9,10-Epoxystearic acid (BioDeep_00000004046)

Main id: BioDeep_00000009581

 

human metabolite blood metabolite


代谢物信息卡片


9,10-Epoxystearic acid, (trans)-isomer

化学式: C18H34O3 (298.2508)
中文名称: 9,10-环氧硬脂酸-d17
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCC1C(CCCCCCCC(=O)O)O1
InChI: InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)

描述信息

9,10-epoxystearate, also known as 18:0(9ep) or 9,10-epoxystearic acid, 14c-acid, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 9,10-epoxystearate is considered to be an octadecanoid lipid molecule. 9,10-epoxystearate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9,10-epoxystearate can be found in a number of food items such as garden cress, silver linden, european chestnut, and soft-necked garlic, which makes 9,10-epoxystearate a potential biomarker for the consumption of these food products.

同义名列表

18 个代谢物同义名

9,10-Epoxystearic acid, (trans)-isomer; 9,10-Epoxystearic acid, potassium salt; 9,10-Epoxystearic acid, ammonium salt; 9,10-Epoxystearic acid, (cis)-isomer; 9,10-Epoxystearic acid, sodium salt; 8-(3-Octyloxiran-2-yl)octanoic acid; 9,10-Epoxystearic acid, 14C-acid; 2-Oxiraneoctanoic acid,3-octyl-; 8-(3-Octyloxiran-2-yl)octanoate; 9S,10R-epoxy-octadecanoic acid; 9,10-epoxyoctadecanoic acid; cis-9,10-Epoxystearic acid; 9S,10R-epoxy-stearic acid; 9R,10S-epoxy-stearic acid; 9,10-Epoxyoctadecanoate; 9,10-EPOXYSTEARIC ACID; 9,10-Epoxystearate; cis-9,10-Epoxystearic acid



数据库引用编号

16 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)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ANXA5, CAT, HPGDS, LPO, ODC1, PLA2G12A, POLB, SREBF1
Peripheral membrane protein 2 ANXA5, CYP1B1
Endoplasmic reticulum membrane 3 CYP1B1, CYP3A7, SREBF1
Nucleus 3 POLB, PPARA, SREBF1
cytosol 8 ACOX1, ANXA5, CAT, DHODH, EPHX2, HPGDS, ODC1, SREBF1
nucleoplasm 6 ATP2B1, DHODH, HPGDS, POLB, PPARA, SREBF1
Cell membrane 1 ATP2B1
Multi-pass membrane protein 2 ATP2B1, SREBF1
Golgi apparatus membrane 1 SREBF1
Synapse 1 ATP2B1
glutamatergic synapse 1 ATP2B1
Golgi membrane 1 SREBF1
mitochondrial inner membrane 1 DHODH
presynaptic membrane 1 ATP2B1
sarcolemma 1 ANXA5
plasma membrane 1 ATP2B1
synaptic vesicle membrane 1 ATP2B1
Membrane 6 ACOX1, ANXA5, ATP2B1, CAT, CYP1B1, DHODH
basolateral plasma membrane 2 ATP2B1, LPO
extracellular exosome 5 ANXA5, ATP2B1, CAT, EPHX2, LPO
endoplasmic reticulum 1 SREBF1
extracellular space 1 LPO
mitochondrion 3 CAT, CYP1B1, DHODH
protein-containing complex 3 CAT, POLB, SREBF1
intracellular membrane-bounded organelle 4 ATP2B1, CAT, CYP1B1, HPGDS
Microsome membrane 2 CYP1B1, CYP3A7
Secreted 2 LPO, PLA2G12A
extracellular region 4 ANXA5, CAT, LPO, PLA2G12A
Single-pass membrane protein 1 DHODH
mitochondrial matrix 1 CAT
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 ANXA5
Mitochondrion inner membrane 1 DHODH
focal adhesion 2 ANXA5, CAT
microtubule 1 POLB
Peroxisome 3 ACOX1, CAT, EPHX2
Peroxisome matrix 1 CAT
peroxisomal matrix 3 ACOX1, CAT, EPHX2
peroxisomal membrane 2 ACOX1, CAT
collagen-containing extracellular matrix 1 ANXA5
lateral plasma membrane 1 ATP2B1
Zymogen granule membrane 1 ANXA5
chromatin 2 PPARA, SREBF1
cell projection 1 ATP2B1
Basolateral cell membrane 1 ATP2B1
nuclear envelope 1 SREBF1
Cytoplasmic vesicle membrane 1 SREBF1
Presynaptic cell membrane 1 ATP2B1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
immunological synapse 1 ATP2B1
ER to Golgi transport vesicle membrane 1 SREBF1
vesicle membrane 1 ANXA5
spindle microtubule 1 POLB
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
catalase complex 1 CAT
endothelial microparticle 1 ANXA5
photoreceptor ribbon synapse 1 ATP2B1
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1


文献列表

  • Kelsey Hildreth, Sean D Kodani, Bruce D Hammock, Ling Zhao. Cytochrome P450-derived linoleic acid metabolites EpOMEs and DiHOMEs: a review of recent studies. The Journal of nutritional biochemistry. 2020 12; 86(?):108484. doi: 10.1016/j.jnutbio.2020.108484. [PMID: 32827665]
  • Ying Liu, Jinwei Li, Yuanfa Liu. Effects of epoxy stearic acid on lipid metabolism in HepG2 cells. Journal of food science. 2020 Oct; 85(10):3644-3652. doi: 10.1111/1750-3841.15405. [PMID: 32885409]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Martina Decker, Magdalena Adamska, Annette Cronin, Francesca Di Giallonardo, Julia Burgener, Anne Marowsky, John R Falck, Christophe Morisseau, Bruce D Hammock, Artiom Gruzdev, Darryl C Zeldin, Michael Arand. EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides. Journal of lipid research. 2012 Oct; 53(10):2038-2045. doi: 10.1194/jlr.m024448. [PMID: 22798687]
  • Dimitrios Tsikas, Alexander A Zoerner, Jens Jordan. Oxidized and nitrated oleic acid in biological systems: analysis by GC-MS/MS and LC-MS/MS, and biological significance. Biochimica et biophysica acta. 2011 Nov; 1811(11):694-705. doi: 10.1016/j.bbalip.2011.06.015. [PMID: 21771665]
  • Thomas Thum, Sandor Batkai, Philipp G Malinski, Thomas Becker, Iris Mevius, Jürgen Klempnauer, Hartmut H Meyer, Jürgen C Frölich, Jürgen Borlak, Dimitrios Tsikas. Measurement and diagnostic use of hepatic cytochrome P450 metabolism of oleic acid in liver disease. Liver international : official journal of the International Association for the Study of the Liver. 2010 Sep; 30(8):1181-8. doi: 10.1111/j.1478-3231.2010.02310.x. [PMID: 20629947]
  • Hui Li, Franck Pinot, Vincent Sauveplane, Danièle Werck-Reichhart, Patrik Diehl, Lukas Schreiber, Rochus Franke, Ping Zhang, Liang Chen, Yawei Gao, Wanqi Liang, Dabing Zhang. Cytochrome P450 family member CYP704B2 catalyzes the {omega}-hydroxylation of fatty acids and is required for anther cutin biosynthesis and pollen exine formation in rice. The Plant cell. 2010 Jan; 22(1):173-90. doi: 10.1105/tpc.109.070326. [PMID: 20086189]
  • Vincent Sauveplane, Sylvie Kandel, Pierre-Edouard Kastner, Jürgen Ehlting, Vincent Compagnon, Danièle Werck-Reichhart, Franck Pinot. Arabidopsis thaliana CYP77A4 is the first cytochrome P450 able to catalyze the epoxidation of free fatty acids in plants. The FEBS journal. 2009 Feb; 276(3):719-35. doi: 10.1111/j.1742-4658.2008.06819.x. [PMID: 19120447]
  • Jean-François Rontani, Ian Jameson, Stéphane Christodoulou, John K Volkman. Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi. Phytochemistry. 2007 Mar; 68(6):913-24. doi: 10.1016/j.phytochem.2006.12.013. [PMID: 17258251]
  • Sylvie Kandel, Marc Morant, Irène Benveniste, Elizabeth Blée, Danièle Werck-Reichhart, Franck Pinot. Cloning, functional expression, and characterization of CYP709C1, the first sub-terminal hydroxylase of long chain fatty acid in plants. Induction by chemicals and methyl jasmonate. The Journal of biological chemistry. 2005 Oct; 280(43):35881-9. doi: 10.1074/jbc.m500918200. [PMID: 16120613]
  • Valérie Le Quéré, Emmanuelle Plée-Gautier, Philippe Potin, Stéphanie Madec, Jean-Pierre Salaün. Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides. Journal of lipid research. 2004 Aug; 45(8):1446-58. doi: 10.1194/jlr.m300463-jlr200. [PMID: 15145985]
  • Joaquín Velasco, Susana Marmesat, Olivier Bordeaux, Gloria Márquez-Ruiz, Carmen Dobarganes. Formation and evolution of monoepoxy fatty acids in thermoxidized olive and sunflower oils and quantitation in used frying oils from restaurants and fried-food outlets. Journal of agricultural and food chemistry. 2004 Jul; 52(14):4438-43. doi: 10.1021/jf030753f. [PMID: 15237949]
  • Dimitrios Tsikas, Anja Mitschke, Frank-Mathias Gutzki, Hartmut H Meyer, Jürgen C Frölich. Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). II. Quantitative determination of cis-EODA in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 May; 804(2):403-12. doi: 10.1016/j.jchromb.2004.01.055. [PMID: 15081936]
  • Dimitrios Tsikas, Masayuki Sawa, Gorig Brunner, Frank Mathias Gutzki, Hartmut H Meyer, Jürgen C Frölich. Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Feb; 784(2):351-65. doi: 10.1016/s1570-0232(02)00821-8. [PMID: 12505783]
  • Stephan Summerer, Abdulsamie Hanano, Shigeru Utsumi, Michael Arand, Francis Schuber, Elizabeth Blée. Stereochemical features of the hydrolysis of 9,10-epoxystearic acid catalysed by plant and mammalian epoxide hydrolases. The Biochemical journal. 2002 Sep; 366(Pt 2):471-80. doi: 10.1042/bj20011778. [PMID: 12020347]
  • F Pinot, I Benveniste, J P Salaün, O Loreau, J P Noël, L Schreiber, F Durst. Production in vitro by the cytochrome P450 CYP94A1 of major C18 cutin monomers and potential messengers in plant-pathogen interactions: enantioselectivity studies. The Biochemical journal. 1999 Aug; 342 ( Pt 1)(?):27-32. doi: 10.1042/0264-6021:3420027. [PMID: 10432296]
  • E S Kaneshiro. Lipid metabolism of Pneumocystis: toward the definition of new molecular targets. FEMS immunology and medical microbiology. 1998 Sep; 22(1-2):135-43. doi: 10.1111/j.1574-695x.1998.tb01198.x. [PMID: 9792072]
  • V Spitzer, W Tomberg, R Hartmann, R Aichholz. Analysis of the seed oil of Heisteria silvanii (Olacaceae)--a rich source of a novel C18 acetylenic fatty acid. Lipids. 1997 Nov; 32(11):1189-200. doi: 10.1007/s11745-997-0153-6. [PMID: 9397405]
  • G A Ulsaker, G Teien. Identification of 9,10-epoxyoctadecanoic acid in human urine using gas chromatography-mass spectrometry. Biomedical chromatography : BMC. 1995 Jul; 9(4):183-7. doi: 10.1002/bmc.1130090407. [PMID: 8520208]
  • E Blée, F Schuber. Regio- and enantioselectivity of soybean fatty acid epoxide hydrolase. The Journal of biological chemistry. 1992 Jun; 267(17):11881-7. doi: . [PMID: 1601858]
  • R Sharma, S Gupta, S S Singhal, G A Ansari, Y C Awasthi. Glutathione S-transferase-catalyzed conjugation of 9,10-epoxystearic acid with glutathione. Journal of biochemical toxicology. 1991; 6(2):147-53. doi: 10.1002/jbt.2570060209. [PMID: 1941901]
  • A P TULLOCH, B M CRAIG, G A LEDINGHAM. The oil of wheat stem rust uredospores. II. The isolation of cis-9,10-epoxyoctadecanoic acid, and the fatty acid composition of the oil. Canadian journal of microbiology. 1959 Oct; 5(?):485-91. doi: 10.1139/m59-060. [PMID: 13839791]