bestatin   Click here for help

GtoPdb Ligand ID: 5151

Synonyms: ubenimex
Compound class: Synthetic organic
Comment: Bestatin is a transition-state analogue of the dipeptide PheLeu, a substrate for aminopeptidases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 112.65
Molecular weight 308.17
XLogP -0.92
No. Lipinski's rules broken 0
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Canonical SMILES OC(C(=O)NC(C(=O)O)CC(C)C)C(Cc1ccccc1)N
Isomeric SMILES O[C@H](C(=O)N[C@@H](C(=O)O)CC(C)C)[C@@H](Cc1ccccc1)N
InChI InChI=1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13-,14+/m1/s1
1. Grembecka J, Mucha A, Cierpicki T, Kafarski P. (2003)
The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity.
J Med Chem, 46 (13): 2641-55. [PMID:12801228]
2. Orning L, Krivi G, Fitzpatrick FA. (1991)
Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes.
J Biol Chem, 266 (3): 1375-8. [PMID:1846352]
3. Taylor A, Peltier CZ, Torre FJ, Hakamian N. (1993)
Inhibition of bovine lens leucine aminopeptidase by bestatin: number of binding sites and slow binding of this inhibitor.
Biochemistry, 32 (3): 784-90. [PMID:8422382]