(S)-N-(1-cyanocyclopropyl)-4-methyl-2-(((S)-2,2,2-trifluoro-1-phenylethyl)amino)pentanamide

ID: ALA4519995

PubChem CID: 67298247

Max Phase: Preclinical

Molecular Formula: C18H22F3N3O

Molecular Weight: 353.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](N[C@@H](c1ccccc1)C(F)(F)F)C(=O)NC1(C#N)CC1

Standard InChI:  InChI=1S/C18H22F3N3O/c1-12(2)10-14(16(25)24-17(11-22)8-9-17)23-15(18(19,20)21)13-6-4-3-5-7-13/h3-7,12,14-15,23H,8-10H2,1-2H3,(H,24,25)/t14-,15-/m0/s1

Standard InChI Key:  UXYWRPKODJHGIP-GJZGRUSLSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   18.2382   -5.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8338   -4.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4248   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1739   -4.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1728   -5.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8808   -5.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5905   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5876   -4.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8790   -4.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2938   -4.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0030   -4.4649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7092   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4185   -4.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1246   -4.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4215   -5.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5400   -4.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2443   -3.6297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2907   -3.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9969   -2.8306    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5815   -2.8359    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2843   -2.4227    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7061   -3.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4123   -2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1215   -3.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4092   -2.0081    0.0000 C   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  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519995

   (2S)-N-(1-cyanocyclopropyl)-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-phenylethyl]amino]pentanamide

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: 353.39

Molecular Weight (Monoisotopic): 353.1715

AlogP: 3.47

#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: 11.39

CX Basic pKa: 3.52

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.82

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