ID: ALA285901

Max Phase: Preclinical

Molecular Formula: C20H23NO4

Molecular Weight: 341.41

Molecule Type: Small molecule

Representations

Synonyms (1): Dimethylamino-3',4',5'-Trimethoxychalcone
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(C(=O)/C=C/c2ccc(N(C)C)cc2)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H23NO4/c1-21(2)16-9-6-14(7-10-16)8-11-17(22)15-12-18(23-3)20(25-5)19(13-15)24-4/h6-13H,1-5H3/b11-8+

Standard InChI Key:  UVWVWBTZPMIHCN-DHZHZOJOSA-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: 341.41

Molecular Weight (Monoisotopic): 341.1627

AlogP: 3.67

#Rotatable Bonds: 7

Polar Surface Area: 48.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 4.73

CX LogP: 3.53

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -0.18

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

3. 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]

4. 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]

5. Rao YK, Fang SH, Tzeng YM..  (2009)  Synthesis and biological evaluation of 3',4',5'-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation.,  17  (23): [PMID:19875299] [10.1016/j.bmc.2009.10.022]

6. Lai CH, Rao YK, Fang SH, Sing YT, Tzeng YM..  (2010)  Identification of 3',4',5'-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation in human gastric epithelial cells.,  20  (18): [PMID:20705463] [10.1016/j.bmcl.2010.07.094]

7. Rao YK, Kao TY, Wu MF, Ko JL, Tzeng YM..  (2010)  Identification of small molecule inhibitors of telomerase activity through transcriptional regulation of hTERT and calcium induction pathway in human lung adenocarcinoma A549 cells.,  18  (19): [PMID:20813535] [10.1016/j.bmc.2010.08.021]

8. Wu J, Li J, Cai Y, Pan Y, Ye F, Zhang Y, Zhao Y, Yang S, Li X, Liang G..  (2011)  Evaluation and discovery of novel synthetic chalcone derivatives as anti-inflammatory agents.,  54  (23): [PMID:21988173] [10.1021/jm200946h]

9. Salum LB, Altei WF, Chiaradia LD, Cordeiro MN, Canevarolo RR, Melo CP, Winter E, Mattei B, Daghestani HN, Santos-Silva MC, Creczynski-Pasa TB, Yunes RA, Yunes JA, Andricopulo AD, Day BW, Nunes RJ, Vogt A..  (2013)  Cytotoxic 3,4,5-trimethoxychalcones as mitotic arresters and cell migration inhibitors.,  63  [PMID:23524161] [10.1016/j.ejmech.2013.02.037]

10. Meegan MJ, Nathwani S, Twamley B, Zisterer DM, O'Boyle NM..  (2017)  Piperlongumine (piplartine) and analogues: Antiproliferative microtubule-destabilising agents.,  125  [PMID:27689728] [10.1016/j.ejmech.2016.09.048]

Source

Source(1):

• Scientific Literature