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
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(OC2C(CO)OC(C(C2O)O)O)C(C(C1OC1OC(C)C(C(C1O)O)NC1C=C(CO)C(C(C1O)O)O)O)O
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
InChI Key XUFXOAAUWZOOIT-SXARVLRPSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2007), UK (2009), Germany, France, Hungary, Poland, Portugal (2011))
IUPAC Name Click here for help
(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
International Nonproprietary Names Click here for help
INN number INN
4527 acarbose
Synonyms Click here for help
BAY-G 5421 | BAY-G-5421 | Glucobay® | Precose®
Database Links Click here for help
CAS Registry No. 56180-94-0
ChEBI CHEBI:2376
ChEMBL Ligand CHEMBL1566
DrugBank Ligand DB00284
GtoPdb PubChem SID 178103397
PubChem CID 444254
RCSB PDB Ligand QPS
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Search UniChem for chemical match using the InChIKey XUFXOAAUWZOOIT-SXARVLRPSA-N
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Wikipedia Acarbose

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Tocris
Acarbose
Cat. No. 2673