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

ID: ALA563374

Max Phase: Preclinical

Molecular Formula: C25H25F3N2O

Molecular Weight: 426.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1ccccc1C(F)(F)F)C1=C(CC3(CCCC3)CC1=O)N2

Standard InChI:  InChI=1S/C25H25F3N2O/c1-15-8-9-18-19(12-15)30-23(16-6-2-3-7-17(16)25(26,27)28)22-20(29-18)13-24(14-21(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:  DVUIMDDXNVIBOQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   11.3984   -9.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5002   -8.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3103   -8.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7092   -9.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1456   -9.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2513  -11.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4196  -12.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8043  -13.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0207  -12.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8524  -12.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4677  -11.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2994  -10.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3346   -8.8805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4988  -10.5351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9697   -9.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9541  -10.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6606  -10.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828  -10.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6919   -9.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1550   -9.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5270   -9.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0752   -8.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   -8.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8795   -9.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3312   -9.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0558   -9.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6450  -11.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0688  -11.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2852  -11.5750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269  -11.0495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8107  -12.6167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 20 14  1  0
 16 12  1  0
 14 12  1  0
 15 16  2  0
  6  7  2  0
  7  8  1  0
 15 19  1  0
 16 17  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
  8  9  2  0
 20 21  2  0
  1  2  1  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
  2  3  1  0
 23 24  1  0
 10 11  2  0
 24 25  2  0
 25 20  1  0
 11  6  1  0
 24 26  1  0
  3  4  1  0
 17 27  2  0
 11 12  1  0
 10 28  1  0
  4  5  1  0
 28 29  1  0
 21 13  1  0
 28 30  1  0
 13 15  1  0
 28 31  1  0
  5  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA563374

   ---

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: 426.48

Molecular Weight (Monoisotopic): 426.1919

AlogP: 6.77

#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: 11.80

CX Basic pKa: 2.61

CX LogP: 5.39

CX LogD: 5.39

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -0.69

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]

2. 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]

3. 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