3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(pyridin-3-yloxy)-phenyl]-propionic acid

ID: ALA117538

PubChem CID: 10551940

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O5S

Molecular Weight: 460.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)c2ccc(Cl)cc2)cc(Oc2cccnc2)c1

Standard InChI:  InChI=1S/C22H21ClN2O5S/c23-18-4-6-21(7-5-18)31(28,29)25-11-9-17-12-16(3-8-22(26)27)13-20(14-17)30-19-2-1-10-24-15-19/h1-2,4-7,10,12-15,25H,3,8-9,11H2,(H,26,27)

Standard InChI Key:  HWVYQQTUUJCMIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.1375   -0.3042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -1.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2167    0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -3.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4167   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7125   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -3.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8542   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  2  0
  5 16  2  0
  6  1  1  0
  7 18  1  0
  8  5  1  0
  9 27  1  0
 10  7  2  0
 11 17  1  0
 12 28  1  0
 13  2  1  0
 14  2  2  0
 15 11  2  0
 16 12  1  0
 17 12  2  0
 18 20  1  0
 19 23  2  0
 20 11  1  0
 21  7  1  0
 22  8  1  0
 23 14  1  0
 24 13  2  0
 25 19  1  0
 26  6  1  0
 27 22  2  0
 28 26  1  0
 29 31  1  0
 30 22  1  0
 31 30  2  0
 19 24  1  0
  5 15  1  0
 29  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117538

   3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(pyridin-3-yloxy)-phenyl]-propionic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 460.94

Molecular Weight (Monoisotopic): 460.0860

AlogP: 4.07

#Rotatable Bonds: 10

Polar Surface Area: 105.59

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: 4.65

CX LogP: 2.84

CX LogD: 0.53

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.11

References

1. Dickinson RP, Dack KN, Long CJ, Steele J..  (1997)  Thromboxane modulating agents. 3. 1H-imidazol-1-ylalkyl- and 3-pyridinylalkyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists.,  40  (21): [PMID:9341919] [10.1021/jm9702793]

Source

Source(1):

• Scientific Literature