disodium [(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

• ChemBase ID: 130941
• Molecular Formular: C10H11N4Na2O9P
• Molecular Mass: 408.169041
• Monoisotopic Mass: 408.00590314
• SMILES: c1nc2c(n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])[O-])O)O)[nH]c(=O)[nH]c2=O.[Na+].[Na+]
• Canonical SMILES: O=c1[nH]c(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)([O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C10H13N4O9P.2Na/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17;;/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18);;/q;2*+1/p-2/t3-,5-,6-,9-;;/m1../s1
• InChIKey: QQPVYRBCIRHGSZ-LGVAUZIVSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• IUPAC Traditional name: disodium XMP
• Synonyms: Xanthosine 5’-Monophosphate Disodium Salt; 5'-Xanthylic Acid Disodium Salt; XMP; Xanthosine 5′-monophosphate disodium salt

Database IDs

• CAS Number: 25899-70-1
• EC Number: 247-324-0
• MDL Number: MFCD00037982
• PubChem SID: 162225219; 24902125
• PubChem CID: 10287649

CALCULATED PROPERTIES

• Acid pKa: 1.2561243
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -4.3716793
• LogD (pH = 7.4): -5.4704556
• Log P: -2.1784012
• Molar Refractivity: 70.838 cm^3
• Polarizability: 28.130703 Å^3
• Polar Surface Area: 198.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥85%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C10H11N4Na2O9P

DETAILS

Toronto Research Chemicals - X743800

Xanthosine 5’-Monophosphate as chameleon-like nucleotide.

REFERENCES

• Noguchi, Y., et al.: Eur. J. Biochem., 270, 2622 (2003)
• Boitz, J., et al.: J. Biol. Chem., 281, 16084 (2003)