(1R,2R,4R)-4-(2-Chloro-benzenesulfonyl)-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic Acid Cyanomethyl-amide

ID: ALA3093941

PubChem CID: 49835675

Max Phase: Preclinical

Molecular Formula: C19H22ClN3O5S

Molecular Weight: 439.92

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H22ClN3O5S/c20-16-3-1-2-4-17(16)29(26,27)13-11-14(18(24)22-6-5-21)15(12-13)19(25)23-7-9-28-10-8-23/h1-4,13-15H,6-12H2,(H,22,24)/t13-,14-,15-/m1/s1

Standard InChI Key:  OHLPDKKKTKKBGK-RBSFLKMASA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    5.4122   -6.9707    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5707   -7.7724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1857   -7.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6757   -6.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4561   -5.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4686   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6925   -4.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064   -5.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1366   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488   -4.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0025   -3.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6515   -3.9147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088   -3.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153   -2.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583   -3.5482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003   -4.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0994   -4.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8783   -5.0098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0628   -3.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5462   -4.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2879   -4.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0289   -5.2230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -6.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -6.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -7.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526   -8.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3516   -7.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -8.5106    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  1
  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:

   

   ALA3093941

   (1R,2R,4R)-4-(2-chlorophenyl)sulfonyl-N-(cyanomethyl)-2-(morpholine-4-carbonyl)cyclopentane-1-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: 439.92

Molecular Weight (Monoisotopic): 439.0969

AlogP: 1.01

#Rotatable Bonds: 5

Polar Surface Area: 116.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.48

CX Basic pKa: ┄

CX LogP: -0.10

CX LogD: -0.10

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -1.58

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