1-Acryloyl-3,5-bis-(4-methoxy-benzylidene)-piperidin-4-one

ID: ALA155539

Chembl Id: CHEMBL155539

PubChem CID: 5469428

Max Phase: Preclinical

Molecular Formula: C24H23NO4

Molecular Weight: 389.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1C/C(=C\c2ccc(OC)cc2)C(=O)/C(=C/c2ccc(OC)cc2)C1

Standard InChI:  InChI=1S/C24H23NO4/c1-4-23(26)25-15-19(13-17-5-9-21(28-2)10-6-17)24(27)20(16-25)14-18-7-11-22(29-3)12-8-18/h4-14H,1,15-16H2,2-3H3/b19-13+,20-14+

Standard InChI Key:  HUKFHMCTPWIOSR-IWGRKNQJSA-N

Alternative Forms

1. Parent:

   

   ALA155539

   4-Piperidinone,5-bis[(4-methoxyphenyl)methylene]-1-(1-oxo-2-propenyl)-

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: 389.45

Molecular Weight (Monoisotopic): 389.1627

AlogP: 3.77

#Rotatable Bonds: 5

Polar Surface Area: 55.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.05

References

1. Dimmock JR, Padmanilayam MP, Puthucode RN, Nazarali AJ, Motaganahalli NL, Zello GA, Quail JW, Oloo EO, Kraatz HB, Prisciak JS, Allen TM, Santos CL, Balzarini J, De Clercq E, Manavathu EK..  (2001)  A conformational and structure-activity relationship study of cytotoxic 3,5-bis(arylidene)-4-piperidones and related N-acryloyl analogues.,  44  (4): [PMID:11170648] [10.1021/jm0002580]

2. Pati HN, Das U, Quail JW, Kawase M, Sakagami H, Dimmock JR..  (2008)  Cytotoxic 3,5-bis(benzylidene)piperidin-4-ones and N-acyl analogs displaying selective toxicity for malignant cells.,  43  (1): [PMID:17499885] [10.1016/j.ejmech.2007.03.010]

3. PubChem BioAssay data set, 

4. 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(2):

• Scientific Literature
• PubChem BioAssays