rac-(E)-(3-Bromophenyl)(6-methoxy-1-(4-methoxystyryl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

ID: ALA2397274

PubChem CID: 71747288

Max Phase: Preclinical

Molecular Formula: C26H24BrNO3

Molecular Weight: 478.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C2c3ccc(OC)cc3CCN2C(=O)c2cccc(Br)c2)cc1

Standard InChI:  InChI=1S/C26H24BrNO3/c1-30-22-9-6-18(7-10-22)8-13-25-24-12-11-23(31-2)17-19(24)14-15-28(25)26(29)20-4-3-5-21(27)16-20/h3-13,16-17,25H,14-15H2,1-2H3/b13-8+

Standard InChI Key:  QPJMRVWGPFYLOT-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   11.2202  -33.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9354  -34.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6481  -33.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6460  -32.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -32.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2156  -32.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9200  -32.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9189  -33.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6337  -34.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6319  -32.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3472  -32.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3506  -33.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0698  -34.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7900  -33.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7866  -32.8148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0629  -32.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0584  -31.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4998  -32.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4973  -31.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042  -34.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4900  -33.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417  -31.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3371  -30.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0482  -29.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0440  -29.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3268  -28.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6123  -29.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6200  -29.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3211  -27.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0328  -27.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3585  -32.3885    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 18  6  1  0
  8 20  1  0
 20 21  1  0
 17 22  2  0
 22 23  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
 26 29  1  0
 29 30  1  0
  4 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397274

   (3-bromophenyl)-[6-methoxy-1-[(E)-2-(4-methoxyphenyl)ethenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone

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: 478.39

Molecular Weight (Monoisotopic): 477.0940

AlogP: 5.92

#Rotatable Bonds: 5

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.88

CX LogD: 5.88

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -0.37

References

1. Santangelo Freel RM, Ogden KK, Strong KL, Khatri A, Chepiga KM, Jensen HS, Traynelis SF, Liotta DC..  (2013)  Synthesis and structure activity relationship of tetrahydroisoquinoline-based potentiators of GluN2C and GluN2D containing N-methyl-D-aspartate receptors.,  56  (13): [PMID:23627311] [10.1021/jm400177t]

Source

Source(1):

• Scientific Literature