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

ID: ALA1085778

PubChem CID: 46891012

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(-c2cccc3[nH]ccc23)cn1

Standard InChI:  InChI=1S/C19H20N4/c1-22-11-15-9-14(22)12-23(15)19-6-5-13(10-21-19)16-3-2-4-18-17(16)7-8-20-18/h2-8,10,14-15,20H,9,11-12H2,1H3/t14-,15-/m0/s1

Standard InChI Key:  CIUHWQDJGXODPO-GJZGRUSLSA-N

Molfile:  

     RDKit          2D

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   -3.9278  -14.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5220  -14.0627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278  -13.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424  -13.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1552  -14.0627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099  -14.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030  -14.7713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896  -14.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774  -14.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879  -13.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034  -13.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9698  -14.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488  -14.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488  -12.5325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9342  -15.5806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519  -14.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844  -13.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594  -13.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017  -14.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920  -14.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619  -14.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976  -15.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722  -16.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456  -15.5785    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 22  2  0
  1  2  1  0
 20 18  1  0
  1  6  1  0
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 19 17  1  0
 10 17  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  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:

   

   ALA1085778

   4-(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: 7.84

CX LogP: 3.06

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.42

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