(S)-1-((1S,2S)-1-cyano-2-phenylcyclopropylamino)-1-oxo-3-(thiophen-2-yl)propan-2-aminium 2,2,2-trifluoroacetate

ID: ALA478737

PubChem CID: 49797572

Max Phase: Preclinical

Molecular Formula: C19H18F3N3O3S

Molecular Weight: 311.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@]1(NC(=O)[C@H](N)Cc2cccs2)C[C@H]1c1ccccc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C17H17N3OS.C2HF3O2/c18-11-17(10-14(17)12-5-2-1-3-6-12)20-16(21)15(19)9-13-7-4-8-22-13;3-2(4,5)1(6)7/h1-8,14-15H,9-10,19H2,(H,20,21);(H,6,7)/t14-,15+,17+;/m0./s1

Standard InChI Key:  HSOZEOMYHDEMKF-FFMLRVAQSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   16.0139  -18.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0139  -19.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7280  -17.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2996  -17.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8370  -19.0113    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.0139  -19.8344    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.1908  -19.0113    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1830  -18.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0037  -18.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2055  -17.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5017  -17.3929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738  -17.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9724  -17.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6210  -18.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3880  -17.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0408  -18.2282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5023  -16.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8036  -17.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2264  -18.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6304  -17.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6336  -17.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4631  -16.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2828  -19.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5642  -19.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5942  -20.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3216  -21.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0262  -20.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9961  -19.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5068  -18.8465    0.0000 N   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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 18 16  1  1
 19 18  1  0
 20 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  3  0
 19 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 10 13  1  0
 14 29  1  6
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: 311.41

Molecular Weight (Monoisotopic): 311.1092

AlogP: 2.18

#Rotatable Bonds: 5

Polar Surface Area: 78.91

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.63

CX Basic pKa: 7.84

CX LogP: 2.14

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.89

Np Likeness Score: -0.62

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