lenacapavir   Click here for help

GtoPdb Ligand ID: 11446

Synonyms: GS-6207 | GS6207 | Sunlenca®
Approved drug PDB Ligand
lenacapavir is an approved drug (EMA & FDA (2022))
Compound class: Synthetic organic
Comment: Lenacapavir (GS-6207) is a novel long-acting anti-HIV lead that binds to the virus' at a conserved interface between capsid protein monomers [2]. This mechanism disrupts early and late phases of the viral replication cycle [1] [3]. PDB entry 6V2F shows the crystal structure of lenacapavir-bound HIV capsid hexamer.
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 10
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 174.7
Molecular weight 967.14
XLogP 8.17
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 O=C(Cn1nc(c2c1C(F)(F)[C@H]1[C@@H]2C1)C(F)(F)F)N[C@H](c1nc(C#CC(S(=O)(=O)C)(C)C)ccc1c1ccc(c2c1n(nc2NS(=O)(=O)C)CC(F)(F)F)Cl)Cc1cc(F)cc(c1)F
Isomeric SMILES O=C(Cn1nc(c2c1C(F)(F)[C@H]1[C@@H]2C1)C(F)(F)F)N[C@H](c1nc(C#CC(S(=O)(=O)C)(C)C)ccc1c1ccc(c2c1n(nc2NS(=O)(=O)C)CC(F)(F)F)Cl)Cc1cc(F)cc(c1)F
InChI InChI=1S/C39H32ClF10N7O5S2/c1-36(2,63(3,59)60)10-9-21-5-6-22(23-7-8-26(40)30-32(23)57(17-37(43,44)45)54-35(30)55-64(4,61)62)31(51-21)27(13-18-11-19(41)14-20(42)12-18)52-28(58)16-56-34-29(33(53-56)39(48,49)50)24-15-25(24)38(34,46)47/h5-8,11-12,14,24-25,27H,13,15-17H2,1-4H3,(H,52,58)(H,54,55)/t24-,25+,27-/m0/s1
InChI Key BRYXUCLEHAUSDY-WEWMWRJBSA-N
References
1. Freed EO. (2015)
HIV-1 assembly, release and maturation.
Nat Rev Microbiol, 13 (8): 484-96. [PMID:26119571]
2. Link JO, Rhee MS, Tse WC, Zheng J, Somoza JR, Rowe W, Begley R, Chiu A, Mulato A, Hansen D et al.. (2020)
Clinical targeting of HIV capsid protein with a long-acting small molecule.
Nature, 584 (7822): 614-618. [PMID:32612233]
3. Thenin-Houssier S, Valente ST. (2016)
HIV-1 Capsid Inhibitors as Antiretroviral Agents.
Curr HIV Res, 14 (3): 270-82. [PMID:26957201]