PA(16:0/18:1(9Z)) (BioDeep_00000019584)

Main id: BioDeep_00000009643

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


9-Octadecenoic acid (Z)-, 1-[[(1-oxohexadecyl)oxy]methyl]-2-(phosphonooxy)ethyl ester, (R)-

化学式: C37H71O8P (674.4886)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCC=CCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O
InChI: InChI=1S/C37H71O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/t35-/m1/s1

描述信息

PA(16:0/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-coA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). [HMDB]
PA(16:0/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776).

同义名列表

28 个代谢物同义名

9-Octadecenoic acid (Z)-, 1-[[(1-oxohexadecyl)oxy]methyl]-2-(phosphonooxy)ethyl ester, (R)-; [(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid; (2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoic acid; (2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid; (2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoate; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphoric acid; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoric acid; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphate; 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidic acid; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidate; 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphate; Phosphatidic acid(16:0/18:1omega9); Phosphatidate(16:0/18:1OMEGA9); Phosphatidic acid(16:0/18:1W9); Phosphatidic acid(16:0/18:1n9); Phosphatidic acid(16:0/18:1); Phosphatidate(16:0/18:1); Phosphatidic acid(34:1); Phosphatidate(34:1); PA(16:0/18:1OMEGA9); PA(16:0/18:1(9Z)); PA(16:0/18:1W9); PA(16:0/18:1N9); PA(16:0/18:1); PA(16:0_18:1); PA(34:1); PA 34:1



数据库引用编号

14 个数据库交叉引用编号

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代谢反应

546 个相关的代谢反应过程信息。

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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。

亚细胞结构定位 关联基因列表


文献列表

  • Ellen M Muehl, Joshua M Gajsiewicz, Sara M Medfisch, Zachary S B Wiersma, James H Morrissey, Ryan C Bailey. Multiplexed silicon photonic sensor arrays enable facile characterization of coagulation protein binding to nanodiscs with variable lipid content. The Journal of biological chemistry. 2017 09; 292(39):16249-16256. doi: 10.1074/jbc.m117.800938. [PMID: 28801460]
  • N V Surovtsev, N V Ivanisenko, K Yu Kirillov, S A Dzuba. Low-temperature dynamical and structural properties of saturated and monounsaturated phospholipid bilayers revealed by Raman and spin-label EPR spectroscopy. The journal of physical chemistry. B. 2012 Jul; 116(28):8139-44. doi: 10.1021/jp3038895. [PMID: 22721271]
  • Yassar Farooq, Gordon C K Roberts. Kinetics of electron transfer between NADPH-cytochrome P450 reductase and cytochrome P450 3A4. The Biochemical journal. 2010 Dec; 432(3):485-93. doi: 10.1042/bj20100744. [PMID: 20879989]
  • Sonia Sánchez-Bautista, Senena Corbalán-García, Angel Pérez-Lara, Juan C Gómez-Fernández. A comparison of the membrane binding properties of C1B domains of PKCgamma, PKCdelta, and PKCepsilon. Biophysical journal. 2009 May; 96(9):3638-47. doi: 10.1016/j.bpj.2009.02.021. [PMID: 19413969]
  • Robert Bussell, David Eliezer. Effects of Parkinson's disease-linked mutations on the structure of lipid-associated alpha-synuclein. Biochemistry. 2004 Apr; 43(16):4810-8. doi: 10.1021/bi036135+. [PMID: 15096050]
  • Sosaku Ichikawa, Peter Walde. Phospholipase D-mediated aggregation, fusion, and precipitation of phospholipid vesicles. Langmuir : the ACS journal of surfaces and colloids. 2004 Feb; 20(3):941-9. doi: 10.1021/la030357r. [PMID: 15773127]
  • L A Bagatolli, D D Binns, D M Jameson, J P Albanesi. Activation of dynamin II by POPC in giant unilamellar vesicles: a two-photon fluorescence microscopy study. Journal of protein chemistry. 2002 Aug; 21(6):383-91. doi: 10.1023/a:1021126415320. [PMID: 12492148]
  • R N Lewis, R N McElhaney. Surface charge markedly attenuates the nonlamellar phase-forming propensities of lipid bilayer membranes: calorimetric and (31)P-nuclear magnetic resonance studies of mixtures of cationic, anionic, and zwitterionic lipids. Biophysical journal. 2000 Sep; 79(3):1455-64. doi: 10.1016/s0006-3495(00)76397-1. [PMID: 10969007]
  • Z Salamon, G Lindblom, L Rilfors, K Linde, G Tollin. Interaction of phosphatidylserine synthase from E. coli with lipid bilayers: coupled plasmon-waveguide resonance spectroscopy studies. Biophysical journal. 2000 Mar; 78(3):1400-12. doi: 10.1016/s0006-3495(00)76693-8. [PMID: 10692325]
  • K Stieglitz, B Seaton, M F Roberts. The role of interfacial binding in the activation of Streptomyces chromofuscus phospholipase D by phosphatidic acid. The Journal of biological chemistry. 1999 Dec; 274(50):35367-74. doi: 10.1074/jbc.274.50.35367. [PMID: 10585404]
  • W S Davidson, A Jonas, D F Clayton, J M George. Stabilization of alpha-synuclein secondary structure upon binding to synthetic membranes. The Journal of biological chemistry. 1998 Apr; 273(16):9443-9. doi: 10.1074/jbc.273.16.9443. [PMID: 9545270]