2,2,2-trifluoroacetate; 5-(2-azaniumyl-2-{[(1S,2S)-1-cyano-2-phenylcyclopropyl]carbamoyl}ethyl)-1,3-thiazol-3-ium

ID: ALA1162478

PubChem CID: 46905616

Max Phase: Preclinical

Molecular Formula: C18H17F3N4O3S

Molecular Weight: 312.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@]1(NC(=O)C(N)Cc2cncs2)C[C@H]1c1ccccc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C16H16N4OS.C2HF3O2/c17-9-16(7-13(16)11-4-2-1-3-5-11)20-15(21)14(18)6-12-8-19-10-22-12;3-2(4,5)1(6)7/h1-5,8,10,13-14H,6-7,18H2,(H,20,21);(H,6,7)/t13-,14?,16+;/m0./s1

Standard InChI Key:  AJGLLPBWNPILPL-ABULVECESA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.3160  -19.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3160  -20.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0288  -19.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033  -19.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1374  -20.6622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3160  -21.4836    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4945  -20.6622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650  -20.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676  -20.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394  -20.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027  -21.8158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420  -21.0517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002  -19.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904  -20.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120  -20.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320  -19.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099  -21.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740  -21.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710  -22.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040  -22.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4355  -21.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379  -20.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3456  -19.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2041  -19.0439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0974  -20.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397  -20.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4191  -21.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348  -21.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208  -21.7460    0.0000 S   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
 20 21  1  0
 12 14  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  0
  8  9  1  0
 15 17  1  1
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  1  0
 10 12  1  0
 17 18  2  0
 18 19  1  0
 10 13  2  0
 19 20  2  0
  9 10  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: 312.40

Molecular Weight (Monoisotopic): 312.1045

AlogP: 1.58

#Rotatable Bonds: 5

Polar Surface Area: 91.80

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.20

CX Basic pKa: 7.75

CX LogP: 1.01

CX LogD: 0.51

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: -0.24

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