3-{3-[2-(2,2-Dimethyl-propane-1-sulfonylamino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

ID: ALA324059

PubChem CID: 10669723

Max Phase: Preclinical

Molecular Formula: C22H30N2O4S

Molecular Weight: 418.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)CS(=O)(=O)NCCc1cc(CCC(=O)O)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C22H30N2O4S/c1-22(2,3)16-29(27,28)24-10-8-18-11-17(6-7-21(25)26)12-20(13-18)14-19-5-4-9-23-15-19/h4-5,9,11-13,15,24H,6-8,10,14,16H2,1-3H3,(H,25,26)

Standard InChI Key:  JABUGNFZMXGDBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    3.4792   -4.7167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -5.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -4.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -8.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -5.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -7.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -6.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -8.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8750   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  2  0
  4 14  1  0
  5 17  1  0
  6  1  1  0
  7  1  1  0
  8 22  1  0
  9  5  2  0
 10 16  2  0
 11  6  1  0
 12 23  1  0
 13 10  1  0
 14 12  2  0
 15  4  1  0
 16 12  1  0
 17 18  1  0
 18 10  1  0
 19  5  1  0
 20 15  1  0
 21  7  1  0
 22 20  2  0
 23 21  1  0
 24 29  1  0
 25 11  1  0
 26 11  1  0
 27 11  1  0
 28 20  1  0
 29 28  2  0
  4 13  2  0
 24  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA324059

   3-{3-[2-(2,2-Dimethyl-propane-1-sulfonylamino)-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: 418.56

Molecular Weight (Monoisotopic): 418.1926

AlogP: 3.20

#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: 2.32

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -0.55

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