acarbose   Click here for help

GtoPdb Ligand ID: 6791

Synonyms: BAY-G 5421 | BAY-G-5421 | Glucobay® | Precose®
Approved drug PDB Ligand
acarbose is an approved drug (FDA (2007), UK (2009), Germany, France, Hungary, Poland, Portugal (2011))
Compound class: Synthetic organic
Comment: Maltase-glucoamylase and pancreatic amylase inhibitor. Many isomeric alternative structures for this compound are available: to go to the PubChem listing click here. It is not clear which isomer is an exact match to the structure given in the INN record for this compound.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 19
Hydrogen bond donors 14
Rotatable bonds 9
Topological polar surface area 321.17
Molecular weight 645.25
XLogP -5.53
No. Lipinski's rules broken 2
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Isomeric SMILES OC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)N[C@H]1C=C(CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-/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. Patil VS, Nandre KP, Ghosh S, Rao VJ, Chopade BA, Bhosale SV, Bhosale SV. (2012)
Synthesis and glycosidase inhibitory activity of novel (2-phenyl-4H-benzopyrimedo[2,1-b]-thiazol-4-yliden)acetonitrile derivatives.
Bioorg Med Chem Lett, 22 (23): 7011-4. [PMID:23102653]