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CHEBI:94686 - orlistat

ChEBI IDCHEBI:94686
ChEBI Nameorlistat
Stars
DefinitionA 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.
Last Modified25 July 2017
DownloadsMolfile
FormulaC29H53NO5
Net Charge0
Average Mass495.745
Monoisotopic Mass495.39237
SMILES[H]C(=O)N[C@@H](CC(C)C)C(=O)O[C@@H](CCCCCCCCCCC)C[C@]1([H])OC(=O)[C@@]1([H])CCCCCC
InChIInChI=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
InChIKeyAHLBNYSZXLDEJQ-FWEHEUNISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces toxytricini (ncbitaxon:67369) - Article (EP129748) Isolated from fermentation broth
Roles Classification
Biological Roles:
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.
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).
anti-obesity agent  Any substance which is used to reduce or control weight.
ChEBI Ontology
Outgoing Relation(s)
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 L-leucine derivative (CHEBI:25018)
orlistat (CHEBI:94686) is a carboxylic ester (CHEBI:33308)
orlistat (CHEBI:94686) is a formamides (CHEBI:24079)
orlistat (CHEBI:94686) is a β-lactone (CHEBI:49043)
IUPAC Name 
(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate
INNs  Source
orlistatChEBI
orlistatChEBI
orlistatumChEBI
orlistatChEBI
Synonyms  Source
(2S)-2-formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] esterChEBI
orlipastatChEBI
(−)-tetrahydrolipostatinChEBI
N-formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl esterChEBI
Ro-18-0647ChEBI
Brand Names  Source
AlliChemIDplus
XenicalChemIDplus
Manual XrefsDatabases
LSM-5724LINCS
1996DrugCentral
OrlistatWikipedia
US4598089Patent
EP129748Patent
D04028KEGG DRUG
Registry NumbersSources
Reaxys:3658031Reaxys
CAS:96829-58-2DrugCentral
CAS:96829-58-2ChemIDplus
Citations