(3-Chlorophenyl)(6-(isopropyl(methyl)amino)-1-((4-methoxyphenoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)-methanone

ID: ALA4103457

PubChem CID: 137657050

Max Phase: Preclinical

Molecular Formula: C28H31ClN2O3

Molecular Weight: 479.02

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H31ClN2O3/c1-19(2)30(3)23-8-13-26-20(17-23)14-15-31(28(32)21-6-5-7-22(29)16-21)27(26)18-34-25-11-9-24(33-4)10-12-25/h5-13,16-17,19,27H,14-15,18H2,1-4H3

Standard InChI Key:  KAMIAEQTOQDAMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.4327   -2.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4316   -3.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1396   -4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1378   -2.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8464   -2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.2634   -3.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2645   -2.8668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5538   -2.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9732   -2.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6799   -2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9752   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6763   -3.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3822   -4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0919   -3.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.3848   -2.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7985   -2.4592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5538   -1.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8461   -1.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8461   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5550   -0.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5554    0.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8471    1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1371    0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1402   -0.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7235   -4.0960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0162   -3.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8461    2.0393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5532    2.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7229   -4.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0149   -5.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4303   -5.3223    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
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  9 11  1  0
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 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
 32 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103457

   ---

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: 479.02

Molecular Weight (Monoisotopic): 478.2023

AlogP: 6.01

#Rotatable Bonds: 7

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: 5.08

CX LogP: 6.07

CX LogD: 6.07

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -1.09

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