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Substrate Report for: Orlistat

Name Class
OrlistatTypeOxooxetan
Lipase inhibitor
Other_Name (14)
Chemical_Nomenclature[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
FormulaC29H53NO5
CAS_number96829-58-2
MW495.73
PaperMalone_1998_IDrugs_1_232
Xiao_2013_Biochem.Pharmacol_85_439
Pemble_2007_Nat.Struct.Mol.Biol_14_704
Khan_2021_ACS.Infect.Dis_7_2876
CommentNon-specific lipase inhibitor. Orlistat is a drug designed to treat obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested. The structure of FASN with orlistat shows that it is hydrolysed. Orlistat is a saturated derivative of the natural compound Lipstatin, isolated from Streptomyces toxytricini
Gene_locushuman-FASN
CID3034010
FamilyThioesterase
InChIKeyAHLBNYSZXLDEJQ-FWEHEUNISA-N
AHLBNYSZXLDEJQ-UHFFFAOYSA-N
CanonicalSMILESCCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=O
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
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)
IupharLig5277
WikipediaOrlistat

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Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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