Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015386

Secondary Accession Numbers

HMDB15386

Metabolite Identification

Common Name

Retapamulin

Description

Retapamulin, also known as SB 275833 or altabax, belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety. Based on a literature review a significant number of articles have been published on Retapamulin.

Structure

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

6918462
  Mrv0541 02231215212D          

 36 40  0  0  1  0            999 V2000
    5.1111    0.5988    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -1.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5002   -3.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749   -4.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9632   -0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050   -4.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6903   -3.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6903   -2.9094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2059   -4.0609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4050   -2.4969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1195   -3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323   -4.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -2.2587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1195   -2.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -4.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7054   -3.4288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4165   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040   -2.6296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9625   -2.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059   -2.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6048   -4.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4220   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1063   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383   -0.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567    3.3124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1558    3.5107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6851    1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5539    4.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530    5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502    2.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 14  2  1  6  0  0  0
  2 26  1  0  0  0  0
 17  3  1  1  0  0  0
  4 16  2  0  0  0  0
  5 26  2  0  0  0  0
 28  6  1  6  0  0  0
 29  6  1  1  0  0  0
  6 36  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
  8 16  1  1  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 21  1  1  0  0  0
 10 17  1  0  0  0  0
 10 22  1  6  0  0  0
 11 15  1  0  0  0  0
 11 23  1  6  0  0  0
 12 15  1  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  6  0  0  0
 19 25  1  1  0  0  0
 25 27  2  0  0  0  0
 26 31  1  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
 29 33  1  0  0  0  0
 29 35  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

HMDB0015386
     RDKit          3D
Retapamulin
 83 87  0  0  0  0  0  0  0  0999 V2000
   -3.9015   -2.7975    2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -2.2270    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -2.0215    0.1019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7652   -3.4719   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -1.3948   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -0.1823    0.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3719   -0.1816    0.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.3314    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8806   -0.4844    2.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.3197    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872   -0.1037   -0.8682 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8908   -0.0956   -1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606   -1.4370   -0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -1.4141   -0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3086   -1.5154    0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -0.1582    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9169    0.7108    0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4952    1.0369   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895   -0.0984   -0.9466 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9325   -0.1687   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221    1.1456   -0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4933    1.8786   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    2.0421    1.1065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0710    1.3921    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    2.9342    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379    2.0984    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.0488   -0.4179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0549    1.4244   -1.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    2.5684   -2.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649    2.2747   -1.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    2.9841   -2.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    1.0957   -1.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6117   -0.2485    0.0936 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1425   -0.2738   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489   -1.4634   -0.5195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0442   -2.4578   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352   -2.9120    3.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787   -3.1331    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -1.9305    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084   -3.8872   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5595   -4.0821    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7562   -3.4467   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641   -2.1977   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860   -1.3657   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -0.3223    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -1.2912    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    0.5367    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.1381   -2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2213   -2.1249   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446   -1.8033    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757   -2.1566   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8027   -2.3547    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -1.5718    0.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841   -0.3142    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    0.1671    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5119    1.6197    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028    1.9386   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.3190    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2973    0.1296    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2597   -1.1991   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550    0.5129   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5157   -1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    1.6329   -0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    2.9780   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    2.8036    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    2.1498    3.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821    0.5027    2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.2850    2.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830    3.4746    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9365    3.7235    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912    2.7675    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5973    1.6215    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0262    1.8035   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1571    0.5788   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228    3.5657   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139    2.5089   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700    0.2489   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4989   -0.2728    1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134    0.5852    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4559   -1.1811    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452   -0.4590   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -1.3541   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414   -2.5353   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 27 26  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  3  1  0
 18 12  1  0
 32 21  1  0
 19 14  1  0
 32 27  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  1
 10 46  1  0
 10 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  6
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  1
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 32 77  1  6
 33 78  1  1
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  6
 36 83  1  0
M  END

6918462
  Mrv0541 02231215212D          

 36 40  0  0  1  0            999 V2000
    5.1111    0.5988    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -1.5522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5002   -3.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749   -4.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9632   -0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050   -4.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6903   -3.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6903   -2.9094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2059   -4.0609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4050   -2.4969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1195   -3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323   -4.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -2.2587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1195   -2.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -4.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7054   -3.4288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4165   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040   -2.6296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9625   -2.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059   -2.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6048   -4.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4220   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1063   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383   -0.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567    3.3124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1558    3.5107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6851    1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5539    4.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530    5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502    2.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 14  2  1  6  0  0  0
  2 26  1  0  0  0  0
 17  3  1  1  0  0  0
  4 16  2  0  0  0  0
  5 26  2  0  0  0  0
 28  6  1  6  0  0  0
 29  6  1  1  0  0  0
  6 36  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
  8 16  1  1  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 21  1  1  0  0  0
 10 17  1  0  0  0  0
 10 22  1  6  0  0  0
 11 15  1  0  0  0  0
 11 23  1  6  0  0  0
 12 15  1  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  6  0  0  0
 19 25  1  1  0  0  0
 25 27  2  0  0  0  0
 26 31  1  0  0  0  0
 28 32  1  0  0  0  0
 28 34  1  0  0  0  0
 29 33  1  0  0  0  0
 29 35  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015386

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC1C[C@@H]2CC[C@H](C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1

> <INCHI_KEY>
STZYTFJPGGDRJD-FJJJPKKESA-N

> <FORMULA>
C30H47NO4S

> <MOLECULAR_WEIGHT>
517.763

> <EXACT_MASS>
517.322579687

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
59.491879736699914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
4.373434360666666

> <ALOGPS_LOGS>
-6.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.235285869121373

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.425538704648119

> <JCHEM_PKA_STRONGEST_BASIC>
9.686419413341952

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
145.45149999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retapamulin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015386
     RDKit          3D
Retapamulin
 83 87  0  0  0  0  0  0  0  0999 V2000
   -3.9015   -2.7975    2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -2.2270    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -2.0215    0.1019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7652   -3.4719   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -1.3948   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -0.1823    0.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3719   -0.1816    0.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.3314    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8806   -0.4844    2.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.3197    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872   -0.1037   -0.8682 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8908   -0.0956   -1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606   -1.4370   -0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -1.4141   -0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3086   -1.5154    0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -0.1582    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9169    0.7108    0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4952    1.0369   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895   -0.0984   -0.9466 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9325   -0.1687   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221    1.1456   -0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4933    1.8786   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    2.0421    1.1065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0710    1.3921    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    2.9342    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379    2.0984    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.0488   -0.4179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0549    1.4244   -1.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    2.5684   -2.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649    2.2747   -1.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    2.9841   -2.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    1.0957   -1.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6117   -0.2485    0.0936 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1425   -0.2738   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489   -1.4634   -0.5195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0442   -2.4578   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352   -2.9120    3.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787   -3.1331    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -1.9305    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084   -3.8872   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5595   -4.0821    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7562   -3.4467   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641   -2.1977   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860   -1.3657   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -0.3223    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -1.2912    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    0.5367    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.1381   -2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2213   -2.1249   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446   -1.8033    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757   -2.1566   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8027   -2.3547    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -1.5718    0.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841   -0.3142    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    0.1671    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5119    1.6197    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028    1.9386   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.3190    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2973    0.1296    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2597   -1.1991   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550    0.5129   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5157   -1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    1.6329   -0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    2.9780   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    2.8036    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    2.1498    3.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821    0.5027    2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.2850    2.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830    3.4746    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9365    3.7235    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912    2.7675    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5973    1.6215    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0262    1.8035   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1571    0.5788   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228    3.5657   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139    2.5089   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700    0.2489   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4989   -0.2728    1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134    0.5852    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4559   -1.1811    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452   -0.4590   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -1.3541   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414   -2.5353   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 27 26  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  3  1  0
 18 12  1  0
 32 21  1  0
 19 14  1  0
 32 27  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  1
 10 46  1  0
 10 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  6
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  1
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 32 77  1  6
 33 78  1  1
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  6
 36 83  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6918462                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.541   1.118   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.847  -2.897   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.000  -6.813   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.113  -7.681   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.131  -1.520   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       4.399   5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      10.089  -7.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.755  -6.971   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.755  -5.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.584  -7.580   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.089  -4.661   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.423  -6.971   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.767  -9.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.642  -4.216   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.423  -5.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.620  -7.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.517  -6.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.244  -9.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.327  -4.909   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.130  -3.999   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.291  -4.953   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.329  -8.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.089  -3.121   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.854  -4.708   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.265  -3.687   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.591  -1.549   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.676  -2.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.386   6.183   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.891   6.553   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.746   2.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.796  -0.230   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.345   3.855   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.211   2.569   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.501   9.026   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.006   9.396   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.080   4.595   0.000  0.00  0.00           C+0
CONECT    1   30   31                                                       
CONECT    2   14   26                                                       
CONECT    3   17                                                            
CONECT    4   16                                                            
CONECT    5   26                                                            
CONECT    6   28   29   36                                                  
CONECT    7    8   10   12   13                                             
CONECT    8    7    9   16                                                  
CONECT    9    8   11   14   21                                             
CONECT   10    7   17   22                                                  
CONECT   11    9   15   23                                                  
CONECT   12    7   15                                                       
CONECT   13    7   18                                                       
CONECT   14    2    9   20                                                  
CONECT   15   11   12                                                       
CONECT   16    4    8   18                                                  
CONECT   17    3   10   19                                                  
CONECT   18   13   16                                                       
CONECT   19   17   20   24   25                                             
CONECT   20   14   19                                                       
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   19                                                            
CONECT   25   19   27                                                       
CONECT   26    2    5   31                                                  
CONECT   27   25                                                            
CONECT   28    6   32   34                                                  
CONECT   29    6   33   35                                                  
CONECT   30    1   32   33                                                  
CONECT   31    1   26                                                       
CONECT   32   28   30                                                       
CONECT   33   29   30                                                       
CONECT   34   28   35                                                       
CONECT   35   29   34                                                       
CONECT   36    6                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0015386
HETATM    1  C1  UNL     1      -3.902  -2.798   2.160  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.856  -2.227   1.567  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.825  -2.022   0.102  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.765  -3.472  -0.465  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.542  -1.395  -0.364  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.063  -0.182   0.327  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.372  -0.182   0.152  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.278  -0.331   1.157  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.881  -0.484   2.334  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.761  -0.320   0.904  1.00  0.00           C  
HETATM   11  S1  UNL     1       3.087  -0.104  -0.868  1.00  0.00           S  
HETATM   12  C9  UNL     1       4.891  -0.096  -1.127  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.461  -1.437  -0.798  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.945  -1.414  -0.638  1.00  0.00           C  
HETATM   15  C12 UNL     1       7.309  -1.515   0.839  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.835  -0.158   1.349  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.917   0.711   0.129  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.495   1.037  -0.332  1.00  0.00           C  
HETATM   19  N1  UNL     1       7.489  -0.098  -0.947  1.00  0.00           N  
HETATM   20  C16 UNL     1       8.933  -0.169  -0.833  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.622   1.146  -0.061  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.493   1.879  -0.817  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.911   2.042   1.107  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.071   1.392   2.433  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.124   2.934   0.873  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.338   2.098   0.644  1.00  0.00           C  
HETATM   27  C23 UNL     1      -4.128   1.049  -0.418  1.00  0.00           C  
HETATM   28  C24 UNL     1      -5.055   1.424  -1.585  1.00  0.00           C  
HETATM   29  C25 UNL     1      -4.324   2.568  -2.199  1.00  0.00           C  
HETATM   30  C26 UNL     1      -2.865   2.275  -1.927  1.00  0.00           C  
HETATM   31  O3  UNL     1      -2.026   2.984  -2.441  1.00  0.00           O  
HETATM   32  C27 UNL     1      -2.766   1.096  -1.025  1.00  0.00           C  
HETATM   33  C28 UNL     1      -4.612  -0.248   0.094  1.00  0.00           C  
HETATM   34  C29 UNL     1      -6.143  -0.274  -0.082  1.00  0.00           C  
HETATM   35  C30 UNL     1      -4.049  -1.463  -0.519  1.00  0.00           C  
HETATM   36  O4  UNL     1      -5.044  -2.458  -0.486  1.00  0.00           O  
HETATM   37  H1  UNL     1      -3.835  -2.912   3.259  1.00  0.00           H  
HETATM   38  H2  UNL     1      -4.779  -3.133   1.662  1.00  0.00           H  
HETATM   39  H3  UNL     1      -2.046  -1.931   2.229  1.00  0.00           H  
HETATM   40  H4  UNL     1      -1.808  -3.887  -0.090  1.00  0.00           H  
HETATM   41  H5  UNL     1      -3.560  -4.082   0.000  1.00  0.00           H  
HETATM   42  H6  UNL     1      -2.756  -3.447  -1.553  1.00  0.00           H  
HETATM   43  H7  UNL     1      -0.764  -2.198  -0.128  1.00  0.00           H  
HETATM   44  H8  UNL     1      -1.486  -1.366  -1.469  1.00  0.00           H  
HETATM   45  H9  UNL     1      -1.183  -0.322   1.419  1.00  0.00           H  
HETATM   46  H10 UNL     1       3.153  -1.291   1.252  1.00  0.00           H  
HETATM   47  H11 UNL     1       3.236   0.537   1.410  1.00  0.00           H  
HETATM   48  H12 UNL     1       5.031   0.138  -2.222  1.00  0.00           H  
HETATM   49  H13 UNL     1       5.221  -2.125  -1.660  1.00  0.00           H  
HETATM   50  H14 UNL     1       4.945  -1.803   0.118  1.00  0.00           H  
HETATM   51  H15 UNL     1       7.476  -2.157  -1.256  1.00  0.00           H  
HETATM   52  H16 UNL     1       6.803  -2.355   1.327  1.00  0.00           H  
HETATM   53  H17 UNL     1       8.406  -1.572   0.884  1.00  0.00           H  
HETATM   54  H18 UNL     1       5.784  -0.314   1.670  1.00  0.00           H  
HETATM   55  H19 UNL     1       7.431   0.167   2.200  1.00  0.00           H  
HETATM   56  H20 UNL     1       7.512   1.620   0.278  1.00  0.00           H  
HETATM   57  H21 UNL     1       5.603   1.939  -0.999  1.00  0.00           H  
HETATM   58  H22 UNL     1       4.895   1.319   0.531  1.00  0.00           H  
HETATM   59  H23 UNL     1       9.297   0.130   0.163  1.00  0.00           H  
HETATM   60  H24 UNL     1       9.260  -1.199  -1.094  1.00  0.00           H  
HETATM   61  H25 UNL     1       9.355   0.513  -1.595  1.00  0.00           H  
HETATM   62  H26 UNL     1      -0.340   1.516  -1.820  1.00  0.00           H  
HETATM   63  H27 UNL     1       0.441   1.633  -0.232  1.00  0.00           H  
HETATM   64  H28 UNL     1      -0.577   2.978  -0.685  1.00  0.00           H  
HETATM   65  H29 UNL     1      -1.080   2.804   1.278  1.00  0.00           H  
HETATM   66  H30 UNL     1      -2.607   2.150   3.086  1.00  0.00           H  
HETATM   67  H31 UNL     1      -2.682   0.503   2.495  1.00  0.00           H  
HETATM   68  H32 UNL     1      -1.089   1.285   2.983  1.00  0.00           H  
HETATM   69  H33 UNL     1      -3.283   3.475   1.851  1.00  0.00           H  
HETATM   70  H34 UNL     1      -2.936   3.723   0.127  1.00  0.00           H  
HETATM   71  H35 UNL     1      -5.191   2.768   0.415  1.00  0.00           H  
HETATM   72  H36 UNL     1      -4.597   1.622   1.629  1.00  0.00           H  
HETATM   73  H37 UNL     1      -6.026   1.804  -1.210  1.00  0.00           H  
HETATM   74  H38 UNL     1      -5.157   0.579  -2.294  1.00  0.00           H  
HETATM   75  H39 UNL     1      -4.623   3.566  -1.879  1.00  0.00           H  
HETATM   76  H40 UNL     1      -4.514   2.509  -3.310  1.00  0.00           H  
HETATM   77  H41 UNL     1      -2.670   0.249  -1.729  1.00  0.00           H  
HETATM   78  H42 UNL     1      -4.499  -0.273   1.197  1.00  0.00           H  
HETATM   79  H43 UNL     1      -6.613   0.585   0.413  1.00  0.00           H  
HETATM   80  H44 UNL     1      -6.456  -1.181   0.510  1.00  0.00           H  
HETATM   81  H45 UNL     1      -6.445  -0.459  -1.113  1.00  0.00           H  
HETATM   82  H46 UNL     1      -3.835  -1.354  -1.610  1.00  0.00           H  
HETATM   83  H47 UNL     1      -5.541  -2.535  -1.317  1.00  0.00           H  
CONECT    1    2    2   37   38
CONECT    2    3   39
CONECT    3    4    5   35
CONECT    4   40   41   42
CONECT    5    6   43   44
CONECT    6    7   21   45
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   46   47
CONECT   11   12
CONECT   12   13   18   48
CONECT   13   14   49   50
CONECT   14   15   19   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   19   56
CONECT   18   57   58
CONECT   19   20
CONECT   20   59   60   61
CONECT   21   22   23   32
CONECT   22   62   63   64
CONECT   23   24   25   65
CONECT   24   66   67   68
CONECT   25   26   69   70
CONECT   26   27   71   72
CONECT   27   28   32   33
CONECT   28   29   73   74
CONECT   29   30   75   76
CONECT   30   31   31   32
CONECT   32   77
CONECT   33   34   35   78
CONECT   34   79   80   81
CONECT   35   36   82
CONECT   36   83
END

HMDB0015386
     RDKit          3D
Retapamulin
 83 87  0  0  0  0  0  0  0  0999 V2000
   -3.9015   -2.7975    2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -2.2270    1.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -2.0215    0.1019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7652   -3.4719   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -1.3948   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -0.1823    0.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3719   -0.1816    0.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.3314    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8806   -0.4844    2.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.3197    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872   -0.1037   -0.8682 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8908   -0.0956   -1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606   -1.4370   -0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9454   -1.4141   -0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3086   -1.5154    0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -0.1582    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9169    0.7108    0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4952    1.0369   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895   -0.0984   -0.9466 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9325   -0.1687   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221    1.1456   -0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4933    1.8786   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    2.0421    1.1065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0710    1.3921    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237    2.9342    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379    2.0984    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.0488   -0.4179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0549    1.4244   -1.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    2.5684   -2.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8649    2.2747   -1.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    2.9841   -2.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    1.0957   -1.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6117   -0.2485    0.0936 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1425   -0.2738   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489   -1.4634   -0.5195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0442   -2.4578   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352   -2.9120    3.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787   -3.1331    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -1.9305    2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084   -3.8872   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5595   -4.0821    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7562   -3.4467   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641   -2.1977   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860   -1.3657   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -0.3223    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -1.2912    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    0.5367    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.1381   -2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2213   -2.1249   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446   -1.8033    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757   -2.1566   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8027   -2.3547    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -1.5718    0.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841   -0.3142    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    0.1671    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5119    1.6197    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028    1.9386   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.3190    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2973    0.1296    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2597   -1.1991   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550    0.5129   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5157   -1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    1.6329   -0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    2.9780   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    2.8036    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    2.1498    3.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821    0.5027    2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.2850    2.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830    3.4746    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9365    3.7235    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1912    2.7675    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5973    1.6215    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0262    1.8035   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1571    0.5788   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228    3.5657   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139    2.5089   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700    0.2489   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4989   -0.2728    1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134    0.5852    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4559   -1.1811    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452   -0.4590   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -1.3541   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414   -2.5353   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 27 26  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  3  1  0
 18 12  1  0
 32 21  1  0
 19 14  1  0
 32 27  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  1
 10 46  1  0
 10 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  6
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  1
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 32 77  1  6
 33 78  1  1
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  6
 36 83  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SB 275833	HMDB
Altabax	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetic acid	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulphanyl}acetate	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulphanyl}acetic acid	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetic acid	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulphanyl}acetate	HMDB
(1S,2R,3S,4S,6R,7R,8R,14R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulphanyl}acetic acid	HMDB
Retapamulin	MeSH

Chemical Formula

C₃₀H₄₇NO₄S

Average Molecular Weight

517.763

Monoisotopic Molecular Weight

517.322579687

IUPAC Name

(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate

Traditional Name

retapamulin

CAS Registry Number

224452-66-8

SMILES

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC1C[C@@H]2CC[C@H](C1)N2C

InChI Identifier

InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1

InChI Key

STZYTFJPGGDRJD-FJJJPKKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Pleuromutilin and derivatives

Alternative Parents

Substituents

Pleuromutilin
Tropane alkaloid
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Thioether
Azacycle
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Monocarboxylic acid or derivatives
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015386)
Extracellular (HMDB: HMDB0015386)

Source

Exogenous

Exogenous (HMDB: HMDB0015386)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00039 g/L	Not Available
LogP	5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00039 g/L	ALOGPS
logP	4.63	ALOGPS
logP	4.37	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.45 m³·mol⁻¹	ChemAxon
Polarizability	59.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	250.37	30932474
DeepCCS	[M+Na]+	224.143	30932474
AllCCS	[M+H]+	227.9	32859911
AllCCS	[M+H-H2O]+	226.6	32859911
AllCCS	[M+NH4]+	228.9	32859911
AllCCS	[M+Na]+	229.2	32859911
AllCCS	[M-H]-	203.6	32859911
AllCCS	[M+Na-2H]-	205.9	32859911
AllCCS	[M+HCOO]-	208.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retapamulin	C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC1C[C@@H]2CC[C@H](C1)N2C	2882.3	Standard polar	33892256
Retapamulin	C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC1C[C@@H]2CC[C@H](C1)N2C	3652.2	Standard non polar	33892256
Retapamulin	C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC1C[C@@H]2CC[C@H](C1)N2C	4034.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retapamulin,1TMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C	3769.6	Semi standard non polar	33892256
Retapamulin,1TMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O	3645.2	Semi standard non polar	33892256
Retapamulin,1TMS,isomer #3	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O	3779.8	Semi standard non polar	33892256
Retapamulin,2TMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C	3617.1	Semi standard non polar	33892256
Retapamulin,2TMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C	3628.9	Standard non polar	33892256
Retapamulin,2TMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C	4331.4	Standard polar	33892256
Retapamulin,2TMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C	3730.8	Semi standard non polar	33892256
Retapamulin,2TMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C	3520.5	Standard non polar	33892256
Retapamulin,2TMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C	4281.7	Standard polar	33892256
Retapamulin,1TBDMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	3994.2	Semi standard non polar	33892256
Retapamulin,1TBDMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O	3877.2	Semi standard non polar	33892256
Retapamulin,1TBDMS,isomer #3	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C(C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O	3990.9	Semi standard non polar	33892256
Retapamulin,2TBDMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	4054.4	Semi standard non polar	33892256
Retapamulin,2TBDMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	4062.1	Standard non polar	33892256
Retapamulin,2TBDMS,isomer #1	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)CC[C@@]3(CC[C@H]2C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	4509.4	Standard polar	33892256
Retapamulin,2TBDMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C(C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	4153.8	Semi standard non polar	33892256
Retapamulin,2TBDMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C(C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	3830.1	Standard non polar	33892256
Retapamulin,2TBDMS,isomer #2	C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3(CC=C(O[Si](C)(C)C(C)(C)C)[C@H]32)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C	4448.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Retapamulin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-9711120000-fcdfffe2635f8f75be04	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retapamulin GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9551060000-42bdf7a4a7e4a697f8d3	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 10V, Positive-QTOF	splash10-1000-0912070000-67b87f331f6188105b85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 20V, Positive-QTOF	splash10-0udj-7948240000-c7e591627af7f54b3685	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 40V, Positive-QTOF	splash10-0a4l-4900000000-e32d32923adfee80b8d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 10V, Negative-QTOF	splash10-014i-0709150000-8b404ff35785559f3a6c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 20V, Negative-QTOF	splash10-0600-0905010000-eb22b08bf5106978dbe9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 40V, Negative-QTOF	splash10-00xr-9737000000-0c83dbfb5064e95dbe86	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 10V, Positive-QTOF	splash10-0gb9-0312190000-34064f2cad0ea14ddea8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 20V, Positive-QTOF	splash10-0gi1-0920440000-c27556e56d29a64cf689	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 40V, Positive-QTOF	splash10-00di-4900000000-49114c3baf9b395b57fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 10V, Negative-QTOF	splash10-066r-1005090000-f70e4d716b40fb2a11ca	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 20V, Negative-QTOF	splash10-06di-7900170000-e86bae12bb724e8a2917	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retapamulin 40V, Negative-QTOF	splash10-0udj-5921120000-62814e58892726823fd7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01256	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01256	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293659

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Retapamulin

METLIN ID

Not Available

PubChem Compound

6918462

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jones RN, Fritsche TR, Sader HS, Ross JE: Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci. Antimicrob Agents Chemother. 2006 Jul;50(7):2583-6. [PubMed:16801451 ]
Jacobs MR: Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children. Future Microbiol. 2007 Dec;2(6):591-600. [PubMed:18041900 ]
Parish LC, Parish JL: Retapamulin: a new topical antibiotic for the treatment of uncomplicated skin infections. Drugs Today (Barc). 2008 Feb;44(2):91-102. doi: 10.1358/dot.2008.44.2.1153446. [PubMed:18389088 ]
Yang LP, Keam SJ: Retapamulin: a review of its use in the management of impetigo and other uncomplicated superficial skin infections. Drugs. 2008;68(6):855-73. [PubMed:18416589 ]
Authors unspecified: Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. doi: 10.1136/dtb.2008.09.0023. [PubMed:18832258 ]
Shawar R, Scangarella-Oman N, Dalessandro M, Breton J, Twynholm M, Li G, Garges H: Topical retapamulin in the management of infected traumatic skin lesions. Ther Clin Risk Manag. 2009 Feb;5(1):41-9. Epub 2009 Mar 26. [PubMed:19436611 ]
Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. doi: 10.4103/0378-6323.58693. [PubMed:20061745 ]
Novak R, Shlaes DM: The pleuromutilin antibiotics: a new class for human use. Curr Opin Investig Drugs. 2010 Feb;11(2):182-91. [PubMed:20112168 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. 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.
CenterWatch [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

Showing metabocard for Retapamulin (HMDB0015386)

MOL for HMDB0015386 (Retapamulin)

3D MOL for HMDB0015386 (Retapamulin)

3D SDF for HMDB0015386 (Retapamulin)

3D-SDF for HMDB0015386 (Retapamulin)

PDB for HMDB0015386 (Retapamulin)

3D PDB for HMDB0015386 (Retapamulin)

SMILES for HMDB0015386 (Retapamulin)

INCHI for HMDB0015386 (Retapamulin)

Structure for HMDB0015386 (Retapamulin)

3D Structure for HMDB0015386 (Retapamulin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes