miglitol   Click here for help

GtoPdb Ligand ID: 4842

Synonyms: Glyset® | N-hydroxylethyl-1-deoxynojirimycin
Approved drug PDB Ligand
miglitol is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Miglitol is an iminosugar type drug which inhibits alpha-glucosidase as a mechanism to improve glycemic control in type II diabetics.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 104.39
Molecular weight 207.11
XLogP -2.26
No. Lipinski's rules broken 0
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Isomeric SMILES OCCN1C[C@H](O)[C@H]([C@@H]([C@H]1CO)O)O
InChI InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1
1. Jones K, Sim L, Mohan S, Kumarasamy J, Liu H, Avery S, Naim HY, Quezada-Calvillo R, Nichols BL, Pinto BM et al.. (2011)
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
Bioorg Med Chem, 19 (13): 3929-34. [PMID:21669536]
2. Kuriyama C, Kamiyama O, Ikeda K, Sanae F, Kato A, Adachi I, Imahori T, Takahata H, Okamoto T, Asano N. (2008)
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
Bioorg Med Chem, 16 (15): 7330-6. [PMID:18595718]
3. Mohan S, Sim L, Rose DR, Pinto BM. (2010)
Probing the active-site requirements of human intestinal N-terminal maltase-glucoamylase: Synthesis and enzyme inhibitory activities of a six-membered ring nitrogen analogue of kotalanol and its de-O-sulfonated derivative.
Bioorg Med Chem, 18 (22): 7794-8. [PMID:20970346]
4. Voss AA, Díez-Sampedro A, Hirayama BA, Loo DD, Wright EM. (2007)
Imino sugars are potent agonists of the human glucose sensor SGLT3.
Mol Pharmacol, 71 (2): 628-34. [PMID:17110502]