ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• ChemBase ID: 155116
• Molecular Formular: C14H16N2O3S
• Molecular Mass: 292.35344
• Monoisotopic Mass: 292.08816338
• SMILES: CCOC(=O)C1=C(NC(=S)NC1c1cccc(c1)O)C
• Canonical SMILES: CCOC(=O)C1=C(C)NC(=S)NC1c1cccc(c1)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• IUPAC Traditional name: monastrol; ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• Synonyms: 4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic Acid Ethyl Ester; Monastrol; 6-Methyl-4-(3-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate; Monastrol

Database IDs

• CAS Number: 254753-54-3; 254753-54-3
• MDL Number: MFCD00813077
• PubChem SID: 24897267; 162249254
• PubChem CID: 2987927

CALCULATED PROPERTIES

• Acid pKa: 9.374903
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 1.8265492
• LogD (pH = 7.4): 1.8220707
• Log P: 1.8266066
• Molar Refractivity: 81.4057 cm^3
• Polarizability: 31.166754 Å^3
• Polar Surface Area: 70.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >5 mg/mL; Ethanol; Ethyl Acetate
• Apperance: White Solid; white to off-white solid
• Melting Point: 184-186°C; 185-185.9 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer; protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Selective inhibitor of mitotic kinesin Eg5

Product Information

• Purity: ≥98% (HPLC)
• Application(s): Antineoplastic agent
• Empirical Formula (Hill Notation): C14H16N2O3S

DETAILS

Sigma Aldrich - M8515

Packaging
Packaged under inert gas.
Biochem/physiol Actions
Monastrol is a potent, cell-permeant inhibitor of mitosis. Monastrol arrested cells are characterized by monopolar spindles. This phenotype is induced through specific disruption of mitotic molecular motor kinesin Eg5 with IC50 at 14 μM. No effect on other motor proteins and tubulin.

Toronto Research Chemicals - M505750

A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles.

REFERENCES

• Mayer, T.U., et al.: Science, 286, 971 (1999)
• Kappe, C.O., et al.: Tetrahedron, 56, 1859 (2000)
• Mayeret al (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286 971.