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

ID: ALA562770

Max Phase: Preclinical

Molecular Formula: C24H20ClFN2O2

Molecular Weight: 422.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1c(F)cccc1Cl)C1=C(CC(c3ccco3)CC1=O)N2

Standard InChI:  InChI=1S/C24H20ClFN2O2/c1-13-7-8-17-18(10-13)28-24(22-15(25)4-2-5-16(22)26)23-19(27-17)11-14(12-20(23)29)21-6-3-9-30-21/h2-10,14,24,27-28H,11-12H2,1H3

Standard InChI Key:  GNGGHMGWVRDRIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    4.6079   -2.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -4.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226   -5.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -6.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1351   -6.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772   -5.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419   -4.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840   -3.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -2.0406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590   -3.8479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -3.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8195   -1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -3.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3350   -2.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562   -3.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -3.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293   -3.9712    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080   -3.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -5.2112    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -1.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0221   -1.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4239   -0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8627   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3  4  1  0
  1 26  1  0
 29 30  1  0
  6  7  2  0
 27 28  1  0
  7  2  1  0
  2  3  2  0
 11 15  1  0
 26 27  1  0
 28 29  2  0
 30 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA562770

   ---

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: 422.89

Molecular Weight (Monoisotopic): 422.1197

AlogP: 6.36

#Rotatable Bonds: 2

Polar Surface Area: 54.27

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: 2.54

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.25

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