Lipstatin

Lipstatin
Names
Systematic IUPAC name
(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl (2S)-2-formamido-4-methylpentanoate
Other names
(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-4,7-tridecadien-2-yl N-formyl-L-leucinate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.126.007
MeSH Lipstatin
PubChem CID
UNII
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
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
Properties
Chemical formula
 C29H49NO5
Molar mass 491.713 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product that 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.

  1. ^ 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. doi:10.7164/antibiotics.40.1081. PMID 3680018.
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