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

ID: ALA1085091

PubChem CID: 46890954

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]1CN2c1ccc(-c2ccc3[nH]ncc3c2)cn1

Standard InChI:  InChI=1S/C18H19N5/c1-22-10-16-7-15(22)11-23(16)18-5-3-13(8-19-18)12-2-4-17-14(6-12)9-20-21-17/h2-6,8-9,15-16H,7,10-11H2,1H3,(H,20,21)/t15-,16-/m0/s1

Standard InChI Key:  ITIAUUGMGIVTSE-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -4.5842   -6.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7695   -6.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3636   -6.0222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7695   -5.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842   -5.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9971   -6.0222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5515   -6.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -6.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -6.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -6.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293   -5.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -5.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8118   -6.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905   -6.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905   -4.4918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759   -7.5403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932   -6.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1432   -5.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -5.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3208   -6.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -6.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1477   -6.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017   -7.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -7.0223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -6.1996    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:

   

   ALA1085091

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

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: 12.06

CX Basic pKa: 7.84

CX LogP: 2.28

CX LogD: 1.71

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -1.02

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