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

ID: ALA3275924

PubChem CID: 12380065

Max Phase: Preclinical

Molecular Formula: C26H30ClNO5

Molecular Weight: 435.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CC2(Cc3ccccc3)NCCc3cc(O)c(O)cc32)cc(OC)c1OC.Cl

Standard InChI:  InChI=1S/C26H29NO5.ClH/c1-30-23-11-18(12-24(31-2)25(23)32-3)16-26(15-17-7-5-4-6-8-17)20-14-22(29)21(28)13-19(20)9-10-27-26;/h4-8,11-14,27-29H,9-10,15-16H2,1-3H3;1H

Standard InChI Key:  IJAQMBITWOEZRG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.6382   -8.4501    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3764   -9.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776  -10.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628  -11.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -9.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9492   -9.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458  -10.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306  -11.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142  -10.6106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -9.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -9.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0910   -9.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924  -11.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283  -11.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127  -12.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130  -13.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017  -13.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160  -13.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111  -12.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958  -11.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6322  -13.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035  -14.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230  -11.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5100  -14.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400  -12.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6355  -14.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500  -11.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565  -12.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774  -12.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6843  -13.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726  -13.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525  -13.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491  -12.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3  4  1  0
 27 28  1  0
  8 14  1  0
 28 29  2  0
  4  7  2  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
  2  3  2  0
 31 32  1  0
 15 16  2  0
 32 33  2  0
 33 28  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: 435.52

Molecular Weight (Monoisotopic): 435.2046

AlogP: 3.95

#Rotatable Bonds: 7

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: 9.58

CX Basic pKa: 8.68

CX LogP: 4.09

CX LogD: 3.04

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 0.68

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