nateglinide   Click here for help

GtoPdb Ligand ID: 6833

Synonyms: AY-4166 | SDZ-DJN-608 | Starlix®
Approved drug
nateglinide is an approved drug (FDA (2000), EMA (2001))
Compound class: Synthetic organic
Comment: A sulfonylurea receptor 1, Kir6.2 blocker, but belonging to the metiglinides drug family. Note that the PubChem CID listed here is a slightly different isomer to the ChEMBL ligand and the INN structure.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nateglinide

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 66.4
Molecular weight 317.2
XLogP 4.56
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC(C1CCC(CC1)C(=O)NC(C(=O)O)Cc1ccccc1)C
Isomeric SMILES CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O)Cc1ccccc1)C
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
InChI Key OELFLUMRDSZNSF-BRWVUGGUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2000), EMA (2001))
IUPAC Name Click here for help
(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
International Nonproprietary Names Click here for help
INN number INN
7594 nateglinide
Synonyms Click here for help
AY-4166 | SDZ-DJN-608 | Starlix®
Database Links Click here for help
CAS Registry No. 105816-04-4
ChEMBL Ligand CHEMBL783
DrugBank Ligand DB00731
DrugCentral Ligand 1886
GtoPdb PubChem SID 178103439
PubChem CID 5311309
Search Google for chemical match using the InChIKey OELFLUMRDSZNSF-BRWVUGGUSA-N
Search Google for chemicals with the same backbone OELFLUMRDSZNSF
Search PubMed clinical trials nateglinide
Search PubMed titles nateglinide
Search PubMed titles/abstracts nateglinide
UniChem Compound Search for chemical match using the InChIKey OELFLUMRDSZNSF-BRWVUGGUSA-N
UniChem Connectivity Search for chemical match using the InChIKey OELFLUMRDSZNSF-BRWVUGGUSA-N
Wikipedia Nateglinide