1.0 2011-09-21 00:14:40 UTC 2015-07-21 06:57:14 UTC FDB022479 Diadenosine pentaphosphate Diadenosine pentaphosphate (AP5A) 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. AP5A is a specific adenylate kinase inhibitor in the hippocampus, decreasing the rate of decomposition of ADP and the formation of ATP; a pathway that influences the availability of purines in the central nervous system. AP5A in nanomolar concentrations is found to significantly stimulate the proliferation of vascular smooth muscle cells. AP5A is a P2X agonist. The activation of nucleotide ion tropic receptors increases intracellular calcium concentration, resulting in calcium/calmodulin-dependent protein kinase II (CaMKII) activation. AP5A 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. AP5A have been identified in human platelets and shown to be important modulator of cardiovascular function. AP5A is stored in synaptic vesicles and released upon nerve terminal depolarization. At the extracellular level, AP5A can stimulate presynaptic dinucleotide receptors. Responses to AP5A have been described in isolated synaptic terminals (synaptosomes) from several brain areas in different animal species, including man. Dinucleotide receptors are ligand-operated ion channels that allow the influx of cations into the terminals. These cations reach a threshold for N- and P/Q-type voltage-dependent calcium channels, which become activated. The activation of the dinucleotide receptor together with the activation of these calcium channels triggers the release of neurotransmitters. The ability of Ap5A to promote glutamate, GABA or acetylcholine release has been described. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 10094777, 16401072, 16819989, 17721817, 17361116, 14502438) [HMDB] Bis(5'-adenosyl) pentaate Bis(5'-adenosyl) pentaphosphate Bis(adenosine)-5'-pentaate Bis(Adenosine)-5'-Pentaphosphate P1,P5-Bis(5'-adenosyl) pentaate P1,P5-Bis(5'-adenosyl) pentaphosphate C20H29N10O22P5 916.3669 916.014595222 {[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R)-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]phosphinic acid [(3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid 41708-91-2 NC1=NC=NC2=C1N=CN2[C@@H]1OC(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2OC([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 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)/t7-,8?,11-,12-,13-,14-,19?,20-/m1/s1 OIMACDRJUANHTJ-OEOQABFDSA-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')-dinucleotides Organic compounds Nucleosides, nucleotides, and analogues (5'->5')-dinucleotides Aromatic heteropolycyclic compounds 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine nucleotide sugars Purine ribonucleoside monophosphates Purine ribonucleoside polyphosphates Secondary alcohols Tetrahydrofurans (5'->5')-dinucleotide 6-aminopurine Alcohol Alkyl phosphate Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine nucleotide sugar Purine ribonucleoside monophosphate Purine ribonucleoside polyphosphate Pyrimidine Secondary alcohol Tetrahydrofuran Solid logp -0.20 ALOGPS logs -2.12 ALOGPS solubility 6.92e+00 g/l ALOGPS logp -11 ChemAxon pka_strongest_acidic 0.42 ChemAxon pka_strongest_basic 5.3 ChemAxon iupac {[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R)-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]phosphinic acid ChemAxon average_mass 916.3669 ChemAxon mono_mass 916.014595222 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@@H]1OC(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2OC([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O ChemAxon formula C20H29N10O22P5 ChemAxon 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)/t7-,8?,11-,12-,13-,14-,19?,20-/m1/s1 ChemAxon inchikey OIMACDRJUANHTJ-OEOQABFDSA-N ChemAxon polar_surface_area 480.5 ChemAxon refractivity 176.98 ChemAxon polarizability 70.64 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 24 ChemAxon donor_count 11 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 317740 Specdb::MsMs 317741 Specdb::MsMs 317742 Specdb::MsMs 364294 Specdb::MsMs 364295 Specdb::MsMs 364296 Specdb::MsMs 2378602 Specdb::MsMs 2378603 Specdb::MsMs 2378604 Specdb::MsMs 2557581 Specdb::MsMs 2557582 Specdb::MsMs 2557583 Specdb::NmrOneD 8882 Specdb::NmrOneD 8883 Specdb::NmrOneD 8884 Specdb::NmrOneD 8885 Specdb::NmrOneD 8886 Specdb::NmrOneD 8887 Specdb::NmrOneD 8888 Specdb::NmrOneD 8889 Specdb::NmrOneD 8890 Specdb::NmrOneD 8891 Specdb::NmrOneD 8892 Specdb::NmrOneD 8893 Specdb::NmrOneD 8894 Specdb::NmrOneD 8895 Specdb::NmrOneD 8896 Specdb::NmrOneD 8897 Specdb::NmrOneD 8898 Specdb::NmrOneD 8899 Specdb::NmrOneD 8900 Specdb::NmrOneD 8901 HMDB01192 #<Reference:0x000055ce305c12b0> #<Reference:0x000055ce305c10f8> #<Reference:0x000055ce305c0f40> #<Reference:0x000055ce305c0d88> #<Reference:0x000055ce305c0bd0> #<Reference:0x000055ce305c0a18> #<Reference:0x000055ce305c0860> #<Reference:0x000055ce305c06a8> #<Reference:0x000055ce305c0450> #<Reference:0x000055ce305c0298> #<Reference:0x000055ce305c00e0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823