3-(3-{2-[(4-Chloro-benzenesulfonyl)-methyl-amino]-ethyl}-5-pyridin-3-ylmethyl-phenyl)-propionic acid

ID: ALA117294

PubChem CID: 10576417

Max Phase: Preclinical

Molecular Formula: C24H25ClN2O4S

Molecular Weight: 472.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCc1cc(CCC(=O)O)cc(Cc2cccnc2)c1)S(=O)(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C24H25ClN2O4S/c1-27(32(30,31)23-7-5-22(25)6-8-23)12-10-19-13-18(4-9-24(28)29)14-21(15-19)16-20-3-2-11-26-17-20/h2-3,5-8,11,13-15,17H,4,9-10,12,16H2,1H3,(H,28,29)

Standard InChI Key:  FPQAOWGFSPHQGL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.6500   -0.0667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667    0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7792   -0.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000   -3.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6500    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -3.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -1.6917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3542   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0750    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7667   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3375   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  1  2  0
  6 15  1  0
  7 19  1  0
  8 28  1  0
  9  7  2  0
 10  2  1  0
 11 20  1  0
 12 18  2  0
 13  3  1  0
 14  3  2  0
 15 11  2  0
 16 12  1  0
 17  6  1  0
 18 11  1  0
 19 22  1  0
 20 10  1  0
 21 24  2  0
 22 12  1  0
 23  7  1  0
 24 14  1  0
 25 13  2  0
 26 21  1  0
 27 17  1  0
 28 27  2  0
 29  2  1  0
 30 32  1  0
 31 27  1  0
 32 31  2  0
 25 21  1  0
  6 16  2  0
 30  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117294

   3-(3-{2-[(4-Chloro-benzenesulfonyl)-methyl-amino]-ethyl}-5-pyridin-3-ylmethyl-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: 472.99

Molecular Weight (Monoisotopic): 472.1224

AlogP: 4.21

#Rotatable Bonds: 10

Polar Surface Area: 87.57

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: 5.42

CX LogP: 3.46

CX LogD: 1.71

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -0.95

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