CHEBI:75382 - monastrol

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ChEBI Name monastrol
ChEBI ID CHEBI:75382
Definition A racemate comprising equimolar amounts of R- and S-monastrol.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5268052, eMolecules:486062, eMolecules:30487811, Selleckchem:2-Methoxyestradiol(2ME2), ZINC000003818826
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Monastrol is a cell-permeable small molecule inhibitor discovered by Thomas U. Mayer in the lab of Tim Mitchison. Monastrol was shown to inhibit the kinesin-5 (also known as KIF11, Kinesin Eg5), a motor protein important for spindle bipolarity.
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Formula C14H16N2O3S
Net Charge 0
Average Mass 292.35300
Monoisotopic Mass 292.08816
InChI InChI=1S/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)
InChIKey LOBCDGHHHHGHFA-UHFFFAOYSA-N
SMILES CCOC(=O)C1=C(C)NC(=S)NC1c1cccc(O)c1
Roles Classification
Biological Role(s): EC 3.5.1.5 (urease) inhibitor
EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the activity of urease (EC 3.5.1.5), reducing hydrolysis.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antimitotic
Any compound that inhibits cell division (mitosis).
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing monastrol (CHEBI:75382) has part (R)-monastrol (CHEBI:75383)
monastrol (CHEBI:75382) has part (S)-monastrol (CHEBI:75384)
monastrol (CHEBI:75382) has role antileishmanial agent (CHEBI:70868)
monastrol (CHEBI:75382) has role antimitotic (CHEBI:64911)
monastrol (CHEBI:75382) has role antineoplastic agent (CHEBI:35610)
monastrol (CHEBI:75382) has role EC 3.5.1.5 (urease) inhibitor (CHEBI:50635)
monastrol (CHEBI:75382) is a racemate (CHEBI:60911)
IUPAC Name
rac-ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Manual Xrefs Databases
CN101781259 Patent
LSM-1809 LINCS
Monastrol Wikipedia
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Registry Number Type Source
8495831 Reaxys Registry Number Reaxys
Citations Types Sources
20519355 PubMed citation Europe PMC
23292345 PubMed citation Europe PMC
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27592117 PubMed citation Europe PMC
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30015883 PubMed citation Europe PMC
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Last Modified
25 April 2019