MetaCyc Compound: 5',5'''-diadenosine tetraphosphate

Abbrev Name: Ap4A

Synonyms: Ap4A, AppppA, P(1),P(4)-bis(5'-adenosyl)tetraphosphate, P1,P4-bis(5'-adenosyl)tetraphosphate

Superclasses: a nucleic acid componenta nucleosidea dinucleoside polyphosphatea diadenosine polyphosphate

Several important intracellular and extracellular signaling functions have been ascribed to the diadenosine compounds 5',5'''-diadenosine triphosphate, 5',5'''-diadenosine tetraphosphate, 5',5'''-diadenosine pentaphosphate and 5',5'''-diadenosine hexaphosphate [MirasPortugal98, MirasPortugal99, GomezVillafuert00, Pintor, Delicado06].

Chemical Formula: C20H24N10O19P4

Molecular Weight: 832.36 Daltons

Monoisotopic Molecular Weight: 836.0482648107001 Daltons

5',5'''-diadenosine tetraphosphate compound structure

SMILES: C(C1(C(C(C(O1)N3(C=NC2(C(=NC=NC=23)N)))O)O))OP(OP(OP(OP(OCC4(C(C(C(O4)N6(C=NC5(C(=NC=NC=56)N)))O)O))([O-])=O)([O-])=O)([O-])=O)([O-])=O

InChI: InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)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)(H2,21,23,25)(H2,22,24,26)/p-4/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1


Unification Links: ChEBI:58141, HMDB:HMDB01211, IAF1260:1484745, KEGG:C01260, MetaboLights:MTBLC58141, PubChem:25243905

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -638.3041Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
5',5'''-diadenosine tetraphosphate + H2O → 2 ADP + 2 H+

Reactions known to produce the compound:

Not in pathways:
a nucleoside 5'-monophosphate[periplasm] + H2O[periplasm]a nucleoside[periplasm] + phosphate[periplasm]
a nucleotide + H2O → a nucleoside + phosphate

In Reactions of unknown directionality:

Not in pathways:
ATP + ADP + H+ = 5',5'''-diadenosine tetraphosphate + phosphate
ATP + ATP + H+ = 5',5'''-diadenosine tetraphosphate + diphosphate
5',5'''-diadenosine tetraphosphate + H2O = ATP + AMP + 2 H+

Not in pathways:
a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

In Transport reactions:
a nucleoside[extracellular space]a nucleoside[periplasm],
a nucleoside[periplasm] + H+[periplasm]a nucleoside[cytosol] + H+[cytosol]

Enzymes inhibited by 5',5'''-diadenosine tetraphosphate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: acid phosphatase / phosphotransferase [Thaller97]

Revised 29-Oct-2009 by Caspi R, SRI International


Delicado06: Delicado EG, Miras-Portugal MT, Carrasquero LM, Leon D, Perez-Sen R, Gualix J (2006). "Dinucleoside polyphosphates and their interaction with other nucleotide signaling pathways." Pflugers Arch 452(5);563-72. PMID: 16688466

GomezVillafuert00: Gomez-Villafuertes R, Gualix J, Miras-Portugal MT, Pintor J (2000). "Adenosine 5'-tetraphosphate (Ap(4)), a new agonist on rat midbrain synaptic terminal P2 receptors." Neuropharmacology 39(12);2381-90. PMID: 10974322

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

MirasPortugal98: Miras-Portugal MT, Gualix J, Pintor J (1998). "The neurotransmitter role of diadenosine polyphosphates." FEBS Lett 430(1-2);78-82. PMID: 9678598

MirasPortugal99: Miras-Portugal MT, Gualix J, Mateo J, Diaz-Hernandez M, Gomez-Villafuertes R, Castro E, Pintor J (1999). "Diadenosine polyphosphates, extracellular function and catabolism." Prog Brain Res 120;397-409. PMID: 10551014

Pintor: Pintor J, Diaz-Hernandez M, Gualix J, Gomez-Villafuertes R, Hernando F, Miras-Portugal MT "Diadenosine polyphosphate receptors. from rat and guinea-pig brain to human nervous system." Pharmacol Ther 87(2-3);103-15. PMID: 11007994

Thaller97: Thaller MC, Schippa S, Bonci A, Cresti S, Rossolini GM (1997). "Identification of the gene (aphA) encoding the class B acid phosphatase/phosphotransferase of Escherichia coli MG1655 and characterization of its product." FEMS Microbiol Lett 1997;146(2);191-8. PMID: 9011040

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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