acetylcysteine   Click here for help

GtoPdb Ligand ID: 10945

Synonyms: Ilube® (eye drops) | N-A-C Sustain® | N-Acetyl-cysteine | N-Acetyl-L-cysteine | NAC | Parvolex®
Approved drug PDB Ligand
acetylcysteine is an approved drug (FDA (1963), UK (1992))
Compound class: Synthetic organic
Comment: Acetylcysteine is a prodrug for L-cysteine synthesis, and L-cysteine is a precursor to the biologic antioxidant glutathione. Hence adminstration of acetylcysteine replenishes glutathione stores.

acetylcysteine is commercially available from our sponsors

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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 105.2
Molecular weight 163.03
XLogP -0.13
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 SC[C@@H](C(=O)O)NC(=O)C
Isomeric SMILES SC[C@@H](C(=O)O)NC(=O)C
InChI InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
InChI Key PWKSKIMOESPYIA-BYPYZUCNSA-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
Approved drug? Yes. FDA (1963)  |  UK (1992)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2R)-2-acetamido-3-sulfanylpropanoic acid
International Nonproprietary Names Click here for help
INN number INN
1535 acetylcysteine
Synonyms Click here for help
Ilube® (eye drops) | N-A-C Sustain® | N-Acetyl-cysteine | N-Acetyl-L-cysteine | NAC | Parvolex®
Database Links Click here for help
BindingDB Ligand 50420190
CAS Registry No. 616-91-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL600
DrugBank Ligand DB06151
DrugCentral Ligand 66
GtoPdb PubChem SID 405560386
PubChem CID 12035
RCSB PDB Ligand 1ZT, SC2
Search Google for chemical match using the InChIKey PWKSKIMOESPYIA-BYPYZUCNSA-N
Search Google for chemicals with the same backbone PWKSKIMOESPYIA
Search PubMed clinical trials acetylcysteine
Search PubMed titles acetylcysteine
Search PubMed titles/abstracts acetylcysteine
UniChem Compound Search for chemical match using the InChIKey PWKSKIMOESPYIA-BYPYZUCNSA-N
UniChem Connectivity Search for chemical match using the InChIKey PWKSKIMOESPYIA-BYPYZUCNSA-N

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MedChemExpress
Acetylcysteine (links to external site)
Cat. No. HY-B0215