4-amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-2-one

• ChemBase ID: 168057
• Molecular Formular: C8H11N3O3S
• Molecular Mass: 232.23571263
• Monoisotopic Mass: 232.04953685
• SMILES: S1C[C@@H](O[C@H]1CO)[15n]1[13c](=O)[15n]c(cc1)N
• Canonical SMILES: Nc1cc[15n]([13c](=O)[15n]1)[C@H]1CS[C@@H](O1)CO
• InChI: InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1/i8+1,10+1,11+1
• InChIKey: JTEGQNOMFQHVDC-PNZYAHHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• Synonyms: (2R-trans)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone-15N2,13C; 4-Amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone-15N2,13C; 5'-Epi Lamivudine-15N2,13C

Database IDs

• PubChem SID: 162262189
• PubChem CID: 71316357

CALCULATED PROPERTIES

• Acid pKa: 14.294606
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0951098
• LogD (pH = 7.4): -1.0951077
• Log P: -1.0951076
• Molar Refractivity: 55.1645 cm^3
• Polarizability: 21.351086 Å^3
• Polar Surface Area: 88.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E588527

Labelled Lamivudine epimer.

REFERENCES

• Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992)
• Jeong, L., et al.: J. Med. Chem., 36, 181 (1992)