brincidofovir   Click here for help

GtoPdb Ligand ID: 11556

Synonyms: CMX-001 | CMX001 | HDP-CDV | hexadecyloxypropyl cidofovir | Tembexa®
Approved drug
brincidofovir is an approved drug (FDA (2021))
Compound class: Synthetic organic
Comment: Brincidofovir is an orally bioavailable, lipid-conjugated (to enhance cellular penetration) ester prodrug of the acyclic nucleoside monophosphate antiviral cidofovir. The active metabolite is cidofovir diphosphate, which disrupts viral DNA polymerase activity and viral DNA replication. Brincidofovir has been investigated for infections caused by several virus families, including cytomegalovirus (CMV), BK virus (BKV), adenoviruses (AdV) [1], HPV [4], and Epstein-Barr virus (EBV), as well as for smallpox (Variola) infections.
A molecular docking study has indicated that brincidofovir interacts with both host ACE2 and SARS-CoV-2 3C-like (main) protease [2]. Further studies would be required to validate brincidofovir as a potential therapy for SARS-CoV-2 infection.
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 CDK toolkit. 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 3
Rotatable bonds 26
Topological polar surface area 155.94
Molecular weight 561.35
XLogP 7.01
No. Lipinski's rules broken 2
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.

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Canonical SMILES CCCCCCCCCCCCCCCCOCCCOP(=O)(CO[C@@H](Cn1ccc(nc1=O)N)CO)O
Isomeric SMILES CCCCCCCCCCCCCCCCOCCCOP(=O)(CO[C@@H](Cn1ccc(nc1=O)N)CO)O
InChI InChI=1S/C27H52N3O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32)/t25-/m0/s1
InChI Key WXJFKKQWPMNTIM-VWLOTQADSA-N
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel