2-(4-(ethylsulfonyl)phenyl)-N-(4-(2-methyl-1-oxo-1-(piperidin-1-yl)propan-2-yl)phenyl)acetamide

ID: ALA4287342

PubChem CID: 145991576

Max Phase: Preclinical

Molecular Formula: C25H32N2O4S

Molecular Weight: 456.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)c1ccc(CC(=O)Nc2ccc(C(C)(C)C(=O)N3CCCCC3)cc2)cc1

Standard InChI:  InChI=1S/C25H32N2O4S/c1-4-32(30,31)22-14-8-19(9-15-22)18-23(28)26-21-12-10-20(11-13-21)25(2,3)24(29)27-16-6-5-7-17-27/h8-15H,4-7,16-18H2,1-3H3,(H,26,28)

Standard InChI Key:  DWMTUTVNKOTWEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   18.6757   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6798   -8.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3855   -8.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3412   -7.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7539   -8.6300    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.1623   -7.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3883   -9.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3872   -9.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0952  -10.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8049   -9.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8020   -9.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0934   -8.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5132  -10.2734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2203   -9.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9286  -10.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2190   -9.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6357   -9.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3427  -10.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0493   -9.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0485   -9.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3352   -8.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6315   -9.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4639   -9.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1704   -8.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9729   -9.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2651   -8.6388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9731   -9.8644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2678   -7.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5641   -7.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8541   -7.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8523   -8.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5605   -9.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  2  0
  6  5  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20  5  1  0
  5 23  1  0
 23 24  1  0
  7  2  1  0
  2 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 26 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4287342

   ---

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: 456.61

Molecular Weight (Monoisotopic): 456.2083

AlogP: 3.95

#Rotatable Bonds: 7

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.68

Np Likeness Score: -1.75

References

1. Sasaki Y, Odan M, Yamamoto S, Kida S, Ueyama A, Shimizu M, Haruna T, Watanabe A, Okuno T..  (2018)  Discovery of a potent orally bioavailable retinoic acid receptor-related orphan receptor-gamma-t (RORγt) inhibitor, S18-000003.,  28  (22): [PMID:30301676] [10.1016/j.bmcl.2018.09.032]

Source

Source(1):

• Scientific Literature