2-(4-(ethylsulfonyl)phenyl)-N-(4-(1-(indolin-1-yl)-2-methyl-1-oxopropan-2-yl)phenyl)acetamide

ID: ALA4282801

PubChem CID: 145981346

Max Phase: Preclinical

Molecular Formula: C28H30N2O4S

Molecular Weight: 490.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)c1ccc(CC(=O)Nc2ccc(C(C)(C)C(=O)N3CCc4ccccc43)cc2)cc1

Standard InChI:  InChI=1S/C28H30N2O4S/c1-4-35(33,34)24-15-9-20(10-16-24)19-26(31)29-23-13-11-22(12-14-23)28(2,3)27(32)30-18-17-21-7-5-6-8-25(21)30/h5-16H,4,17-19H2,1-3H3,(H,29,31)

Standard InChI Key:  GXNJWSJMKRTTPH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.0059  -12.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0100  -13.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7157  -13.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6714  -12.8481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0841  -13.5579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.4925  -12.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1350  -14.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.4236  -13.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8434  -15.2013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5505  -14.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2588  -15.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5492  -13.9744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   23.9617  -13.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.5006  -13.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3031  -13.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5953  -13.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3033  -14.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5092  -12.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7099  -12.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3032  -13.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5069  -13.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2547  -14.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8049  -14.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5992  -14.6725    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
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 12  7  1  0
 10 13  1  0
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 18 19  1  0
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 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
 28 29  1  0
 29 31  1  0
 30 26  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4282801

   ---

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: 490.63

Molecular Weight (Monoisotopic): 490.1926

AlogP: 4.53

#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: 4.47

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.53

Np Likeness Score: -1.67

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