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

ID: ALA1086053

PubChem CID: 46890570

Max Phase: Preclinical

Molecular Formula: C25H30ClNO2

Molecular Weight: 411.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)N2C[C@]3(C)C[C@H]2CC(C)(C)C3)ccc1-c1cc(Cl)ccc1C

Standard InChI:  InChI=1S/C25H30ClNO2/c1-16-6-8-18(26)11-21(16)20-9-7-17(10-22(20)29-5)23(28)27-15-25(4)13-19(27)12-24(2,3)14-25/h6-11,19H,12-15H2,1-5H3/t19-,25-/m1/s1

Standard InChI Key:  ZOMODUIYBKFQKZ-KBMIEXCESA-N

Molfile:  

     RDKit          2D

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    4.1828  -20.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9266  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673  -20.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880  -21.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8474  -21.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4979  -21.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3241  -22.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791  -25.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780  -26.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918  -26.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072  -26.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043  -25.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900  -25.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2874  -24.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984  -23.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9963  -22.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2811  -22.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665  -23.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721  -23.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2774  -21.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622  -21.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810  -19.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619  -20.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917  -20.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6518  -22.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043  -20.0739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8536  -24.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284  -23.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246  -25.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556  -26.7165    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  1  4  1  0
 15 16  1  0
 16 17  2  0
  8  9  2  0
 17 18  1  0
  3  5  1  0
 18 19  2  0
 19 14  1  0
  9 10  1  0
 17 20  1  0
  2  3  1  0
 20 21  2  0
 20  4  1  0
 10 11  2  0
  3 22  1  0
  4  6  1  0
  3 23  1  0
 11 12  1  0
  1 24  1  0
 24  7  1  0
  1  2  1  0
  7 25  1  1
 12 13  2  0
  1 26  1  1
 13  8  1  0
 19 27  1  0
  5  7  1  0
 27 28  1  0
 13 14  1  0
 12 29  1  0
  6  7  1  0
  9 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086053

   [4-(5-chloro-2-methylphenyl)-3-methoxyphenyl]-[(1S,5R)-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: -0.61

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