(R)-(3-chlorophenyl)(6-isopropoxy-1-((4-methoxyphenoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanethione

ID: ALA4101985

PubChem CID: 137661532

Max Phase: Preclinical

Molecular Formula: C27H28ClNO3S

Molecular Weight: 482.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC[C@H]2c3ccc(OC(C)C)cc3CCN2C(=S)c2cccc(Cl)c2)cc1

Standard InChI:  InChI=1S/C27H28ClNO3S/c1-18(2)32-24-11-12-25-19(16-24)13-14-29(27(33)20-5-4-6-21(28)15-20)26(25)17-31-23-9-7-22(30-3)8-10-23/h4-12,15-16,18,26H,13-14,17H2,1-3H3/t26-/m0/s1

Standard InChI Key:  UDKWTIUVZOIYNA-SANMLTNESA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.3174   -7.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3162   -8.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0243   -8.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0225   -6.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7311   -7.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7299   -8.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4361   -8.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1480   -8.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1492   -7.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4385   -6.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8579   -6.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5646   -7.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8598   -6.0960    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5610   -8.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2669   -8.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9765   -8.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9759   -7.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2694   -6.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4385   -6.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7308   -5.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7308   -4.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4397   -4.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7318   -3.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0217   -3.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0249   -4.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6082   -8.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9008   -8.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6831   -6.9124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9015   -7.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928   -8.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7307   -2.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4379   -2.0054    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  6
 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
 24 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101985

   ---

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: 482.05

Molecular Weight (Monoisotopic): 481.1478

AlogP: 6.49

#Rotatable Bonds: 7

Polar Surface Area: 30.93

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.69

CX LogD: 6.69

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -0.85

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