Monastrol

Monastrol

Names
IUPAC name ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
Other names Monastrol
Identifiers
CAS Number	329689-23-8^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75382^Y
ChEMBL	ChEMBL236789^Y
ChemSpider	2259791^Y
PubChem CID	2987927
CompTox Dashboard (EPA)	DTXSID501317756 DTXSID10388124, DTXSID501317756
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)^N Key: LOBCDGHHHHGHFA-UHFFFAOYSA-N^Y InChI=1/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) Key: LOBCDGHHHHGHFA-UHFFFAOYAO
SMILES CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
Properties
Chemical formula	C14H16N2O3S
Molar mass	292.35344
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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.^[1]

Mechanism of action

Monastrol inhibits Eg5

Monastrol binds to a long loop that is specific to the Eg5 (also known as KIF11 or kinesin-5) kinesin family, and allosterically inhibits ATPase activity of the kinesin ^[2]

References

1. Thomas U. Mayer; Tarun M. Kapoor; Stephen J. Haggarty; Randall W. King; Stuart L. Schreiber; Timothy J. Mitchison (1999). "Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen". Science. 286 (5441): 971–974. doi:10.1126/science.286.5441.971. PMID 10542155. S2CID 15348455.
2. Maliga Z, Kapoor TM, Mitchison TJ (September 2002). "Evidence that monastrol is an allosteric inhibitor of the mitotic kinesin Eg5". Chem. Biol. 9 (9): 989–96. doi:10.1016/S1074-5521(02)00212-0. PMID 12323373.