Octadeca-9,12-dienal (BioDeep_00000175498)
Secondary id: BioDeep_00000332336
human metabolite blood metabolite
代谢物信息卡片
a Linoleic acid group
化学式: C18H32O (264.2453022)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 94.74%
分子结构信息
SMILES: CCCCCC=CCC=CCCCCCCCC=O
InChI: InChI=1S/C18H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h6-7,9-10,18H,2-5,8,11-17H2,1H3
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
- Ran Liang, Yin Liu, Li-Min Fu, Xi-Cheng Ai, Jian-Ping Zhang, Leif H Skibsted. Antioxidants and physical integrity of lipid bilayers under oxidative stress.
Journal of agricultural and food chemistry.
2012 Oct; 60(41):10331-6. doi:
10.1021/jf3030979. [PMID: 23016668] - Koji Morishita, Junichi Aiboshi, Tetsuyuki Kobayashi, Saori Mikami, Yuri Yokoyama, Kaori Ogawa, Hiroyuki Yokota, Yasuhiro Otomo. Lipidomics analysis of mesenteric lymph after trauma and hemorrhagic shock.
The journal of trauma and acute care surgery.
2012 Jun; 72(6):1541-7. doi:
10.1097/ta.0b013e318256df15. [PMID: 22695419] - Akira Tokumura, Satoshi Taira, Masaki Kikuchi, Toshihiko Tsutsumi, Yoshibumi Shimizu, Mitchell A Watsky. Lysophospholipids and lysophospholipase D in rabbit aqueous humor following corneal injury.
Prostaglandins & other lipid mediators.
2012 Mar; 97(3-4):83-9. doi:
10.1016/j.prostaglandins.2012.01.003. [PMID: 22281604] - Masaki Ino, Yoshibumi Shimizu, Tamotsu Tanaka, Akira Tokumura. Alterations of plasma levels of lysophosphatidic acid in response to fasting of rats.
Biological & pharmaceutical bulletin.
2012; 35(11):2059-63. doi:
10.1248/bpb.b12-00497. [PMID: 23123475] - Andreia C Turchetto-Zolet, Felipe S Maraschin, Guilherme L de Morais, Alexandro Cagliari, Cláudia M B Andrade, Marcia Margis-Pinheiro, Rogerio Margis. Evolutionary view of acyl-CoA diacylglycerol acyltransferase (DGAT), a key enzyme in neutral lipid biosynthesis.
BMC evolutionary biology.
2011 Sep; 11(?):263. doi:
10.1186/1471-2148-11-263. [PMID: 21933415] - Mika Adachi, Gou Horiuchi, Natsuki Ikematsu, Tamotsu Tanaka, Junji Terao, Kiyoshi Satouchi, Akira Tokumura. Intragastrically administered lysophosphatidic acids protect against gastric ulcer in rats under water-immersion restraint stress.
Digestive diseases and sciences.
2011 Aug; 56(8):2252-61. doi:
10.1007/s10620-011-1595-0. [PMID: 21298479] - Monika Riederer, Margarete Lechleitner, Andelko Hrzenjak, Harald Koefeler, Gernot Desoye, Akos Heinemann, Saša Frank. Endothelial lipase (EL) and EL-generated lysophosphatidylcholines promote IL-8 expression in endothelial cells.
Atherosclerosis.
2011 Feb; 214(2):338-44. doi:
10.1016/j.atherosclerosis.2010.11.007. [PMID: 21130993] - Frederique K H Breuers, Andrea Bräutigam, Andreas P M Weber. The Plastid Outer Envelope - A Highly Dynamic Interface between Plastid and Cytoplasm.
Frontiers in plant science.
2011; 2(?):97. doi:
10.3389/fpls.2011.00097. [PMID: 22629266] - Hae Jin Kim, Sung Han Ok, Sung Chul Bahn, Juno Jang, Sung Aeong Oh, Soon Ki Park, David Twell, Stephen Beungtae Ryu, Jeong Sheop Shin. Endoplasmic reticulum- and Golgi-localized phospholipase A2 plays critical roles in Arabidopsis pollen development and germination.
The Plant cell.
2011 Jan; 23(1):94-110. doi:
10.1105/tpc.110.074799. [PMID: 21278126] - Maike Rudolph, Armin Schlereth, Martina Körner, Kirstin Feussner, Ekkehardt Berndt, Michael Melzer, Ellen Hornung, Ivo Feussner. The lipoxygenase-dependent oxygenation of lipid body membranes is promoted by a patatin-type phospholipase in cucumber cotyledons.
Journal of experimental botany.
2011 Jan; 62(2):749-60. doi:
10.1093/jxb/erq310. [PMID: 21081663] - Rakesh P Prajapati, Manisha Kalariya, Sachin K Parmar, Navin R Sheth. Phytochemical and pharmacological review of Lagenaria sicereria.
Journal of Ayurveda and integrative medicine.
2010 Oct; 1(4):266-72. doi:
10.4103/0975-9476.74431. [PMID: 21731373] - Brenda J Blacklock, Brian E Scheffler, Michael R Shepard, Naomi Jayasuriya, Robert E Minto. Functional diversity in fungal fatty acid synthesis: the first acetylenase from the Pacific golden chanterelle, Cantharellus formosus.
The Journal of biological chemistry.
2010 Sep; 285(37):28442-9. doi:
10.1074/jbc.m110.151498. [PMID: 20606235] - Nathan Mellor, Frances Bligh, Ian Chandler, Charlie Hodgman. Reduction of off-flavor generation in soybean homogenates: a mathematical model.
Journal of food science.
2010 Sep; 75(7):R131-8. doi:
10.1111/j.1750-3841.2010.01733.x. [PMID: 21535565] - Junhwan Kim, Myriam E Rodriguez, Nancy L Oleinick, Vernon E Anderson. Photo-oxidation of cardiolipin and cytochrome c with bilayer-embedded Pc 4.
Free radical biology & medicine.
2010 Sep; 49(5):718-25. doi:
10.1016/j.freeradbiomed.2010.05.014. [PMID: 20510355] - Dimitris Anagnostopoulos, Carmelina Rakiec, Jodi Wood, Lakshmipathi Pandarinathan, Nikolai Zvonok, Alexandros Makriyannis, Athanasia Siafaka-Kapadai. Identification of endocannabinoids and related N-acylethanolamines in tetrahymena. A new class of compounds for Tetrahymena.
Protist.
2010 Jul; 161(3):452-65. doi:
10.1016/j.protis.2009.12.004. [PMID: 20096629] - Anna M Bakowska-Barczak, Andreas Schieber, Paul Kolodziejczyk. Characterization of Canadian black currant (Ribes nigrum L.) seed oils and residues.
Journal of agricultural and food chemistry.
2009 Dec; 57(24):11528-36. doi:
10.1021/jf902161k. [PMID: 19928765] - P Thomas Vernier, Zachary A Levine, Yu-Hsuan Wu, Vanessa Joubert, Matthew J Ziegler, Lluis M Mir, D Peter Tieleman. Electroporating fields target oxidatively damaged areas in the cell membrane.
PloS one.
2009 Nov; 4(11):e7966. doi:
10.1371/journal.pone.0007966. [PMID: 19956595] - Anna M Bakowska-Barczak, Andreas Schieber, Paul Kolodziejczyk. Characterization of Saskatoon berry ( Amelanchier alnifolia Nutt.) seed oil.
Journal of agricultural and food chemistry.
2009 Jun; 57(12):5401-6. doi:
10.1021/jf9006278. [PMID: 19449814] - Thierry Joët, Andréina Laffargue, Jordi Salmona, Sylvie Doulbeau, Frédéric Descroix, Benoît Bertrand, Alexandre de Kochko, Stéphane Dussert. Metabolic pathways in tropical dicotyledonous albuminous seeds: Coffea arabica as a case study.
The New phytologist.
2009; 182(1):146-162. doi:
10.1111/j.1469-8137.2008.02742.x. [PMID: 19207685] - Timothy J Cunningham, Lihua Yao, Angel Lucena. Product inhibition of secreted phospholipase A2 may explain lysophosphatidylcholines' unexpected therapeutic properties.
Journal of inflammation (London, England).
2008 Oct; 5(?):17. doi:
10.1186/1476-9255-5-17. [PMID: 18945345] - Long Shuang Huang, Mee Ree Kim, Dai-Eun Sok. Regulation of lipoxygenase activity by polyunsaturated lysophosphatidylcholines or their oxygenation derivatives.
Journal of agricultural and food chemistry.
2008 Sep; 56(17):7808-14. doi:
10.1021/jf801082x. [PMID: 18680379] - Suresh P Annangudi, Yijun Deng, Xiaorong Gu, Wujuan Zhang, John W Crabb, Robert G Salomon. Low-density lipoprotein has an enormous capacity to bind (E)-4-hydroxynon-2-enal (HNE): detection and characterization of lysyl and histidyl adducts containing multiple molecules of HNE.
Chemical research in toxicology.
2008 Jul; 21(7):1384-95. doi:
10.1021/tx8000303. [PMID: 18570390] - Xi Chen, Wujuan Zhang, James Laird, Stanley L Hazen, Robert G Salomon. Polyunsaturated phospholipids promote the oxidation and fragmentation of gamma-hydroxyalkenals: formation and reactions of oxidatively truncated ether phospholipids.
Journal of lipid research.
2008 Apr; 49(4):832-46. doi:
10.1194/jlr.m700598-jlr200. [PMID: 18165704] - Semra Turan, Ali Topcu, Ihsan Karabulut, Halil Vural, Ali Adnan Hayaloglu. Fatty acid, triacylglycerol, phytosterol, and tocopherol variations in kernel oil of Malatya apricots from Turkey.
Journal of agricultural and food chemistry.
2007 Dec; 55(26):10787-94. doi:
10.1021/jf071801p. [PMID: 18038980] - Takaaki Hayashi, Naomi Shishido, Kenji Nakayama, Akihiko Nunomura, Mark A Smith, George Perry, Masao Nakamura. Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-beta peptide.
Free radical biology & medicine.
2007 Dec; 43(11):1552-9. doi:
10.1016/j.freeradbiomed.2007.08.013. [PMID: 17964426] - Jiawei Chen, Lili Yang, Jason M Foulks, Andrew S Weyrich, Gopal K Marathe, Thomas M McIntyre. Intracellular PAF catabolism by PAF acetylhydrolase counteracts continual PAF synthesis.
Journal of lipid research.
2007 Nov; 48(11):2365-76. doi:
10.1194/jlr.m700325-jlr200. [PMID: 17693621] - Xi-Wen Liu, Dai-Eun Sok, Hong-Sun Yook, Cheon-Bae Sohn, Young-Jin Chung, Mee Ree Kim. Inhibition of lysophospholipase D activity by unsaturated lysophosphatidic acids or seed extracts containing 1-linoleoyl and 1-oleoyl lysophosphatidic acid.
Journal of agricultural and food chemistry.
2007 Oct; 55(21):8717-22. doi:
10.1021/jf071080u. [PMID: 17887800] - Cesarettin Alasalvar, Joana S Amaral, Fereidoon Shahidi. Functional lipid characteristics of Turkish Tombul hazelnut (Corylus avellana L.).
Journal of agricultural and food chemistry.
2006 Dec; 54(26):10177-83. doi:
10.1021/jf061702w. [PMID: 17177557] - Lucy Malinina, Margarita L Malakhova, Alex T Kanack, Min Lu, Ruben Abagyan, Rhoderick E Brown, Dinshaw J Patel. The liganding of glycolipid transfer protein is controlled by glycolipid acyl structure.
PLoS biology.
2006 Nov; 4(11):e362. doi:
10.1371/journal.pbio.0040362. [PMID: 17105344] - Saame Raza Shaikh, Vadim Cherezov, Martin Caffrey, Smita P Soni, Daniel LoCascio, William Stillwell, Stephen R Wassall. Molecular organization of cholesterol in unsaturated phosphatidylethanolamines: X-ray diffraction and solid state 2H NMR reveal differences with phosphatidylcholines.
Journal of the American Chemical Society.
2006 Apr; 128(16):5375-83. doi:
10.1021/ja057949b. [PMID: 16620109] - Mingjiang Sun, Silvia C Finnemann, Maria Febbraio, Lian Shan, Suresh P Annangudi, Eugene A Podrez, George Hoppe, Ruth Darrow, Daniel T Organisciak, Robert G Salomon, Roy L Silverstein, Stanley L Hazen. Light-induced oxidation of photoreceptor outer segment phospholipids generates ligands for CD36-mediated phagocytosis by retinal pigment epithelium: a potential mechanism for modulating outer segment phagocytosis under oxidant stress conditions.
The Journal of biological chemistry.
2006 Feb; 281(7):4222-30. doi:
10.1074/jbc.m509769200. [PMID: 16354659] - W Pruzanski, L Lambeau, M Lazdunsky, W Cho, J Kopilov, A Kuksis. Differential hydrolysis of molecular species of lipoprotein phosphatidylcholine by groups IIA, V and X secretory phospholipases A2.
Biochimica et biophysica acta.
2005 Sep; 1736(1):38-50. doi:
10.1016/j.bbalip.2005.07.005. [PMID: 16122976] - Marja T Hyvönen, Petri T Kovanen. Molecular dynamics simulations of unsaturated lipid bilayers: effects of varying the numbers of double bonds.
European biophysics journal : EBJ.
2005 Jun; 34(4):294-305. doi:
10.1007/s00249-004-0455-7. [PMID: 15688184] - Hideaki Matsuda, Masashi Tokunaga, Hiroyasu Iwahashi, Shunsuke Naruto, Hideki Yagi, Takashi Masuko, Michinori Kubo. Studies on palauan medicinal herbs. II. Activation of mouse macrophages RAW 264.7 by Ongael, leaves of Phaleria cumingii (Meisn.) F. Vill. and its acylglucosylsterols.
Biological & pharmaceutical bulletin.
2005 May; 28(5):929-33. doi:
10.1248/bpb.28.929. [PMID: 15863910] - Joana S Amaral, Sara C Cunha, M Rui Alves, José A Pereira, Rosa M Seabra, Beatriz P P Oliveira. Triacylglycerol composition of walnut (Juglans regia L.) cultivars: characterization by HPLC-ELSD and chemometrics.
Journal of agricultural and food chemistry.
2004 Dec; 52(26):7964-9. doi:
10.1021/jf048918n. [PMID: 15612783] - A Reis, P Domingues, A J V Ferrer-Correia, M R M Domingues. Tandem mass spectrometry of intact oxidation products of diacylphosphatidylcholines: evidence for the occurrence of the oxidation of the phosphocholine head and differentiation of isomers.
Journal of mass spectrometry : JMS.
2004 Dec; 39(12):1513-22. doi:
10.1002/jms.751. [PMID: 15578637] - Darwin W Reed, Devin R Polichuk, Peter H Buist, Stephen J Ambrose, Robert J Sasata, Christopher K Savile, Andrew R S Ross, Patrick S Covello. Mechanistic study of an improbable reaction: alkene dehydrogenation by the delta12 acetylenase of Crepis alpina.
Journal of the American Chemical Society.
2003 Sep; 125(35):10635-40. doi:
10.1021/ja036489o. [PMID: 12940747] - Darwin W Reed, Christopher K Savile, Xiao Qiu, Peter H Buist, Patrick S Covello. Mechanism of 1,4-dehydrogenation catalyzed by a fatty acid (1,4)-desaturase of Calendula officinalis.
European journal of biochemistry.
2002 Oct; 269(20):5024-9. doi:
10.1046/j.1432-1033.2002.03209.x. [PMID: 12383261] - Anca D Petrescu, Rachel Hertz, Jacob Bar-Tana, Friedhelm Schroeder, Ann B Kier. Ligand specificity and conformational dependence of the hepatic nuclear factor-4alpha (HNF-4alpha ).
The Journal of biological chemistry.
2002 Jul; 277(27):23988-99. doi:
10.1074/jbc.m201241200. [PMID: 11940586] - C Schwenger-Erger, W Barz, N Weber. Fatty acid alteration of plastidic and extra-plastidic membrane lipids in metribuzin-resistant photoautotrophic Chenopodium rubrum cells as compared to wild-type cells.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2001 Nov; 56(11-12):1047-56. doi:
10.1515/znc-2001-11-1223. [PMID: 11837657] - S Sakuma, Y Fujimoto, Y Katoh, A Kitao, T Fujita. The effects of fatty acyl CoA esters on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes.
Prostaglandins, leukotrienes, and essential fatty acids.
2001 Jan; 64(1):61-5. doi:
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