4-Oxo-2-nonenal (BioDeep_00000026961)

   

human metabolite


代谢物信息卡片


(2E)-4-oxonon-2-enal

化学式: C9H14O2 (154.09937440000002)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC(=O)C=CC=O
InChI: InChI=1S/C9H14O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-8H,2-4,6H2,1H3/b7-5+

描述信息

This compound belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms.

同义名列表

4 个代谢物同义名

(2E)-4-oxonon-2-enal; 4-Oxo-2-nonenal; 4-oxonon-2-enal; ONE



数据库引用编号

8 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)

3 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

  • Rafael Pineda-Alemán, Camila Cabarcas-Herrera, Antistio Alviz-Amador, Rodrigo Galindo-Murillo, Humberto Pérez-Gonzalez, Erika Rodríguez-Cavallo, Darío Méndez-Cuadro. Molecular dynamics of structural effects of reactive carbonyl species derivate of lipid peroxidation on bovine serum albumin. Biochimica et biophysica acta. General subjects. 2024 Jun; 1868(6):130613. doi: 10.1016/j.bbagen.2024.130613. [PMID: 38593934]
  • Rafael Pineda-Alemán, Camila Cabarcas-Herrera, Antistio Alviz-Amador, Humberto Pérez-Gonzalez, Erika Rodríguez-Cavallo, Darío Méndez-Cuadro. Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations. Journal of visualized experiments : JoVE. 2024 Apr; ?(206):. doi: 10.3791/66605. [PMID: 38738901]
  • Tie Wang, Weijin Liu, Qidi Zhang, Jie Jiao, Zihao Wang, Ge Gao, Hui Yang. 4-Oxo-2-Nonenal- and Agitation-Induced Aggregates of α-Synuclein and Phosphorylated α-Synuclein with Distinct Biophysical Properties and Biomedical Applications. Cells. 2024 Apr; 13(9):. doi: 10.3390/cells13090739. [PMID: 38727274]
  • Camilla B Andersen, Astrid K Lausdahl, Janni Nielsen, Mathias P Clausen, Frans A A Mulder, Daniel E Otzen, Eva C Arnspang. 4-Oxo-2-nonenal-Induced α-Synuclein Oligomers Interact with Membranes in the Cell, Leading to Mitochondrial Fragmentation. Biochemistry. 2023 08; 62(16):2417-2425. doi: 10.1021/acs.biochem.3c00114. [PMID: 37487228]
  • Loren Klein, Dennis Phillips, Fanbin Kong, Brian Bowker, Anand Mohan. 4-Oxo-2-nonenal (4-ONE)-Induced Degradation of Bovine Skeletal Muscle Proteins. Journal of agricultural and food chemistry. 2022 Oct; 70(39):12641-12650. doi: 10.1021/acs.jafc.2c05550. [PMID: 36129340]
  • Jennifer S Strehse, Daniel Hoffmann, Nikolaos Protopapas, Hans-Jörg Martin, Edmund Maser. Carbonyl reduction of 4-oxonon-2-enal (4-ONE) by Sniffer from D. magna and D.pulex. Chemico-biological interactions. 2022 Feb; 354(?):109833. doi: 10.1016/j.cbi.2022.109833. [PMID: 35085582]
  • Camilla Andersen, Anne Louise Grønnemose, Jannik N Pedersen, Jan S Nowak, Gunna Christiansen, Janni Nielsen, Frans A A Mulder, Daniel Erik Otzen, Thomas J D Jørgensen. Lipid Peroxidation Products HNE and ONE Promote and Stabilize Alpha-Synuclein Oligomers by Chemical Modifications. Biochemistry. 2021 11; 60(47):3644-3658. doi: 10.1021/acs.biochem.1c00478. [PMID: 34730940]
  • Linda S May-Zhang, Valery Yermalitsky, John T Melchior, Jamie Morris, Keri A Tallman, Mark S Borja, Tiffany Pleasent, Venkataraman Amarnath, Wenliang Song, Patricia G Yancey, W Sean Davidson, MacRae F Linton, Sean S Davies. Modified sites and functional consequences of 4-oxo-2-nonenal adducts in HDL that are elevated in familial hypercholesterolemia. The Journal of biological chemistry. 2019 12; 294(50):19022-19033. doi: 10.1074/jbc.ra119.009424. [PMID: 31666337]
  • Seon Hwa Lee, Shuhei Fujioka, Ryo Takahashi, Tomoyuki Oe. Angiotensin II-Induced Oxidative Stress in Human Endothelial Cells: Modification of Cellular Molecules through Lipid Peroxidation. Chemical research in toxicology. 2019 07; 32(7):1412-1422. doi: 10.1021/acs.chemrestox.9b00110. [PMID: 31144504]
  • Francisco J Hidalgo, Isabel Aguilar, Rosario Zamora. Phenolic trapping of lipid oxidation products 4-oxo-2-alkenals. Food chemistry. 2018 Feb; 240(?):822-830. doi: 10.1016/j.foodchem.2017.08.027. [PMID: 28946347]
  • Rui Sun, Ling Fu, Keke Liu, Caiping Tian, Yong Yang, Keri A Tallman, Ned A Porter, Daniel C Liebler, Jing Yang. Chemoproteomics Reveals Chemical Diversity and Dynamics of 4-Oxo-2-nonenal Modifications in Cells. Molecular & cellular proteomics : MCP. 2017 10; 16(10):1789-1800. doi: 10.1074/mcp.ra117.000116. [PMID: 28814509]
  • Leire Almandoz-Gil, Hedvig Welander, Elisabet Ihse, Payam Emami Khoonsari, Sravani Musunuri, Christofer Lendel, Jessica Sigvardson, Mikael Karlsson, Martin Ingelsson, Kim Kultima, Joakim Bergström. Low molar excess of 4-oxo-2-nonenal and 4-hydroxy-2-nonenal promote oligomerization of alpha-synuclein through different pathways. Free radical biology & medicine. 2017 09; 110(?):421-431. doi: 10.1016/j.freeradbiomed.2017.07.004. [PMID: 28690195]
  • Eşref Demir, Ricard Marcos. Assessing the genotoxic effects of two lipid peroxidation products (4-oxo-2-nonenal and 4-hydroxy-hexenal) in haemocytes and midgut cells of Drosophila melanogaster larvae. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Jul; 105(?):1-7. doi: 10.1016/j.fct.2017.03.036. [PMID: 28343031]
  • Katarina Vazdar, Danijela Vojta, Davor Margetić, Mario Vazdar. Reaction Mechanism of Covalent Modification of Phosphatidylethanolamine Lipids by Reactive Aldehydes 4-Hydroxy-2-nonenal and 4-Oxo-2-nonenal. Chemical research in toxicology. 2017 03; 30(3):840-850. doi: 10.1021/acs.chemrestox.6b00443. [PMID: 28222263]
  • Jeannie M Camarillo, Jody C Ullery, Kristie L Rose, Lawrence J Marnett. Electrophilic Modification of PKM2 by 4-Hydroxynonenal and 4-Oxononenal Results in Protein Cross-Linking and Kinase Inhibition. Chemical research in toxicology. 2017 02; 30(2):635-641. doi: 10.1021/acs.chemrestox.6b00374. [PMID: 27978618]
  • Lars Zimmermann, Rudolf Moldzio, Katarina Vazdar, Christopher Krewenka, Elena E Pohl. Nutrient deprivation in neuroblastoma cells alters 4-hydroxynonenal-induced stress response. Oncotarget. 2017 Jan; 8(5):8173-8188. doi: 10.18632/oncotarget.14132. [PMID: 28030790]
  • Yiwen Cui, Xin Li, Jianwei Lin, Quan Hao, Xiang David Li. Histone Ketoamide Adduction by 4-Oxo-2-nonenal Is a Reversible Posttranslational Modification Regulated by Sirt2. ACS chemical biology. 2017 01; 12(1):47-51. doi: 10.1021/acschembio.6b00713. [PMID: 28103679]
  • Toshiyuki Matsunaga, Ayaka Suzuki, Chihiro Kezuka, Naoko Okumura, Kazuhiro Iguchi, Ikuo Inoue, Midori Soda, Satoshi Endo, Ossama El-Kabbani, Akira Hara, Akira Ikari. Aldo-keto reductase 1B10 promotes development of cisplatin resistance in gastrointestinal cancer cells through down-regulating peroxisome proliferator-activated receptor-γ-dependent mechanism. Chemico-biological interactions. 2016 Aug; 256(?):142-53. doi: 10.1016/j.cbi.2016.07.008. [PMID: 27417252]
  • Olga Jovanovic, Alina A Pashkovskaya, Andrea Annibal, Mario Vazdar, Nadine Burchardt, Anna Sansone, Lars Gille, Maria Fedorova, Carla Ferreri, Elena E Pohl. The molecular mechanism behind reactive aldehyde action on transmembrane translocations of proton and potassium ions. Free radical biology & medicine. 2015 Dec; 89(?):1067-76. doi: 10.1016/j.freeradbiomed.2015.10.422. [PMID: 26520807]
  • Venkataraman Amarnath, Kalyani Amarnath. Scavenging 4-Oxo-2-nonenal. Chemical research in toxicology. 2015 Oct; 28(10):1888-90. doi: 10.1021/acs.chemrestox.5b00301. [PMID: 26355561]
  • Ryo Takahashi, Takaaki Goto, Tomoyuki Oe, Seon Hwa Lee. Angiotensin II modification by decomposition products of linoleic acid-derived lipid hydroperoxide. Chemico-biological interactions. 2015 Sep; 239(?):87-99. doi: 10.1016/j.cbi.2015.06.029. [PMID: 26111765]
  • Mahavir Singh, Aniruddh Kapoor, Aruni Bhatnagar. Oxidative and reductive metabolism of lipid-peroxidation derived carbonyls. Chemico-biological interactions. 2015 Jun; 234(?):261-73. doi: 10.1016/j.cbi.2014.12.028. [PMID: 25559856]
  • Christopher D Aluise, Jeannie M Camarillo, Yuki Shimozu, James J Galligan, Kristie L Rose, Keri A Tallman, Lawrence J Marnett. Site-specific, intramolecular cross-linking of Pin1 active site residues by the lipid electrophile 4-oxo-2-nonenal. Chemical research in toxicology. 2015 Apr; 28(4):817-27. doi: 10.1021/acs.chemrestox.5b00038. [PMID: 25739016]
  • Jan Hintzpeter, Hans-Joerg Martin, Edmund Maser. Reduction of lipid peroxidation products and advanced glycation end-product precursors by cyanobacterial aldo-keto reductase AKR3G1—a founding member of the AKR3G subfamily. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2015 Jan; 29(1):263-73. doi: 10.1096/fj.14-258327. [PMID: 25376835]
  • James J Galligan, Kristie L Rose, William N Beavers, Salisha Hill, Keri A Tallman, William P Tansey, Lawrence J Marnett. Stable histone adduction by 4-oxo-2-nonenal: a potential link between oxidative stress and epigenetics. Journal of the American Chemical Society. 2014 Aug; 136(34):11864-6. doi: 10.1021/ja503604t. [PMID: 25099620]
  • James J Galligan, Kristofer S Fritz, Donald S Backos, Colin T Shearn, Rebecca L Smathers, Hua Jiang, Kenneth N MacLean, Philip R Reigan, Dennis R Petersen. Oxidative stress-mediated aldehyde adduction of GRP78 in a mouse model of alcoholic liver disease: functional independence of ATPase activity and chaperone function. Free radical biology & medicine. 2014 Aug; 73(?):411-20. doi: 10.1016/j.freeradbiomed.2014.06.002. [PMID: 24924946]
  • Laura Bertoletti, Luca Regazzoni, Alessandra Altomare, Raffaella Colombo, Mara Colzani, Giulio Vistoli, Loredana Marchese, Marina Carini, Ersilia De Lorenzi, Giancarlo Aldini. Advanced glycation end products of beta2-microglobulin in uremic patients as determined by high resolution mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Mar; 91(?):193-201. doi: 10.1016/j.jpba.2013.12.021. [PMID: 24469019]
  • Simona G Codreanu, Jody C Ullery, Jing Zhu, Keri A Tallman, William N Beavers, Ned A Porter, Lawrence J Marnett, Bing Zhang, Daniel C Liebler. Alkylation damage by lipid electrophiles targets functional protein systems. Molecular & cellular proteomics : MCP. 2014 Mar; 13(3):849-59. doi: 10.1074/mcp.m113.032953. [PMID: 24429493]
  • Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures. Food chemistry. 2013 Dec; 141(4):4240-5. doi: 10.1016/j.foodchem.2013.06.036. [PMID: 23993611]
  • Satoshi Endo, Toshiyuki Matsunaga, Atsuko Matsumoto, Yuki Arai, Satoshi Ohno, Ossama El-Kabbani, Kazuo Tajima, Yasuo Bunai, Shigeru Yamano, Akira Hara, Yukio Kitade. Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D₂, and other endogenous and xenobiotic carbonyl compounds. Biochemical pharmacology. 2013 Nov; 86(9):1366-75. doi: 10.1016/j.bcp.2013.08.024. [PMID: 23994167]
  • Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Strecker-type degradation of phenylalanine initiated by 4-oxo-2-alkenals in comparison to that initiated by 2,4-alkadienals, 4,5-epoxy-2-alkenals, or 4-hydroxy-2-nonenal. Journal of agricultural and food chemistry. 2013 Oct; 61(43):10231-7. doi: 10.1021/jf305007y. [PMID: 23360317]
  • Kazuaki Kawai, Yuya Kawasaki, Yumiko Kubota, Tomoyuki Kimura, Ryuichi Sawa, Tomonari Matsuda, Hiroshi Kasai. Identification of octenal-related dA and dC adducts formed by reactions with a hemin-ω-6-fat peroxidation model system. Chemical research in toxicology. 2013 Oct; 26(10):1554-60. doi: 10.1021/tx400245a. [PMID: 24032558]
  • Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Comparative formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures. Food chemistry. 2013 May; 138(1):180-5. doi: 10.1016/j.foodchem.2012.09.116. [PMID: 23265474]
  • Eşref Demir, Fatma Turna, Bülent Kaya, Amadeu Creus, Ricard Marcos. Mutagenic/recombinogenic effects of four lipid peroxidation products in Drosophila. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Mar; 53(?):221-7. doi: 10.1016/j.fct.2012.11.053. [PMID: 23238235]
  • Satoshi Endo, Airi Fujimoto, Sho Kumada, Toshiyuki Matsunaga, Satoshi Ohno, Jun'ichi Mano, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Modulation of activity and inhibitor sensitivity of rabbit aldose reductase-like protein (AKR1B19) by oxidized glutathione and SH-reagents. Chemico-biological interactions. 2013 Feb; 202(1-3):146-52. doi: 10.1016/j.cbi.2012.11.026. [PMID: 23261715]
  • Seon Hwa Lee. [Oxidative stress-mediated chemical modifications to biomacromolecules: mechanism and implication of modifications to human skin keratins and angiotensin II]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2013; 133(10):1055-63. doi: 10.1248/yakushi.13-00176. [PMID: 24088349]
  • Miho Chikazawa, Natsuki Otaki, Takahiro Shibata, Takehiko Yasueda, Tsukasa Matsuda, Koji Uchida. An apoptosis-associated mammary protein deficiency leads to enhanced production of IgM antibodies against multiple damage-associated molecules. PloS one. 2013; 8(7):e68468. doi: 10.1371/journal.pone.0068468. [PMID: 23874637]
  • Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems. Food chemistry. 2012 Dec; 135(4):2569-74. doi: 10.1016/j.foodchem.2012.06.062. [PMID: 22980844]
  • Jessica M Curtis, Wendy S Hahn, Matthew D Stone, Jacob J Inda, David J Droullard, Jovan P Kuzmicic, Margaret A Donoghue, Eric K Long, Anibal G Armien, Sergio Lavandero, Edgar Arriaga, Timothy J Griffin, David A Bernlohr. Protein carbonylation and adipocyte mitochondrial function. The Journal of biological chemistry. 2012 Sep; 287(39):32967-80. doi: 10.1074/jbc.m112.400663. [PMID: 22822087]
  • Lilu Guo, Zhongyi Chen, Venkataraman Amarnath, Sean S Davies. Identification of novel bioactive aldehyde-modified phosphatidylethanolamines formed by lipid peroxidation. Free radical biology & medicine. 2012 Sep; 53(6):1226-38. doi: 10.1016/j.freeradbiomed.2012.07.077. [PMID: 22898174]
  • Rosario Zamora, Rosa M Delgado, Francisco J Hidalgo. Chemical conversion of phenylethylamine into phenylacetaldehyde by carbonyl-amine reactions in model systems. Journal of agricultural and food chemistry. 2012 May; 60(21):5491-6. doi: 10.1021/jf301258s. [PMID: 22578256]
  • James J Galligan, Rebecca L Smathers, Kristofer S Fritz, L E Epperson, Lawrence E Hunter, Dennis R Petersen. Protein carbonylation in a murine model for early alcoholic liver disease. Chemical research in toxicology. 2012 May; 25(5):1012-21. doi: 10.1021/tx300002q. [PMID: 22502949]
  • Qingling Li, Kristyen Tomcik, Shenghui Zhang, Michelle A Puchowicz, Guo-Fang Zhang. Dietary regulation of catabolic disposal of 4-hydroxynonenal analogs in rat liver. Free radical biology & medicine. 2012 Mar; 52(6):1043-53. doi: 10.1016/j.freeradbiomed.2011.12.022. [PMID: 22245097]
  • Xiaodong Gu, Robert G Salomon. Fragmentation of a linoleate-derived γ-hydroperoxy-α,β-unsaturated epoxide to γ-hydroxy- and γ-oxo-alkenals involves a unique pseudo-symmetrical diepoxycarbinyl radical. Free radical biology & medicine. 2012 Feb; 52(3):601-606. doi: 10.1016/j.freeradbiomed.2011.11.013. [PMID: 22155057]
  • Sung Young Kim, Sang Chul Park. Physiological antioxidative network of the bilirubin system in aging and age-related diseases. Frontiers in pharmacology. 2012; 3(?):45. doi: 10.3389/fphar.2012.00045. [PMID: 22457648]
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  • Rebecca L Smathers, Kristofer S Fritz, James J Galligan, Colin T Shearn, Philip Reigan, Michael J Marks, Dennis R Petersen. Characterization of 4-HNE modified L-FABP reveals alterations in structural and functional dynamics. PloS one. 2012; 7(6):e38459. doi: 10.1371/journal.pone.0038459. [PMID: 22701647]
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