sodium [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate

• ChemBase ID: 161007
• Molecular Formular: C10H13N5NaO7P
• Molecular Mass: 369.203051
• Monoisotopic Mass: 369.04502869
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1C[C@@H]([C@H](O1)COP(=O)(O)[O-])N=[N+]=[N-])C.[Na+]
• Canonical SMILES: [N-]=[N+]=N[C@H]1C[C@@H](O[C@@H]1COP(=O)(O)[O-])n1cc(C)c(=O)[nH]c1=O.[Na+]
• InChI: InChI=1S/C10H14N5O7P.Na/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(22-8)4-21-23(18,19)20;/h3,6-8H,2,4H2,1H3,(H,12,16,17)(H2,18,19,20);/q;+1/p-1/t6-,7+,8+;/m0./s1
• InChIKey: FVNHKXYKJMCQDY-HNPMAXIBSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• IUPAC Traditional name: sodium [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• Synonyms: AZT Monophosphate Sodium Salt; Zidovudine monophosphate; 3'-Azidothymidine Monophosphate; 3'-Azido-3'-deoxy-thymidine 5'-(Dihydrogen Phosphate); 3'-Azido-3'-deoxythymidine 5'-Monophosphate Sodium Salt

Database IDs

• CAS Number: 29706-85-2
• PubChem SID: 162255142
• PubChem CID: 71313578

CALCULATED PROPERTIES

• Acid pKa: 1.2587414
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.972618
• LogD (pH = 7.4): -4.0382185
• Log P: -0.4222752
• Molar Refractivity: 71.4557 cm^3
• Polarizability: 28.152493 Å^3
• Polar Surface Area: 157.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: 154-160°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A825070

A metabolite of the potent and selective inhibitor of HIV-1 replication, AZT.

REFERENCES

• Brehm, J., et al.: Biochem., 47, 14020 (2008)
• von Kleist, M., et al.: Eur. J. Pharm. Sci., 36, 532 (2008)