4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2H3)methyl-1,2-dihydropyrimidin-2-one

• ChemBase ID: 173509
• Molecular Formular: C10H15N3O4
• Molecular Mass: 241.2438
• Monoisotopic Mass: 241.10625598
• SMILES: [C@@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)nc(c(c1)C)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(C)c(nc1=O)N
• InChI: InChI=1S/C10H15N3O4/c1-5-3-13(10(16)12-9(5)11)8-2-6(15)7(4-14)17-8/h3,6-8,14-15H,2,4H2,1H3,(H2,11,12,16)/t6-,7+,8+/m0/s1
• InChIKey: LUCHPKXVUGJYGU-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methylpyrimidin-2-one
• Synonyms: 4-Amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(methyl-d3)-1H-pyrimidin-2-one; 2'-Deoxy-5-(methyl-d3)cytidine; 5-(Methyl-d3)deoxycytidine; 1-(2-Deoxy-β-D-ribofuranosyl)-5-(methyl-d3)cytosine; 5-Methyl-2'-deoxy Cytidine-d3

Database IDs

• CAS Number: 1160707-78-7
• PubChem SID: 164229419
• PubChem CID: 71750272

CALCULATED PROPERTIES

• Acid pKa: 13.894901
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5013329
• LogD (pH = 7.4): -1.501329
• Log P: -1.5013287
• Molar Refractivity: 57.3912 cm^3
• Polarizability: 22.602726 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 184-187°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M295902

A labelled Cytidine (C998300) analog and also an isostere of Thymidine (T412000).

REFERENCES

• Sabini, E., et al.: J. Med. Chem., 51, 4219 (2008)
• Sabini, E., et al.: J. Mol. Biol., 378, 607 (2008)