3,5-Bis(benzylidene)-1-methyl-4-piperidone

ID: ALA515242

PubChem CID: 5386934

Max Phase: Preclinical

Molecular Formula: C20H19NO

Molecular Weight: 289.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C/C(=C\c2ccccc2)C(=O)/C(=C/c2ccccc2)C1

Standard InChI:  InChI=1S/C20H19NO/c1-21-14-18(12-16-8-4-2-5-9-16)20(22)19(15-21)13-17-10-6-3-7-11-17/h2-13H,14-15H2,1H3/b18-12+,19-13+

Standard InChI Key:  GHSYIDDDJZZVKM-KLCVKJMQSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.4992   -6.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -7.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9281   -6.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9281   -6.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -5.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992   -6.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -4.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992   -4.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992   -3.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847   -3.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -3.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -3.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -4.3590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847   -4.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847   -2.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -1.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -2.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -1.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -0.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -4.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
  8 14  1  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 10 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
  2  3  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515242

   Cyto9B4

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: 289.38

Molecular Weight (Monoisotopic): 289.1467

AlogP: 3.67

#Rotatable Bonds: 2

Polar Surface Area: 20.31

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.38

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.26

References

1. Pati HN, Das U, Das S, Bandy B, De Clercq E, Balzarini J, Kawase M, Sakagami H, Quail JW, Stables JP, Dimmock JR..  (2009)  The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones.,  44  (1): [PMID:18468733] [10.1016/j.ejmech.2008.03.015]

2. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data