1.02011-09-21 00:15:29 UTC2015-07-21 06:57:15 UTCFDB022533Diadenosine hexaphosphateDiadenosine hexaphosphate (AP6A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are AP3A, AP4A, AP5A, and AP6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP6A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity.
AP6A have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. AP6A have been identified in human platelets and shown to be an important modulator of cardiovascular function. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 16401072, 12738682, 10094777) [HMDB]Adenosine 5'-(heptahydrogen hexaate) P->5'-ester with adenosineAdenosine 5'-(heptahydrogen hexaate)5'-5'-ester with adenosineAdenosine 5'-(heptahydrogen hexaphosphate) P->5'-ester with adenosineAdenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosineAdenosine 5'-hexaate 5'-ester with adenosineAdenosine 5'-hexaic acid 5'-ester with adenosineAdenosine 5'-hexaphosphate 5'-ester with adenosineAdenosine-(5')-hexaO-(5')-adenosineAdenosine-(5')-hexaphospho-(5')-adenosineAp(6)AAP6AAppppppADiadenosine 5',5''''-P1,P6-hexaateDiadenosine 5',5''''-P1,P6-hexaic acidDiadenosine 5',5''''-P1,P6-hexaphosphateDiadenosine hexaateDiadenosine hexaic acidP1,P6-Di(adenosine-5')hexaateP1,P6-Di(adenosine-5')hexaic acidP1,P6-di(Adenosine-5')hexaphosphateC20H30N10O25P6996.3468995.980925632{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acidAppppppA56983-23-4NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(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)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1InChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)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)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1PZCFFCOJNXGTIM-XPWFQUROSA-N belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.(5'->5')-dinucleotidesOrganic compoundsNucleosides, nucleotides, and analogues(5'->5')-dinucleotidesAromatic heteropolycyclic compounds6-aminopurinesAminopyrimidines and derivativesAzacyclic compoundsGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesImidolactamsMonoalkyl phosphatesMonosaccharide phosphatesN-substituted imidazolesOrganic oxidesOrganopnictogen compoundsOxacyclic compoundsPentose phosphatesPrimary aminesPurine nucleotide sugarsPurine ribonucleoside monophosphatesPurine ribonucleoside polyphosphatesSecondary alcoholsTetrahydrofurans(5'->5')-dinucleotide6-aminopurineAlcoholAlkyl phosphateAmineAminopyrimidineAromatic heteropolycyclic compoundAzacycleAzoleGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeImidazoleImidazopyrimidineImidolactamMonoalkyl phosphateMonosaccharideMonosaccharide phosphateN-glycosyl compoundN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacyclePentose phosphatePentose-5-phosphatePhosphoric acid esterPrimary aminePurinePurine nucleotide sugarPurine ribonucleoside monophosphatePurine ribonucleoside polyphosphatePyrimidineSecondary alcoholTetrahydrofurandiadenosyl hexaphosphateSolidlogp0.26logs-2.15solubility6.99e+00 g/llogp-10pka_strongest_acidic0.28pka_strongest_basic5.3iupac{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acidaverage_mass996.3468mono_mass995.980925632smilesNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(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)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1formulaC20H30N10O25P6inchiInChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)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)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1inchikeyPZCFFCOJNXGTIM-XPWFQUROSA-Npolar_surface_area527.03refractivity187.85polarizability76.38rotatable_bond_count18acceptor_count26donor_count12physiological_charge-6formal_charge0Specdb::NmrOneD9102Specdb::NmrOneD9103Specdb::NmrOneD9104Specdb::NmrOneD9105Specdb::NmrOneD9106Specdb::NmrOneD9107Specdb::NmrOneD9108Specdb::NmrOneD9109Specdb::NmrOneD9110Specdb::NmrOneD9111Specdb::NmrOneD9112Specdb::NmrOneD9113Specdb::NmrOneD9114Specdb::NmrOneD9115Specdb::NmrOneD9116Specdb::NmrOneD9117Specdb::NmrOneD9118Specdb::NmrOneD9119Specdb::NmrOneD9120Specdb::NmrOneD9121Specdb::MsMs25322Specdb::MsMs25323Specdb::MsMs25324Specdb::MsMs31880Specdb::MsMs31881Specdb::MsMs31882Specdb::MsMs2421213Specdb::MsMs2421214Specdb::MsMs2421215Specdb::MsMs2544814Specdb::MsMs2544815Specdb::MsMs2544816HMDB01282B6P#<Reference:0x00005556752494f8>#<Reference:0x0000555675249318>#<Reference:0x0000555675249098>#<Reference:0x0000555675248e68>#<Reference:0x0000555675248c88>#<Reference:0x0000555675248a30>#<Reference:0x00005556752487d8>#<Reference:0x0000555675248328>#<Reference:0x0000555675248120>#<Reference:0x000055567523bba0>#<Reference:0x000055567523b8d0>#<Reference:0x000055567523b5d8>#<Reference:0x000055567523b218>#<Reference:0x000055567523af20>#<Reference:0x000055567523ad18>#<Reference:0x000055567523aa20>#<Reference:0x000055567523a750>#<Reference:0x000055567523a4d0>#<Reference:0x000055567523a278>#<Reference:0x0000555675239ff8>#<Reference:0x00005556752236e0>#<Reference:0x00005556752234d8>#<Reference:0x0000555675223078>#<Reference:0x0000555675222e48>AnatidaeType 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