(3E,5E)-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one

ID: ALA574646

Chembl Id: CHEMBL574646

Cas Number: 342808-24-6

PubChem CID: 16079040

Max Phase: Preclinical

Molecular Formula: C17H15N3O

Molecular Weight: 277.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccccn2)CNC/C1=C\c1ccccn1

Standard InChI:  InChI=1S/C17H15N3O/c21-17-13(9-15-5-1-3-7-19-15)11-18-12-14(17)10-16-6-2-4-8-20-16/h1-10,18H,11-12H2/b13-9+,14-10+

Standard InChI Key:  GXFKPANENAOEOK-UTLPMFLDSA-N

Alternative Forms

1. Parent:

   

   ALA574646

   3,5-Bis(2-pyridylmethylene)piperidine-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: 277.33

Molecular Weight (Monoisotopic): 277.1215

AlogP: 2.12

#Rotatable Bonds: 2

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.27

CX LogP: 1.93

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.85

Np Likeness Score: -0.57

References

1. Sun A, Lu YJ, Hu H, Shoji M, Liotta DC, Snyder JP..  (2009)  Curcumin analog cytotoxicity against breast cancer cells: exploitation of a redox-dependent mechanism.,  19  (23): [PMID:19854644] [10.1016/j.bmcl.2009.10.023]

2. Brown A, Shi Q, Moore TW, Yoon Y, Prussia A, Maddox C, Liotta DC, Shim H, Snyder JP..  (2013)  Monocarbonyl curcumin analogues: heterocyclic pleiotropic kinase inhibitors that mediate anticancer properties.,  56  (9): [PMID:23550937] [10.1021/jm4002692]

3. Moore TW, Zhu S, Randolph R, Shoji M, Snyder JP..  (2014)  Liver S9 Fraction-Derived Metabolites of Curcumin Analogue UBS109.,  5  (4): [PMID:24900828] [10.1021/ml4002453]

4. Potter E, Jha M, Bhullar KS, Rupasinghe HP, Balzarini J, Jha A..  (2015)  Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors.,  23  (3): [PMID:25577711] [10.1016/j.bmc.2014.12.042]

5. Baldwin PR, Reeves AZ, Powell KR, Napier RJ, Swimm AI, Sun A, Giesler K, Bommarius B, Shinnick TM, Snyder JP, Liotta DC, Kalman D..  (2015)  Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of Mycobacterium tuberculosis.,  92  [PMID:25618016] [10.1016/j.ejmech.2015.01.020]

6. Zhang X, Xu A, Lv J, Zhang Q, Ran Y, Wei C, Wu J..  (2020)  Development of small molecule inhibitors targeting NLRP3 inflammasome pathway for inflammatory diseases.,  185  [PMID:31699536] [10.1016/j.ejmech.2019.111822]

Source

Source(1):

• Scientific Literature