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

ID: ALA358648

PubChem CID: 10339796

Max Phase: Preclinical

Molecular Formula: C19H21F2NO5

Molecular Weight: 381.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CC2NCCc3c(F)c(O)c(O)c(F)c32)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H21F2NO5/c1-25-12-7-9(8-13(26-2)19(12)27-3)6-11-14-10(4-5-22-11)15(20)17(23)18(24)16(14)21/h7-8,11,22-24H,4-6H2,1-3H3

Standard InChI Key:  JSUCHNUEMCJTOS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.1625   -2.5375    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
    2.7375   -2.5417    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
    2.7375   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -1.3000    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   -5.0167    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
    7.0125   -4.1917    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
    5.5792   -5.0167    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
    3.4417   -3.7792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.4750    0.0000 F   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
    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
    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  6  1  0
  6  4  2  0
  7  1  1  0
  8 10  1  0
  9 14  1  0
 10 15  2  0
 11 13  1  0
 12  7  1  0
 13  7  1  0
 14 11  2  0
 15 11  1  0
 16  2  1  0
 17  6  1  0
 18  3  1  0
 19  5  1  0
 20  8  1  0
 21  4  1  0
 22 10  1  0
 23  9  1  0
 24 12  1  0
 25 20  1  0
 26 22  1  0
 27 23  1  0
 24 21  1  0
  5  3  2  0
  8  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA358648

   TMQ, 5,8-Difluoro

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: 381.38

Molecular Weight (Monoisotopic): 381.1388

AlogP: 2.83

#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: 7.28

CX Basic pKa: 10.95

CX LogP: 2.20

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: 0.59

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