CHEBI:2376 - acarbose

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ChEBI Name acarbose
ChEBI ID CHEBI:2376
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40513
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Formula C25H43NO18
Net Charge 0
Average Mass 645.60480
Monoisotopic Mass 645.248
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
InChIKey XUFXOAAUWZOOIT-UGEKTDRHSA-N
SMILES C[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)OC(O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O
Roles Classification
Biological Role(s): EC 3.2.1.20 (alpha-glucosidase) inhibitor
An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-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 alpha-amylase (EC 3.2.1.1).
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 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 Sources
acarbosa ChemIDplus
acarbose ChEBI
acarbosum ChemIDplus
Synonyms Sources
Acarbose KEGG COMPOUND
Precose ChemIDplus
Brand Names Sources
Glucobay DrugBank
Precose DrugBank
Database Links Databases
39 DrugCentral
Acarbose Wikipedia
C00016021 KNApSAcK
C06802 KEGG COMPOUND
D00216 KEGG DRUG
DB00284 DrugBank
DE2347782 Patent
HMDB0014429 HMDB
LSM-4345 LINCS
US4062950 Patent
View more database links
Registry Number Type Source
56180-94-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11937512 PubMed citation Europe PMC
18248270 PubMed citation Europe PMC
25044702 PubMed citation Europe PMC
8893066 PubMed citation Europe PMC
9805641 PubMed citation Europe PMC
Last Modified
22 February 2017