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

ID: ALA4085532

PubChem CID: 137646581

Max Phase: Preclinical

Molecular Formula: C27H29ClN2O3

Molecular Weight: 464.99

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H29ClN2O3/c1-18(2)29-22-7-12-25-19(16-22)13-14-30(27(31)20-5-4-6-21(28)15-20)26(25)17-33-24-10-8-23(32-3)9-11-24/h4-12,15-16,18,26,29H,13-14,17H2,1-3H3

Standard InChI Key:  GKQNMTRNRGZQGB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.1305   -2.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1293   -3.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8374   -3.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8356   -2.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5442   -2.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.2493   -3.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9611   -3.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9623   -2.5738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2516   -2.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6710   -2.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3777   -2.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6730   -1.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3741   -3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0800   -3.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7897   -3.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7890   -2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0825   -2.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4963   -2.1661    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.2516   -1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5439   -0.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5439   -0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2528    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2531    1.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5449    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8348    1.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8380    0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4213   -3.8029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5438    2.3324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2510    2.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4207   -4.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7126   -5.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1281   -5.0293    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
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 17 19  1  0
 10 20  1  0
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 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
 25 29  1  0
 29 30  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085532

   ---

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: 464.99

Molecular Weight (Monoisotopic): 464.1867

AlogP: 5.99

#Rotatable Bonds: 7

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.93

CX LogP: 5.43

CX LogD: 5.43

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -1.05

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