rac-4-bromophenyl 6-methyl-3,6-diaza-bicyclo[3.3.1]nonane-3-carboxylate

ID: ALA2062630

PubChem CID: 70682218

Max Phase: Preclinical

Molecular Formula: C15H19BrN2O2

Molecular Weight: 339.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC2CC1CN(C(=O)Oc1ccc(Br)cc1)C2

Standard InChI:  InChI=1S/C15H19BrN2O2/c1-17-7-6-11-8-13(17)10-18(9-11)15(19)20-14-4-2-12(16)3-5-14/h2-5,11,13H,6-10H2,1H3

Standard InChI Key:  RCJSSRZOKUNDDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -3.3808   -9.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2891   -9.8067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546  -10.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797  -11.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6828  -11.3058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900  -10.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3876  -10.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034  -10.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -9.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8447   -9.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572  -11.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1059  -11.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625  -12.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507  -13.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581  -13.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472  -14.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291  -13.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2264  -13.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379  -12.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167  -14.2722    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  4  1  0
  5 11  1  0
  4  5  1  0
 11 12  2  0
  5  6  1  0
 11 13  1  0
  1  6  1  0
 13 14  1  0
  7  8  1  0
 14 15  2  0
  8  3  1  0
 15 16  1  0
  3  9  1  0
 16 17  2  0
  9  1  1  0
 17 18  1  0
  1  2  1  0
 18 19  2  0
 19 14  1  0
  2  7  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062630

   (4-Bromophenyl) 2-methyl-2,7-diazabicyclo[3.3.1]nonane-7-carboxylate

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: 339.23

Molecular Weight (Monoisotopic): 338.0630

AlogP: 2.97

#Rotatable Bonds: 1

Polar Surface Area: 32.78

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.26

CX LogP: 2.84

CX LogD: 1.93

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: -0.68

References

1. Bréthous L, Garcia-Delgado N, Schwartz J, Bertrand S, Bertrand D, Reymond JL..  (2012)  Synthesis and nicotinic receptor activity of chemical space analogues of N-(3R)-1-azabicyclo[2.2.2]oct-3-yl-4-chlorobenzamide (PNU-282,987) and 1,4-diazabicyclo[3.2.2]nonane-4-carboxylic acid 4-bromophenyl ester (SSR180711).,  55  (10): [PMID:22591063] [10.1021/jm300030r]

Source

Source(1):

• Scientific Literature