lithium(1+) ion [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (lithiosulfanyl)phosphonate

• ChemBase ID: 134060
• Molecular Formular: C10H12Li2N5O6PS
• Molecular Mass: 375.152941
• Monoisotopic Mass: 375.05659986
• SMILES: [Li+].[Li]SP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: [Li]SP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)[O-].[Li+]
• InChI: InChI=1S/C10H14N5O6PS.2Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(21-10)1-20-22(18,19)23;;/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,23);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
• InChIKey: FZXPFDFAEUBVHA-IDIVVRGQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (lithiosulfanyl)phosphonate
• IUPAC Traditional name: lithium(1+) ion [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl lithiosulfanylphosphonate
• Synonyms: 5′-AMPS; Adenosine 5′-O-thiomonophosphate dilithium salt

Database IDs

• CAS Number: 93839-85-1
• MDL Number: MFCD00042996
• PubChem SID: 162228337; 24890572
• PubChem CID: 71308756

CALCULATED PROPERTIES

• Acid pKa: 3.3891642
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -3.4913
• LogD (pH = 7.4): -3.76049
• Log P: -3.1943185
• Molar Refractivity: 76.138 cm^3
• Polarizability: 32.541714 Å^3
• Polar Surface Area: 168.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-68/20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H371
• GHS Precautionary statements: P260
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Impurities: ≤5 mol/mol water

DETAILS

Sigma Aldrich - A1640

Application
Adenosine 5′′-O-thiomonophosphate (5′-AMPS) is a 5′-O-thiophosphate which along with adenosine 5′-O-(2-thiodiphosphate) and adenosine 5′-O-(3-thiotriphosphate) can act as inhibitors of phosphohydrolases. AMPS is a substrate for smooth muscle endothelial ecto-5′-nucleotidase. 5′APMS is a stimulator of 5-lipoxygenase activity of rat polymorphonuclear (PMN) leukocytes. Histidine triad nucleotide-binding protein 1 (HINT-1) phosphoramidase transforms nucleoside 5′-O-phosphorothioates such as 5′-AMPS to nucleoside 5′-O-phosphates.