8-[(4-Chloro-benzenesulfonyl)-methyl-amino]-7-pyridin-3-yl-octanoic acid hydrochloride

ID: ALA538545

PubChem CID: 11743126

Max Phase: Preclinical

Molecular Formula: C20H26Cl2N2O4S

Molecular Weight: 424.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CC(CCCCCC(=O)O)c1cccnc1)S(=O)(=O)c1ccc(Cl)cc1.Cl

Standard InChI:  InChI=1S/C20H25ClN2O4S.ClH/c1-23(28(26,27)19-11-9-18(21)10-12-19)15-17(16-7-5-13-22-14-16)6-3-2-4-8-20(24)25;/h5,7,9-14,17H,2-4,6,8,15H2,1H3,(H,24,25);1H

Standard InChI Key:  GTTYLAMVQVQNPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.2983   -3.3781    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -3.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383   -2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378   -0.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -5.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004   -5.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7983   -6.0102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9398   -5.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -4.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -3.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013   -5.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -5.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7941   -7.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -6.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1961   -7.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996   -5.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -5.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4930   -8.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  2  6  2  0
  2  7  2  0
  5  9  1  0
  8 11  2  0
  4 12  1  0
  4 13  2  0
  9 14  1  0
  8 16  1  0
 13 17  1  0
 15 17  2  0
 12 18  2  0
 15 18  1  0
 15 19  1  0
  3 20  1  0
 10 21  1  0
 14 21  2  0
  8 22  1  0
 10 23  2  0
  9 24  1  0
 14 25  1  0
 22 26  1  0
 24 27  1  0
 26 28  1  0
 27 28  1  0
 23 29  1  0
 25 29  2  0
M  END

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: 424.95

Molecular Weight (Monoisotopic): 424.1224

AlogP: 4.17

#Rotatable Bonds: 11

Polar Surface Area: 87.57

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.91

CX Basic pKa: 4.95

CX LogP: 2.79

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.88

References

1. Main AJ, Goldstein R, Cohen DS, Furness P, Lee W..  (1992)  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 2. Synthesis and biological activity of 8-(benzenesulfonamido)-7-(3-pyridinyl)octaonic acid and related compounds.,  35  (23): [PMID:1447736] [10.1021/jm00101a013]

Source

Source(1):

• Scientific Literature