2-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

ID: ALA477206

PubChem CID: 25256816

Max Phase: Preclinical

Molecular Formula: C25H33N3O2

Molecular Weight: 407.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(CCCCN2CCCc3ccccc3C2=O)CC1

Standard InChI:  InChI=1S/C25H33N3O2/c1-30-24-13-5-4-12-23(24)27-19-17-26(18-20-27)14-6-7-15-28-16-8-10-21-9-2-3-11-22(21)25(28)29/h2-5,9,11-13H,6-8,10,14-20H2,1H3

Standard InChI Key:  USGFBEWNXKQBDG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.4433  -26.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2115  -27.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9612  -25.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8548  -26.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7178  -25.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3008  -25.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5690  -27.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1114  -25.3314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3364  -26.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5772  -26.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0004  -24.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3461  -24.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7608  -23.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5852  -23.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9975  -23.1851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8176  -23.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2252  -22.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8026  -21.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9725  -21.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5756  -22.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2038  -21.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0229  -21.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4317  -20.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0072  -19.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1733  -19.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7636  -20.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9394  -20.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5140  -19.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  1  2  2  0
 16 17  1  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  7  9  1  0
  8 10  1  0
  9 11  1  0
 10 11  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 20 23  1  0
  7 12  2  0
 28 29  1  0
  9 13  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA477206

   2-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

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: 407.56

Molecular Weight (Monoisotopic): 407.2573

AlogP: 3.69

#Rotatable Bonds: 7

Polar Surface Area: 36.02

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.87

CX LogP: 3.93

CX LogD: 3.34

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.05

References

1. Ortega R, Raviña E, Masaguer CF, Areias F, Brea J, Loza MI, López L, Selent J, Pastor M, Sanz F..  (2009)  Synthesis, binding affinity and SAR of new benzolactam derivatives as dopamine D3 receptor ligands.,  19  (6): [PMID:19217777] [10.1016/j.bmcl.2009.01.067]

2. Ortega R, Hübner H, Gmeiner P, Masaguer CF..  (2011)  Aromatic ring functionalization of benzolactam derivatives: new potent dopamine D3 receptor ligands.,  21  (9): [PMID:21273071] [10.1016/j.bmcl.2010.12.083]

Source

Source(1):

• Scientific Literature