2.0 2012-05-31 13:47:46 -0600 2015-06-03 15:53:51 -0600 ECMDB01211 M2MDB000300 Diadenosine tetraphosphate Diadenosine tetraphosphate (AP4A) is a diadenosine polyphosphate. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. 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. It is an intermediate of purine metabolism pathway. 5',5'''-Diadenosine tetraphosphate 5',5'''-diadenosine tetraphosphoric acid Adenosine 5'-tetraphosphate, 5'-ester with adenosine Adenosine 5'-tetraphosphoric acid, 5'-ester with adenosine Adenosine-(5')-tetraphospho-(5')-adenosine Ap4A Ap₄A AppppA Diadenosine 5',5'''-P1,P4-tetraphosphate Diadenosine 5',5'''-P1,P4-tetraphosphoric acid Diadenosine tetraphosphoric acid P(1),P(4)-Bis(5'-adenosyl)tetraphosphate P(1),P(4)-Bis(5'-adenosyl)tetraphosphoric acid P1,P4-bis(5'-adenosyl)tetraphosphate P1,P4-Bis(5'-adenosyl)tetraphosphoric acid P1,P4-Di(adenosin-5'-yl)tetraphosphate P1,P4-Di(adenosin-5'-yl)tetraphosphoric acid P1,P4-Diadenosine-5'-tetraphosphate P1,P4-Diadenosine-5'-tetraphosphoric acid P¹,P⁴-bis(5'-adenosyl)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 Solid Cytosol 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 Purine metabolism ec00230 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 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 HMDB01211 21706 20402 C01260 17422 ADENOSYL-P4 B4P Keseler, I. 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Arch Androl. 1991 Sep-Oct;27(2):103-8. 1953194 Bis(5'-nucleosyl)-tetraphosphatase [symmetrical] P05637 APAH_ECOLI apaH http://ecmdb.ca/proteins/P05637.xml Lysyl-tRNA synthetase, heat inducible P0A8N5 SYK2_ECOLI lysU http://ecmdb.ca/proteins/P0A8N5.xml Diadenosine tetraphosphate + Water <>2 ADP +2 Hydrogen ion R00125 3.6.1.41-RXN 2 Adenosine triphosphate + Hydrogen ion > Diadenosine tetraphosphate + Pyrophosphate RXN0-5208 Diadenosine tetraphosphate + Water <>2 ADP R00125 3.6.1.41-RXN Water + Diadenosine tetraphosphate > Hydrogen ion + ADP 3.6.1.41-RXN Hydrogen ion + Adenosine triphosphate + Adenosine triphosphate Diadenosine tetraphosphate + Pyrophosphate RXN0-5208 Diadenosine tetraphosphate + Water >2 ADP Diadenosine tetraphosphate + Water <>2 ADP +2 Hydrogen ion