disodium [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolan-2-yl]methyl phosphate

• ChemBase ID: 175228
• Molecular Formular: C17H16N5Na2O9PS
• Molecular Mass: 543.355341
• Monoisotopic Mass: 543.02017331
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)c(ncn2)SCc1ccc(cc1)[N+](=O)[O-])COP(=O)([O-])[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1ncnc2SCc1ccc(cc1)[N+](=O)[O-])COP(=O)([O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C17H18N5O9PS.2Na/c23-13-11(5-30-32(27,28)29)31-17(14(13)24)21-8-20-12-15(21)18-7-19-16(12)33-6-9-1-3-10(4-2-9)22(25)26;;/h1-4,7-8,11,13-14,17,23-24H,5-6H2,(H2,27,28,29);;/q;2*+1/p-2/t11-,13-,14-,17-;;/m1../s1
• InChIKey: QWQORUUVPLEIAQ-CXKSGAPPSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolan-2-yl]methyl phosphate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)oxolan-2-yl]methyl phosphate
• Synonyms: 6-Nitrobenzylthioinosine 5'-Monophosphate Disodium Salt; 6-S-[(4-Nitrophenyl)methyl]-6-thio-5'-Inosinic Acid Disodium Salt; 6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine-5'-monophosphate, Disodium Salt

Database IDs

• PubChem SID: 164231138
• PubChem CID: 71751059

CALCULATED PROPERTIES

• Acid pKa: 1.2244388
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): -1.6685163
• LogD (pH = 7.4): -2.7276397
• Log P: -2.0077453
• Molar Refractivity: 111.8701 cm^3
• Polarizability: 44.006382 Å^3
• Polar Surface Area: 211.53 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White to Off-White Solid
• Melting Point: 156-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N495770

Used in therapy of mouse leukemia L1210 in combinations with Nebularin and Nitrobenzylthioinosine 5’-monophosphate.

REFERENCES

• Anderson, C., et al.: Neurosci. Lett., 219, 191 (1996)
• Allay, J., et al.: Nat. Med., 4, 1136 (1996)