(2-chloro-5-methoxy-2'-methylbiphenyl-4-yl)((1R,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl)methanone

ID: ALA1083730

PubChem CID: 46890529

Max Phase: Preclinical

Molecular Formula: C25H30ClNO2

Molecular Weight: 411.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2ccccc2C)c(Cl)cc1C(=O)N1C[C@@]2(C)C[C@@H]1CC(C)(C)C2

Standard InChI:  InChI=1S/C25H30ClNO2/c1-16-8-6-7-9-18(16)19-11-22(29-5)20(10-21(19)26)23(28)27-15-25(4)13-17(27)12-24(2,3)14-25/h6-11,17H,12-15H2,1-5H3/t17-,25-/m0/s1

Standard InChI Key:  UJXPNHJXBUDOGG-GKVSMKOHSA-N

Molfile:  

     RDKit          2D

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    1.6746  -12.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4187  -12.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597  -13.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797  -13.8040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399  -13.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898  -14.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162  -14.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701  -17.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689  -18.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831  -19.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4988  -18.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4960  -17.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7812  -17.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6437  -17.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788  -16.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901  -16.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880  -15.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723  -15.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575  -15.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632  -16.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688  -14.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533  -13.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3735  -12.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9547  -12.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837  -13.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442  -15.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958  -12.5314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675  -15.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6733  -14.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129  -16.6989    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
  1  4  1  0
 15 16  2  0
 16 17  1  0
  8  9  2  0
 17 18  2  0
  3  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
 20 15  1  0
  2  3  1  0
 18 21  1  0
 10 11  2  0
 21 22  2  0
 21  4  1  0
  4  6  1  0
  3 23  1  0
 11 12  1  0
  3 24  1  0
  1  2  1  0
  1 25  1  0
 25  7  1  0
 12 13  2  0
  7 26  1  6
 13  8  1  0
  1 27  1  6
  5  7  1  0
 19 28  1  0
  8 14  1  0
 28 29  1  0
  6  7  1  0
 16 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083730

   [5-chloro-2-methoxy-4-(2-methylphenyl)phenyl]-[(1R,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]methanone

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: 411.97

Molecular Weight (Monoisotopic): 411.1965

AlogP: 6.36

#Rotatable Bonds: 3

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.09

CX LogD: 6.09

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -0.63

References

1. Crombie AL, Antrilli TM, Campbell BA, Crandall DL, Failli AA, He Y, Kern JC, Moore WJ, Nogle LM, Trybulski EJ..  (2010)  Synthesis and evaluation of azabicyclo[3.2.1]octane derivatives as potent mixed vasopressin antagonists.,  20  (12): [PMID:20471258] [10.1016/j.bmcl.2010.04.068]

Source

Source(1):

• Scientific Literature