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

ID: ALA4102790

PubChem CID: 137656582

Max Phase: Preclinical

Molecular Formula: C27H28ClNO4

Molecular Weight: 465.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(OCC2c3ccc(OC(C)C)cc3CCN2C(=O)c2cccc(Cl)c2)c1

Standard InChI:  InChI=1S/C27H28ClNO4/c1-18(2)33-24-10-11-25-19(15-24)12-13-29(27(30)20-6-4-7-21(28)14-20)26(25)17-32-23-9-5-8-22(16-23)31-3/h4-11,14-16,18,26H,12-13,17H2,1-3H3

Standard InChI Key:  NPAVEYNCXAFTEH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    8.0591   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0579   -8.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7660   -8.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7642   -6.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4728   -7.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4716   -8.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1778   -8.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8897   -8.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8909   -7.4026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -6.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5996   -6.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3063   -7.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6015   -6.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3027   -8.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0085   -8.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7182   -8.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7176   -7.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0111   -6.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1802   -6.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4725   -5.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4725   -4.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1813   -4.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1817   -3.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4735   -3.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634   -3.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7665   -4.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3499   -8.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6425   -8.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4248   -6.9950    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6431   -7.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9345   -8.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8896   -3.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5971   -3.7248    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
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  2 27  1  0
 27 28  1  0
 17 29  1  0
 28 30  1  0
 28 31  1  0
 23 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102790

   ---

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: 5.95

#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: 5.80

CX LogD: 5.80

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -1.00

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