NP-MRD: Showing NP-Card for Pseudomonic acid A (NP0021323)

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Record Information

Version

1.0

Created at

2021-01-06 06:35:19 UTC

Updated at

2021-07-15 17:36:03 UTC

NP-MRD ID

NP0021323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudomonic acid A

Provided By

NPAtlas

Description

Mupirocin, also known as bactroban or centany, 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. Mupirocin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Pseudomonic acid A is found in Pseudomonas fluorescens. It was first documented in 1977 (PMID: 402371). Based on a literature review a significant number of articles have been published on Mupirocin (PMID: 22500807) (PMID: 23337107) (PMID: 23535880) (PMID: 23543635).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652307042107593D          

 79 80  0  0  0  0            999 V2000
    0.5663    0.3590   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.0612   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -1.8736   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3761   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.2282   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0506   -0.0996   -0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    0.3800    0.2669 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3092    0.1853   -0.8045 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7164    0.6716   -0.3967 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7226    2.1022   -0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0339    2.7003    0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8651    2.2925    1.3640 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4347    0.9382    1.4007 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3023    0.6984    0.1603 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8412   -0.6764    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8334   -0.8679    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316   -1.6807   -0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -1.6541   -1.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.6642   -1.4170   -1.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3850    0.9860   -0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760    0.3463    0.0261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5603    0.6334    0.2120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2655   -0.7049    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1859    1.6774    1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8992   -0.4709    1.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6349   -0.2141    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7229    2.6278   -0.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9350    3.8575    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2927    2.5157    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7595    0.1301    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1109    1.4637    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3240   -2.0592   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -2.6908   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.0964   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -2.4246   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3334   -3.2572    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -3.5868   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614   -2.0647    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -2.3829   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.3483   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4907   -0.4587   -1.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5482    0.2444    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9619    1.2159   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7910   -1.3135   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.7255    1.8084    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 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
 25 26  1  0  0  0  0
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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 19  1  0  0  0  0
 26 24  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  3 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  0  0  0  0
 10 47  1  0  0  0  0
 11 48  1  0  0  0  0
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 13 52  1  0  0  0  0
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 17 56  1  0  0  0  0
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 19 59  1  1  0  0  0
 21 60  1  0  0  0  0
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 34 78  1  6  0  0  0
 35 79  1  0  0  0  0
M  END

     RDKit          3D

 79 80  0  0  0  0  0  0  0  0999 V2000
    0.5663    0.3590   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.0612   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -1.8736   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3761   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.2282   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0506   -0.0996   -0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    0.3800    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3092    0.1853   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164    0.6716   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7226    2.1022   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    2.7003    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8651    2.2925    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347    0.9382    1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3023    0.6984    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8412   -0.6764    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8334   -0.8679    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.3196    2.6521    2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6782    0.8915    2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7255    1.8084    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158    3.1808    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    0.4691   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4227    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    0.3716   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -0.8615    1.5019 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  6
 35 79  1  0
M  END


  Mrv1652307042107593D          

 79 80  0  0  0  0            999 V2000
    0.5663    0.3590   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.0612   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -1.8736   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3761   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.2282   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0506   -0.0996   -0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    0.3800    0.2669 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3092    0.1853   -0.8045 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7164    0.6716   -0.3967 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7226    2.1022   -0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0339    2.7003    0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8651    2.2925    1.3640 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4347    0.9382    1.4007 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3023    0.6984    0.1603 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8412   -0.6764    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8334   -0.8679    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316   -1.6807   -0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -1.6541   -1.7152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9957   -1.6793   -0.8445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0543   -2.3317   -1.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8725   -2.8437   -0.5800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7465   -1.6543   -0.1496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6642   -1.4170   -1.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6686   -0.3389   -1.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3850    0.9860   -0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760    0.3463    0.0261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5603    0.6334    0.2120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2655   -0.7049    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7211    1.3853    1.5034 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1859    1.6774    1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0909    2.6354    1.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405   -0.4879    0.2441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8992   -0.4709    1.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.4535   -0.2156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6784   -0.0906    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.9519   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269    0.7434   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8411    0.4834    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294   -2.9080   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.2141    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    1.4696    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.8762   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564    0.7514   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.0770    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210    0.4192   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1770    2.7260   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    2.2088    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229    2.6278   -0.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9350    3.8575    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2927    2.5157    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7414    3.0455    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7595    0.1301    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2010    0.8990    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7083    0.7796   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1109    1.4637    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3240   -2.0592   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -2.6908   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.0964   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -2.4246   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3334   -3.2572    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -3.5868   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614   -2.0647    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -2.3829   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.3483   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4907   -0.4587   -1.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5482    0.2444    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9619    1.2159   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7910   -1.3135   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3541   -0.6343    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -1.2301    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3425    0.8461    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3196    2.6521    2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6782    0.8915    2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7255    1.8084    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158    3.1808    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    0.4691   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4227    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    0.3716   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -0.8615    1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 19  1  0  0  0  0
 26 24  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  3 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  0  0  0  0
 10 47  1  0  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
 14 54  1  0  0  0  0
 14 55  1  0  0  0  0
 17 56  1  0  0  0  0
 18 57  1  0  0  0  0
 18 58  1  0  0  0  0
 19 59  1  1  0  0  0
 21 60  1  0  0  0  0
 21 61  1  0  0  0  0
 22 62  1  1  0  0  0
 23 63  1  0  0  0  0
 23 64  1  0  0  0  0
 24 65  1  6  0  0  0
 26 66  1  1  0  0  0
 27 67  1  6  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 28 70  1  0  0  0  0
 29 71  1  1  0  0  0
 30 72  1  0  0  0  0
 30 73  1  0  0  0  0
 30 74  1  0  0  0  0
 31 75  1  0  0  0  0
 32 76  1  6  0  0  0
 33 77  1  0  0  0  0
 34 78  1  6  0  0  0
 35 79  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(=O)C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@]1([H])OC([H])([H])[C@]([H])(C([H])([H])[C@]2([H])O[C@@]2([H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[H])[C@@]([H])(O[H])[C@@]1([H])O[H]

> <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_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.816993865961905

> <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

$$$$

     RDKit          3D

 79 80  0  0  0  0  0  0  0  0999 V2000
    0.5663    0.3590   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.0612   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -1.8736   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3761   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.2282   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0506   -0.0996   -0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    0.3800    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3092    0.1853   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164    0.6716   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7226    2.1022   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    2.7003    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8651    2.2925    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347    0.9382    1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3023    0.6984    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8412   -0.6764    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8334   -0.8679    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316   -1.6807   -0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -1.6541   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -1.6793   -0.8445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0543   -2.3317   -1.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8725   -2.8437   -0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7465   -1.6543   -0.1496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6642   -1.4170   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6686   -0.3389   -1.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3850    0.9860   -0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760    0.3463    0.0261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5603    0.6334    0.2120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2655   -0.7049    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7211    1.3853    1.5034 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1859    1.6774    1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0909    2.6354    1.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405   -0.4879    0.2441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8992   -0.4709    1.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.4535   -0.2156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6784   -0.0906    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.9519   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269    0.7434   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8411    0.4834    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294   -2.9080   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.2141    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    1.4696    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.8762   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564    0.7514   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.0770    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210    0.4192   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1770    2.7260   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    2.2088    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229    2.6278   -0.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9350    3.8575    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2927    2.5157    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7414    3.0455    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7595    0.1301    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2010    0.8990    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7083    0.7796   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1109    1.4637    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3240   -2.0592   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -2.6908   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.0964   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -2.4246   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3334   -3.2572    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -3.5868   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614   -2.0647    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -2.3829   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.3483   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4907   -0.4587   -1.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5482    0.2444    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9619    1.2159   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7910   -1.3135   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3541   -0.6343    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -1.2301    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3425    0.8461    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3196    2.6521    2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6782    0.8915    2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7255    1.8084    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158    3.1808    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    0.4691   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4227    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    0.3716   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -0.8615    1.5019 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  6
 35 79  1  0
M  END

HEADER    PROTEIN                                 04-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-21         0                                  
HETATM    1  C   UNK     0       0.566   0.359  -0.845  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.401  -1.061  -1.172  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465  -1.874  -1.018  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.741  -1.376  -0.543  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.699  -2.228  -0.438  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.051  -0.100  -0.189  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.296   0.380   0.267  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.309   0.185  -0.805  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.716   0.672  -0.397  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.723   2.102  -0.073  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.034   2.700   0.240  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.865   2.293   1.364  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.435   0.938   1.401  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.302   0.698   0.160  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.841  -0.676   0.249  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.833  -0.868   0.987  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.232  -1.681  -0.480  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.813  -1.654  -1.715  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.996  -1.679  -0.845  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.054  -2.332  -1.581  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.873  -2.844  -0.580  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.747  -1.654  -0.150  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.664  -1.417  -1.298  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.669  -0.339  -1.179  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.385   0.986  -0.973  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.076   0.346   0.026  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.560   0.633   0.212  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.265  -0.705   0.211  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.721   1.385   1.503  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.186   1.677   1.706  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.091   2.635   1.328  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.941  -0.488   0.244  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.899  -0.471   1.665  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.500  -0.454  -0.216  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.678  -0.091   0.851  0.00  0.00           O+0
HETATM   36  H   UNK     0      -0.288   0.952  -1.209  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.427   0.743  -1.514  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.841   0.483   0.199  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.329  -2.908  -1.261  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.635  -0.214   1.163  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.223   1.470   0.543  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.427  -0.876  -1.071  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.956   0.751  -1.709  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.944   0.077   0.533  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.421   0.419  -1.197  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.177   2.726  -0.847  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.071   2.209   0.875  0.00  0.00           H+0
HETATM   48  H   UNK     0       8.723   2.628  -0.696  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.935   3.857   0.265  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.293   2.516   2.342  0.00  0.00           H+0
HETATM   51  H   UNK     0       9.741   3.046   1.403  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.759   0.130   1.547  0.00  0.00           H+0
HETATM   53  H   UNK     0      10.201   0.899   2.270  0.00  0.00           H+0
HETATM   54  H   UNK     0       9.708   0.780  -0.762  0.00  0.00           H+0
HETATM   55  H   UNK     0      11.111   1.464   0.156  0.00  0.00           H+0
HETATM   56  H   UNK     0       9.324  -2.059  -0.193  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.602  -2.691  -2.118  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.113  -1.096  -2.655  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.780  -2.425  -0.018  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.333  -3.257   0.270  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.604  -3.587  -1.009  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.361  -2.065   0.704  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.247  -2.383  -1.433  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.041  -1.348  -2.223  0.00  0.00           H+0
HETATM   65  H   UNK     0      -7.491  -0.459  -1.963  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.548   0.244   0.986  0.00  0.00           H+0
HETATM   67  H   UNK     0      -8.962   1.216  -0.651  0.00  0.00           H+0
HETATM   68  H   UNK     0      -8.791  -1.313  -0.606  0.00  0.00           H+0
HETATM   69  H   UNK     0     -10.354  -0.634   0.101  0.00  0.00           H+0
HETATM   70  H   UNK     0      -8.963  -1.230   1.164  0.00  0.00           H+0
HETATM   71  H   UNK     0      -8.342   0.846   2.373  0.00  0.00           H+0
HETATM   72  H   UNK     0     -10.320   2.652   2.256  0.00  0.00           H+0
HETATM   73  H   UNK     0     -10.678   0.892   2.348  0.00  0.00           H+0
HETATM   74  H   UNK     0     -10.726   1.808   0.748  0.00  0.00           H+0
HETATM   75  H   UNK     0      -8.716   3.181   0.766  0.00  0.00           H+0
HETATM   76  H   UNK     0      -4.428   0.469  -0.014  0.00  0.00           H+0
HETATM   77  H   UNK     0      -3.862  -1.423   1.955  0.00  0.00           H+0
HETATM   78  H   UNK     0      -2.447   0.372  -0.965  0.00  0.00           H+0
HETATM   79  H   UNK     0      -1.643  -0.862   1.502  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3   18                                                  
CONECT    3    2    4   39                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   40   41                                             
CONECT    8    7    9   42   43                                             
CONECT    9    8   10   44   45                                             
CONECT   10    9   11   46   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   11   13   50   51                                             
CONECT   13   12   14   52   53                                             
CONECT   14   13   15   54   55                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   56                                                       
CONECT   18    2   19   57   58                                             
CONECT   19   18   20   34   59                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   60   61                                             
CONECT   22   21   23   32   62                                             
CONECT   23   22   24   63   64                                             
CONECT   24   23   25   26   65                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   24   66                                             
CONECT   27   26   28   29   67                                             
CONECT   28   27   68   69   70                                             
CONECT   29   27   30   31   71                                             
CONECT   30   29   72   73   74                                             
CONECT   31   29   75                                                       
CONECT   32   22   33   34   76                                             
CONECT   33   32   77                                                       
CONECT   34   32   35   19   78                                             
CONECT   35   34   79                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   14                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   19                                                            
CONECT   60   21                                                            
CONECT   61   21                                                            
CONECT   62   22                                                            
CONECT   63   23                                                            
CONECT   64   23                                                            
CONECT   65   24                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   28                                                            
CONECT   71   29                                                            
CONECT   72   30                                                            
CONECT   73   30                                                            
CONECT   74   30                                                            
CONECT   75   31                                                            
CONECT   76   32                                                            
CONECT   77   33                                                            
CONECT   78   34                                                            
CONECT   79   35                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  160    0
END

RDKit          3D

79 80  0  0  0  0  0  0  0  0999 V2000
    0.5663    0.3590   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.0612   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -1.8736   -1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3761   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.2282   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0506   -0.0996   -0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    0.3800    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3092    0.1853   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164    0.6716   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7226    2.1022   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0339    2.7003    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8651    2.2925    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4347    0.9382    1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3023    0.6984    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8412   -0.6764    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8334   -0.8679    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316   -1.6807   -0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -1.6541   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -1.6793   -0.8445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0543   -2.3317   -1.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8725   -2.8437   -0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7465   -1.6543   -0.1496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6642   -1.4170   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6686   -0.3389   -1.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3850    0.9860   -0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760    0.3463    0.0261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5603    0.6334    0.2120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2655   -0.7049    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7211    1.3853    1.5034 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1859    1.6774    1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0909    2.6354    1.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405   -0.4879    0.2441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8992   -0.4709    1.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.4535   -0.2156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6784   -0.0906    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.9519   -1.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269    0.7434   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8411    0.4834    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3294   -2.9080   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.2141    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231    1.4696    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.8762   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564    0.7514   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.0770    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210    0.4192   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1770    2.7260   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    2.2088    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9350    3.8575    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2927    2.5157    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7414    3.0455    1.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7595    0.1301    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2010    0.8990    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7083    0.7796   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1109    1.4637    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3240   -2.0592   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -2.6908   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.0964   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7803   -2.4246   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3334   -3.2572    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -3.5868   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614   -2.0647    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -2.3829   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0412   -1.3483   -2.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4907   -0.4587   -1.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5482    0.2444    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9619    1.2159   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7910   -1.3135   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3541   -0.6343    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9631   -1.2301    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3425    0.8461    2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3196    2.6521    2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6782    0.8915    2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7255    1.8084    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8616   -1.4227    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    0.3716   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -0.8615    1.5019 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
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  6  7  1  0
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  1 38  1  0
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 35 79  1  0
M  END

View in JSmol View NMR Assignments

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

Chemical Formula

C₂₆H₄₄O₉

Average Mass

500.6222 Da

Monoisotopic Mass

500.29853 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas fluorescens	NPAtlas	402371

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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.25	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	55.82 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

External Links

NPAtlas ID

NPA006173

HMDB ID

HMDB0014554

DrugBank ID

DB00410

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Chain EB, Mellows G: Pseudomonic acid. Part 1. The structure of pseudomonic acid A, a novel antibiotic produced by Pseudomonas fluorescens. J Chem Soc Perkin 1. 1977;(3):294-309. [PubMed:402371 ]
Melo JA, Ruvkun G: Inactivation of conserved C. elegans genes engages pathogen- and xenobiotic-associated defenses. Cell. 2012 Apr 13;149(2):452-66. doi: 10.1016/j.cell.2012.02.050. [PubMed:22500807 ]
Lee H, Lim H, Bae IK, Yong D, Jeong SH, Lee K, Chong Y: Coexistence of mupirocin and antiseptic resistance in methicillin-resistant Staphylococcus aureus isolates from Korea. Diagn Microbiol Infect Dis. 2013 Mar;75(3):308-12. doi: 10.1016/j.diagmicrobio.2012.11.025. Epub 2013 Jan 18. [PubMed:23337107 ]
Desroches M, Potier J, Laurent F, Bourrel AS, Doucet-Populaire F, Decousser JW: Prevalence of mupirocin resistance among invasive coagulase-negative staphylococci and methicillin-resistant Staphylococcus aureus (MRSA) in France: emergence of a mupirocin-resistant MRSA clone harbouring mupA. J Antimicrob Chemother. 2013 Aug;68(8):1714-7. doi: 10.1093/jac/dkt085. Epub 2013 Mar 27. [PubMed:23535880 ]
S J, M M, A S SB, Mathew R, M K, Lal Y B: Prevalence of High and Low Level Mupirocin Resistance among Staphylococcal Isolates from Skin Infection in a Tertiary Care Hospital. J Clin Diagn Res. 2013 Feb;7(2):238-42. doi: 10.7860/JCDR/2013/4694.2736. Epub 2013 Feb 1. [PubMed:23543635 ]

Showing NP-Card for Pseudomonic acid A (NP0021323)

MOL for NP0021323 (Pseudomonic acid A)

3D MOL for NP0021323 (Pseudomonic acid A)

3D SDF for NP0021323 (Pseudomonic acid A)

3D-SDF for NP0021323 (Pseudomonic acid A)

PDB for NP0021323 (Pseudomonic acid A)

3D PDB for NP0021323 (Pseudomonic acid A)

SMILES for NP0021323 (Pseudomonic acid A)

INCHI for NP0021323 (Pseudomonic acid A)

Structure for NP0021323 (Pseudomonic acid A)

3D Structure for NP0021323 (Pseudomonic acid A)