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

ID: ALA202723

Chembl Id: CHEMBL202723

PubChem CID: 44409450

Max Phase: Preclinical

Molecular Formula: C28H34N4O6

Molecular Weight: 522.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H](NC(=O)O[C@@H]1C(=O)N(C(=O)c2cccnc2)CC1(C)C)C(=O)C(=O)N[C@H](C)c1ccccc1

Standard InChI:  InChI=1S/C28H34N4O6/c1-5-6-14-21(22(33)24(34)30-18(2)19-11-8-7-9-12-19)31-27(37)38-23-26(36)32(17-28(23,3)4)25(35)20-13-10-15-29-16-20/h7-13,15-16,18,21,23H,5-6,14,17H2,1-4H3,(H,30,34)(H,31,37)/t18-,21+,23-/m1/s1

Standard InChI Key:  ONBHKIJPHBOPAS-RZFNWQHOSA-N

Alternative Forms

1. Parent:

   

   ALA202723

   (S)-4,4-dimethyl-1-nicotinoyl-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: 522.60

Molecular Weight (Monoisotopic): 522.2478

AlogP: 3.19

#Rotatable Bonds: 10

Polar Surface Area: 134.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: 3.56

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.36

Np Likeness Score: -0.40

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