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

ID: ALA247467

PubChem CID: 44438163

Max Phase: Preclinical

Molecular Formula: C24H28N2O6

Molecular Weight: 440.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(Cc1ccc(OC)c3oc(C(=O)NCCO)cc13)CC2

Standard InChI:  InChI=1S/C24H28N2O6/c1-29-19-5-4-16(18-12-22(32-23(18)19)24(28)25-7-9-27)13-26-8-6-15-10-20(30-2)21(31-3)11-17(15)14-26/h4-5,10-12,27H,6-9,13-14H2,1-3H3,(H,25,28)

Standard InChI Key:  PPZVXGFCJBVSNP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.2276  -11.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5128  -11.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5146   -9.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0103  -10.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5137  -12.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997  -12.8285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4768  -13.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5195   -9.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4778  -12.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929  -10.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762  -11.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846  -10.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4596  -10.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -9.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -9.3059    0.0000 O   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:

   

   ALA247467

   4-[(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)methyl]-N-(2-hydroxyethyl)-7-methoxy-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: 440.50

Molecular Weight (Monoisotopic): 440.1947

AlogP: 2.74

#Rotatable Bonds: 8

Polar Surface Area: 93.40

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.24

CX LogP: 1.67

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -0.65

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