1-(1-(4-Chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-4-yl)-ethyl)piperidine-4-carboxamide

ID: ALA3085944

PubChem CID: 66571217

Max Phase: Preclinical

Molecular Formula: C29H29ClN4O2

Molecular Weight: 501.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCc1ccncc1)C1CCN(C(=O)c2cc3ccccc3n2Cc2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C29H29ClN4O2/c30-25-7-5-22(6-8-25)20-34-26-4-2-1-3-24(26)19-27(34)29(36)33-17-12-23(13-18-33)28(35)32-16-11-21-9-14-31-15-10-21/h1-10,14-15,19,23H,11-13,16-18,20H2,(H,32,35)

Standard InChI Key:  ZCSWCGKOEUTHLD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.6799  -25.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2106  -24.9706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5351  -24.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1236  -23.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5055  -25.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9048  -26.3810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9317  -24.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4740  -27.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8699  -27.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6957  -27.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1241  -27.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.3095  -22.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8932  -22.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3028  -23.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0923  -28.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6634  -29.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9178  -28.5692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4107  -26.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4299  -25.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7326  -24.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0156  -25.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0003  -26.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6983  -26.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9007  -21.3427    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.3144  -29.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1399  -29.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5365  -30.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1040  -30.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5000  -31.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3263  -31.4809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7552  -30.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3568  -30.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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 11 12  1  0
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  5 14  2  0
  5 18  1  0
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 15 16  2  0
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 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 16 28  1  0
 21 29  1  0
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 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3085944

   1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

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: 501.03

Molecular Weight (Monoisotopic): 500.1979

AlogP: 4.95

#Rotatable Bonds: 7

Polar Surface Area: 67.23

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.05

CX LogP: 4.13

CX LogD: 4.13

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.39

Np Likeness Score: -1.57

References

1. Sindac JA, Barraza SJ, Dobry CJ, Xiang J, Blakely PK, Irani DN, Keep RF, Miller DJ, Larsen SD..  (2013)  Optimization of novel indole-2-carboxamide inhibitors of neurotropic alphavirus replication.,  56  (22): [PMID:24151954] [10.1021/jm401330r]

2. Barraza SJ, Delekta PC, Sindac JA, Dobry CJ, Xiang J, Keep RF, Miller DJ, Larsen SD..  (2015)  Discovery of anthranilamides as a novel class of inhibitors of neurotropic alphavirus replication.,  23  (7): [PMID:25740634] [10.1016/j.bmc.2015.01.054]

3. Barraza SJ, Sindac JA, Dobry CJ, Delekta PC, Lee PH, Miller DJ, Larsen SD..  (2021)  Synthesis and biological activity of conformationally restricted indole-based inhibitors of neurotropic alphavirus replication: Generation of a three-dimensional pharmacophore.,  46  [PMID:34098081] [10.1016/j.bmcl.2021.128171]

Source

Source(1):

• Scientific Literature