3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(1-pyridin-3-yl-vinyl)-phenyl]-propionic acid

ID: ALA117561

PubChem CID: 10648075

Max Phase: Preclinical

Molecular Formula: C24H23ClN2O4S

Molecular Weight: 470.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(c1cccnc1)c1cc(CCNS(=O)(=O)c2ccc(Cl)cc2)cc(CCC(=O)O)c1

Standard InChI:  InChI=1S/C24H23ClN2O4S/c1-17(20-3-2-11-26-16-20)21-14-18(4-9-24(28)29)13-19(15-21)10-12-27-32(30,31)23-7-5-22(25)6-8-23/h2-3,5-8,11,13-16,27H,1,4,9-10,12H2,(H,28,29)

Standard InChI Key:  FMMSMSALGORHKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.4750   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -1.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917    0.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125    0.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -0.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -3.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4792    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5667   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -3.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375    1.4458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  2  0
  3  2  1  0
  4  1  1  0
  5  1  2  0
  6  1  2  0
  7  1  1  0
  8 12  2  0
  9 16  1  0
 10 20  1  0
 11  3  1  0
 12 19  1  0
 13 28  1  0
 14  3  2  0
 15 10  2  0
 16 29  1  0
 17  4  1  0
 18  4  2  0
 19 16  2  0
 20 22  1  0
 21 25  2  0
 22 12  1  0
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 24 17  2  0
 25 18  1  0
 26 21  1  0
 27  7  1  0
 28 11  2  0
 29 27  1  0
 30 32  1  0
 31 11  1  0
 32 31  2  0
 21 24  1  0
  8  2  1  0
 30 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117561

   3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(1-pyridin-3-yl-vinyl)-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: 470.98

Molecular Weight (Monoisotopic): 470.1067

AlogP: 4.33

#Rotatable Bonds: 10

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.93

CX Basic pKa: 4.80

CX LogP: 3.63

CX LogD: 1.37

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.82

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