1,2-bis[3,5-bis(4-Fluorobenzylidene)-4-oxo-piperidin-1-yl]ethane-1,2-dione

ID: ALA2391207

PubChem CID: 71699540

Max Phase: Preclinical

Molecular Formula: C40H28F4N2O4

Molecular Weight: 676.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(F)cc2)CN(C(=O)C(=O)N2C/C(=C\c3ccc(F)cc3)C(=O)/C(=C/c3ccc(F)cc3)C2)C/C1=C\c1ccc(F)cc1

Standard InChI:  InChI=1S/C40H28F4N2O4/c41-33-9-1-25(2-10-33)17-29-21-45(22-30(37(29)47)18-26-3-11-34(42)12-4-26)39(49)40(50)46-23-31(19-27-5-13-35(43)14-6-27)38(48)32(24-46)20-28-7-15-36(44)16-8-28/h1-20H,21-24H2/b29-17+,30-18+,31-19+,32-20+

Standard InChI Key:  QBDBQLXGEBWRRG-BIDHLLRRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2391207

   1,2-bis[(3E,5E)-3,5-bis[(4-fluorophenyl)methylidene]-4-oxopiperidin-1-yl]ethane-1,2-dione

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: 676.67

Molecular Weight (Monoisotopic): 676.1985

AlogP: 6.70

#Rotatable Bonds: 4

Polar Surface Area: 74.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.77

CX LogD: 7.77

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.14

Np Likeness Score: -0.32

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