Diadenosine triphosphate (BioDeep_00000006087)
Secondary id: BioDeep_00001869672
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
化学式: C20H27N10O16P3 (756.0819)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 84.29%
分子结构信息
SMILES: C([C@H]1[C@@H]([C@@H]([C@@H](n2cnc3c(N)ncnc23)O1)O)O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](n2cnc3c(N)ncnc23)O1)O)O
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)
描述信息
Diadenosine triphosphate (AP3A) 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. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A 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. AP3A accumulates in cells in response to various physiological factors. AP3A FHIT (Fragile histidine Triad) is a human tumor suppressor gene. The Fhit protein is believed to inhibit tumor growth by inducing apoptosis through interaction with AP3A. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 12833632, 11896678).
Diadenosine triphosphate (AP3A) 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. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A 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. AP3A accumulates in cells in response to various physiological factors.
同义名列表
19 个代谢物同义名
{[(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; p(1),p(3)-Bis(5-adenosyl) trihydrogen triphosphate; p(1),p(3)-Bis(5-adenosyl) triphosphate; p(1)-p(3)-Bis(5-adenosyl) triphosphate; p(1),(P3)-Bis(5-adenosyl)triphosphate; Adenosine 5-triphosphate 5-adenosine; Adenosine (5)triphospho(5)adenosine; Adenosine(3)triphosphate adenosine; P1,P3-Bis(5-adenosyl) triphosphate; Adenosine(5)triphospho(5)adenosine; Diadenosine triphosphoric acid; Bis(adenosine)-5-triphosphate; Diadenosine triphosphate; AC1L1AGT; ApppA; 5Ap3a; Ap3a; P1,P3-Bis(5'-adenosyl) triphosphate
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:27775
- KEGG: C06197
- PubChem: 14464643
- PubChem: 165381
- PubChem: 982
- HMDB: HMDB0001155
- Metlin: METLIN6244
- DrugBank: DB01690
- ChEMBL: CHEMBL407938
- foodb: FDB022454
- CAS: 158700-26-6
- CAS: 56432-02-1
- CAS: 5959-90-0
- PMhub: MS000019047
- PubChem: 8447
- PDB-CCD: BA3
- 3DMET: B01993
- NIKKAJI: J398.258K
- RefMet: Diadenosine triphosphate
- KNApSAcK: 27775
- LOTUS: LTS0089364
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)
9 个相关的物种来源信息
- 7711 - Chordata: LTS0089364
- 2759 - Eukaryota: LTS0089364
- 9606 - Homo sapiens: -
- 40674 - Mammalia: LTS0089364
- 33208 - Metazoa: LTS0089364
- 10066 - Muridae: LTS0089364
- 10088 - Mus: LTS0089364
- 10090 - Mus musculus: LTS0089364
- 10090 - Mus musculus: NA
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
- Anita Śliwińska, Marcin R Naliwajski, Agnieszka Pietrosiuk, Katarzyna Sykłowska-Baranek. In Vitro Response of Polyscias filicifolia (Araliaceae) Shoots to Elicitation with Alarmone-Diadenosine Triphosphate, Methyl Jasmonate, and Salicylic Acid.
Cells.
2021 02; 10(2):. doi:
10.3390/cells10020419. [PMID: 33671225] - Małgorzata Pietrowska-Borek, Łukasz Czekała, Sarai Belchí-Navarro, María Angeles Pedreño, Andrzej Guranowski. Diadenosine triphosphate is a novel factor which in combination with cyclodextrins synergistically enhances the biosynthesis of trans-resveratrol in Vitis vinifera cv. Monastrell suspension cultured cells.
Plant physiology and biochemistry : PPB.
2014 Nov; 84(?):271-276. doi:
10.1016/j.plaphy.2014.09.019. [PMID: 25310254] - 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] - David G Watson, Francesca Tonelli, Manal Alossaimi, Leon Williamson, Edmond Chan, Irina Gorshkova, Evgeny Berdyshev, Robert Bittman, Nigel J Pyne, Susan Pyne. The roles of sphingosine kinases 1 and 2 in regulating the Warburg effect in prostate cancer cells.
Cellular signalling.
2013 Apr; 25(4):1011-7. doi:
10.1016/j.cellsig.2013.01.002. [PMID: 23314175] - Ronald A Albright, William C Chang, Donna Robert, Deborah L Ornstein, Wenxiang Cao, Lynn Liu, Meredith E Redick, J Isaac Young, Enrique M De La Cruz, Demetrios T Braddock. NPP4 is a procoagulant enzyme on the surface of vascular endothelium.
Blood.
2012 Nov; 120(22):4432-40. doi:
10.1182/blood-2012-04-425215. [PMID: 22995898] - Eva Schepers, Griet Glorieux, Vera Jankowski, Annemieke Dhondt, Joachim Jankowski, Raymond Vanholder. Dinucleoside polyphosphates: newly detected uraemic compounds with an impact on leucocyte oxidative burst.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2010 Aug; 25(8):2636-44. doi:
10.1093/ndt/gfq080. [PMID: 20190246] - Kamil Olejnik, Monika W Murcha, James Whelan, Elzbieta Kraszewska. Cloning and characterization of AtNUDT13, a novel mitochondrial Arabidopsis thaliana Nudix hydrolase specific for long-chain diadenosine polyphosphates.
The FEBS journal.
2007 Sep; 274(18):4877-85. doi:
10.1111/j.1742-4658.2007.06009.x. [PMID: 17824959] - Andrzej Guranowski, Otto Miersch, Paul E Staswick, Walter Suza, Claus Wasternack. Substrate specificity and products of side-reactions catalyzed by jasmonate:amino acid synthetase (JAR1).
FEBS letters.
2007 Mar; 581(5):815-20. doi:
10.1016/j.febslet.2007.01.049. [PMID: 17291501] - Andrea Vecchione, Tommaso Prayer Galetti, Marina Gardiman, Hideshi Ishii, Enrico Giarnieri, Francesco Pagano, Leonard G Gomella, Carlo M Croce, Raffaele Baffa. Collecting duct carcinoma of the kidney: an immunohistochemical study of 11 cases.
BMC urology.
2004 Sep; 4(?):11. doi:
10.1186/1471-2490-4-11. [PMID: 15357873] - 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] - Michael Kron, Michael Petridis, Youli Milev, Joseph Leykam, Michael Härtlein. Expression, localization and alternative function of cytoplasmic asparaginyl-tRNA synthetase in Brugia malayi.
Molecular and biochemical parasitology.
2003 Jun; 129(1):33-9. doi:
10.1016/s0166-6851(03)00080-x. [PMID: 12798504] - A Minelli, L Liguori, I Bellezza, T Renieri, C Castellini. Effects of diadenosine polyphosphates and seminal fluid vesicles on rabbit sperm cells.
Reproduction (Cambridge, England).
2003 Jun; 125(6):827-35. doi:
10.1530/rep.0.1250827. [PMID: 12773105] - Sang-Han Lee, Tae-Jung Kim, Ho-Young Kim, Jin-Gook Kim, Mi-Kyoung Park, Kee-Min Woo, Sung-Ho Kim, Kyu-Yoon Hwang, Hae-Seon Nam, Young-Ki Min, Man-Hee Cho. Expression of the fragile histidine triad gene in normal rat tissues and human kidney cancer cell lines.
Research communications in molecular pathology and pharmacology.
2002; 112(1-4):145-57. doi:
. [PMID: 15080505] - H M Abdelghany, L Gasmi, J L Cartwright, S Bailey, J B Rafferty, A G McLennan. Cloning, characterisation and crystallisation of a diadenosine 5',5"'-P(1),P(4)-tetraphosphate pyrophosphohydrolase from Caenorhabditis elegans.
Biochimica et biophysica acta.
2001 Nov; 1550(1):27-36. doi:
10.1016/s0167-4838(01)00263-1. [PMID: 11738085] - 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] - 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] - E Busshardt, W Gerok, D Häussinger. Regulation of hepatic parenchymal and non-parenchymal cell function by the diadenine nucleotides Ap3A and Ap4A.
Biochimica et biophysica acta.
1989 Feb; 1010(2):151-9. doi:
10.1016/0167-4889(89)90155-9. [PMID: 2563228] - J Lüthje, A Ogilvie. Catabolism of Ap4A and Ap3A in whole blood. The dinucleotides are long-lived signal molecules in the blood ending up as intracellular ATP in the erythrocytes.
European journal of biochemistry.
1988 Apr; 173(1):241-5. doi:
10.1111/j.1432-1033.1988.tb13990.x. [PMID: 3356191] - J Lüthje, A Ogilvie. Catabolism of Ap4A and Ap3A in human serum. Identification of isoenzymes and their partial characterization.
European journal of biochemistry.
1987 Dec; 169(2):385-8. doi:
10.1111/j.1432-1033.1987.tb13624.x. [PMID: 2826143] - J Lüthje, D Miller, A Ogilvie. Unproportionally high concentrations of diadenosine triphosphate (Ap3A) and diadenosine tetraphosphate (Ap4A) in heavy platelets. Consequences for in vitro studies with human platelets.
Blut.
1987 Apr; 54(4):193-200. doi:
10.1007/bf00594193. [PMID: 3030468] - J Lüthje, J Baringer, A Ogilvie. Effects of diadenosine triphosphate (Ap3A) and diadenosine tetraphosphate (Ap4A) on platelet aggregation in unfractionated human blood.
Blut.
1985 Dec; 51(6):405-13. doi:
10.1007/bf00320727. [PMID: 3852686] - J Lüthje, J Baringer, A Ogilvie. Highly efficient induction of human platelet aggregation in heparinized platelet-rich plasma by diadenosine triphosphate (Ap3A).
Thrombosis and haemostasis.
1985 Aug; 54(2):469-71. doi:
. [PMID: 4082083] - J Lüthje, A Ogilvie. Catabolism of Ap3A and Ap4A in human plasma. Purification and characterization of a glycoprotein complex with 5'-nucleotide phosphodiesterase activity.
European journal of biochemistry.
1985 May; 149(1):119-27. doi:
10.1111/j.1432-1033.1985.tb08901.x. [PMID: 2986968] - J Lüthje, A Ogilvie. Diadenosine triphosphate (Ap3A) mediates human platelet aggregation by liberation of ADP.
Biochemical and biophysical research communications.
1984 Feb; 118(3):704-9. doi:
10.1016/0006-291x(84)91451-7. [PMID: 6704102]
