fipravirimat   Click here for help

GtoPdb Ligand ID: 12360

Synonyms: compound 9 [PMID: 36044257] | GSK'254 | GSK-3640254 | GSK3640254
Compound class: Synthetic organic
Comment: Fipravirimat (GSK3640254) is an investigational HIV-1 maturation inhibitor (MI) [1]. MIs disrupt the processing of the HIV Gag polyprotein, and this action interferes with the formation of mature, infectious virus particles. Fipravirimat retains activity against HIV-1 with known resistance mutations.
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 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 95.09
Molecular weight 726.48
XLogP 11.1
No. Lipinski's rules broken 1
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.

✖
Canonical SMILES FC[C@@]1(CCC(=CC1)C1=CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)NCCN1CCS(=O)(=O)CC1)C)C)C(=O)O
Isomeric SMILES CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@]([C@@]1(CC2)C)(CC[C@@H]1[C@@]3(CC=C(C1(C)C)C1=CC[C@@](CC1)(CF)C(=O)O)C)C)NCCN1CCS(=O)(=O)CC1
InChI InChI=1S/C43H67FN2O4S/c1-29(2)31-12-19-43(45-22-23-46-24-26-51(49,50)27-25-46)21-20-40(6)33(36(31)43)8-9-35-39(5)15-13-32(38(3,4)34(39)14-16-41(35,40)7)30-10-17-42(28-44,18-11-30)37(47)48/h10,13,31,33-36,45H,1,8-9,11-12,14-28H2,2-7H3,(H,47,48)/t31-,33+,34-,35+,36+,39-,40+,41+,42+,43-/m0/s1
InChI Key YFSNREBZTKMFEB-DHGHKPCRSA-N
References
1. Regueiro-Ren A, Sit SY, Chen Y, Chen J, Swidorski JJ, Liu Z, Venables BL, Sin N, Hartz RA, Protack T et al.. (2022)
The Discovery of GSK3640254, a Next-Generation Inhibitor of HIV-1 Maturation.
J Med Chem, 65 (18): 11927-11948. [PMID:36044257]
2. Spinner CD, Felizarta F, Rizzardini G, Philibert P, Mitha E, Domingo P, Stephan CJ, DeGrosky M, Bainbridge V, Zhan J et al.. (2022)
Phase IIa Proof-of-Concept Evaluation of the Antiviral Efficacy, Safety, Tolerability, and Pharmacokinetics of the Next-Generation Maturation Inhibitor GSK3640254.
Clin Infect Dis, 75 (5): 786-794. [PMID:34996113]