(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (2R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylate

• ChemBase ID: 172582
• Molecular Formular: C18H27N3O4S
• Molecular Mass: 384.46915263
• Monoisotopic Mass: 384.16965198
• SMILES: [15n]1([C@@H]2CS[C@@H](O2)C(=O)O[C@@H]2C[C@@H](CC[C@H]2C(C)C)C)ccc([15n][13c]1=O)N
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)[C@H]1SC[C@H](O1)[15n]1ccc([15n][13c]1=O)N)C(C)C
• InChI: InChI=1S/C18H27N3O4S/c1-10(2)12-5-4-11(3)8-13(12)24-16(22)17-25-15(9-26-17)21-7-6-14(19)20-18(21)23/h6-7,10-13,15,17H,4-5,8-9H2,1-3H3,(H2,19,20,23)/t11-,12+,13-,15+,17-/m1/s1/i18+1,20+1,21+1
• InChIKey: QMYKWNYBSBURDT-MZVQIDIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl (2R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylate
• IUPAC Traditional name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[4-amino-2-oxo(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-1,3-oxathiolane-2-carboxylate
• Synonyms: (2R,5S)-5-(4-Amino-2-oxo-1(2H)-pyrimidinyl15N2,13C)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester; (2R,5S)-L-Menthol-5-(4-amino-2-oxo-1(2H)-pyrimidinyl-15N2,13C)-1,3-oxathiolane-2-carboxylate

Database IDs

• PubChem SID: 164228492
• PubChem CID: 46782119

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.55391
• LogD (pH = 7.4): 2.5539112
• Log P: 2.5539112
• Molar Refractivity: 98.985 cm^3
• Polarizability: 39.11538 Å^3
• Polar Surface Area: 94.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Tan Solid

DETAILS

Toronto Research Chemicals - M219022

Labelled Lamivudine intermediate.

REFERENCES

• Chang, C., et al.: J. Biol. Chem., 267, 13938 (1992)
• Jeong, L., et al.: J. Med. Chem., 36, 181 (1993).