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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014699

Secondary Accession Numbers

HMDB14699

Metabolite Identification

Common Name

Bosentan

Description

Bosentan, also known as tracleer or bosentan hydrate, 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. Bosentan is a drug which is used in the treatment of pulmonary arterial hypertension (pah), to improve exercise ability and to decrease the rate of clinical worsening (in patients with who class iii or iv symptoms). Bosentan was studied in heart failure in a trial called REACH-1 that was terminated early in 1997 due to toxicity at the dose that was being studied; as of 2001 the results of that trial had not been published. Bosentan is an extremely weak basic (essentially neutral) compound (based on its pKa). The doctor must document a negative pregnancy test for women before prescribing the drug, counsel about contraception, and give regular pregnancy tests. Under normal conditions, endothelin-1 binding of ET-A receptors causes constriction of the pulmonary blood vessels. Peak plasma concentration of bosentan with the dispersable tablets for oral suspension is 14% less on average compared to peak concentration of the oral tablets.

Structure

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

559
  Mrv0541 02231214462D          

 39 42  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
    8.0804    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
    8.0804    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
    8.0804   -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
    8.0804   -2.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4207    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
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  7 33  1  0  0  0  0
  8 23  1  0  0  0  0
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  9 26  2  0  0  0  0
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 13 14  1  0  0  0  0
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 14 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
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 20 22  1  0  0  0  0
 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

HMDB0014699
     RDKit          3D
Bosentan
 68 71  0  0  0  0  0  0  0  0999 V2000
   -2.7425    4.7153    2.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    3.5490    2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6309    4.3983    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0951    2.1010   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    2.2551    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    1.2208    0.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.0130    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -0.3894   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.3157   -1.4679 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.7589   -0.9899 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.8054    2.7258   -2.1755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    2.5005    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    1.3246   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8044   -0.9467    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -2.1708    2.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -3.1671    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8235    4.5805    3.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492    5.6410    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929    4.6523    3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    5.3120    0.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5722    1.5903    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0200   -0.6559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8728   -0.0332    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -6.0131   -4.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973   -7.2698   -3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7827   -6.1487   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563   -0.2673    2.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4838   -1.3327    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258   -2.5485    3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.8868    3.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062   -3.8278    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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 37 64  1  0
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 38 66  1  0
 38 67  1  0
 39 68  1  0
M  END

559
  Mrv0541 02231214462D          

 39 42  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
    8.0804    2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6500    1.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  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
 10 26  1  0  0  0  0
 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
> <DATABASE_ID>
HMDB0014699

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)

> <INCHI_KEY>
GJPICJJJRGTNOD-UHFFFAOYSA-N

> <FORMULA>
C27H29N5O6S

> <MOLECULAR_WEIGHT>
551.614

> <EXACT_MASS>
551.183854375

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
57.885321642011014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
4.941747168000001

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.098839159321948

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.795967211163311

> <JCHEM_PKA_STRONGEST_BASIC>
-0.42784343298886884

> <JCHEM_POLAR_SURFACE_AREA>
145.65000000000003

> <JCHEM_REFRACTIVITY>
166.65719999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bosentan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014699
     RDKit          3D
Bosentan
 68 71  0  0  0  0  0  0  0  0999 V2000
   -2.7425    4.7153    2.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    3.5490    2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    3.3740    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309    4.3983    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    4.2619   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    3.1411   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    2.1010   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    2.2551    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    1.2208    0.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.0130    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -0.3894   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.3157   -1.4679 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.7589   -0.9899 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.8054    2.7258   -2.1755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    2.5005    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    1.3246   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    1.8496   -1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    1.4369   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0799    0.5025   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4588    0.0505    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    1.1621    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4266   -1.0845    1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1268   -0.3676   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977   -0.0146    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    0.3945    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -1.6578   -1.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298   -2.4555   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4955   -3.7879   -1.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134   -4.3425   -2.7243 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495   -5.5654   -3.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -6.2804   -2.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338   -5.6846   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -4.4908   -1.2421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -2.0215   -0.1642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -0.8675    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7231   -0.3445    1.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044   -0.9467    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -2.1708    2.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -3.1671    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8235    4.5805    3.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492    5.6410    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929    4.6523    3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    5.3120    0.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    5.0764   -1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055    2.9893   -2.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682    1.1987   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118   -0.1398   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249    2.5659   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6507    1.8558   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    1.5903    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1364    0.7164    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    1.9920    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200   -0.6559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995   -1.9747    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5077   -1.3184    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2179   -0.4962   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6374   -1.3171   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9838    0.4258   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.7524    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.0332    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -6.0131   -4.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973   -7.2698   -3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7827   -6.1487   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563   -0.2673    2.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4838   -1.3327    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258   -2.5485    3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.8868    3.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062   -3.8278    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 19 24  1  0
 24 25  2  0
 11 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 27 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
  8  3  1  0
 35 10  2  0
 25 16  1  0
 33 28  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  0
  6 45  1  0
  7 46  1  0
 12 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 25 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 37 64  1  0
 37 65  1  0
 38 66  1  0
 38 67  1  0
 39 68  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 559                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         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
HETATM   39  C   UNK     0       3.080   2.652   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   39                                                       
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                                                       
CONECT   39    6                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0014699
HETATM    1  C1  UNL     1      -2.742   4.715   2.856  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.426   3.549   2.104  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.882   3.374   0.790  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.631   4.398   0.219  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.108   4.262  -1.070  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.854   3.141  -1.793  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.095   2.101  -1.229  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.631   2.255   0.057  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.863   1.221   0.674  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.883  -0.013   0.001  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.042  -0.389  -0.956  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.033   0.316  -1.468  1.00  0.00           N  
HETATM   13  S1  UNL     1       0.748   1.759  -0.990  1.00  0.00           S  
HETATM   14  O3  UNL     1       0.805   2.726  -2.175  1.00  0.00           O  
HETATM   15  O4  UNL     1       0.201   2.500   0.142  1.00  0.00           O  
HETATM   16  C10 UNL     1       2.456   1.325  -0.599  1.00  0.00           C  
HETATM   17  C11 UNL     1       3.513   1.850  -1.284  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.817   1.437  -0.983  1.00  0.00           C  
HETATM   19  C13 UNL     1       5.080   0.502  -0.004  1.00  0.00           C  
HETATM   20  C14 UNL     1       6.459   0.050   0.305  1.00  0.00           C  
HETATM   21  C15 UNL     1       7.263   1.162   0.979  1.00  0.00           C  
HETATM   22  C16 UNL     1       6.427  -1.084   1.316  1.00  0.00           C  
HETATM   23  C17 UNL     1       7.127  -0.368  -0.975  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.998  -0.015   0.676  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.687   0.395   0.382  1.00  0.00           C  
HETATM   26  N2  UNL     1      -1.258  -1.658  -1.520  1.00  0.00           N  
HETATM   27  C20 UNL     1      -2.230  -2.456  -1.142  1.00  0.00           C  
HETATM   28  C21 UNL     1      -2.496  -3.788  -1.746  1.00  0.00           C  
HETATM   29  N3  UNL     1      -1.813  -4.343  -2.724  1.00  0.00           N  
HETATM   30  C22 UNL     1      -2.150  -5.565  -3.201  1.00  0.00           C  
HETATM   31  C23 UNL     1      -3.233  -6.280  -2.668  1.00  0.00           C  
HETATM   32  C24 UNL     1      -3.934  -5.685  -1.647  1.00  0.00           C  
HETATM   33  N4  UNL     1      -3.541  -4.491  -1.242  1.00  0.00           N  
HETATM   34  N5  UNL     1      -3.043  -2.021  -0.164  1.00  0.00           N  
HETATM   35  C25 UNL     1      -2.956  -0.867   0.446  1.00  0.00           C  
HETATM   36  O5  UNL     1      -3.723  -0.344   1.435  1.00  0.00           O  
HETATM   37  C26 UNL     1      -4.804  -0.947   2.068  1.00  0.00           C  
HETATM   38  C27 UNL     1      -4.379  -2.171   2.829  1.00  0.00           C  
HETATM   39  O6  UNL     1      -3.808  -3.167   2.062  1.00  0.00           O  
HETATM   40  H1  UNL     1      -3.823   4.581   3.139  1.00  0.00           H  
HETATM   41  H2  UNL     1      -2.549   5.641   2.331  1.00  0.00           H  
HETATM   42  H3  UNL     1      -2.193   4.652   3.813  1.00  0.00           H  
HETATM   43  H4  UNL     1      -3.854   5.312   0.741  1.00  0.00           H  
HETATM   44  H5  UNL     1      -4.707   5.076  -1.522  1.00  0.00           H  
HETATM   45  H6  UNL     1      -4.205   2.989  -2.797  1.00  0.00           H  
HETATM   46  H7  UNL     1      -2.868   1.199  -1.765  1.00  0.00           H  
HETATM   47  H8  UNL     1       0.512  -0.140  -2.349  1.00  0.00           H  
HETATM   48  H9  UNL     1       3.325   2.566  -2.045  1.00  0.00           H  
HETATM   49  H10 UNL     1       5.651   1.856  -1.517  1.00  0.00           H  
HETATM   50  H11 UNL     1       6.572   1.590   1.774  1.00  0.00           H  
HETATM   51  H12 UNL     1       8.136   0.716   1.473  1.00  0.00           H  
HETATM   52  H13 UNL     1       7.496   1.992   0.306  1.00  0.00           H  
HETATM   53  H14 UNL     1       6.020  -0.656   2.258  1.00  0.00           H  
HETATM   54  H15 UNL     1       5.899  -1.975   0.936  1.00  0.00           H  
HETATM   55  H16 UNL     1       7.508  -1.318   1.544  1.00  0.00           H  
HETATM   56  H17 UNL     1       8.218  -0.496  -0.793  1.00  0.00           H  
HETATM   57  H18 UNL     1       6.637  -1.317  -1.283  1.00  0.00           H  
HETATM   58  H19 UNL     1       6.984   0.426  -1.722  1.00  0.00           H  
HETATM   59  H20 UNL     1       4.189  -0.752   1.453  1.00  0.00           H  
HETATM   60  H21 UNL     1       1.873  -0.033   0.926  1.00  0.00           H  
HETATM   61  H22 UNL     1      -1.585  -6.013  -4.002  1.00  0.00           H  
HETATM   62  H23 UNL     1      -3.497  -7.270  -3.059  1.00  0.00           H  
HETATM   63  H24 UNL     1      -4.783  -6.149  -1.171  1.00  0.00           H  
HETATM   64  H25 UNL     1      -5.456  -0.267   2.655  1.00  0.00           H  
HETATM   65  H26 UNL     1      -5.484  -1.333   1.232  1.00  0.00           H  
HETATM   66  H27 UNL     1      -5.226  -2.548   3.449  1.00  0.00           H  
HETATM   67  H28 UNL     1      -3.571  -1.887   3.591  1.00  0.00           H  
HETATM   68  H29 UNL     1      -3.306  -3.828   2.644  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   43
CONECT    5    6    6   44
CONECT    6    7   45
CONECT    7    8    8   46
CONECT    8    9
CONECT    9   10
CONECT   10   11   35   35
CONECT   11   12   26   26
CONECT   12   13   47
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   17   17   25
CONECT   17   18   48
CONECT   18   19   19   49
CONECT   19   20   24
CONECT   20   21   22   23
CONECT   21   50   51   52
CONECT   22   53   54   55
CONECT   23   56   57   58
CONECT   24   25   25   59
CONECT   25   60
CONECT   26   27
CONECT   27   28   34   34
CONECT   28   29   29   33
CONECT   29   30
CONECT   30   31   31   61
CONECT   31   32   62
CONECT   32   33   33   63
CONECT   34   35
CONECT   35   36
CONECT   36   37
CONECT   37   38   64   65
CONECT   38   39   66   67
CONECT   39   68
END

HMDB0014699
     RDKit          3D
Bosentan
 68 71  0  0  0  0  0  0  0  0999 V2000
   -2.7425    4.7153    2.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    3.5490    2.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    3.3740    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309    4.3983    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    4.2619   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    3.1411   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    2.1010   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313    2.2551    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    1.2208    0.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.0130    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -0.3894   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.3157   -1.4679 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.7589   -0.9899 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.8054    2.7258   -2.1755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    2.5005    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    1.3246   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    1.8496   -1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    1.4369   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0799    0.5025   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4588    0.0505    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    1.1621    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4266   -1.0845    1.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1268   -0.3676   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977   -0.0146    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    0.3945    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -1.6578   -1.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298   -2.4555   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4955   -3.7879   -1.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134   -4.3425   -2.7243 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495   -5.5654   -3.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -6.2804   -2.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338   -5.6846   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -4.4908   -1.2421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -2.0215   -0.1642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -0.8675    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7231   -0.3445    1.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044   -0.9467    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -2.1708    2.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -3.1671    2.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8235    4.5805    3.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492    5.6410    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929    4.6523    3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    5.3120    0.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    5.0764   -1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055    2.9893   -2.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682    1.1987   -1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118   -0.1398   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249    2.5659   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6507    1.8558   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    1.5903    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1364    0.7164    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    1.9920    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200   -0.6559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995   -1.9747    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5077   -1.3184    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2179   -0.4962   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6374   -1.3171   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9838    0.4258   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.7524    1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.0332    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -6.0131   -4.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973   -7.2698   -3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7827   -6.1487   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563   -0.2673    2.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4838   -1.3327    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258   -2.5485    3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.8868    3.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062   -3.8278    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 19 24  1  0
 24 25  2  0
 11 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 27 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
  8  3  1  0
 35 10  2  0
 25 16  1  0
 33 28  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  0
  6 45  1  0
  7 46  1  0
 12 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 25 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 37 64  1  0
 37 65  1  0
 38 66  1  0
 38 67  1  0
 39 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulfornamide	ChEBI
Bosentanum	ChEBI
p-Tert-butyl-N-(6-(2-hydroxyethoxy)-5-(O-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide	ChEBI
4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulphornamide	Generator
p-Tert-butyl-N-(6-(2-hydroxyethoxy)-5-(O-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulphonamide	Generator
Bosentan hydrate	HMDB
4-t-Butyl-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide	HMDB
Bosentan monohydrate	HMDB
Bosentan anhydrous	HMDB
Tracleer	HMDB

Chemical Formula

C₂₇H₂₉N₅O₆S

Average Molecular Weight

551.614

Monoisotopic Molecular Weight

551.183854375

IUPAC Name

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

Traditional Name

bosentan

CAS Registry Number

147536-97-8

SMILES

COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1

InChI Identifier

InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)

InChI Key

GJPICJJJRGTNOD-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
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Imidolactam
Benzenoid
Organosulfonic acid amide
Heteroaromatic compound
Aminosulfonyl compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Azacycle
Ether
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Primary alcohol
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:51450 )
pyrimidines (CHEBI:51450 )
primary alcohol (CHEBI:51450 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014699)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.009 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	4.18	ALOGPS
logP	4.94	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.8	ChemAxon
pKa (Strongest Basic)	-0.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.65 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	166.66 m³·mol⁻¹	ChemAxon
Polarizability	57.89 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
DarkChem	[M+H]+	227.047	31661259
DarkChem	[M-H]-	223.703	31661259
DeepCCS	[M+H]+	214.292	30932474
DeepCCS	[M-H]-	211.896	30932474
DeepCCS	[M-2H]-	244.779	30932474
DeepCCS	[M+Na]+	220.204	30932474
AllCCS	[M+H]+	227.3	32859911
AllCCS	[M+H-H2O]+	225.7	32859911
AllCCS	[M+NH4]+	228.8	32859911
AllCCS	[M+Na]+	229.3	32859911
AllCCS	[M-H]-	221.8	32859911
AllCCS	[M+Na-2H]-	222.7	32859911
AllCCS	[M+HCOO]-	223.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bosentan	COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1	5587.3	Standard polar	33892256
Bosentan	COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1	4249.8	Standard non polar	33892256
Bosentan	COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1	4314.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bosentan,1TMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C)N=C(C2=NC=CC=N2)N=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4289.5	Semi standard non polar	33892256
Bosentan,1TMS,isomer #2	COC1=CC=CC=C1OC1=C(OCCO)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4149.8	Semi standard non polar	33892256
Bosentan,2TMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4165.7	Semi standard non polar	33892256
Bosentan,2TMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4135.6	Standard non polar	33892256
Bosentan,2TMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	5766.8	Standard polar	33892256
Bosentan,1TBDMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C(C)(C)C)N=C(C2=NC=CC=N2)N=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4473.1	Semi standard non polar	33892256
Bosentan,1TBDMS,isomer #2	COC1=CC=CC=C1OC1=C(OCCO)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4349.4	Semi standard non polar	33892256
Bosentan,2TBDMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C(C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4508.3	Semi standard non polar	33892256
Bosentan,2TBDMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C(C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	4552.1	Standard non polar	33892256
Bosentan,2TBDMS,isomer #1	COC1=CC=CC=C1OC1=C(OCCO[Si](C)(C)C(C)(C)C)N=C(C2=NC=CC=N2)N=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1	5746.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9f-1404490000-6d317563fca85570bb94	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-8400329000-23bc8d319fee004b04e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS ("Bosentan,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bosentan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan LC-ESI-QFT , negative-QTOF	splash10-0udj-0810090000-b97444dff91ec725276d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan LC-ESI-QFT , positive-QTOF	splash10-0udi-1690040000-c561d9dbb5ed88285519	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 50V, Positive-QTOF	splash10-0udi-0290000000-917fcf22a5648855f494	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 20V, Positive-QTOF	splash10-0udi-0000090000-804fbcd24b248dea41cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 10V, Positive-QTOF	splash10-0udi-0000090000-37d3e81ca9fac1bb8607	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 30V, Positive-QTOF	splash10-0udi-0032090000-6b8d5527e6d09bf8bd93	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 40V, Positive-QTOF	splash10-0udi-0192000000-ac3f1b4e6b6da63962f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 35V, Positive-QTOF	splash10-0udi-1690040000-53b916bf54d069a5d9af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bosentan 35V, Negative-QTOF	splash10-0udj-0700090000-a1325fb53ae46b3119a0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 10V, Positive-QTOF	splash10-0udi-0020190000-45fdf2d2b678882a2c9a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 20V, Positive-QTOF	splash10-01r2-7853970000-73d404cdce8bec564973	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 40V, Positive-QTOF	splash10-0zmr-4911000000-355d0a86f2c020114251	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 10V, Negative-QTOF	splash10-0udi-1111090000-838b3a76b34448d48154	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 20V, Negative-QTOF	splash10-00b9-1938000000-4a504df1e7892ab5ed7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 40V, Negative-QTOF	splash10-03g3-8592000000-757b42467cf720e1d98b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 10V, Positive-QTOF	splash10-0udi-0000090000-0264cc47a8b7eb39ffb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 20V, Positive-QTOF	splash10-0pb9-0200190000-c06202aa662980be16e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 40V, Positive-QTOF	splash10-0ab9-6900720000-9771730325d97d3f1f0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 10V, Negative-QTOF	splash10-0udi-0000090000-12b263be07bc58a79d77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 20V, Negative-QTOF	splash10-0zfu-0101490000-41d3bf6ec3c473268216	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bosentan 40V, Negative-QTOF	splash10-0udj-0223930000-515898571490d1845bf8	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00559	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00559	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00559

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bosentan

METLIN ID

Not Available

PubChem Compound

104865

PDB ID

Not Available

ChEBI ID

51450

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

Not Available

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

Dingemanse J, Schaarschmidt D, van Giersbergen PL: Investigation of the mutual pharmacokinetic interactions between bosentan, a dual endothelin receptor antagonist, and simvastatin. Clin Pharmacokinet. 2003;42(3):293-301. [PubMed:12603176 ]
Dingemanse J, van Giersbergen PL: Clinical pharmacology of bosentan, a dual endothelin receptor antagonist. Clin Pharmacokinet. 2004;43(15):1089-115. [PubMed:15568889 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]

Enzyme Details

2. Cytochrome P450 2C9

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]

Enzyme Details

3. Endothelin-1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for endothelin-1. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. The rank order of binding affinities for ET-A is:ET1 > ET2 >> ET3
Gene Name:: EDNRA
Uniprot ID:: P25101
Molecular weight:: 48721.8

References

Albertini M, Lafortuna CL, Ciminaghi B, Mazzola S, Clement MG: Endothelin involvement in respiratory centre activity. Prostaglandins Leukot Essent Fatty Acids. 2001 Sep;65(3):157-63. [PubMed:11728166 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kiowski W, Sutsch G, Oechslin E, Bertel O: Hemodynamic effects of bosentan in patients with chronic heart failure. Heart Fail Rev. 2001 Dec;6(4):325-34. [PubMed:11447307 ]
Kramp R, Fourmanoir P, Caron N: Endothelin resets renal blood flow autoregulatory efficiency during acute blockade of NO in the rat. Am J Physiol Renal Physiol. 2001 Dec;281(6):F1132-40. [PubMed:11704565 ]
Martin C, Held HD, Uhlig S: Differential effects of the mixed ET(A)/ET(B)-receptor antagonist bosentan on endothelin-induced bronchoconstriction, vasoconstriction and prostacyclin release. Naunyn Schmiedebergs Arch Pharmacol. 2000 Aug;362(2):128-36. [PubMed:10961375 ]
Sihvola RK, Pulkkinen VP, Koskinen PK, Lemstrom KB: Crosstalk of endothelin-1 and platelet-derived growth factor in cardiac allograft arteriosclerosis. J Am Coll Cardiol. 2002 Feb 20;39(4):710-7. [PubMed:11849873 ]

Enzyme Details

4. Endothelin B receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Non-specific receptor for endothelin 1, 2, and 3. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: EDNRB
Uniprot ID:: P24530
Molecular weight:: 49643.3

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gardiner SM, Kemp PA, March JE, Bennett T: Effects of bosentan (Ro 47-0203), an ETA-, ETB-receptor antagonist, on regional haemodynamic responses to endothelins in conscious rats. Br J Pharmacol. 1994 Jul;112(3):823-30. [PubMed:7921608 ]
Gupta SK, Saxena A, Singh U, Arya DS: Bosentan, the mixed ETA-ETB endothelin receptor antagonist, attenuated oxidative stress after experimental myocardial ischemia and reperfusion. Mol Cell Biochem. 2005 Jul;275(1-2):67-74. [PubMed:16335785 ]
Marano G, Palazzesi S, Bernucci P, Grigioni M, Formigari R, Ballerini L: ET(A)/ET(B) receptor antagonist bosentan inhibits neointimal development in collared carotid arteries of rabbits. Life Sci. 1998;63(18):PL259-66. [PubMed:9806221 ]
Richard V, Kaeffer N, Hogie M, Tron C, Blanc T, Thuillez C: Role of endogenous endothelin in myocardial and coronary endothelial injury after ischaemia and reperfusion in rats: studies with bosentan, a mixed ETA-ETB antagonist. Br J Pharmacol. 1994 Nov;113(3):869-76. [PubMed:7858879 ]
Said SA, Ammar el SM, Suddek GM: Effect of bosentan (ETA/ETB receptor antagonist) on metabolic changes during stress and diabetes. Pharmacol Res. 2005 Feb;51(2):107-15. [PubMed:15629255 ]

Transporters

Enzyme Details

1. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Fattinger K, Funk C, Pantze M, Weber C, Reichen J, Stieger B, Meier PJ: The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions. Clin Pharmacol Ther. 2001 Apr;69(4):223-31. [PubMed:11309550 ]

Showing metabocard for Bosentan (HMDB0014699)

MOL for HMDB0014699 (Bosentan)

3D MOL for HMDB0014699 (Bosentan)

3D SDF for HMDB0014699 (Bosentan)

3D-SDF for HMDB0014699 (Bosentan)

PDB for HMDB0014699 (Bosentan)

3D PDB for HMDB0014699 (Bosentan)

SMILES for HMDB0014699 (Bosentan)

INCHI for HMDB0014699 (Bosentan)

Structure for HMDB0014699 (Bosentan)

3D Structure for HMDB0014699 (Bosentan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References