(R)-3'-(3-methylbenzo[b]thiophen-5-yl)spiro[1-azabicyclo-[2.2.2]octane-3,5'-oxazolidin]-2'-one

ID: ALA2113241

PubChem CID: 71450922

Max Phase: Preclinical

Molecular Formula: C18H20N2O3

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1coc2ccc(N3C[C@@]4(CN5CCC4CC5)OC3=O)cc12

Standard InChI:  InChI=1S/C18H20N2O3/c1-12-9-22-16-3-2-14(8-15(12)16)20-11-18(23-17(20)21)10-19-6-4-13(18)5-7-19/h2-3,8-9,13H,4-7,10-11H2,1H3/t18-/m1/s1

Standard InChI Key:  QENBLMVKRYFDIR-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  1  0  0  0  0  0999 V2000
   -2.1458   -8.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -8.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368   -9.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740   -8.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -9.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8605  -10.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560  -10.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351  -10.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355   -9.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576   -6.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750   -7.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1837   -7.6330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412   -7.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -6.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898   -6.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8062   -5.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142   -6.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2544   -5.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314   -5.3087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3186   -5.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -4.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -7.3319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -9.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 14  1  6
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  1
 10 15  1  0
 10 16  1  0
 15 17  1  0
 15 18  1  0
 16 19  1  0
 17 20  1  0
 18 21  1  0
 19 20  1  0
 19 21  1  0
  4  1  1  0
 13 22  2  0
 12  1  1  0
  5  6  1  0
  9 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2113241

   (5R)-3-(3-methyl-1-benzofuran-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one

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: 312.37

Molecular Weight (Monoisotopic): 312.1474

AlogP: 3.16

#Rotatable Bonds: 1

Polar Surface Area: 45.92

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.68

CX LogP: 2.49

CX LogD: 1.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: 0.41

References

1. Tatsumi R, Fujio M, Takanashi S, Numata A, Katayama J, Satoh H, Shiigi Y, Maeda J, Kuriyama M, Horikawa T, Murozono T, Hashimoto K, Tanaka H..  (2006)  (R)-3'-(3-methylbenzo[b]thiophen-5-yl)spiro[1-azabicyclo[2,2,2]octane-3,5'-oxazolidin]-2'-one, a novel and potent alpha7 nicotinic acetylcholine receptor partial agonist displays cognitive enhancing properties.,  49  (14): [PMID:16821797] [10.1021/jm060249c]

Source

Source(1):

• Scientific Literature