1.0 2011-09-21 00:15:41 UTC 2015-07-21 06:57:15 UTC FDB022547 Diadenosine diphosphate Diadenosine diphosphate is a member of the diadenosine polyphosphates. Diadenosine diphosphate is typically synthesized from ADP-ribosyl cyclases. Diadenosine polyphosphates are members of a group of dinucleoside polyphosphates that are ubiquitous, naturally occurring molecules. They form a recently identified class of compounds derived from ATP and consist of two adenosine molecules bridged by up to six phosphate groups. These compounds are stored in high concentrations in platelet dense granules and are released when platelets become activated. Some of the compounds promote platelet aggregation, while others are inhibitory. Possible roles as neurotransmitters, extracellular signalling molecules or 'alarmones' secreted by cells in response to physiologically stressful stimuli have been postulated. Recent studies suggest a role for these compounds in atrial and synaptic neurotransmission. Studies using isolated mesenteric arteries indicate an important role of phosphate chain length in determining whether diadenosine polyphosphates produce vasodilatation or vasoconstriction, but in the coronary circulation, diadenosine polyphosphates generally produce vasodilatation via mechanisms thought to involve release of NO or prostacyclin (PGI2). They produce cardiac electrophysiological effects by altering ventricular refractoriness at submicromolar concentrations and reduce heart rate. Mechanisms involving KATP channels have been proposed in addition to the involvement of P1- and P2-purinergic receptors and the specific diadenosine polyphosphate receptor identified on isolated cardiac myocytes. Clinical evidence suggests a role for diadenosine polyphosphates in hypertensive patients and those with the Chediak-Higashi syndrome. (PMID: 10434992) [HMDB] Diadenosine pyroate Diadenosine pyrophosphate Diadenosine-5',5'-pyroate Diadenosine-5',5'-pyrophosphate P(1),P(2)-Di(adenosine 5'-)diate P(1),P(2)-Di(adenosine 5'-)diphosphate P(1),P(2)-Diadenosine-5'-pyroate P(1),P(2)-Diadenosine-5'-pyrophosphate C20H26N10O13P2 676.4272 676.115603992 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid 14938-28-4 NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1 InChI=1S/C20H26N10O13P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(33)11(32)8(41-19)2-39-44(35,36)43-45(37,38)42-14-7(1-31)40-20(13(14)34)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)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20+/m1/s1 FHISWBUCBBVWGG-SNESVTBZSA-N belongs to the class of organic compounds known as (3'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (3'->5')-phosphodiester linkage. (3'->5')-dinucleotides Organic compounds Nucleosides, nucleotides, and analogues (3'->5')-dinucleotides and analogues (3'->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 Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary alcohols Primary amines Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Ribonucleoside 3'-phosphates Secondary alcohols Tetrahydrofurans (3'->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 Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary alcohol Primary amine Purine Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pyrimidine Ribonucleoside 3'-phosphate Secondary alcohol Tetrahydrofuran Solid logp -1.76 ALOGPS logs -2.18 ALOGPS solubility 4.50e+00 g/l ALOGPS logp -8 ChemAxon pka_strongest_acidic 1.84 ChemAxon pka_strongest_basic 5.29 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid ChemAxon average_mass 676.4272 ChemAxon mono_mass 676.115603992 ChemAxon smiles NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1 ChemAxon formula C20H26N10O13P2 ChemAxon inchi InChI=1S/C20H26N10O13P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(33)11(32)8(41-19)2-39-44(35,36)43-45(37,38)42-14-7(1-31)40-20(13(14)34)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)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20+/m1/s1 ChemAxon inchikey FHISWBUCBBVWGG-SNESVTBZSA-N ChemAxon polar_surface_area 340.91 ChemAxon refractivity 144.36 ChemAxon polarizability 58.41 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 18 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 318124 Specdb::MsMs 318125 Specdb::MsMs 318126 Specdb::MsMs 364816 Specdb::MsMs 364817 Specdb::MsMs 364818 Specdb::MsMs 2338785 Specdb::MsMs 2338786 Specdb::MsMs 2338787 Specdb::MsMs 2623967 Specdb::MsMs 2623968 Specdb::MsMs 2623969 Specdb::NmrOneD 9162 Specdb::NmrOneD 9163 Specdb::NmrOneD 9164 Specdb::NmrOneD 9165 Specdb::NmrOneD 9166 Specdb::NmrOneD 9167 Specdb::NmrOneD 9168 Specdb::NmrOneD 9169 Specdb::NmrOneD 9170 Specdb::NmrOneD 9171 Specdb::NmrOneD 9172 Specdb::NmrOneD 9173 Specdb::NmrOneD 9174 Specdb::NmrOneD 9175 Specdb::NmrOneD 9176 Specdb::NmrOneD 9177 Specdb::NmrOneD 9178 Specdb::NmrOneD 9179 Specdb::NmrOneD 9180 Specdb::NmrOneD 9181 Specdb::CMs 23516 Specdb::CMs 715027 Specdb::CMs 715028 Specdb::CMs 715029 Specdb::CMs 715030 Specdb::CMs 715031 Specdb::CMs 715032 Specdb::CMs 715033 Specdb::CMs 715034 Specdb::CMs 715035 Specdb::CMs 715036 Specdb::CMs 715037 Specdb::CMs 715038 Specdb::CMs 715039 Specdb::CMs 715040 Specdb::CMs 715041 Specdb::CMs 715042 Specdb::CMs 715043 Specdb::CMs 715044 Specdb::CMs 715045 Specdb::CMs 715046 Specdb::CMs 715047 Specdb::CMs 715048 Specdb::CMs 715049 Specdb::CMs 715050 HMDB01312 #<Reference:0x000055ce31dd0c48> 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