(R)-N-(1-cyanocyclopropyl)-3-(1H-indol-3-yl)-2-(((S)-2,2,2-trifluoro-1-phenylethyl)amino)propanamide

ID: ALA4535973

PubChem CID: 155547967

Max Phase: Preclinical

Molecular Formula: C23H21F3N4O

Molecular Weight: 426.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1(NC(=O)[C@@H](Cc2c[nH]c3ccccc23)N[C@@H](c2ccccc2)C(F)(F)F)CC1

Standard InChI:  InChI=1S/C23H21F3N4O/c24-23(25,26)20(15-6-2-1-3-7-15)29-19(21(31)30-22(14-27)10-11-22)12-16-13-28-18-9-5-4-8-17(16)18/h1-9,13,19-20,28-29H,10-12H2,(H,30,31)/t19-,20+/m1/s1

Standard InChI Key:  RNJSOOXYHVOLCF-UXHICEINSA-N

Molfile:  

 
     RDKit          2D

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   14.5026  -24.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4998  -23.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7870  -23.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9234  -23.8134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   18.0532  -23.3968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3460  -24.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4769  -23.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3368  -22.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0864  -22.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6296  -21.8760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4143  -21.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2120  -21.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4594  -20.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9102  -19.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8666  -20.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 18  1  1
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 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535973

   ---

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: 426.44

Molecular Weight (Monoisotopic): 426.1667

AlogP: 4.14

#Rotatable Bonds: 7

Polar Surface Area: 80.71

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.52

CX Basic pKa: 3.53

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -0.71

References

1. Gomes JC, Cianni L, Ribeiro J, Dos Reis Rocho F, da Costa Martins Silva S, Batista PHJ, Moraes CB, Franco CH, Freitas-Junior LHG, Kenny PW, Leitão A, Burtoloso ACB, de Vita D, Montanari CA..  (2019)  Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement.,  27  (22): [PMID:31561938] [10.1016/j.bmc.2019.115083]

Source

Source(1):

• Scientific Literature