(3S,4S)-N-(cyanomethyl)-4-(morpholine-4-carbonyl)-1-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-3-carboxamide

ID: ALA3093945

PubChem CID: 72793723

Max Phase: Preclinical

Molecular Formula: C19H21F3N4O5S

Molecular Weight: 474.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@@H]1CN(S(=O)(=O)c2ccccc2C(F)(F)F)C[C@H]1C(=O)N1CCOCC1

Standard InChI:  InChI=1S/C19H21F3N4O5S/c20-19(21,22)15-3-1-2-4-16(15)32(29,30)26-11-13(17(27)24-6-5-23)14(12-26)18(28)25-7-9-31-10-8-25/h1-4,13-14H,6-12H2,(H,24,27)/t13-,14-/m1/s1

Standard InChI Key:  WIJLWBKFRDYYLS-ZIAGYGMSSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.4930  -21.8452    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515  -22.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665  -22.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7566  -21.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370  -20.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495  -20.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733  -19.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2873  -20.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2174  -19.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297  -18.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834  -18.3673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323  -18.7893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896  -18.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962  -17.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391  -18.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812  -19.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803  -19.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9591  -19.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436  -18.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6270  -19.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3687  -19.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1098  -20.0975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6913  -22.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559  -21.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549  -21.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906  -22.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335  -22.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325  -22.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731  -23.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7127  -24.1619    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7741  -23.2255    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5494  -23.9627    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  6  9  1  6
  7 10  1  1
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  1  0
  9 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  3  0
  4  1  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3093945

   (3S,4S)-N-(cyanomethyl)-4-(morpholine-4-carbonyl)-1-[2-(trifluoromethyl)phenyl]sulfonylpyrrolidine-3-carboxamide

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: 474.46

Molecular Weight (Monoisotopic): 474.1185

AlogP: 0.44

#Rotatable Bonds: 5

Polar Surface Area: 119.81

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.23

CX Basic pKa: ┄

CX LogP: -0.56

CX LogD: -0.56

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -1.86

References

1. Hilpert H, Mauser H, Humm R, Anselm L, Kuehne H, Hartmann G, Gruener S, Banner DW, Benz J, Gsell B, Kuglstatter A, Stihle M, Thoma R, Sanchez RA, Iding H, Wirz B, Haap W..  (2013)  Identification of potent and selective cathepsin S inhibitors containing different central cyclic scaffolds.,  56  (23): [PMID:24224654] [10.1021/jm401528k]

Source

Source(1):

• Scientific Literature