8'-methyl-11'-(2-(trifluoromethylthio)phenyl)-4',5',10',11'-tetrahydrospiro[cyclopentane-1,3'-dibenzo[b,e][1,4]diazepin]-1'(2'H)-one

ID: ALA557707

Max Phase: Preclinical

Molecular Formula: C25H25F3N2OS

Molecular Weight: 458.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1ccccc1SC(F)(F)F)C1=C(CC3(CCCC3)CC1=O)N2

Standard InChI:  InChI=1S/C25H25F3N2OS/c1-15-8-9-17-18(12-15)30-23(16-6-2-3-7-21(16)32-25(26,27)28)22-19(29-17)13-24(14-20(22)31)10-4-5-11-24/h2-3,6-9,12,23,29-30H,4-5,10-11,13-14H2,1H3

Standard InChI Key:  RJHHBWPHDDZAHU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    3.9725   -1.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7196   -1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832   -1.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843   -0.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0742   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -3.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936   -4.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783   -5.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5947   -5.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265   -4.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -3.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735   -2.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9086   -1.0121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281   -2.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   -2.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9568   -2.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659   -1.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -1.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -0.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1745   -0.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947   -1.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429   -3.9646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -4.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877   -5.0638    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -5.1295    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5220   -3.8989    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  2  0
  4  5  1  0
 15 19  1  0
 16 17  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
  9 10  1  0
  5  1  1  0
 20 21  2  0
 10 11  2  0
 21 22  1  0
 11  6  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 21 13  1  0
 17 27  2  0
 13 15  1  0
 10 28  1  0
  6  7  2  0
 20 14  1  0
 28 29  1  0
 16 12  1  0
 29 30  1  0
 14 12  1  0
 29 31  1  0
 15 16  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA557707

   ---

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: 458.55

Molecular Weight (Monoisotopic): 458.1640

AlogP: 7.36

#Rotatable Bonds: 2

Polar Surface Area: 41.13

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.25

CX Basic pKa: 2.60

CX LogP: 6.48

CX LogD: 6.47

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.75

References

1. Fu J, Shuttleworth SJ, Connors RV, Chai A, Coward P..  (2009)  Discovery and optimization of a novel Neuromedin B receptor antagonist.,  19  (15): [PMID:19553112] [10.1016/j.bmcl.2009.05.124]

Source

Source(1):

• Scientific Literature