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

Abbrev Name: Ap5A

Synonyms: bis(5'-adenosyl) pentaphosphate, P1,P5-bis(5'-adenosyl) pentaphosphate, P(1),P(5)-di(adenosine-5'-)pentaphosphate, Ap5A, P1,P5-di(adenosine-5')-pentaphosphate

Superclasses: a nucleic acid component a nucleoside a dinucleoside polyphosphate a diadenosine polyphosphate

Summary:
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: C20H24N10O22P5

Molecular Weight: 911.33 Daltons

Monoisotopic Molecular Weight: 916.0145952190999 Daltons

SMILES: C1(N=C(N)C2(N=CN(C(N=1)=2)C3(C(O)C(O)C(O3)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(OCC6(OC(N4(C=NC5(=C4N=CN=C(N)5)))C(O)C(O)6))(=O)[O-])))

InChI: InChI=1S/C20H29N10O22P5/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)/p-5/t7-,8?,11-,12-,13-,14-,19-,20-/m1/s1

InChIKey: InChIKey=OIMACDRJUANHTJ-KEQCZIJCSA-I

Unification Links: ChEBI:62041 , IAF1260:43056 , KEGG:C04058 , PubChem:25202759

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -752.7127 Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

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

In Reactions of unknown directionality:

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


a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

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

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

Inhibitor (Competitive) of: UMP kinase [Zhou98a]

Inhibitor (Mechanism unknown) of: adenylate kinase [Barzu83, Muller92]

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


References

Barzu83: Barzu O, Michelson S (1983). "Simple and fast purification of Escherichia coli adenylate kinase." FEBS Lett 1983;153(2);280-4. PMID: 6311616

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

Muller92: Muller CW, Schulz GE (1992). "Structure of the complex between adenylate kinase from Escherichia coli and the inhibitor Ap5A refined at 1.9 A resolution. A model for a catalytic transition state." J Mol Biol 1992;224(1);159-77. PMID: 1548697

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

Zhou98a: Zhou L, Lacroute F, Thornburg R (1998). "Cloning, expression in Escherichia coli, and characterization of Arabidopsis thaliana UMP/CMP kinase." Plant Physiol 117(1);245-54. PMID: 9576794


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 29, 2014, BIOCYC15A.