Diadenosine pentaphosphate (BioDeep_00000005391)

 

Secondary id: BioDeep_00001869415

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


{[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-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

化学式: C20H29N10O22P5 (916.0145984000001)
中文名称:
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 9.09%

分子结构信息

SMILES: C([C@@H]1[C@H]([C@H](C(n2cnc3c(N)ncnc23)O1)O)O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OCC1[C@H]([C@H]([C@H](n2cnc3c(N)ncnc23)O1)O)O
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

描述信息

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]
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).
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents

同义名列表

14 个代谢物同义名

{[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-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-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; ({[({[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate; [(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; P(1),P(5)-Di(adenosine-5-)pentaphosphate; P(1),P(5)-Bis(5-adenosyl)pentaphosphate; P1,P5-Bis(5-adenosyl) pentaphosphate; Diadenosine pentaphosphoric acid; Bis(adenosine)-5-pentaphosphate; Bis(5-adenosyl) pentaphosphate; Diadenosine pentaphosphate; Ap5a; BDBM86485; Bis(5'-adenosyl) pentaphosphate



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Maciej Ostrowski, Agnieszka Mierek-Adamska, Dorota Porowińska, Anna Goc, Anna Jakubowska. Cloning and biochemical characterization of indole-3-acetic acid-amino acid synthetase PsGH3 from pea. Plant physiology and biochemistry : PPB. 2016 Oct; 107(?):9-20. doi: 10.1016/j.plaphy.2016.05.031. [PMID: 27235647]
  • A Patzak, M Carlström, M M Sendeski, E Y Lai, Z Z Liu, J Sällström, J Flöge, B Heintz, J Jankowski, V Jankowski. Diadenosine pentaphosphate modulates glomerular arteriolar tone and glomerular filtration rate. Acta physiologica (Oxford, England). 2015 Jan; 213(1):285-93. doi: 10.1111/apha.12425. [PMID: 25394939]
  • Anna Schulz, Vera Jankowski, Walter Zidek, Joachim Jankowski. Highly sensitive, selective and rapid LC-MS method for simultaneous quantification of diadenosine polyphosphates in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jun; 961(?):91-6. doi: 10.1016/j.jchromb.2014.05.018. [PMID: 24869945]
  • Craig Beall, Kenneth R Watterson, Rory J McCrimmon, Michael L J Ashford. AMPK modulates glucose-sensing in insulin-secreting cells by altered phosphotransfer to KATP channels. Journal of bioenergetics and biomembranes. 2013 Jun; 45(3):229-41. doi: 10.1007/s10863-013-9509-9. [PMID: 23575945]
  • Hsing-Mao Chu, Feng-Yuan Chen, Tzu-Ping Ko, Andrew H-J Wang. Binding and catalysis of Humulus lupulus adenylate isopentenyltransferase for the synthesis of isopentenylated diadenosine polyphosphates. FEBS letters. 2010 Sep; 584(18):4083-8. doi: 10.1016/j.febslet.2010.08.038. [PMID: 20807533]
  • L Song, S M Carter, Y Chen, R Sitsapesan. Diadenosine pentaphosphate is a potent activator of cardiac ryanodine receptors revealing a novel high-affinity binding site for adenine nucleotides. British journal of pharmacology. 2009 Mar; 156(5):857-67. doi: 10.1111/j.1476-5381.2008.00071.x. [PMID: 19220293]
  • Gennady G Yegutkin, Joachim Jankowski, Sirpa Jalkanen, Thomas Günthner, Walter Zidek, Vera Jankowski. Dinucleotide polyphosphates contribute to purinergic signalling via inhibition of adenylate kinase activity. Bioscience reports. 2008 Aug; 28(4):189-94. doi: 10.1042/bsr20080052. [PMID: 18576946]
  • V Jankowski, S Karadogan, R Vanholder, J-R Nofer, S Herget-Rosenthal, M van der Giet, M Tölle, T N A Tran, W Zidek, J Jankowski. Paracrine stimulation of vascular smooth muscle proliferation by diadenosine polyphosphates released from proximal tubule epithelial cells. Kidney international. 2007 May; 71(10):994-1000. doi: 10.1038/sj.ki.5002186. [PMID: 17361116]
  • Joachim Jankowski, Vera Jankowski, Udo Laufer, Markus van der Giet, Lars Henning, Martin Tepel, Walter Zidek, Hartmut Schlüter. Identification and quantification of diadenosine polyphosphate concentrations in human plasma. Arteriosclerosis, thrombosis, and vascular biology. 2003 Jul; 23(7):1231-8. doi: 10.1161/01.atv.0000075913.00428.fd. [PMID: 12738682]
  • Joachim Jankowski, Hartmut Schlüter, Lars Henning, Markus van der Giet, Vera Jankowski, Walter Zidek, Martin Tepel. The AN69 hemofiltration membrane has a decreasing effect on the intracellular diadenosine pentaphosphate concentration of platelets. Kidney & blood pressure research. 2003; 26(1):50-4. doi: 10.1159/000069765. [PMID: 12697977]
  • Ivan Quesada, Juan M Rovira, Franz Martin, Enrique Roche, Angel Nadal, Bernat Soria. Nuclear KATP channels trigger nuclear Ca(2+) transients that modulate nuclear function. Proceedings of the National Academy of Sciences of the United States of America. 2002 Jul; 99(14):9544-9. doi: 10.1073/pnas.142039299. [PMID: 12089327]
  • Alex V Birk, Darya Bubman, M Johan Broekman, Hugh D Robertson, Joan H F Drosopoulos, Aaron J Marcus, Hazel H Szeto. Role of a novel soluble nucleotide phospho-hydrolase from sheep plasma in inhibition of platelet reactivity: hemostasis, thrombosis, and vascular biology. The Journal of laboratory and clinical medicine. 2002 Feb; 139(2):116-24. doi: 10.1067/mlc.2002.121334. [PMID: 11919550]
  • G Gabriëls, K Endlich, K H Rahn, E Schlatter, M Steinhausen. In vivo effects of diadenosine polyphosphates on rat renal microcirculation. Kidney international. 2000 Jun; 57(6):2476-84. doi: 10.1046/j.1523-1755.2000.00106.x. [PMID: 10844616]
  • J Jankowski, M Tepel, M van der Giet, I M Tente, L Henning, R Junker, W Zidek, H Schlüter. Identification and characterization of P(1), P(7)-Di(adenosine-5')-heptaphosphate from human platelets. The Journal of biological chemistry. 1999 Aug; 274(34):23926-31. doi: 10.1074/jbc.274.34.23926. [PMID: 10446159]
  • M van der Giet, O Cinkilic, J Jankowski, M Tepel, W Zidek, H Schlüter. Evidence for two different P2X-receptors mediating vasoconstriction of Ap5A and Ap6A in the isolated perfused rat kidney. British journal of pharmacology. 1999 Jul; 127(6):1463-9. doi: 10.1038/sj.bjp.0702667. [PMID: 10455297]
  • L Zhou, F Lacroute, R Thornburg. Cloning, expression in Escherichia coli, and characterization of Arabidopsis thaliana UMP/CMP kinase. Plant physiology. 1998 May; 117(1):245-54. doi: 10.1104/pp.117.1.245. [PMID: 9576794]
  • M Khattab, H Hohage, P Hollah, K H Rahn, E Schlatter. Effects of diadenosine polyphosphates on systemic and regional hemodynamics in anesthetized rats. Kidney & blood pressure research. 1998; 21(1):42-9. doi: 10.1159/000025842. [PMID: 9661136]
  • A Minelli, M Moroni, I Mezzasoma. Human seminal plasma soluble 5'-nucleotidase: regulatory aspects of the dephosphorylation of nucleoside 5'-monophosphates. Biochemical and molecular medicine. 1997 Jun; 61(1):95-101. doi: 10.1006/bmme.1997.2589. [PMID: 9232203]
  • J Mateo, P Rotllan, E Marti, I Gomez De Aranda, C Solsona, M T Miras-Portugal. Diadenosine polyphosphate hydrolase from presynaptic plasma membranes of Torpedo electric organ. The Biochemical journal. 1997 May; 323 ( Pt 3)(?):677-84. doi: 10.1042/bj3230677. [PMID: 9169600]
  • A Ogilvie, R Bläsius, E Schulze-Lohoff, R B Sterzel. Adenine dinucleotides: a novel class of signalling molecules. Journal of autonomic pharmacology. 1996 Dec; 16(6):325-8. doi: 10.1111/j.1474-8673.1996.tb00045.x. [PMID: 9131408]
  • H Hohage, C Reinhardt, U Borucki, G Enck, H Schlüter, E Schlatter, W Zidek. Effects of diadenosine polyphosphates on renal function and blood pressure in anesthetized Wistar rats. Journal of the American Society of Nephrology : JASN. 1996 Aug; 7(8):1216-22. doi: 10.1681/asn.v781216. [PMID: 8866415]
  • E Schlatter, I Ankorina, S Haxelmans, R Kleta. Effects of diadenosine polyphosphates, ATP and angiotensin II on cytosolic Ca2+ activity and contraction of rat mesangial cells. Pflugers Archiv : European journal of physiology. 1995 Sep; 430(5):721-8. doi: 10.1007/bf00386167. [PMID: 7478924]
  • H Schlüter, E Offers, G Brüggemann, M van der Giet, M Tepel, E Nordhoff, M Karas, C Spieker, H Witzel, W Zidek. Diadenosine phosphates and the physiological control of blood pressure. Nature. 1994 Jan; 367(6459):186-8. doi: 10.1038/367186a0. [PMID: 8114917]
  • V V Murthy. Adenylate kinase mimics creatine kinase-MM isoenzyme in a CK isoenzyme electrophoresis assay. Journal of clinical laboratory analysis. 1994; 8(3):140-3. doi: 10.1002/jcla.1860080305. [PMID: 8046541]
  • H Chen, A G McLennan. The bis(adenosin-N6-yl)alkanes, a family of potential dinucleoside-polyphosphate analogue precursors. Cytotoxicity, adenosine-receptor binding and metabolism. European journal of biochemistry. 1993 Jun; 214(3):935-44. doi: 10.1111/j.1432-1033.1993.tb17997.x. [PMID: 8391440]
  • T Fröhlich, B Reitter, D Scheffner, R H Schirmer, R Untucht-Grau. Muscle adenylate kinase in Duchenne muscular dystrophy. Biochimica et biophysica acta. 1986 Oct; 883(3):598-603. doi: 10.1016/0304-4165(86)90303-x. [PMID: 3019420]
  • D A Eppstein, B B Schryver, Y V Marsh. Stereoconfiguration markedly affects the biochemical and biological properties of phosphorothioate analogs of 2-5A core, (A2'p5')2A. The Journal of biological chemistry. 1986 May; 261(13):5999-6003. doi: 10.1016/s0021-9258(17)38484-3. [PMID: 3009440]
  • M Hamada, H Okuda, K Oka, T Watanabe, K Ueda, M Nojima, S A Kuby, M Manship, F H Tyler, F A Ziter. An aberrant adenylate kinase isoenzyme from the serum of patients with Duchenne muscular dystrophy. Biochimica et biophysica acta. 1981 Aug; 660(2):227-37. doi: 10.1016/0005-2744(81)90164-9. [PMID: 6269633]
  • M Mathieu, I Maire. Modification of a recommended method for the determination of catalytic concentration of creatine kinase in human serum at 30 degrees C (document C', stage 3). Annales de biologie clinique. 1980; 38(3):191-7. doi: NULL. [PMID: 6778266]