doravirine   Click here for help

GtoPdb Ligand ID: 12679

Synonyms: MK-1439 | MK1439 | Pifeltro®
Approved drug PDB Ligand
doravirine is an approved drug (FDA & EMA (2018))
Compound class: Synthetic organic
Comment: Doravirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) class antiretriviral drug.

doravirine is commercially available from our sponsors

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 8
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 98.03
Molecular weight 425.75
XLogP 1.73
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 CN1C(=NNC1=O)CN2C=CC(=C(C2=O)OC3=CC(=CC(=C3)C#N)Cl)C(F)(F)F
Isomeric SMILES CN1C(=NNC1=O)CN2C=CC(=C(C2=O)OC3=CC(=CC(=C3)C#N)Cl)C(F)(F)F
InChI InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)
InChI Key ZIAOVIPSKUPPQW-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 (2018))
Approved drug? Yes. EMA (2018)  |  FDA (2018)
IUPAC Name Click here for help
3-chloro-5-[1-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile
International Nonproprietary Names Click here for help
INN number INN
9797 doravirine
Synonyms Click here for help
MK-1439 | MK1439 | Pifeltro®
Database Links Click here for help
BindingDB Ligand 50508293
ChEMBL Ligand CHEMBL2364608
DrugBank Ligand DB12301
GtoPdb PubChem SID 483123227
PubChem CID 58460047
RCSB PDB Ligand 2KW
Search Google for chemical match using the InChIKey ZIAOVIPSKUPPQW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZIAOVIPSKUPPQW
Search PubMed clinical trials doravirine
Search PubMed titles doravirine
Search PubMed titles/abstracts doravirine
UniChem Compound Search for chemical match using the InChIKey ZIAOVIPSKUPPQW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZIAOVIPSKUPPQW-UHFFFAOYSA-N

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MedChemExpress
Doravirine (links to external site)
Cat. No. HY-16767