3,5-Bis(2-bromobenzylidene)-4-piperidone

ID: ALA1254461

Chembl Id: CHEMBL1254461

PubChem CID: 52941456

Max Phase: Preclinical

Molecular Formula: C19H15Br2NO

Molecular Weight: 433.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccccc2Br)CNC/C1=C\c1ccccc1Br

Standard InChI:  InChI=1S/C19H15Br2NO/c20-17-7-3-1-5-13(17)9-15-11-22-12-16(19(15)23)10-14-6-2-4-8-18(14)21/h1-10,22H,11-12H2/b15-9+,16-10+

Standard InChI Key:  SRIXJFUIIDOCNK-KAVGSWPWSA-N

Alternative Forms

1. Parent:

   

   ALA1254461

   (3E,5E)-3,5-bis[(2-bromophenyl)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: 433.14

Molecular Weight (Monoisotopic): 430.9520

AlogP: 4.85

#Rotatable Bonds: 2

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.36

CX LogP: 5.44

CX LogD: 5.40

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.34

References

1. Lagisetty P, Vilekar P, Sahoo K, Anant S, Awasthi V..  (2010)  CLEFMA-an anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones.,  18  (16): [PMID:20638855] [10.1016/j.bmc.2010.06.055]

2. Jin R, Chen Q, Yao S, Bai E, Fu W, Wang L, Wang J, Du X, Wei T, Xu H, Jiang C, Qiu P, Wu J, Li W, Liang G..  (2018)  Synthesis and anti-tumor activity of EF24 analogues as IKKβ inhibitors.,  144  [PMID:29351887] [10.1016/j.ejmech.2017.11.077]

3. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]

Source

Source(1):

• Scientific Literature