3-{3-Pyridin-3-ylmethyl-5-[2-(toluene-4-sulfonylamino)-ethyl]-phenyl}-propionic acid

ID: ALA116704

PubChem CID: 10670672

Max Phase: Preclinical

Molecular Formula: C24H26N2O4S

Molecular Weight: 438.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NCCc2cc(CCC(=O)O)cc(Cc3cccnc3)c2)cc1

Standard InChI:  InChI=1S/C24H26N2O4S/c1-18-4-7-23(8-5-18)31(29,30)26-12-10-20-13-19(6-9-24(27)28)14-22(15-20)16-21-3-2-11-25-17-21/h2-5,7-8,11,13-15,17,26H,6,9-10,12,16H2,1H3,(H,27,28)

Standard InChI Key:  BWGGIGNNYKWFDR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.1250   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -5.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0750   -8.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9667   -4.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7875   -8.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4042   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -5.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5417   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2625   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9542   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5250   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -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 26  1  0
  9  7  2  0
 10 17  2  0
 11 27  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 19  1  0
 19 10  1  0
 20  7  1  0
 21 12  2  0
 22 13  1  0
 23 22  2  0
 24 16  1  0
 25  6  1  0
 26 24  2  0
 27 25  1  0
 28 31  1  0
 29 23  1  0
 30 24  1  0
 31 30  2  0
 23 21  1  0
  5 14  2  0
 28  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA116704

   3-{3-Pyridin-3-ylmethyl-5-[2-(toluene-4-sulfonylamino)-ethyl]-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: 438.55

Molecular Weight (Monoisotopic): 438.1613

AlogP: 3.52

#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: 3.17

CX LogD: 1.42

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

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