2.0 2012-08-09 09:16:13 -0600 2015-06-03 17:21:29 -0600 ECMDB21431 M2MDB001826 Diadenosine triphosphate Diadenosine triphosphate (AP3A) is a species of diadenosine polyphosphate (ApnA), consisting of two adenosines joined by a chain of phosphates. (inferred from compound structure) In E. coli, AP3A can be produced from ATP and ADP in a reaction catalyzed by AP3A synthetase, which is encoded by the gene lysU. (EcoCyc). These dinucleotides have been proposed to act as modulators of the heat-shock response and stress response. 5'Ap3A Adenosine (5')triphospho(5')adenosine Adenosine 5'-(tetrahydrogen triphosphate), P''-5'-ester with adenosine Adenosine 5'-(tetrahydrogen triphosphoric acid), p''-5'-ester with adenosine Adenosine 5'-triphosphate 5'-adenosine Adenosine 5'-triphosphoric acid 5'-adenosine Adenosine(3)triphosphate adenosine Adenosine(3)triphosphoric acid adenosine Adenosine(5')triphospho(5')adenosine Ap3a Ap₃A BIS(ADENOSINE)-5'-TRIPHOSPHATE BIS(adenosine)-5'-triphosphoric acid Diadenosine triphosphate Diadenosine triphosphoric acid P(1),P(3)-bis(5'-adenosyl) trihydrogen triphosphate P(1),P(3)-Bis(5'-adenosyl) trihydrogen triphosphoric acid P(1),P(3)-bis(5'-adenosyl) triphosphate P(1),P(3)-Bis(5'-adenosyl) triphosphoric acid P(1)-P(3)-bis(5'-adenosyl) triphosphate P(1)-P(3)-Bis(5'-adenosyl) triphosphoric acid P1,P3-Bis(5'-adenosyl) triphosphate P1,P3-Bis(5'-adenosyl) triphosphoric acid P1,P3-bis(5'-adenosyl)triphosphate P1,P3-Bis(5'-adenosyl)triphosphoric acid C20H27N10O16P3 756.4071 756.081934402 {[(2S,3R,4S,5S)-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)phosphinic acid [(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphinic acid 56432-02-1 NC1=C2N=CN([C@H]3O[C@@H](COP(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/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)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)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+ QCICUPZZLIQAPA-WGIMJHEJSA-N Solid logp -1.26 ALOGPS logs -2.24 ALOGPS solubility 4.39e+00 g/l ALOGPS logp -9.1 ChemAxon pka_strongest_acidic 0.91 ChemAxon pka_strongest_basic 5.29 ChemAxon iupac {[(2S,3R,4S,5S)-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)phosphinic acid ChemAxon average_mass 756.4071 ChemAxon mono_mass 756.081934402 ChemAxon smiles NC1=C2N=CN([C@H]3O[C@@H](COP(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 C20H27N10O16P3 ChemAxon inchi InChI=1S/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)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)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+ ChemAxon inchikey QCICUPZZLIQAPA-WGIMJHEJSA-N ChemAxon polar_surface_area 387.44 ChemAxon refractivity 155.23 ChemAxon polarizability 62.1 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 20 ChemAxon donor_count 9 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic Specdb::CMs 71828 Specdb::CMs 780373 Specdb::CMs 780374 Specdb::CMs 780375 Specdb::CMs 780376 Specdb::CMs 780377 Specdb::CMs 780378 Specdb::CMs 780379 Specdb::CMs 780380 Specdb::CMs 780381 Specdb::CMs 780382 Specdb::CMs 780383 Specdb::CMs 780384 Specdb::CMs 780385 Specdb::CMs 780386 Specdb::CMs 780387 Specdb::CMs 780388 Specdb::CMs 780389 Specdb::CMs 780390 Specdb::NmrOneD 8782 Specdb::NmrOneD 8783 Specdb::NmrOneD 8784 Specdb::NmrOneD 8785 Specdb::NmrOneD 8786 Specdb::NmrOneD 8787 Specdb::NmrOneD 8788 Specdb::NmrOneD 8789 Specdb::NmrOneD 8790 Specdb::NmrOneD 8791 Specdb::NmrOneD 8792 Specdb::NmrOneD 8793 Specdb::NmrOneD 8794 Specdb::NmrOneD 8795 Specdb::NmrOneD 8796 Specdb::NmrOneD 8797 Specdb::NmrOneD 8798 Specdb::NmrOneD 8799 Specdb::NmrOneD 8800 Specdb::NmrOneD 8801 Specdb::MsMs 23654 Specdb::MsMs 23655 Specdb::MsMs 23656 Specdb::MsMs 30452 Specdb::MsMs 30453 Specdb::MsMs 30454 Specdb::MsMs 2266605 Specdb::MsMs 2266606 Specdb::MsMs 2266607 Specdb::MsMs 3075777 Specdb::MsMs 3075778 Specdb::MsMs 3075779 HMDB01155 165381 C06197 27775 ADENOSINE5TRIPHOSPHO5ADENOSINE van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Hollah P, Hausberg M, Kosch M, Barenbrock M, Letzel M, Schlatter E, Rahn KH: A novel assay for determination of diadenosine polyphosphates in human platelets: studies in normotensive subjects and in patients with essential hypertension. J Hypertens. 2001 Feb;19(2):237-45. 11212966 Pintor J, Carracedo G, Alonso MC, Bautista A, Peral A: Presence of diadenosine polyphosphates in human tears. Pflugers Arch. 2002 Jan;443(3):432-6. Epub 2001 Aug 23. 11810214 Jankowski J, Jankowski V, Laufer U, van der Giet M, Henning L, Tepel M, Zidek W, Schluter H: Identification and quantification of diadenosine polyphosphate concentrations in human plasma. Arterioscler Thromb Vasc Biol. 2003 Jul 1;23(7):1231-8. 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Ital J Biochem. 2003 Mar;52(1):9-16. 12833632 Kowara R, Karaczyn AA, Fivash MJ Jr, Kasprzak KS: In vitro inhibition of the enzymatic activity of tumor suppressor FHIT gene product by carcinogenic transition metals. Chem Res Toxicol. 2002 Mar;15(3):319-25. 11896678 Lysyl-tRNA synthetase, heat inducible P0A8N5 SYK2_ECOLI lysU http://ecmdb.ca/proteins/P0A8N5.xml Hydrogen ion + Adenosine triphosphate + ADP > Diadenosine triphosphate + Pyrophosphate RXN0-5209