Structure via PubChem · Public domain (PubChem)
Lipstatin
Sign in to saveAlso known as L-Leucine, N-formyl-, (1S,3Z,6Z)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadien-1-yl ester, L-Leucine, N-formyl-, (1S,3Z,6Z)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadienyl ester, (-)-Lipstatin
Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product that was first isolated from the actinobacterium Streptomyces toxytricini.
Chemical data
- Formula
- C29H49NO5
- Molecular weight
- 491.7 g/mol
- 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
- SMILES
- CCCCCC[C@H]1[C@@H](OC1=O)C[C@H](C/C=C\C/C=C\CCCCC)OC(=O)[C@H](CC(C)C)NC=O
- InChIKey
- OQMAKWGYQLJJIA-CUOOPAIESA-N
- XLogP
- 8.7
- Polar surface area
- 81.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- lactone
- Mass
- 491.361074
Show 3 more facts
- chemical formula
- C₂₉H₄₉NO₅
- canonical SMILES
- CCCCCCC1C(OC1=O)CC(CC=CCC=CCCCCC)OC(=O)C(CC(C)C)NC=O
- isomeric SMILES
- CCCCCC[C@H]1[C@@H](OC1=O)C[C@H](C/C=C\C/C=C\CCCCC)OC(=O)[C@H](CC(C)C)NC=O
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Biosynthesis
- See also
- References
Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product that was first isolated from the actinobacterium Streptomyces toxytricini.
The popular antiobesity drug orlistat (trade names Xenical and alli) is a saturated derivative of lipstatin.
Excerpted from Wikipedia’s “Lipstatin” article, available under the CC BY-SA 4.0 licence.