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

ID: ALA1085824

PubChem CID: 46890895

Max Phase: Preclinical

Molecular Formula: C17H19N3

Molecular Weight: 265.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccccc2)cn1

Standard InChI:  InChI=1S/C17H19N3/c1-19-11-16-9-15(19)12-20(16)17-8-7-14(10-18-17)13-5-3-2-4-6-13/h2-8,10,15-16H,9,11-12H2,1H3/t15-,16-/m0/s1

Standard InChI Key:  FSBKKFGQSCIUHX-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -4.6997    0.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    0.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4774    1.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    2.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6997    2.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1133    1.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640    1.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2564    0.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290    1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401    2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2568    2.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9291    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    1.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    2.9825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8903   -0.0705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2107    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0384    0.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    2.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099    2.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  7  8  2  0
  8  9  1  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
  1  2  1  0
 17 18  2  0
  1  6  1  0
 18 19  1  0
  2  3  1  0
 19 20  2  0
  3  4  1  0
 20 21  1  0
  4  5  1  0
 21 22  2  0
 22 17  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085824

   (1S,4S)-2-methyl-5-(5-phenylpyridin-2-yl)-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: 265.36

Molecular Weight (Monoisotopic): 265.1579

AlogP: 2.64

#Rotatable Bonds: 2

Polar Surface Area: 19.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 2.96

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -0.64

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