Cyclopentanone (BioDeep_00000004447)
Secondary id: BioDeep_00000413316
human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019
代谢物信息卡片
3-Acetyl-6-methyl-pyran-2,4(3H)-dione
化学式: C5H8O (84.0575118)
中文名称: 环戊酮
谱图信息:
最多检出来源 Homo sapiens(feces) 0.05%
分子结构信息
SMILES: C1CCC(=O)C1
InChI: InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
描述信息
Cyclopentanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Cyclopentanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, cyclopentanone is considered to be an oxygenated hydrocarbon lipid molecule. Cyclopentanone is a cyclic ketone, structurally similar to cyclopentane, consisting of a five-membered ring containing a ketone functional group. Cyclopentanone is a colorless liquid organic compound with a peppermint-like odor. Cyclopentanone is found in various foods, including potato and tomato, and cooked foods, e.g. butter, meats, coffee, roasted peanut. Cyclopentanone is also used as a flavouring ingredient.
Found in various foods, including potato and tomato, and cooked foods, e.g. butter, meats, coffee, roasted peanut. Flavouring ingredient
同义名列表
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:16486
- KEGG: C00557
- PubChem: 8452
- HMDB: HMDB0031407
- Metlin: METLIN65520
- ChEMBL: CHEMBL18620
- Wikipedia: Cyclopentanone
- MetaCyc: CYCLOPENTANONE
- foodb: FDB003481
- chemspider: 8141
- CAS: 120-92-3
- PMhub: MS000016904
- PubChem: 3837
- PDB-CCD: MFW
- 3DMET: B00131
- NIKKAJI: J5.333C
- RefMet: Cyclopentanone
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-429
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
- 13443 - Coffea arabica: 10.1021/JF60160A010
- 9606 - Homo sapiens: -
- 103349 - Vitis rotundifolia: 10.1111/J.1365-2621.1984.TB13669.X
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
- Xiaohuan Yuan, Hongzhi Li, He Bai, Xiaojin Zhao, Chunlei Zhang, Haifeng Liu, Yufei Zhang, Binghai Zhao, Yan Wu, Jieting Liu, Qi Xiang, Biao Feng, Yanhui Chu, Yadong Huang. The 11β-hydroxysteroid dehydrogenase type 1 inhibitor protects against the insulin resistance and hepatic steatosis in db/db mice.
European journal of pharmacology.
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Current microbiology.
2016 Mar; 72(3):297-305. doi:
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Phytochemistry.
2015 Oct; 118(?):174-80. doi:
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2011 Jun; 30(6):1421-9. doi:
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Plant physiology.
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2011 Apr; 13(7):1864-7. doi:
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2011 Jan; 12(?):20. doi:
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2010 Dec; 16(48):14479-85. doi:
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Chinese medicine.
2008 Sep; 3(?):11. doi:
10.1186/1749-8546-3-11. [PMID: 18798984] - Erik S Musiek, Joshua D Brooks, Myungsoo Joo, Enrico Brunoldi, Alessio Porta, Giuseppe Zanoni, Giovanni Vidari, Timothy S Blackwell, Thomas J Montine, Ginger L Milne, BethAnn McLaughlin, Jason D Morrow. Electrophilic cyclopentenone neuroprostanes are anti-inflammatory mediators formed from the peroxidation of the omega-3 polyunsaturated fatty acid docosahexaenoic acid.
The Journal of biological chemistry.
2008 Jul; 283(29):19927-35. doi:
10.1074/jbc.m803625200. [PMID: 18490445] - Lucila Ludmila Paula Gutierrez, Alexandre Maslinkiewicz, Rui Curi, Paulo Ivo Homem de Bittencourt. Atherosclerosis: a redox-sensitive lipid imbalance suppressible by cyclopentenone prostaglandins.
Biochemical pharmacology.
2008 Jun; 75(12):2245-62. doi:
10.1016/j.bcp.2008.03.002. [PMID: 18440492] - 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] - Stefan Mueller, Beate Hilbert, Katharina Dueckershoff, Thomas Roitsch, Markus Krischke, Martin J Mueller, Susanne Berger. General detoxification and stress responses are mediated by oxidized lipids through TGA transcription factors in Arabidopsis.
The Plant cell.
2008 Mar; 20(3):768-85. doi:
10.1105/tpc.107.054809. [PMID: 18334669] - Eckhard Hofmann, Stephan Pollmann. Molecular mechanism of enzymatic allene oxide cyclization in plants.
Plant physiology and biochemistry : PPB.
2008 Mar; 46(3):302-8. doi:
10.1016/j.plaphy.2007.12.007. [PMID: 18272375] - Paul D Drew, Jihong Xu, Michael K Racke. PPAR-gamma: Therapeutic Potential for Multiple Sclerosis.
PPAR research.
2008; 2008(?):627463. doi:
10.1155/2008/627463. [PMID: 18604287] - Shinji Kume, Takashi Uzu, Keiji Isshiki, Daisuke Koya. Peroxisome proliferator-activated receptors in diabetic nephropathy.
PPAR research.
2008; 2008(?):879523. doi:
10.1155/2008/879523. [PMID: 19277201] - Alexander N Grechkin, Anna V Ogorodnikova, Oleg I Gnezdilov, Lucia S Mukhtarova. Detection of a pathway from linoleate to a novel cyclopentenone: cis-12-oxo-10-phytoenoic acid in sunflower roots.
Chembiochem : a European journal of chemical biology.
2007 Dec; 8(18):2275-80. doi:
10.1002/cbic.200700393. [PMID: 17957816] - Woo Jae Kim, Joon Hyun Kim, Sung Key Jang. Anti-inflammatory lipid mediator 15d-PGJ2 inhibits translation through inactivation of eIF4A.
The EMBO journal.
2007 Dec; 26(24):5020-32. doi:
10.1038/sj.emboj.7601920. [PMID: 18034160] - O Haworth, B D Levy. Endogenous lipid mediators in the resolution of airway inflammation.
The European respiratory journal.
2007 Nov; 30(5):980-92. doi:
10.1183/09031936.00005807. [PMID: 17978156] - Carole Lavigne, Alain R Thierry. Specific subcellular localization of siRNAs delivered by lipoplex in MCF-7 breast cancer cells.
Biochimie.
2007 Oct; 89(10):1245-51. doi:
10.1016/j.biochi.2007.05.002. [PMID: 17619075] - Gemma Olmos, Isabel Conde, Isabel Arenas, Luis Del Peso, Carmen Castellanos, Manuel O Landazuri, Javier Lucio-Cazana. Accumulation of hypoxia-inducible factor-1alpha through a novel electrophilic, thiol antioxidant-sensitive mechanism.
Cellular signalling.
2007 Oct; 19(10):2098-105. doi:
10.1016/j.cellsig.2007.06.004. [PMID: 17658243] - Enrico M Brunoldi, Giuseppe Zanoni, Giovanni Vidari, Soumya Sasi, Michael L Freeman, Ginger L Milne, Jason D Morrow. Cyclopentenone prostaglandin, 15-deoxy-Delta12,14-PGJ2, is metabolized by HepG2 cells via conjugation with glutathione.
Chemical research in toxicology.
2007 Oct; 20(10):1528-35. doi:
10.1021/tx700231a. [PMID: 17854155] - Erik S Musiek, Bethann McLaughlin, Jason D Morrow. Electrophilic cyclopentenone isoprostanes in neurodegeneration.
Journal of molecular neuroscience : MN.
2007 Sep; 33(1):80-6. doi:
10.1007/s12031-007-0042-3. [PMID: 17901550] - Natalia V Medvedeva, Lucia S Mukhtarova, Faina K Mukhitova, Alsu A Balandina, Shamil K Latypov, Alexander N Grechkin. Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate.
Chemistry and physics of lipids.
2007 Aug; 148(2):91-6. doi:
10.1016/j.chemphyslip.2007.04.010. [PMID: 17553477] - S A Sharifah Sakinah, S Tri Handayani, L P Azimahtol Hawariah. Zerumbone induced apoptosis in liver cancer cells via modulation of Bax/Bcl-2 ratio.
Cancer cell international.
2007 Apr; 7(?):4. doi:
10.1186/1475-2867-7-4. [PMID: 17407577] - Werner I Hagens, Adriana Mattos, Rick Greupink, Alie de Jager-Krikken, Catharina Reker-Smit, Annemiek van Loenen-Weemaes, I Annette S H Gouw, Klaas Poelstra, Leonie Beljaars. Targeting 15d-prostaglandin J2 to hepatic stellate cells: two options evaluated.
Pharmaceutical research.
2007 Mar; 24(3):566-74. doi:
10.1007/s11095-006-9175-2. [PMID: 17245650] - Francisco J Sánchez-Gómez, Javier Gayarre, M Isabel Avellano, Dolores Pérez-Sala. Direct evidence for the covalent modification of glutathione-S-transferase P1-1 by electrophilic prostaglandins: implications for enzyme inactivation and cell survival.
Archives of biochemistry and biophysics.
2007 Jan; 457(2):150-9. doi:
10.1016/j.abb.2006.10.032. [PMID: 17169324] - Shigeharu Ueki, Hikari Kato, Yoshiki Kobayashi, Wataru Ito, Tetsuya Adachi, Hiroyuki Nagase, Ken Ohta, Hiroyuki Kayaba, Junichi Chihara. Anti- and proinflammatory effects of 15-deoxy-delta-prostaglandin J2(15d-PGJ2) on human eosinophil functions.
International archives of allergy and immunology.
2007; 143 Suppl 1(?):15-22. doi:
10.1159/000101399. [PMID: 17541271] - Heather F Lakatos, Thomas H Thatcher, R Matthew Kottmann, Tatiana M Garcia, Richard P Phipps, Patricia J Sime. The Role of PPARs in Lung Fibrosis.
PPAR research.
2007; 2007(?):71323. doi:
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PPAR research.
2007; 2007(?):63745. doi:
10.1155/2007/63745. [PMID: 17710233] - Sung Mun Jung, H Ralph Schumacher, Hocheol Kim, Miyeon Kim, Seoung Hoon Lee, Frank Pessler. Reduction of urate crystal-induced inflammation by root extracts from traditional oriental medicinal plants: elevation of prostaglandin D2 levels.
Arthritis research & therapy.
2007; 9(4):R64. doi:
10.1186/ar2222. [PMID: 17612394] - Konstantinos Stamatakis, Dolores Pérez-Sala. Prostanoids with cyclopentenone structure as tools for the characterization of electrophilic lipid-protein interactomes.
Annals of the New York Academy of Sciences.
2006 Dec; 1091(?):548-70. doi:
10.1196/annals.1378.096. [PMID: 17341644] - Maëlle Carraz, Akino Jossang, Jean-François Franetich, Anthony Siau, Liliane Ciceron, Laurent Hannoun, Robert Sauerwein, François Frappier, Philippe Rasoanaivo, Georges Snounou, Dominique Mazier. A plant-derived morphinan as a novel lead compound active against malaria liver stages.
PLoS medicine.
2006 Dec; 3(12):e513. doi:
10.1371/journal.pmed.0030513. [PMID: 17194195] - Javier Gayarre, David Sánchez, Francisco J Sánchez-Gómez, María C Terrón, Oscar Llorca, Dolores Pérez-Sala. Addition of electrophilic lipids to actin alters filament structure.
Biochemical and biophysical research communications.
2006 Nov; 349(4):1387-93. doi:
10.1016/j.bbrc.2006.09.005. [PMID: 16979589] - Michael Stumpe, Cornelia Göbel, Kirill Demchenko, Manuela Hoffmann, Ralf B Klösgen, Katharina Pawlowski, Ivo Feussner. Identification of an allene oxide synthase (CYP74C) that leads to formation of alpha-ketols from 9-hydroperoxides of linoleic and linolenic acid in below-ground organs of potato.
The Plant journal : for cell and molecular biology.
2006 Sep; 47(6):883-96. doi:
10.1111/j.1365-313x.2006.02843.x. [PMID: 16899083] - Porntep Chomcheon, Nongluksna Sriubolmas, Suthep Wiyakrutta, Nattaya Ngamrojanavanich, Narongsak Chaichit, Chulabhorn Mahidol, Somsak Ruchirawat, Prasat Kittakoop. Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic dothideomycete sp. LRUB20.
Journal of natural products.
2006 Sep; 69(9):1351-3. doi:
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Journal of neurochemistry.
2006 Jun; 97(5):1301-13. doi:
10.1111/j.1471-4159.2006.03797.x. [PMID: 16638022] - Oliver Schröder, Yulyana Yudina, Alan Sabirsh, Nadine Zahn, Jesper Z Haeggström, Jürgen Stein. 15-deoxy-Delta12,14-prostaglandin J2 inhibits the expression of microsomal prostaglandin E synthase type 2 in colon cancer cells.
Journal of lipid research.
2006 May; 47(5):1071-80. doi:
10.1194/jlr.m600008-jlr200. [PMID: 16495511] - Aimee Landar, Jaroslaw W Zmijewski, Dale A Dickinson, Claire Le Goffe, Michelle S Johnson, Ginger L Milne, Giuseppe Zanoni, Giovanni Vidari, Jason D Morrow, Victor M Darley-Usmar. Interaction of electrophilic lipid oxidation products with mitochondria in endothelial cells and formation of reactive oxygen species.
American journal of physiology. Heart and circulatory physiology.
2006 May; 290(5):H1777-87. doi:
10.1152/ajpheart.01087.2005. [PMID: 16387790] - Balázs Hauser, Jochen Kick, Zsolt Iványi, Pierre Asfar, Ulrich Ehrmann, Claus-Martin Muth, Maura Albicini, Ulrich Wachter, Josef Vogt, Michael Bauer, Uwe Bernd Brückner, Peter Radermacher, Hendrik Bracht. Effects of 15-deoxy-Delta12,14-prostaglandin-J2 during hyperdynamic porcine endotoxemia.
Intensive care medicine.
2006 May; 32(5):759-65. doi:
10.1007/s00134-006-0107-8. [PMID: 16534570] - A I Hubich, T A Zheldakova, T V Chernikhova, E V Koroleva, F A Lakhvich, M V Sholukh. Synthetic heteroprostanoids of A- and E-types as novel non-comprehensive inhibitors of adenylyl cyclase in rat hepatocytes.
Biochemical and biophysical research communications.
2006 Mar; 341(2):357-62. doi:
10.1016/j.bbrc.2005.12.196. [PMID: 16427025] - Rakesh Kumar Mahajan, T P S Walia, Sumanjit, T S Lobana. Cyclopentanone thiosemicarbazone, a new complexing agent for copper determination in biological samples by adsorptive stripping voltammetry.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2006 Mar; 22(3):389-92. doi:
10.2116/analsci.22.389. [PMID: 16733309] - Tilo Lübken, Norbert Arnold, Ludger Wessjohann, Christoph Böttcher, Jürgen Schmidt. Analysis of fungal cyclopentenone derivatives from Hygrophorus spp. by liquid chromatography/electrospray-tandem mass spectrometry.
Journal of mass spectrometry : JMS.
2006 Mar; 41(3):361-71. doi:
10.1002/jms.996. [PMID: 16453280] - Tracy M Wagner, James E Mullally, F A Fitzpatrick. Reactive lipid species from cyclooxygenase-2 inactivate tumor suppressor LKB1/STK11: cyclopentenone prostaglandins and 4-hydroxy-2-nonenal covalently modify and inhibit the AMP-kinase kinase that modulates cellular energy homeostasis and protein translation.
The Journal of biological chemistry.
2006 Feb; 281(5):2598-604. doi:
10.1074/jbc.m509723200. [PMID: 16311241]