Orlistat
[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
Molecular Identity
Orlistat
[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
PubChem CID: 3034010
Orlistat is 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. It has a role as an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 2.3.1.85 (fatty acid synthase) inhibitor, an anti-obesity agent and a bacterial metabolite. It is a member of formamides, a L-leucine derivative, a carboxylic ester and a beta-lactone.
2D Structure
Properties
C29H53NO5
Molecular Formula
495.70
Molecular Weight
g/mol
495.3924
Exact Mass
Da
10
XLogP
Above Lipinski threshold
81.7
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
5
H-Bond Acceptors
579
Complexity
SMILES
Canonical SMILES
SMILES: CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=OIsomeric SMILES
SMILES: CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=OSynonyms(20)
orlistat96829-58-2TetrahydrolipstatinXenicalOrlipastatAlli(-)-TetrahydrolipstatinTHLPtetrahydrolipastatinRo 18-0647/002orlistatum[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoateDTXSID8023395Ro-18-0647/002(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
Data from PubChem (NCBI)
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Drug Network
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