(3E,5E)-3-(4-pyridylmethylene)-5-(3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one

ID: ALA4475718

PubChem CID: 155537694

Max Phase: Preclinical

Molecular Formula: C22H24N2O4

Molecular Weight: 380.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CN(C)C/C(=C\c3ccncc3)C2=O)cc(OC)c1OC

Standard InChI:  InChI=1S/C22H24N2O4/c1-24-13-17(9-15-5-7-23-8-6-15)21(25)18(14-24)10-16-11-19(26-2)22(28-4)20(12-16)27-3/h5-12H,13-14H2,1-4H3/b17-9+,18-10+

Standard InChI Key:  XIMRJAJPDFCREW-BEQMOXJMSA-N

Molfile:  

 
     RDKit          2D

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   13.0860  -22.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0849  -23.1726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7929  -23.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5026  -23.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4998  -22.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7911  -21.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2059  -21.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9152  -22.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9157  -23.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6208  -23.5644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3294  -23.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3283  -22.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6186  -21.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6208  -24.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6146  -21.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0359  -21.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7437  -22.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7393  -23.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4463  -23.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1548  -23.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1519  -22.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4443  -21.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8580  -21.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5673  -22.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4462  -24.3803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7385  -24.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8632  -23.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8646  -24.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
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 11 12  1  0
 12 13  1  0
 10 14  1  0
 13 15  2  0
 12 16  2  0
 16 17  1  0
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 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 21 23  1  0
 23 24  1  0
 19 25  1  0
 25 26  1  0
 20 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475718

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 380.44

Molecular Weight (Monoisotopic): 380.1736

AlogP: 3.09

#Rotatable Bonds: 5

Polar Surface Area: 60.89

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.29

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: -0.25

References

1. Yao BR, Sun Y, Chen SL, Suo HD, Zhang YL, Wei H, Wang CH, Zhao F, Cong W, Xin WY, Hou GG..  (2019)  Dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones as anti-hepatoma agents by inhibiting NF-κB pathway activation.,  167  [PMID:30771605] [10.1016/j.ejmech.2019.02.020]

Source

Source(1):

• Scientific Literature