11-(2-chloro-6-fluorophenyl)-3,3,8-trimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one

ID: ALA552189

Max Phase: Preclinical

Molecular Formula: C22H22ClFN2O

Molecular Weight: 384.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1c(F)cccc1Cl)C1=C(CC(C)(C)CC1=O)N2

Standard InChI:  InChI=1S/C22H22ClFN2O/c1-12-7-8-15-16(9-12)26-21(19-13(23)5-4-6-14(19)24)20-17(25-15)10-22(2,3)11-18(20)27/h4-9,21,25-26H,10-11H2,1-3H3

Standard InChI Key:  RHZHUVHAOMPSGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -0.1493   -0.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561   -2.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788   -1.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4367   -1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -0.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424    1.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    0.1738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    1.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155    0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0272    0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940    1.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3944    2.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857    1.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905    2.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788    1.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4577    0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959   -0.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914    2.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645    2.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -0.3528    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594   -1.1895    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8508    0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  6  7  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3  4  2  0
 17  8  1  0
 16 17  2  0
  8 10  1  0
 17 18  1  0
 18 19  2  0
 16  9  1  0
 19 20  1  0
 11  7  1  0
 20 21  2  0
 21 16  1  0
  9  7  1  0
 12 22  2  0
 10 11  2  0
 14 23  1  0
  4  5  1  0
 14 24  1  0
  2  3  1  0
  1 25  1  0
  5  6  2  0
  5 26  1  0
  6  1  1  0
 20 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA552189

   ---

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: 384.88

Molecular Weight (Monoisotopic): 384.1405

AlogP: 6.01

#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: 11.31

CX Basic pKa: 2.52

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.16

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