Minerval (BioDeep_00000629100)
代谢物信息卡片
9-Octadecenoic acid, 2-hydroxy-, (9Z)-
化学式: C18H34O3 (298.2508)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(general) 100%
分子结构信息
SMILES: C(C(O)CCCCCC/C=C\CCCCCCCC)(=O)O
InChI: InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-
描述信息
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor
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)
0 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 |
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文献列表
- Kumudesh Mishra, Mária Péter, Anna Maria Nardiello, Guy Keller, Victoria Llado, Paula Fernandez-Garcia, Ulf D Kahlert, Dinorah Barasch, Ann Saada, Zsolt Török, Gábor Balogh, Pablo V Escriba, Stefano Piotto, Or Kakhlon. Multifaceted Analyses of Isolated Mitochondria Establish the Anticancer Drug 2-Hydroxyoleic Acid as an Inhibitor of Substrate Oxidation and an Activator of Complex IV-Dependent State 3 Respiration.
Cells.
2022 02; 11(3):. doi:
10.3390/cells11030578. [PMID: 35159387] - Noemí Redondo Useros, Alina Gheorghe, Fátima Perez de Heredia, Ligia E Díaz, Gyselle Chrystina Baccan, Mónica De la Fuente, Ascensión Marcos. 2-OHOA supplementation reduced adiposity and improved cardiometabolic risk to a greater extent than n-3 PUFA in obese mice.
Obesity research & clinical practice.
2019 Nov; 13(6):579-585. doi:
10.1016/j.orcp.2019.10.009. [PMID: 31787558] - Karolina Olechowska, Marzena Mach, Katarzyna Ha C-Wydro, Paweł Wydro. Studies on the Interactions of 2-Hydroxyoleic Acid with Monolayers and Bilayers Containing Cationic Lipid: Searching for the Formulations for More Efficient Drug Delivery to Cancer Cells.
Langmuir : the ACS journal of surfaces and colloids.
2019 07; 35(27):9084-9092. doi:
10.1021/acs.langmuir.9b01326. [PMID: 31246038] - Rama Prajapati, Mark Gontsarik, Anan Yaghmur, Stefan Salentinig. pH-Responsive Nano-Self-Assemblies of the Anticancer Drug 2-Hydroxyoleic Acid.
Langmuir : the ACS journal of surfaces and colloids.
2019 06; 35(24):7954-7961. doi:
10.1021/acs.langmuir.9b00838. [PMID: 31150248] - Wessal Massalha, Mark Markovits, Edward Pichinuk, Yael Feinstein-Rotkopf, Mark Tarshish, Kumudesh Mishra, Victoria Llado, Miguel Weil, Pablo V Escriba, Or Kakhlon. Minerval (2-hydroxyoleic acid) causes cancer cell selective toxicity by uncoupling oxidative phosphorylation and compromising bioenergetic compensation capacity.
Bioscience reports.
2019 01; 39(1):. doi:
10.1042/bsr20181661. [PMID: 30602451] - Bin Lou, Qi Liu, Jiahui Hou, Inamul Kabir, Peipei Liu, Tingbo Ding, Jibin Dong, Mingguang Mo, Deyong Ye, Yang Chen, Hai H Bui, Kenneth Roth, Yu Cao, Xian-Cheng Jiang. 2-Hydroxy-oleic acid does not activate sphingomyelin synthase activity.
The Journal of biological chemistry.
2018 11; 293(47):18328-18336. doi:
10.1074/jbc.ra118.005904. [PMID: 30305392] - Karolina Węder, Marzena Mach, Katarzyna Hąc-Wydro, Paweł Wydro. Studies on the interactions of anticancer drug - Minerval - with membrane lipids in binary and ternary Langmuir monolayers.
Biochimica et biophysica acta. Biomembranes.
2018 11; 1860(11):2329-2336. doi:
10.1016/j.bbamem.2018.05.019. [PMID: 29864405] - Caroline Hunsche, Oskarina Hernandez, Alina Gheorghe, Ligia Esperanza Díaz, Ascensión Marcos, Mónica De la Fuente. Immune dysfunction and increased oxidative stress state in diet-induced obese mice are reverted by nutritional supplementation with monounsaturated and n-3 polyunsaturated fatty acids.
European journal of nutrition.
2018 Apr; 57(3):1123-1135. doi:
10.1007/s00394-017-1395-1. [PMID: 28229279] - Eun-Ji Jang, Woo Rim Choi, Soo-Yeon Kim, Soon-Seok Hong, Inmoo Rhee, Sang-Jin Lee, Sung Weon Choi, Han-Gon Choi, Soo-Jeong Lim. 2-Hydroxyoleic acid-inserted liposomes as a multifunctional carrier of anticancer drugs.
Drug delivery.
2017 Nov; 24(1):1587-1597. doi:
10.1080/10717544.2017.1388452. [PMID: 29029595] - Iriana Galán-Arriero, Diego Serrano-Muñoz, Julio Gómez-Soriano, Carlos Goicoechea, Julian Taylor, Ana Velasco, Gerardo Ávila-Martín. The role of Omega-3 and Omega-9 fatty acids for the treatment of neuropathic pain after neurotrauma.
Biochimica et biophysica acta. Biomembranes.
2017 Sep; 1859(9 Pt B):1629-1635. doi:
10.1016/j.bbamem.2017.05.003. [PMID: 28495596] - Alina Gheorghe, Fátima Pérez de Heredia, Caroline Hunsche, Noemí Redondo, Ligia Esperanza Díaz, Oskarina Hernández, Ascensión Marcos, Mónica De la Fuente. Oxidative stress and immunosenescence in spleen of obese mice can be reversed by 2-hydroxyoleic acid.
Experimental physiology.
2017 05; 102(5):533-544. doi:
10.1113/ep086157. [PMID: 28205317] - Maria L Torgersen, Tove Irene Klokk, Simona Kavaliauskiene, Christian Klose, Kai Simons, Tore Skotland, Kirsten Sandvig. The anti-tumor drug 2-hydroxyoleic acid (Minerval) stimulates signaling and retrograde transport.
Oncotarget.
2016 Dec; 7(52):86871-86888. doi:
10.18632/oncotarget.13508. [PMID: 27894086] - Roberto Fernández, Jone Garate, Sergio Lage, Silvia Terés, Mónica Higuera, Joan Bestard-Escalas, M Laura Martin, Daniel H López, Francisca Guardiola-Serrano, Pablo V Escribá, Gwendolyn Barceló-Coblijn, José A Fernández. Optimized Protocol To Analyze Changes in the Lipidome of Xenografts after Treatment with 2-Hydroxyoleic Acid.
Analytical chemistry.
2016 Jan; 88(1):1022-9. doi:
10.1021/acs.analchem.5b03978. [PMID: 26607740] - Stefano Piotto, Simona Concilio, Erminia Bianchino, Pio Iannelli, David J López, Silvia Terés, Maitane Ibarguren, Gwendolyn Barceló-Coblijn, Maria Laura Martin, Francisca Guardiola-Serrano, María Alonso-Sande, Sérgio S Funari, Xavier Busquets, Pablo V Escribá. Differential effect of 2-hydroxyoleic acid enantiomers on protein (sphingomyelin synthase) and lipid (membrane) targets.
Biochimica et biophysica acta.
2014 Jun; 1838(6):1628-37. doi:
10.1016/j.bbamem.2013.12.023. [PMID: 24412218] - Stefano Piotto, Alfonso Trapani, Erminia Bianchino, Maitane Ibarguren, David J López, Xavier Busquets, Simona Concilio. The effect of hydroxylated fatty acid-containing phospholipids in the remodeling of lipid membranes.
Biochimica et biophysica acta.
2014 Jun; 1838(6):1509-17. doi:
10.1016/j.bbamem.2014.01.014. [PMID: 24463068] - Victoria Lladó, David J López, Maitane Ibarguren, María Alonso, Joan B Soriano, Pablo V Escribá, Xavier Busquets. Regulation of the cancer cell membrane lipid composition by NaCHOleate: effects on cell signaling and therapeutical relevance in glioma.
Biochimica et biophysica acta.
2014 Jun; 1838(6):1619-27. doi:
10.1016/j.bbamem.2014.01.027. [PMID: 24525074] - Maria Laura Martin, Gwendolyn Barceló-Coblijn, Rodrigo F M de Almeida, Maria Antònia Noguera-Salvà, Silvia Terés, Mónica Higuera, Gerhard Liebisch, Gerd Schmitz, Xavier Busquets, Pablo V Escribá. The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid.
Biochimica et biophysica acta.
2013 May; 1828(5):1405-13. doi:
10.1016/j.bbamem.2013.01.013. [PMID: 23360770] - Maria Laura Martin, Gerhard Liebisch, Stefan Lehneis, Gerd Schmitz, María Alonso-Sande, Joan Bestard-Escalas, Daniel H Lopez, José Manuel García-Verdugo, Mario Soriano-Navarro, Xavier Busquets, Pablo V Escribá, Gwendolyn Barceló-Coblijn. Sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells.
Journal of lipid research.
2013 May; 54(5):1457-65. doi:
10.1194/jlr.m036749. [PMID: 23471028] - Jesús Prades, Sérgio S Funari, Manuel Gomez-Florit, Oliver Vögler, Francisca Barceló. Effect of a 2-hydroxylated fatty acid on cholesterol-rich membrane domains.
Molecular membrane biology.
2012 Dec; 29(8):333-43. doi:
10.3109/09687688.2012.705023. [PMID: 22830943] - Silvia Terés, Victoria Lladó, Mónica Higuera, Gwendolyn Barceló-Coblijn, M Laura Martin, Maria Antònia Noguera-Salvà, Amaia Marcilla-Etxenike, José Manuel García-Verdugo, Mario Soriano-Navarro, Carlos Saus, Ulises Gómez-Pinedo, Xavier Busquets, Pablo V Escribá. Normalization of sphingomyelin levels by 2-hydroxyoleic acid induces autophagic cell death of SF767 cancer cells.
Autophagy.
2012 Oct; 8(10):1542-4. doi:
10.4161/auto.21341. [PMID: 22892762] - Silvia Terés, Victoria Lladó, Mónica Higuera, Gwendolyn Barceló-Coblijn, Maria Laura Martin, Maria Antònia Noguera-Salvà, Amaia Marcilla-Etxenike, José Manuel García-Verdugo, Mario Soriano-Navarro, Carlos Saus, Ulises Gómez-Pinedo, Xavier Busquets, Pablo V Escribá. 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy.
Proceedings of the National Academy of Sciences of the United States of America.
2012 May; 109(22):8489-94. doi:
10.1073/pnas.1118349109. [PMID: 22586083] - Gwendolyn Barceló-Coblijn, Maria Laura Martin, Rodrigo F M de Almeida, Maria Antònia Noguera-Salvà, Amaia Marcilla-Etxenike, Francisca Guardiola-Serrano, Anja Lüth, Burhard Kleuser, John E Halver, Pablo V Escribá. Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy.
Proceedings of the National Academy of Sciences of the United States of America.
2011 Dec; 108(49):19569-74. doi:
10.1073/pnas.1115484108. [PMID: 22106271] - Javier Cerezo, José Zúñiga, Adolfo Bastida, Alberto Requena, José Pedro Cerón-Carrasco. Atomistic molecular dynamics simulations of the interactions of oleic and 2-hydroxyoleic acids with phosphatidylcholine bilayers.
The journal of physical chemistry. B.
2011 Oct; 115(40):11727-38. doi:
10.1021/jp203498x. [PMID: 21882864] - Victoria Llado, Antonio Gutierrez, Jordi Martínez, Jesús Casas, Silvia Terés, Mónica Higuera, Antonio Galmés, Carles Saus, Joan Besalduch, Xavier Busquets, Pablo V Escribá. Minerval induces apoptosis in Jurkat and other cancer cells.
Journal of cellular and molecular medicine.
2010 Mar; 14(3):659-70. doi:
10.1111/j.1582-4934.2008.00625.x. [PMID: 19413889] - Victoria Lladó, Silvia Terés, Mónica Higuera, Rafael Alvarez, Maria Antònia Noguera-Salva, John E Halver, Pablo V Escribá, Xavier Busquets. Pivotal role of dihydrofolate reductase knockdown in the anticancer activity of 2-hydroxyoleic acid.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Aug; 106(33):13754-8. doi:
10.1073/pnas.0907300106. [PMID: 19666584] - Gudrun H Borchert, Mike Giggey, Frantisek Kolar, Tak Ming Wong, Peter H Backx, Pablo V Escriba. 2-hydroxyoleic acid affects cardiomyocyte [Ca2+]i transient and contractility in a region-dependent manner.
American journal of physiology. Heart and circulatory physiology.
2008 Apr; 294(4):H1948-55. doi:
10.1152/ajpheart.01209.2007. [PMID: 18296566] - O Vögler, A López-Bellan, R Alemany, S Tofé, M González, J Quevedo, V Pereg, F Barceló, P V Escriba. Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats.
International journal of obesity (2005).
2008 Mar; 32(3):464-73. doi:
10.1038/sj.ijo.0803768. [PMID: 18059405] - Jesús Prades, Regina Alemany, Javier S Perona, Sérgio S Funari, Oliver Vögler, Valentina Ruiz-Gutiérrez, Pablo V Escribá, Francisca Barceló. Effects of 2-hydroxyoleic acid on the structural properties of biological and model plasma membranes.
Molecular membrane biology.
2008 Jan; 25(1):46-57. doi:
10.1080/09687680701510042. [PMID: 17852735] - Regina Alemany, Oliver Vögler, Silvia Terés, Carolina Egea, Carmela Baamonde, Francisca Barceló, Carlos Delgado, Karl H Jakobs, Pablo V Escribá. Antihypertensive action of 2-hydroxyoleic acid in SHRs via modulation of the protein kinase A pathway and Rho kinase.
Journal of lipid research.
2006 Aug; 47(8):1762-70. doi:
10.1194/jlr.m500520-jlr200. [PMID: 16687663] - Jordi Martínez, Oliver Vögler, Jesús Casas, Francisca Barceló, Regina Alemany, Jesús Prades, Tünde Nagy, Carmela Baamonde, Philip G Kasprzyk, Silvia Terés, Carlos Saus, Pablo V Escribá. Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval.
Molecular pharmacology.
2005 Feb; 67(2):531-40. doi:
10.1124/mol.104.000778. [PMID: 15531732] - Francisca Barceló, Jesús Prades, Sérgio S Funari, Juan Frau, Regina Alemany, Pablo V Escribá. The hypotensive drug 2-hydroxyoleic acid modifies the structural properties of model membranes.
Molecular membrane biology.
2004 Jul; 21(4):261-8. doi:
10.1080/09687680410001716835. [PMID: 15371015]
