(S)-2-[(S)-2-(2-Hydroxy-acetyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid benzylamide

ID: ALA76578

Chembl Id: CHEMBL76578

Cas Number: 162203-65-8

PubChem CID: 178060

Max Phase: Preclinical

Molecular Formula: C19H25N3O4

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CO)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C19H25N3O4/c23-13-17(24)15-8-4-10-21(15)18(25)16-9-5-11-22(16)19(26)20-12-14-6-2-1-3-7-14/h1-3,6-7,15-16,23H,4-5,8-13H2,(H,20,26)/t15-,16-/m0/s1

Standard InChI Key:  ICULFJDHZQTNRB-HOTGVXAUSA-N

Alternative Forms

1. Parent:

   

   ALA76578

   (S)-N-benzyl-2-((S)-2-(2-hydroxyacetyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxamide

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: 359.43

Molecular Weight (Monoisotopic): 359.1845

AlogP: 0.91

#Rotatable Bonds: 5

Polar Surface Area: 89.95

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.80

CX Basic pKa: ┄

CX LogP: 0.38

CX LogD: 0.38

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -0.72

References

1. Portevin B, Benoist A, Rémond G, Hervé Y, Vincent M, Lepagnol J, De Nanteuil G..  (1996)  New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives.,  39  (12): [PMID:8691432] [10.1021/jm950858c]

2. Jarho EM, Venäläinen JI, Huuskonen J, Christiaans JA, Garcia-Horsman JA, Forsberg MM, Järvinen T, Gynther J, Männistö PT, Wallén EA..  (2004)  A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.,  47  (23): [PMID:15509157] [10.1021/jm049503w]

3. Jarho EM, Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J, Poso A..  (2005)  Dicarboxylic acid azacycle l-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions.,  48  (15): [PMID:16033257] [10.1021/jm0500020]

4. Venäläinen JI, Wallén EA, Poso A, García-Horsman JA, Männistö PT..  (2005)  Synthesis and characterization of the novel fluorescent prolyl oligopeptidase inhibitor 4-fluoresceinthiocarbamoyl-6-aminocaproyl-L-prolyl-2(S)-(hydroxyacetyl)pyrrolidine.,  48  (23): [PMID:16279765] [10.1021/jm0509187]

5. Lawandi J, Gerber-Lemaire S, Juillerat-Jeanneret L, Moitessier N..  (2010)  Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.,  53  (9): [PMID:20058865] [10.1021/jm901104g]

6. Mariaule G, De Cesco S, Airaghi F, Kurian J, Schiavini P, Rocheleau S, Huskić I, Auclair K, Mittermaier A, Moitessier N..  (2016)  3-Oxo-hexahydro-1H-isoindole-4-carboxylic Acid as a Drug Chiral Bicyclic Scaffold: Structure-Based Design and Preparation of Conformationally Constrained Covalent and Noncovalent Prolyl Oligopeptidase Inhibitors.,  59  (9): [PMID:26619267] [10.1021/acs.jmedchem.5b01296]

7. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

8. Plescia J, Hédou D, Pousse ME, Labarre A, Dufresne C, Mittermaier A, Moitessier N..  (2022)  Modulating the selectivity of inhibitors for prolyl oligopeptidase inhibitors and fibroblast activation protein-α for different indications.,  240  [PMID:35797897] [10.1016/j.ejmech.2022.114543]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data