3-[3-(2-Benzenesulfonyl-ethyl)-5-pyridin-3-ylmethyl-phenyl]-propionic acid

ID: ALA115805

PubChem CID: 10549479

Max Phase: Preclinical

Molecular Formula: C23H23NO4S

Molecular Weight: 409.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCS(=O)(=O)c2ccccc2)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C23H23NO4S/c25-23(26)9-8-18-13-19(10-12-29(27,28)22-6-2-1-3-7-22)15-21(14-18)16-20-5-4-11-24-17-20/h1-7,11,13-15,17H,8-10,12,16H2,(H,25,26)

Standard InChI Key:  HOJVQVXWXVDWQZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3667    0.3375    0.0000 S   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
    3.6417   -0.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    1.1625    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
    3.6542    0.7500    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
    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
    7.9167   -0.9792    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
    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
    5.7917    0.3083    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
    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
    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
   10.7667   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    0.3375    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
    2.2167    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 13  1  0
  3  1  2  0
  4  1  2  0
  5  1  1  0
  6  1  1  0
  7 17  1  0
  8 21  1  0
  9  7  2  0
 10 16  1  0
 11 15  2  0
 12 11  1  0
 13 10  2  0
 14  2  1  0
 15 10  1  0
 16  5  1  0
 17 18  1  0
 18 11  1  0
 19  7  1  0
 20 14  1  0
 21 20  2  0
 22 26  1  0
 23  6  2  0
 24  6  1  0
 25 20  1  0
 26 25  2  0
 27 24  2  0
 28 23  1  0
 29 27  1  0
 29 28  2  0
  2 12  2  0
 22  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA115805

   3-[3-(2-Benzenesulfonyl-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: 409.51

Molecular Weight (Monoisotopic): 409.1348

AlogP: 3.71

#Rotatable Bonds: 9

Polar Surface Area: 84.33

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.77

CX Basic pKa: 5.42

CX LogP: 2.72

CX LogD: 0.99

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -0.67

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