Glycerophosphoric acid (BioDeep_00000014871)

 

Secondary id: BioDeep_00000405205

human metabolite blood metabolite


代谢物信息卡片


alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled

化学式: C3H9O6P (172.01367439999999)
中文名称: 甘油磷酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.38%

分子结构信息

SMILES: C(C(COP(=O)(O)O)O)O
InChI: InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)

描述信息

Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in brain and skeletal muscle cells of mammals (wikipedia). [HMDB]

同义名列表

67 个代谢物同义名

alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled; alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled; alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer; alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer; alpha-Glycerophosphoric acid, disodium salt (+-)-isomer; 1,2,3-Propanetriol, 1-(dihydrogen phosphoric acid); alpha-Glycerophosphoric acid, monomagnesium salt; alpha-Glycerophosphoric acid, fe(+3) salt (3:2); 2,3-Hydroxy-1-propyl dihydrogen phosphoric acid; 2,3-Dihydroxypropyl dihydrogen phosphoric acid; alpha-Glycerophosphoric acid, monocalcium salt; 1,2,3-Propanetriol, 1-(dihydrogen phosphate); alpha-Glycerophosphoric acid, disodium salt; alpha-Glycerophosphoric acid, calcium salt; alpha-Glycerophosphoric acid, sodium salt; 2,3-Hydroxy-1-propyl dihydrogen phosphate; alpha-Glycerophosphoric acid, (DL)-isomer; alpha-Glycerophosphoric acid, (R)-isomer; alpha-Glycerophosphoric acid, (S)-isomer; 2,3-Dihydroxypropyl dihydrogen phosphate; alpha-Glycerophosphoric acid, fe salt; (2,3-dihydroxypropoxy)phosphonic acid; D,L-alpha-Glycerol-phosphoric acid; Glycerol alpha-phosphoric acid; D,L-a-Glycerol-phosphoric acid; D,L-Α-glycerol-phosphoric acid; Glycerol 1-monophosphoric acid; rac-Glycerol 1-phosphoric acid; DL-Glycerol 1-phosphoric acid; DL-Glyceryl 1-phosphoric acid; DL-Glycerol 3-phosphoric acid; D,L-alpha-Glycerol-phosphate; alpha-Glycerophosphoric acid; Glycerol α-phosphoric acid; Glycerol 1-phosphoric acid; Glycerol a-phosphoric acid; Glycerol-3-phosphoric acid; Disodium glycerophosphate; Glycerol alpha-phosphate; Α-glycerophosphoric acid; 3-Glycerophosphoric acid; D,L-Α-glycerol-phosphate; Glycerol 1-monophosphate; D,L-a-Glycerol-phosphate; rac-Glycerol 1-phosphate; a-Glycerophosphoric acid; 1-Glycerophosphoric acid; DL-Glycerol 1-phosphate; DL-Glyceryl 1-phosphate; Sodium glycerophosphate; DL-Glycerol 3-phosphate; alpha-Glycerophosphate; Glycerophosphoric acid; alpha-Phosphoglycerol; Glycerol a-phosphate; Glycerol α-phosphate; Glycerol 3-phosphate; Glycerol-3-phosphate; Glycerol 1-phosphate; 1-Glycerophosphate; a-Glycerophosphate; Α-glycerophosphate; 3-Glycerophosphate; 1-Phosphoglycerol; a-Phosphoglycerol; Α-phosphoglycerol; PG



数据库引用编号

15 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)

19 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

  • Pilar Garcia-Jimenez, Diana Del Rosario-Santana, Rafael R Robaina. Jasmonates and Ethylene Shape Floridoside Synthesis during Carposporogenesis in the Red Seaweed Grateloupia imbricata. Marine drugs. 2024 Feb; 22(3):. doi: 10.3390/md22030115. [PMID: 38535456]
  • 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]
  • Shiva Kumar Angala, Ana Carreras-Gonzalez, Emilie Huc-Claustre, Itxaso Anso, Devinder Kaur, Victoria Jones, Zuzana Palčeková, Juan M Belardinelli, Célia de Sousa-d'Auria, Libin Shi, Nawel Slama, Christine Houssin, Annaïk Quémard, Michael McNeil, Marcelo E Guerin, Mary Jackson. Acylation of glycerolipids in mycobacteria. Nature communications. 2023 10; 14(1):6694. doi: 10.1038/s41467-023-42478-x. [PMID: 37872138]
  • Y Chen, H B Shi, W L Le, Q N Tang. [Effect of calcium-independent phospholipase A2 on the expression of glycerol 3-phosphate dehydrogenase in human non-alcoholic fatty liver disease cells]. Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology. 2023 Oct; 31(10):1063-1067. doi: 10.3760/cma.j.cn501113-20220724-00394. [PMID: 38016771]
  • Superior Syngkli, Bidyadhar Das. Purification and characterization of human glycerol 3-phosphate dehydrogenases (mitochondrial and cytosolic) by NAD+/NADH redox method. Biochimie. 2023 Jul; ?(?):. doi: 10.1016/j.biochi.2023.07.015. [PMID: 37481063]
  • Urszula Łapińska, Georgina Glover, Zehra Kahveci, Nicholas A T Irwin, David S Milner, Maxime Tourte, Sonja-Verena Albers, Alyson E Santoro, Thomas A Richards, Stefano Pagliara. Systematic comparison of unilamellar vesicles reveals that archaeal core lipid membranes are more permeable than bacterial membranes. PLoS biology. 2023 04; 21(4):e3002048. doi: 10.1371/journal.pbio.3002048. [PMID: 37014915]
  • Jianzhi Zhang, Tuo Li, Zhilai Hong, Chenfei Ma, Xiaoting Fang, Fengfeng Zheng, Wenkai Teng, Chuanlun Zhang, Tong Si. Biosynthesis of Hybrid Neutral Lipids with Archaeal and Eukaryotic Characteristics in Engineered Saccharomyces cerevisiae. Angewandte Chemie (International ed. in English). 2023 01; 62(4):e202214344. doi: 10.1002/anie.202214344. [PMID: 36424352]
  • Diana X Sahonero-Canavesi, Melvin F Siliakus, Alejandro Abdala Asbun, Michel Koenen, F A Bastiaan von Meijenfeldt, Sjef Boeren, Nicole J Bale, Julia C Engelman, Kerstin Fiege, Lora Strack van Schijndel, Jaap S Sinninghe Damsté, Laura Villanueva. Disentangling the lipid divide: Identification of key enzymes for the biosynthesis of membrane-spanning and ether lipids in Bacteria. Science advances. 2022 12; 8(50):eabq8652. doi: 10.1126/sciadv.abq8652. [PMID: 36525503]
  • Anfal Al-Mass, Pegah Poursharifi, Marie-Line Peyot, Roxane Lussier, Isabelle Chenier, Yat Hei Leung, Anindya Ghosh, Abel Oppong, Elite Possik, Yves Mugabo, Rasheed Ahmad, Robert Sladek, S R Murthy Madiraju, Fahd Al-Mulla, Marc Prentki. Hepatic glycerol shunt and glycerol-3-phosphate phosphatase control liver metabolism and glucodetoxification under hyperglycemia. Molecular metabolism. 2022 12; 66(?):101609. doi: 10.1016/j.molmet.2022.101609. [PMID: 36198384]
  • Aardra Kachroo, Huazhen Liu, Xinyu Yuan, Tatsushi Kurokawa, Pradeep Kachroo. Systemic acquired resistance-associated transport and metabolic regulation of salicylic acid and glycerol-3-phosphate. Essays in biochemistry. 2022 09; 66(5):673-681. doi: 10.1042/ebc20210098. [PMID: 35920211]
  • Buse Ozer Bekmez, Serife Suna Oguz. Early vs late initiation of sodium glycerophosphate: Impact on hypophosphatemia in preterm infants <32 weeks. Clinical nutrition (Edinburgh, Scotland). 2022 02; 41(2):415-423. doi: 10.1016/j.clnu.2021.12.011. [PMID: 35007810]
  • Elite Possik, Clémence Schmitt, Anfal Al-Mass, Ying Bai, Laurence Côté, Johanne Morin, Heidi Erb, Abel Oppong, Wahab Kahloan, J Alex Parker, S R Murthy Madiraju, Marc Prentki. Phosphoglycolate phosphatase homologs act as glycerol-3-phosphate phosphatase to control stress and healthspan in C. elegans. Nature communications. 2022 01; 13(1):177. doi: 10.1038/s41467-021-27803-6. [PMID: 35017476]
  • Yin Zhang, Naiwang Tang, Jinjie Zhou. Intermedin1‑47 inhibits high phosphate‑induced vascular smooth muscle cell calcification by regulating Wnt/β‑catenin signaling. Molecular medicine reports. 2021 Oct; 24(4):. doi: 10.3892/mmr.2021.12373. [PMID: 34414455]
  • YuJin Noh, Hwanhui Lee, Myeongsun Kim, Seong-Joo Hong, Hookeun Lee, Dong-Myung Kim, Byung-Kwan Cho, Choul-Gyun Lee, Hyung-Kyoon Choi. Enhanced Production of Photosynthetic Pigments and Various Metabolites and Lipids in the Cyanobacteria Synechocystis sp. PCC 7338 Culture in the Presence of Exogenous Glucose. Biomolecules. 2021 02; 11(2):. doi: 10.3390/biom11020214. [PMID: 33546462]
  • James R Krycer, Lake-Ee Quek, Deanne Francis, Armella Zadoorian, Fiona C Weiss, Kristen C Cooke, Marin E Nelson, Alexis Diaz-Vegas, Sean J Humphrey, Richard Scalzo, Akiyoshi Hirayama, Satsuki Ikeda, Futaba Shoji, Kumi Suzuki, Kevin Huynh, Corey Giles, Bianca Varney, Shilpa R Nagarajan, Andrew J Hoy, Tomoyoshi Soga, Peter J Meikle, Gregory J Cooney, Daniel J Fazakerley, David E James. Insulin signaling requires glucose to promote lipid anabolism in adipocytes. The Journal of biological chemistry. 2020 09; 295(38):13250-13266. doi: 10.1074/jbc.ra120.014907. [PMID: 32723868]
  • Gábor Tasnádi, Marcin Staśko, Klaus Ditrich, Mélanie Hall, Kurt Faber. Preparative-Scale Enzymatic Synthesis of rac-Glycerol-1-phosphate from Crude Glycerol Using Acid Phosphatases and Phosphate. ChemSusChem. 2020 Apr; 13(7):1759-1763. doi: 10.1002/cssc.201903236. [PMID: 31944595]
  • Petra Simic, Wondong Kim, Wen Zhou, Kerry A Pierce, Wenhan Chang, David B Sykes, Najihah B Aziz, Sammy Elmariah, Debby Ngo, Paola Divieti Pajevic, Nicolas Govea, Bryan R Kestenbaum, Ian H de Boer, Zhiqiang Cheng, Marta Christov, Jerold Chun, David E Leaf, Sushrut S Waikar, Andrew M Tager, Robert E Gerszten, Ravi I Thadhani, Clary B Clish, Harald Jüppner, Marc N Wein, Eugene P Rhee. Glycerol-3-phosphate is an FGF23 regulator derived from the injured kidney. The Journal of clinical investigation. 2020 03; 130(3):1513-1526. doi: 10.1172/jci131190. [PMID: 32065590]
  • Jonghwa Lee, Neale D Ridgway. Substrate channeling in the glycerol-3-phosphate pathway regulates the synthesis, storage and secretion of glycerolipids. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2020 01; 1865(1):158438. doi: 10.1016/j.bbalip.2019.03.010. [PMID: 30959116]
  • Soshi Takahashi, Jun Saegusa, Akira Onishi, Akio Morinobu. Biomarkers identified by serum metabolomic analysis to predict biologic treatment response in rheumatoid arthritis patients. Rheumatology (Oxford, England). 2019 12; 58(12):2153-2161. doi: 10.1093/rheumatology/kez199. [PMID: 31143951]
  • M B Shine, Qing-Ming Gao, R V Chowda-Reddy, Asheesh K Singh, Pradeep Kachroo, Aardra Kachroo. Glycerol-3-phosphate mediates rhizobia-induced systemic signaling in soybean. Nature communications. 2019 11; 10(1):5303. doi: 10.1038/s41467-019-13318-8. [PMID: 31757957]
  • Naoki Nemoto, Ken Ichi Miyazono, Masaru Tanokura, Akihiko Yamagishi. Crystal structure of (S)-3-O-geranylgeranylglyceryl phosphate synthase from Thermoplasma acidophilum in complex with the substrate sn-glycerol 1-phosphate. Acta crystallographica. Section F, Structural biology communications. 2019 Jul; 75(Pt 7):470-479. doi: 10.1107/s2053230x19007453. [PMID: 31282866]
  • Ling Zhang, Fen Chen, Jiatong Zheng, Hongwei Wang, Xingjun Qin, Weisan Pan. Chitosan-based liposomal thermogels for the controlled delivery of pingyangmycin: design, optimization and in vitro and in vivo studies. Drug delivery. 2018 Nov; 25(1):690-702. doi: 10.1080/10717544.2018.1444684. [PMID: 29484910]
  • Rana Sagnak, Sandrine Cochot, Carole Molina-Jouve, Jean-Marc Nicaud, Stéphane E Guillouet. Modulation of the Glycerol Phosphate availability led to concomitant reduction in the citric acid excretion and increase in lipid content and yield in Yarrowia lipolytica. Journal of biotechnology. 2018 Jan; 265(?):40-45. doi: 10.1016/j.jbiotec.2017.11.001. [PMID: 29102548]
  • Elite Possik, S R Murthy Madiraju, Marc Prentki. Glycerol-3-phosphate phosphatase/PGP: Role in intermediary metabolism and target for cardiometabolic diseases. Biochimie. 2017 Dec; 143(?):18-28. doi: 10.1016/j.biochi.2017.08.001. [PMID: 28826615]
  • Luís Crisóstomo, Marco G Alves, Giuseppe Calamita, Mário Sousa, Pedro F Oliveira. Glycerol and testicular activity: the good, the bad and the ugly. Molecular human reproduction. 2017 11; 23(11):725-737. doi: 10.1093/molehr/gax049. [PMID: 28961924]
  • Steven M Dragos, Karl F Bergeron, Frédérik Desmarais, Katherine Suitor, David C Wright, Catherine Mounier, David M Mutch. Reduced SCD1 activity alters markers of fatty acid reesterification, glyceroneogenesis, and lipolysis in murine white adipose tissue and 3T3-L1 adipocytes. American journal of physiology. Cell physiology. 2017 Sep; 313(3):C295-C304. doi: 10.1152/ajpcell.00097.2017. [PMID: 28659287]
  • Jian Ji, Pei Zhu, Fangchao Cui, Fuwei Pi, Yinzhi Zhang, Xiulan Sun. The disorder metabolic profiling in kidney and spleen of mice induced by mycotoxins deoxynivalenol through gas chromatography mass spectrometry. Chemosphere. 2017 Aug; 180(?):267-274. doi: 10.1016/j.chemosphere.2017.03.129. [PMID: 28411543]
  • Judith-Irina Pagel, Nikolai Hulde, Tobias Kammerer, Michaela Schwarz, Daniel Chappell, Alexander Burges, Klaus Hofmann-Kiefer, Markus Rehm. The impact of phosphate-balanced crystalloid infusion on acid-base homeostasis (PALANCE study): study protocol for a randomized controlled trial. Trials. 2017 07; 18(1):313. doi: 10.1186/s13063-017-2051-z. [PMID: 28693594]
  • Ali Mazouri, Nastaran Khosravi, Arash Bordbar, Nasrin Khalesi, Maryam Saboute, Pegah Taherifard, Marjan Mirzababaee, Mehran Ebrahimi. Does Adding Intravenous Phosphorus to Parenteral Nutrition Has Any Effects on Calcium and Phosphorus Metabolism and Bone Mineral Content in Preterm Neonates?. Acta medica Iranica. 2017 Jun; 55(6):395-398. doi: NULL. [PMID: 28843241]
  • Yves Mugabo, Shangang Zhao, Julien Lamontagne, Anfal Al-Mass, Marie-Line Peyot, Barbara E Corkey, Erik Joly, S R Murthy Madiraju, Marc Prentki. Metabolic fate of glucose and candidate signaling and excess-fuel detoxification pathways in pancreatic β-cells. The Journal of biological chemistry. 2017 05; 292(18):7407-7422. doi: 10.1074/jbc.m116.763060. [PMID: 28280244]
  • Archana Singh, Gah-Hyun Lim, Pradeep Kachroo. Transport of chemical signals in systemic acquired resistance. Journal of integrative plant biology. 2017 May; 59(5):336-344. doi: 10.1111/jipb.12537. [PMID: 28304135]
  • Laura Villanueva, Stefan Schouten, Jaap S Sinninghe Damsté. Phylogenomic analysis of lipid biosynthetic genes of Archaea shed light on the 'lipid divide'. Environmental microbiology. 2017 01; 19(1):54-69. doi: 10.1111/1462-2920.13361. [PMID: 27112361]
  • Guanghao Wu, Yuan Yuan, Jintian He, Ying Li, Xiaojing Dai, Baohua Zhao. Stable thermosensitive in situ gel-forming systems based on the lyophilizate of chitosan/α,β-glycerophosphate salts. International journal of pharmaceutics. 2016 Sep; 511(1):560-569. doi: 10.1016/j.ijpharm.2016.07.050. [PMID: 27457422]
  • Gah-Hyun Lim, Aardra Kachroo, Pradeep Kachroo. Role of plasmodesmata and plasmodesmata localizing proteins in systemic immunity. Plant signaling & behavior. 2016 09; 11(9):e1219829. doi: 10.1080/15592324.2016.1219829. [PMID: 27645210]
  • Virginia L Gaveglio, Ana C Pascual, Norma M Giusto, Susana J Pasquaré. Age-related changes in retinoic, docosahexaenoic and arachidonic acid modulation in nuclear lipid metabolism. Archives of biochemistry and biophysics. 2016 08; 604(?):121-7. doi: 10.1016/j.abb.2016.06.017. [PMID: 27355428]
  • Jiancai Wang, Ronghua Xu, Ruling Wang, Mohammad Enamul Haque, Aizhong Liu. Overexpression of ACC gene from oleaginous yeast Lipomyces starkeyi enhanced the lipid accumulation in Saccharomyces cerevisiae with increased levels of glycerol 3-phosphate substrates. Bioscience, biotechnology, and biochemistry. 2016 Jun; 80(6):1214-22. doi: 10.1080/09168451.2015.1136883. [PMID: 26865376]
  • Gah-Hyun Lim, M B Shine, Laura de Lorenzo, Keshun Yu, Weier Cui, Duroy Navarre, Arthur G Hunt, Jung-Youn Lee, Aardra Kachroo, Pradeep Kachroo. Plasmodesmata Localizing Proteins Regulate Transport and Signaling during Systemic Acquired Immunity in Plants. Cell host & microbe. 2016 Apr; 19(4):541-9. doi: 10.1016/j.chom.2016.03.006. [PMID: 27078071]
  • Vijayata Singh, Praveen Kumar Singh, Adnan Siddiqui, Subaran Singh, Zeeshan Zahoor Banday, Ashis Kumar Nandi. Over-expression of Arabidopsis thaliana SFD1/GLY1, the gene encoding plastid localized glycerol-3-phosphate dehydrogenase, increases plastidic lipid content in transgenic rice plants. Journal of plant research. 2016 Mar; 129(2):285-293. doi: 10.1007/s10265-015-0781-0. [PMID: 26747130]
  • Hannah K Wayment-Steele, Yujia Jing, Marcus J Swann, Lewis E Johnson, Björn Agnarsson, Sofia Svedhem, Malkiat S Johal, Angelika Kunze. Effects of Al(3+) on Phosphocholine and Phosphoglycerol Containing Solid Supported Lipid Bilayers. Langmuir : the ACS journal of surfaces and colloids. 2016 Feb; 32(7):1771-81. doi: 10.1021/acs.langmuir.5b03999. [PMID: 26783873]
  • Sayaka Kato, Yoko Nakajima, Risa Awaya, Ikue Hata, Yosuke Shigematsu, Shinji Saitoh, Tetsuya Ito. Pitfall in the Diagnosis of Fructose-1,6-Bisphosphatase Deficiency: Difficulty in Detecting Glycerol-3-Phosphate with Solvent Extraction in Urinary GC/MS Analysis. The Tohoku journal of experimental medicine. 2015 11; 237(3):235-9. doi: 10.1620/tjem.237.235. [PMID: 26549536]
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