2-{3-[(Ethylmethylamino)methyl]benzyl}-5,6-dimethoxy-benzofuran-3(2H)-one

ID: ALA472812

Max Phase: Preclinical

Molecular Formula: C21H25NO4

Molecular Weight: 355.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(C)Cc1cccc(CC2Oc3cc(OC)c(OC)cc3C2=O)c1

Standard InChI:  InChI=1S/C21H25NO4/c1-5-22(2)13-15-8-6-7-14(9-15)10-20-21(23)16-11-18(24-3)19(25-4)12-17(16)26-20/h6-9,11-12,20H,5,10,13H2,1-4H3

Standard InChI Key:  RRUPPYSATHGXPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.4711   -6.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3867   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -5.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -6.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2772   -6.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -6.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -6.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -7.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -7.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -4.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -8.3477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521   -8.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521   -6.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1625   -7.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704   -5.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0461   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624   -5.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -6.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624   -7.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0461   -6.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1910   -5.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991   -5.9253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991   -6.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -5.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -4.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  5  9  2  0
  4  6  2  0
  3 10  2  0
 11 12  1  0
  8 11  1  0
 13 14  1  0
  7 13  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 23 24  1  0
 25 26  1  0
 23 25  1  0
 22 23  1  0
 18 22  1  0
  2 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472812

   ---

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: 355.43

Molecular Weight (Monoisotopic): 355.1784

AlogP: 3.34

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.12

CX Basic pKa: 8.32

CX LogP: 2.89

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -0.03

References

1. Sheng R, Xu Y, Hu C, Zhang J, Lin X, Li J, Yang B, He Q, Hu Y..  (2009)  Design, synthesis and AChE inhibitory activity of indanone and aurone derivatives.,  44  (1): [PMID:18436348] [10.1016/j.ejmech.2008.03.003]

Source

Source(1):

• Scientific Literature