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

ID: ALA556898

Max Phase: Preclinical

Molecular Formula: C20H18ClFN2O

Molecular Weight: 356.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1c(F)cccc1Cl)C1=C(CCCC1=O)N2

Standard InChI:  InChI=1S/C20H18ClFN2O/c1-11-8-9-14-16(10-11)24-20(18-12(21)4-2-5-13(18)22)19-15(23-14)6-3-7-17(19)25/h2,4-5,8-10,20,23-24H,3,6-7H2,1H3

Standard InChI Key:  FVLQKDWADPKZFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   12.2724    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7291   -0.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0871   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6223   -2.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7996   -2.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4417   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9064   -0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5485    0.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1360    1.9358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7235    0.1286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8793    1.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0628    0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8512    0.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4560    1.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4840    2.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2091    0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3927    1.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7879    2.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9995    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8160    1.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4207    0.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0276    0.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1938    0.0052    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4725   -0.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6190   -1.2347    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  6  7  2  0
  7  2  1  0
  2  3  2  0
 11 15  1  0
 12 13  1  0
 13 14  1  0
 14  1  1  0
  1 15  1  0
  7  8  1  0
  4  5  2  0
 16 17  2  0
 17  9  1  0
 17 18  1  0
  9 11  1  0
 18 19  2  0
 19 20  1  0
 16 10  1  0
 20 21  2  0
 21 16  1  0
 12  8  1  0
 20 22  1  0
 10  8  1  0
  2 23  1  0
 11 12  2  0
 13 24  2  0
  5  6  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA556898

   ---

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: 356.83

Molecular Weight (Monoisotopic): 356.1092

AlogP: 5.37

#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: 2.54

CX LogP: 4.24

CX LogD: 4.24

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -1.34

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