etravirine   Click here for help

GtoPdb Ligand ID: 12675

Synonyms: Intelence® | R-165335 | R165335 | TMC-125 | TMC125
Approved drug PDB Ligand
etravirine is an approved drug (FDA & EMA (2008))
Compound class: Synthetic organic
Comment: Etravirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) class antiretriviral drug.
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 119.58
Molecular weight 435.28
XLogP 0.9
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
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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/)

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Canonical SMILES CC1=C(C(=CC(=C1)C#N)C)OC2=C(C(=NC(=N2)NC3=CC=C(C=C3)C#N)N)Br
Isomeric SMILES CC1=CC(=CC(=C1OC2=NC(=NC(=C2Br)N)NC3=CC=C(C=C3)C#N)C)C#N
InChI InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
InChI Key PYGWGZALEOIKDF-UHFFFAOYSA-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 & EMA (2008))
IUPAC Name Click here for help
4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile
International Nonproprietary Names Click here for help
INN number INN
8303 etravirine
Synonyms Click here for help
Intelence® | R-165335 | R165335 | TMC-125 | TMC125
Database Links Click here for help
BindingDB Ligand 50103642
ChEBI CHEBI:63589
ChEMBL Ligand CHEMBL308954
DrugBank Ligand DB06414
GtoPdb PubChem SID 483123223
PubChem CID 193962
RCSB PDB Ligand 65B
Search Google for chemical match using the InChIKey PYGWGZALEOIKDF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PYGWGZALEOIKDF
Search PubMed clinical trials etravirine
Search PubMed titles etravirine
Search PubMed titles/abstracts etravirine
UniChem Compound Search for chemical match using the InChIKey PYGWGZALEOIKDF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PYGWGZALEOIKDF-UHFFFAOYSA-N