4-((6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-N-propylbenzofuran-2-carboxamide

ID: ALA247466

PubChem CID: 44438162

Max Phase: Preclinical

Molecular Formula: C25H30N2O5

Molecular Weight: 438.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1cc2c(CN3CCc4cc(OC)c(OC)cc4C3)ccc(OC)c2o1

Standard InChI:  InChI=1S/C25H30N2O5/c1-5-9-26-25(28)23-13-19-17(6-7-20(29-2)24(19)32-23)14-27-10-8-16-11-21(30-3)22(31-4)12-18(16)15-27/h6-7,11-13H,5,8-10,14-15H2,1-4H3,(H,26,28)

Standard InChI Key:  WLTYJVBUSNBYAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.1891   -4.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9039   -5.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9021   -3.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6175   -4.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4142   -5.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8988   -4.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4063   -3.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9030   -6.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6170   -6.5535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6183   -7.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.0485   -6.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0433   -7.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4664   -7.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4676   -6.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7583   -6.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1819   -6.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1776   -7.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8934   -7.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8971   -2.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1814   -2.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8944   -6.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7238   -4.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1405   -5.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1321   -3.7576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9571   -3.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3653   -3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1903   -3.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  5  4  1  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
  4  1  2  0
 19 21  1  0
  3 10  1  0
  5  6  2  0
 22 23  1  0
 18 22  1  0
 10 11  1  0
 11 12  1  0
 24 25  1  0
  4 24  1  0
 21 26  1  0
  2  3  2  0
  8 27  1  0
  3  6  1  0
 27 28  2  0
 11 14  1  0
 27 29  1  0
 12 13  1  0
 29 30  1  0
 13 16  1  0
 30 31  1  0
 15 14  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA247466

   4-[(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)methyl]-7-methoxy-N-propyl-1-benzofuran-2-carboxamide

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: 438.52

Molecular Weight (Monoisotopic): 438.2155

AlogP: 4.16

#Rotatable Bonds: 8

Polar Surface Area: 73.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.24

CX LogP: 3.24

CX LogD: 3.01

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.57

Np Likeness Score: -0.84

References

1. Hagihara K, Kashima H, Iida K, Enokizono J, Uchida S, Nonaka H, Kurokawa M, Shimada J..  (2007)  Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective alpha(2C)-adrenergic receptor antagonists.,  17  (6): [PMID:17257841] [10.1016/j.bmcl.2006.12.094]

Source

Source(1):

• Scientific Literature