(S)-2-(((R)-1-(3-chlorophenyl)-2,2,2-trifluoroethyl)amino)-N-(1-cyanocyclopropyl)-3-phenylpropanamide

ID: ALA4514540

PubChem CID: 155539200

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-ZWKOTPCHSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.7898  -20.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3853  -20.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9763  -20.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255  -20.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7243  -20.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324  -21.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420  -20.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392  -20.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306  -19.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8454  -19.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5546  -20.1360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2608  -19.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9700  -20.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6762  -19.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9731  -20.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0916  -19.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7959  -19.3008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8423  -18.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5485  -18.5017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330  -18.5070    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8359  -18.0938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2577  -18.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9639  -18.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6695  -18.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3752  -18.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3726  -17.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6584  -17.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9556  -17.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0177  -19.7365    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  6
 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:

   

   ALA4514540

   ---

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