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	9805651
ChemSpider	7981411^Y
MeSH	Lipstatin
Jmol-3D images	Image 1
SMILES O=C(O[C@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)C\C=C/C\C=C/CCCCC)[C@@H](NC=O)CC(C)C
InChI InChI=1S/C29H49NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27H,5-11,14,17-21H2,1-4H3,(H,30,31)/b13-12-,16-15-/t24-,25-,26-,27-/m0/s1^Y Key: OQMAKWGYQLJJIA-CUOOPAIESA-N^Y InChI=1/C29H49NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27H,5-11,14,17-21H2,1-4H3,(H,30,31)/b13-12-,16-15-/t24-,25-,26-,27-/m0/s1 Key: OQMAKWGYQLJJIA-CUOOPAIEBU
Properties
Molecular formula	C₂₉H₄₉NO₅
Molar mass	491.703 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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.