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

ID: ALA462837

PubChem CID: 25197631

Max Phase: Preclinical

Molecular Formula: C22H23NO4

Molecular Weight: 365.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(=O)/C(=C/c1ccc(CN3CCCC3)cc1)O2

Standard InChI:  InChI=1S/C22H23NO4/c1-25-19-12-17-18(13-20(19)26-2)27-21(22(17)24)11-15-5-7-16(8-6-15)14-23-9-3-4-10-23/h5-8,11-13H,3-4,9-10,14H2,1-2H3/b21-11-

Standard InChI Key:  QSSBCGZXNNGKPI-NHDPSOOVSA-N

Molfile:  

     RDKit          2D

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   -1.0844  -20.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391  -20.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853  -21.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9748  -21.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103  -21.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248  -21.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103  -22.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3853  -22.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065  -19.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3680  -20.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442  -20.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0606  -20.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770  -20.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770  -21.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0606  -22.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442  -21.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934  -22.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015  -21.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941  -20.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002  -20.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106  -21.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9563  -21.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248  -23.2075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497  -23.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497  -21.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8602  -22.4911    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
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  4  6  2  0
  3 10  2  0
 11 12  1  0
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 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
  8 24  1  0
 26 27  1  0
  7 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA462837

   (Z)-5,6-Dimethoxy-2-{4-[(pyrrolidin-1-yl)methyl]-benzylidene}-benzofuran-3(2H)-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: 365.43

Molecular Weight (Monoisotopic): 365.1627

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 48.00

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.56

CX LogP: 3.23

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.44

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