methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}oxane-2-carboxylate

• ChemBase ID: 161009
• Molecular Formular: C23H29N5O13
• Molecular Mass: 583.50206
• Monoisotopic Mass: 583.17618601
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1C[C@@H]([C@H](O1)CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)N=[N+]=[N-])C
• Canonical SMILES: [N-]=[N+]=N[C@H]1C[C@@H](O[C@@H]1CO[C@@H]1O[C@@H](C(=O)OC)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C23H29N5O13/c1-9-7-28(23(34)25-20(9)32)15-6-13(26-27-24)14(40-15)8-36-22-19(39-12(4)31)17(38-11(3)30)16(37-10(2)29)18(41-22)21(33)35-5/h7,13-19,22H,6,8H2,1-5H3,(H,25,32,34)/t13-,14+,15+,16-,17-,18-,19+,22+/m0/s1
• InChIKey: UFPYHKZYJWKNOT-JDWKTYAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxy}oxane-2-carboxylate
• Synonyms: AZT 2,3,4-Tri-O-acetyl-β-D-glucuronide, Methyl Ester; 3'-Azido-3'-deoxythymidine 2,3,4-Tri-O-acetyl-β-D-glucuronide, Methyl Ester

Database IDs

• PubChem SID: 162255144
• PubChem CID: 71313580

CALCULATED PROPERTIES

• Acid pKa: 9.960425
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): -0.3940605
• LogD (pH = 7.4): -0.39522535
• Log P: -0.27999997
• Molar Refractivity: 126.2088 cm^3
• Polarizability: 51.11766 Å^3
• Polar Surface Area: 211.73 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 174-178°C

Safety Information

• Storage Condition: -20°C Freezer