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      25.546 -19.475   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      28.215 -19.467   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      41.549 -19.428   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.211 -20.272   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.874 -19.495   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.534 -20.269   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.197 -19.492   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.574 -20.972   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      13.533 -21.813   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.875 -17.951   0.000  0.00  0.00           C+0
CONECT    1    9    2    6                                                  
CONECT    2    8    1    3                                                  
CONECT    3    4    2                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5   10    1                                                  
CONECT    7   33    8   29                                                  
CONECT    8    7    2                                                       
CONECT    9    1                                                            
CONECT   10    6                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24                                                            
CONECT   26   12                                                            
CONECT   27   14                                                            
CONECT   28   24                                                            
CONECT   29   33    7   30                                                  
CONECT   30   35   29   31                                                  
CONECT   31   32   34   30                                                  
CONECT   32   31                                                            
CONECT   33    7   29                                                       
CONECT   34   31                                                            
CONECT   35   30                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

COMPND    HMDB0014554
HETATM    1  C1  UNL     1       0.457  -0.028  -2.279  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.068  -0.921  -1.168  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.816  -1.400  -0.342  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.267  -1.120  -0.424  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.704  -0.380  -1.331  1.00  0.00           O  
HETATM    6  O2  UNL     1       3.136  -1.665   0.485  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.558  -1.449   0.470  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.136  -2.007  -0.781  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.601  -1.920  -0.937  1.00  0.00           C  
HETATM   10  C8  UNL     1       7.284  -0.632  -1.081  1.00  0.00           C  
HETATM   11  C9  UNL     1       7.186   0.406  -0.043  1.00  0.00           C  
HETATM   12  C10 UNL     1       8.091   1.613  -0.370  1.00  0.00           C  
HETATM   13  C11 UNL     1       9.532   1.249  -0.467  1.00  0.00           C  
HETATM   14  C12 UNL     1      10.104   0.645   0.788  1.00  0.00           C  
HETATM   15  C13 UNL     1      10.038   1.518   1.967  1.00  0.00           C  
HETATM   16  O3  UNL     1       9.564   2.678   1.955  1.00  0.00           O  
HETATM   17  O4  UNL     1      10.528   1.032   3.170  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.520  -1.138  -1.058  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.919  -1.843   0.177  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.286  -2.139   0.225  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.137  -1.070   0.084  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.029  -0.068   1.174  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.667   1.226   0.871  1.00  0.00           C  
HETATM   24  C19 UNL     1      -6.118   1.349   0.657  1.00  0.00           C  
HETATM   25  O6  UNL     1      -7.007   1.036   1.690  1.00  0.00           O  
HETATM   26  C20 UNL     1      -7.122   0.309   0.498  1.00  0.00           C  
HETATM   27  C21 UNL     1      -8.333   0.585  -0.363  1.00  0.00           C  
HETATM   28  C22 UNL     1      -9.217  -0.673  -0.388  1.00  0.00           C  
HETATM   29  C23 UNL     1      -9.148   1.770   0.053  1.00  0.00           C  
HETATM   30  C24 UNL     1     -10.327   1.854  -0.939  1.00  0.00           C  
HETATM   31  O7  UNL     1      -8.485   2.981  -0.071  1.00  0.00           O  
HETATM   32  C25 UNL     1      -2.533   0.229   1.350  1.00  0.00           C  
HETATM   33  O8  UNL     1      -2.409   0.972   2.534  1.00  0.00           O  
HETATM   34  C26 UNL     1      -1.687  -0.993   1.425  1.00  0.00           C  
HETATM   35  O9  UNL     1      -2.138  -1.751   2.508  1.00  0.00           O  
HETATM   36  H1  UNL     1       1.104  -0.590  -2.951  1.00  0.00           H  
HETATM   37  H2  UNL     1      -0.432   0.264  -2.914  1.00  0.00           H  
HETATM   38  H3  UNL     1       0.863   0.887  -1.855  1.00  0.00           H  
HETATM   39  H4  UNL     1       0.515  -2.096   0.447  1.00  0.00           H  
HETATM   40  H5  UNL     1       4.715  -0.381   0.637  1.00  0.00           H  
HETATM   41  H6  UNL     1       4.985  -2.003   1.352  1.00  0.00           H  
HETATM   42  H7  UNL     1       4.778  -3.090  -0.899  1.00  0.00           H  
HETATM   43  H8  UNL     1       4.604  -1.518  -1.665  1.00  0.00           H  
HETATM   44  H9  UNL     1       7.107  -2.448  -0.042  1.00  0.00           H  
HETATM   45  H10 UNL     1       6.883  -2.599  -1.812  1.00  0.00           H  
HETATM   46  H11 UNL     1       6.960  -0.196  -2.086  1.00  0.00           H  
HETATM   47  H12 UNL     1       8.390  -0.869  -1.224  1.00  0.00           H  
HETATM   48  H13 UNL     1       7.289   0.072   0.977  1.00  0.00           H  
HETATM   49  H14 UNL     1       6.161   0.904  -0.137  1.00  0.00           H  
HETATM   50  H15 UNL     1       7.884   2.372   0.381  1.00  0.00           H  
HETATM   51  H16 UNL     1       7.765   1.948  -1.385  1.00  0.00           H  
HETATM   52  H17 UNL     1      10.083   2.224  -0.635  1.00  0.00           H  
HETATM   53  H18 UNL     1       9.749   0.580  -1.306  1.00  0.00           H  
HETATM   54  H19 UNL     1      11.184   0.426   0.566  1.00  0.00           H  
HETATM   55  H20 UNL     1       9.627  -0.324   1.022  1.00  0.00           H  
HETATM   56  H21 UNL     1      10.508   0.050   3.418  1.00  0.00           H  
HETATM   57  H22 UNL     1      -1.889  -1.750  -1.941  1.00  0.00           H  
HETATM   58  H23 UNL     1      -1.994  -0.147  -1.228  1.00  0.00           H  
HETATM   59  H24 UNL     1      -1.372  -2.783   0.282  1.00  0.00           H  
HETATM   60  H25 UNL     1      -5.136  -1.504  -0.084  1.00  0.00           H  
HETATM   61  H26 UNL     1      -3.936  -0.505  -0.883  1.00  0.00           H  
HETATM   62  H27 UNL     1      -4.345  -0.485   2.170  1.00  0.00           H  
HETATM   63  H28 UNL     1      -4.158   1.650  -0.057  1.00  0.00           H  
HETATM   64  H29 UNL     1      -4.387   2.010   1.664  1.00  0.00           H  
HETATM   65  H30 UNL     1      -6.380   2.366   0.225  1.00  0.00           H  
HETATM   66  H31 UNL     1      -6.991  -0.767   0.717  1.00  0.00           H  
HETATM   67  H32 UNL     1      -7.981   0.734  -1.399  1.00  0.00           H  
HETATM   68  H33 UNL     1      -9.894  -0.644  -1.271  1.00  0.00           H  
HETATM   69  H34 UNL     1      -8.534  -1.532  -0.546  1.00  0.00           H  
HETATM   70  H35 UNL     1      -9.756  -0.809   0.565  1.00  0.00           H  
HETATM   71  H36 UNL     1      -9.559   1.688   1.068  1.00  0.00           H  
HETATM   72  H37 UNL     1     -10.992   1.008  -0.672  1.00  0.00           H  
HETATM   73  H38 UNL     1     -10.892   2.790  -0.713  1.00  0.00           H  
HETATM   74  H39 UNL     1      -9.966   1.822  -1.979  1.00  0.00           H  
HETATM   75  H40 UNL     1      -9.092   3.715  -0.352  1.00  0.00           H  
HETATM   76  H41 UNL     1      -2.240   0.849   0.482  1.00  0.00           H  
HETATM   77  H42 UNL     1      -1.584   1.509   2.486  1.00  0.00           H  
HETATM   78  H43 UNL     1      -0.660  -0.677   1.511  1.00  0.00           H  
HETATM   79  H44 UNL     1      -2.833  -2.403   2.242  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    3   18
CONECT    3    4   39
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   16   17
CONECT   17   56
CONECT   18   19   57   58
CONECT   19   20   34   59
CONECT   20   21
CONECT   21   22   60   61
CONECT   22   23   32   62
CONECT   23   24   63   64
CONECT   24   25   26   65
CONECT   25   26
CONECT   26   27   66
CONECT   27   28   29   67
CONECT   28   68   69   70
CONECT   29   30   31   71
CONECT   30   72   73   74
CONECT   31   75
CONECT   32   33   34   76
CONECT   33   77
CONECT   34   35   78
CONECT   35   79
END

HMDB0014554
     RDKit          3D
Mupirocin
 79 80  0  0  0  0  0  0  0  0999 V2000
    0.4572   -0.0279   -2.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675   -0.9213   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160   -1.4004   -0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -1.1201   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.3797   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -1.6652    0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5576   -1.4491    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359   -2.0072   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6005   -1.9197   -0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2843   -0.6320   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864    0.4064   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0907    1.6127   -0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5319    1.2493   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1036    0.6448    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375    1.5177    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5641    2.6777    1.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5281    1.0319    3.1700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -1.1375   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -1.8435    0.1770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2858   -2.1392    0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.0700    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294   -0.0680    1.1743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6666    1.2256    0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1179    1.3485    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0070    1.0360    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1216    0.3088    0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3329    0.5854   -0.3634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2167   -0.6733   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1475    1.7702    0.0526 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.3275    1.8541   -0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4846    2.9811   -0.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335    0.2286    1.3501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4087    0.9724    2.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868   -0.9930    1.4250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1380   -1.7512    2.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -0.5903   -2.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.2640   -2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    0.8866   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147   -2.0959    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146   -0.3814    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9846   -2.0034    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -3.0898   -0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035   -1.5176   -1.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1066   -2.4476   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8831   -2.5988   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9597   -0.1964   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898   -0.8693   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2893    0.0717    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.9039   -0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842    2.3719    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7652    1.9479   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0825    2.2238   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7491    0.5802   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1836    0.4258    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6272   -0.3239    1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5081    0.0500    3.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -1.7499   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.1473   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -2.7830    0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362   -1.5039   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9363   -0.5053   -0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.4846    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    1.6497   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871    2.0104    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3798    2.3664    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9909   -0.7667    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9813    0.7336   -1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8939   -0.6442   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5343   -1.5317   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7559   -0.8093    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5592    1.6882    1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9924    1.0082   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8917    2.7897   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9663    1.8216   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0924    3.7147   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398    0.8488    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5840    1.5092    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602   -0.6767    1.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330   -2.4025    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 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
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 19  1  0
 26 24  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  6
 26 66  1  1
 27 67  1  6
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 32 76  1  6
 33 77  1  0
 34 78  1  1
 35 79  1  0
M  END

Synonyms

Value	Source
Bactroban	ChEBI
Centany	ChEBI
Mupirocina	ChEBI
Mupirocine	ChEBI
Mupirocinum	ChEBI
Pseudomonic acid a	ChEBI
Pseudomonate a	Generator
MUP	HMDB
MRC	HMDB
Pseudomonic acid	HMDB
BRL 4910a	HMDB
Mupirocin, 14C-labeled	HMDB
Mupirocin, calcium salt (2:1), dihydrate	HMDB
14C-Labeled mupirocin	HMDB
BRL-4910a	HMDB
Mupirocin, 14C labeled	HMDB
Mupirocin, lithium salt	HMDB
Acid, pseudomonic	HMDB
Mupirocin, calcium salt (2:1)	HMDB
Mupirocin, sodium salt	HMDB
Mupirocin calcium	HMDB

Molecular Formula

C₂₆H₄₄O₉

Average Mass

500.6222

Monoisotopic Mass

500.298533006

IUPAC Name

9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid

Traditional Name

mupirocin

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

InChI Key

MINDHVHHQZYEEK-HBBNESRFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Epoxy fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:7025 )
secondary alcohol (CHEBI:7025 )
epoxide (CHEBI:7025 )
triol (CHEBI:7025 )
alpha,beta-unsaturated carboxylic ester (CHEBI:7025 )
oxanes (CHEBI:7025 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.45	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.05 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	129.39 m³·mol⁻¹	ChemAxon
Polarizability	55.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fc1-2972400000-21f057ea2a2e95898b9d	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-4966726000-06f4a51b9c0619130ac4	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-056r-1976100000-dfa28e3b7efa7b734a99	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0bwa-3920000000-b910c0ca6dcc91904891	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-056r-1976100000-dfa28e3b7efa7b734a99	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0bwa-3920000000-b910c0ca6dcc91904891	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1342920000-677def34a6e414632f7e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0670-6981300000-69aa4a4ddd0866e13409	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-7920100000-472a053832ce780dd335	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0227900000-2b3bd45c30c76c00ada4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kka-9776600000-a91ac251679e309216a5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kml-9840000000-4c1976a6372a21fd11fd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052k-0100900000-2ba1125d17b9a119cec1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2132900000-b2848b38bb227b2c50ba	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052n-4126900000-a6fe8de917ce81221d01	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fus-2126930000-8ef8418ebf22e9aa7d14	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015d-9620200000-8cb94d45ef1676428b42	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9600000000-177c92b81937ff998d8e	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Not Available	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0014554

DrugBank ID

DB00410

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

393914

KEGG Compound ID

C11758

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mupirocin

METLIN ID

Not Available

PubChem Compound

446596

PDB ID

Not Available

ChEBI ID

7025

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Pseudomonic acid A (MMDBc0006795)

MOL for #<Metabolite:0x00007fdb30d0c9c0>

3D MOL for #<Metabolite:0x00007fdb30d0c9c0>

3D SDF for #<Metabolite:0x00007fdb30d0c9c0>

3D-SDF for #<Metabolite:0x00007fdb30d0c9c0>

PDB for #<Metabolite:0x00007fdb30d0c9c0>

3D PDB for #<Metabolite:0x00007fdb30d0c9c0>

SMILES for #<Metabolite:0x00007fdb30d0c9c0>

INCHI for #<Metabolite:0x00007fdb30d0c9c0>

Structure for #<Metabolite:0x00007fdb30d0c9c0>

3D Structure for #<Metabolite:0x00007fdb30d0c9c0>