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

ID: ALA560655

Max Phase: Preclinical

Molecular Formula: C25H28N2OS

Molecular Weight: 404.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccccc1C1Nc2cc(C)ccc2NC2=C1C(=O)CC1(CCCC1)C2

Standard InChI:  InChI=1S/C25H28N2OS/c1-16-9-10-18-19(13-16)27-24(17-7-3-4-8-22(17)29-2)23-20(26-18)14-25(15-21(23)28)11-5-6-12-25/h3-4,7-10,13,24,26-27H,5-6,11-12,14-15H2,1-2H3

Standard InChI Key:  JAGBDJWFJCMSEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    8.8745   -5.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6216   -6.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1852   -5.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7863   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9763   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7274   -8.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8957   -9.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2804   -9.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4968   -9.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3285   -8.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9438   -8.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755   -7.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8107   -5.3801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9748   -7.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4458   -5.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4301   -6.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1367   -7.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8588   -6.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1680   -5.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -6.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0030   -5.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5513   -4.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276   -4.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -5.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8073   -6.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -5.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1210   -7.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449   -8.3327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3766   -7.5250    0.0000 C   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
  2  3  1  0
  7  8  1  0
  3  4  1  0
  8  9  2  0
  4  5  1  0
 15 19  1  0
 16 17  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
  9 10  1  0
  5  1  1  0
 20 21  2  0
 10 11  2  0
 21 22  1  0
 11  6  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 21 13  1  0
 17 27  2  0
 13 15  1  0
 10 28  1  0
  6  7  2  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA560655

   ---

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: 404.58

Molecular Weight (Monoisotopic): 404.1922

AlogP: 6.47

#Rotatable Bonds: 2

Polar Surface Area: 41.13

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.33

CX Basic pKa: 2.60

CX LogP: 5.14

CX LogD: 5.13

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -0.60

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