1,3-bis-[3,5-bis(benzylidene)-4-oxo-piperidin-1yl]propane

ID: ALA2391222

PubChem CID: 73352019

Max Phase: Preclinical

Molecular Formula: C41H38N2O2

Molecular Weight: 590.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C\c2ccccc2)CN(CCCN2C/C(=C\c3ccccc3)C(=O)/C(=C/c3ccccc3)C2)C/C1=C\c1ccccc1

Standard InChI:  InChI=1S/C41H38N2O2/c44-40-36(24-32-14-5-1-6-15-32)28-42(29-37(40)25-33-16-7-2-8-17-33)22-13-23-43-30-38(26-34-18-9-3-10-19-34)41(45)39(31-43)27-35-20-11-4-12-21-35/h1-12,14-21,24-27H,13,22-23,28-31H2/b36-24-,37-25+,38-26+,39-27+

Standard InChI Key:  GSYUJGOKPBKKJT-NOVHRWNDSA-N

Molfile:  

     RDKit          2D

 45 50  0  0  0  0  0  0  0  0999 V2000
   14.7873  -11.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7850  -11.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4930  -12.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2032  -11.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2055  -11.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4975  -10.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9112  -12.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9123  -10.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6171  -11.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3214  -10.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0352  -11.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0447  -11.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3404  -12.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6266  -11.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4907  -13.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7736  -13.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0704  -13.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3576  -13.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3502  -14.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0534  -14.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7641  -14.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3934   -9.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4022   -8.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1156   -8.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1265   -7.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4240   -6.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7105   -7.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6996   -8.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4349   -6.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0080   -6.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2945   -7.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5920   -6.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8806   -7.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8697   -8.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5723   -8.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2857   -8.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8400   -6.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5465   -7.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5600   -8.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2748   -8.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9760   -8.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9624   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2476   -6.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0965   -9.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0873  -10.6462    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  1  0
  1  6  1  0
  4  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  5  8  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
  3 15  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 23 28  1  0
 26 29  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 31 36  2  0
 27 30  2  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 38 43  2  0
 25 37  2  0
 22 23  1  0
 22 44  1  0
 44 45  1  0
 45  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2391222

   (3E,5E)-3,5-dibenzylidene-1-[3-[(3Z,5E)-3,5-dibenzylidene-4-oxopiperidin-1-yl]propyl]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: 590.77

Molecular Weight (Monoisotopic): 590.2933

AlogP: 7.48

#Rotatable Bonds: 8

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 5.43

CX LogP: 8.45

CX LogD: 8.45

Aromatic Rings: 4

Heavy Atoms: 45

QED Weighted: 0.20

Np Likeness Score: -0.27

References

1. Das S, Das U, Michel D, Gorecki DK, Dimmock JR..  (2013)  Novel 3,5-bis(arylidene)-4-piperidone dimers: potent cytotoxins against colon cancer cells.,  64  [PMID:23644215] [10.1016/j.ejmech.2013.03.055]

2. Santiago-Vazquez Y, Das S, Das U, Robles-Escajeda E, Ortega NM, Lema C, Varela-Ramírez A, Aguilera RJ, Balzarini J, De Clercq E, Dimmock SG, Gorecki DK, Dimmock JR..  (2014)  Novel 3,5-bis(arylidene)-4-oxo-1-piperidinyl dimers: structure-activity relationships and potent antileukemic and antilymphoma cytotoxicity.,  77  [PMID:24657568] [10.1016/j.ejmech.2014.03.009]

Source

Source(1):

• Scientific Literature