Trifluoro-acetate(S)-1-((1S,2S)-1-cyano-2-phenyl-cyclopropylcarbamoyl)-2-(2-fluoro-phenyl)-ethyl-ammonium

ID: ALA1162477

PubChem CID: 46905615

Max Phase: Preclinical

Molecular Formula: C21H19F4N3O3

Molecular Weight: 323.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@]1(NC(=O)[C@@H](N)Cc2ccccc2F)C[C@H]1c1ccccc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C19H18FN3O.C2HF3O2/c20-16-9-5-4-8-14(16)10-17(22)18(24)23-19(12-21)11-15(19)13-6-2-1-3-7-13;3-2(4,5)1(6)7/h1-9,15,17H,10-11,22H2,(H,23,24);(H,6,7)/t15-,17-,19+;/m0./s1

Standard InChI Key:  ACLOSPXSOURJGD-UEXRLZNCSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   16.5734  -12.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5734  -13.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2860  -12.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8607  -12.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3947  -13.6494    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5734  -14.4707    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7521  -13.6494    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0841  -13.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7814  -13.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5137  -13.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7463  -14.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2068  -13.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5487  -12.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9391  -13.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7606  -13.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3807  -12.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4584  -14.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4226  -14.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1195  -15.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8524  -14.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8839  -14.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1864  -13.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7944  -12.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6529  -11.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3518  -13.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6564  -13.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9245  -13.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8890  -14.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5912  -15.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3202  -14.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6938  -12.5983    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  2  5  1  0
  2  6  1  0
  2  7  1  0
 21 22  2  0
 22 17  1  0
 15 14  1  0
 14 23  1  6
 16 15  1  0
 23 24  3  0
 14 16  1  0
  8 25  1  0
 25 26  2  0
  9 11  1  1
 26 27  1  0
  8  9  1  0
 27 28  2  0
 15 17  1  1
 28 29  1  0
 10 12  1  0
 29 30  2  0
 30 25  1  0
 17 18  2  0
 26 31  1  0
 18 19  1  0
 10 13  2  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
 12 14  1  0
M  END

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: 323.37

Molecular Weight (Monoisotopic): 323.1434

AlogP: 2.26

#Rotatable Bonds: 5

Polar Surface Area: 78.91

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.48

CX Basic pKa: 7.89

CX LogP: 2.37

CX LogD: 1.75

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: -0.37

References

1. Méthot N, Rubin J, Guay D, Beaulieu C, Ethier D, Reddy TJ, Riendeau D, Percival MD..  (2007)  Inhibition of the activation of multiple serine proteases with a cathepsin C inhibitor requires sustained exposure to prevent pro-enzyme processing.,  282  (29): [PMID:17535802] [10.1074/jbc.m702615200]

Source

Source(1):

• Scientific Literature