CHEBI:2376 - acarbose

ChEBI IDCHEBI:2376
ChEBI Nameacarbose
Stars
DefinitionA tetrasaccharide derivative consisting of a dideoxy-4-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl C7 cyclitol moiety [called valienol (or valienamine)] linked via nitrogen to isomaltotriose.
Secondary ChEBI IDCHEBI:40513
Last Modified22 September 2021
DownloadsMolfile
FormulaC25H43NO18
Net Charge0
Average Mass645.608
Monoisotopic Mass645.24801
SMILESC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=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
InChIKeyXUFXOAAUWZOOIT-UGEKTDRHSA-N
Wikipedia
Roles Classification
Biological Roles:
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
EC 3.2.1.1 (alpha-amylase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-amylase (EC 3.2.1.1).
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
hypoglycemic agent  A drug which lowers the blood glucose level.
ChEBI Ontology
Outgoing Relation(s)
acarbose (CHEBI:2376) has role EC 3.2.1.1 (α-amylase) inhibitor (CHEBI:50627)
acarbose (CHEBI:2376) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
acarbose (CHEBI:2376) has role geroprotector (CHEBI:176497)
acarbose (CHEBI:2376) has role hypoglycemic agent (CHEBI:35526)
acarbose (CHEBI:2376) is a tetrasaccharide derivative (CHEBI:63567)
acarbose (CHEBI:2376) is conjugate base of acarbose(1+) (CHEBI:84363)
Incoming Relation(s)
acarbose 7IV-phosphate (CHEBI:85517) has functional parent acarbose (CHEBI:2376)
acarbose(1+) (CHEBI:84363) is conjugate acid of acarbose (CHEBI:2376)
IUPAC Name 
4,6-dideoxy-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}-α-D-glucopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)-D-glucopyranose
INNs  Source
acarbosaWHO MedNet
acarboseWHO MedNet
acarboseWHO MedNet
acarbosumWHO MedNet
Synonym  Source
PrecoseChemIDplus
Brand Names  Source
GlucobayDrugBank
PrecoseDrugBank
Manual XrefsDatabases
38116ChemSpider
39DrugCentral
AcarboseWikipedia
C00016021KNApSAcK
C06802KEGG COMPOUND
D00216KEGG DRUG
DB00284DrugBank
DE2347782Patent
HMDB0014429HMDB
LSM-4345LINCS
US4062950Patent
Registry NumbersSources
CAS:56180-94-0KEGG COMPOUND
CAS:56180-94-0ChemIDplus
Citations