8-Fluoro-1-(3,4,5-trimethoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol

ID: ALA1788251

PubChem CID: 13720716

Max Phase: Preclinical

Molecular Formula: C19H22FNO5

Molecular Weight: 363.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C[C@@H]2NCCc3cc(O)c(O)c(F)c32)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H22FNO5/c1-24-14-7-10(8-15(25-2)19(14)26-3)6-12-16-11(4-5-21-12)9-13(22)18(23)17(16)20/h7-9,12,21-23H,4-6H2,1-3H3/t12-/m0/s1

Standard InChI Key:  MKRDKFSQEPQZSX-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.2250   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.7792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -2.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -5.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -6.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6  9  1  0
  7 10  1  0
  8 14  1  0
  9 15  2  0
 10  5  2  0
 11 13  1  0
 12  4  1  0
  4 13  1  1
 14 11  2  0
 15 11  1  0
 16  2  1  0
 17  3  1  0
 18  6  1  0
 19  7  1  0
 20  8  1  0
 21  9  1  0
 22 23  1  0
 23  5  1  0
 24 18  1  0
 25 20  1  0
 26 21  1  0
 22 12  1  0
  7  3  2  0
  6  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1788251

   TMQ, S-(+)-8-Fluoro

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: 363.39

Molecular Weight (Monoisotopic): 363.1482

AlogP: 2.69

#Rotatable Bonds: 5

Polar Surface Area: 80.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.68

CX Basic pKa: 7.80

CX LogP: 2.32

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: 0.91

References

1. Markovich KM, Tantishaiyakul V, Hamada A, Miller DD, Romstedt KJ, Shams G, Shin Y, Fraundorfer PF, Doyle K, Feller DR..  (1992)  Synthesis of halogenated trimetoquinol derivatives and evaluation of their beta-agonist and thromboxane A2 (TXA2) antagonist activities.,  35  (3): [PMID:1346651] [10.1021/jm00081a007]

Source

Source(1):

• Scientific Literature