tert-Butyl(S)-1-((S)-2-((R,S)-1-(diphenoxyphosphoryl)butylcarbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

ID: ALA2163503

Chembl Id: CHEMBL2163503

PubChem CID: 60195210

Max Phase: Preclinical

Molecular Formula: C31H44N3O7P

Molecular Weight: 601.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)P(=O)(Oc1ccccc1)Oc1ccccc1

Standard InChI:  InChI=1S/C31H44N3O7P/c1-7-15-26(42(38,40-23-16-10-8-11-17-23)41-24-18-12-9-13-19-24)32-28(35)25-20-14-21-34(25)29(36)27(22(2)3)33-30(37)39-31(4,5)6/h8-13,16-19,22,25-27H,7,14-15,20-21H2,1-6H3,(H,32,35)(H,33,37)/t25-,26?,27-/m0/s1

Standard InChI Key:  CNDRFBYUKZJJLP-LLOGBAKRSA-N

Alternative Forms

1. Parent:

   

   ALA2163503

   tert-butyl N-[(2S)-1-[(2S)-2-(1-diphenoxyphosphorylbutylcarbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

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: 601.68

Molecular Weight (Monoisotopic): 601.2917

AlogP: 6.12

#Rotatable Bonds: 12

Polar Surface Area: 123.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.77

CX Basic pKa: ┄

CX LogP: 5.33

CX LogD: 5.33

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.28

Np Likeness Score: -0.44

References

1. Winiarski Ł, Oleksyszyn J, Sieńczyk M..  (2012)  Human neutrophil elastase phosphonic inhibitors with improved potency of action.,  55  (14): [PMID:22720718] [10.1021/jm300599x]

2. Agbowuro AA, Hwang J, Peel E, Mazraani R, Springwald A, Marsh JW, McCaughey L, Gamble AB, Huston WM, Tyndall JDA..  (2019)  Structure-activity analysis of peptidic Chlamydia HtrA inhibitors.,  27  (18): [PMID:31395511] [10.1016/j.bmc.2019.07.049]

Source

Source(1):

• Scientific Literature