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

ID: ALA4094607

PubChem CID: 137655906

Max Phase: Preclinical

Molecular Formula: C27H29NO5

Molecular Weight: 447.53

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H29NO5/c1-18(2)33-24-11-12-25-19(16-24)13-14-28(27(30)20-5-4-6-21(29)15-20)26(25)17-32-23-9-7-22(31-3)8-10-23/h4-12,15-16,18,26,29H,13-14,17H2,1-3H3

Standard InChI Key:  AKPUZCGAGJBJOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.3497  -13.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3485  -13.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0566  -14.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0548  -12.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7634  -13.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7622  -13.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4684  -14.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1803  -13.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1815  -13.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4708  -12.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8902  -12.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5969  -13.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8922  -11.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4708  -11.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631  -11.4877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631  -10.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4720  -10.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4723   -9.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7641   -9.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0540   -9.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0572  -10.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6405  -14.3562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9331  -13.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7630   -8.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4702   -7.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2251  -14.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9338  -13.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7154  -12.7195    0.0000 O   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
 17 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094607

   ---

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: 447.53

Molecular Weight (Monoisotopic): 447.2046

AlogP: 5.01

#Rotatable Bonds: 7

Polar Surface Area: 68.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.82

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.88

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -0.53

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