1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 72661
• Molecular Formular: C10H12N2O4
• Molecular Mass: 224.21328
• Monoisotopic Mass: 224.07970687
• SMILES: O1C(C=CC1CO)n1c(=O)[nH]c(=O)c(c1)C
• Canonical SMILES: Cc1cn(C2OC(C=C2)CO)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)
• InChIKey: XNKLLVCARDGLGL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: Zerit; Stavudine

Database IDs

• CAS Number: 3056-17-5
• PubChem SID: 162037586
• PubChem CID: 5155

CALCULATED PROPERTIES

• Acid pKa: 9.952853
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.23182122
• LogD (pH = 7.4): -0.23300652
• Log P: -0.2318061
• Molar Refractivity: 55.3163 cm^3
• Polarizability: 21.057823 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Reverse transcriptase

Product Information

• Salt Data: Free Base
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Selleck Chemicals - S1398

Research Area: Infection
Biological Activity:
Stavudine is a nucleoside analog reverse transcriptase inhibitor (NARTI) active against HIV. Stavudine is an analog of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Stavudine