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;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75382;
ChEMBL	ChEMBL236789;
ChemSpider	2259791;
PubChemCID	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) Key: LOBCDGHHHHGHFA-UHFFFAOYSA-N; 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 theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

Monastrolis a cell-permeable small molecule inhibitor discovered by Thomas U. Mayer in the lab ofTim Mitchison.Monastrol was shown to inhibit thekinesin-5 (also known asKIF11,Kinesin Eg5), amotor proteinimportant for spindle bipolarity.^[1]

Mechanism of action

Monastrol inhibits Eg5

Monastrol binds to a long loop that is specific to the Eg5 (also known asKIF11or kinesin-5) kinesin family, and allosterically inhibits ATPase activity of the kinesin^[2]

References

^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.
^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.

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[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.

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