tipiracil   Click here for help

GtoPdb Ligand ID: 8696

Synonyms: MA-1 | TAS-1-462
Approved drug
tipiracil is an approved drug (Japan only)
Compound class: Synthetic organic
Comment: Tipracil is a a uracil derivative that inhibits thymidine phosphorylase (TYMP, P19971; a.k.a. platelet-derived endothelial cell growth factor), an enzyme which metabolises trifluridine.
TAS-102 contains tipracil as the hydrochloride salt (PubChem CID 9903778).

SARS-CoV-2: Tipracil has been shown to bind to the uridine-specific endoribonuclease Nsp15 of SARS-CoV-2, and this interaction inhibits the enzyme's uridine-degrading catalytic activity [1].

tipiracil 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 3
Rotatable bonds 2
Topological polar surface area 92.81
Molecular weight 242.06
XLogP 1.26
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 O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
Isomeric SMILES O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
InChI InChI=1S/C9H11ClN4O2/c10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11/h11H,1-4H2,(H2,12,13,15,16)
InChI Key QQHMKNYGKVVGCZ-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Japan (0)
IUPAC Name Click here for help
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-1H-pyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
9500 tipiracil
Synonyms Click here for help
MA-1 | TAS-1-462
Database Links Click here for help
CAS Registry No. 183204-74-2 (source: PubChem)
ChEMBL Ligand CHEMBL235668
DrugBank Ligand DB02631
DrugCentral Ligand 4893
GtoPdb PubChem SID 252166896
PubChem CID 6323266
Search Google for chemical match using the InChIKey QQHMKNYGKVVGCZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QQHMKNYGKVVGCZ
Search PubMed clinical trials tipiracil
Search PubMed titles tipiracil
Search PubMed titles/abstracts tipiracil
UniChem Compound Search for chemical match using the InChIKey QQHMKNYGKVVGCZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QQHMKNYGKVVGCZ-UHFFFAOYSA-N
Wikipedia Tipiracil

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MedChemExpress
Tipiracil (links to external site)
Cat. No. HY-A0063A