6-Methoxy-2-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinolin-7-ol

ID: ALA2172345

PubChem CID: 71457084

Max Phase: Preclinical

Molecular Formula: C19H23NO3

Molecular Weight: 313.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCN2CCc3cc(OC)c(O)cc3C2)cc1

Standard InChI:  InChI=1S/C19H23NO3/c1-22-17-5-3-14(4-6-17)7-9-20-10-8-15-12-19(23-2)18(21)11-16(15)13-20/h3-6,11-12,21H,7-10,13H2,1-2H3

Standard InChI Key:  GPFSNELVAXRLCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   10.1673  -32.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4529  -33.3046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4529  -34.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1673  -34.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818  -34.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5963  -34.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3107  -34.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3107  -33.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5963  -32.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818  -33.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0252  -32.8921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7384  -32.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0239  -33.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094  -32.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094  -32.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5950  -31.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8805  -32.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8805  -32.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5950  -33.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1660  -31.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516  -32.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0252  -34.5421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7397  -34.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  8 11  1  0
 12 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 17 20  1  0
 13 14  1  0
  2 12  1  0
 22 23  1  0
  7 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2172345

   6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-3,4-dihydro-1H-isoquinolin-7-ol

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: 313.40

Molecular Weight (Monoisotopic): 313.1678

AlogP: 3.01

#Rotatable Bonds: 5

Polar Surface Area: 41.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.14

CX Basic pKa: 8.11

CX LogP: 3.35

CX LogD: 2.56

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -0.18

References

1. Horling A, Müller C, Barthel R, Bracher F, Imming P..  (2012)  A new class of selective and potent 7-dehydrocholesterol reductase inhibitors.,  55  (17): [PMID:22882119] [10.1021/jm3006096]

Source

Source(1):

• Scientific Literature