(+)-(1S,4S,5R)-8-(4-Methoxybenzyl)-4-phenyl-6-propyl-6,8-diazabicyclo[3.2.2]nonan-2-one

ID: ALA2021507

PubChem CID: 70691859

Max Phase: Preclinical

Molecular Formula: C24H30N2O2

Molecular Weight: 378.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CC2C(=O)C[C@@H](c3ccccc3)C1CN2Cc1ccc(OC)cc1

Standard InChI:  InChI=1S/C24H30N2O2/c1-3-13-25-17-23-24(27)14-21(19-7-5-4-6-8-19)22(25)16-26(23)15-18-9-11-20(28-2)12-10-18/h4-12,21-23H,3,13-17H2,1-2H3/t21-,22?,23?/m0/s1

Standard InChI Key:  WJGBRVHIHFOHEY-UVKLAMSESA-N

Molfile:  

     RDKit          2D

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   -1.8894    3.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894    2.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    2.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    3.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    4.1087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183    3.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541    2.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685    2.8712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    2.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975    1.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1119    1.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    3.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581    3.4645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    2.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725    3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870    3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1015    3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685    1.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    1.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193    0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5313   -0.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2482    0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2530    1.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409    1.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
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  4  5  2  0
  5  6  1  0
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  7  8  1  0
  5  9  1  0
  9 10  1  0
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 11 18  1  0
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 19 20  1  0
 20 21  1  0
 12 22  2  0
 14 23  1  6
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 23 28  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2021507

   (4S)-8-[(4-methoxyphenyl)methyl]-4-phenyl-6-propyl-6,8-diazabicyclo[3.2.2]nonan-2-one

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: 378.52

Molecular Weight (Monoisotopic): 378.2307

AlogP: 3.72

#Rotatable Bonds: 6

Polar Surface Area: 32.78

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.91

CX LogP: 4.29

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: -0.11

References

1. Holl R, Schepmann D, Fröhlich R, Grünert R, Bednarski PJ, Wünsch B..  (2009)  Dancing of the second aromatic residue around the 6,8-diazabicyclo[3.2.2]nonane framework: influence on sigma receptor affinity and cytotoxicity.,  52  (7): [PMID:19243173] [10.1021/jm801522j]

Source

Source(1):

• Scientific Literature