(3E,5E)-3,5-Bis(2,4-dichlorobenzylidene)-1-(phenylsulfonyl)piperidin-4-one

ID: ALA3221214

PubChem CID: 90667669

Max Phase: Preclinical

Molecular Formula: C25H17Cl4NO3S

Molecular Weight: 553.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(Cl)cc2Cl)CN(S(=O)(=O)c2ccccc2)C/C1=C\c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C25H17Cl4NO3S/c26-20-8-6-16(23(28)12-20)10-18-14-30(34(32,33)22-4-2-1-3-5-22)15-19(25(18)31)11-17-7-9-21(27)13-24(17)29/h1-13H,14-15H2/b18-10+,19-11+

Standard InChI Key:  XGWDDGYOTHOLBM-XOBNHNQQSA-N

Molfile:  

     RDKit          2D

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   14.6151   -4.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7340   -7.2554    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.3738   -9.7759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8441   -8.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0958   -7.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3667   -7.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6652   -7.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6887   -8.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4136   -8.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9361   -7.3824    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7973   -7.3012    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.4680   -6.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5991   -5.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3 24  2  0
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  8 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221214

   (3E,5E)-1-(benzenesulfonyl)-3,5-bis[(2,4-dichlorophenyl)methylidene]piperidin-4-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: 553.29

Molecular Weight (Monoisotopic): 550.9683

AlogP: 7.04

#Rotatable Bonds: 4

Polar Surface Area: 54.45

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.53

CX LogD: 7.53

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -1.04

References

1. Thakur A, Manohar S, Velez Gerena CE, Zayas B, Kumar V, Malhotra SV, Rawat DS.  (2014)  Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study,  5  (5): [10.1039/C3MD00399J]

Source

Source(1):

• Scientific Literature