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

ID: ALA2397271

PubChem CID: 71747290

Max Phase: Preclinical

Molecular Formula: C27H28ClNO4

Molecular Weight: 465.98

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H28ClNO4/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:  OWTMULPDFZKEIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   29.2334  -34.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9487  -34.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6614  -34.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6593  -33.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9385  -32.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2287  -33.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9330  -33.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9318  -34.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6467  -34.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6449  -33.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3602  -33.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3637  -34.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0828  -34.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8032  -34.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7998  -33.4087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0760  -32.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0715  -32.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5130  -32.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5104  -32.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2184  -33.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2182  -32.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2171  -34.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5029  -34.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3547  -31.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3502  -30.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0613  -30.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0571  -29.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3398  -29.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6253  -29.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6330  -30.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3342  -28.4621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0459  -28.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3719  -32.9823    0.0000 Cl  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
  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:

   

   ALA2397271

   (3-chlorophenyl)-[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: 465.98

Molecular Weight (Monoisotopic): 465.1707

AlogP: 5.74

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.68

CX LogD: 5.68

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -0.43

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