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

ID: ALA116196

PubChem CID: 10764803

Max Phase: Preclinical

Molecular Formula: C23H24N2O4S

Molecular Weight: 424.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H24N2O4S/c26-23(27)9-8-18-13-19(15-21(14-18)16-20-5-4-11-24-17-20)10-12-25-30(28,29)22-6-2-1-3-7-22/h1-7,11,13-15,17,25H,8-10,12,16H2,(H,26,27)

Standard InChI Key:  ITVKVHZSOCJLEY-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
    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
    2.4167    0.1083    0.0000 C   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
   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
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    8.1250    0.1458    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
    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
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    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
    1.7042   -0.3042    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
    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
    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
    0.9917    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  2  0
  4  1  1  0
  5 13  2  0
  6  1  1  0
  7 16  1  0
  8 21  1  0
  9  7  2  0
 10 15  1  0
 11 22  1  0
 12 10  2  0
 13 11  1  0
 14  5  1  0
 15 11  2  0
 16 17  1  0
 17 10  1  0
 18  7  1  0
 19 14  1  0
 20  6  1  0
 21 19  2  0
 22 20  1  0
 23 27  1  0
 24  4  2  0
 25  4  1  0
 26 19  1  0
 27 26  2  0
 28 24  1  0
 29 25  2  0
 30 29  1  0
 28 30  2  0
 12  5  1  0
 23  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA116196

   3-[3-(2-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: 424.52

Molecular Weight (Monoisotopic): 424.1457

AlogP: 3.21

#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: 4.06

CX Basic pKa: 5.43

CX LogP: 2.66

CX LogD: 0.91

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -0.72

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