6-Hydroxy-7-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

ID: ALA2172349

PubChem CID: 71462481

Max Phase: Preclinical

Molecular Formula: C19H23NO3

Molecular Weight: 313.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CCN2CCc3cc(O)c(OC)cc3C2)c1

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

Standard InChI Key:  XYHOSURPOZRNRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    9.7675  -32.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0574  -33.3926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0660  -34.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -34.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4949  -34.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2136  -34.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9237  -34.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9151  -33.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1963  -32.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4862  -33.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3386  -32.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6285  -33.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9097  -33.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9011  -32.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1823  -31.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722  -32.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4809  -33.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996  -33.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1737  -30.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4549  -30.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252  -32.9426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3440  -33.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425  -34.5925    0.0000 O   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
 11 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  1  0
 15 19  1  0
 12 13  1  0
  2 11  1  0
 21 22  1  0
  8 21  1  0
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2172349

   7-methoxy-2-[2-(3-methoxyphenyl)ethyl]-3,4-dihydro-1H-isoquinolin-6-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: 9.99

CX Basic pKa: 8.17

CX LogP: 3.24

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -0.26

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