(3-Bromophenyl)(6-(dimethylamino)-1-((4-methoxyphenoxy)-methyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

ID: ALA4088927

PubChem CID: 137641852

Max Phase: Preclinical

Molecular Formula: C26H27BrN2O3

Molecular Weight: 495.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OCC2c3ccc(N(C)C)cc3CCN2C(=O)c2cccc(Br)c2)cc1

Standard InChI:  InChI=1S/C26H27BrN2O3/c1-28(2)21-7-12-24-18(16-21)13-14-29(26(30)19-5-4-6-20(27)15-19)25(24)17-32-23-10-8-22(31-3)9-11-23/h4-12,15-16,25H,13-14,17H2,1-3H3

Standard InChI Key:  UXRCGZMJGFMGKH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    1.8971   -3.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6040   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -3.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3097   -4.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159   -4.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278   -4.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -3.6881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0182   -3.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376   -3.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1443   -3.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396   -2.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1407   -4.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8466   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5563   -4.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556   -3.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8492   -3.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2629   -3.2805    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0182   -2.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105   -2.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0194   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115    0.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015   -0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6046   -0.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -4.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4805   -4.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    1.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    1.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873   -5.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  2 28  1  0
 28 29  1  0
 25 30  1  0
 30 31  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088927

   ---

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: 495.42

Molecular Weight (Monoisotopic): 494.1205

AlogP: 5.34

#Rotatable Bonds: 6

Polar Surface Area: 42.01

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.64

CX LogP: 5.46

CX LogD: 5.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.94

References

1. Strong KL, Epplin MP, Bacsa J, Butch CJ, Burger PB, Menaldino DS, Traynelis SF, Liotta DC..  (2017)  The Structure-Activity Relationship of a Tetrahydroisoquinoline Class of N-Methyl-d-Aspartate Receptor Modulators that Potentiates GluN2B-Containing N-Methyl-d-Aspartate Receptors.,  60  (13): [PMID:28586221] [10.1021/acs.jmedchem.7b00239]

Source

Source(1):

• Scientific Literature