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

ID: ALA4091645

PubChem CID: 137654153

Max Phase: Preclinical

Molecular Formula: C27H28FNO3S

Molecular Weight: 465.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OCC2c3ccc(OC(C)C)cc3CCN2C(=S)c2cccc(F)c2)cc1

Standard InChI:  InChI=1S/C27H28FNO3S/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

Standard InChI Key:  KHYWDPSRCMXOEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.4946   -5.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4935   -6.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2015   -6.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1997   -5.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9084   -5.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9072   -6.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6134   -6.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3253   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3264   -5.4793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6157   -5.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0351   -5.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7418   -5.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0371   -4.2553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7382   -6.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4441   -6.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1538   -6.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1531   -5.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4467   -5.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6157   -4.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9080   -3.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9080   -3.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6169   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6173   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9090   -1.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1990   -1.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2021   -2.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7854   -6.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0781   -6.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8604   -5.0717    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0787   -5.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3700   -6.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9080   -0.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6151   -0.1647    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
 24 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091645

   ---

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: 465.59

Molecular Weight (Monoisotopic): 465.1774

AlogP: 5.98

#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: 6.23

CX LogD: 6.23

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.92

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