N-ethyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

ID: ALA386269

PubChem CID: 10160913

Max Phase: Preclinical

Molecular Formula: C21H25N3O4S2

Molecular Weight: 447.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)NS(=O)(=O)c1sc(CC(C)C)cc1-c1ccc(Cn2ccnc2)cc1

Standard InChI:  InChI=1S/C21H25N3O4S2/c1-4-28-21(25)23-30(26,27)20-19(12-18(29-20)11-15(2)3)17-7-5-16(6-8-17)13-24-10-9-22-14-24/h5-10,12,14-15H,4,11,13H2,1-3H3,(H,23,25)

Standard InChI Key:  LPYXRTXXLKVWKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.2027   -0.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016   -1.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164   -1.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -1.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300   -0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    0.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2481   -2.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5030   -3.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -3.6348    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5820   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121    0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254    1.3483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3800    1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9309    1.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    2.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7078    2.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3661   -2.5919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -2.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -3.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -1.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5039   -2.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7994   -3.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2216   -2.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9328   -2.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -4.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979   -4.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7132   -4.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620   -3.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  2  0
 13 14  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  4  5  1  0
 11 18  1  0
  2  3  1  0
 18 19  1  0
  7  8  1  0
 18 20  2  0
  9 10  1  0
 18 21  2  0
 10 11  1  0
 19 22  1  0
 11  7  2  0
 22 23  1  0
  3  7  1  0
 22 24  2  0
  5  6  2  0
 23 25  1  0
  6 12  1  0
 25 26  1  0
  6  1  1  0
  9 27  1  0
 12 13  1  0
 27 28  1  0
 14 15  2  0
 28 29  1  0
  8  9  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA386269

   N-ethyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

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: 447.58

Molecular Weight (Monoisotopic): 447.1286

AlogP: 4.29

#Rotatable Bonds: 8

Polar Surface Area: 90.29

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.61

CX Basic pKa: 6.47

CX LogP: 3.61

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -1.05

References

1. Wu X, Wan Y, Mahalingam AK, Murugaiah AM, Plouffe B, Botros M, Karlén A, Hallberg M, Gallo-Payet N, Alterman M..  (2006)  Selective angiotensin II AT2 receptor agonists: arylbenzylimidazole structure-activity relationships.,  49  (24): [PMID:17125268] [10.1021/jm0606185]

Source

Source(1):

• Scientific Literature