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

ID: ALA551917

Max Phase: Preclinical

Molecular Formula: C28H27ClFN3O

Molecular Weight: 476.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1c(F)cccc1Cl)C1=C(CC(c3ccc(N(C)C)cc3)CC1=O)N2

Standard InChI:  InChI=1S/C28H27ClFN3O/c1-16-7-12-22-23(13-16)32-28(26-20(29)5-4-6-21(26)30)27-24(31-22)14-18(15-25(27)34)17-8-10-19(11-9-17)33(2)3/h4-13,18,28,31-32H,14-15H2,1-3H3

Standard InChI Key:  CPBYIULRURBMEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    8.2287   -2.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6854   -5.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5786   -6.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7559   -6.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3980   -5.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8627   -4.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5048   -4.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -2.3987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -4.2060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8356   -2.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0191   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8075   -3.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4123   -3.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4403   -2.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490   -2.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -2.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558   -2.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7723   -3.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770   -3.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -3.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1501   -4.3293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.4288   -4.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -5.5693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8334   -1.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6499   -1.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2546   -0.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0430   -0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2266   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6218   -2.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6477   -0.1941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4642    0.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4361   -0.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3  4  1  0
  1 26  1  0
  6  7  2  0
 26 27  2  0
  7  2  1  0
 27 28  1  0
  2  3  2  0
 28 29  2  0
 11 15  1  0
 29 30  1  0
 12 13  1  0
 30 31  2  0
 31 26  1  0
 13 14  1  0
 29 32  1  0
 14  1  1  0
 32 33  1  0
  1 15  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA551917

   ---

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: 476.00

Molecular Weight (Monoisotopic): 475.1827

AlogP: 6.83

#Rotatable Bonds: 3

Polar Surface Area: 44.37

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.30

CX Basic pKa: 4.91

CX LogP: 5.77

CX LogD: 5.77

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -1.17

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