(1S,4S)-2-methyl-5-(5-phenylpyrazin-2-yl)-2,5-diazabicyclo[2.2.1]heptane

ID: ALA1083617

PubChem CID: 46891589

Max Phase: Preclinical

Molecular Formula: C16H18N4

Molecular Weight: 266.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1cnc(-c2ccccc2)cn1

Standard InChI:  InChI=1S/C16H18N4/c1-19-10-14-7-13(19)11-20(14)16-9-17-15(8-18-16)12-5-3-2-4-6-12/h2-6,8-9,13-14H,7,10-11H2,1H3/t13-,14-/m0/s1

Standard InChI Key:  RKHDYSPQWSSHAH-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -4.4828    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6675    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    2.1259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6675    2.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4828    2.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8959    2.1259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    2.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    1.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    2.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418    2.8315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    2.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4892    1.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4892    3.6574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6740    0.6068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    1.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508    1.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662    2.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    2.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4229    2.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  7  8  2  0
  8  9  1  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
  1  2  1  0
 17 18  2  0
  1  6  1  0
 18 19  1  0
  2  3  1  0
 19 20  2  0
  3  4  1  0
 20 21  1  0
  4  5  1  0
 21 22  2  0
 22 17  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083617

   (1S,4S)-2-methyl-5-(5-phenylpyrazin-2-yl)-2,5-diazabicyclo[2.2.1]heptane

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: 266.35

Molecular Weight (Monoisotopic): 266.1531

AlogP: 2.04

#Rotatable Bonds: 2

Polar Surface Area: 32.26

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.61

CX LogP: 2.13

CX LogD: 1.71

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -0.58

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