1.0 2011-09-21 00:14:51 UTC 2015-07-21 06:57:14 UTC FDB022492 Diadenosine tetraphosphate Diadenosine tetraphosphate (AP4A) 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. AP4A is the only APnA that can induce a considerable increase in [Ca2+] in endothelial cells, indicating that its vasoactive effects are comparable to the known effects of arginine vasopressin, Angiotensin II, and ATP. AP4A is a ubiquitous ApnA is a signal molecule for DNA replication in mammalian cells. AP4A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP4A 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. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 9694344, 9351706, 1953194) [HMDB] (PpA)2 5',5'''-diadenosine tetraate 5',5'''-Diadenosine tetraphosphate Adenosine 5'-tetraate, 5'-ester with adenosine Adenosine 5'-tetraphosphate, 5'-ester with adenosine Adenosine-(5')-tetrao-(5')-adenosine adenosine-(5')-tetraphospho-(5')-adenosine AppppA Bis(5'-adenylyl) diate Bis(5'-adenylyl) diic acid Diadenosine 5',5'''-P1,P4-tetraate Diadenosine 5',5'''-P1,P4-tetraphosphate P1,P4-Bis(5'-adenosyl) tetraate P1,P4-Bis(5'-adenosyl) tetraic acid P1,P4-Di(adenosin-5'-yl)tetraate P1,P4-Di(adenosin-5'-yl)tetraphosphate P1,P4-Diadenosine-5'-tetraate P1,P4-Diadenosine-5'-tetraphosphate C20H28N10O19P4 836.387 836.048264812 [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid appppa 5542-28-9 NC1=C2N=CN([C@@H]3O[C@H](COP(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=N1 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)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1 YOAHKNVSNCMZGQ-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')-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 diadenosyl tetraphosphate Solid logp -0.71 ALOGPS logs -2.18 ALOGPS solubility 5.59e+00 g/l ALOGPS logp -9.5 ChemAxon pka_strongest_acidic 0.59 ChemAxon pka_strongest_basic 4.28 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 836.387 ChemAxon mono_mass 836.048264812 ChemAxon smiles NC1=C2N=CN([C@@H]3O[C@H](COP(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=N1 ChemAxon formula C20H28N10O19P4 ChemAxon 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)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1 ChemAxon inchikey YOAHKNVSNCMZGQ-XPWFQUROSA-N ChemAxon polar_surface_area 433.97 ChemAxon refractivity 166.1 ChemAxon polarizability 66.83 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 22 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 24482 Specdb::MsMs 24483 Specdb::MsMs 24484 Specdb::MsMs 31040 Specdb::MsMs 31041 Specdb::MsMs 31042 Specdb::MsMs 2779006 Specdb::MsMs 2779007 Specdb::MsMs 2779008 Specdb::MsMs 2902551 Specdb::MsMs 2902552 Specdb::MsMs 2902553 Specdb::EiMs 5606 Specdb::NmrOneD 8922 Specdb::NmrOneD 8923 Specdb::NmrOneD 8924 Specdb::NmrOneD 8925 Specdb::NmrOneD 8926 Specdb::NmrOneD 8927 Specdb::NmrOneD 8928 Specdb::NmrOneD 8929 Specdb::NmrOneD 8930 Specdb::NmrOneD 8931 Specdb::NmrOneD 8932 Specdb::NmrOneD 8933 Specdb::NmrOneD 8934 Specdb::NmrOneD 8935 Specdb::NmrOneD 8936 Specdb::NmrOneD 8937 Specdb::NmrOneD 8938 Specdb::NmrOneD 8939 Specdb::NmrOneD 8940 Specdb::NmrOneD 8941 HMDB01211 17422 B4P #<Reference:0x000055ce3198aee0> #<Reference:0x000055ce3198ad28> #<Reference:0x000055ce3198ab70> #<Reference:0x000055ce3198a9b8> #<Reference:0x000055ce3198a800> #<Reference:0x000055ce3198a648> #<Reference:0x000055ce3198a490> #<Reference:0x000055ce3198a2d8> #<Reference:0x000055ce3198a120> #<Reference:0x000055ce31989f68> #<Reference:0x000055ce31989db0> #<Reference:0x000055ce31989bf8> #<Reference:0x000055ce31989a40> #<Reference:0x000055ce31989888> #<Reference:0x000055ce319896d0> #<Reference:0x000055ce31989518> #<Reference:0x000055ce31989360> #<Reference:0x000055ce319891a8> #<Reference:0x000055ce31988ff0> #<Reference:0x000055ce31988e38>