1-methyl-1-(3,4,5-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

ID: ALA3275923

PubChem CID: 12380061

Max Phase: Preclinical

Molecular Formula: C20H26ClNO5

Molecular Weight: 359.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CC2(C)NCCc3cc(O)c(O)cc32)cc(OC)c1OC.Cl

Standard InChI:  InChI=1S/C20H25NO5.ClH/c1-20(14-10-16(23)15(22)9-13(14)5-6-21-20)11-12-7-17(24-2)19(26-4)18(8-12)25-3;/h7-10,21-23H,5-6,11H2,1-4H3;1H

Standard InChI Key:  SRTUXJRQBMMXTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   16.3120   -0.4447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2736   -1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724   -2.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9872   -2.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9854   -0.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7008   -1.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -2.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4194   -2.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1358   -2.1148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1324   -1.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4126   -0.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590   -0.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576   -2.5351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4217   -3.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1373   -3.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1370   -4.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8517   -4.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5660   -4.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5611   -3.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8458   -3.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2822   -4.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8535   -5.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2730   -3.3384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1400   -6.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9900   -3.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2855   -5.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7000   -2.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  8 14  1  0
  4  7  2  0
 14 15  1  0
  2  3  2  0
 15 16  2  0
  6  5  2  0
 16 17  1  0
  5  2  1  0
 17 18  2  0
  6 11  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
 20 15  1  0
  8  9  1  0
 18 21  1  0
  9 10  1  0
 17 22  1  0
 10 11  1  0
 19 23  1  0
  6  7  1  0
 22 24  1  0
  2 12  1  0
 23 25  1  0
 21 26  1  0
  3 13  1  0
  8 27  1  0
M  END

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: 359.42

Molecular Weight (Monoisotopic): 359.1733

AlogP: 2.73

#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: 9.54

CX Basic pKa: 8.58

CX LogP: 2.49

CX LogD: 1.51

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: 0.87

References

1. Miller DD, Osei-Gyimah P, Raman RV, Feller DR..  (1977)  Synthesis of 1-substituted analogues of trimetoquinol possessing differential and selective beta-adrenergic properties.,  20  (11): [PMID:21293] [10.1021/jm00221a029]

Source

Source(1):

• Scientific Literature