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

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

HMDB0015418

Secondary Accession Numbers

HMDB15418

Metabolite Identification

Common Name

Josamycin

Description

Josamycin is only found in individuals that have used or taken this drug. It is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens. [PubChem]The mechanism of action of macrolides such as Josamycin is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, thereby inhibiting translocation of peptidyl tRNA. This action is mainly bacteriostatic, but can also be bactericidal in high concentrations. Macrolides tend to accumulate within leukocytes, and are therefore actually transported into the site of infection.

Structure

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

1321
  Mrv0541 02231215232D          

 58 60  0  0  1  0            999 V2000
    5.9370    2.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    2.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    1.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4450   -0.7215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4022    1.3732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1396   -3.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4469   -0.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4231   -0.6476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0429   -1.0174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7826    1.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.1825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6515    1.9451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0804    1.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6515    1.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0805    1.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2075   -0.0070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7935    1.9451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2224    1.9451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6240   -0.5904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    2.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    0.7075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0325   -0.0070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8376   -1.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4251   -2.1017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8271   -0.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6158    0.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3810    2.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1396   -2.5142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4127    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6001   -2.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2437   -0.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8540   -2.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6324   -0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6262   -0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9856    1.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5685   -2.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0065   -1.2309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7721    2.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7120   -2.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2830   -2.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9975   -2.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8035   -1.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
 24  1  1  6  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21  3  1  6  0  0  0
 22  3  1  6  0  0  0
  4 24  1  0  0  0  0
  4 28  1  0  0  0  0
 19  5  1  1  0  0  0
 23  6  1  6  0  0  0
 27  7  1  6  0  0  0
  7 43  1  0  0  0  0
 29  8  1  6  0  0  0
  8 45  1  0  0  0  0
 34  9  1  6  0  0  0
  9 48  1  0  0  0  0
 39 10  1  6  0  0  0
 11 42  2  0  0  0  0
 12 46  1  0  0  0  0
 12 51  1  0  0  0  0
 13 43  2  0  0  0  0
 14 46  2  0  0  0  0
 15 48  2  0  0  0  0
 17 16  1  6  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 31  1  6  0  0  0
 22 25  1  0  0  0  0
 22 29  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
 23 35  1  0  0  0  0
 24 26  1  0  0  0  0
 25 30  1  0  0  0  0
 25 33  1  6  0  0  0
 27 28  1  0  0  0  0
 28 38  1  1  0  0  0
 29 34  1  0  0  0  0
 30 32  1  0  0  0  0
 32 39  1  0  0  0  0
 32 41  1  6  0  0  0
 33 42  1  0  0  0  0
 34 40  1  0  0  0  0
 39 44  1  0  0  0  0
 40 46  1  0  0  0  0
 43 47  1  0  0  0  0
 44 50  2  0  0  0  0
 47 49  1  0  0  0  0
 48 52  1  0  0  0  0
 49 53  1  0  0  0  0
 49 54  1  0  0  0  0
 50 56  1  0  0  0  0
 51 55  1  0  0  0  0
 51 58  1  6  0  0  0
 55 57  1  0  0  0  0
 56 57  2  0  0  0  0
M  END

HMDB0015418
     RDKit          3D
Josamycin
127129  0  0  0  0  0  0  0  0999 V2000
   -5.3214    0.7796    2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1009    0.9945    2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    0.7467    0.8006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.3803    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9497   -0.4001    1.3524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814   -0.0160    0.7541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0887   -1.1505    0.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -0.6979   -0.3361 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7843   -1.8306   -0.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918    0.2605    0.4176 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0536    0.6035   -0.3688 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2839    0.1059    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9400   -0.7608   -0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4354   -0.4696   -1.0134 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1457   -1.5837   -1.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051    0.7232   -1.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9962   -0.3950    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3345    0.0369    0.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3949   -0.7498    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1274   -1.9059    1.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957   -0.3475    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4188   -0.8024   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8837   -0.4027   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7223   -0.0854   -1.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2099    0.6220    1.2006 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6907   -0.0636    2.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1579    1.1479    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    1.4485    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8937    2.4146    1.5067 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    2.0319    2.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    3.3096    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292    0.9515    1.6215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8249    1.9587    2.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -1.7339    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6110   -2.5259    1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2176   -2.6973    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996   -3.5750    1.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -1.8525   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264   -3.2995   -0.4596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2886   -3.7478    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867   -3.3078   -1.6533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7003   -3.1567   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9215   -2.4680   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6253   -1.6428   -3.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0394   -1.3346   -3.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6674   -0.6150   -2.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9617    0.0360   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2101    1.5261   -1.2817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7507    1.8426    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0860    2.1958   -1.6618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9215    2.6858   -1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7960    3.8750   -0.8700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399    1.9568   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8506    1.9672   -0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9766    3.1846    0.6441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394    4.1609    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2828    5.3875    1.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9712    3.9480    0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7080   -0.2556    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0938    1.5296    2.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920    0.9664    3.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0378    0.3691    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -0.1133   -0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702    0.3678   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -0.1113   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -2.5677   -1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5080   -2.3282   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3246   -1.5220   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859   -0.3297    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639   -0.5175    0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5506   -0.6317   -1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178   -1.8529   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4469   -2.1239   -2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0600   -1.2587   -2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4591   -2.3301   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    0.9835   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9241   -1.4122    0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8893    0.7611    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3670   -0.8098    1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3037   -1.8749   -0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4801   -1.2559   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0527    0.5065   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1631   -0.2101   -1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4118   -0.8445   -2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4043    0.6201   -2.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8406    0.4800   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8358    1.4781    1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4222    0.0887    3.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -1.1532    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.3186    2.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026    1.8543   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485    2.5461    3.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646    0.9500    2.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    2.3807    2.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176    4.3165    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    3.3764    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7247    2.9158   -0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    0.3536    2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364    2.8154    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -2.3293   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2669   -2.1289    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520   -3.5628    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139   -2.1083    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8620   -1.3837   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57127  1  0
M  END

1321
  Mrv0541 02231215232D          

 58 60  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0015418

> <DATABASE_NAME>
hmdb

> <SMILES>
CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

> <INCHI_KEY>
XJSFLOJWULLJQS-NGVXBBESSA-N

> <FORMULA>
C42H69NO15

> <MOLECULAR_WEIGHT>
827.995

> <EXACT_MASS>
827.466720543

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
87.9124512169313

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.2163761246666676

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.50376924800512

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.668262250875994

> <JCHEM_PKA_STRONGEST_BASIC>
7.895227495034379

> <JCHEM_POLAR_SURFACE_AREA>
206.05

> <JCHEM_REFRACTIVITY>
211.03350000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
josamycin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015418
     RDKit          3D
Josamycin
127129  0  0  0  0  0  0  0  0999 V2000
   -5.3214    0.7796    2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1009    0.9945    2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    0.7467    0.8006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.3803    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0887   -1.1505    0.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0536    0.6035   -0.3688 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1321                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082   4.401   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.750   1.321   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.417   1.321   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.748   2.091   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.417   4.401   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.541   3.631   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.747   1.321   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      19.497  -1.347   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      19.417   2.563   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.061  -6.233   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      12.034  -1.394   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      23.190  -1.209   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.081  -0.990   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      20.613  -1.899   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      21.994   3.254   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      13.750   5.941   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      13.750   4.401   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   3.631   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.083   3.631   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   2.091   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.084   2.091   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.187  -0.013   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081   3.631   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748   3.631   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.098  -1.102   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.415   4.401   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.081   2.091   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.415   1.321   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.727  -0.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.497  -2.590   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.082   1.321   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.727  -3.923   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.611  -0.704   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.816   1.076   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.311   4.964   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.083   6.711   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.416   6.711   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.415  -0.219   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.061  -4.693   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.304   0.677   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.187  -3.923   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.522  -1.792   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.747  -0.219   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.394  -3.923   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.980  -1.614   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      21.702  -0.810   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.414  -0.989   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      20.506   3.653   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.414  -2.530   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      19.728  -4.693   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      24.279  -2.298   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      20.108   5.140   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.080  -3.300   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.748  -3.300   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      23.729  -3.923   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      21.062  -3.923   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      22.395  -4.693   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      25.767  -1.899   0.000  0.00  0.00           C+0
CONECT    1   18   24                                                       
CONECT    2   20   21                                                       
CONECT    3   21   22                                                       
CONECT    4   24   28                                                       
CONECT    5   19                                                            
CONECT    6   23                                                            
CONECT    7   27   43                                                       
CONECT    8   29   45                                                       
CONECT    9   34   48                                                       
CONECT   10   39                                                            
CONECT   11   42                                                            
CONECT   12   46   51                                                       
CONECT   13   43                                                            
CONECT   14   46                                                            
CONECT   15   48                                                            
CONECT   16   17   36   37                                                  
CONECT   17   16   18   19                                                  
CONECT   18    1   17   20                                                  
CONECT   19    5   17   21                                                  
CONECT   20    2   18   31                                                  
CONECT   21    2    3   19                                                  
CONECT   22    3   25   29                                                  
CONECT   23    6   26   27   35                                             
CONECT   24    1    4   26                                                  
CONECT   25   22   30   33                                                  
CONECT   26   23   24                                                       
CONECT   27    7   23   28                                                  
CONECT   28    4   27   38                                                  
CONECT   29    8   22   34                                                  
CONECT   30   25   32                                                       
CONECT   31   20                                                            
CONECT   32   30   39   41                                                  
CONECT   33   25   42                                                       
CONECT   34    9   29   40                                                  
CONECT   35   23                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   28                                                            
CONECT   39   10   32   44                                                  
CONECT   40   34   46                                                       
CONECT   41   32                                                            
CONECT   42   11   33                                                       
CONECT   43    7   13   47                                                  
CONECT   44   39   50                                                       
CONECT   45    8                                                            
CONECT   46   12   14   40                                                  
CONECT   47   43   49                                                       
CONECT   48    9   15   52                                                  
CONECT   49   47   53   54                                                  
CONECT   50   44   56                                                       
CONECT   51   12   55   58                                                  
CONECT   52   48                                                            
CONECT   53   49                                                            
CONECT   54   49                                                            
CONECT   55   51   57                                                       
CONECT   56   50   57                                                       
CONECT   57   55   56                                                       
CONECT   58   51                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

COMPND    HMDB0015418
HETATM    1  C1  UNL     1      -5.321   0.780   2.732  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.101   0.995   2.141  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.019   0.747   0.801  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.064  -0.380   0.501  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.950  -0.400   1.352  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.781  -0.016   0.754  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.089  -1.151   0.581  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.064  -0.698  -0.336  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.784  -1.831  -0.983  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.992   0.261   0.418  1.00  0.00           C  
HETATM   11  O4  UNL     1       3.054   0.604  -0.369  1.00  0.00           O  
HETATM   12  C8  UNL     1       4.284   0.106   0.067  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.940  -0.761  -0.953  1.00  0.00           C  
HETATM   14  C10 UNL     1       6.435  -0.470  -1.013  1.00  0.00           C  
HETATM   15  C11 UNL     1       7.146  -1.584  -1.749  1.00  0.00           C  
HETATM   16  O5  UNL     1       6.705   0.723  -1.668  1.00  0.00           O  
HETATM   17  C12 UNL     1       6.996  -0.395   0.400  1.00  0.00           C  
HETATM   18  O6  UNL     1       8.335   0.037   0.331  1.00  0.00           O  
HETATM   19  C13 UNL     1       9.395  -0.750   0.761  1.00  0.00           C  
HETATM   20  O7  UNL     1       9.127  -1.906   1.228  1.00  0.00           O  
HETATM   21  C14 UNL     1      10.796  -0.347   0.716  1.00  0.00           C  
HETATM   22  C15 UNL     1      11.419  -0.802  -0.588  1.00  0.00           C  
HETATM   23  C16 UNL     1      12.884  -0.403  -0.651  1.00  0.00           C  
HETATM   24  C17 UNL     1      10.722  -0.085  -1.730  1.00  0.00           C  
HETATM   25  C18 UNL     1       6.210   0.622   1.201  1.00  0.00           C  
HETATM   26  C19 UNL     1       5.691  -0.064   2.439  1.00  0.00           C  
HETATM   27  O8  UNL     1       5.158   1.148   0.439  1.00  0.00           O  
HETATM   28  C20 UNL     1       1.153   1.448   0.791  1.00  0.00           C  
HETATM   29  N1  UNL     1       1.894   2.415   1.507  1.00  0.00           N  
HETATM   30  C21 UNL     1       2.426   2.032   2.765  1.00  0.00           C  
HETATM   31  C22 UNL     1       2.682   3.310   0.731  1.00  0.00           C  
HETATM   32  C23 UNL     1      -0.029   0.951   1.621  1.00  0.00           C  
HETATM   33  O9  UNL     1      -0.825   1.959   2.068  1.00  0.00           O  
HETATM   34  C24 UNL     1      -3.651  -1.734   0.410  1.00  0.00           C  
HETATM   35  C25 UNL     1      -3.611  -2.526   1.724  1.00  0.00           C  
HETATM   36  C26 UNL     1      -2.218  -2.697   2.159  1.00  0.00           C  
HETATM   37  O10 UNL     1      -1.500  -3.575   1.649  1.00  0.00           O  
HETATM   38  C27 UNL     1      -4.957  -1.853  -0.271  1.00  0.00           C  
HETATM   39  C28 UNL     1      -5.426  -3.299  -0.460  1.00  0.00           C  
HETATM   40  C29 UNL     1      -6.289  -3.748   0.729  1.00  0.00           C  
HETATM   41  C30 UNL     1      -6.387  -3.308  -1.653  1.00  0.00           C  
HETATM   42  O11 UNL     1      -7.700  -3.157  -1.302  1.00  0.00           O  
HETATM   43  C31 UNL     1      -5.921  -2.468  -2.777  1.00  0.00           C  
HETATM   44  C32 UNL     1      -6.625  -1.643  -3.520  1.00  0.00           C  
HETATM   45  C33 UNL     1      -8.039  -1.335  -3.434  1.00  0.00           C  
HETATM   46  C34 UNL     1      -8.667  -0.615  -2.519  1.00  0.00           C  
HETATM   47  C35 UNL     1      -7.962   0.036  -1.354  1.00  0.00           C  
HETATM   48  C36 UNL     1      -8.210   1.526  -1.282  1.00  0.00           C  
HETATM   49  C37 UNL     1      -8.751   1.843   0.101  1.00  0.00           C  
HETATM   50  O12 UNL     1      -7.086   2.196  -1.662  1.00  0.00           O  
HETATM   51  C38 UNL     1      -5.922   2.686  -1.299  1.00  0.00           C  
HETATM   52  O13 UNL     1      -5.796   3.875  -0.870  1.00  0.00           O  
HETATM   53  C39 UNL     1      -4.640   1.957  -1.337  1.00  0.00           C  
HETATM   54  C40 UNL     1      -3.851   1.967  -0.056  1.00  0.00           C  
HETATM   55  O14 UNL     1      -3.977   3.185   0.644  1.00  0.00           O  
HETATM   56  C41 UNL     1      -3.039   4.161   0.740  1.00  0.00           C  
HETATM   57  C42 UNL     1      -3.283   5.387   1.513  1.00  0.00           C  
HETATM   58  O15 UNL     1      -1.971   3.948   0.135  1.00  0.00           O  
HETATM   59  H1  UNL     1      -5.708  -0.256   2.655  1.00  0.00           H  
HETATM   60  H2  UNL     1      -6.094   1.530   2.413  1.00  0.00           H  
HETATM   61  H3  UNL     1      -5.192   0.966   3.821  1.00  0.00           H  
HETATM   62  H4  UNL     1      -5.038   0.369   0.483  1.00  0.00           H  
HETATM   63  H5  UNL     1      -2.625  -0.113  -0.509  1.00  0.00           H  
HETATM   64  H6  UNL     1      -0.870   0.368  -0.259  1.00  0.00           H  
HETATM   65  H7  UNL     1       0.528  -0.111  -1.106  1.00  0.00           H  
HETATM   66  H8  UNL     1       1.014  -2.568  -1.303  1.00  0.00           H  
HETATM   67  H9  UNL     1       2.508  -2.328  -0.301  1.00  0.00           H  
HETATM   68  H10 UNL     1       2.325  -1.522  -1.902  1.00  0.00           H  
HETATM   69  H11 UNL     1       2.286  -0.330   1.332  1.00  0.00           H  
HETATM   70  H12 UNL     1       4.064  -0.517   0.976  1.00  0.00           H  
HETATM   71  H13 UNL     1       4.551  -0.632  -1.971  1.00  0.00           H  
HETATM   72  H14 UNL     1       4.818  -1.853  -0.696  1.00  0.00           H  
HETATM   73  H15 UNL     1       6.447  -2.124  -2.416  1.00  0.00           H  
HETATM   74  H16 UNL     1       8.060  -1.259  -2.257  1.00  0.00           H  
HETATM   75  H17 UNL     1       7.459  -2.330  -0.971  1.00  0.00           H  
HETATM   76  H18 UNL     1       5.987   0.983  -2.278  1.00  0.00           H  
HETATM   77  H19 UNL     1       6.924  -1.412   0.850  1.00  0.00           H  
HETATM   78  H20 UNL     1      10.889   0.761   0.792  1.00  0.00           H  
HETATM   79  H21 UNL     1      11.367  -0.810   1.570  1.00  0.00           H  
HETATM   80  H22 UNL     1      11.304  -1.875  -0.702  1.00  0.00           H  
HETATM   81  H23 UNL     1      13.480  -1.256  -0.218  1.00  0.00           H  
HETATM   82  H24 UNL     1      13.053   0.506  -0.053  1.00  0.00           H  
HETATM   83  H25 UNL     1      13.163  -0.210  -1.701  1.00  0.00           H  
HETATM   84  H26 UNL     1      10.412  -0.844  -2.469  1.00  0.00           H  
HETATM   85  H27 UNL     1      11.404   0.620  -2.264  1.00  0.00           H  
HETATM   86  H28 UNL     1       9.841   0.480  -1.391  1.00  0.00           H  
HETATM   87  H29 UNL     1       6.836   1.478   1.519  1.00  0.00           H  
HETATM   88  H30 UNL     1       6.422   0.089   3.261  1.00  0.00           H  
HETATM   89  H31 UNL     1       5.554  -1.153   2.219  1.00  0.00           H  
HETATM   90  H32 UNL     1       4.720   0.319   2.755  1.00  0.00           H  
HETATM   91  H33 UNL     1       0.703   1.854  -0.144  1.00  0.00           H  
HETATM   92  H34 UNL     1       1.949   2.546   3.631  1.00  0.00           H  
HETATM   93  H35 UNL     1       2.365   0.950   2.911  1.00  0.00           H  
HETATM   94  H36 UNL     1       3.494   2.381   2.786  1.00  0.00           H  
HETATM   95  H37 UNL     1       2.218   4.317   0.631  1.00  0.00           H  
HETATM   96  H38 UNL     1       3.713   3.376   1.113  1.00  0.00           H  
HETATM   97  H39 UNL     1       2.725   2.916  -0.324  1.00  0.00           H  
HETATM   98  H40 UNL     1       0.354   0.354   2.489  1.00  0.00           H  
HETATM   99  H41 UNL     1      -0.336   2.815   2.215  1.00  0.00           H  
HETATM  100  H42 UNL     1      -2.925  -2.329  -0.241  1.00  0.00           H  
HETATM  101  H43 UNL     1      -4.267  -2.129   2.492  1.00  0.00           H  
HETATM  102  H44 UNL     1      -3.952  -3.563   1.424  1.00  0.00           H  
HETATM  103  H45 UNL     1      -1.714  -2.108   2.922  1.00  0.00           H  
HETATM  104  H46 UNL     1      -5.822  -1.385   0.238  1.00  0.00           H  
HETATM  105  H47 UNL     1      -4.862  -1.384  -1.270  1.00  0.00           H  
HETATM  106  H48 UNL     1      -4.564  -3.972  -0.621  1.00  0.00           H  
HETATM  107  H49 UNL     1      -6.281  -3.003   1.546  1.00  0.00           H  
HETATM  108  H50 UNL     1      -5.985  -4.767   1.090  1.00  0.00           H  
HETATM  109  H51 UNL     1      -7.357  -3.865   0.454  1.00  0.00           H  
HETATM  110  H52 UNL     1      -6.310  -4.388  -2.022  1.00  0.00           H  
HETATM  111  H53 UNL     1      -8.268  -3.958  -1.422  1.00  0.00           H  
HETATM  112  H54 UNL     1      -4.834  -2.594  -2.962  1.00  0.00           H  
HETATM  113  H55 UNL     1      -6.041  -1.136  -4.338  1.00  0.00           H  
HETATM  114  H56 UNL     1      -8.682  -1.734  -4.243  1.00  0.00           H  
HETATM  115  H57 UNL     1      -9.740  -0.432  -2.526  1.00  0.00           H  
HETATM  116  H58 UNL     1      -8.233  -0.415  -0.406  1.00  0.00           H  
HETATM  117  H59 UNL     1      -6.860  -0.131  -1.471  1.00  0.00           H  
HETATM  118  H60 UNL     1      -9.076   1.690  -2.010  1.00  0.00           H  
HETATM  119  H61 UNL     1      -8.770   2.936   0.284  1.00  0.00           H  
HETATM  120  H62 UNL     1      -8.066   1.409   0.859  1.00  0.00           H  
HETATM  121  H63 UNL     1      -9.785   1.456   0.184  1.00  0.00           H  
HETATM  122  H64 UNL     1      -3.958   2.348  -2.137  1.00  0.00           H  
HETATM  123  H65 UNL     1      -4.823   0.920  -1.633  1.00  0.00           H  
HETATM  124  H66 UNL     1      -2.798   1.971  -0.392  1.00  0.00           H  
HETATM  125  H67 UNL     1      -3.859   5.169   2.444  1.00  0.00           H  
HETATM  126  H68 UNL     1      -3.751   6.200   0.925  1.00  0.00           H  
HETATM  127  H69 UNL     1      -2.302   5.814   1.861  1.00  0.00           H  
CONECT    1    2   59   60   61
CONECT    2    3
CONECT    3    4   54   62
CONECT    4    5   34   63
CONECT    5    6
CONECT    6    7   32   64
CONECT    7    8
CONECT    8    9   10   65
CONECT    9   66   67   68
CONECT   10   11   28   69
CONECT   11   12
CONECT   12   13   27   70
CONECT   13   14   71   72
CONECT   14   15   16   17
CONECT   15   73   74   75
CONECT   16   76
CONECT   17   18   25   77
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   78   79
CONECT   22   23   24   80
CONECT   23   81   82   83
CONECT   24   84   85   86
CONECT   25   26   27   87
CONECT   26   88   89   90
CONECT   28   29   32   91
CONECT   29   30   31
CONECT   30   92   93   94
CONECT   31   95   96   97
CONECT   32   33   98
CONECT   33   99
CONECT   34   35   38  100
CONECT   35   36  101  102
CONECT   36   37   37  103
CONECT   38   39  104  105
CONECT   39   40   41  106
CONECT   40  107  108  109
CONECT   41   42   43  110
CONECT   42  111
CONECT   43   44   44  112
CONECT   44   45  113
CONECT   45   46   46  114
CONECT   46   47  115
CONECT   47   48  116  117
CONECT   48   49   50  118
CONECT   49  119  120  121
CONECT   50   51
CONECT   51   52   52   53
CONECT   53   54  122  123
CONECT   54   55  124
CONECT   55   56
CONECT   56   57   58   58
CONECT   57  125  126  127
END

HMDB0015418
     RDKit          3D
Josamycin
127129  0  0  0  0  0  0  0  0999 V2000
   -5.3214    0.7796    2.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1009    0.9945    2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    0.7467    0.8006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.3803    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9497   -0.4001    1.3524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814   -0.0160    0.7541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0887   -1.1505    0.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -0.6979   -0.3361 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7843   -1.8306   -0.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918    0.2605    0.4176 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0536    0.6035   -0.3688 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2839    0.1059    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9400   -0.7608   -0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4354   -0.4696   -1.0134 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1457   -1.5837   -1.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051    0.7232   -1.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9962   -0.3950    0.4001 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3345    0.0369    0.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3949   -0.7498    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1274   -1.9059    1.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957   -0.3475    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4188   -0.8024   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8837   -0.4027   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7223   -0.0854   -1.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2099    0.6220    1.2006 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6907   -0.0636    2.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1579    1.1479    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    1.4485    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8937    2.4146    1.5067 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    2.0319    2.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    3.3096    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292    0.9515    1.6215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8249    1.9587    2.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6512   -1.7339    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6110   -2.5259    1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2176   -2.6973    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996   -3.5750    1.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -1.8525   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264   -3.2995   -0.4596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2886   -3.7478    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867   -3.3078   -1.6533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7003   -3.1567   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9215   -2.4680   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6253   -1.6428   -3.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0394   -1.3346   -3.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6674   -0.6150   -2.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9617    0.0360   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2101    1.5261   -1.2817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7507    1.8426    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0860    2.1958   -1.6618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9215    2.6858   -1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7960    3.8750   -0.8700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399    1.9568   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8506    1.9672   -0.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9766    3.1846    0.6441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394    4.1609    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2828    5.3875    1.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9712    3.9480    0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1920    0.9664    3.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0657    1.4094    0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7508    6.1996    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    5.8145    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Antibiotic yl-704 a3	ChEBI
EN-141	ChEBI
JM	ChEBI
Josamicina	ChEBI
Josamycine	ChEBI
Josamycinum	ChEBI
Kitasamycin a3	ChEBI
Leucomycin a3	ChEBI
Leucomycin V 3-acetate 4b-(3-methylbutanoate)	ChEBI
Leucomycin V 3-acetate 4(b)-(3-methylbutanoate)	ChEBI
Leucomycin V 3-acetate 4(beta)-(3-methylbutanoate)	ChEBI
Turimycin a5	ChEBI
yl-704 a3	ChEBI
Leucomycin V 3-acetic acid 4b-(3-methylbutanoic acid)	Generator
Leucomycin V 3-acetic acid 4(b)-(3-methylbutanoic acid)	Generator
Leucomycin V 3-acetate 4(β)-(3-methylbutanoate)	Generator
Leucomycin V 3-acetic acid 4(beta)-(3-methylbutanoic acid)	Generator
Leucomycin V 3-acetic acid 4(β)-(3-methylbutanoic acid)	Generator
Leucomycin V, 3-acetate 4b-(3-methylbutanoate)	HMDB
Wilprafen	HMDB

Chemical Formula

C₄₂H₆₉NO₁₅

Average Molecular Weight

827.995

Monoisotopic Molecular Weight

827.466720543

IUPAC Name

(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

Traditional Name

josamycin

CAS Registry Number

16846-24-5

SMILES

CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O

InChI Identifier

InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1

InChI Key

XJSFLOJWULLJQS-NGVXBBESSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Oxane
Alpha-hydrogen aldehyde
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Aldehyde
Organonitrogen compound
Organic nitrogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:31739 )
tertiary amino compound (CHEBI:31739 )
macrolide antibiotic (CHEBI:31739 )
acetate ester (CHEBI:31739 )
disaccharide derivative (CHEBI:31739 )
glycoside (CHEBI:31739 )
aldehyde (CHEBI:31739 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0015418)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Josamycin Action Pathway (PathBank: SMP0000731)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.054 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	3.47	ALOGPS
logP	3.22	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	7.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	206.05 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	211.03 m³·mol⁻¹	ChemAxon
Polarizability	87.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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+H]+	276.771	30932474
DeepCCS	[M-H]-	275.118	30932474
DeepCCS	[M-2H]-	309.153	30932474
DeepCCS	[M+Na]+	282.928	30932474
AllCCS	[M+H]+	283.8	32859911
AllCCS	[M+H-H2O]+	283.6	32859911
AllCCS	[M+NH4]+	284.0	32859911
AllCCS	[M+Na]+	284.0	32859911
AllCCS	[M-H]-	262.4	32859911
AllCCS	[M+Na-2H]-	269.0	32859911
AllCCS	[M+HCOO]-	276.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Josamycin	CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O	4307.2	Standard polar	33892256
Josamycin	CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O	4774.9	Standard non polar	33892256
Josamycin	CO[C@H]1[C@H](OC(=O)C)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@H](N(C)C)[C@H]1O	4830.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Josamycin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-19	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 - Josamycin 10V, Positive-QTOF	splash10-06vi-3002921760-f1a621e9c87868e86a70	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 20V, Positive-QTOF	splash10-0573-7022931100-55728374a750214dcfd2	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 40V, Positive-QTOF	splash10-002f-9112300000-6fad22ed83270743a807	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 10V, Negative-QTOF	splash10-0a7i-7427620970-15829300f9319bfce32a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 20V, Negative-QTOF	splash10-0a6r-3312930210-7346fec1317f39fec6da	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 40V, Negative-QTOF	splash10-004i-6302901100-988bf63a81925c47fc8d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 10V, Positive-QTOF	splash10-01u0-0000000950-d1915db52ffd3fe32823	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 20V, Positive-QTOF	splash10-002f-1001000920-ab7b990bff987b9f9006	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 40V, Positive-QTOF	splash10-05mo-8906110300-66f764c251505c96cd85	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 10V, Negative-QTOF	splash10-05r0-2000011960-b7b5d06cbb899d1f6853	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 20V, Negative-QTOF	splash10-0a59-9100011400-fd587738c70572c9acaa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Josamycin 40V, Negative-QTOF	splash10-052f-9103100120-a381a9435caad097f561	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Josamycin Action Pathway		Not Available

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 DB01321	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01321	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01321

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00018736

Chemspider ID

4445361

KEGG Compound ID

C12662

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Josamycin

METLIN ID

Not Available

PubChem Compound

5282165

PDB ID

Not Available

ChEBI ID

31739

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

Przybylski P, Pyta K, Stefanska J, Brzezinski B, Bartl F: Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin. Magn Reson Chem. 2010 Apr;48(4):286-96. doi: 10.1002/mrc.2574. [PubMed:20186698 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

Showing metabocard for Josamycin (HMDB0015418)

MOL for HMDB0015418 (Josamycin)

3D MOL for HMDB0015418 (Josamycin)

3D SDF for HMDB0015418 (Josamycin)

3D-SDF for HMDB0015418 (Josamycin)

PDB for HMDB0015418 (Josamycin)

3D PDB for HMDB0015418 (Josamycin)

SMILES for HMDB0015418 (Josamycin)

INCHI for HMDB0015418 (Josamycin)

Structure for HMDB0015418 (Josamycin)

3D Structure for HMDB0015418 (Josamycin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References