(1S,4S)-2-(6-(benzofuran-5-yl)pyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane

ID: ALA1083301

PubChem CID: 46891527

Max Phase: Preclinical

Molecular Formula: C18H18N4O

Molecular Weight: 306.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3occc3c2)nn1

Standard InChI:  InChI=1S/C18H18N4O/c1-21-10-15-9-14(21)11-22(15)18-5-3-16(19-20-18)12-2-4-17-13(8-12)6-7-23-17/h2-8,14-15H,9-11H2,1H3/t14-,15-/m0/s1

Standard InChI Key:  YAAICMUDFYIZAV-GJZGRUSLSA-N

Molfile:  

     RDKit          2D

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   -4.8886  -17.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741  -17.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681  -16.3561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741  -15.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886  -15.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3015  -16.3561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562  -16.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492  -17.0647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358  -17.0669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236  -16.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341  -15.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496  -15.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235  -16.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8949  -16.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8949  -14.8258    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804  -17.8739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982  -16.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8382  -15.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132  -15.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157  -17.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555  -16.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425  -17.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965  -17.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520  -17.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646  -16.5335    0.0000 O   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:

   

   ALA1083301

   (1S,4S)-2-(6-(benzofuran-5-yl)pyridazin-3-yl)-5-methyl-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: 306.37

Molecular Weight (Monoisotopic): 306.1481

AlogP: 2.78

#Rotatable Bonds: 2

Polar Surface Area: 45.40

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.69

CX LogP: 2.53

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: -0.45

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