2-{4-[(Diethylamino)methyl]benzyl}-5,6-dimethoxybenzofuran-3(2H)-one

ID: ALA473766

Max Phase: Preclinical

Molecular Formula: C22H27NO4

Molecular Weight: 369.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)Cc1ccc(CC2Oc3cc(OC)c(OC)cc3C2=O)cc1

Standard InChI:  InChI=1S/C22H27NO4/c1-5-23(6-2)14-16-9-7-15(8-10-16)11-21-22(24)17-12-19(25-3)20(26-4)13-18(17)27-21/h7-10,12-13,21H,5-6,11,14H2,1-4H3

Standard InChI Key:  ITFZJKJHMZSAEV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -1.3959  -14.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111  -14.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655  -13.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6186  -14.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061  -15.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436  -14.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8561  -15.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436  -15.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6186  -15.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379  -13.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8561  -16.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6811  -16.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6811  -15.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936  -15.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994  -13.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165  -14.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323  -13.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440  -14.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440  -14.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323  -15.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165  -14.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599  -15.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758  -14.9867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758  -14.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599  -13.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916  -15.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4033  -14.9867    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
 24 25  1  0
 23 24  1  0
 26 27  1  0
 23 26  1  0
 22 23  1  0
 19 22  1  0
  2 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473766

   ---

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: 369.46

Molecular Weight (Monoisotopic): 369.1940

AlogP: 3.73

#Rotatable Bonds: 8

Polar Surface Area: 48.00

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: 8.53

CX LogP: 3.17

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.71

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