11'-(2-fluoro-6-(trifluoromethyl)phenyl)-8'-methyl-4',5',10',11'-tetrahydrospiro[cyclopentane-1,3'-dibenzo[b,e][1,4]diazepin]-1'(2'H)-one

ID: ALA550567

Max Phase: Preclinical

Molecular Formula: C25H24F4N2O

Molecular Weight: 444.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1c(F)cccc1C(F)(F)F)C1=C(CC3(CCCC3)CC1=O)N2

Standard InChI:  InChI=1S/C25H24F4N2O/c1-14-7-8-17-18(11-14)31-23(21-15(25(27,28)29)5-4-6-16(21)26)22-19(30-17)12-24(13-20(22)32)9-2-3-10-24/h4-8,11,23,30-31H,2-3,9-10,12-13H2,1H3

Standard InChI Key:  DOAKAPZVAOXJFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   12.8562   -7.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9580   -8.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7681   -8.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1670   -7.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6034   -7.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091   -5.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8774   -4.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2621   -3.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4785   -4.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3102   -4.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9255   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7572   -6.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7924   -8.1438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9565   -6.4892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4275   -7.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4119   -6.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1184   -6.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8406   -6.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1497   -8.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6127   -7.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9847   -7.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330   -8.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7093   -8.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3373   -7.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7890   -7.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5136   -7.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3584   -5.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5266   -5.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7430   -5.4493    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.5299   -5.3076    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7847   -5.9748    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685   -4.4077    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  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
 28 29  1  0
 20 14  1  0
  6 30  1  0
 16 12  1  0
 28 31  1  0
 14 12  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA550567

   ---

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: 444.47

Molecular Weight (Monoisotopic): 444.1825

AlogP: 6.91

#Rotatable Bonds: 1

Polar Surface Area: 41.13

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: 2.51

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.77

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