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

ID: ALA1085089

PubChem CID: 46890952

Max Phase: Preclinical

Molecular Formula: C19H19N3O

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3occc3c2)cn1

Standard InChI:  InChI=1S/C19H19N3O/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:  UYSJVSDAZQUFEH-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    4.2430    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0576    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    1.4642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0576    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2430    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301    1.4642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2754    1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824    0.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4958    0.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9079    1.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4975    2.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6820    2.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2366    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2366    2.9945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -0.0536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7334    1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9697    2.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1447    2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1472    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3870    1.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9741    0.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5282    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2836    0.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1963    1.2868    0.0000 O   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:

   

   ALA1085089

   (1S,4S)-2-(5-(benzofuran-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: 305.38

Molecular Weight (Monoisotopic): 305.1528

AlogP: 3.39

#Rotatable Bonds: 2

Polar Surface Area: 32.51

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.84

CX LogP: 3.12

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: -0.21

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