Monastrol - ≥98% , CAS No.329689-23-8

CAS: 329689-23-8 Cat. No.: M274759 Molecular Weight: 292.35

GRADE & PURITY ≥98%

Synonyms

1,2,3,4-Tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-5-pyrimidinecarboxylicacidethylester | (±)-Monastrol | 6-Methyl-4-(3-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. It is important to note that this product is reported to be light sensitive. Store In the Dark. Store under desiccating conditions.

Specifications

Synonyms

1, 2, 3, 4-Tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-5-pyrimidinecarboxylicacidethylester | (±)-Monastrol | 6-Methyl-4-(3-hydroxyphenyl)-2-thioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Potent and cell permeable mitosis inhibitor. Arrests cellular mitosis through kinesin Eg5 inhibition (IC 50 = 14 μM). Also slows ADP release, changes Eg5 conformation and alters Eg5 interactions with microtubules.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488194127
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194127
• Canonical Smiles: CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
• IUPAC Name: ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• InChIKey: LOBCDGHHHHGHFA-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
• Molecular Weight: 292.35
• Reaxy-Rn: 8495831
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8495831&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives
        • Level5 Hydropyrimidines
          • Level6 Hydropyrimidine carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Hydropyrimidines
• Direct Parent: Hydropyrimidine carboxylic acids and derivatives
• Alternative Parents: Pyrimidinethiones 2-Thiopyrimidines 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous amides Enoate esters Thioureas Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hydropyrimidine carboxylic acid derivative - 2-thiopyrimidine - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Thiopyrimidine - Phenol - Pyrimidinethione - Monocyclic benzene moiety - Benzenoid - Vinylogous amide - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Thiourea - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hydropyrimidine carboxylic acids and derivatives. These are compounds containing a hydrogenated pyrimidine ring which bears a carboxylic acid group.
• External Descriptors: ethyl ester - phenols - thioureas - enoate ester

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP3A4 Tclin Cytochrome P450 3A4 (1 Activities)

Discover Target: CYP3A4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 100 mM and in ethanol to 100 mM
• Sensitivity: light sensitive
• Molecular Weight: 292.360 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 292.088 Da
• Monoisotopic Mass: 292.088 Da
• Topological Polar Surface Area: 103.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 436.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1