etomidate   Click here for help

GtoPdb Ligand ID: 5463

Synonyms: Amidate® | D-etomidate | R 16659
Approved drug PDB Ligand
etomidate is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Etomidate is a hypnotic agent. Note that we represent the exact chemical structure of the compound as submitted with its INN record.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: etomidate

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 3
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 44.12
Molecular weight 244.12
XLogP 2.87
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 CCOC(=O)c1cncn1C(c1ccccc1)C
Isomeric SMILES CCOC(=O)c1cncn1[C@@H](c1ccccc1)C
InChI InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1
InChI Key NPUKDXXFDDZOKR-LLVKDONJSA-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 (1982))
IUPAC Name Click here for help
ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate
International Nonproprietary Names Click here for help
INN number INN
1926 etomidate
Synonyms Click here for help
Amidate® | D-etomidate | R 16659
Database Links Click here for help
CAS Registry No. 33125-97-2
ChEBI CHEBI:4910
ChEMBL Ligand CHEMBL681
DrugBank Ligand DB00292
DrugCentral Ligand 1109
GtoPdb PubChem SID 178102113
PubChem CID 667484
RCSB PDB Ligand V8D
Search Google for chemical match using the InChIKey NPUKDXXFDDZOKR-LLVKDONJSA-N
Search Google for chemicals with the same backbone NPUKDXXFDDZOKR
Search PubMed clinical trials etomidate
Search PubMed titles etomidate
Search PubMed titles/abstracts etomidate
UniChem Compound Search for chemical match using the InChIKey NPUKDXXFDDZOKR-LLVKDONJSA-N
UniChem Connectivity Search for chemical match using the InChIKey NPUKDXXFDDZOKR-LLVKDONJSA-N
Wikipedia Etomidate