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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015629

Secondary Accession Numbers

HMDB15629

Metabolite Identification

Common Name

Sitaxentan

Description

Sitaxentan, also known as TBC-11251, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Sitaxentan is an extremely weak basic (essentially neutral) compound (based on its pKa). Sitaxentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects. Sitaxentan is only found in individuals that have used or taken this drug. Under normal conditions, endothelin-1 binding of ET-A or ET-B receptors causes pulmonary vasoconstriction. By blocking this interaction, Sitaxentan decreases pulmonary vascular resistance. Sitaxentan is a competitive antagonist of endothelin-1 at the endothelin-A (ET-A) and endothelin-B (ET-B) receptors. Sitaxentan belongs to a class of drugs known as endothelin receptor antagonists (ERAs).

Structure

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

216235
  Mrv0541 02241213002D          

 29 32  0  0  0  0            999 V2000
    3.4449   -2.3243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1711    0.1898    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    2.1528    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7349   -0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7349   -1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253    1.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641    0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9781    0.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -0.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801   -0.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253   -1.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426    0.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963    1.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2398    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -1.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2398   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2164   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031    2.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  2  0  0  0  0
  2 10  1  0  0  0  0
  2 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 25  1  0  0  0  0
  4 19  1  0  0  0  0
  4 24  1  0  0  0  0
  5 20  1  0  0  0  0
  5 24  1  0  0  0  0
  6 18  2  0  0  0  0
  9 11  1  0  0  0  0
  9 26  1  0  0  0  0
 10 26  1  0  0  0  0
 11 28  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
 15 16  2  0  0  0  0
 15 23  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 23 25  2  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0015629
     RDKit          3D
Sitaxentan
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2292   -1.3624   -1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -0.2474   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.1823   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9060    1.2169    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    1.8101    0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    1.3714    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.3417   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -0.1707   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -1.4310    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.8249    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -2.3063    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -3.7519    1.0335 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -4.3091    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -3.3731   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -2.3408   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.1010   -1.9607 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0295   -1.2201   -3.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -1.3637   -2.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.4745   -1.2901 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.8039   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990    0.6777    0.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594    1.0471    1.6166 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219    1.4538    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2924    1.9603    1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.2962   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.6401   -2.0651 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3350    2.7966    1.7874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6889    3.0292    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8298    0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -1.1249   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.6541   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7195   -2.2563   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5206   -0.2877   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    1.8366    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -0.1141   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.6379   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -5.2087    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -3.5018   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.1864   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133    3.0056    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5352    1.9271    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0575    1.3910    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933    3.8857    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3120    3.1482    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
  7  2  1  0
 15 11  2  0
 25 20  2  0
 29  4  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 28 43  1  0
 28 44  1  0
M  END

216235
  Mrv0541 02241213002D          

 29 32  0  0  0  0            999 V2000
    3.4449   -2.3243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1711    0.1898    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    2.1528    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7349   -0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7349   -1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253    1.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641    0.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9781    0.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -0.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801   -0.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5253   -1.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426    0.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963    1.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2398    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -1.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2398   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2164   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031    2.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600   -1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  2  0  0  0  0
  2 10  1  0  0  0  0
  2 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 25  1  0  0  0  0
  4 19  1  0  0  0  0
  4 24  1  0  0  0  0
  5 20  1  0  0  0  0
  5 24  1  0  0  0  0
  6 18  2  0  0  0  0
  9 11  1  0  0  0  0
  9 26  1  0  0  0  0
 10 26  1  0  0  0  0
 11 28  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
 15 16  2  0  0  0  0
 15 23  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 23 25  2  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015629

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C18H15ClN2O6S2/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18/h3-5,7,21H,6,8H2,1-2H3

> <INCHI_KEY>
PHWXUGHIIBDVKD-UHFFFAOYSA-N

> <FORMULA>
C18H15ClN2O6S2

> <MOLECULAR_WEIGHT>
454.905

> <EXACT_MASS>
454.006005309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
43.11652205319554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
3.091685922

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.420143849604173

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.8883305321764725

> <JCHEM_PKA_STRONGEST_BASIC>
0.7450561162550599

> <JCHEM_POLAR_SURFACE_AREA>
107.73

> <JCHEM_REFRACTIVITY>
105.80450000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thelin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015629
     RDKit          3D
Sitaxentan
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2292   -1.3624   -1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -0.2474   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.1823   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9060    1.2169    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    1.8101    0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    1.3714    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.3417   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -0.1707   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -1.4310    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.8249    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -2.3063    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -3.7519    1.0335 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -4.3091    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -3.3731   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -2.3408   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.1010   -1.9607 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0295   -1.2201   -3.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -1.3637   -2.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.4745   -1.2901 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.8039   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990    0.6777    0.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594    1.0471    1.6166 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219    1.4538    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2924    1.9603    1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.2962   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.6401   -2.0651 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3350    2.7966    1.7874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6889    3.0292    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8298    0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -1.1249   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.6541   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7195   -2.2563   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5206   -0.2877   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    1.8366    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -0.1141   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.6379   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -5.2087    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -3.5018   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.1864   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133    3.0056    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5352    1.9271    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0575    1.3910    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933    3.8857    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3120    3.1482    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
  7  2  1  0
 15 11  2  0
 25 20  2  0
 29  4  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 28 43  1  0
 28 44  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 216235                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       6.430  -4.339   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       7.786   0.354   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0       9.352   4.019   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0      16.305  -0.124   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.305  -2.603   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.181   2.487   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.280   0.674   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.292   0.034   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.755  -0.723   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       7.466  -1.152   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       3.510  -1.628   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.181  -0.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.847   0.177   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.181  -2.133   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.106   1.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.513   2.487   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.514   0.177   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.847   1.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.848  -0.593   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.848  -2.133   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.514  -2.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.847  -2.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.076   3.005   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.204  -1.363   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.846   4.339   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.001  -1.628   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.525  -3.093   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.985  -3.093   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080  -4.339   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2    7    8   10   15                                             
CONECT    3   16   25                                                       
CONECT    4   19   24                                                       
CONECT    5   20   24                                                       
CONECT    6   18                                                            
CONECT    7    2                                                            
CONECT    8    2                                                            
CONECT    9   11   26                                                       
CONECT   10    2   26                                                       
CONECT   11    9   28                                                       
CONECT   12   13   14   17                                                  
CONECT   13   12   18                                                       
CONECT   14   12   21   22                                                  
CONECT   15    2   16   23                                                  
CONECT   16    3   15   18                                                  
CONECT   17   12   19                                                       
CONECT   18    6   13   16                                                  
CONECT   19    4   17   20                                                  
CONECT   20    5   19   21                                                  
CONECT   21   14   20                                                       
CONECT   22   14                                                            
CONECT   23   15   25                                                       
CONECT   24    4    5                                                       
CONECT   25    3   23                                                       
CONECT   26    9   10   27                                                  
CONECT   27    1   26   28                                                  
CONECT   28   11   27   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0015629
HETATM    1  C1  UNL     1      -3.229  -1.362  -1.724  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.374  -0.247  -0.770  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.676   0.182  -0.508  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.906   1.217   0.370  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.825   1.810   0.975  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.533   1.371   0.704  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.293   0.342  -0.168  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.920  -0.171  -0.497  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.634  -1.431   0.170  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.556  -1.825   0.987  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.516  -2.306   0.062  1.00  0.00           C  
HETATM   12  S1  UNL     1       0.720  -3.752   1.034  1.00  0.00           S  
HETATM   13  C11 UNL     1       2.189  -4.309   0.423  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.496  -3.373  -0.519  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.639  -2.341  -0.709  1.00  0.00           C  
HETATM   16  S2  UNL     1       1.962  -1.101  -1.961  1.00  0.00           S  
HETATM   17  O2  UNL     1       1.029  -1.220  -3.105  1.00  0.00           O  
HETATM   18  O3  UNL     1       3.346  -1.364  -2.574  1.00  0.00           O  
HETATM   19  N1  UNL     1       2.070   0.474  -1.290  1.00  0.00           N  
HETATM   20  C14 UNL     1       3.064   0.804  -0.331  1.00  0.00           C  
HETATM   21  O4  UNL     1       2.899   0.678   0.962  1.00  0.00           O  
HETATM   22  N2  UNL     1       3.959   1.047   1.617  1.00  0.00           N  
HETATM   23  C15 UNL     1       4.922   1.454   0.761  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.292   1.960   1.023  1.00  0.00           C  
HETATM   25  C17 UNL     1       4.344   1.296  -0.487  1.00  0.00           C  
HETATM   26 CL1  UNL     1       5.047   1.640  -2.065  1.00  0.00          CL  
HETATM   27  O5  UNL     1      -4.335   2.797   1.787  1.00  0.00           O  
HETATM   28  C18 UNL     1      -5.689   3.029   1.435  1.00  0.00           C  
HETATM   29  O6  UNL     1      -6.090   1.830   0.802  1.00  0.00           O  
HETATM   30  H1  UNL     1      -3.735  -1.125  -2.695  1.00  0.00           H  
HETATM   31  H2  UNL     1      -2.200  -1.654  -1.929  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.720  -2.256  -1.242  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.521  -0.288  -0.986  1.00  0.00           H  
HETATM   34  H5  UNL     1      -1.658   1.837   1.181  1.00  0.00           H  
HETATM   35  H6  UNL     1      -0.759  -0.114  -1.568  1.00  0.00           H  
HETATM   36  H7  UNL     1      -0.258   0.638  -0.026  1.00  0.00           H  
HETATM   37  H8  UNL     1       2.791  -5.209   0.692  1.00  0.00           H  
HETATM   38  H9  UNL     1       3.452  -3.502  -1.097  1.00  0.00           H  
HETATM   39  H10 UNL     1       1.372   1.186  -1.630  1.00  0.00           H  
HETATM   40  H11 UNL     1       6.313   3.006   0.611  1.00  0.00           H  
HETATM   41  H12 UNL     1       6.535   1.927   2.093  1.00  0.00           H  
HETATM   42  H13 UNL     1       7.058   1.391   0.457  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.793   3.886   0.730  1.00  0.00           H  
HETATM   44  H15 UNL     1      -6.312   3.148   2.345  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    7
CONECT    3    4   33
CONECT    4    5    5   29
CONECT    5    6   27
CONECT    6    7    7   34
CONECT    7    8
CONECT    8    9   35   36
CONECT    9   10   10   11
CONECT   11   12   15   15
CONECT   12   13
CONECT   13   14   14   37
CONECT   14   15   38
CONECT   15   16
CONECT   16   17   17   18   18
CONECT   16   19
CONECT   19   20   39
CONECT   20   21   25   25
CONECT   21   22
CONECT   22   23   23
CONECT   23   24   25
CONECT   24   40   41   42
CONECT   25   26
CONECT   27   28
CONECT   28   29   43   44
END

HMDB0015629
     RDKit          3D
Sitaxentan
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2292   -1.3624   -1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736   -0.2474   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.1823   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9060    1.2169    0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251    1.8101    0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    1.3714    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.3417   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -0.1707   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344   -1.4310    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.8249    0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159   -2.3063    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -3.7519    1.0335 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -4.3091    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -3.3731   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -2.3408   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.1010   -1.9607 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0295   -1.2201   -3.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -1.3637   -2.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.4745   -1.2901 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.8039   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990    0.6777    0.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594    1.0471    1.6166 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219    1.4538    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2924    1.9603    1.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440    1.2962   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.6401   -2.0651 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3350    2.7966    1.7874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6889    3.0292    1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8298    0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7347   -1.1249   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.6541   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7195   -2.2563   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5206   -0.2877   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579    1.8366    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -0.1141   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.6379   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -5.2087    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -3.5018   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.1864   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133    3.0056    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5352    1.9271    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0575    1.3910    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933    3.8857    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3120    3.1482    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
  7  2  1  0
 15 11  2  0
 25 20  2  0
 29  4  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 28 43  1  0
 28 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sitaxsentan	HMDB
TBC-11251	HMDB
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamide	MeSH
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-O-toly)acetyl)-3-thiophenesulfonamide	MeSH

Chemical Formula

C₁₈H₁₅ClN₂O₆S₂

Average Molecular Weight

454.905

Monoisotopic Molecular Weight

454.006005309

IUPAC Name

N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

Traditional Name

thelin

CAS Registry Number

210421-64-0

SMILES

CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl

InChI Identifier

InChI=1S/C18H15ClN2O6S2/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18/h3-5,7,21H,6,8H2,1-2H3

InChI Key

PHWXUGHIIBDVKD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Aryl alkyl ketone
Aryl ketone
Aryl chloride
Aryl halide
Benzenoid
Organosulfonic acid amide
Azole
Isoxazole
Heteroaromatic compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Thiophene
Sulfonyl
Ketone
Oxacycle
Acetal
Azacycle
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015629)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.35	ALOGPS
logP	3.09	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	0.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	107.73 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.8 m³·mol⁻¹	ChemAxon
Polarizability	43.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	190.091	30932474
DeepCCS	[M-H]-	187.709	30932474
DeepCCS	[M-2H]-	221.896	30932474
DeepCCS	[M+Na]+	196.946	30932474
AllCCS	[M+H]+	199.4	32859911
AllCCS	[M+H-H2O]+	196.9	32859911
AllCCS	[M+NH4]+	201.7	32859911
AllCCS	[M+Na]+	202.3	32859911
AllCCS	[M-H]-	194.5	32859911
AllCCS	[M+Na-2H]-	194.4	32859911
AllCCS	[M+HCOO]-	194.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sitaxentan	CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl	5295.1	Standard polar	33892256
Sitaxentan	CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl	3457.5	Standard non polar	33892256
Sitaxentan	CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl	3474.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sitaxentan,1TMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C)C=CS1)OCO2	3456.3	Semi standard non polar	33892256
Sitaxentan,1TMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C)C=CS1)OCO2	3365.5	Standard non polar	33892256
Sitaxentan,1TMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C)C=CS1)OCO2	5007.4	Standard polar	33892256
Sitaxentan,1TBDMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C(C)(C)C)C=CS1)OCO2	3656.7	Semi standard non polar	33892256
Sitaxentan,1TBDMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C(C)(C)C)C=CS1)OCO2	3580.1	Standard non polar	33892256
Sitaxentan,1TBDMS,isomer #1	CC1=CC2=C(C=C1CC(=O)C1=C(S(=O)(=O)N(C3=C(Cl)C(C)=NO3)[Si](C)(C)C(C)(C)C)C=CS1)OCO2	4988.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sitaxentan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2911100000-bc2a1c237a5d20fc7fdd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sitaxentan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sitaxentan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Sitaxentan 10V, Positive-QTOF	splash10-0a4i-0012900000-ce9abb5f9d34eeec4e75	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 20V, Positive-QTOF	splash10-0a4r-0953700000-bf4f0740a903bbe272bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 40V, Positive-QTOF	splash10-052u-3390000000-26c07fb81659836de3aa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 10V, Negative-QTOF	splash10-0udi-0001900000-89731203423f9c2c4f61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 20V, Negative-QTOF	splash10-004i-1291600000-b346cc1802382a37696a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 40V, Negative-QTOF	splash10-0a4l-9410000000-8a91a08da2a0b22f85af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 10V, Positive-QTOF	splash10-0a4i-0001900000-4603fc4b43ea34c94da3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 20V, Positive-QTOF	splash10-0006-0900200000-4603223331cb368e057e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 40V, Positive-QTOF	splash10-009t-1930100000-1655132c3e1392943c27	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 10V, Negative-QTOF	splash10-0udi-0000900000-c85f93916432b4dbe289	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 20V, Negative-QTOF	splash10-0udj-0136900000-dd6a50653785ff673c2c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitaxentan 40V, Negative-QTOF	splash10-03di-2289500000-62d0e1afc39abb8eb9e8	2021-10-11	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 DB06268	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06268	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06268

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

187436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sitaxentan

METLIN ID

Not Available

PubChem Compound

216235

PDB ID

Not Available

ChEBI ID

123417

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

Stavros F, Kramer WG, Wilkins MR: The effects of sitaxentan on sildenafil pharmacokinetics and pharmacodynamics in healthy subjects. Br J Clin Pharmacol. 2010 Jan;69(1):23-6. doi: 10.1111/j.1365-2125.2009.03541.x. [PubMed:20078609 ]
Barst RJ, Rich S, Widlitz A, Horn EM, McLaughlin V, McFarlin J: Clinical efficacy of sitaxsentan, an endothelin-A receptor antagonist, in patients with pulmonary arterial hypertension: open-label pilot study. Chest. 2002 Jun;121(6):1860-8. [PubMed:12065350 ]

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

Pulido T, Sandoval J, Roquet I, Gutierrez R, Rueda T, Pena H, Santos E, Miranda MT, Lupi E: Interaction of acenocoumarol and sitaxentan in pulmonary arterial hypertension. Eur J Clin Invest. 2009 Jun;39 Suppl 2:14-8. doi: 10.1111/j.1365-2362.2009.02116.x. [PubMed:19335742 ]
Opitz CF, Ewert R, Kirch W, Pittrow D: Inhibition of endothelin receptors in the treatment of pulmonary arterial hypertension: does selectivity matter? Eur Heart J. 2008 Aug;29(16):1936-48. doi: 10.1093/eurheartj/ehn234. Epub 2008 Jun 17. [PubMed:18562303 ]
Barst RJ, Rich S, Widlitz A, Horn EM, McLaughlin V, McFarlin J: Clinical efficacy of sitaxsentan, an endothelin-A receptor antagonist, in patients with pulmonary arterial hypertension: open-label pilot study. Chest. 2002 Jun;121(6):1860-8. [PubMed:12065350 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Barst RJ, Rich S, Widlitz A, Horn EM, McLaughlin V, McFarlin J: Clinical efficacy of sitaxsentan, an endothelin-A receptor antagonist, in patients with pulmonary arterial hypertension: open-label pilot study. Chest. 2002 Jun;121(6):1860-8. [PubMed:12065350 ]

Enzyme Details

4. 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

Girgis RE, Frost AE, Hill NS, Horn EM, Langleben D, McLaughlin VV, Oudiz RJ, Robbins IM, Seibold JR, Shapiro S, Tapson VF, Barst RJ: Selective endothelin A receptor antagonism with sitaxsentan for pulmonary arterial hypertension associated with connective tissue disease. Ann Rheum Dis. 2007 Nov;66(11):1467-72. Epub 2007 May 1. [PubMed:17472992 ]
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

5. 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

Girgis RE, Frost AE, Hill NS, Horn EM, Langleben D, McLaughlin VV, Oudiz RJ, Robbins IM, Seibold JR, Shapiro S, Tapson VF, Barst RJ: Selective endothelin A receptor antagonism with sitaxsentan for pulmonary arterial hypertension associated with connective tissue disease. Ann Rheum Dis. 2007 Nov;66(11):1467-72. Epub 2007 May 1. [PubMed:17472992 ]
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 ]

Showing metabocard for Sitaxentan (HMDB0015629)

MOL for HMDB0015629 (Sitaxentan)

3D MOL for HMDB0015629 (Sitaxentan)

3D SDF for HMDB0015629 (Sitaxentan)

3D-SDF for HMDB0015629 (Sitaxentan)

PDB for HMDB0015629 (Sitaxentan)

3D PDB for HMDB0015629 (Sitaxentan)

SMILES for HMDB0015629 (Sitaxentan)

INCHI for HMDB0015629 (Sitaxentan)

Structure for HMDB0015629 (Sitaxentan)

3D Structure for HMDB0015629 (Sitaxentan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References