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

ID: ALA562834

Max Phase: Preclinical

Molecular Formula: C24H25ClN2O

Molecular Weight: 392.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(c1ccccc1Cl)C1=C(CC3(CCCC3)CC1=O)N2

Standard InChI:  InChI=1S/C24H25ClN2O/c1-15-8-9-18-19(12-15)27-23(16-6-2-3-7-17(16)25)22-20(26-18)13-24(14-21(22)28)10-4-5-11-24/h2-3,6-9,12,23,26-27H,4-5,10-11,13-14H2,1H3

Standard InChI Key:  QWCJEASGZREXEI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.7033   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504   -6.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140   -5.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151   -5.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8051   -5.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -8.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245   -9.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -9.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256   -9.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1573   -8.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7726   -8.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043   -7.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6394   -5.5557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -7.2103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -6.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2589   -6.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655   -7.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876   -6.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9968   -5.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598   -6.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318   -5.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -5.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564   -5.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -5.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -6.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -5.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498   -8.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -8.5083    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA562834

   ---

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: 392.93

Molecular Weight (Monoisotopic): 392.1655

AlogP: 6.40

#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: 11.80

CX Basic pKa: 2.58

CX LogP: 5.11

CX LogD: 5.11

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -0.67

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