lysophosphatidylinositol (BioDeep_00000180607)
human metabolite blood metabolite
代谢物信息卡片
[2-Hydroxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropyl] acetate
化学式: C11H21O12P (376.07705960000004)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 50%
分子结构信息
SMILES: CC(=O)OCC(COP(=O)(O)OC1C(C(C(C(C1O)O)O)O)O)O
InChI: InChI=1S/C11H21O12P/c1-4(12)21-2-5(13)3-22-24(19,20)23-11-9(17)7(15)6(14)8(16)10(11)18/h5-11,13-18H,2-3H2,1H3,(H,19,20)
描述信息
同义名列表
数据库引用编号
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)
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。
文献列表
- Makoto Kurano, Tamaki Kobayashi, Eri Sakai, Kazuhisa Tsukamoto, Yutaka Yatomi. Lysophosphatidylinositol, especially albumin-bound form, induces inflammatory cytokines in macrophages.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2021 06; 35(6):e21673. doi:
10.1096/fj.202100245r. [PMID: 34042213] - Toshihiko Tsutsumi, Risa Matsuda, Katsuya Morito, Kohei Kawabata, Miho Yokota, Miki Nikawadori, Manami Inoue-Fujiwara, Satoshi Kawashima, Mayumi Hidaka, Takenori Yamamoto, Naoshi Yamazaki, Tamotsu Tanaka, Yasuo Shinohara, Hiroyuki Nishi, Akira Tokumura. Identification of human glycerophosphodiesterase 3 as an ecto phospholipase C that converts the G protein-coupled receptor 55 agonist lysophosphatidylinositol to bioactive monoacylglycerols in cultured mammalian cells.
Biochimica et biophysica acta. Molecular and cell biology of lipids.
2020 09; 1865(9):158761. doi:
10.1016/j.bbalip.2020.158761. [PMID: 32629025] - Lin Yang, Liang Wang, Yangyang Deng, Lizhe Sun, Bowen Lou, Zuyi Yuan, Yue Wu, Bo Zhou, Junhui Liu, Jianqing She. Serum lipids profiling perturbances in patients with ischemic heart disease and ischemic cardiomyopathy.
Lipids in health and disease.
2020 May; 19(1):89. doi:
10.1186/s12944-020-01269-9. [PMID: 32386519] - Xiao-Lei Zhou, Xin Guo, Yu-Pin Song, Chong-Yue Zhu, Wei Zou. The LPI/GPR55 axis enhances human breast cancer cell migration via HBXIP and p-MLC signaling.
Acta pharmacologica Sinica.
2018 Mar; 39(3):459-471. doi:
10.1038/aps.2017.157. [PMID: 29188802] - Jeffrey M Collins, Douglas I Walker, Dean P Jones, Nestani Tukvadze, Ken H Liu, ViLinh T Tran, Karan Uppal, Jennifer K Frediani, Kirk A Easley, Neeta Shenvi, Manoj Khadka, Eric A Ortlund, Russell R Kempker, Henry M Blumberg, Thomas R Ziegler. High-resolution plasma metabolomics analysis to detect Mycobacterium tuberculosis-associated metabolites that distinguish active pulmonary tuberculosis in humans.
PloS one.
2018; 13(10):e0205398. doi:
10.1371/journal.pone.0205398. [PMID: 30308073] - Junhwan Kim, Tai Yin, Koichiro Shinozaki, Joshua W Lampe, Lance B Becker. Potential of lysophosphatidylinositol as a prognostic indicator of cardiac arrest using a rat model.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2017 Dec; 22(8):755-763. doi:
10.1080/1354750x.2016.1265002. [PMID: 27879158] - Kazuki Harada, Tetsuya Kitaguchi, Taichi Kamiya, Kyaw Htet Aung, Kazuaki Nakamura, Kunihiro Ohta, Takashi Tsuboi. Lysophosphatidylinositol-induced activation of the cation channel TRPV2 triggers glucagon-like peptide-1 secretion in enteroendocrine L cells.
The Journal of biological chemistry.
2017 06; 292(26):10855-10864. doi:
10.1074/jbc.m117.788653. [PMID: 28533434] - Nina Eikelis, Elisabeth A Lambert, Sarah Phillips, Carolina Ika Sari, Piyushkumar A Mundra, Jacquelyn M Weir, Kevin Huynh, Mariee T Grima, Nora E Straznicky, John B Dixon, Markus P Schlaich, Peter J Meikle, Gavin W Lambert. Muscle Sympathetic Nerve Activity Is Associated With Elements of the Plasma Lipidomic Profile in Young Asian Adults.
The Journal of clinical endocrinology and metabolism.
2017 06; 102(6):2059-2068. doi:
10.1210/jc.2016-3738. [PMID: 28323975] - Ieva Ailte, Anne Berit D Lingelem, Audun S Kvalvaag, Simona Kavaliauskiene, Andreas Brech, Gerbrand Koster, Paul G Dommersnes, Jonas Bergan, Tore Skotland, Kirsten Sandvig. Exogenous lysophospholipids with large head groups perturb clathrin-mediated endocytosis.
Traffic (Copenhagen, Denmark).
2017 03; 18(3):176-191. doi:
10.1111/tra.12468. [PMID: 28067430] - R X Yang, C X Hu, Y Q Mi, W L Sun, G Y Chen, Q Pan, F Shen, G W Xu, J G Fan. [A serum lipidomic study of patients with non-alcoholic fatty liver disease].
Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology.
2017 Feb; 25(2):122-127. doi:
10.3760/cma.j.issn.1007-3418.2017.02.009. [PMID: 28297799] - Makoto Kurano, Kuniyuki Kano, Tomotaka Dohi, Hirotaka Matsumoto, Koji Igarashi, Masako Nishikawa, Ryunosuke Ohkawa, Hitoshi Ikeda, Katsumi Miyauchi, Hiroyuki Daida, Junken Aoki, Yutaka Yatomi. Different origins of lysophospholipid mediators between coronary and peripheral arteries in acute coronary syndrome.
Journal of lipid research.
2017 02; 58(2):433-442. doi:
10.1194/jlr.p071803. [PMID: 28007846] - Mary A Lingerfelt, Pingwei Zhao, Haleli P Sharir, Dow P Hurst, Patricia H Reggio, Mary E Abood. Identification of Crucial Amino Acid Residues Involved in Agonist Signaling at the GPR55 Receptor.
Biochemistry.
2017 01; 56(3):473-486. doi:
10.1021/acs.biochem.6b01013. [PMID: 28005346] - Yonghai Lu, Yeli Wang, Choon-Nam Ong, Tavintharan Subramaniam, Hyung Won Choi, Jian-Min Yuan, Woon-Puay Koh, An Pan. Metabolic signatures and risk of type 2 diabetes in a Chinese population: an untargeted metabolomics study using both LC-MS and GC-MS.
Diabetologia.
2016 11; 59(11):2349-2359. doi:
10.1007/s00125-016-4069-2. [PMID: 27514531] - Josep M Del Bas, Antoni Caimari, Maria Isabel Rodriguez-Naranjo, Caroline E Childs, Carolina Paras Chavez, Annette L West, Elizabeth A Miles, Lluis Arola, Philip C Calder. Impairment of lysophospholipid metabolism in obesity: altered plasma profile and desensitization to the modulatory properties of n-3 polyunsaturated fatty acids in a randomized controlled trial.
The American journal of clinical nutrition.
2016 Aug; 104(2):266-79. doi:
10.3945/ajcn.116.130872. [PMID: 27305954] - Xu-Hong Lin, Dan-Dan Wei, Hui-Chao Wang, Bin Wang, Chun-Yang Bai, Ya-Qiang Wang, Guo-En Li, Hui-Ping Li, Xue-Qun Ren. [Role of orphan G protein-coupled receptor 55 in diabetic gastroparesis in mice].
Sheng li xue bao : [Acta physiologica Sinica].
2014 Jun; 66(3):332-40. doi:
. [PMID: 24964851] - Monica Imbernon, Lauren Whyte, Adenis Diaz-Arteaga, Wendy R Russell, Natalia R Moreno, María J Vazquez, Carmen R Gonzalez, Alberto Díaz-Ruiz, Miguel Lopez, Maria M Malagón, Ruth A Ross, Carlos Dieguez, Ruben Nogueiras. Regulation of GPR55 in rat white adipose tissue and serum LPI by nutritional status, gestation, gender and pituitary factors.
Molecular and cellular endocrinology.
2014 Mar; 383(1-2):159-69. doi:
10.1016/j.mce.2013.12.011. [PMID: 24378736] - Julia Kargl, Andrew J Brown, Liisa Andersen, Georg Dorn, Rudolf Schicho, Maria Waldhoer, Akos Heinemann. A selective antagonist reveals a potential role of G protein-coupled receptor 55 in platelet and endothelial cell function.
The Journal of pharmacology and experimental therapeutics.
2013 Jul; 346(1):54-66. doi:
10.1124/jpet.113.204180. [PMID: 23639801] - Julia Kargl, Nariman Balenga, Gerald P Parzmair, Andrew J Brown, Akos Heinemann, Maria Waldhoer. The cannabinoid receptor CB1 modulates the signaling properties of the lysophosphatidylinositol receptor GPR55.
The Journal of biological chemistry.
2012 Dec; 287(53):44234-48. doi:
10.1074/jbc.m112.364109. [PMID: 23161546] - Yutaro Obara, Sanae Ueno, Yoshimi Yanagihata, Norimichi Nakahata. Lysophosphatidylinositol causes neurite retraction via GPR55, G13 and RhoA in PC12 cells.
PloS one.
2011; 6(8):e24284. doi:
10.1371/journal.pone.0024284. [PMID: 21904624] - Lesley A Ford, Anke J Roelofs, Sharon Anavi-Goffer, Luisa Mowat, Daniel G Simpson, Andrew J Irving, Michael J Rogers, Ann M Rajnicek, Ruth A Ross. A role for L-alpha-lysophosphatidylinositol and GPR55 in the modulation of migration, orientation and polarization of human breast cancer cells.
British journal of pharmacology.
2010 Jun; 160(3):762-71. doi:
10.1111/j.1476-5381.2010.00743.x. [PMID: 20590578] - Christopher M Henstridge, Nariman A B Balenga, Lesley A Ford, Ruth A Ross, Maria Waldhoer, Andrew J Irving. The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2009 Jan; 23(1):183-93. doi:
10.1096/fj.08-108670. [PMID: 18757503] - Cheon Ho Park, Su Duy Nguyen, Mee Ree Kim, Tae-Sook Jeong, Dai-Eun Sok. Differential effect of lysophospholipids on activities of human plasma paraoxonase1, either soluble or lipid-bound.
Lipids.
2006 Apr; 41(4):371-80. doi:
10.1007/s11745-006-5108-4. [PMID: 16808151] - Yohei Noguchi, Atsushi Okamoto, Takeshi Kasama, Shinobu Imajoh-Ohmi, Takashi Karatsu, Hiroyuki Nogawa. Lysophosphatidic acid cooperates with EGF in inducing branching morphogenesis of embryonic mouse salivary epithelium.
Developmental dynamics : an official publication of the American Association of Anatomists.
2006 Feb; 235(2):403-10. doi:
10.1002/dvdy.20651. [PMID: 16317726] - Rebecca Sutphen, Yan Xu, George D Wilbanks, James Fiorica, Edward C Grendys, James P LaPolla, Hector Arango, Mitchell S Hoffman, Martin Martino, Katie Wakeley, David Griffin, Rafael W Blanco, Alan B Cantor, Yi-jin Xiao, Jeffrey P Krischer. Lysophospholipids are potential biomarkers of ovarian cancer.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2004 Jul; 13(7):1185-91. doi:
NULL. [PMID: 15247129] - Z Shen, M Wu, P Elson, A W Kennedy, J Belinson, G Casey, Y Xu. Fatty acid composition of lysophosphatidic acid and lysophosphatidylinositol in plasma from patients with ovarian cancer and other gynecological diseases.
Gynecologic oncology.
2001 Oct; 83(1):25-30. doi:
10.1006/gyno.2001.6357. [PMID: 11585410] - I H Lambert, B Falktoft. Lysophosphatidylcholine induces taurine release from HeLa cells.
The Journal of membrane biology.
2000 Jul; 176(2):175-85. doi:
10.1007/s00232001087. [PMID: 10926683] - S Miscia, A Di Baldassarre, A Cataldi, R A Rana, V Di Valerio, G Sabatino. Novel evidence of expression and activity of ecto-phospholipase C gamma1 in human T lymphocytes.
Blood.
1998 May; 91(10):3833-40. doi:
NULL. [PMID: 9573021] - T Kobayashi, M Kishimoto, H Okuyama. Phospholipases involved in lysophosphatidylinositol metabolism in rat brain.
Journal of lipid mediators and cell signalling.
1996 Sep; 14(1-3):33-7. doi:
10.1016/0929-7855(96)01505-2. [PMID: 8906542] - T Tsutsumi, T Kobayashi, H Ueda, E Yamauchi, S Watanabe, H Okuyama. Lysophosphoinositide-specific phospholipase C in rat brain synaptic plasma membranes.
Neurochemical research.
1994 Apr; 19(4):399-406. doi:
10.1007/bf00967316. [PMID: 8065496] - I Lassing, K Mellström, M Nistér. Comparison of PDGF-AA- and PDGF-BB-induced phosphoinositide formation in human and mouse fibroblasts.
Experimental cell research.
1994 Apr; 211(2):286-95. doi:
10.1006/excr.1994.1089. [PMID: 8143775] - R A MacQuarrie, F G Yao, G Y Sun. Effects of lysophospholipids and diacylglycerols on the transfer of arachidonic acid to phospholipids and triacylglycerols in rat brain membranes.
Neurochemistry international.
1993 Feb; 22(2):135-41. doi:
10.1016/0197-0186(93)90006-q. [PMID: 8439767] - J J Volwerk, G B Birrell, K K Hedberg, O H Griffith. A high level of cell surface phosphatidylinositol-specific phospholipase C activity is characteristic of growth-arrested 3T3 fibroblasts but not of transformed variants.
Journal of cellular physiology.
1992 Jun; 151(3):613-22. doi:
10.1002/jcp.1041510322. [PMID: 1338336] - J J Wheeler, W Gross, H Assefa, W F Boss. Phosphorylation of lysophosphatidylinositol by carrot membranes.
Biochimica et biophysica acta.
1991 Nov; 1086(3):310-6. doi:
10.1016/0005-2760(91)90175-h. [PMID: 1742323] - M Navidi, R A MacQuarrie, G Y Sun. Metabolism of phosphatidylinositol in plasma membranes and synaptosomes of rat cerebral cortex: a comparison between endogenous vs exogenous substrate pools.
Lipids.
1990 May; 25(5):273-7. doi:
10.1007/bf02544387. [PMID: 2112671] - F B Palmer. Identification of the phosphomonoesterases that hydrolyze lysopolyphosphoinositides in rat brain and liver.
Biochemistry and cell biology = Biochimie et biologie cellulaire.
1987 Oct; 65(10):890-8. doi:
10.1139/o87-115. [PMID: 2833909] - O Colard, D Bard, G Bereziat, J Polonovski. Acylation of endogenous phospholipids and added lysoderivatives by rat liver plasma membranes.
Biochimica et biophysica acta.
1980 Apr; 618(1):88-97. doi:
10.1016/0005-2760(80)90056-9. [PMID: 7378434]