(S)-N-(2-(2-cyanopiperidin-1-yl)-2-oxoethyl)benzamide

ID: ALA2022534

PubChem CID: 70689752

Max Phase: Preclinical

Molecular Formula: C15H17N3O2

Molecular Weight: 271.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@@H]1CCCCN1C(=O)CNC(=O)c1ccccc1

Standard InChI:  InChI=1S/C15H17N3O2/c16-10-13-8-4-5-9-18(13)14(19)11-17-15(20)12-6-2-1-3-7-12/h1-3,6-7,13H,4-5,8-9,11H2,(H,17,20)/t13-/m0/s1

Standard InChI Key:  OTFXIFLLRODAGY-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   22.8570  -14.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4295  -14.9089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1453  -15.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8570  -14.0839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5729  -15.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7136  -15.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9978  -14.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5702  -14.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2861  -13.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9978  -14.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7136  -16.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2886  -15.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5702  -14.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5744  -13.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5763  -12.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8637  -12.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1474  -12.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1438  -13.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2871  -14.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9958  -14.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  7 10  2  0
  6 11  2  0
  2  6  1  0
  2  3  1  0
 12 13  2  0
  4 14  1  0
  1  3  1  0
  1  4  1  0
  1  5  2  0
  6  7  1  0
  7 12  1  0
  4 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13  8  1  0
 14 19  1  1
  8  9  2  0
 19 20  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA2022534

   N-[2-[(2S)-2-cyanopiperidin-1-yl]-2-oxoethyl]benzamide

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: 271.32

Molecular Weight (Monoisotopic): 271.1321

AlogP: 1.32

#Rotatable Bonds: 3

Polar Surface Area: 73.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.76

CX LogD: 0.76

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.90

Np Likeness Score: -1.18

References

1. Ryabtsova O, Jansen K, Van Goethem S, Joossens J, Cheng JD, Lambeir AM, De Meester I, Augustyns K, Van der Veken P..  (2012)  Acylated Gly-(2-cyano)pyrrolidines as inhibitors of fibroblast activation protein (FAP) and the issue of FAP/prolyl oligopeptidase (PREP)-selectivity.,  22  (10): [PMID:22525314] [10.1016/j.bmcl.2012.03.107]

Source

Source(1):

• Scientific Literature