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

ID: ALA3093944

PubChem CID: 72793722

Max Phase: Preclinical

Molecular Formula: C18H21ClN4O5S

Molecular Weight: 440.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@@H]1CN(S(=O)(=O)c2ccccc2Cl)C[C@H]1C(=O)N1CCOCC1

Standard InChI:  InChI=1S/C18H21ClN4O5S/c19-15-3-1-2-4-16(15)29(26,27)23-11-13(17(24)21-6-5-20)14(12-23)18(25)22-7-9-28-10-8-22/h1-4,13-14H,6-12H2,(H,21,24)/t13-,14-/m1/s1

Standard InChI Key:  PVFKMBIJXLCCRG-ZIAGYGMSSA-N

Molfile:  

     RDKit          2D

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    9.9604  -11.3910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1189  -12.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7339  -11.6545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2240  -10.6174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0044  -10.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0168   -9.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2407   -9.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7546   -9.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6848   -9.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9970   -8.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5508   -7.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1997   -8.3350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9570   -7.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1635   -7.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6065   -7.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8485   -8.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6476   -8.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4265   -9.4300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6110   -8.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0944   -8.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8361   -9.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5771   -9.6432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1587  -11.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6232  -10.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8222  -11.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5580  -11.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1008  -12.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8998  -12.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4384  -12.9349    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA3093944

   (3S,4S)-1-(2-chlorophenyl)sulfonyl-N-(cyanomethyl)-4-(morpholine-4-carbonyl)pyrrolidine-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: 440.91

Molecular Weight (Monoisotopic): 440.0921

AlogP: 0.08

#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: 11.43

CX Basic pKa: ┄

CX LogP: -0.83

CX LogD: -0.83

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -1.97

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