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CHEBI:31897 - nateglinide

ChEBI IDCHEBI:31897
ChEBI Namenateglinide
Stars
DefinitionAn N-acyl-D-phenylalanine resulting from the formal condensation of the amino group of D-phenylalanine with the carboxy group of trans-4-isopropylcyclohexanecarboxylic acid. An orally-administered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus.
Last Modified22 February 2017
DownloadsMolfile
FormulaC19H27NO3
Net Charge0
Average Mass317.429
Monoisotopic Mass317.19909
SMILESCC(C)[C@H]1CC[C@H](C(=O)N[C@H](Cc2ccccc2)C(=O)O)CC1
InChIInChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
InChIKeyOELFLUMRDSZNSF-BRWVUGGUSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor  An EC 3.4.14.* (dipeptidyl- and tripeptidyl-peptidases) inhibitor that specifically inhibits dipeptidyl peptidase-4 (EC 3.4.14.5).
Application:
hypoglycemic agent  A drug which lowers the blood glucose level.
ChEBI Ontology
Outgoing Relation(s)
nateglinide (CHEBI:31897) has role EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor (CHEBI:68612)
nateglinide (CHEBI:31897) has role hypoglycemic agent (CHEBI:35526)
nateglinide (CHEBI:31897) is a N-acyl-D-phenylalanine (CHEBI:77672)
IUPAC Name 
N-[(trans-4-isopropylcyclohexyl)carbonyl]-D-phenylalanine
INNs  Source
nateglinidumWHO MedNet
natéglinideWHO MedNet
nateglinideWHO MedNet
nateglinidaWHO MedNet
Synonyms  Source
(−)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanineChemIDplus
A 4166ChemIDplus
AY-4166ChemIDplus
AY 4166ChemIDplus
A-4166ChemIDplus
AY4166ChemIDplus
Brand Names  Source
FasticChemIDplus
StarlixChemIDplus
StarsisKEGG DRUG
Manual XrefsDatabases
C12508KEGG COMPOUND
D01111KEGG DRUG
EP196222Patent
US4816484Patent
NateglinideWikipedia
DB00731DrugBank
HMDB0014869HMDB
1886DrugCentral
Registry NumbersSources
CAS:105816-04-4KEGG COMPOUND
CAS:105816-04-4ChemIDplus
Citations