2-[2-(4-Fluorophenyl)ethyl]-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline

ID: ALA2172346

PubChem CID: 71453579

Max Phase: Preclinical

Molecular Formula: C18H20FNO2

Molecular Weight: 301.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1O)CCN(CCc1ccc(F)cc1)C2

Standard InChI:  InChI=1S/C18H20FNO2/c1-22-18-11-15-12-20(9-7-14(15)10-17(18)21)8-6-13-2-4-16(19)5-3-13/h2-5,10-11,21H,6-9,12H2,1H3

Standard InChI Key:  AXUWTQHVUUOVTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    9.3515  -31.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6370  -31.9439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6370  -32.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3515  -33.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0660  -32.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7804  -33.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4949  -32.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4949  -31.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7804  -31.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0660  -31.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2094  -31.5314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9238  -31.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2094  -33.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9225  -31.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2081  -31.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4936  -31.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4936  -30.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7791  -30.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0647  -30.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0647  -31.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7791  -31.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3502  -30.2939    0.0000 F   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
  8 11  1  0
  7 13  1  0
 14 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 19 22  1  0
 15 16  1  0
  2 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2172346

   2-[2-(4-fluorophenyl)ethyl]-7-methoxy-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: 301.36

Molecular Weight (Monoisotopic): 301.1478

AlogP: 3.14

#Rotatable Bonds: 4

Polar Surface Area: 32.70

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.99

CX Basic pKa: 8.23

CX LogP: 3.54

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.94

Np Likeness Score: -0.51

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