13-Hydroxyoctadeca-2,4-dienoic acid (BioDeep_00000173796)
human metabolite blood metabolite
代谢物信息卡片
13-HYDROXYOCTADECA-2,4-DIENOIC ACID
化学式: C18H32O3 (296.2351322)
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: CCCCCC(O)CCCCCCCC=CC=CC(O)=O
InChI: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h8,10,13,16-17,19H,2-7,9,11-12,14-15H2,1H3,(H,20,21)
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
- Helena Viita, Agnieszka Pacholska, Farizan Ahmad, Johanna Tietäväinen, Jonne Naarala, Anna Hyvärinen, Thomas Wirth, Seppo Ylä-Herttuala. 15-Lipoxygenase-1 induces lipid peroxidation and apoptosis, and improves survival in rat malignant glioma.
In vivo (Athens, Greece).
2012 Jan; 26(1):1-8. doi:
". [PMID: 22210710] - Raquel Martín-Venegas, Rosario Casillas, Olga Jáuregui, Juan José Moreno. Rapid simultaneous analysis of cyclooxygenase, lipoxygenase and cytochrome P-450 metabolites of arachidonic and linoleic acids using high performance liquid chromatography/mass spectrometry in tandem mode.
Journal of pharmaceutical and biomedical analysis.
2011 Dec; 56(5):976-82. doi:
10.1016/j.jpba.2011.06.018. [PMID: 21880455] - Sun Il Lee, Xiangsheng Zuo, Imad Shureiqi. 15-Lipoxygenase-1 as a tumor suppressor gene in colon cancer: is the verdict in?.
Cancer metastasis reviews.
2011 Dec; 30(3-4):481-91. doi:
10.1007/s10555-011-9321-0. [PMID: 22037943] - Ines Kämmerer, Robert Ringseis, Ronald Biemann, Gaiping Wen, Klaus Eder. 13-hydroxy linoleic acid increases expression of the cholesterol transporters ABCA1, ABCG1 and SR-BI and stimulates apoA-I-dependent cholesterol efflux in RAW264.7 macrophages.
Lipids in health and disease.
2011 Nov; 10(?):222. doi:
10.1186/1476-511x-10-222. [PMID: 22129452] - Christopher E Ramsden, J Douglas Mann, Keturah R Faurot, Chanee Lynch, Syed Taha Imam, Beth A MacIntosh, Joseph R Hibbeln, James Loewke, Sunyata Smith, Rebecca Coble, Chirayath Suchindran, Susan A Gaylord. Low omega-6 vs. low omega-6 plus high omega-3 dietary intervention for chronic daily headache: protocol for a randomized clinical trial.
Trials.
2011 Apr; 12(?):97. doi:
10.1186/1745-6215-12-97. [PMID: 21496264] - Olav A Christophersen, Anna Haug. Animal products, diseases and drugs: a plea for better integration between agricultural sciences, human nutrition and human pharmacology.
Lipids in health and disease.
2011 Jan; 10(?):16. doi:
10.1186/1476-511x-10-16. [PMID: 21247506] - Etsuo Niki. Do free radicals play causal role in atherosclerosis? Low density lipoprotein oxidation and vitamin E revisited.
Journal of clinical biochemistry and nutrition.
2011 Jan; 48(1):3-7. doi:
10.3164/jcbn.11-007fr. [PMID: 21297905] - Susanna L Lundström, Bettina Levänen, Malin Nording, Anna Klepczynska-Nyström, Magnus Sköld, Jesper Z Haeggström, Johan Grunewald, Magnus Svartengren, Bruce D Hammock, Britt-Marie Larsson, Anders Eklund, Åsa M Wheelock, Craig E Wheelock. Asthmatics exhibit altered oxylipin profiles compared to healthy individuals after subway air exposure.
PloS one.
2011; 6(8):e23864. doi:
10.1371/journal.pone.0023864. [PMID: 21897859] - Cecilia Morgantini, Satoshi Imaizumi, Victor Grijalva, Mohamad Navab, Alan M Fogelman, Srinivasa T Reddy. Apolipoprotein A-I mimetic peptides prevent atherosclerosis development and reduce plaque inflammation in a murine model of diabetes.
Diabetes.
2010 Dec; 59(12):3223-8. doi:
10.2337/db10-0844. [PMID: 20826564] - Ming-Yue Li, Huiling Yuan, Lily T Ma, Angel W Y Kong, Michael K Y Hsin, Johnson H Y Yip, Malcolm J Underwood, George G Chen. Roles of peroxisome proliferator-activated receptor-alpha and -gamma in the development of non-small cell lung cancer.
American journal of respiratory cell and molecular biology.
2010 Dec; 43(6):674-83. doi:
10.1165/rcmb.2009-0349oc. [PMID: 20081051] - Betul Catalgol, Nesrin Kartal Ozer. Lipid rafts and redox regulation of cellular signaling in cholesterol induced atherosclerosis.
Current cardiology reviews.
2010 Nov; 6(4):309-24. doi:
10.2174/157340310793566181. [PMID: 22043207] - Dan Wang, Svend Strandgaard, Jens Iversen, Christopher S Wilcox. Asymmetric dimethylarginine, oxidative stress, and vascular nitric oxide synthase in essential hypertension.
American journal of physiology. Regulatory, integrative and comparative physiology.
2009 Feb; 296(2):R195-200. doi:
10.1152/ajpregu.90506.2008. [PMID: 18685064] - S Ortega-Gutiérrez, M López-Vicente, F Lostalé, L Fuentes-Broto, E Martínez-Ballarín, J J García. Protective effect of melatonin against mitomycin C-induced genotoxic damage in peripheral blood of rats.
Journal of biomedicine & biotechnology.
2009; 2009(?):791432. doi:
10.1155/2009/791432. [PMID: 19859567] - Rona Limor, Orly Sharon, Esther Knoll, Ariel Many, Gary Weisinger, Naftali Stern. Lipoxygenase-derived metabolites are regulators of peroxisome proliferator-activated receptor gamma-2 expression in human vascular smooth muscle cells.
American journal of hypertension.
2008 Feb; 21(2):219-23. doi:
10.1038/ajh.2007.39. [PMID: 18202670] - Dan Wang, Svend Strandgaard, Malene L Borresen, Zaiming Luo, Stephanie G Connors, Qing Yan, Christopher S Wilcox. Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease.
American journal of kidney diseases : the official journal of the National Kidney Foundation.
2008 Feb; 51(2):184-91. doi:
10.1053/j.ajkd.2007.09.020. [PMID: 18215696] - Paola Manini, Emanuela Camera, Mauro Picardo, Alessandra Napolitano, Marco d'Ischia. Biomimetic nitration of the linoleic acid metabolite 13-hydroxyoctadecadienoic acid: isolation and spectral characterization of novel chain-rearranged epoxy nitro derivatives.
Chemistry and physics of lipids.
2008 Jan; 151(1):51-61. doi:
10.1016/j.chemphyslip.2007.09.007. [PMID: 18320610] - Sheng Zhong Duan, Christine Y Ivashchenko, Michael G Usher, Richard M Mortensen. PPAR-gamma in the Cardiovascular System.
PPAR research.
2008; 2008(?):745804. doi:
10.1155/2008/745804. [PMID: 18288291] - Ingrid Emerit. Clastogenic factors as potential biomarkers of increased superoxide production.
Biomarker insights.
2007 Dec; 2(?):429-38. doi:
10.1177/117727190700200010. [PMID: 19662223] - Dorothea Schweiger, Gerhard Fürstenberger, Peter Krieg. Inducible expression of 15-lipoxygenase-2 and 8-lipoxygenase inhibits cell growth via common signaling pathways.
Journal of lipid research.
2007 Mar; 48(3):553-64. doi:
10.1194/jlr.m600311-jlr200. [PMID: 17164225] - Jane Elizabeth Ward, Xiahui Tan. Peroxisome proliferator activated receptor ligands as regulators of airway inflammation and remodelling in chronic lung disease.
PPAR research.
2007; 2007(?):14983. doi:
10.1155/2007/14983. [PMID: 18000530] - S Aslam, T Santha, A Leone, C Wilcox. Effects of amlodipine and valsartan on oxidative stress and plasma methylarginines in end-stage renal disease patients on hemodialysis.
Kidney international.
2006 Dec; 70(12):2109-15. doi:
10.1038/sj.ki.5001983. [PMID: 17063175] - Sarah Chouinard, Georges Pelletier, Alain Bélanger, Olivier Barbier. Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation.
Endocrinology.
2006 Nov; 147(11):5431-42. doi:
10.1210/en.2006-0229. [PMID: 16887906] - Stacy K Seeley, Julie A Poposki, John Maksimchuk, Jill Tebbe, Jon Gaudreau, Bengt Mannervik, Arthur W Bull. Metabolism of oxidized linoleic acid by glutathione transferases: peroxidase activity toward 13-hydroperoxyoctadecadienoic acid.
Biochimica et biophysica acta.
2006 Jul; 1760(7):1064-70. doi:
10.1016/j.bbagen.2006.02.020. [PMID: 16624487] - Gautam Damera, Baoyun Xia, Goverdhan P Sachdev. IL-4 induced MUC4 enhancement in respiratory epithelial cells in vitro is mediated through JAK-3 selective signaling.
Respiratory research.
2006 Mar; 7(?):39. doi:
10.1186/1465-9921-7-39. [PMID: 16551361] - Patrick Mathieu, Philippe Pibarot, Jean-Pierre Després. Metabolic syndrome: the danger signal in atherosclerosis.
Vascular health and risk management.
2006; 2(3):285-302. doi:
10.2147/vhrm.2006.2.3.285. [PMID: 17326334] - Junji Terao, Mio Hiwada, Keiko Taguchi, Keigo Takahara, Satoshi Mohri. Glutathione peroxidase mimics as novel antioxidants from vegetables.
BioFactors (Oxford, England).
2005; 23(1):1-6. doi:
10.1002/biof.5520230101. [PMID: 15817993] - Uddhav P Kelavkar, Wayne Glasgow, Sandra J Olson, Barbara A Foster, Scott B Shappell. Overexpression of 12/15-lipoxygenase, an ortholog of human 15-lipoxygenase-1, in the prostate tumors of TRAMP mice.
Neoplasia (New York, N.Y.).
2004 Nov; 6(6):821-30. doi:
10.1593/neo.04286. [PMID: 15720809] - Vicent Ribas, José Luis Sánchez-Quesada, Rosa Antón, Mercedes Camacho, Josep Julve, Joan Carles Escolà-Gil, Luís Vila, Jordi Ordóñez-Llanos, Francisco Blanco-Vaca. Human apolipoprotein A-II enrichment displaces paraoxonase from HDL and impairs its antioxidant properties: a new mechanism linking HDL protein composition and antiatherogenic potential.
Circulation research.
2004 Oct; 95(8):789-97. doi:
10.1161/01.res.0000146031.94850.5f. [PMID: 15388641] - David E Blask, Robert T Dauchy, Leonard A Sauer, Jean A Krause. Melatonin uptake and growth prevention in rat hepatoma 7288CTC in response to dietary melatonin: melatonin receptor-mediated inhibition of tumor linoleic acid metabolism to the growth signaling molecule 13-hydroxyoctadecadienoic acid and the potential role of phytomelatonin.
Carcinogenesis.
2004 Jun; 25(6):951-60. doi:
10.1093/carcin/bgh090. [PMID: 14754876] - Michiharu Tanabe, Sadaharu Tabuchi, Masato Iwatsuki, Masamichi Kurosaki, Hideki Kamitani, Masayuki Yokota, Takashi Watanabe. Incorporation of arachidonic and linoleic acid hydroperoxides into cultured human umbilical vein endothelial cells.
Prostaglandins, leukotrienes, and essential fatty acids.
2004 Jun; 70(6):485-9. doi:
10.1016/j.plefa.2003.10.003. [PMID: 15120710] - Satoshi Akiba. [Involvement of phospholipase A2 in the supply of fatty acids required for cholesterol esterification associated with uptake of oxidized low-density lipoprotein in macrophages].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2003 Oct; 123(10):845-53. doi:
10.1248/yakushi.123.845. [PMID: 14577330] - David Turgeon, Sarah Chouinard, Patrick Belanger, Serge Picard, Jean-Francois Labbe, Pierre Borgeat, Alain Belanger. Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases.
Journal of lipid research.
2003 Jun; 44(6):1182-91. doi:
10.1194/jlr.m300010-jlr200. [PMID: 12639971] - Wei-Gen Li, Lynn L Stoll, James B Rice, Shao-Ping Xu, Francis J Miller, Papri Chatterjee, Ling Hu, Larry W Oberley, Arthur A Spector, Neal L Weintraub. Activation of NAD(P)H oxidase by lipid hydroperoxides: mechanism of oxidant-mediated smooth muscle cytotoxicity.
Free radical biology & medicine.
2003 Apr; 34(7):937-46. doi:
10.1016/s0891-5849(03)00032-7. [PMID: 12654483] - Yuchang Fu, Nanlan Luo, Maria F Lopes-Virella, W Timothy Garvey. The adipocyte lipid binding protein (ALBP/aP2) gene facilitates foam cell formation in human THP-1 macrophages.
Atherosclerosis.
2002 Dec; 165(2):259-69. doi:
10.1016/s0021-9150(02)00305-2. [PMID: 12417276] - Claudia Traidl-Hoffmann, Anna Kasche, Thilo Jakob, Michael Huger, Sabine Plötz, Ivo Feussner, Johannes Ring, Heidrun Behrendt. Lipid mediators from pollen act as chemoattractants and activators of polymorphonuclear granulocytes.
The Journal of allergy and clinical immunology.
2002 May; 109(5):831-8. doi:
10.1067/mai.2002.124655. [PMID: 11994708] - Barbara Fischer, Andreas von Knethen, Bernhard Brüne. Dualism of oxidized lipoproteins in provoking and attenuating the oxidative burst in macrophages: role of peroxisome proliferator-activated receptor-gamma.
Journal of immunology (Baltimore, Md. : 1950).
2002 Mar; 168(6):2828-34. doi:
10.4049/jimmunol.168.6.2828. [PMID: 11884452] - B A Ek-Von Mentzer, F Zhang, J A Hamilton. Binding of 13-HODE and 15-HETE to phospholipid bilayers, albumin, and intracellular fatty acid binding proteins. implications for transmembrane and intracellular transport and for protection from lipid peroxidation.
The Journal of biological chemistry.
2001 May; 276(19):15575-80. doi:
10.1074/jbc.m011623200. [PMID: 11278949] - P Dandona, P Mohanty, H Ghanim, A Aljada, R Browne, W Hamouda, A Prabhala, A Afzal, R Garg. The suppressive effect of dietary restriction and weight loss in the obese on the generation of reactive oxygen species by leukocytes, lipid peroxidation, and protein carbonylation.
The Journal of clinical endocrinology and metabolism.
2001 Jan; 86(1):355-62. doi:
10.1210/jcem.86.1.7150. [PMID: 11232024]