ainuovirine   Click here for help

GtoPdb Ligand ID: 13766

Synonyms: compound 10b [PMID: 20138513] | GS-9441 [3] | KM-023 | KM023
Approved drug PDB Ligand
ainuovirine is an approved drug
Compound class: Synthetic organic
Comment: Ainuovirine (KM-023) is a non-nucleoside reverse-transcriptase inhibitor (NNRTI) class antiretroviral that is intended to treat human immunodeficiency virus (HIV) type 1 infection [1-2].
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 1
Rotatable bonds 4
Topological polar surface area 90.27
Molecular weight 325.36
XLogP 1.36
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 CCN1C(=C(C(C)C)C(=O)NC1=O)C(=O)C2=CC(=CC(=C2)C)C#N
Isomeric SMILES CCN1C(=C(C(=O)NC1=O)C(C)C)C(=O)C2=CC(=CC(=C2)C#N)C
InChI InChI=1S/C18H19N3O3/c1-5-21-15(14(10(2)3)17(23)20-18(21)24)16(22)13-7-11(4)6-12(8-13)9-19/h6-8,10H,5H2,1-4H3,(H,20,23,24)
InChI Key AYPIJAMXGVYYRQ-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/)
References
1. Cha YJ, Lim KS, Park MK, Schneider S, Bray B, Kang MC, Chung JY, Yoon SH, Cho JY, Yu KS. (2014)
Pharmacokinetics and tolerability of the new second-generation nonnucleoside reverse- transcriptase inhibitor KM-023 in healthy subjects.
Drug Des Devel Ther, 8: 1613-9. [PMID:25302016]
2. Luo P, Jin J, Li J, Yin J, Jing X, Hou H, Ba H, Zhang Y. (2024)
A comparative study based on ainuovirine/lamivudine/tenofovir against HIV-1.
Int J STD AIDS, 35 (14): 1103-1111. [PMID:39269687]
3. Mitchell ML, Son JC, Guo H, Im YA, Cho EJ, Wang J, Hayes J, Wang M, Paul A, Lansdon EB et al.. (2010)
N1-Alkyl pyrimidinediones as non-nucleoside inhibitors of HIV-1 reverse transcriptase.
Bioorg Med Chem Lett, 20 (5): 1589-92. [PMID:20138513]