bis(4-amino-1-[(2R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ4-oxathiolan-5-yl]-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-2-one)

• ChemBase ID: 172183
• Molecular Formular: C16H22N6O8S2
• Molecular Mass: 496.47022527
• Monoisotopic Mass: 496.08890294
• SMILES: [S@]1(=O)C[C@H](O[C@H]1CO)[15n]1[13c](=O)[15n]c(cc1)N.[S@@]1(=O)C[C@H](O[C@H]1CO)[15n]1[13c](=O)[15n]c(cc1)N
• Canonical SMILES: OC[C@@H]1O[C@@H](C[S@@]1=O)[15n]1ccc([15n][13c]1=O)N.OC[C@@H]1O[C@@H](C[S@]1=O)[15n]1ccc([15n][13c]1=O)N
• InChI: InChI=1S/2C8H11N3O4S/c2*9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h2*1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16+;6-,7+,16-/m00/s1/i2*8+1,10+1,11+1
• InChIKey: NOSJQYBDXRFOBQ-KIVDYYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(4-amino-1-[(2R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ^4-oxathiolan-5-yl]-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one)
• IUPAC Traditional name: 4-amino-1-[(2R,3R,5S)-2-(hydroxymethyl)-3-oxo-1,3λ^4-oxathiolan-5-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one; 4-amino-1-[(2R,3S,5S)-2-(hydroxymethyl)-3-oxo-1,3λ^4-oxathiolan-5-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• Synonyms: 4-Amino-1-[(2R,3RS,5S)-2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone-13C,15N2; [2R-(2α,3αβ,5α)]-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone S-Oxide-13C,15N2; [2R-(2α,3αβ,5α)]-4-Amino-1-[2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone-13C,15N; Lamivudine-13C,15N2 S-Oxide (Mixture of Diastereomers)

Database IDs

• PubChem SID: 164228093
• PubChem CID: 71749729

CALCULATED PROPERTIES

• Acid pKa: 14.010272
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.4702654
• LogD (pH = 7.4): -2.4702644
• Log P: -2.4702642
• Molar Refractivity: 56.1226 cm^3
• Polarizability: 21.97182 Å^3
• Polar Surface Area: 105.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L172532

A labelled metabolite of Lamivudine (L172500).

REFERENCES

• Takubo, T. et al.: Yakub. Dotai, 12, 102 (1997)