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Lipstatin

Lipstatin

IUPAC name	[(2S,4E,7E)-1-(3-hexyl-4-oxo-oxetan-2-yl) trideca-4,7-dien-2-yl](2S)-2-formamido- 3-methyl-pentanoate
Identifiers
CAS number	96829-59-3
PubChem	6438672
MeSH	Lipstatin
SMILES	CCCCCCC1C(OC1=O)C[C@H](C\C=C\C\C=C\ CCCCC)OC(=O)[C@H](C(C)CC)NC=O
Properties
Molecular formula	C₂₉H₄₉NO₅
Molar mass	491.703 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product, and was first isolated from the Actinobacterium Streptomyces toxytricini.^[1]

The popular antiobesity drug orlistat (trade names Xenical and alli) is a saturated derivative of lipstatin.

References

^ Weibel E, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H (1987). "Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity". J Antibiot (Tokyo) 40 (8): 1081–5. PMID 3680018.