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Inhibitor Report for: Lipstatin

Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product that was first isolated from the Actinobacterium Streptomyces toxytricini. Orlistat is a saturated derivative of the natural compound Lipstatin.


General
Type Oxooxetan, Natural, Lipase inhibitor
Chemical_Nomenclature [(2S,4Z,7Z)-1-[(2S,3R)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate
Canonical SMILES CCCCCCC1C(OC1=O)CC(CC=CCC=CCCCCC)OC(=O)C(CC(C)C)NC=O
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
InChIKey OQMAKWGYQLJJIA-MJASSXQFSA-N
Other name(s) (-)-Lipstatin ; ZINC77301888 ; N-Formyl-L-leucine (1S,3Z,6Z)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadien-1-yl Ester ; N-Formyl-L-leucine [2S-[2|A(1R*,3Z,6Z),3|A]]-1-[(3-Hexyl-4-oxo-2-oxetanyl)methyl]-3,6-dodecadienyl Ester
________________________________________________________________________________________________
MW|491.70
Formula|C29H49NO5
CAS_number|
PubChem|71749817
UniChem|OQMAKWGYQLJJIA-MJASSXQFSA-N
IUPHAR|
Wikipedia|Lipstatin

Target
Families | Lipstatin ligand of proteins in family: Pancreatic_lipase

References:
Search PubMed for references concerning: Lipstatin
    Title: Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase
    Bai T, Zhang D, Lin S, Long Q, Wang Y, Ou H, Kang Q, Deng Z, Liu W, Tao M
    Ref: Applied Environmental Microbiology, 80:7473, 2014 : PubMed

            

    Title: Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity
    Weibel EK, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H
    Ref: J Antibiot (Tokyo), 40:1081, 1987 : PubMed