N-butyloxycarbonyl-2-(4-imidazol-1-ylmethylphenyl)-4-iso-butylbenzenesulfonamide

ID: ALA217673

PubChem CID: 11994289

Max Phase: Preclinical

Molecular Formula: C25H31N3O4S

Molecular Weight: 469.61

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H31N3O4S/c1-4-5-14-32-25(29)27-33(30,31)24-11-8-21(15-19(2)3)16-23(24)22-9-6-20(7-10-22)17-28-13-12-26-18-28/h6-13,16,18-19H,4-5,14-15,17H2,1-3H3,(H,27,29)

Standard InChI Key:  IEKPELSFCDOQBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    1.8861   -4.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050   -3.7127    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3170   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141   -4.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975   -2.9953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322   -3.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -4.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7474   -3.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505   -4.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7531   -5.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4688   -6.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4715   -7.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538   -4.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859   -1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -2.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -2.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938   -2.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728   -3.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -4.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -5.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884   -4.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9072   -0.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900   -0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1721    0.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6843    1.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9008    0.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613   -5.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -6.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775   -6.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -6.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  1  0
 17 20  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  7  9  1  0
 20 21  2  0
 21 13  1  0
  9 10  1  0
 13 22  2  0
 10 11  1  0
 22 23  1  0
 23  1  2  0
  1 20  1  0
 11 12  1  0
 24 25  1  0
 14 24  1  0
 25 26  1  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  2  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
  3  6  1  0
 13 30  1  0
  6  7  1  0
 30 31  1  0
  6  8  2  0
 31 32  1  0
 18 19  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA217673

   N-butyloxycarbonyl-2-(4-imidazol-1-ylmethylphenyl)-4-iso-butylbenzenesulfonamide

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: 469.61

Molecular Weight (Monoisotopic): 469.2035

AlogP: 5.01

#Rotatable Bonds: 10

Polar Surface Area: 90.29

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.93

CX Basic pKa: 6.47

CX LogP: 4.21

CX LogD: 4.70

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -0.87

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]

2. Wallinder C, Botros M, Rosenström U, Guimond MO, Beaudry H, Nyberg F, Gallo-Payet N, Hallberg A, Alterman M..  (2008)  Selective angiotensin II AT2 receptor agonists: Benzamide structure-activity relationships.,  16  (14): [PMID:18599297] [10.1016/j.bmc.2008.05.066]

3. Wallinder C, Sköld C, Botros M, Guimond MO, Hallberg M, Gallo-Payet N, Karlén A, Alterman M..  (2015)  Interconversion of Functional Activity by Minor Structural Alterations in Nonpeptide AT2 Receptor Ligands.,  6  (2): [PMID:25699147] [10.1021/ml500427r]

4. Sallander J, Wallinder C, Hallberg A, Åqvist J, Gutiérrez-de-Terán H..  (2016)  Structural determinants of subtype selectivity and functional activity of angiotensin II receptors.,  26  (4): [PMID:26810314] [10.1016/j.bmcl.2015.10.084]

5. Dosa PI, Amin EA..  (2016)  Tactical Approaches to Interconverting GPCR Agonists and Antagonists.,  59  (3): [PMID:26390077] [10.1021/acs.jmedchem.5b00982]

Source

Source(1):

• Scientific Literature