5-Chloro-3-methyl-N-(2,7,7,9-tetramethyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-1H-indole-2-carboxamide

ID: ALA4639120

PubChem CID: 156013455

Max Phase: Preclinical

Molecular Formula: C22H28ClN3O2S

Molecular Weight: 434.01

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)NN2C(=O)C(C)SC23CC(C)CC(C)(C)C3)[nH]c2ccc(Cl)cc12

Standard InChI:  InChI=1S/C22H28ClN3O2S/c1-12-9-21(4,5)11-22(10-12)26(20(28)14(3)29-22)25-19(27)18-13(2)16-8-15(23)6-7-17(16)24-18/h6-8,12,14,24H,9-11H2,1-5H3,(H,25,27)

Standard InChI Key:  FCKGHHXRAMQUFZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.3731   -6.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6275   -5.7424    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9604   -5.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3017   -5.7424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -4.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815   -4.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9721   -3.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4785   -5.7368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0706   -5.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4882   -4.3173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7721   -4.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7631   -5.6806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9835   -5.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909   -4.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -4.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682   -5.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745   -5.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278   -3.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -4.1759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0665   -7.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3899   -3.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2627   -3.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4744   -3.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8532   -7.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6 10  1  0
  7  4  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 18  1  0
 17 16  1  0
 16 13  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
 15 23  1  0
 20 24  1  0
  1 25  2  0
  9 26  1  0
  6 27  1  0
  6 28  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4639120

   ---

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: 434.01

Molecular Weight (Monoisotopic): 433.1591

AlogP: 5.28

#Rotatable Bonds: 2

Polar Surface Area: 65.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.39

CX Basic pKa: ┄

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.55

References

1. Cihan-Üstündağ G, Zopun M, Vanderlinden E, Ozkirimli E, Persoons L, Çapan G, Naesens L..  (2020)  Superior inhibition of influenza virus hemagglutinin-mediated fusion by indole-substituted spirothiazolidinones.,  28  (1): [PMID:31753804] [10.1016/j.bmc.2019.115130]

Source

Source(1):

• Scientific Literature