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

• ChemBase ID: 133732
• Molecular Formular: C10H15Li4N6O13P3
• Molecular Mass: 547.943783
• Monoisotopic Mass: 548.05501266
• SMILES: [Li+].[Li+].[Li+].[Li+].c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(NP(=O)([O-])[O-])[O-])O)O)N.O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(NP(=O)([O-])[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.[Li+].[Li+].[Li+].[Li+].O
• InChI: InChI=1S/C10H17N6O12P3.4Li.H2O/c11-8-5-9(13-2-12-8)16(3-14-5)10-7(18)6(17)4(27-10)1-26-31(24,25)28-30(22,23)15-29(19,20)21;;;;;/h2-4,6-7,10,17-18H,1H2,(H,24,25)(H2,11,12,13)(H4,15,19,20,21,22,23);;;;;1H2/q;4*+1;/p-4/t4-,6-,7-,10-;;;;;/m1...../s1
• InChIKey: YJCDTIXYXQSSCQ-AZGWGOJFSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetralithium(1+) ion hydrate {[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]amino}phosphonate
• IUPAC Traditional name: tetralithium(1+) ion hydrate ({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)aminophosphonate
• Synonyms: β,γ-Imidoadenosine 5′-triphosphate lithium salt hydrate; AMP-PNP; ATP[β,γ-NH]; Adenylyl imidodiphosphate lithium salt hydrate; App(NH)p; Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate

Database IDs

• CAS Number: 25612-73-1(freeacid)
• EC Number: 277-127-5
• Beilstein Number: 6047109
• PubChem SID: 24890685; 162228009
• PubChem CID: 16218881

CALCULATED PROPERTIES

• Acid pKa: -8.055352
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): -10.633878
• LogD (pH = 7.4): -12.583426
• Log P: -6.5044765
• Molar Refractivity: 93.2773 cm^3
• Polarizability: 38.54618 Å^3
• Polar Surface Area: 293.25 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); ≥93% (HPLC)
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C10H17N6O12P3 · xLi+ · yH2O

DETAILS

Sigma Aldrich - A2647

Biochem/physiol Actions
A non-hydrolyzable ATP analog. AMP-PNP competitively inhibits ATP-dependent enzyme systems, such as glutamine synthetase. It inhibits a number of enzymes which require the hydrolysis of ATP such as DNA topoisomerase II, SV40 large T-antigen helicase and a number of kinases. Blocks ATP-sensitive calcium-dependent potassium channels.
Caution
AMP-PNP is very unstable in acidic conditions; rapidly hydrolyzes to the phosphoramidate and inorganic phosphate.
Reconstitution
A 10 mg/mL stock solution may be made, aliquoted and stored at -70 °C for up to 3 months.
Application
Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate has been used in a study to research the effects of monovalent cations Li+, Na+, K+, NH4+, Rb+ and Cs+ on the solid and solution structures of the nucleic acid components. Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate has also been used in a study to determine that antidepressants inhibit interferon-γ-induced microglial production of IL-6 and nitric oxide.

Sigma Aldrich - 01910

Other Notes
ATP analogue. Competitive inhibitor of ATP-dependent enzyme systems1; Inhibitor of mitochondrial F1-ATPase : Review2