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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

Stucture :

Protein :

References (2)

Title : Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase - Bai_2014_Appl.Environ.Microbiol_80_7473
Author(s) : 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
Abstract : Bai_2014_Appl.Environ.Microbiol_80_7473
ESTHER : Bai_2014_Appl.Environ.Microbiol_80_7473
PubMedSearch : Bai_2014_Appl.Environ.Microbiol_80_7473
PubMedID: 25239907

Title : Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity - Weibel_1987_J.Antibiot.(Tokyo)_40_1081
Author(s) : Weibel EK , Hadvary P , Hochuli E , Kupfer E , Lengsfeld H
Ref : J Antibiot (Tokyo) , 40 :1081 , 1987
Abstract : Weibel_1987_J.Antibiot.(Tokyo)_40_1081
ESTHER : Weibel_1987_J.Antibiot.(Tokyo)_40_1081
PubMedSearch : Weibel_1987_J.Antibiot.(Tokyo)_40_1081
PubMedID: 3680018