CHEBI:31897 - nateglinide

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ChEBI Name nateglinide
ChEBI ID CHEBI:31897
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H27NO3
Net Charge 0
Average Mass 317.42260
Monoisotopic Mass 317.199
InChI InChI=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
InChIKey OELFLUMRDSZNSF-BRWVUGGUSA-N
SMILES CC(C)[C@H]1CC[C@@H](CC1)C(=O)N[C@H](Cc1ccccc1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
nateglinida WHO MedNet
nateglinide WHO MedNet
natéglinide WHO MedNet
nateglinidum WHO MedNet
Synonyms Sources
(−)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine ChemIDplus
A 4166 ChemIDplus
A-4166 ChemIDplus
AY 4166 ChemIDplus
AY-4166 ChemIDplus
AY4166 ChemIDplus
trans-N-{[4-(1-methylethyl)cyclohexyl]carbonyl}-D-phenylalanine ChemIDplus
Brand Names Sources
Fastic ChemIDplus
Starlix ChemIDplus
Starsis KEGG DRUG
Manual Xrefs Databases
1886 DrugCentral
C12508 KEGG COMPOUND
D01111 KEGG DRUG
DB00731 DrugBank
EP196222 Patent
HMDB0014869 HMDB
Nateglinide Wikipedia
US4816484 Patent
View more database links
Registry Number Type Source
105816-04-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017