1-[5-(aminomethyl)-4-hydroxyoxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 132631
• Molecular Formular: C10H15N3O4
• Molecular Mass: 241.2438
• Monoisotopic Mass: 241.10625598
• SMILES: Cc1cn(c(=O)[nH]c1=O)C1CC(C(O1)CN)O
• Canonical SMILES: NCC1OC(CC1O)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H15N3O4/c1-5-4-13(10(16)12-9(5)15)8-2-6(14)7(3-11)17-8/h4,6-8,14H,2-3,11H2,1H3,(H,12,15,16)
• InChIKey: PYWLBQPICCQJFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[5-(aminomethyl)-4-hydroxyoxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: thymidine, 5'-amino-5'-deoxy-
• Synonyms: 5′-Amino-5′-deoxythymidine

Database IDs

• CAS Number: 25152-20-9
• MDL Number: MFCD00047488
• PubChem SID: 162226908; 24890985
• PubChem CID: 297924

CALCULATED PROPERTIES

• Acid pKa: 10.016496
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.1549835
• LogD (pH = 7.4): -2.9158962
• Log P: -1.5926437
• Molar Refractivity: 57.0695 cm^3
• Polarizability: 22.836971 Å^3
• Polar Surface Area: 104.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

DETAILS

Sigma Aldrich - A5525

Application
5′-Amino-5′-deoxythymidine may be used as a substrate in the synthesis of amide-conjugated nucleosides and their analogues. 5′-Amino-5′-deoxythymidine may be used for DNA 5′-terminal site-specific modification. 5′-Amino-5′-deoxythymidine is used to produce modified thymidine dimer oligonucleotide building units (squaryl groups) to create new oligonucleotide analogues.