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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:15:14 UTC

Update Date

2021-09-26 23:02:50 UTC

HMDB ID

HMDB0251051

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Desmethyl Bosentan

Description

4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-[2,2'-bipyrimidine]-4-yl]benzene-1-sulfonamide belongs to the class of organic compounds known as bipyrimidines and oligopyrimidines. These are organic compounds containing two or more pyrimidine rings directly linked to each other. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Based on a literature review very few articles have been published on 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-[2,2'-bipyrimidine]-4-yl]benzene-1-sulfonamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Desmethyl bosentan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Desmethyl Bosentan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv0541 09051315352D          

 38 41  0  0  0  0            999 V2000
    5.9370    1.4207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495    0.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    2.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.2919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    3.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    3.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3824    3.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2075    2.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    1.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803   -2.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  8  1  0  0  0  0
  1 20  1  0  0  0  0
  4 24  1  0  0  0  0
  4 27  1  0  0  0  0
  5 25  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
  7 33  1  0  0  0  0
  8 23  1  0  0  0  0
  9 23  1  0  0  0  0
  9 26  2  0  0  0  0
 10 25  2  0  0  0  0
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 11 28  2  0  0  0  0
 11 36  1  0  0  0  0
 12 28  1  0  0  0  0
 12 37  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 30  1  0  0  0  0
 27 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 31 34  1  0  0  0  0
 32 35  1  0  0  0  0
 34 35  2  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END

HMDB0251051
     RDKit          3D
Desmethyl Bosentan
 65 68  0  0  0  0  0  0  0  0999 V2000
    6.7329    0.5511   -1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394   -0.3137   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5033   -1.5747   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886    0.4080    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351   -0.5694   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.5265    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3413    0.3569    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014   -0.8806    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -0.9354    1.6732 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5585   -2.2848    1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411   -0.9423    3.1715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    0.3918    1.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.6144    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    1.9587    0.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    2.3454    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    3.7642   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450    4.2546   -0.4318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106    5.5597   -0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    6.4416   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084    5.8864   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    4.6093   -0.1590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817    1.4437    0.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1342    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -0.8502    0.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2735    0.4590    1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6231    0.7066    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429   -0.2797    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -1.6439    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -2.5848    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -3.4543    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -4.4280    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -4.5494   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -3.6785   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5351   -2.6876   -1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -1.8154   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -1.9262    0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -1.7875   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    0.6403   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481    1.5105   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.0396   -2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5749   -1.3581   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0475   -2.2348   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5535   -2.1335    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -0.1749    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4757    0.3559    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9947    1.4290    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0641    1.5306    0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074    1.2256    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011    1.3428    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1908    5.9432   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    7.5012   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    6.5565   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -1.5100    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7890   -0.2835   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2577    0.0943    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970    1.4571    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2269    0.4333    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947   -3.3339    2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -5.0997    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -5.3132   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988   -3.7513   -2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -1.9014   -2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -2.9037    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463   -2.6308   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
  8 37  1  0
 37 38  2  0
 38  5  1  0
 28 13  1  0
 35 30  1  0
 21 16  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  4 47  1  0
  6 48  1  0
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 12 50  1  0
 18 51  1  0
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 25 54  1  0
 25 55  1  0
 26 56  1  0
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 27 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 36 63  1  0
 37 64  1  0
 38 65  1  0
M  END

  Mrv0541 09051315352D          

 38 41  0  0  0  0            999 V2000
    5.9370    1.4207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495    0.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    2.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.2919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    3.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094    3.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3824    3.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2075    2.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    1.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645    0.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803   -1.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803   -2.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  8  1  0  0  0  0
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  8 23  1  0  0  0  0
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 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 18 21  1  0  0  0  0
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 20 21  2  0  0  0  0
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 23 24  2  0  0  0  0
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 26 28  1  0  0  0  0
 27 30  1  0  0  0  0
 27 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 31 34  1  0  0  0  0
 32 35  1  0  0  0  0
 34 35  2  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251051

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(OC2=CC=CC=C2O)C(OCCO)=NC(=N1)C1=NC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C26H27N5O6S/c1-26(2,3)17-9-11-18(12-10-17)38(34,35)31-22-21(37-20-8-5-4-7-19(20)33)25(36-16-15-32)30-24(29-22)23-27-13-6-14-28-23/h4-14,32-33H,15-16H2,1-3H3,(H,29,30,31)

> <INCHI_KEY>
STTLKJGYAWXIPP-UHFFFAOYSA-N

> <FORMULA>
C26H27N5O6S

> <MOLECULAR_WEIGHT>
537.587

> <EXACT_MASS>
537.168204311

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
56.044445758518805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.858380743333334

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.375365443301606

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.7948433037929785

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4278056354445682

> <JCHEM_POLAR_SURFACE_AREA>
156.64999999999998

> <JCHEM_REFRACTIVITY>
162.17489999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzenesulfonamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251051
     RDKit          3D
Desmethyl Bosentan
 65 68  0  0  0  0  0  0  0  0999 V2000
    6.7329    0.5511   -1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394   -0.3137   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5033   -1.5747   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886    0.4080    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351   -0.5694   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.5265    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3413    0.3569    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014   -0.8806    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -0.9354    1.6732 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5585   -2.2848    1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411   -0.9423    3.1715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    0.3918    1.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.6144    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    1.9587    0.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    2.3454    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    3.7642   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450    4.2546   -0.4318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106    5.5597   -0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    6.4416   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084    5.8864   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    4.6093   -0.1590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817    1.4437    0.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1342    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -0.8502    0.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6745   -0.5776    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2735    0.4590    1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6231    0.7066    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429   -0.2797    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -1.6439    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -2.5848    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -3.4543    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -4.4280    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -4.5494   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -3.6785   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5351   -2.6876   -1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -1.8154   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -1.9262    0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -1.7875   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    0.6403   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481    1.5105   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.0396   -2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5749   -1.3581   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0475   -2.2348   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5535   -2.1335    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -0.1749    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4757    0.3559    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9947    1.4290    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0641    1.5306    0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074    1.2256    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011    1.3428    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1908    5.9432   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    7.5012   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    6.5565   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -1.5100    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7890   -0.2835   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2577    0.0943    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970    1.4571    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2269    0.4333    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947   -3.3339    2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -5.0997    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -5.3132   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988   -3.7513   -2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -1.9014   -2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -2.9037    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463   -2.6308   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
  8 37  1  0
 37 38  2  0
 38  5  1  0
 28 13  1  0
 35 30  1  0
 21 16  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  4 47  1  0
  6 48  1  0
  7 49  1  0
 12 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 36 63  1  0
 37 64  1  0
 38 65  1  0
M  END

HEADER    PROTEIN                                 05-SEP-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-13         0                                  
HETATM    1  S   UNK     0      11.082   2.652   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      11.852   1.318   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.312   3.986   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   0.342   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081  -2.738   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.414   1.882   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.748  -6.588   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       9.748   1.882   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      11.082  -0.428   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.748  -2.738   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      13.750  -1.968   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      12.416  -4.278   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      16.417   5.732   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083   4.962   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.751   6.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.647   7.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.187   4.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.083   3.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   5.732   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   3.422   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750   2.652   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416   4.962   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   0.342   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415  -0.428   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415  -1.968   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082  -1.968   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.748  -0.428   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.416  -2.738   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.081  -4.278   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414   0.342   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.748  -1.968   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.080  -0.428   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.748  -5.048   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.414  -2.738   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.080  -1.968   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.083  -2.738   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.750  -5.048   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.083  -4.278   0.000  0.00  0.00           C+0
CONECT    1    2    3    8   20                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   24   27                                                       
CONECT    5   25   29                                                       
CONECT    6   30                                                            
CONECT    7   33                                                            
CONECT    8    1   23                                                       
CONECT    9   23   26                                                       
CONECT   10   25   26                                                       
CONECT   11   28   36                                                       
CONECT   12   28   37                                                       
CONECT   13   14   15   16   17                                             
CONECT   14   13   18   19                                                  
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   14   21                                                       
CONECT   19   14   22                                                       
CONECT   20    1   21   22                                                  
CONECT   21   18   20                                                       
CONECT   22   19   20                                                       
CONECT   23    8    9   24                                                  
CONECT   24    4   23   25                                                  
CONECT   25    5   10   24                                                  
CONECT   26    9   10   28                                                  
CONECT   27    4   30   31                                                  
CONECT   28   11   12   26                                                  
CONECT   29    5   33                                                       
CONECT   30    6   27   32                                                  
CONECT   31   27   34                                                       
CONECT   32   30   35                                                       
CONECT   33    7   29                                                       
CONECT   34   31   35                                                       
CONECT   35   32   34                                                       
CONECT   36   11   38                                                       
CONECT   37   12   38                                                       
CONECT   38   36   37                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0251051
HETATM    1  C1  UNL     1       6.733   0.551  -1.823  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.739  -0.314  -0.587  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.503  -1.575  -0.849  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.389   0.408   0.610  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.335  -0.569  -0.165  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.630   0.526   0.338  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.341   0.357   0.810  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.701  -0.881   0.807  1.00  0.00           C  
HETATM    9  S1  UNL     1       1.175  -0.935   1.673  1.00  0.00           S  
HETATM   10  O1  UNL     1       0.559  -2.285   1.360  1.00  0.00           O  
HETATM   11  O2  UNL     1       1.541  -0.942   3.172  1.00  0.00           O  
HETATM   12  N1  UNL     1       0.250   0.392   1.249  1.00  0.00           N  
HETATM   13  C9  UNL     1      -1.039   0.614   0.745  1.00  0.00           C  
HETATM   14  N2  UNL     1      -1.369   1.959   0.445  1.00  0.00           N  
HETATM   15  C10 UNL     1      -2.604   2.345   0.163  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.866   3.764  -0.151  1.00  0.00           C  
HETATM   17  N3  UNL     1      -4.045   4.255  -0.432  1.00  0.00           N  
HETATM   18  C12 UNL     1      -4.211   5.560  -0.732  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.117   6.442  -0.750  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.908   5.886  -0.449  1.00  0.00           C  
HETATM   21  N4  UNL     1      -1.780   4.609  -0.159  1.00  0.00           N  
HETATM   22  N5  UNL     1      -3.582   1.444   0.151  1.00  0.00           N  
HETATM   23  C15 UNL     1      -3.343   0.134   0.424  1.00  0.00           C  
HETATM   24  O3  UNL     1      -4.313  -0.850   0.431  1.00  0.00           O  
HETATM   25  C16 UNL     1      -5.675  -0.578   0.137  1.00  0.00           C  
HETATM   26  C17 UNL     1      -6.273   0.459   1.056  1.00  0.00           C  
HETATM   27  O4  UNL     1      -7.623   0.707   0.737  1.00  0.00           O  
HETATM   28  C18 UNL     1      -2.043  -0.280   0.722  1.00  0.00           C  
HETATM   29  O5  UNL     1      -1.825  -1.644   0.990  1.00  0.00           O  
HETATM   30  C19 UNL     1      -2.544  -2.585   0.249  1.00  0.00           C  
HETATM   31  C20 UNL     1      -3.320  -3.454   1.019  1.00  0.00           C  
HETATM   32  C21 UNL     1      -4.082  -4.428   0.402  1.00  0.00           C  
HETATM   33  C22 UNL     1      -4.088  -4.549  -0.982  1.00  0.00           C  
HETATM   34  C23 UNL     1      -3.314  -3.679  -1.714  1.00  0.00           C  
HETATM   35  C24 UNL     1      -2.535  -2.688  -1.106  1.00  0.00           C  
HETATM   36  O6  UNL     1      -1.762  -1.815  -1.871  1.00  0.00           O  
HETATM   37  C25 UNL     1       3.400  -1.926   0.307  1.00  0.00           C  
HETATM   38  C26 UNL     1       4.710  -1.787  -0.180  1.00  0.00           C  
HETATM   39  H1  UNL     1       7.789   0.640  -2.184  1.00  0.00           H  
HETATM   40  H2  UNL     1       6.248   1.511  -1.681  1.00  0.00           H  
HETATM   41  H3  UNL     1       6.176  -0.040  -2.594  1.00  0.00           H  
HETATM   42  H4  UNL     1       8.575  -1.358  -1.125  1.00  0.00           H  
HETATM   43  H5  UNL     1       7.048  -2.235  -1.608  1.00  0.00           H  
HETATM   44  H6  UNL     1       7.554  -2.134   0.126  1.00  0.00           H  
HETATM   45  H7  UNL     1       7.046  -0.175   1.520  1.00  0.00           H  
HETATM   46  H8  UNL     1       8.476   0.356   0.579  1.00  0.00           H  
HETATM   47  H9  UNL     1       6.995   1.429   0.715  1.00  0.00           H  
HETATM   48  H10 UNL     1       5.064   1.531   0.354  1.00  0.00           H  
HETATM   49  H11 UNL     1       2.807   1.226   1.204  1.00  0.00           H  
HETATM   50  H12 UNL     1       0.801   1.343   1.418  1.00  0.00           H  
HETATM   51  H13 UNL     1      -5.191   5.943  -0.944  1.00  0.00           H  
HETATM   52  H14 UNL     1      -3.252   7.501  -0.979  1.00  0.00           H  
HETATM   53  H15 UNL     1      -1.027   6.557  -0.453  1.00  0.00           H  
HETATM   54  H16 UNL     1      -6.247  -1.510   0.258  1.00  0.00           H  
HETATM   55  H17 UNL     1      -5.789  -0.284  -0.912  1.00  0.00           H  
HETATM   56  H18 UNL     1      -6.258   0.094   2.100  1.00  0.00           H  
HETATM   57  H19 UNL     1      -5.797   1.457   0.958  1.00  0.00           H  
HETATM   58  H20 UNL     1      -8.227   0.433   1.481  1.00  0.00           H  
HETATM   59  H21 UNL     1      -3.295  -3.334   2.113  1.00  0.00           H  
HETATM   60  H22 UNL     1      -4.677  -5.100   1.015  1.00  0.00           H  
HETATM   61  H23 UNL     1      -4.689  -5.313  -1.472  1.00  0.00           H  
HETATM   62  H24 UNL     1      -3.299  -3.751  -2.797  1.00  0.00           H  
HETATM   63  H25 UNL     1      -1.741  -1.901  -2.872  1.00  0.00           H  
HETATM   64  H26 UNL     1       2.921  -2.904   0.301  1.00  0.00           H  
HETATM   65  H27 UNL     1       5.246  -2.631  -0.570  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    4    5
CONECT    3   42   43   44
CONECT    4   45   46   47
CONECT    5    6    6   38
CONECT    6    7   48
CONECT    7    8    8   49
CONECT    8    9   37
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   50
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16   22   22
CONECT   16   17   17   21
CONECT   17   18
CONECT   18   19   19   51
CONECT   19   20   52
CONECT   20   21   21   53
CONECT   22   23
CONECT   23   24   28   28
CONECT   24   25
CONECT   25   26   54   55
CONECT   26   27   56   57
CONECT   27   58
CONECT   28   29
CONECT   29   30
CONECT   30   31   31   35
CONECT   31   32   59
CONECT   32   33   33   60
CONECT   33   34   61
CONECT   34   35   35   62
CONECT   35   36
CONECT   36   63
CONECT   37   38   38   64
CONECT   38   65
END

HMDB0251051
     RDKit          3D
Desmethyl Bosentan
 65 68  0  0  0  0  0  0  0  0999 V2000
    6.7329    0.5511   -1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394   -0.3137   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5033   -1.5747   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886    0.4080    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351   -0.5694   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    0.5265    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3413    0.3569    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014   -0.8806    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -0.9354    1.6732 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5585   -2.2848    1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411   -0.9423    3.1715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    0.3918    1.2489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.6144    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    1.9587    0.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    2.3454    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    3.7642   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450    4.2546   -0.4318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106    5.5597   -0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    6.4416   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084    5.8864   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    4.6093   -0.1590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817    1.4437    0.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1342    0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -0.8502    0.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6745   -0.5776    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2735    0.4590    1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6231    0.7066    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429   -0.2797    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -1.6439    0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -2.5848    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -3.4543    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -4.4280    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878   -4.5494   -0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -3.6785   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5351   -2.6876   -1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -1.8154   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -1.9262    0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -1.7875   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    0.6403   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481    1.5105   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.0396   -2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5749   -1.3581   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0475   -2.2348   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5535   -2.1335    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -0.1749    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4757    0.3559    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9947    1.4290    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0641    1.5306    0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8074    1.2256    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011    1.3428    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1908    5.9432   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    7.5012   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267    6.5565   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2473   -1.5100    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7890   -0.2835   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2577    0.0943    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970    1.4571    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2269    0.4333    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2947   -3.3339    2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774   -5.0997    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -5.3132   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988   -3.7513   -2.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -1.9014   -2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -2.9037    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463   -2.6308   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
  8 37  1  0
 37 38  2  0
 38  5  1  0
 28 13  1  0
 35 30  1  0
 21 16  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  4 47  1  0
  6 48  1  0
  7 49  1  0
 12 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 36 63  1  0
 37 64  1  0
 38 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-[2,2'-bipyrimidine]-4-yl]benzene-1-sulphonamide	Generator

Chemical Formula

C₂₆H₂₇N₅O₆S

Average Molecular Weight

537.587

Monoisotopic Molecular Weight

537.168204311

IUPAC Name

4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide

Traditional Name

4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzenesulfonamide

CAS Registry Number

Not Available

SMILES

CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(OC2=CC=CC=C2O)C(OCCO)=NC(=N1)C1=NC=CC=N1

InChI Identifier

InChI=1S/C26H27N5O6S/c1-26(2,3)17-9-11-18(12-10-17)38(34,35)31-22-21(37-20-8-5-4-7-19(20)33)25(36-16-15-32)30-24(29-22)23-27-13-6-14-28-23/h4-14,32-33H,15-16H2,1-3H3,(H,29,30,31)

InChI Key

STTLKJGYAWXIPP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyrimidines and oligopyrimidines. These are organic compounds containing two or more pyrimidine rings directly linked to each other. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Bipyrimidines and oligopyrimidines

Alternative Parents

Substituents

Bipyrimidine
Diaryl ether
Benzenesulfonamide
Benzenesulfonyl group
Phenylpropane
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Imidolactam
Benzenoid
Organosulfonic acid amide
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Ether
Azacycle
Alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.85	ALOGPS
logP	4.86	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.79	ChemAxon
pKa (Strongest Basic)	-0.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.65 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	162.17 m³·mol⁻¹	ChemAxon
Polarizability	56.04 Å³	ChemAxon
Number of Rings	4	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+H]+	215.433	30932474
DeepCCS	[M-H]-	213.037	30932474
DeepCCS	[M-2H]-	245.921	30932474
DeepCCS	[M+Na]+	221.345	30932474
AllCCS	[M+H]+	223.7	32859911
AllCCS	[M+H-H2O]+	222.0	32859911
AllCCS	[M+NH4]+	225.2	32859911
AllCCS	[M+Na]+	225.7	32859911
AllCCS	[M-H]-	217.0	32859911
AllCCS	[M+Na-2H]-	217.8	32859911
AllCCS	[M+HCOO]-	218.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desmethyl Bosentan	CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(OC2=CC=CC=C2O)C(OCCO)=NC(=N1)C1=NC=CC=N1	5689.7	Standard polar	33892256
Desmethyl Bosentan	CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(OC2=CC=CC=C2O)C(OCCO)=NC(=N1)C1=NC=CC=N1	4217.1	Standard non polar	33892256
Desmethyl Bosentan	CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(OC2=CC=CC=C2O)C(OCCO)=NC(=N1)C1=NC=CC=N1	4312.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desmethyl Bosentan,3TMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	4155.6	Semi standard non polar	33892256
Desmethyl Bosentan,3TMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	4163.7	Standard non polar	33892256
Desmethyl Bosentan,3TMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	5487.1	Standard polar	33892256
Desmethyl Bosentan,3TBDMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C(C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4639.6	Semi standard non polar	33892256
Desmethyl Bosentan,3TBDMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C(C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4814.5	Standard non polar	33892256
Desmethyl Bosentan,3TBDMS,isomer #1	CC(C)(C)C1=CC=C(S(=O)(=O)N(C2=NC(C3=NC=CC=N3)=NC(OCCO[Si](C)(C)C(C)(C)C)=C2OC2=CC=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	5534.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desmethyl Bosentan GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	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 - Desmethyl Bosentan 10V, Negative-QTOF	splash10-000i-0000490000-089fadd66f9d01b8f2b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethyl Bosentan 20V, Negative-QTOF	splash10-0553-0221790000-51d9a13a8d6f4ca4508a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethyl Bosentan 40V, Negative-QTOF	splash10-0gxa-0546900000-a9c3127824d9a78e6bf6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethyl Bosentan 10V, Positive-QTOF	splash10-000i-0000090000-8243beaf488f53649ea5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethyl Bosentan 20V, Positive-QTOF	splash10-000f-1320950000-7d92f1bce192be086da7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desmethyl Bosentan 40V, Positive-QTOF	splash10-0292-7906720000-0d4c484de2d5ef0add1c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

4932190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Desmethyl Bosentan (HMDB0251051)

MOL for HMDB0251051 (Desmethyl Bosentan)

3D MOL for HMDB0251051 (Desmethyl Bosentan)

3D SDF for HMDB0251051 (Desmethyl Bosentan)

3D-SDF for HMDB0251051 (Desmethyl Bosentan)

PDB for HMDB0251051 (Desmethyl Bosentan)

3D PDB for HMDB0251051 (Desmethyl Bosentan)

SMILES for HMDB0251051 (Desmethyl Bosentan)

INCHI for HMDB0251051 (Desmethyl Bosentan)

Structure for HMDB0251051 (Desmethyl Bosentan)

3D Structure for HMDB0251051 (Desmethyl Bosentan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra