5-Chloro-3-methyl-N-(8-propyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-1H-indole-2-carboxamide

ID: ALA4644053

PubChem CID: 156017486

Max Phase: Preclinical

Molecular Formula: C21H26ClN3O2S

Molecular Weight: 419.98

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC1CCC2(CC1)SCC(=O)N2NC(=O)c1[nH]c2ccc(Cl)cc2c1C

Standard InChI:  InChI=1S/C21H26ClN3O2S/c1-3-4-14-7-9-21(10-8-14)25(18(26)12-28-21)24-20(27)19-13(2)16-11-15(22)5-6-17(16)23-19/h5-6,11,14,23H,3-4,7-10,12H2,1-2H3,(H,24,27)

Standard InChI Key:  NAJUFCOPJGILEH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.8478  -23.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1021  -22.6393    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4350  -22.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7763  -22.6393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7415  -20.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7415  -21.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1562  -21.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1562  -20.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4467  -20.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9532  -22.6337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5453  -21.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7240  -21.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9628  -21.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467  -21.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2378  -22.5775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4582  -22.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4655  -21.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7597  -21.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462  -21.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0428  -22.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491  -22.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5025  -20.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368  -21.0728    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5411  -24.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4457  -19.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1529  -19.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1519  -18.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 12 14  2  0
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 19 20  2  0
 20 21  1  0
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 22 17  1  0
 15 23  1  0
 20 24  1  0
  1 25  2  0
 10 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644053

   ---

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: 419.98

Molecular Weight (Monoisotopic): 419.1434

AlogP: 5.04

#Rotatable Bonds: 4

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: 4.74

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -0.61

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