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

ID: ALA143645

PubChem CID: 15133335

Max Phase: Preclinical

Molecular Formula: C20H22F3NO5

Molecular Weight: 413.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CC2NCCc3c2cc(O)c(O)c3C(F)(F)F)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H22F3NO5/c1-27-15-7-10(8-16(28-2)19(15)29-3)6-13-12-9-14(25)18(26)17(20(21,22)23)11(12)4-5-24-13/h7-9,13,24-26H,4-6H2,1-3H3

Standard InChI Key:  BHLICJAYUSKMQT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.4500   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -2.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    0.2833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042    0.0750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.0708    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -5.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -2.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -6.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -6.6667    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  8  1  0
  7 11  2  0
  8  5  2  0
  9  3  1  0
 10 15  2  0
 11 16  1  0
 12 14  1  0
 13 26  1  0
 14  9  1  0
 15 12  1  0
 16 12  2  0
 17  4  1  0
 18  4  1  0
 19  4  1  0
 20  5  1  0
 21  7  1  0
 22  8  1  0
 23  2  1  0
 24 10  1  0
 25 11  1  0
 26 23  1  0
 27 21  1  0
 28 24  1  0
 29 25  1  0
  3  6  2  0
 13  9  1  0
 10  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA143645

   TMQ, 5-TrifluoroMe

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: 413.39

Molecular Weight (Monoisotopic): 413.1450

AlogP: 3.57

#Rotatable Bonds: 5

Polar Surface Area: 80.18

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.04

CX Basic pKa: 8.94

CX LogP: 2.72

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: 0.82

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