(S)-1-(benzylsulfonyl)-4,4-dimethyl-2-oxopyrrolidin-3-yl (S)-1,2-dioxo-1-((R)-1-phenylethylamino)heptan-3-ylcarbamate

ID: ALA203027

Chembl Id: CHEMBL203027

PubChem CID: 44409364

Max Phase: Preclinical

Molecular Formula: C29H37N3O7S

Molecular Weight: 571.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H](NC(=O)O[C@@H]1C(=O)N(S(=O)(=O)Cc2ccccc2)CC1(C)C)C(=O)C(=O)N[C@H](C)c1ccccc1

Standard InChI:  InChI=1S/C29H37N3O7S/c1-5-6-17-23(24(33)26(34)30-20(2)22-15-11-8-12-16-22)31-28(36)39-25-27(35)32(19-29(25,3)4)40(37,38)18-21-13-9-7-10-14-21/h7-16,20,23,25H,5-6,17-19H2,1-4H3,(H,30,34)(H,31,36)/t20-,23+,25-/m1/s1

Standard InChI Key:  MQBPRNSYVDZDCX-JHMXWDHMSA-N

Alternative Forms

1. Parent:

   

   ALA203027

   (S)-1-(benzylsulfonyl)-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: 571.70

Molecular Weight (Monoisotopic): 571.2352

AlogP: 3.48

#Rotatable Bonds: 12

Polar Surface Area: 138.95

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.07

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.37

Np Likeness Score: -0.39

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