CHEBI:94686 - orlistat

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ChEBI Name orlistat
ChEBI ID CHEBI:94686
Definition A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C29H53NO5
Net Charge 0
Average Mass 495.736
Monoisotopic Mass 495.392
InChI InChI=1S/C29H53NO5/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/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChIKey AHLBNYSZXLDEJQ-FWEHEUNISA-N
SMILES [C@@]1(OC([C@]1(CCCCCC)[H])=O)(C[C@H](CCCCCCCCCCC)OC([C@@H](NC(=O)[H])CC(C)C)=O)[H]
Metabolite of Species Details
Streptomyces toxytricini (NCBI:txid67369) Isolated from fermentation broth See: EP129748
Roles Classification
Biological Role(s): anti-obesity agent
Any substance which is used to reduce or control weight.
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of triacylglycerol lipase (EC 3.1.1.3).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 2.3.1.85 (fatty acid synthase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of fatty acid synthase (EC 2.3.1.85), a multi-enzyme protein involved in fatty acid synthesis.
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ChEBI Ontology
Outgoing orlistat (CHEBI:94686) has role anti-obesity agent (CHEBI:74518)
orlistat (CHEBI:94686) has role bacterial metabolite (CHEBI:76969)
orlistat (CHEBI:94686) has role EC 2.3.1.85 (fatty acid synthase) inhibitor (CHEBI:71476)
orlistat (CHEBI:94686) has role EC 3.1.1.3 (triacylglycerol lipase) inhibitor (CHEBI:65001)
orlistat (CHEBI:94686) is a β-lactone (CHEBI:49043)
orlistat (CHEBI:94686) is a L-leucine derivative (CHEBI:25018)
orlistat (CHEBI:94686) is a carboxylic ester (CHEBI:33308)
orlistat (CHEBI:94686) is a formamides (CHEBI:24079)
IUPAC Name
(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate
INNs Sources
orlistat ChEBI
orlistat ChEBI
orlistat ChEBI
orlistatum ChEBI
Synonyms Sources
(−)-tetrahydrolipostatin ChEBI
(2S)-2-formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester ChEBI
N-formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester ChEBI
orlipastat ChEBI
Ro-18-0647 ChEBI
Brand Names Sources
Alli ChemIDplus
Xenical ChemIDplus
Manual Xrefs Databases
1996 DrugCentral
D04028 KEGG DRUG
EP129748 Patent
LSM-5724 LINCS
Orlistat Wikipedia
US4598089 Patent
View more database links
Registry Numbers Types Sources
3658031 Reaxys Registry Number Reaxys
96829-58-2 CAS Registry Number ChemIDplus
96829-58-2 CAS Registry Number DrugCentral
Citations Waiting for Citations Types Sources
27793869 PubMed citation Europe PMC
28097013 PubMed citation Europe PMC
28191026 PubMed citation Europe PMC
28260907 PubMed citation Europe PMC
28387458 PubMed citation Europe PMC
28559211 PubMed citation Europe PMC
28588183 PubMed citation Europe PMC
28624425 PubMed citation Europe PMC
Last Modified
25 July 2017