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

ID: ALA4100185

PubChem CID: 137660265

Max Phase: Preclinical

Molecular Formula: C28H29ClFNO4

Molecular Weight: 497.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(OCC2c3ccc(OC(C)C)cc3CCN2C(=O)c2ccc(F)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C28H29ClFNO4/c1-4-33-21-6-8-22(9-7-21)34-17-27-24-11-10-23(35-18(2)3)15-19(24)13-14-31(27)28(32)20-5-12-26(30)25(29)16-20/h5-12,15-16,18,27H,4,13-14,17H2,1-3H3

Standard InChI Key:  OPGSIFXARDWEQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   38.1713  -21.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1702  -21.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8782  -22.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8764  -20.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5851  -21.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5839  -21.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2901  -22.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0020  -21.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0031  -21.0101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2924  -20.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7118  -20.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4185  -21.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7138  -19.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4149  -21.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1208  -22.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8305  -21.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8298  -21.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1234  -20.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2924  -19.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5847  -19.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5847  -18.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2936  -18.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2940  -17.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5857  -16.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8757  -17.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8788  -18.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4621  -22.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7548  -21.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5847  -16.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2918  -15.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0467  -22.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7554  -21.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2908  -14.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5377  -22.2426    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   44.5371  -20.6025    0.0000 Cl  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
 28 32  1  0
 30 33  1  0
 16 34  1  0
 17 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100185

   ---

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: 497.99

Molecular Weight (Monoisotopic): 497.1769

AlogP: 6.48

#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: 6.30

CX LogD: 6.30

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: -1.24

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