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

ID: ALA1085779

PubChem CID: 46891013

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(-c2ccc3cc[nH]c3c2)cn1

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

Standard InChI Key:  JHVKOOCZASOHSP-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    5.3673  -15.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1820  -15.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5879  -14.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1820  -13.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673  -13.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9544  -14.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000  -14.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8070  -15.0405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6205  -15.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0326  -14.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6222  -13.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8066  -13.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1397  -14.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610  -14.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610  -12.8014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1756  -15.8499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8582  -14.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2697  -13.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2722  -15.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0992  -15.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0947  -13.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5146  -14.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3241  -14.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4046  -13.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6449  -12.9987    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 19  2  0
  1  2  1  0
 21 18  2  0
 18 17  1  0
 10 17  1  0
 20 19  1  0
  1  6  1  0
 22 20  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:

   

   ALA1085779

   6-(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: 2.48

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.51

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