5-(6-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)-1H-indole

ID: ALA1086480

PubChem CID: 46890955

Max Phase: Preclinical

Molecular Formula: C19H20N4

Molecular Weight: 304.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3[nH]ccc3c2)cn1

Standard InChI:  InChI=1S/C19H20N4/c1-22-11-17-9-16(22)12-23(17)19-5-3-15(10-21-19)13-2-4-18-14(8-13)6-7-20-18/h2-8,10,16-17,20H,9,11-12H2,1H3/t16-,17-/m0/s1

Standard InChI Key:  GFMDHQIKVJNHNJ-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    5.0665   -6.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8812   -6.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871   -5.9511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8812   -5.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -5.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -5.9511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0992   -5.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5062   -6.6598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3197   -6.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7318   -5.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3214   -5.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5058   -5.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389   -5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0602   -6.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0602   -4.4208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8748   -7.4693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5574   -5.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7939   -5.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9689   -5.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9714   -6.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2112   -5.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7983   -6.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3524   -7.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1079   -6.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0206   -6.1286    0.0000 N   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:

   

   ALA1086480

   5-(6-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)-1H-indole

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: 304.40

Molecular Weight (Monoisotopic): 304.1688

AlogP: 3.12

#Rotatable Bonds: 2

Polar Surface Area: 35.16

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.85

CX LogP: 3.06

CX LogD: 2.48

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.55

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