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

ID: ALA117224

PubChem CID: 10765092

Max Phase: Preclinical

Molecular Formula: C23H30N2O4S

Molecular Weight: 430.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)C2CCCCC2)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C23H30N2O4S/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/h4-5,11,13-15,17,22,25H,1-3,6-10,12,16H2,(H,26,27)

Standard InChI Key:  AEZWAALFFBECGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.4875   -4.6792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7625   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -4.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6125   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -8.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -8.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8792   -6.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  2  0
  4 13  1  0
  5  1  1  0
  6  1  1  0
  7 16  1  0
  8 21  1  0
  9  7  2  0
 10 15  2  0
 11 22  1  0
 12 10  1  0
 13 11  2  0
 14  4  1  0
 15 11  1  0
 16 17  1  0
 17 10  1  0
 18  7  1  0
 19 14  1  0
 20  5  1  0
 21 19  2  0
 22 20  1  0
 23 27  1  0
 24  6  1  0
 25  6  1  0
 26 19  1  0
 27 26  2  0
 28 25  1  0
 29 24  1  0
 30 28  1  0
 30 29  1  0
  4 12  2  0
 23  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117224

   3-[3-(2-Cyclohexanesulfonylamino-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: 430.57

Molecular Weight (Monoisotopic): 430.1926

AlogP: 3.48

#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: 2.65

CX LogD: 0.90

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: -0.56

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