(S)-1-((3aS,4R,7aR)-2-Benzyl-3-oxo-2,3,3a,4,5,7a-hexahydro-1H-isoindole-4-carbonyl)pyrrolidine-2-carbonitrile

ID: ALA3817958

PubChem CID: 127050022

Max Phase: Preclinical

Molecular Formula: C21H23N3O2

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@@H]1CCCN1C(=O)[C@@H]1CC=C[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]21

Standard InChI:  InChI=1S/C21H23N3O2/c22-12-17-9-5-11-24(17)20(25)18-10-4-8-16-14-23(21(26)19(16)18)13-15-6-2-1-3-7-15/h1-4,6-8,16-19H,5,9-11,13-14H2/t16-,17-,18+,19-/m0/s1

Standard InChI Key:  RSPHQZYIDJUMKI-OKYOBFRVSA-N

Molfile:  

     RDKit          2D

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   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9909    3.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -1.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035    1.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    3.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    5.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360    5.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    4.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    3.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3505   -1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1107   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -3.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8709   -3.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108   -2.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    6.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5363    7.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  1  4  2  0
  5  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  2 11  1  1
  6 12  1  1
  5 13  1  6
 11 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 16 27  1  6
 27 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3817958

   ---

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: 349.43

Molecular Weight (Monoisotopic): 349.1790

AlogP: 2.35

#Rotatable Bonds: 3

Polar Surface Area: 64.41

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.36

CX LogD: 1.36

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.32

References

1. 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]

2. 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(1):

• Scientific Literature