tetralithium(1+) ion [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[dioxido(sulfanylidene)-λ5-phosphanyl phosphonato]oxy}phosphonate

• ChemBase ID: 105256
• Molecular Formular: C10H12Li4N5O12P3S
• Molecular Mass: 546.978863
• Monoisotopic Mass: 547.00561994
• SMILES: [Li+].[Li+].[Li+].[Li+].Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)([O-])OP(=O)([O-])OP(=S)([O-])[O-])[C@@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=S)([O-])[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Li+].[Li+].[Li+].[Li+]
• InChI: InChI=1S/C10H16N5O12P3S.4Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-28(18,19)26-29(20,21)27-30(22,23)31;;;;/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H,20,21)(H2,11,12,13)(H2,22,23,31);;;;/q;4*+1/p-4/t4-,6-,7-,10-;;;;/m1..../s1
• InChIKey: DWQFDOIBOYDYKH-KWIZKVQNSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetralithium(1+) ion [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[dioxido(sulfanylidene)-λ^5-phosphanyl phosphonato]oxy}phosphonate
• IUPAC Traditional name: tetralithium(1+) ion [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [dioxido(sulfanylidene)-λ^5-phosphanyl phosphonato]oxyphosphonate
• Synonyms: ATP-γ-S; Adenosine 5′-(3-thiotriphosphate) tetralithium salt; Ado-5′-PPP[S]; Adenosine 5′-[γ-thio]triphosphate tetralithium salt; ATP-β-S; ADENOSINE-5'-O-(3-THIOTRIPHOSPHATE)

Database IDs

• CAS Number: 93839-89-5
• EC Number: 298-862-8
• MDL Number: MFCD00077293
• Beilstein Number: 6265083
• PubChem SID: 162093619; 24890536
• PubChem CID: 5311341

CALCULATED PROPERTIES

• Acid pKa: 1.0290036
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): -9.210865
• LogD (pH = 7.4): -10.55693
• Log P: -4.4397917
• Molar Refractivity: 99.3184 cm^3
• Polarizability: 41.229645 Å^3
• Polar Surface Area: 273.38 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: -20°C, Desiccate
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: >80%; ≥75%; ≥75% (HPLC)
• Impurities: ≤1% AMP; ≤12% ADP; ≤12% water
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C10H12Li4N5O12P3S

DETAILS

MP Biomedicals - 02159551

Tetralithium Salt
Purity: >80%

Sigma Aldrich - A1388

Biochem/physiol Actions
P2 purinergic agonist; increases activity of Ca2+-activated K+ channels; can substitute for ATP in kinase reactions yielding thiophosphorylated proteins that are resistant to protein phosphatases.
Other Notes
Non-hydrolyzable ATP analog
Application
Adenosine 5′-[γ-thio]triphosphate (ATP-γ-S) is widely used as a non-hydrolyzed ATP analogue for studies on the effects of ATP binding to ATP sites in a wide range of processes including extracellular functions. ATP- γ-S is a P2 purinergic agonist which increases the activity of Ca2+-activated K+ channels. ATP- γ-S can substitute for ATP in kinase reactions yielding thiophosphorylated proteins that are resistant to protein phosphatases and modulate the ATP-dependent steps in the binding of ubiquitin conjugates to the 26S proteasome. ATP-γ -S differentially modulates Toll-like receptor 4-mediated cell survival and death.

Sigma Aldrich - 01995

Other Notes
Review: Nucleoside phosphorothioates1

REFERENCES

• Chrysogelos, S., et al., J. Biol. Chem. , 258 : 12624, (1983).