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D6392

P¹,P⁵-Di(adenosine-5′) pentaphosphate trilithium salt

Name: P<SUP>1</SUP>,P<SUP>5</SUP>-Di(adenosine-5′) pentaphosphate trilithium salt
Brand: SIGMA

≥95%, powder

Synonym(s):

A(5′)P5(5′)A trilithium salt, Diadenosine pentaphosphate trilithium salt

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₆Li₃N₁₀O₂₂P₅

CAS Number:

75522-97-3

Molecular Weight:

934.17

EC Number:

278-237-6

MDL number:

MFCD00044936

UNSPSC Code:

12352202

eCl@ss:

32160414

PubChem Substance ID:

24894024

NACRES:

NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥95%

form

powder

color

white to off-white

solubility

H₂O: 50 mg/mL

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)[C@@H](O)[C@H]3O

InChI

1S/C20H29N10O22P5.3Li/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30;;;/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26);;;/q;3*+1/p-3/t7-,8-,11-,12-,13-,14-,19-,20-;;;/m1.../s1

InChI key

BFBDFBHROZLGEG-JJCYRVQFSA-K

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Related Categories

Phosphates

Application

P1,P5-Di(adenosine-5′) pentaphosphate trilithium salt has been used as a adenylate kinase inhibitor and as a component of pre-AMPPNP rigor solution for treating muscle fibres.

Biochem/physiol Actions

A diadenosine polyphosphate stored in secretory granules of thrombocytes, chromaffin and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Behavior of N-phenylmaleimide-and p-phenylenedimaleimide-reacted muscle crossbridge heads

Li WX and Schoenberg M

Biochimica et Biophysica Acta - Bioenergetics, 1367(1-3), 127-133 (1998)

Mitochondrial diagnostics: a multiplexed assay platform for comprehensive assessment of mitochondrial energy fluxes

Fisher-Wellman KH, et al.

Testing, 24(13), 3593-3606 (2018)

Effect of adenosine triphosphate analogues on skeletal muscle fibers in rigor

Schoenberg M

Biophysical Journal, 56(1), 33-41 (1989)

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