(S)-2-((S)-1-(3-chlorophenyl)-2,2,2-trifluoroethylamino)-N-(1-cyanocyclopropyl)-3-phenylpropanamide

ID: ALA4522247

PubChem CID: 155543092

Max Phase: Preclinical

Molecular Formula: C21H19ClF3N3O

Molecular Weight: 421.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1(NC(=O)[C@H](Cc2ccccc2)N[C@@H](c2cccc(Cl)c2)C(F)(F)F)CC1

Standard InChI:  InChI=1S/C21H19ClF3N3O/c22-16-8-4-7-15(12-16)18(21(23,24)25)27-17(11-14-5-2-1-3-6-14)19(29)28-20(13-26)9-10-20/h1-8,12,17-18,27H,9-11H2,(H,28,29)/t17-,18-/m0/s1

Standard InChI Key:  DCAAPPQAAPSMIP-ROUUACIJSA-N

Molfile:  

 
     RDKit          2D

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   33.1458  -13.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7413  -13.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3323  -13.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0815  -13.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0803  -13.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7884  -14.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4980  -13.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4952  -13.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7866  -12.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2014  -12.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9106  -13.0950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6168  -12.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3260  -13.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0322  -12.6784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3291  -13.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4476  -12.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1519  -12.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1983  -11.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9044  -11.4606    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4890  -11.4659    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.1919  -11.0527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.6137  -11.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3198  -11.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0255  -11.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7312  -11.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7286  -10.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0143  -10.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3116  -10.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3736  -12.6955    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14  2  1  0
  2 16  1  0
 16 17  3  0
 10 18  1  1
 18 19  1  0
 18 20  1  0
 18 21  1  0
 12 22  1  1
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522247

   ---

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: 421.85

Molecular Weight (Monoisotopic): 421.1169

AlogP: 4.32

#Rotatable Bonds: 7

Polar Surface Area: 64.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.88

CX Basic pKa: 3.26

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.04

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