Glycerylphosphorylcholine (BioDeep_00000179533)
Main id: BioDeep_00000018617
human metabolite PANOMIX_OTCML-2023 blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds natural product
代谢物信息卡片
{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium
化学式: C8H20NO6P (257.102819)
中文名称: 甘油磷酸胆碱, 甘磷酸胆碱
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C[N+](C)(C)CCOP(=O)(O)OC[C@H](O)CO
InChI: InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3
描述信息
Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. [HMDB]
D013501 - Surface-Active Agents > D054709 - Lecithins
sn-Glycero-3-phosphocholine (Choline Alfoscerate) is a precursor in the biosynthesis of brain phospholipids and increases the bioavailability of choline in nervous tissue. sn-Glycero-3-phosphocholine (Choline Alfoscerate) has significant effects on cognitive function with a good safety profile and tolerability, and is effective in the treatment of Alzheimer's disease and dementia[1][2].
同义名列表
19 个代谢物同义名
{2-[(2,3-dihydroxypropyl phosphono)oxy]ethyl}trimethylazanium; L alpha Glycerylphosphorylcholine; L-alpha-Glycerylphosphorylcholine; 3-Phosphocholine, glycerol; Glycerol 3 phosphocholine; Glycerylphosphorylcholine; Glycerol 3-phosphocholine; Glycerophosphate, choline; Glycerophosphorylcholine; CHOLINE GLYCEROPHOSPHATE; Choline alfosceric acid; Alphoscerate, choline; Alfoscerate, choline; Choline alphoscerate; Choline alfoscerate; Alpha-GPC; L-α-GPC; sn-Glycero-3-phosphocholine; sn-Glycero-3-phosphocholine
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:135063
- PubChem: 11234
- HMDB: HMDB0252858
- Wikipedia: Alpha-GPC
- MeSH: Glycerylphosphorylcholine
- foodb: FDB021802
- CAS: 28319-77-9
- CAS: 4217-84-9
- CAS: 563-24-6
- medchemexpress: HY-17552
- LOTUS: LTS0002115
- wikidata: Q60476027
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-359
- KEGG: C00670
- PubChem: 3939
- KNApSAcK: 16870
- LOTUS: LTS0059489
- LOTUS: LTS0260060
- wikidata: Q28529699
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)
10 个相关的物种来源信息
- 3701 - Arabidopsis: LTS0059489
- 3702 - Arabidopsis thaliana: 10.1104/PP.109.148031
- 3702 - Arabidopsis thaliana: LTS0059489
- 3700 - Brassicaceae: LTS0059489
- 2759 - Eukaryota: LTS0059489
- 9606 - Homo sapiens: -
- 3398 - Magnoliopsida: LTS0059489
- 35493 - Streptophyta: LTS0059489
- 58023 - Tracheophyta: LTS0059489
- 33090 - Viridiplantae: LTS0059489
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
- Ryohei Tanaka-Kanegae, Hiroyuki Kimura, Koichiro Hamada. Pharmacokinetics of soy-derived lysophosphatidylcholine compared with that of glycerophosphocholine: a randomized controlled trial.
Bioscience, biotechnology, and biochemistry.
2024 May; 88(6):648-655. doi:
10.1093/bbb/zbae031. [PMID: 38490741] - Mai Yotsumoto, Risa Fujita, Muneyuki Matsuo, Shinobu Nakanishi, Mitsuhiro Denda, Satoshi Nakata. Effects of the Molecular Structure of Malodor Substances and Their Masking on 1,2-Dioleoyl-sn-glycero-3-phosphocholine Molecular Layers.
Langmuir : the ACS journal of surfaces and colloids.
2024 Apr; 40(13):6878-6883. doi:
10.1021/acs.langmuir.3c03796. [PMID: 38501274] - Yuka Sakuma, Nana Kayamori, Julia Tanaka, Kenya Haga, Masayuki Imai, Toshihiro Kawakatsu. Effects of grafted polymers on the lipid membrane fluidity.
Biophysical journal.
2024 Feb; 123(4):489-501. doi:
10.1016/j.bpj.2024.01.014. [PMID: 38243595] - William R King, Justin Singer, Mitchell Warman, Duncan Wilson, Bernard Hube, Ida Lager, Jana Patton-Vogt. The glycerophosphocholine acyltransferase Gpc1 contributes to phosphatidylcholine biosynthesis, long-term viability, and embedded hyphal growth in Candida albicans.
The Journal of biological chemistry.
2024 Jan; 300(1):105543. doi:
10.1016/j.jbc.2023.105543. [PMID: 38072057] - Denis S Baranov, Anna S Kashnik, Anastasiya N Atnyukova, Sergei A Dzuba. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes.
Molecules (Basel, Switzerland).
2023 Aug; 28(16):. doi:
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Clinical nutrition (Edinburgh, Scotland).
2023 Jul; 42(9):1647-1656. doi:
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American journal of physiology. Endocrinology and metabolism.
2023 04; 324(4):E339-E346. doi:
10.1152/ajpendo.00286.2022. [PMID: 36791322] - Kenji Nakayama, Xin Li, Koji Shimizu, Shusuke Akamatsu, Takahiro Inoue, Takashi Kobayashi, Osamu Ogawa, Takayuki Goto. qShot MALDI analysis: A rapid, simple, convenient, and reliable quantitative phospholipidomics approach using MALDI-TOF/MS.
Talanta.
2023 Mar; 254(?):124099. doi:
10.1016/j.talanta.2022.124099. [PMID: 36502612] - Bin Xie, Shumin Yang. Effect of Fluoxetine on the Surface Behavior of the Lipid Monolayers at Different Surface Pressures.
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Bioscience, biotechnology, and biochemistry.
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Analytical and bioanalytical chemistry.
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10.1007/s00216-015-8527-3. [PMID: 25687682] - Eunkyul Oh, Joshua A Jackman, Saziye Yorulmaz, Vladimir P Zhdanov, Haiwon Lee, Nam-Joon Cho. Contribution of temperature to deformation of adsorbed vesicles studied by nanoplasmonic biosensing.
Langmuir : the ACS journal of surfaces and colloids.
2015 Jan; 31(2):771-81. doi:
10.1021/la504267g. [PMID: 25531903] - Penny Miles, Daniel Frankel. Lipid directed assembly of the HIV capsid protein.
Soft matter.
2014 Dec; 10(47):9562-7. doi:
10.1039/c4sm01860e. [PMID: 25354471] - Maria E Kardash, Sergei A Dzuba. Communication: Orientational self-ordering of spin-labeled cholesterol analogs in lipid bilayers in diluted conditions.
The Journal of chemical physics.
2014 Dec; 141(21):211101. doi:
10.1063/1.4902897. [PMID: 25481121] - Ravi P Sahu, Jesus A Ocana, Kathleen A Harrison, Matheus Ferracini, Christopher E Touloukian, Mohammed Al-Hassani, Louis Sun, Mathew Loesch, Robert C Murphy, Sandra K Althouse, Susan M Perkins, Paul J Speicher, Douglas S Tyler, Raymond L Konger, Jeffrey B Travers. Chemotherapeutic agents subvert tumor immunity by generating agonists of platelet-activating factor.
Cancer research.
2014 Dec; 74(23):7069-78. doi:
10.1158/0008-5472.can-14-2043. [PMID: 25304264] - Nicole M Payton, Michael F Wempe, Yemin Xu, Thomas J Anchordoquy. Long-term storage of lyophilized liposomal formulations.
Journal of pharmaceutical sciences.
2014 Dec; 103(12):3869-3878. doi:
10.1002/jps.24171. [PMID: 25308534] - Krystal L Sly, John C Conboy. Determination of multivalent protein-ligand binding kinetics by second-harmonic correlation spectroscopy.
Analytical chemistry.
2014 Nov; 86(22):11045-54. doi:
10.1021/ac500094v. [PMID: 25314127] - Beth A Surlow, Benjamin M Cooley, Patrick G Needham, Jeffrey L Brodsky, Jana Patton-Vogt. Loss of Ypk1, the yeast homolog to the human serum- and glucocorticoid-induced protein kinase, accelerates phospholipase B1-mediated phosphatidylcholine deacylation.
The Journal of biological chemistry.
2014 Nov; 289(45):31591-604. doi:
10.1074/jbc.m114.581157. [PMID: 25258318] - Michael Lever, Christopher J McEntyre, Peter M George, Sandy Slow, Jane L Elmslie, Helen Lunt, Stephen T Chambers, Amber Parry-Strong, Jeremy D Krebs. Extreme urinary betaine losses in type 2 diabetes combined with bezafibrate treatment are associated with losses of dimethylglycine and choline but not with increased losses of other osmolytes.
Cardiovascular drugs and therapy.
2014 Oct; 28(5):459-68. doi:
10.1007/s10557-014-6542-9. [PMID: 25060556] - Mafumi Hishida, Yasuhisa Yamamura, Kazuya Saito. Salt effects on lamellar repeat distance depending on head groups of neutrally charged lipids.
Langmuir : the ACS journal of surfaces and colloids.
2014 Sep; 30(35):10583-9. doi:
10.1021/la502576x. [PMID: 25126900] - Hanna M G Barriga, Paula Booth, Stuart Haylock, Richard Bazin, Richard H Templer, Oscar Ces. Droplet interface bilayer reconstitution and activity measurement of the mechanosensitive channel of large conductance from Escherichia coli.
Journal of the Royal Society, Interface.
2014 Sep; 11(98):20140404. doi:
10.1098/rsif.2014.0404. [PMID: 25008079] - Urszula M Migas, Lorna Abbey, Trinidad Velasco-Torrijos, Jennifer J McManus. Adding glycolipid functionality to model membranes--phase behaviour of a synthetic glycolipid in a phospholipid membrane.
Soft matter.
2014 Jun; 10(22):3978-83. doi:
10.1039/c4sm00147h. [PMID: 24733306] - Petra Hartmann, Ngwi Fet, Dénes Garab, Andrea Szabó, József Kaszaki, Pramod Kadaba Srinivasan, René H Tolba, Mihály Boros. L-α-glycerylphosphorylcholine reduces the microcirculatory dysfunction and nicotinamide adenine dinucleotide phosphate-oxidase type 4 induction after partial hepatic ischemia in rats.
The Journal of surgical research.
2014 Jun; 189(1):32-40. doi:
10.1016/j.jss.2013.12.025. [PMID: 24636100] - Artur Matysik, Rachel S Kraut. TrackArt: the user friendly interface for single molecule tracking data analysis and simulation applied to complex diffusion in mica supported lipid bilayers.
BMC research notes.
2014 May; 7(?):274. doi:
10.1186/1756-0500-7-274. [PMID: 24885944] - Roman Moser, Meriyem Aktas, Franz Narberhaus. Phosphatidylcholine biosynthesis in Xanthomonas campestris via a yeast-like acylation pathway.
Molecular microbiology.
2014 Feb; 91(4):736-50. doi:
10.1111/mmi.12492. [PMID: 24329598] - Manickavel Vinoth Raj, Kandaswamy Selvakumar, Gunasekaran Krishnamoorthy, Soundarrajan Revathy, Perumal Elumalai, Jagadeesan Arunakaran. Impact of lycopene on epididymal androgen and estrogen receptors' expression in polychlorinated biphenyls-exposed rat.
Reproductive sciences (Thousand Oaks, Calif.).
2014 Jan; 21(1):89-101. doi:
10.1177/1933719113492213. [PMID: 23749762] - Tünde Tőkés, Gabriella Varga, Dénes Garab, Zoltán Nagy, Gábor Fekete, Eszter Tuboly, Imola Plangár, Imola Mán, Rita Emília Szabó, Zoltán Szabó, Gábor Volford, Miklós Ghyczy, József Kaszaki, Mihály Boros, Katalin Hideghéty. Peripheral inflammatory activation after hippocampus irradiation in the rat.
International journal of radiation biology.
2014 Jan; 90(1):1-6. doi:
10.3109/09553002.2013.836617. [PMID: 23968122] - B Brüning, R Stehle, P Falus, B Farago. Influence of charge density on bilayer bending rigidity in lipid vesicles: a combined dynamic light scattering and neutron spin-echo study.
The European physical journal. E, Soft matter.
2013 Jul; 36(7):77. doi:
10.1140/epje/i2013-13077-0. [PMID: 23884623] - Supachai Topanurak, Joan D Ferraris, Jinxi Li, Yuichiro Izumi, Chester K Williams, Marjan Gucek, Guanghui Wang, Xiaoming Zhou, Maurice B Burg. High NaCl- and urea-induced posttranslational modifications that increase glycerophosphocholine by inhibiting GDPD5 phosphodiesterase.
Proceedings of the National Academy of Sciences of the United States of America.
2013 Apr; 110(18):7482-7. doi:
10.1073/pnas.1305220110. [PMID: 23589856] - Keishi Suga, Hiroshi Umakoshi. Detection of nanosized ordered domains in DOPC/DPPC and DOPC/Ch binary lipid mixture systems of large unilamellar vesicles using a TEMPO quenching method.
Langmuir : the ACS journal of surfaces and colloids.
2013 Apr; 29(15):4830-8. doi:
10.1021/la304768f. [PMID: 23506052] - Ravi P Sahu, Irina Petrache, Mary J Van Demark, Badri M Rashid, Jesus A Ocana, Yuxuan Tang, Qiaofang Yi, Matthew J Turner, Raymond L Konger, Jeffrey B Travers. Cigarette smoke exposure inhibits contact hypersensitivity via the generation of platelet-activating factor agonists.
Journal of immunology (Baltimore, Md. : 1950).
2013 Mar; 190(5):2447-54. doi:
10.4049/jimmunol.1202699. [PMID: 23355733] - Seyed Khosrow Tayebati, Daniele Tomassoni, Innocent Ejike Nwankwo, Antonio Di Stefano, Piera Sozio, Laura Serafina Cerasa, Francesco Amenta. Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain.
CNS & neurological disorders drug targets.
2013 Feb; 12(1):94-103. doi:
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PloS one.
2013; 8(7):e68717. doi:
10.1371/journal.pone.0068717. [PMID: 23894336] - Takashi Kawamura, Takeshi Okubo, Koji Sato, Satoshi Fujita, Kazushige Goto, Takafumi Hamaoka, Motoyuki Iemitsu. Glycerophosphocholine enhances growth hormone secretion and fat oxidation in young adults.
Nutrition (Burbank, Los Angeles County, Calif.).
2012 Nov; 28(11-12):1122-6. doi:
10.1016/j.nut.2012.02.011. [PMID: 22673596] - Leandro De Oliveira, Niels Olsen S Câmara, Tatiana Bonetti, Edson G Lo Turco, Ricardo P Bertolla, Antonio F Moron, Nelson Sass, Ismael Dale Cotrim Guerreiro Da Silva. Lipid fingerprinting in women with early-onset preeclampsia: a first look.
Clinical biochemistry.
2012 Jul; 45(10-11):852-5. doi:
10.1016/j.clinbiochem.2012.04.012. [PMID: 22548912] - Paul D Rainville, Jennifer L Simeone, Sean M McCarthy, Norman W Smith, David Cowan, Robert S Plumb. Investigation of microbore UPLC and nontraditional mobile phase compositions for bioanalytical LC-MS/MS.
Bioanalysis.
2012 Jun; 4(11):1287-97. doi:
10.4155/bio.12.78. [PMID: 22720648] - Steve Silvester, Luke Smith. Profiling phospholipid elution in reversed-phase LC-MS/MS bioanalytical methods in order to avoid matrix effects.
Bioanalysis.
2012 May; 4(8):879-95. doi:
10.4155/bio.12.33. [PMID: 22533563] - Chinmoy Ghosh, Chandrakant P Shinde, Bhaswat S Chakraborty. Influence of ionization source design on matrix effects during LC-ESI-MS/MS analysis.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2012 Apr; 893-894(?):193-200. doi:
10.1016/j.jchromb.2012.03.012. [PMID: 22464433] - Anisha Wijeyesekera, Colin Selman, Richard H Barton, Elaine Holmes, Jeremy K Nicholson, Dominic J Withers. Metabotyping of long-lived mice using 1H NMR spectroscopy.
Journal of proteome research.
2012 Apr; 11(4):2224-35. doi:
10.1021/pr2010154. [PMID: 22225495] - Nicholas P Gray, Stuart A McDougall, John R Dean. Analytical bias between species caused by matrix effects in quantitative analysis of a small-molecule pharmaceutical candidate in plasma.
Bioanalysis.
2012 Mar; 4(6):675-84. doi:
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Analytical chemistry.
2011 Sep; 83(17):6689-97. doi:
10.1021/ac2012224. [PMID: 21766834] - Hugo A L Filipe, Maria João Moreno, Luís M S Loura. Interaction of 7-nitrobenz-2-oxa-1,3-diazol-4-yl-labeled fatty amines with 1-palmitoyl, 2-oleoyl-sn-glycero-3-phosphocholine bilayers: a molecular dynamics study.
The journal of physical chemistry. B.
2011 Aug; 115(33):10109-19. doi:
10.1021/jp203532c. [PMID: 21749140] - Amy M Brownawell, Edward L Carmines, Federica Montesano. Safety assessment of AGPC as a food ingredient.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Jun; 49(6):1303-15. doi:
10.1016/j.fct.2011.03.012. [PMID: 21414376] - Lijun Zhang, Xiaofang Jia, Xia Peng, Qiang Ou, Zhengguo Zhang, Chao Qiu, Yamin Yao, Fang Shen, Hua Yang, Fang Ma, Jiefei Wang, Zhenghong Yuan. Development and validation of a liquid chromatography-mass spectrometry metabonomic platform in human plasma of liver failure caused by hepatitis B virus.
Acta biochimica et biophysica Sinica.
2010 Oct; 42(10):688-98. doi:
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PloS one.
2010 Sep; 5(9):e12590. doi:
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Oncotarget.
2010 Jul; 1(3):185-97. doi:
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The Analyst.
2010 Apr; 135(4):751-8. doi:
10.1039/b922854c. [PMID: 20349540] - Morgan Gallazzini, Maurice B Burg. What's new about osmotic regulation of glycerophosphocholine.
Physiology (Bethesda, Md.).
2009 Aug; 24(?):245-9. doi:
10.1152/physiol.00009.2009. [PMID: 19675355] - Xi Zhang, Shelagh M Ferguson-Miller, Gavin E Reid. Characterization of ornithine and glutamine lipids extracted from cell membranes of Rhodobacter sphaeroides.
Journal of the American Society for Mass Spectrometry.
2009 Feb; 20(2):198-212. doi:
10.1016/j.jasms.2008.08.017. [PMID: 18835523] - Omnia A Ismaiel, Matthew S Halquist, Magda Y Elmamly, Abdalla Shalaby, H Thomas Karnes. Monitoring phospholipids for assessment of ion enhancement and ion suppression in ESI and APCI LC/MS/MS for chlorpheniramine in human plasma and the importance of multiple source matrix effect evaluations.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Nov; 875(2):333-43. doi:
10.1016/j.jchromb.2008.08.032. [PMID: 18926779] - Lihong Du, Robert L White. Reducing glycerophosphocholine lipid matrix interference effects in biological fluid assays by using high-turbulence liquid chromatography.
Rapid communications in mass spectrometry : RCM.
2008 Nov; 22(21):3362-70. doi:
10.1002/rcm.3747. [PMID: 18837005] - Wei-Yuan Hou, Ding-Xin Long, Hui-Ping Wang, Qi Wang, Yi-Jun Wu. The homeostasis of phosphatidylcholine and lysophosphatidylcholine was not disrupted during tri-o-cresyl phosphate-induced delayed neurotoxicity in hens.
Toxicology.
2008 Oct; 252(1-3):56-63. doi:
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