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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
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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 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

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 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

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
IUPAC Name Click here for help
(1R)-4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethylamino]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]-1-(fluoromethyl)cyclohex-3-ene-1-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
12083 fipravirimat
Synonyms Click here for help
compound 9 [PMID: 36044257] | GSK'254 | GSK-3640254 | GSK3640254
Database Links Click here for help
BindingDB Ligand 372346
CAS Registry No. 1818867-24-1 (source: WHO INN record)
GtoPdb PubChem SID 479821151
PubChem CID 118435805
Search Google for chemical match using the InChIKey YFSNREBZTKMFEB-DHGHKPCRSA-N
Search Google for chemicals with the same backbone YFSNREBZTKMFEB
Search PubMed clinical trials fipravirimat
Search PubMed titles fipravirimat
Search PubMed titles/abstracts fipravirimat
UniChem Compound Search for chemical match using the InChIKey YFSNREBZTKMFEB-DHGHKPCRSA-N
UniChem Connectivity Search for chemical match using the InChIKey YFSNREBZTKMFEB-DHGHKPCRSA-N