13-OxoODE (BioDeep_00000003301)

 

Secondary id: BioDeep_00000174142, BioDeep_00000396740, BioDeep_00000397606

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(9Z,11E)-13-Oxooctadeca-9,11-dienoic acid

化学式: C18H30O3 (294.21948299999997)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.79%

分子结构信息

SMILES: C(CCCCCCC/C=C\C=C\C(=O)CCCCC)(=O)O
InChI: InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)

描述信息

13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO. [HMDB]
13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE has been shown to stimulate cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO.

同义名列表

15 个代谢物同义名

(9Z,11E)-13-Oxooctadeca-9,11-dienoic acid; (9Z,11E)-13-Oxooctadeca-9,11-dienoate; 13-keto-9Z,11E-octadecadienoic acid; 13-oxo-9Z,11E-octadecadienoic acid; 13-keto-9,11,-octadecadienoic acid; 13-oxo-9,11-octadecadienoic acid; 13-Keto-9Z,11E-octadecadienoate; 13-oxooctadecadienoic acid; 13-OXO-ODE; 31385-09-8; 13-KetoODE; FA 18:3;O; 13-OxoODE; 13-Kodda; 13-KODE



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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

25 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

  • Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
  • 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]
  • Izabella Surowiec, Sandra Gouveia-Figueira, Judy Orikiiriza, Elisabeth Lindquist, Mari Bonde, Jimmy Magambo, Charles Muhinda, Sven Bergström, Johan Normark, Johan Trygg. The oxylipin and endocannabidome responses in acute phase Plasmodium falciparum malaria in children. Malaria journal. 2017 09; 16(1):358. doi: 10.1186/s12936-017-2001-y. [PMID: 28886714]
  • W Raphael, L Halbert, G A Contreras, L M Sordillo. Association between polyunsaturated fatty acid-derived oxylipid biosynthesis and leukocyte inflammatory marker expression in periparturient dairy cows. Journal of dairy science. 2014; 97(6):3615-25. doi: 10.3168/jds.2013-7656. [PMID: 24731638]
  • Danilo Meyer, Cornelia Herrfurth, Florian Brodhun, Ivo Feussner. Degradation of lipoxygenase-derived oxylipins by glyoxysomes from sunflower and cucumber cotyledons. BMC plant biology. 2013 Nov; 13(?):177. doi: 10.1186/1471-2229-13-177. [PMID: 24207097]
  • Zhi-Xin Yuan, Stanley I Rapoport, Steven J Soldin, Alan T Remaley, Ameer Y Taha, Matthew Kellom, Jianghong Gu, Maureen Sampson, Christopher E Ramsden. Identification and profiling of targeted oxidized linoleic acid metabolites in rat plasma by quadrupole time-of-flight mass spectrometry. Biomedical chromatography : BMC. 2013 Apr; 27(4):422-32. doi: 10.1002/bmc.2809. [PMID: 23037960]
  • Young-il Kim, Shizuka Hirai, Tsuyoshi Goto, Chie Ohyane, Haruya Takahashi, Taneaki Tsugane, Chiaki Konishi, Takashi Fujii, Shuji Inai, Yoko Iijima, Koh Aoki, Daisuke Shibata, Nobuyuki Takahashi, Teruo Kawada. Potent PPARα activator derived from tomato juice, 13-oxo-9,11-octadecadienoic acid, decreases plasma and hepatic triglyceride in obese diabetic mice. PloS one. 2012; 7(2):e31317. doi: 10.1371/journal.pone.0031317. [PMID: 22347463]
  • Audrey Combès, Idrissa Ndoye, Caroline Bance, Jérôme Bruzaud, Chakib Djediat, Joëlle Dupont, Bastien Nay, Soizic Prado. Chemical communication between the endophytic fungus Paraconiothyrium variabile and the phytopathogen Fusarium oxysporum. PloS one. 2012; 7(10):e47313. doi: 10.1371/journal.pone.0047313. [PMID: 23077591]
  • 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]
  • 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]
  • Rosario Zamora, Emerenciana Gallardo, Francisco J Hidalgo. Strecker degradation of phenylalanine initiated by 2,4-decadienal or methyl 13-oxooctadeca-9,11-dienoate in model systems. Journal of agricultural and food chemistry. 2007 Feb; 55(4):1308-14. doi: 10.1021/jf062838x. [PMID: 17300152]
  • 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]
  • Ernst H Oliw, Ulrike Garscha, Tomas Nilsson, Mirela Cristea. Payne rearrangement during analysis of epoxyalcohols of linoleic and alpha-linolenic acids by normal phase liquid chromatography with tandem mass spectrometry. Analytical biochemistry. 2006 Jul; 354(1):111-26. doi: 10.1016/j.ab.2006.04.010. [PMID: 16712763]
  • Igor Ivanov, Jan Saam, Hartmut Kuhn, Hermann-Georg Holzhütter. Dual role of oxygen during lipoxygenase reactions. The FEBS journal. 2005 May; 272(10):2523-35. doi: 10.1111/j.1742-4658.2005.04673.x. [PMID: 15885101]
  • Bernt Gerhardt, Kerstin Fischer, Thomas J Balkenhohl, Georg Pohnert, Hartmut Kühn, Claus Wasternack, Ivo Feussner. Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and beta-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes. Planta. 2005 Apr; 220(6):919-30. doi: 10.1007/s00425-004-1408-1. [PMID: 15526214]
  • Ivan R Chechetkin, Natalia V Medvedeva, Alexander N Grechkin. The novel pathway for ketodiene oxylipin biosynthesis in Jerusalem artichoke (Helianthus tuberosus) tubers. Biochimica et biophysica acta. 2004 Nov; 1686(1-2):7-14. doi: 10.1016/j.bbalip.2004.07.001. [PMID: 15522817]
  • I Podgorski, A W Bull. Energy-dependent export of the 13-oxooctadecadienoic acid-glutathione conjugate from HT-29 cells and plasma membrane vesicles. Biochimica et biophysica acta. 2001 Aug; 1533(1):55-65. doi: 10.1016/s1388-1981(01)00140-8. [PMID: 11514236]
  • H Iwase, T Takatori, M Nagao, H Nijima, K Iwadate, Y Matsuda, M Kobayashi. Formation of keto and hydroxy compounds of linoleic acid in submitochondrial particles of bovine heart. Free radical biology & medicine. 1998 Jun; 24(9):1492-503. doi: 10.1016/s0891-5849(98)00028-8. [PMID: 9641268]
  • H Iwase, K Sakurada, T Takatori, M Nagao, H Niijima, Y Matsuda, M Kobayashi. Calcium ions potentiate lipoxygenase activity of cytochrome c at the physiological pH. Biochemical and biophysical research communications. 1998 Feb; 243(2):485-91. doi: 10.1006/bbrc.1998.8126. [PMID: 9480835]
  • A W Bull, J C Bronstein. Production of unsaturated carbonyl compounds during metabolism of hydroperoxy fatty acids by colonic homogenates. Carcinogenesis. 1990 Oct; 11(10):1699-704. doi: 10.1093/carcin/11.10.1699. [PMID: 2208585]