(1S,4S)-2-(5-(benzo[b]thiophen-5-yl)pyridin-2-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane

ID: ALA1085090

PubChem CID: 46890953

Max Phase: Preclinical

Molecular Formula: C19H19N3S

Molecular Weight: 321.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3sccc3c2)cn1

Standard InChI:  InChI=1S/C19H19N3S/c1-21-11-17-9-16(21)12-22(17)19-5-3-15(10-20-19)13-2-4-18-14(8-13)6-7-23-18/h2-8,10,16-17H,9,11-12H2,1H3/t16-,17-/m0/s1

Standard InChI Key:  PBHJNCFSKUFXJI-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   13.7212    1.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5357    1.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9417    1.7106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5357    2.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7212    2.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3083    1.7106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7536    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1606    1.0020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9740    0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3862    1.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9757    2.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1602    2.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4937    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7149    1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7149    3.2409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5294    0.1928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2116    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4480    2.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6230    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6255    0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8653    1.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4523    0.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0063    0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7618    0.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6744    1.5333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  6 13  1  0
  5 14  1  0
  2 14  1  0
  5 15  1  1
  2 16  1  1
 17 20  2  0
  1  2  1  0
 21 18  1  0
  1  6  1  0
 18 19  2  0
 19 17  1  0
 10 17  1  0
 22 20  1  0
  2  3  1  0
 21 22  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085090

   (1S,4S)-2-(5-(benzo[b]thiophen-5-yl)pyridin-2-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane

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: 321.45

Molecular Weight (Monoisotopic): 321.1300

AlogP: 3.86

#Rotatable Bonds: 2

Polar Surface Area: 19.37

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 3.84

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: -1.10

References

1. Li T, Bunnelle WH, Ryther KB, Anderson DJ, Malysz J, Helfrich R, Grønlien JH, Håkerud M, Peters D, Schrimpf MR, Gopalakrishnan M, Ji J..  (2010)  Syntheses and structure-activity relationship (SAR) studies of 2,5-diazabicyclo[2.2.1]heptanes as novel alpha7 neuronal nicotinic receptor (NNR) ligands.,  20  (12): [PMID:20472430] [10.1016/j.bmcl.2010.04.105]

Source

Source(1):

• Scientific Literature