(S)-benzyl 3-(((S)-1,2-dioxo-1-((R)-1-phenylethylamino)heptan-3-yl)carbamoyloxy)-4,4-dimethyl-2-oxopyrrolidine-1-carboxylate

ID: ALA383238

Chembl Id: CHEMBL383238

PubChem CID: 44409368

Max Phase: Preclinical

Molecular Formula: C30H37N3O7

Molecular Weight: 551.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H](NC(=O)O[C@@H]1C(=O)N(C(=O)OCc2ccccc2)CC1(C)C)C(=O)C(=O)N[C@H](C)c1ccccc1

Standard InChI:  InChI=1S/C30H37N3O7/c1-5-6-17-23(24(34)26(35)31-20(2)22-15-11-8-12-16-22)32-28(37)40-25-27(36)33(19-30(25,3)4)29(38)39-18-21-13-9-7-10-14-21/h7-16,20,23,25H,5-6,17-19H2,1-4H3,(H,31,35)(H,32,37)/t20-,23+,25-/m1/s1

Standard InChI Key:  WPXHFEMBMPUNEA-JHMXWDHMSA-N

Alternative Forms

1. Parent:

   

   ALA383238

   (S)-benzyl 3-(((S)-1,2-dioxo-1-((R)-1-phenylethylamino)heptan-3-yl)carbamoyloxy)-4,4-dimethyl-2-oxopyrrolidine-1-carboxylate

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: 551.64

Molecular Weight (Monoisotopic): 551.2632

AlogP: 4.29

#Rotatable Bonds: 11

Polar Surface Area: 131.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.24

CX Basic pKa: ┄

CX LogP: 5.42

CX LogD: 5.42

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.40

Np Likeness Score: -0.14

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