8-(4-Naphthalen-2-yl-benzenesulfonylamino)-7-pyridin-3-yl-octanoic acid hydrochloride

ID: ALA541097

PubChem CID: 44357794

Max Phase: Preclinical

Molecular Formula: C29H31ClN2O4S

Molecular Weight: 502.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)CCCCCC(CNS(=O)(=O)c1ccc(-c2ccc3ccccc3c2)cc1)c1cccnc1

Standard InChI:  InChI=1S/C29H30N2O4S.ClH/c32-29(33)11-3-1-2-9-27(26-10-6-18-30-20-26)21-31-36(34,35)28-16-14-23(15-17-28)25-13-12-22-7-4-5-8-24(22)19-25;/h4-8,10,12-20,27,31H,1-3,9,11,21H2,(H,32,33);1H

Standard InChI Key:  XJOFFWYWHXPMFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    5.0929    4.5320    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.7912    3.7794    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7822    5.2802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    3.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8267    4.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8343    3.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681    7.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9605    8.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0769    6.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2238    8.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125    0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985    3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3625    8.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0678    7.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778    6.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6686    7.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620    8.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9463    9.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3484    9.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7618    8.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8680    7.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4679    7.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1619    8.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6403   10.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  6  2  0
  2  7  2  0
  5  8  1  0
  5  9  1  0
  8 11  2  0
  3 13  1  0
  5 14  2  0
 10 15  2  0
  4 16  2  0
  4 17  1  0
  9 18  1  0
 17 18  2  0
  9 19  2  0
 16 19  1  0
 11 20  1  0
 14 21  1  0
 20 21  2  0
 13 23  1  0
 22 23  1  0
 10 24  1  0
 12 25  1  0
 22 25  2  0
 10 26  1  0
 12 27  2  0
 11 28  1  0
 22 29  1  0
 20 30  1  0
 23 31  1  0
 26 32  1  0
 31 33  1  0
 32 34  1  0
 33 34  1  0
 27 35  1  0
 29 35  2  0
 28 36  2  0
 30 37  2  0
 36 37  1  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: 502.64

Molecular Weight (Monoisotopic): 502.1926

AlogP: 6.00

#Rotatable Bonds: 12

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.00

CX Basic pKa: 4.96

CX LogP: 4.63

CX LogD: 2.48

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: -0.47

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