(E)-2-{4-[(Diethylamino)methyl]benzylidene}-5,6-dimethoxy-2,3-dihydroinden-1-one

ID: ALA464427

Cas Number: 956590-24-2

PubChem CID: 23634493

Max Phase: Preclinical

Molecular Formula: C23H27NO3

Molecular Weight: 365.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)Cc1ccc(/C=C2\Cc3cc(OC)c(OC)cc3C2=O)cc1

Standard InChI:  InChI=1S/C23H27NO3/c1-5-24(6-2)15-17-9-7-16(8-10-17)11-19-12-18-13-21(26-3)22(27-4)14-20(18)23(19)25/h7-11,13-14H,5-6,12,15H2,1-4H3/b19-11+

Standard InChI Key:  BINZQDMZAMRQON-YBFXNURJSA-N

Molfile:  

     RDKit          2D

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   -1.2424   -9.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272  -10.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1374  -10.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499  -11.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749  -11.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7874  -10.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -9.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499   -9.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692   -8.5348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6124  -10.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249  -11.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7874  -12.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6124  -12.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5265   -9.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -9.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9011   -9.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6128   -9.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6128  -10.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9011  -10.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852  -10.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286  -10.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445  -10.5034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -9.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -9.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7604  -10.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4721  -10.5034    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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  1  9  1  0
  4  9  2  0
  1 10  2  0
 11 12  1  0
  7 11  1  0
 13 14  1  0
  6 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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA464427

   (E)-2-{4-[(Diethylamino)methyl]benzylidene}-5,6-dimethoxy-2,3-dihydroinden-1-one

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: 365.47

Molecular Weight (Monoisotopic): 365.1991

AlogP: 4.37

#Rotatable Bonds: 7

Polar Surface Area: 38.77

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.67

CX LogP: 4.23

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.43

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]

2. Chitranshi N, Gupta S, Tripathi PK, Seth PK.  (2013)  New molecular scaffolds for the design of Alzheimers acetylcholinesterase inhibitors identified using ligand- and receptor-based virtual screening,  22  (5): [10.1007/s00044-012-0227-3]

3. Paolino M, Rullo M, Maramai S, de Candia M, Pisani L, Catto M, Mugnaini C, Brizzi A, Cappelli A, Olivucci M, Corelli F, Altomare CD..  (2022)  Design, synthesis and biological evaluation of light-driven on-off multitarget AChE and MAO-B inhibitors.,  13  (7.0): [PMID:35923722] [10.1039/d2md00042c]

Source

Source(1):

• Scientific Literature