4-Oxohexanal (BioDeep_00000174494)
human metabolite blood metabolite
代谢物信息卡片
4-Oxohexanal
化学式: C6H10O2 (114.068076)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 75%
分子结构信息
SMILES: CCC(=O)CCC=O
InChI: InChI=1S/C6H10O2/c1-2-6(8)4-3-5-7/h5H,2-4H2,1H3
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
- Bingnan Han, Michael Hare, Samanthi Wickramasekara, Yi Fang, Claudia S Maier. A comparative 'bottom up' proteomics strategy for the site-specific identification and quantification of protein modifications by electrophilic lipids.
Journal of proteomics.
2012 Oct; 75(18):5724-33. doi:
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Journal of lipid research.
2012 Oct; 53(10):2069-2080. doi:
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The British journal of nutrition.
2012 Jul; 108(2):315-26. doi:
10.1017/s0007114511005484. [PMID: 22136711] - Melissa A Bradley, Shuling Xiong-Fister, William R Markesbery, Mark A Lovell. Elevated 4-hydroxyhexenal in Alzheimer's disease (AD) progression.
Neurobiology of aging.
2012 Jun; 33(6):1034-44. doi:
10.1016/j.neurobiolaging.2010.08.016. [PMID: 20965613] - Noah M Walton, Rick Shin, Katsunori Tajinda, Carrie L Heusner, Jeffrey H Kogan, Shinichi Miyake, Qian Chen, Kouichi Tamura, Mitsuyuki Matsumoto. Adult neurogenesis transiently generates oxidative stress.
PloS one.
2012; 7(4):e35264. doi:
10.1371/journal.pone.0035264. [PMID: 22558133] - Emin Ozbek. Induction of oxidative stress in kidney.
International journal of nephrology.
2012; 2012(?):465897. doi:
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Experimental diabetes research.
2012; 2012(?):703538. doi:
10.1155/2012/703538. [PMID: 22110477] - Mark A Lovell, Melissa A Bradley, Shuling X Fister. 4-Hydroxyhexenal (HHE) impairs glutamate transport in astrocyte cultures.
Journal of Alzheimer's disease : JAD.
2012; 32(1):139-46. doi:
10.3233/jad-2012-120409. [PMID: 22766736] - Niyazi Acar, Olivier Berdeaux, Stéphane Grégoire, Stéphanie Cabaret, Lucy Martine, Philippe Gain, Gilles Thuret, Catherine P Creuzot-Garcher, Alain M Bron, Lionel Bretillon. Lipid composition of the human eye: are red blood cells a good mirror of retinal and optic nerve fatty acids?.
PloS one.
2012; 7(4):e35102. doi:
10.1371/journal.pone.0035102. [PMID: 22496896] - Eşref Demir, Bülent Kaya, Carolina Soriano, Amadeu Creus, Ricard Marcos. Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay.
Mutation research.
2011 Dec; 726(2):98-103. doi:
10.1016/j.mrgentox.2011.07.001. [PMID: 21763450] - Eun Hui Bae, Sunghee Cho, Soo Yeon Joo, Seong Kwon Ma, Suhn Hee Kim, Jongun Lee, Soo Wan Kim. 4-Hydroxy-2-hexenal-induced apoptosis in human renal proximal tubular epithelial cells.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2011 Dec; 26(12):3866-73. doi:
10.1093/ndt/gfr386. [PMID: 21771752] - Rafael Medina-Navarro, Renato Nieto-Aguilar, Cleto Alvares-Aguilar. Protein conjugated with aldehydes derived from lipid peroxidation as an independent parameter of the carbonyl stress in the kidney damage.
Lipids in health and disease.
2011 Nov; 10(?):201. doi:
10.1186/1476-511x-10-201. [PMID: 22059738] - Juan D Chavez, Jianyong Wu, William Bisson, Claudia S Maier. Site-specific proteomic analysis of lipoxidation adducts in cardiac mitochondria reveals chemical diversity of 2-alkenal adduction.
Journal of proteomics.
2011 Oct; 74(11):2417-29. doi:
10.1016/j.jprot.2011.03.031. [PMID: 21513823] - Nicolas J Pillon, Roxane E Vella, Laurent Souleere, Michel Becchi, Michel Lagarde, Christophe O Soulage. Structural and functional changes in human insulin induced by the lipid peroxidation byproducts 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal.
Chemical research in toxicology.
2011 May; 24(5):752-62. doi:
10.1021/tx200084d. [PMID: 21462967] - Jean-François Lesgards, Cyrielle Gauthier, Juan Iovanna, Nicolas Vidal, Alain Dolla, Pierre Stocker. Effect of reactive oxygen and carbonyl species on crucial cellular antioxidant enzymes.
Chemico-biological interactions.
2011 Mar; 190(1):28-34. doi:
10.1016/j.cbi.2010.12.028. [PMID: 21216240] - Sergio Porté, Agrin Moeini, Irene Reche, Naeem Shafqat, Udo Oppermann, Jaume Farrés, Xavier Parés. Kinetic and structural evidence of the alkenal/one reductase specificity of human ζ-crystallin.
Cellular and molecular life sciences : CMLS.
2011 Mar; 68(6):1065-77. doi:
10.1007/s00018-010-0508-2. [PMID: 20835842] - Yukihiro Tsuchiya, Go Okada, Shigeki Kobayashi, Toshiyuki Chikuma, Hiroshi Hojo. 4-hydroxy-2-nonenal-modified glyceraldehyde-3-phosphate dehydrogenase is degraded by cathepsin G in rat neutrophils.
Oxidative medicine and cellular longevity.
2011; 2011(?):213686. doi:
10.1155/2011/213686. [PMID: 21904640] - Simon Wan Chan, Peter C Dedon. The biological and metabolic fates of endogenous DNA damage products.
Journal of nucleic acids.
2010 Dec; 2010(?):929047. doi:
10.4061/2010/929047. [PMID: 21209721] - Phaik Har Yong, Hongliang Zong, Reinhold J Medina, G Astrid Limb, Koji Uchida, Alan W Stitt, Tim M Curtis. Evidence supporting a role for N-(3-formyl-3,4-dehydropiperidino)lysine accumulation in Müller glia dysfunction and death in diabetic retinopathy.
Molecular vision.
2010 Dec; 16(?):2524-38. doi:
NULL. [PMID: 21151599] - Yael Riahi, Guy Cohen, Ofer Shamni, Shlomo Sasson. Signaling and cytotoxic functions of 4-hydroxyalkenals.
American journal of physiology. Endocrinology and metabolism.
2010 Dec; 299(6):E879-86. doi:
10.1152/ajpendo.00508.2010. [PMID: 20858748] - Atsushi Ishikado, Yoshihiko Nishio, Katsutaro Morino, Satoshi Ugi, Hajime Kondo, Taketoshi Makino, Atsunori Kashiwagi, Hiroshi Maegawa. Low concentration of 4-hydroxy hexenal increases heme oxygenase-1 expression through activation of Nrf2 and antioxidative activity in vascular endothelial cells.
Biochemical and biophysical research communications.
2010 Nov; 402(1):99-104. doi:
10.1016/j.bbrc.2010.09.124. [PMID: 20920477] - Nicolas J Pillon, Laurent Soulère, Roxane E Vella, Marine Croze, Bertrand R Caré, Hedi A Soula, Alain Doutheau, Michel Lagarde, Christophe O Soulage. Quantitative structure-activity relationship for 4-hydroxy-2-alkenal induced cytotoxicity in L6 muscle cells.
Chemico-biological interactions.
2010 Oct; 188(1):171-80. doi:
10.1016/j.cbi.2010.06.015. [PMID: 20619253] - Eric K Long, Matthew J Picklo. Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE...
Free radical biology & medicine.
2010 Jul; 49(1):1-8. doi:
10.1016/j.freeradbiomed.2010.03.015. [PMID: 20353821] - Eric K Long, Thad A Rosenberger, Matthew J Picklo. Ethanol withdrawal increases glutathione adducts of 4-hydroxy-2-hexenal but not 4-hydroxyl-2-nonenal in the rat cerebral cortex.
Free radical biology & medicine.
2010 Feb; 48(3):384-90. doi:
10.1016/j.freeradbiomed.2009.10.048. [PMID: 19878718] - Catherine Calzada, Romain Colas, Nicolas Guillot, Michel Guichardant, Martine Laville, Evelyne Véricel, Michel Lagarde. Subgram daily supplementation with docosahexaenoic acid protects low-density lipoproteins from oxidation in healthy men.
Atherosclerosis.
2010 Feb; 208(2):467-72. doi:
10.1016/j.atherosclerosis.2009.07.049. [PMID: 19717153] - Satoru Sakuma, Hiromi Sumi, Tetsuya Kohda, Yukio Arakawa, Yohko Fujimoto. Effects of Lipid Peroxidation-Derived Products on the Growth of Human Colorectal Cancer Cell Line HT-29.
Journal of clinical biochemistry and nutrition.
2009 Sep; 45(2):171-7. doi:
10.3164/jcbn.09-09. [PMID: 19794925] - T Shcheglova, S P Makker, A Tramontano. Covalent binding antibodies suppress advanced glycation: on the innate tier of adaptive immunity.
Acta naturae.
2009 Jul; 1(2):66-72. doi:
10.32607/20758251-2009-1-2-66-72. [PMID: 22649604] - Masaki Tanito, Richard S Brush, Michael H Elliott, Lea D Wicker, Kimberly R Henry, Robert E Anderson. High levels of retinal membrane docosahexaenoic acid increase susceptibility to stress-induced degeneration.
Journal of lipid research.
2009 May; 50(5):807-19. doi:
10.1194/jlr.m800170-jlr200. [PMID: 19023138] - Angel Catalá. Lipid peroxidation of membrane phospholipids generates hydroxy-alkenals and oxidized phospholipids active in physiological and/or pathological conditions.
Chemistry and physics of lipids.
2009 Jan; 157(1):1-11. doi:
10.1016/j.chemphyslip.2008.09.004. [PMID: 18977338] - Marie-Caroline Michalski, Catherine Calzada, Asami Makino, Sabine Michaud, Michel Guichardant. Oxidation products of polyunsaturated fatty acids in infant formulas compared to human milk--a preliminary study.
Molecular nutrition & food research.
2008 Dec; 52(12):1478-85. doi:
10.1002/mnfr.200700451. [PMID: 18792926] - Tadashi Sakai, Tetsuya Akiyama, Ai Ogura, Chie Kawano. The effects of NaCl on lipid peroxidation-derived aldehyde, 4-hydroxy-2-hexenal formation in boiled yellowtail meat.
Bioscience, biotechnology, and biochemistry.
2008 Sep; 72(9):2441-3. doi:
10.1271/bbb.80196. [PMID: 18776665] - Xuebo Liu, Takahiro Shibata, Shinsuke Hisaka, Yoshichika Kawai, Toshihiko Osawa. DHA Hydroperoxides as a Potential Inducer of Neuronal Cell Death: a Mitochondrial Dysfunction-Mediated Pathway.
Journal of clinical biochemistry and nutrition.
2008 Jul; 43(1):26-33. doi:
10.3164/jcbn.2008040. [PMID: 18648656] - Eric K Long, Tonya C Murphy, Laura J Leiphon, John Watt, Jason D Morrow, Ginger L Milne, Jocelyn R H Howard, Matthew J Picklo. Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation.
Journal of neurochemistry.
2008 May; 105(3):714-24. doi:
10.1111/j.1471-4159.2007.05175.x. [PMID: 18194211] - David A Andersson, Clive Gentry, Sian Moss, Stuart Bevan. Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2008 Mar; 28(10):2485-94. doi:
10.1523/jneurosci.5369-07.2008. [PMID: 18322093] - María D Guillén, Encarnación Goicoechea. Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: a review.
Critical reviews in food science and nutrition.
2008 Feb; 48(2):119-36. doi:
10.1080/10408390601177613. [PMID: 18274968] - Naomi Fukuoka, Hitoshi Sugiyama, Tatsuyuki Inoue, Yoko Kikumoto, Kei-ichi Takiue, Hiroshi Morinaga, Kazushi Nakao, Yohei Maeshima, Masato Asanuma, Da-Hong Wang, Keiki Ogino, Noriyoshi Masuoka, Hirofumi Makino. Increased susceptibility to oxidant-mediated tissue injury and peritoneal fibrosis in acatalasemic mice.
American journal of nephrology.
2008; 28(4):661-8. doi:
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Journal of clinical biochemistry and nutrition.
2007 Nov; 41(3):184-90. doi:
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Journal of toxicology and environmental health. Part A.
2007 Jul; 70(13):1071-5. doi:
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Analytical chemistry.
2007 May; 79(9):3342-54. doi:
10.1021/ac062262a. [PMID: 17385840] - Masaki Tanito, Feng Li, Michael H Elliott, Mark Dittmar, Robert E Anderson. Protective effect of TEMPOL derivatives against light-induced retinal damage in rats.
Investigative ophthalmology & visual science.
2007 Apr; 48(4):1900-5. doi:
10.1167/iovs.06-1057. [PMID: 17389526] - Kent Doi, Koji Okamoto, Kousuke Negishi, Yoshifumi Suzuki, Akihide Nakao, Toshiro Fujita, Akiko Toda, Takehiko Yokomizo, Yoshihiro Kita, Yasuyuki Kihara, Satoshi Ishii, Takao Shimizu, Eisei Noiri. Attenuation of folic acid-induced renal inflammatory injury in platelet-activating factor receptor-deficient mice.
The American journal of pathology.
2006 May; 168(5):1413-24. doi:
10.2353/ajpath.2006.050634. [PMID: 16651609] - Tadashi Sakai, Shusaku Ohtsubo, Toshiyuki Minami, Makoto Terayama. Effect of bleeding on hemoglobin contents and lipid oxidation in the skipjack muscle.
Bioscience, biotechnology, and biochemistry.
2006 Apr; 70(4):1006-8. doi:
10.1271/bbb.70.1006. [PMID: 16636471] - Toshiya Saeki, Miho Ichiba, Naotada Tanabe, Masaru Ueki, Kinya Okamoto, Yoshiko Matsunaga, Keiko Hosho, Takamasa Kanbe, Hiroyuki Tsuchiya, Akihiro Kurimasa, Sadako Yamada, Yasuaki Hirooka, Ichiro Hisatome, Yukihiro Kishimoto, Takeaki Suou, Yoshikazu Murawaki, Hironaka Kawasaki, Junji Yodoi, Goshi Shiota. Expression of oxidative stress-related molecules in circulating leukocytes and urine in patients with chronic viral hepatitis.
Liver international : official journal of the International Association for the Study of the Liver.
2006 Mar; 26(2):157-65. doi:
10.1111/j.1478-3231.2005.01213.x. [PMID: 16448453] - Hitoshi Sugiyama, Mizuho Kobayashi, Da-Hong Wang, Reiko Sunami, Yohei Maeshima, Yasushi Yamasaki, Noriyoshi Masuoka, Shohei Kira, Hirofumi Makino. Telmisartan inhibits both oxidative stress and renal fibrosis after unilateral ureteral obstruction in acatalasemic mice.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2005 Dec; 20(12):2670-80. doi:
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Food additives and contaminants.
2005 Aug; 22(8):701-8. doi:
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Archives of biochemistry and biophysics.
2005 Jun; 438(2):217-22. doi:
10.1016/j.abb.2005.04.015. [PMID: 15907785] - Akira Kitase, Keisuke Hino, Takakazu Furutani, Michiari Okuda, Toshikazu Gondo, Isao Hidaka, Yuichi Hara, Yuhki Yamaguchi, Kiwamu Okita. In situ detection of oxidized n-3 polyunsaturated fatty acids in chronic hepatitis C: correlation with hepatic steatosis.
Journal of gastroenterology.
2005 Jun; 40(6):617-24. doi:
10.1007/s00535-005-1596-x. [PMID: 16007396] - S Choudhary, T Xiao, S Srivastava, W Zhang, L L Chan, L A Vergara, F J G M Van Kuijk, N H Ansari. Toxicity and detoxification of lipid-derived aldehydes in cultured retinal pigmented epithelial cells.
Toxicology and applied pharmacology.
2005 Apr; 204(2):122-34. doi:
10.1016/j.taap.2004.08.023. [PMID: 15808518] - Ye-Sun Lee, Rosemary C Wander. Reduced effect on apoptosis of 4-hydroxyhexenal and oxidized LDL enriched with n-3 fatty acids from postmenopausal women.
The Journal of nutritional biochemistry.
2005 Apr; 16(4):213-21. doi:
10.1016/j.jnutbio.2004.09.006. [PMID: 15808325] - M Corradi, P Pignatti, P Manini, R Andreoli, M Goldoni, M Poppa, G Moscato, B Balbi, A Mutti. Comparison between exhaled and sputum oxidative stress biomarkers in chronic airway inflammation.
The European respiratory journal.
2004 Dec; 24(6):1011-7. doi:
10.1183/09031936.04.00002404. [PMID: 15572547] - J Y Lee, J H Je, K J Jung, B P Yu, H Y Chung. Induction of endothelial iNOS by 4-hydroxyhexenal through NF-kappaB activation.
Free radical biology & medicine.
2004 Aug; 37(4):539-48. doi:
10.1016/j.freeradbiomed.2004.05.011. [PMID: 15256225] - Reiko Sunami, Hitoshi Sugiyama, Da-Hong Wang, Mizuho Kobayashi, Yohei Maeshima, Yasushi Yamasaki, Noriyoshi Masuoka, Norio Ogawa, Shohei Kira, Hirofumi Makino. Acatalasemia sensitizes renal tubular epithelial cells to apoptosis and exacerbates renal fibrosis after unilateral ureteral obstruction.
American journal of physiology. Renal physiology.
2004 Jun; 286(6):F1030-8. doi:
10.1152/ajprenal.00266.2003. [PMID: 14722014] - Kent Doi, Yoshifumi Suzuki, Akihide Nakao, Toshiro Fujita, Eisei Noiri. Radical scavenger edaravone developed for clinical use ameliorates ischemia/reperfusion injury in rat kidney.
Kidney international.
2004 May; 65(5):1714-23. doi:
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Journal of lipid research.
2004 Apr; 45(4):626-34. doi:
10.1194/jlr.m300376-jlr200. [PMID: 14729859] - Ji Young Lee, Jeong Hwan Je, Dae Hyun Kim, Sang Woon Chung, Yani Zou, Nam Deuk Kim, Mie Ae Yoo, Hyung Suck Baik, Byung Pal Yu, Hae Young Chung. Induction of endothelial apoptosis by 4-hydroxyhexenal.
European journal of biochemistry.
2004 Apr; 271(7):1339-47. doi:
10.1111/j.1432-1033.2004.04042.x. [PMID: 15030484] - M Guichardant, B Chantegrel, C Deshayes, A Doutheau, P Moliere, M Lagarde. Specific markers of lipid peroxidation issued from n-3 and n-6 fatty acids.
Biochemical Society transactions.
2004 Feb; 32(Pt 1):139-40. doi:
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Human & experimental toxicology.
2004 Feb; 23(2):101-5. doi:
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Journal of lipid research.
2003 May; 44(5):917-26. doi:
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Plant & cell physiology.
2002 Dec; 43(12):1445-55. doi:
10.1093/pcp/pcf187. [PMID: 12514241] - S Choudhary, W Zhang, F Zhou, G A Campbell, L L Chan, E B Thompson, N H Ansari. Cellular lipid peroxidation end-products induce apoptosis in human lens epithelial cells.
Free radical biology & medicine.
2002 Feb; 32(4):360-9. doi:
10.1016/s0891-5849(01)00810-3. [PMID: 11841926] - J J García, R J Reiter, M Karbownik, J R Calvo, G G Ortiz, D X Tan, E Martínez-Ballarín, D Acuña-Castroviejo. N-acetylserotonin suppresses hepatic microsomal membrane rigidity associated with lipid peroxidation.
European journal of pharmacology.
2001 Oct; 428(2):169-75. doi:
10.1016/s0014-2999(01)01342-5. [PMID: 11675033] - T Grune, K Krämer, P P Hoppe, W Siems. Enrichment of eggs with n-3 polyunsaturated fatty acids: effects of vitamin E supplementation.
Lipids.
2001 Aug; 36(8):833-8. doi:
10.1007/s11745-001-0792-7. [PMID: 11592735] - F Furukawa, A Nishikawa, K Kasahara, M Miyauchi, H Nakamura, H Y Son, K Uchida, M Hirose. Involvement of lipid peroxidation in spontaneous pancreatitis in WBN/Kob rats.
Pancreas.
2001 May; 22(4):427-30. doi:
10.1097/00006676-200105000-00014. [PMID: 11345145] - W Zhang, Q He, L L Chan, F Zhou, M El Naghy, E B Thompson, N H Ansari. Involvement of caspases in 4-hydroxy-alkenal-induced apoptosis in human leukemic cells.
Free radical biology & medicine.
2001 Mar; 30(6):699-706. doi:
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