(S)-1-(benzo[b]thiophene-2-carbonyl)-4,4-dimethyl-2-oxopyrrolidin-3-yl (S)-1,2-dioxo-1-((R)-1-phenylethylamino)heptan-3-ylcarbamate

ID: ALA202685

Chembl Id: CHEMBL202685

PubChem CID: 44409380

Max Phase: Preclinical

Molecular Formula: C31H35N3O6S

Molecular Weight: 577.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H](NC(=O)O[C@@H]1C(=O)N(C(=O)c2cc3ccccc3s2)CC1(C)C)C(=O)C(=O)N[C@H](C)c1ccccc1

Standard InChI:  InChI=1S/C31H35N3O6S/c1-5-6-15-22(25(35)27(36)32-19(2)20-12-8-7-9-13-20)33-30(39)40-26-29(38)34(18-31(26,3)4)28(37)24-17-21-14-10-11-16-23(21)41-24/h7-14,16-17,19,22,26H,5-6,15,18H2,1-4H3,(H,32,36)(H,33,39)/t19-,22+,26-/m1/s1

Standard InChI Key:  LQWTXKBZZYLTSL-BORKOYIJSA-N

Alternative Forms

1. Parent:

   

   ALA202685

   (S)-1-(benzo[b]thiophene-2-carbonyl)-4,4-dimethyl-2-oxopyrrolidin-3-yl (S)-1,2-dioxo-1-((R)-1-phenylethylamino)heptan-3-ylcarbamate

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: 577.70

Molecular Weight (Monoisotopic): 577.2247

AlogP: 5.01

#Rotatable Bonds: 10

Polar Surface Area: 121.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.23

CX Basic pKa: ┄

CX LogP: 5.94

CX LogD: 5.94

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.26

Np Likeness Score: -0.54

References

1. Barrett DG, Catalano JG, Deaton DN, Hassell AM, Long ST, Miller AB, Miller LR, Ray JA, Samano V, Shewchuk LM, Wells-Knecht KJ, Willard DH, Wright LL..  (2006)  Novel, potent P2-P3 pyrrolidine derivatives of ketoamide-based cathepsin K inhibitors.,  16  (6): [PMID:16376075] [10.1016/j.bmcl.2005.11.101]

Source

Source(1):

• Scientific Literature