rac-(3-Bromophenyl)(6,7-dimethoxy-1-(4-methoxyphenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanone

ID: ALA2397272

PubChem CID: 71747291

Max Phase: Preclinical

Molecular Formula: C27H28BrNO4

Molecular Weight: 510.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCC2c3cc(OC)c(OC)cc3CCN2C(=O)c2cccc(Br)c2)cc1

Standard InChI:  InChI=1S/C27H28BrNO4/c1-31-22-10-7-18(8-11-22)9-12-24-23-17-26(33-3)25(32-2)16-19(23)13-14-29(24)27(30)20-5-4-6-21(28)15-20/h4-8,10-11,15-17,24H,9,12-14H2,1-3H3

Standard InChI Key:  MTBMVIQPAZQLBZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.8541  -12.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5694  -13.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2821  -12.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2800  -11.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5592  -11.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8495  -11.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5537  -11.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5526  -12.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2674  -13.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2656  -11.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9810  -11.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9844  -12.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7036  -13.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4240  -12.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4206  -11.9835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6968  -11.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1337  -11.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1312  -10.7438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8392  -11.5808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8390  -10.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8378  -13.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1237  -12.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9755  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9710   -9.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6820   -9.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6779   -8.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9606   -7.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2460   -8.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2537   -9.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9550   -7.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666   -6.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9926  -11.5572    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
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  9 12  2  0
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 11 12  1  0
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 12 13  1  0
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 15 18  1  0
 18 19  2  0
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  7 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  1  0
  4 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397272

   (3-bromophenyl)-[6,7-dimethoxy-1-[2-(4-methoxyphenyl)ethyl]-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: 510.43

Molecular Weight (Monoisotopic): 509.1202

AlogP: 5.85

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.85

CX LogD: 5.85

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.35

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