2-(4-chloro-1H-indol-3-ylthio)-N-(2-ethoxyphenyl)acetamide

ID: ALA4745374

PubChem CID: 162647559

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O2S

Molecular Weight: 360.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccccc1NC(=O)CSc1c[nH]c2cccc(Cl)c12

Standard InChI:  InChI=1S/C18H17ClN2O2S/c1-2-23-15-9-4-3-7-13(15)21-17(22)11-24-16-10-20-14-8-5-6-12(19)18(14)16/h3-10,20H,2,11H2,1H3,(H,21,22)

Standard InChI Key:  MUXXHIXGEHILJW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   27.7597  -16.3026    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.1638  -17.7106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9666  -17.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0509  -16.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7550  -17.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2975  -16.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0422  -15.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2407  -15.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6991  -16.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9573  -16.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4746  -16.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1848  -16.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8982  -16.7096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1816  -15.4784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6085  -16.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3213  -16.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0270  -16.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0242  -15.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3100  -15.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6031  -15.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3233  -17.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0320  -17.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0339  -18.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5899  -15.0028    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  2  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  4  1  1  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745374

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.87

Molecular Weight (Monoisotopic): 360.0699

AlogP: 4.95

#Rotatable Bonds: 6

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.87

References

1. Zhang GN,Li Q,Zhao J,Zhang X,Xu Z,Wang Y,Fu Y,Shan Q,Zheng Y,Wang J,Zhu M,Li Z,Cen S,He J,Wang Y.  (2020)  Design and synthesis of 2-((1H-indol-3-yl)thio)-N-phenyl-acetamides as novel dual inhibitors of respiratory syncytial virus and influenza virus A.,  186  [PMID:31734025] [10.1016/j.ejmech.2019.111861]

Source

Source(1):

• Scientific Literature