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
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Leucine aminopeptidase 3 Bt Inhibitor Inhibition 9.2 pKi - 1,3
pKi 9.2 (Ki 6x10-10 M) [1,3]
Leukotriene A4 hydrolase Hs Inhibitor Inhibition 5.4 pKi - 2
pKi 5.4 (Ki 4x10-6 M) [2]
Description: Inhibition of LTB4 formation by isolated human enzyme in vitro.