uvaricin
Sign in to saveUvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata. Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion. A method to synthesize uvaricin was first published in 1998, and an improved stereoselective synthesis published in 2001.
Wikidata facts
- Mass
- 648.496505
Show 4 more facts
- chemical formula
- C₃₉H₆₈O₇
- canonical SMILES
- CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCCCC3=CC(OC3=O)C)O)OC(=O)C
- isomeric SMILES
- CCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCCCCC3=C[C@@H](OC3=O)C)O)OC(=O)C
- found in taxon
- Uvaria acuminata
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Encyclopedic overview
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- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470627309 | Name = (+)-Uvaricin | ImageFile = Uvaricin.svg | ImageSize = 280 | PIN = (1S)-1-[(2R,2′R,5R,5′R)-5′-{(1R)-1-Hydroxy-13-[(5S)-5-methyl-2-oxo-2,5-dihydrofuran-3-yl]tridecyl}[2,2′-bioxolan]-5-yl]undecyl acetate |Section1= |Section2= |Section3= }} Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata. Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion. A method to synthesize uvaricin was first published in 1998, and an improved stereoselective synthesis published in 2001.
== References ==
Excerpted from Wikipedia’s “uvaricin” article, available under the CC BY-SA 4.0 licence.