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Merck
CN

D4022

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

≥95% (HPLC), powder

Synonym(s):

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

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About This Item

Linear Formula:
C20H29N10O22P5 · 5 Na
CAS Number:
4097-04-5
Molecular Weight:
1026.28
NACRES:
NA.51
PubChem Substance ID:
24893808
eCl@ss:
32160414
UNSPSC Code:
12352202
EC Number:
223-852-7
MDL number:
MFCD00077718
Beilstein/REAXYS Number:
4949216

Key Documents

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Product Name

P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt, ≥95% (HPLC), powder

InChI

1S/C20H29N10O22P5.5Na/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;5*+1/p-5/t7-,8-,11-,12-,13-,14-,19-,20-;;;;;/m1...../s1

InChI key

NNMFUJJMJIYTSP-CSMIRWGRSA-I

SMILES string

[Na+].[Na+].[Na+].[Na+].[Na+].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

biological source

synthetic (organic)

assay

≥95% (HPLC)

form

powder

mol wt

~_1.0 kDa

color

white to yellow-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

Quality Level

200

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Application

P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt has been used as:
  • an adenylate kinase (AK) inhibitor in: sarcoma osteogenic (Saos-2) cells
  • mitochondrial lysates during ATP synthesis
  • tetramethylrhodamine methyl ester (TMRM) based membrane potential assay
  • chromoplasts

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.
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.

General description

P1,P5-Di(adenosine-5′) pentaphosphate (Ap5A) is a diadenosine polyphosphate, which has a tail-to-tail dimer structure. Ap5A is synthesized in a twostep process involving the formation of adenosine 5′-tetraphosphate (P4A) from the ATP and trimeta-phosphate (P3). In the second step, P4A is converted to Ap5A. The synthesis of Ap5A requires a pH optimum in the range of 7.5 to 8.5 and is modulated by metal ions.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000451805
0000451804
0000451805
0000451804
0000426992

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Polyphosphate as a donor of high-energy phosphate for the synthesis of ADP and ATP
Muller WEG, et al.
Journal of Cell Science, 130(16), 2747-2756 (2017)
Facile and selective synthesis of diadenosine polyphosphates through catalysis by leucyl t-RNA synthetase coupled with ATP regeneration
Nakajima H, et al.
Agricultural and Biological Chemistry, 53(3), 615-623 (1989)
Isolation of Tomato Fruit Chromoplasts and Determination of ATP Levels
Yaakov B
The Plant Journal (2013)
Soluble adenylyl cyclase-mediated cAMP signaling and the putative role of PKA and EPAC in cerebral mitochondrial function
Jakobsen E, et al.
Journal of Neuroscience Research (2019)
Gourav Bhardwaj et al.
The Journal of clinical investigation, 131(18) (2021-08-04)
Decreased skeletal muscle strength and mitochondrial dysfunction are characteristic of diabetes. The actions of insulin and IGF-1 through the insulin receptor (IR) and IGF-1 receptor (IGF1R) maintain muscle mass via suppression of forkhead box O (FoxO) transcription factors, but whether
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