3-{3-[2-(4-Bromo-benzenesulfonylamino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

ID: ALA118008

PubChem CID: 10744075

Max Phase: Preclinical

Molecular Formula: C23H23BrN2O4S

Molecular Weight: 503.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)c2ccc(Br)cc2)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C23H23BrN2O4S/c24-21-4-6-22(7-5-21)31(29,30)26-11-9-18-12-17(3-8-23(27)28)13-20(14-18)15-19-2-1-10-25-16-19/h1-2,4-7,10,12-14,16,26H,3,8-9,11,15H2,(H,27,28)

Standard InChI Key:  YSNQLPNLRJCVLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    3.9667   -4.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -5.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -8.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0917   -4.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -8.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -5.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -7.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -8.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -6.3542    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.6750   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0792   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -6.0917    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 15  1  0
  6  1  1  0
  7 18  1  0
  8 27  1  0
  9  7  2  0
 10 17  2  0
 11 28  1  0
 12  2  1  0
 13  2  2  0
 14 10  1  0
 15 11  2  0
 16  5  1  0
 17 11  1  0
 18 20  1  0
 19 23  2  0
 20 10  1  0
 21  7  1  0
 22 12  2  0
 23 13  1  0
 24 19  1  0
 25 16  1  0
 26  6  1  0
 27 25  2  0
 28 26  1  0
 29 31  1  0
 30 25  1  0
 31 30  2  0
 19 22  1  0
  5 14  2  0
 29  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA118008

   3-{3-[2-(4-Bromo-benzenesulfonylamino)-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: 503.42

Molecular Weight (Monoisotopic): 502.0562

AlogP: 3.97

#Rotatable Bonds: 10

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.06

CX Basic pKa: 5.43

CX LogP: 3.43

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -0.78

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