rac-(2-(3-(3-chlorophenyl)-1,2,4-oxaqdiazol-5-yl)piperidin-1-yl)(cyclobutyl)methanone

ID: ALA1083034

PubChem CID: 16124095

Max Phase: Preclinical

Molecular Formula: C18H20ClN3O2

Molecular Weight: 345.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(C1CCC1)N1CCCCC1c1nc(-c2cccc(Cl)c2)no1

Standard InChI:  InChI=1S/C18H20ClN3O2/c19-14-8-4-7-13(11-14)16-20-17(24-21-16)15-9-1-2-10-22(15)18(23)12-5-3-6-12/h4,7-8,11-12,15H,1-3,5-6,9-10H2

Standard InChI Key:  INTBVGDNRFKKFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -4.2048   -4.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089   -4.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -5.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -4.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -4.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4907   -3.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9259   -5.3211    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -5.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800   -6.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1723   -6.3226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7609   -5.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -4.9964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0622   -5.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746   -6.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941   -6.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -5.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -4.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733   -4.8973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0593   -4.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659   -4.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -3.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842   -2.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -2.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  8  1  0
  6  1  1  0
 11 13  1  0
 13 14  1  0
  1  2  2  0
  2  7  1  0
  3  4  2  0
  4  8  1  0
  9 10  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 19 21  2  0
 20 22  1  0
  5  6  2  0
  8  9  2  0
 10 11  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083034

   [2-[3-(3-Chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-cyclobutylmethanone

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: 345.83

Molecular Weight (Monoisotopic): 345.1244

AlogP: 4.24

#Rotatable Bonds: 3

Polar Surface Area: 59.23

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: -1.94

References

1. Wágner G, Wéber C, Nyéki O, Nógrádi K, Bielik A, Molnár L, Bobok A, Horváth A, Kiss B, Kolok S, Nagy J, Kurkó D, Gál K, Greiner I, Szombathelyi Z, Keseru GM, Domány G..  (2010)  Hit-to-lead optimization of disubstituted oxadiazoles and tetrazoles as mGluR5 NAMs.,  20  (12): [PMID:20483612] [10.1016/j.bmcl.2010.04.075]

Source

Source(1):

• Scientific Literature