Phosphoethanolamine (BioDeep_00000001725)

 

Secondary id: BioDeep_00000400027, BioDeep_00000400059, BioDeep_00000402855, BioDeep_00000405223

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


2-Aminoethyl dihydrogen phosphate (acd/name 4.0)

化学式: C2H8NO4P (141.0190938)
中文名称: O-磷酸乙醇胺, 乙醇胺磷酸酯, 磷酸乙醇胺, 2-氨基乙基磷酸二氢盐
谱图信息: 最多检出来源 Homo sapiens(blood) 0.06%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Phosphoethanolamine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phosphoethanolamine (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000001725). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(COP(=O)(O)O)N
InChI: InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

描述信息

O-Phosphoethanolamine, also known as PEA, phosphorylethanolamine, colamine phosphoric acid or ethanolamine O-phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine is used in the biosynthesis of two different types of phospholipids: glycerophospholipids and sphingolipids. O-Phosphoethanolamine exists in all living species, ranging from bacteria to plants to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine; which is mediated by the enzyme ethanolamine-phosphate cytidylyltransferase. In addition, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, O-phosphoethanolamine is involved in phosphatidylcholine biosynthesis. O-phosphoethanolamine is also a product of the metabolism of sphingolipids. In particular, sphinglipids are metabolized in vivo to phosphorylethanolamine and a fatty aldehyde, generally palmitaldehyde. Both metabolites are ultimately converted to glycerophospholipids. The lipids are first phosphorylated by a kinase and then cleaved by the pyridoxal-dependent sphinganine-1-phosphate aldolase. Elevated urine levels of O-Phosphoethanolamine or PEA can be used to help in the diagnosis of Hypophosphatasia (HPP). Reference ranges for urinary PEA vary according to age and somewhat by diet, and follow a circadian rhythm. Outside of the human body, O-phosphoethanolamine has been detected, but not quantified in, several different foods, such as oxheart cabbages, anises, shiitakes, abalones, and teffs.
Phosphoryl-ethanolamine, also known as colamine phosphoric acid or ethanolamine phosphate, is a member of the class of compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. Phosphoryl-ethanolamine is soluble (in water) and a moderately acidic compound (based on its pKa). Phosphoryl-ethanolamine can be found in a number of food items such as pepper (capsicum), black salsify, cascade huckleberry, and redcurrant, which makes phosphoryl-ethanolamine a potential biomarker for the consumption of these food products. Phosphoryl-ethanolamine can be found primarily in most biofluids, including cerebrospinal fluid (CSF), blood, saliva, and feces. Phosphoryl-ethanolamine exists in all living species, ranging from bacteria to humans. In humans, phosphoryl-ethanolamine is involved in several metabolic pathways, some of which include phosphatidylethanolamine biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), phosphatidylethanolamine biosynthesis PE(14:0/20:1(11Z)), phosphatidylethanolamine biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)), and phosphatidylethanolamine biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)). Phosphoryl-ethanolamine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, phosphoryl-ethanolamine is found to be associated with traumatic brain injury.
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID E009
Phosphorylethanolamine is an endogenous metabolite.
Phosphorylethanolamine is an endogenous metabolite.

同义名列表

53 个代谢物同义名

2-Aminoethyl dihydrogen phosphate (acd/name 4.0); Phosphorylethanolamine, cobalt (2+) (1:1) salt; 2-Amino-ethanol dihydrogen phosphate (ester); Phosphorylethanolamine magnesium (1:1) salt; 2-Amino-ethanol dihydrogen phosphoric acid; Phosphoric acid 2-aminoethyl phenyl ester; Phosphorylethanolamine, 3H-labeled CPD; 2-Amino-ethanol dihydrogen phosphate; Phosphorylethanolamine ca (1:1) salt; Phosphate 2-aminoethyl phenyl ester; mono(2-Aminoethyl) phosphoric acid; Ethanolamine acid phosphoric acid; 2-Aminoethyl dihydrogen phosphate; Phosphorylethanolamine zinc salt; Calcium 2-aminoethanol phosphate; 2-Amino-ethanol phosphoric acid; Ethanolamine O-phosphoric acid; Monoaminoethyl phosphoric acid; (2-aminoethoxy)phosphonic acid; Ethanolamine phosphoric acid; mono(2-Aminoethyl) phosphate; Ethanolamine acid phosphate; 2-Aminoethanol O-phosphate; 2-Amino-ethanol phosphate; O-Phosphonatoethanaminium; O-PHOSPHORYLETHANOLAMINE; Monoaminoethyl phosphate; Colamine phosphoric acid; Ethanolamine O-phosphate; Colaminephosphoric acid; Phosphoryl-ethanolamine; Colamine acid phosphate; Phosphorylethanolamine; Colaminphosphoric acid; 2-Aminoethyl phosphate; Ethanolamine phosphate; O-Phosphoethanolamine; Phosphoryethanolamine; Phosphonoethanolamine; Phosphoethanolamine; Colamine phosphate; O-Phosphocolamine; Colaminphosphate; Ethamp; PETN; OPE; PEA; EAP; PE; O-Phosphoethanolamine; NSC 254167; Ethanolamine phosphate; 2-Aminoethyl dihydrogen phosphate



数据库引用编号

33 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(3)

PlantCyc(0)

代谢反应

5333 个相关的代谢反应过程信息。

Reactome(120)

BioCyc(10)

WikiPathways(9)

Plant Reactome(312)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(4882)

PharmGKB(0)

2 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

  • Khaled Tighanimine, José Américo Nabuco Leva Ferreira Freitas, Ivan Nemazanyy, Alexia Bankolé, Delphine Benarroch-Popivker, Susanne Brodesser, Gregory Doré, Lucas Robinson, Paule Benit, Sophia Ladraa, Yara Bou Saada, Bertrand Friguet, Philippe Bertolino, David Bernard, Guillaume Canaud, Pierre Rustin, Eric Gilson, Oliver Bischof, Stefano Fumagalli, Mario Pende. A homoeostatic switch causing glycerol-3-phosphate and phosphoethanolamine accumulation triggers senescence by rewiring lipid metabolism. Nature metabolism. 2024 Feb; 6(2):323-342. doi: 10.1038/s42255-023-00972-y. [PMID: 38409325]
  • Carmen García-Montoya, Diego Heras-Márquez, Rafael Amigot-Sánchez, Sara García-Linares, Álvaro Martínez-Del-Pozo, Juan Palacios-Ortega. Sticholysin recognition of ceramide-phosphoethanolamine. Archives of biochemistry and biophysics. 2023 07; 742(?):109623. doi: 10.1016/j.abb.2023.109623. [PMID: 37207934]
  • Xuejin Zhang, Leonor Sicalo Gianechini, Kun Li, Ray M Kaplan, William H Witola. Broad-Spectrum Inhibitors for Conserved Unique Phosphoethanolamine Methyltransferases in Parasitic Nematodes Possess Anthelmintic Efficacy. Antimicrobial agents and chemotherapy. 2023 06; 67(6):e0000823. doi: 10.1128/aac.00008-23. [PMID: 37212658]
  • Linda M Westermann, Ian D E A Lidbury, Chun-Yang Li, Ning Wang, Andrew R J Murphy, Maria Del Mar Aguilo Ferretjans, Mussa Quareshy, Muralidharan Shanmugan, Alberto Torcello-Requena, Eleonora Silvano, Yu-Zhong Zhang, Claudia A Blindauer, Yin Chen, David J Scanlan. Bacterial catabolism of membrane phospholipids links marine biogeochemical cycles. Science advances. 2023 04; 9(17):eadf5122. doi: 10.1126/sciadv.adf5122. [PMID: 37126561]
  • Masafumi Sakuma, Masahito Hashimoto, Kanako Nishi, Mari Tohya, Tomomi Hishinuma, Masahiro Shimojima, Tatsuya Tada, Teruo Kirikae. Emergence of colistin-resistant Acinetobacter modestus harbouring the intrinsic phosphoethanolamine transferase EptA. Journal of global antimicrobial resistance. 2023 Mar; 33(?):101-108. doi: 10.1016/j.jgar.2023.02.023. [PMID: 36906175]
  • Priscilla Pushparani Victor, Radhakrishnan Narayanaswamy, Seifedine Kadry, Baskar Gurunathan. Identification of novel inhibitor against Human Phosphoethanolamine Cytidylyl transferase from phytochemicals of Citrus sinensis peel extract by in vitro and in silico approach. Biotechnology and applied biochemistry. 2023 Feb; ?(?):. doi: 10.1002/bab.2453. [PMID: 36824047]
  • Hu Xu, Weizu Li, Lei Huang, Xinyu He, Bei Xu, Xueqing He, Wentong Chen, Yaoxing Wang, Wenjun Xu, Sheng Wang, Qin Kong, Youzhi Xu, Wenjie Lu. Phosphoethanolamine cytidyltransferase ameliorates mitochondrial function and apoptosis in hepatocytes in T2DM in vitro. Journal of lipid research. 2023 Jan; ?(?):100337. doi: 10.1016/j.jlr.2023.100337. [PMID: 36716821]
  • Alex Bare, Jaime Thomas, Daniel Etoroma, Soon Goo Lee. Functional analysis of phosphoethanolamine N-methyltransferase in plants and parasites: Essential S-adenosylmethionine-dependent methyltransferase in choline and phospholipid metabolism. Methods in enzymology. 2023; 680(?):101-137. doi: 10.1016/bs.mie.2022.08.028. [PMID: 36710008]
  • Ahmed Gaballa, Martin Wiedmann, Laura M Carroll. More than mcr: canonical plasmid- and transposon-encoded mobilized colistin resistance genes represent a subset of phosphoethanolamine transferases. Frontiers in cellular and infection microbiology. 2023; 13(?):1060519. doi: 10.3389/fcimb.2023.1060519. [PMID: 37360531]
  • Hiroshi Takahashi, Tomohiro Hayakawa, Asami Makino, Kunihiko Iwamoto, Kazuki Ito, Satoshi B Sato, Toshihide Kobayashi. Long chain ceramides raise the main phase transition of monounsaturated phospholipids to physiological temperature. Scientific reports. 2022 12; 12(1):20803. doi: 10.1038/s41598-022-25330-y. [PMID: 36460753]
  • Qi Qian, Yanhua Gao, Ge Xun, Xu Wang, Jiachen Ge, Huaxing Zhang, Feifei Mou, Suwen Su, Qiao Wang. Synchronous Investigation of the Mechanism and Substance Basis of Tripterygium Glycosides Tablets on Anti-rheumatoid Arthritis and Hepatotoxicity. Applied biochemistry and biotechnology. 2022 Nov; 194(11):5333-5352. doi: 10.1007/s12010-022-04011-6. [PMID: 35763252]
  • Qi Yu He, Jian Feng Jin, He Qiang Lou, Feng Feng Dang, Ji Ming Xu, Shao Jian Zheng, Jian Li Yang. Abscisic acid-dependent PMT1 expression regulates salt tolerance by alleviating abscisic acid-mediated reactive oxygen species production in Arabidopsis. Journal of integrative plant biology. 2022 Sep; 64(9):1803-1820. doi: 10.1111/jipb.13326. [PMID: 35789105]
  • Christopher Mullally, Keith A Stubbs, Van C Thai, Anandhi Anandan, Stephanie Bartley, Martin J Scanlon, Gary A Jarvis, Constance M John, Katherine Y L Lim, Courtney M Sullivan, Mitali Sarkar-Tyson, Alice Vrielink, Charlene M Kahler. Novel small molecules that increase the susceptibility of Neisseria gonorrhoeae to cationic antimicrobial peptides by inhibiting lipid A phosphoethanolamine transferase. The Journal of antimicrobial chemotherapy. 2022 08; 77(9):2441-2447. doi: 10.1093/jac/dkac204. [PMID: 35770844]
  • Sukrit Srisakul, Dhammika Leshan Wannigama, Paul G Higgins, Cameron Hurst, Shuichi Abe, Parichart Hongsing, Thammakorn Saethang, Sirirat Luk-In, Tingting Liao, Naris Kueakulpattana, Aye Mya Sithu Shein, Lin Gan, Rosalyn Kupwiwat, Chanikan Tanasatitchai, Pattama Wapeesittipan, Phatthranit Phattharapornjaroen, Vishnu Nayak Badavath, Asada Leelahavanichkul, Tanittha Chatsuwan. Overcoming addition of phosphoethanolamine to lipid A mediated colistin resistance in Acinetobacter baumannii clinical isolates with colistin-sulbactam combination therapy. Scientific reports. 2022 07; 12(1):11390. doi: 10.1038/s41598-022-15386-1. [PMID: 35794134]
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  • Tomoki Komeda, Shovita Shrestha, Jatan B Sherchan, Mari Tohya, Tomomi Hishinuma, Jeevan B Sherchand, Tatsuya Tada, Teruo Kirikae. Emergence of a highly colistin-resistant Aeromonas jandaei clinical isolate harbouring four genes encoding phosphoethanolamine transferases in Nepal. International journal of antimicrobial agents. 2022 Apr; 59(4):106544. doi: 10.1016/j.ijantimicag.2022.106544. [PMID: 35134503]
  • Corinna Melanie Held, Anic Guebelin, Andreas Krebs, Jörn Oliver Sass, Michael Wurm, Ekkehart Lausch, Natascha van der Werf-Grohmann, Karl Otfried Schwab. Screening for hypophosphatasia: does biochemistry lead the way?. Journal of pediatric endocrinology & metabolism : JPEM. 2022 Feb; 35(2):169-178. doi: 10.1515/jpem-2021-0104. [PMID: 34551461]
  • Wendong Ma, Xukai Jiang, Yujiang Dou, Zhihong Zhang, Jian Li, Bing Yuan, Kai Yang. Biophysical Impact of Lipid A Modification Caused by Mobile Colistin Resistance Gene on Bacterial Outer Membranes. The journal of physical chemistry letters. 2021 Dec; 12(48):11629-11635. doi: 10.1021/acs.jpclett.1c03295. [PMID: 34817187]
  • Martin Tannert, Gerd Ulrich Balcke, Alain Tissier, Margret Köck. At4g29530 is a phosphoethanolamine phosphatase homologous to PECP1 with a role in flowering time regulation. The Plant journal : for cell and molecular biology. 2021 08; 107(4):1072-1083. doi: 10.1111/tpj.15367. [PMID: 34098589]
  • Cory J White, Jessica M Ellis, Michael J Wolfgang. The role of ethanolamine phosphate phospholyase in regulation of astrocyte lipid homeostasis. The Journal of biological chemistry. 2021 07; 297(1):100830. doi: 10.1016/j.jbc.2021.100830. [PMID: 34048714]
  • Eva Kočar, Tea Lenarčič, Vesna Hodnik, Anastasija Panevska, Yunjie Huang, Gregor Bajc, Rok Kostanjšek, Anjaparavanda P Naren, Peter Maček, Gregor Anderluh, Kristina Sepčić, Marjetka Podobnik, Matej Butala. Crystal structure of RahU, an aegerolysin protein from the human pathogen Pseudomonas aeruginosa, and its interaction with membrane ceramide phosphorylethanolamine. Scientific reports. 2021 03; 11(1):6572. doi: 10.1038/s41598-021-85956-2. [PMID: 33753805]
  • Pankaj B Tiwari, Radhakrishnan Mahalakshmi. Interplay of protein primary sequence, lipid membrane, and chaperone in β-barrel assembly. Protein science : a publication of the Protein Society. 2021 03; 30(3):624-637. doi: 10.1002/pro.4022. [PMID: 33410567]
  • Kyong-Oh Shin, Maftuna Shamshiddinova, Jung-No Lee, Kwang-Sik Lee, Yong-Moon Lee. A Bioassay Using a Pentadecanal Derivative to Measure S1P Lyase Activity. International journal of molecular sciences. 2021 Feb; 22(3):. doi: 10.3390/ijms22031438. [PMID: 33535437]
  • Hyemin Min, Esther Youn, Jaehoon Kim, Su Young Son, Choong Hwan Lee, Yhong-Hee Shim. Effects of Phosphoethanolamine Supplementation on Mitochondrial Activity and Lipogenesis in a Caffeine Ingestion Caenorhabditis elegans Model. Nutrients. 2020 Oct; 12(11):. doi: 10.3390/nu12113348. [PMID: 33143181]
  • Xukai Jiang, Kai Yang, Mei-Ling Han, Bing Yuan, Jingliang Li, Bin Gong, Tony Velkov, Falk Schreiber, Lushan Wang, Jian Li. Outer Membranes of Polymyxin-Resistant Acinetobacter baumannii with Phosphoethanolamine-Modified Lipid A and Lipopolysaccharide Loss Display Different Atomic-Scale Interactions with Polymyxins. ACS infectious diseases. 2020 10; 6(10):2698-2708. doi: 10.1021/acsinfecdis.0c00330. [PMID: 32871077]
  • Christopher Aisenbrey, Mariana Amaro, Petr Pospíšil, Martin Hof, Burkhard Bechinger. Highly synergistic antimicrobial activity of magainin 2 and PGLa peptides is rooted in the formation of supramolecular complexes with lipids. Scientific reports. 2020 07; 10(1):11652. doi: 10.1038/s41598-020-68416-1. [PMID: 32669585]
  • Eveline Lefever, Peter Witters, Evelien Gielen, Annick Vanclooster, Wouter Meersseman, Eva Morava, David Cassiman, Michaël R Laurent. Hypophosphatasia in Adults: Clinical Spectrum and Its Association With Genetics and Metabolic Substrates. Journal of clinical densitometry : the official journal of the International Society for Clinical Densitometry. 2020 Jul; 23(3):340-348. doi: 10.1016/j.jocd.2018.12.006. [PMID: 30655187]
  • Soon Goo Lee, Michelle S Chung, Antea J DeMarsilis, Cynthia K Holland, Rohit V Jaswaney, Cherry Jiang, Jakob H P Kroboth, Kevin Kulshrestha, Raymundo Z W Marcelo, Vidhya M Meyyappa, Grant B Nelson, Janki K Patel, Alex J Petronio, Samantha K Powers, Peter R Qin, Mythili Ramachandran, Divya Rayapati, John A Rincon, Andreia Rocha, Joan Gabriel Rodinho Nunes Ferreira, Micah K Steinbrecher, Kaisen Yao, Eric J Zhang, Angela J Zou, Margery Gang, Melanie Sparks, Barrie Cascella, Wilhelm Cruz, Joseph M Jez. Structural and biochemical analysis of phosphoethanolamine methyltransferase from the pine wilt nematode Bursaphelenchus xylophilus. Molecular and biochemical parasitology. 2020 07; 238(?):111291. doi: 10.1016/j.molbiopara.2020.111291. [PMID: 32479776]
  • Emily Lythell, Reynier Suardíaz, Philip Hinchliffe, Chonnikan Hanpaibool, Surawit Visitsatthawong, A Sofia F Oliveira, Eric J M Lang, Panida Surawatanawong, Vannajan Sanghiran Lee, Thanyada Rungrotmongkol, Natalie Fey, James Spencer, Adrian J Mulholland. Resistance to the "last resort" antibiotic colistin: a single-zinc mechanism for phosphointermediate formation in MCR enzymes. Chemical communications (Cambridge, England). 2020 Jun; 56(50):6874-6877. doi: 10.1039/d0cc02520h. [PMID: 32432618]
  • Lin Ding, Ling-Yu Zhang, Hao-Hao Shi, Cheng-Cheng Wang, Xiao-Ming Jiang, Chang-Hu Xue, Teruyoshi Yanagita, Tian-Tian Zhang, Yu-Ming Wang. Eicosapentaenoic Acid-Enriched Phosphoethanolamine Plasmalogens Alleviated Atherosclerosis by Remodeling Gut Microbiota to Regulate Bile Acid Metabolism in LDLR-/- Mice. Journal of agricultural and food chemistry. 2020 May; 68(19):5339-5348. doi: 10.1021/acs.jafc.9b08296. [PMID: 32306729]
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