1-((1R,2R)-1-cyano-2-phenylcyclopropylamino)-3-(3-fluorothiophen-2-yl)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate

ID: ALA515494

PubChem CID: 49797571

Max Phase: Preclinical

Molecular Formula: C19H17F4N3O3S

Molecular Weight: 329.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@@]1(NC(=O)C(N)Cc2sccc2F)C[C@@H]1c1ccccc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C17H16FN3OS.C2HF3O2/c18-13-6-7-23-15(13)8-14(20)16(22)21-17(10-19)9-12(17)11-4-2-1-3-5-11;3-2(4,5)1(6)7/h1-7,12,14H,8-9,20H2,(H,21,22);(H,6,7)/t12-,14?,17+;/m1./s1

Standard InChI Key:  FVCXUKFQJFQVFK-VVARSMMGSA-N

Molfile:  

     RDKit          2D

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    3.0625  -11.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3466  -10.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875  -11.8536    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625  -12.6786    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375  -11.8536    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213  -14.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074  -14.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859  -13.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6282  -13.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914  -14.8485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8014  -13.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2430  -13.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207  -14.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849  -15.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9818  -15.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147  -15.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462  -14.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487  -13.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6567  -12.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152  -12.0770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209  -15.3587    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
  8  9  1  0
 17 19  1  0
 20 19  1  0
 21 20  1  0
 19 21  1  0
 10 13  1  0
 13 14  1  0
 20 22  1  6
  9 10  2  0
 22 23  2  0
 14 15  1  0
 23 24  1  0
 10 11  1  0
 24 25  2  0
 14 16  1  0
 25 26  1  0
 11 12  1  0
 26 27  2  0
 27 22  1  0
 15 17  1  0
 19 28  1  1
 12  8  2  0
 28 29  3  0
 15 18  2  0
  9 30  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: 329.40

Molecular Weight (Monoisotopic): 329.0998

AlogP: 2.32

#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: 11.27

CX Basic pKa: 7.74

CX LogP: 2.28

CX LogD: 1.77

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: -0.54

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