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

ID: ALA516292

PubChem CID: 49797573

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+;/m1./s1

Standard InChI Key:  HSOZEOMYHDEMKF-JRTVVOMVSA-N

Molfile:  

     RDKit          2D

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    1.9687  -15.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846  -13.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2528  -13.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937  -15.1661    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687  -15.9911    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437  -15.1661    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831  -16.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615  -16.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4301  -15.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164  -15.1595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631  -15.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526  -15.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241  -15.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466  -15.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139  -16.1262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019  -14.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594  -15.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5552  -16.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9860  -15.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199  -15.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200  -14.2173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808  -17.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529  -17.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540  -18.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577  -19.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2777  -18.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785  -17.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688  -16.6860    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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 18 16  1  0
 19 18  1  0
 20 19  1  0
 18 20  1  0
 18 21  1  1
 21 22  3  0
 19 23  1  6
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 14 29  1  1
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