ID: ALA32353

Max Phase: Preclinical

Molecular Formula: C18H18O4

Molecular Weight: 298.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(C(=O)/C=C/c2ccccc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C18H18O4/c1-20-16-11-14(12-17(21-2)18(16)22-3)15(19)10-9-13-7-5-4-6-8-13/h4-12H,1-3H3/b10-9+

Standard InChI Key:  HJRVQVGPAQZDPJ-MDZDMXLPSA-N

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

Properties

Molecular Weight: 298.34

Molecular Weight (Monoisotopic): 298.1205

AlogP: 3.61

#Rotatable Bonds: 6

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: 0.12

References

1. Batt DG, Goodman R, Jones DG, Kerr JS, Mantegna LR, McAllister C, Newton RC, Nurnberg S, Welch PK, Covington MB..  (1993)  2'-substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis.,  36  (10): [PMID:8496911] [10.1021/jm00062a016]

2. Meng CQ, Zheng XS, Ni L, Ye Z, Simpson JE, Worsencroft KJ, Hotema MR, Weingarten MD, Skudlarek JW, Gilmore JM, Hoong LK, Hill RR, Marino EM, Suen KL, Kunsch C, Wasserman MA, Sikorski JA..  (2004)  Discovery of novel heteroaryl-substituted chalcones as inhibitors of TNF-alpha-induced VCAM-1 expression.,  14  (6): [PMID:15006393] [10.1016/j.bmcl.2004.01.021]

3. Edwards ML, Stemerick DM, Sunkara PS..  (1990)  Chalcones: a new class of antimitotic agents.,  33  (7): [PMID:2362275] [10.1021/jm00169a021]

4. Bhat BA, Dhar KL, Puri SC, Saxena AK, Shanmugavel M, Qazi GN..  (2005)  Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents.,  15  (12): [PMID:15893928] [10.1016/j.bmcl.2005.03.121]

5. Batovska D, Parushev S, Slavova A, Bankova V, Tsvetkova I, Ninova M, Najdenski H..  (2007)  Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans.,  42  (1): [PMID:17007965] [10.1016/j.ejmech.2006.08.012]

6. Romagnoli R, Baraldi PG, Carrion MD, Cara CL, Cruz-Lopez O, Preti D, Tolomeo M, Grimaudo S, Di Cristina A, Zonta N, Balzarini J, Brancale A, Sarkar T, Hamel E..  (2008)  Design, synthesis, and biological evaluation of thiophene analogues of chalcones.,  16  (10): [PMID:18440234] [10.1016/j.bmc.2008.04.026]

7. Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H..  (2009)  Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted.,  44  (5): [PMID:18584918] [10.1016/j.ejmech.2008.05.010]

8. Srinivasan B, Johnson TE, Lad R, Xing C..  (2009)  Structure-activity relationship studies of chalcone leading to 3-hydroxy-4,3',4',5'-tetramethoxychalcone and its analogues as potent nuclear factor kappaB inhibitors and their anticancer activities.,  52  (22): [PMID:19883086] [10.1021/jm901278z]

9. Bonesi M, Loizzo MR, Statti GA, Michel S, Tillequin F, Menichini F..  (2010)  The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives.,  20  (6): [PMID:20167484] [10.1016/j.bmcl.2010.01.113]

10. Kumar V, Kumar S, Hassan M, Wu H, Thimmulappa RK, Kumar A, Sharma SK, Parmar VS, Biswal S, Malhotra SV..  (2011)  Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells.,  54  (12): [PMID:21539383] [10.1021/jm2002348]

11. Shakil NA, Singh MK, Sathiyendiran M, Kumar J, Padaria JC..  (2013)  Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.,  59  [PMID:23229055] [10.1016/j.ejmech.2012.10.038]

Source

Source(1):

• Scientific Literature