(-)-Lipstatin

Names

[ Name ]:
(-)-Lipstatin

[Synonym ]:
L-Leucine, N-formyl-, (1S,3Z,6Z)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadien-1-yl ester
(2S-(2alpha(1R*,3Z,6Z),3beta))-N-Formyl-L-leucine 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)-3,6-dodecadienyl ester
(2S,3S,5S,7Z,10Z)-5-[(S)-2-formamido-4-methyl-valeryloxy]-2-hexyl-3-hydroxy-7,10-hexadecadienoic acid lactone
L-Leucine,N-formyl-,1-((3-hexyl-4-oxo-2-oxetanyl)methyl)-3,6-dodecadienyl ester,(2S-(2alpha(1R*,3Z,6Z),3beta))
(2S,3S,5S,7Z,1OZ)-5-[(S)-2-formamido-4-methyl-valeryloxy]-2-hexyl-3-hydroxy-7,10-hexadecadienoic 1,3 acid lactone
(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl N-formyl-L-leucinate
(2S-(2α(1R*,3Z,6Z),3β))-N-Formyl-L-leucine 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)-3,6-dodecadienyl ester
lipstatin
(-)-lipstatin
(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-4,7-tridecadien-2-yl N-formyl-L-leucinate
(2S-(2a(1R*,3Z,6Z),3b))-N-Formyl-L-leucine 1-((3-Hexyl-4-oxo-2-oxetanyl)methyl)-3,6-dodecadienyl Ester

Biological Activity

[Description]:

Lipstatin is a very potent pancreatic lipase inhibitor can be isolated from Streptomyces toxytricini. Lipstatin inhibits the hydrolysis of trioleate by porcine pancreatic lipase with an IC50 of 0.14 μM[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vivo]

Lipstatin（20、60 mg/kg；口服；单剂量；3 天）剂量依赖性地抑制三油酸甘油酯的吸收，而油酸在小鼠体内吸收正常[1]。

[References]

[1]. Weibel E K, et al. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini I. Producing organism, fermentation, isolation and biological activity[J]. The Journal of antibiotics, 1987, 40(8): 1081-1085.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
627.4±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₉H₄₉NO₅

[ Molecular Weight ]:
491.70

[ Flash Point ]:
333.2±31.5 °C

[ Exact Mass ]:
491.361084

[ PSA ]:
81.70000

[ LogP ]:
8.05

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.485

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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