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3',4'-DIMETHOXYCHALCONE
ID: ALA32880
Max Phase: Preclinical
Molecular Formula: C17H16O3
Molecular Weight: 268.31
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): 3',4'-Dimethoxychalcone
Synonyms from Alternative Forms(1):
Canonical SMILES: COc1ccc(C(=O)/C=C/c2ccccc2)cc1OC
Standard InChI: InChI=1S/C17H16O3/c1-19-16-11-9-14(12-17(16)20-2)15(18)10-8-13-6-4-3-5-7-13/h3-12H,1-2H3/b10-8+
Standard InChI Key: DJUDWUHRZBILKP-CSKARUKUSA-N
Associated Targets(Human)
Associated Targets(non-human)
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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 268.31 | Molecular Weight (Monoisotopic): 268.1099 | AlogP: 3.60 | #Rotatable Bonds: 5 |
| Polar Surface Area: 35.53 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 3.57 | CX LogD: 3.57 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.61 | Np Likeness Score: -0.08 |
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. Avila HP, Smânia Ede F, Monache FD, Smânia A.. (2008) Structure-activity relationship of antibacterial chalcones., 16 (22): [PMID:18951808] [10.1016/j.bmc.2008.09.064] |
| 4. 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] |
| 5. Kim YS, Kumar V, Lee S, Iwai A, Neckers L, Malhotra SV, Trepel JB.. (2012) Methoxychalcone inhibitors of androgen receptor translocation and function., 22 (5): [PMID:22310230] [10.1016/j.bmcl.2011.12.141] |
| 6. 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] |
