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

ID: ALA1086481

PubChem CID: 46890956

Max Phase: Preclinical

Molecular Formula: C20H19F3N4

Molecular Weight: 372.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3[nH]c(C(F)(F)F)cc3c2)cn1

Standard InChI:  InChI=1S/C20H19F3N4/c1-26-10-16-8-15(26)11-27(16)19-5-3-13(9-24-19)12-2-4-17-14(6-12)7-18(25-17)20(21,22)23/h2-7,9,15-16,25H,8,10-11H2,1H3/t15-,16-/m0/s1

Standard InChI Key:  NVAIDUCTTKMBKT-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

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   14.3784   -6.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1926   -6.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5983   -6.2691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1926   -5.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3784   -5.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9658   -6.2691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4099   -6.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8166   -6.9774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6297   -6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0416   -6.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6314   -5.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8162   -5.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1516   -6.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3721   -6.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3721   -4.7396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1863   -7.7862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8666   -6.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1025   -5.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2779   -5.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2804   -6.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5195   -6.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1068   -6.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6605   -7.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4156   -7.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3283   -6.4464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1320   -7.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1328   -8.5079    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8475   -7.2672    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8428   -8.0917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
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  1  6  1  0
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 10 17  1  0
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  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
  9 10  2  0
 24 26  1  0
 10 11  1  0
 26 27  1  0
 11 12  2  0
 26 28  1  0
 12  7  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086481

   5-(6-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)-2-(trifluoromethyl)-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: 372.39

Molecular Weight (Monoisotopic): 372.1562

AlogP: 4.14

#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: 3.86

CX LogD: 3.28

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.79

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