(6-Ethoxy-1-((4-ethoxyphenoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)(3-fluorophenyl)methanone

ID: ALA4098977

PubChem CID: 137661842

Max Phase: Preclinical

Molecular Formula: C27H28FNO4

Molecular Weight: 449.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(OCC2c3ccc(OCC)cc3CCN2C(=O)c2cccc(F)c2)cc1

Standard InChI:  InChI=1S/C27H28FNO4/c1-3-31-22-8-10-23(11-9-22)33-18-26-25-13-12-24(32-4-2)17-19(25)14-15-29(26)27(30)20-6-5-7-21(28)16-20/h5-13,16-17,26H,3-4,14-15,18H2,1-2H3

Standard InChI Key:  JWAFJDCJYIBUSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   10.3455   -7.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3444   -8.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0524   -8.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0507   -7.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7593   -7.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7581   -8.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4643   -8.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1762   -8.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1774   -7.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4666   -7.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8860   -7.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5928   -7.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8880   -6.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5891   -8.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2950   -8.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0047   -8.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0041   -7.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4666   -6.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7589   -6.0439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7590   -5.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4678   -4.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4682   -4.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7600   -3.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0499   -4.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0530   -4.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6364   -8.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9290   -8.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7589   -2.7781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4661   -2.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210   -8.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7113   -7.2756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4650   -1.5514    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
 24 29  1  0
 29 30  1  0
 28 31  1  0
 17 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098977

   ---

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: 449.52

Molecular Weight (Monoisotopic): 449.2002

AlogP: 5.44

#Rotatable Bonds: 8

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: 5.28

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.95

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