(E)-5,6-Dimethoxy-2-{4-[(pyrrolidin-1-yl)methyl]-benzylidene}-2,3-dihydroinden-1-one

ID: ALA465028

PubChem CID: 25197629

Max Phase: Preclinical

Molecular Formula: C23H25NO3

Molecular Weight: 363.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(=O)/C(=C/c1ccc(CN3CCCC3)cc1)C2

Standard InChI:  InChI=1S/C23H25NO3/c1-26-21-13-18-12-19(23(25)20(18)14-22(21)27-2)11-16-5-7-17(8-6-16)15-24-9-3-4-10-24/h5-8,11,13-14H,3-4,9-10,12,15H2,1-2H3/b19-11+

Standard InChI Key:  AWHGPQJIJPFEKM-YBFXNURJSA-N

Molfile:  

     RDKit          2D

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   -1.2461  -17.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304  -18.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365  -18.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469  -19.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719  -19.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865  -18.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719  -17.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469  -17.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682  -16.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297  -17.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1826  -17.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989  -17.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153  -17.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153  -18.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989  -18.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1826  -18.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317  -18.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398  -18.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1325  -17.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385  -17.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490  -17.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946  -18.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114  -18.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0218  -19.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865  -19.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114  -19.8662    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
 12 13  1  0
 13 14  2  0
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 15 16  2  0
 16 17  1  0
 12 17  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19 23  1  0
 18 19  1  0
 15 18  1  0
  2 11  2  0
 24 25  1  0
  7 24  1  0
 26 27  1  0
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA465028

   (E)-5,6-Dimethoxy-2-{4-[(pyrrolidin-1-yl)methyl]-benzylidene}-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: 363.46

Molecular Weight (Monoisotopic): 363.1834

AlogP: 4.12

#Rotatable Bonds: 5

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: 8.60

CX LogP: 3.92

CX LogD: 2.69

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.39

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]

Source

Source(1):

• Scientific Literature