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

ID: ALA1085599

PubChem CID: 46890894

Max Phase: Preclinical

Molecular Formula: C18H19N5

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ncc(-c2cccc3[nH]ccc23)cn1

Standard InChI:  InChI=1S/C18H19N5/c1-22-10-14-7-13(22)11-23(14)18-20-8-12(9-21-18)15-3-2-4-17-16(15)5-6-19-17/h2-6,8-9,13-14,19H,7,10-11H2,1H3/t13-,14-/m0/s1

Standard InChI Key:  HKBXSDZHLWXIDN-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -4.8487  -26.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345  -26.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288  -25.4920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345  -24.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8487  -24.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613  -25.4920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172  -25.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105  -26.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974  -26.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854  -25.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957  -24.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109  -24.7873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0829  -25.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8550  -25.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8550  -23.9624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408  -27.0091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604  -25.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8754  -24.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508  -24.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925  -25.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8830  -26.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533  -26.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061  -27.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634  -27.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363  -27.0070    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
 18 19  2  0
 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:

   

   ALA1085599

   4-(2-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyrimidin-5-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: 305.38

Molecular Weight (Monoisotopic): 305.1640

AlogP: 2.52

#Rotatable Bonds: 2

Polar Surface Area: 48.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.56

CX LogP: 2.44

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.21

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