cyclohexenone (BioDeep_00000868277)

Main id: BioDeep_00000004914

 

natural product


代谢物信息卡片


4-07-00-00124 (Beilstein Handbook Reference)

化学式: C6H8O (96.0575)
中文名称: 2-环己烯-1-酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C=CC(=O)CC1
InChI: InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2



数据库引用编号

13 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)

14 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 GAPDH, GCK, HPGDS, PTGS2, RAC1, TUBB4B
Peripheral membrane protein 4 CYP1B1, GCK, HSD17B6, PTGS2
Endoplasmic reticulum membrane 4 CYP1B1, HMOX1, PTGS2, RAC1
Nucleus 7 GAPDH, GCK, HMOX1, JUN, JUND, RAC1, TUBB4B
cytosol 8 ATP12A, GAPDH, GCK, HMOX1, HPGDS, LIPE, RAC1, TUBB4B
dendrite 1 RAC1
trans-Golgi network 1 RAC1
nucleoplasm 5 GCK, HMOX1, HPGDS, JUN, JUND
RNA polymerase II transcription regulator complex 2 JUN, JUND
Cell membrane 5 C5AR1, LIPE, RAC1, SMPD2, TNF
Lipid-anchor 1 RAC1
Cytoplasmic side 2 HMOX1, RAC1
lamellipodium 1 RAC1
ruffle membrane 1 RAC1
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 3 ATP12A, C5AR1, SMPD2
Golgi apparatus membrane 1 GCK
Synapse 1 RAC1
cell cortex 1 RAC1
cell surface 1 TNF
glutamatergic synapse 1 RAC1
Golgi membrane 2 GCK, INS
mitochondrial inner membrane 1 HADHA
neuronal cell body 1 TNF
postsynapse 1 RAC1
Cytoplasm, cytosol 2 GAPDH, LIPE
plasma membrane 6 ATP12A, C5AR1, GAPDH, RAC1, SMPD2, TNF
Membrane 5 CYP1B1, GAPDH, HMOX1, LIPE, RAC1
apical plasma membrane 1 ATP12A
basolateral plasma membrane 3 ATP12A, C5AR1, GCK
caveola 3 LIPE, PTGS2, SMPD2
extracellular exosome 3 GAPDH, RAC1, TUBB4B
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 HMOX1, HSD17B6, PTGS2, SMPD2
extracellular space 3 HMOX1, INS, TNF
perinuclear region of cytoplasm 2 GAPDH, HMOX1
mitochondrion 3 CYP1B1, GCK, HADHA
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 4 CYP1B1, GAPDH, HPGDS, HSD17B6
Microsome membrane 3 CYP1B1, HSD17B6, PTGS2
Secreted 2 INS, RAC1
extracellular region 4 INS, RAC1, TNF, TUBB4B
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 2 JUN, JUND
nuclear membrane 1 GAPDH
external side of plasma membrane 1 TNF
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 ATP12A
dendritic spine 1 RAC1
cytoplasmic vesicle 2 C5AR1, RAC1
microtubule cytoskeleton 2 GAPDH, TUBB4B
apical part of cell 1 C5AR1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 GAPDH
Apical cell membrane 1 ATP12A
Cell projection, lamellipodium 1 RAC1
Cytoplasm, perinuclear region 1 GAPDH
Mitochondrion inner membrane 1 HADHA
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 2 GAPDH, TUBB4B
focal adhesion 1 RAC1
microtubule 1 TUBB4B
mitochondrial nucleoid 1 HADHA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 2 JUN, JUND
phagocytic cup 1 TNF
cell periphery 1 SMPD2
mitotic spindle 1 TUBB4B
cytoskeleton 3 GAPDH, RAC1, TUBB4B
cytoplasmic ribonucleoprotein granule 1 RAC1
nuclear chromosome 1 JUN
Basolateral cell membrane 1 GCK
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
Recycling endosome membrane 1 RAC1
endosome lumen 1 INS
Lipid droplet 2 GAPDH, LIPE
Membrane, caveola 1 LIPE
axonemal microtubule 1 TUBB4B
Cell projection, dendrite 1 RAC1
Melanosome 1 RAC1
euchromatin 1 JUN
secretory granule lumen 1 INS
secretory granule membrane 2 C5AR1, RAC1
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
transcription repressor complex 1 JUND
transport vesicle 1 INS
azurophil granule lumen 1 TUBB4B
mitochondrial fatty acid beta-oxidation multienzyme complex 1 HADHA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 HMOX1
ribonucleoprotein complex 1 GAPDH
ficolin-1-rich granule membrane 1 RAC1
GAIT complex 1 GAPDH
transcription factor AP-1 complex 2 JUN, JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 1 RAC1
potassium:proton exchanging ATPase complex 1 ATP12A
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Liang Xu, Haiping Liu, Yucui Ma, Cui Wu, Ruiqi Li, Zhimao Chao. Comparative study of volatile components from male and female flower buds of Populus × tomentosa by HS-SPME-GC-MS. Natural product research. 2019 Jul; 33(14):2105-2108. doi: 10.1080/14786419.2018.1483929. [PMID: 29897251]
  • Tomoki Himiyama, Minoru Waki, Yoshifumi Maegawa, Shinji Inagaki. Cooperative Catalysis of an Alcohol Dehydrogenase and Rhodium-Modified Periodic Mesoporous Organosilica. Angewandte Chemie (International ed. in English). 2019 07; 58(27):9150-9154. doi: 10.1002/anie.201904116. [PMID: 31025503]
  • J Munkert, C Costa, O Budeanu, J Petersen, S Bertolucci, G Fischer, F Müller-Uri, W Kreis. Progesterone 5β-reductase genes of the Brassicaceae family as function-associated molecular markers. Plant biology (Stuttgart, Germany). 2015 Nov; 17(6):1113-22. doi: 10.1111/plb.12361. [PMID: 26108256]
  • Ericsson D Coy-Barrera, Luis E Cuca-Suárez, Michael Sefkow, Uwe Schilde. Cinerin C: a macrophyllin-type bicyclo[3.2.1]octane neolignan from Pleurothyrium cinereum (Lauraceae). Acta crystallographica. Section C, Crystal structure communications. 2012 Aug; 68(Pt 8):o320-2. doi: 10.1107/s0108270112030946. [PMID: 22850860]
  • Szymon Zubek, Sebastian Mielcarek, Katarzyna Turnau. Hypericin and pseudohypericin concentrations of a valuable medicinal plant Hypericum perforatum L. are enhanced by arbuscular mycorrhizal fungi. Mycorrhiza. 2012 Feb; 22(2):149-56. doi: 10.1007/s00572-011-0391-1. [PMID: 21626142]
  • Hua Guo, Tao Feng, Zheng-Hui Li, Ji-Kai Liu. Four new compounds from the basidiomycete Craterellus odoratus. Journal of Asian natural products research. 2012; 14(10):950-5. doi: 10.1080/10286020.2012.729508. [PMID: 23046466]
  • Jennifer Munkert, Peter Bauer, Edyta Burda, Frieder Müller-Uri, Wolfgang Kreis. Progesterone 5β-reductase of Erysimum crepidifolium: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant protein. Phytochemistry. 2011 Oct; 72(14-15):1710-7. doi: 10.1016/j.phytochem.2011.06.007. [PMID: 21767854]
  • Mingsheng Qi, Dongping Wang, Carl A Bradley, Youfu Zhao. Genome sequence analyses of Pseudomonas savastanoi pv. glycinea and subtractive hybridization-based comparative genomics with nine pseudomonads. PloS one. 2011 Jan; 6(1):e16451. doi: 10.1371/journal.pone.0016451. [PMID: 21304594]
  • Gedson Rodrigues de Morais Lima, Camila de Albuquerque Montenegro, Cynthia Layse Ferreira de Almeida, Petrônio Filgueiras de Athayde-Filho, José Maria Barbosa-Filho, Leônia Maria Batista. Database survey of anti-inflammatory plants in South America: a review. International journal of molecular sciences. 2011; 12(4):2692-749. doi: 10.3390/ijms12042692. [PMID: 21731467]
  • Clemens Stueckler, Nicole J Mueller, Christoph K Winkler, Silvia M Glueck, Karl Gruber, Georg Steinkellner, Kurt Faber. Bioreduction of alpha-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial and Helional. Dalton transactions (Cambridge, England : 2003). 2010 Sep; 39(36):8472-6. doi: 10.1039/c002971h. [PMID: 20461254]
  • Michael H Walter, Daniela S Floss, Dieter Strack. Apocarotenoids: hormones, mycorrhizal metabolites and aroma volatiles. Planta. 2010 Jun; 232(1):1-17. doi: 10.1007/s00425-010-1156-3. [PMID: 20396903]
  • Juan A López-Ráez, Adriaan Verhage, Iván Fernández, Juan M García, Concepción Azcón-Aguilar, Victor Flors, María J Pozo. Hormonal and transcriptional profiles highlight common and differential host responses to arbuscular mycorrhizal fungi and the regulation of the oxylipin pathway. Journal of experimental botany. 2010 Jun; 61(10):2589-601. doi: 10.1093/jxb/erq089. [PMID: 20378666]
  • Jonathan T Vogel, Michael H Walter, Patrick Giavalisco, Anna Lytovchenko, Wouter Kohlen, Tatsiana Charnikhova, Andrew J Simkin, Charles Goulet, Dieter Strack, Harro J Bouwmeester, Alisdair R Fernie, Harry J Klee. SlCCD7 controls strigolactone biosynthesis, shoot branching and mycorrhiza-induced apocarotenoid formation in tomato. The Plant journal : for cell and molecular biology. 2010 Jan; 61(2):300-11. doi: 10.1111/j.1365-313x.2009.04056.x. [PMID: 19845881]
  • Anna Fontana, Michael Reichelt, Stefan Hempel, Jonathan Gershenzon, Sybille B Unsicker. The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. Journal of chemical ecology. 2009 Jul; 35(7):833-43. doi: 10.1007/s10886-009-9654-0. [PMID: 19568812]
  • Cornelia Mrosk, Susanne Forner, Gerd Hause, Helge Küster, Joachim Kopka, Bettina Hause. Composite Medicago truncatula plants harbouring Agrobacterium rhizogenes-transformed roots reveal normal mycorrhization by Glomus intraradices. Journal of experimental botany. 2009; 60(13):3797-807. doi: 10.1093/jxb/erp220. [PMID: 19574251]
  • Daniela S Floss, Willibald Schliemann, Jürgen Schmidt, Dieter Strack, Michael H Walter. RNA interference-mediated repression of MtCCD1 in mycorrhizal roots of Medicago truncatula causes accumulation of C27 apocarotenoids, shedding light on the functional role of CCD1. Plant physiology. 2008 Nov; 148(3):1267-82. doi: 10.1104/pp.108.125062. [PMID: 18790999]
  • Zhongkui Sun, Joachim Hans, Michael H Walter, Radoslava Matusova, Jules Beekwilder, Francel W A Verstappen, Zhao Ming, Esther van Echtelt, Dieter Strack, Ton Bisseling, Harro J Bouwmeester. Cloning and characterisation of a maize carotenoid cleavage dioxygenase (ZmCCD1) and its involvement in the biosynthesis of apocarotenoids with various roles in mutualistic and parasitic interactions. Planta. 2008 Oct; 228(5):789-801. doi: 10.1007/s00425-008-0781-6. [PMID: 18716794]
  • Nagaaki Sato, Makoto Jitsuoka, Takunobu Shibata, Tomoko Hirohashi, Katsumasa Nonoshita, Minoru Moriya, Yuji Haga, Aya Sakuraba, Makoto Ando, Tomoyuki Ohe, Hisashi Iwaasa, Akira Gomori, Akane Ishihara, Akio Kanatani, Takehiro Fukami. (9S)-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, a selective and orally active neuropeptide Y Y5 receptor antagonist. Journal of medicinal chemistry. 2008 Aug; 51(15):4765-70. doi: 10.1021/jm8003587. [PMID: 18637668]
  • Willibald Schliemann, Barbara Kolbe, Jürgen Schmidt, Manfred Nimtz, Victor Wray. Accumulation of apocarotenoids in mycorrhizal roots of leek (Allium porrum). Phytochemistry. 2008 May; 69(8):1680-8. doi: 10.1016/j.phytochem.2008.02.015. [PMID: 18384822]
  • Masanori Yoneyama, Norito Nishiyama, Makoto Shuto, Chie Sugiyama, Koichi Kawada, Keiichi Seko, Reiko Nagashima, Kiyokazu Ogita. In vivo depletion of endogenous glutathione facilitates trimethyltin-induced neuronal damage in the dentate gyrus of mice by enhancing oxidative stress. Neurochemistry international. 2008 Mar; 52(4-5):761-9. doi: 10.1016/j.neuint.2007.09.003. [PMID: 17949856]
  • Willibald Schliemann, Christian Ammer, Dieter Strack. Metabolite profiling of mycorrhizal roots of Medicago truncatula. Phytochemistry. 2008 Jan; 69(1):112-46. doi: 10.1016/j.phytochem.2007.06.032. [PMID: 17706732]
  • Kohki Akiyama. Chemical identification and functional analysis of apocarotenoids involved in the development of arbuscular mycorrhizal symbiosis. Bioscience, biotechnology, and biochemistry. 2007 Jun; 71(6):1405-14. doi: 10.1271/bbb.70023. [PMID: 17587670]
  • Michael H Walter, Daniela S Floss, Joachim Hans, Thomas Fester, Dieter Strack. Apocarotenoid biosynthesis in arbuscular mycorrhizal roots: contributions from methylerythritol phosphate pathway isogenes and tools for its manipulation. Phytochemistry. 2007 Jan; 68(1):130-8. doi: 10.1016/j.phytochem.2006.09.032. [PMID: 17084869]
  • Willibald Schliemann, Jürgen Schmidt, Manfred Nimtz, Victor Wray, Thomas Fester, Dieter Strack. Accumulation of apocarotenoids in mycorrhizal roots of Ornithogalum umbellatum. Phytochemistry. 2006 Jun; 67(12):1196-205. doi: 10.1016/j.phytochem.2006.05.005. [PMID: 16790253]
  • Dieter Strack, Thomas Fester. Isoprenoid metabolism and plastid reorganization in arbuscular mycorrhizal roots. The New phytologist. 2006; 172(1):22-34. doi: 10.1111/j.1469-8137.2006.01837.x. [PMID: 16945086]
  • Kazuto Takaishi, Yohannes Alen, Kazuyoshi Kawazu, Naomichi Baba, Shuhei Nakajima. Synthesis and antinematodal activity of 3-n-alkylphenols. Bioscience, biotechnology, and biochemistry. 2004 Nov; 68(11):2398-400. doi: 10.1271/bbb.68.2398. [PMID: 15564683]
  • Chuihua Kong, Xiaohua Xu, Bin Zhou, Fei Hu, Chaoxian Zhang, Maoxin Zhang. Two compounds from allelopathic rice accession and their inhibitory activity on weeds and fungal pathogens. Phytochemistry. 2004 Apr; 65(8):1123-8. doi: 10.1016/j.phytochem.2004.02.017. [PMID: 15110693]
  • H Matsui, G Nakamura, Y Ishiga, H Toshima, Y Inagaki, K Toyoda, T Shiraishi, Y Ichinose. Structure and expression of 12-oxophytodienoate reductase (subgroup I) genes in pea, and characterization of the oxidoreductase activities of their recombinant products. Molecular genetics and genomics : MGG. 2004 Feb; 271(1):1-10. doi: 10.1007/s00438-003-0948-6. [PMID: 14727182]
  • Patricia Silva Melo, Nelson Durán, Clélia Akiko Hiruma-Lima, Alba Regina Monteiro Souza-Brito, Marcela Haun. Comparison of the gastroprotective effect of a diterpene lactone isolated from Croton cajucara with its synthetic derivatives. Journal of ethnopharmacology. 2003 Aug; 87(2-3):169-74. doi: 10.1016/s0378-8741(03)00139-9. [PMID: 12860303]
  • Tahar Mechichi, Erko Stackebrandt, Georg Fuchs. Alicycliphilus denitrificans gen. nov., sp. nov., a cyclohexanol-degrading, nitrate-reducing beta-proteobacterium. International journal of systematic and evolutionary microbiology. 2003 Jan; 53(Pt 1):147-152. doi: 10.1099/ijs.0.02276-0. [PMID: 12661531]
  • Thomas Fester, Diana Schmidt, Swanhild Lohse, Michael H Walter, Giovanni Giuliano, Peter M Bramley, Paul D Fraser, Bettina Hause, Dieter Strack. Stimulation of carotenoid metabolism in arbuscular mycorrhizal roots. Planta. 2002 Nov; 216(1):148-54. doi: 10.1007/s00425-002-0917-z. [PMID: 12430024]
  • A Subbiah Pandi, S Banumathi, D Velmurugan, S Shanmuga Sundara Raj, H K Fun, S Manikandan. 3-(p-chlorophenyl)-4-phenyl-4,5-dihydroisoxazole-5-spiro-2'-1',2',3',4'-tetrahydronaphthalen-1'-one. Acta crystallographica. Section C, Crystal structure communications. 2001 Jul; 57(Pt 7):819-20. doi: 10.1107/s0108270101003997. [PMID: 11443252]
  • A Braca, N De Tommasi, L Di Bari, C Pizza, M Politi, I Morelli. Antioxidant principles from Bauhinia tarapotensis. Journal of natural products. 2001 Jul; 64(7):892-5. doi: 10.1021/np0100845. [PMID: 11473417]
  • M L Cunningham, H C Price, R W O'Connor, M P Moorman, J F Mahler, J B Nold, D L Morgan. Inhalation toxicity studies of the alpha,beta-unsaturated ketones: 2-cyclohexene-1-one. Inhalation toxicology. 2001 Jan; 13(1):25-36. doi: 10.1080/713856767. [PMID: 11153058]
  • F Schaller, E W Weiler. Enzymes of octadecanoid biosynthesis in plants--12-oxo-phytodienoate 10,11-reductase. European journal of biochemistry. 1997 Apr; 245(2):294-9. doi: 10.1111/j.1432-1033.1997.t01-1-00294.x. [PMID: 9151956]
  • N C Hall, J M Carney, O J Plante, M Cheng, D A Butterfield. Effect of 2-cyclohexene-1-one-induced glutathione diminution on ischemia/reperfusion-induced alterations in the physical state of brain synaptosomal membrane proteins and lipids. Neuroscience. 1997 Mar; 77(1):283-90. doi: 10.1016/s0306-4522(96)00430-7. [PMID: 9044393]
  • L P Shornick, M J Holtzman. A cryptic, microsomal-type arachidonate 12-lipoxygenase is tonically inactivated by oxidation-reduction conditions in cultured epithelial cells. The Journal of biological chemistry. 1993 Jan; 268(1):371-6. doi: . [PMID: 8416945]
  • A P Timerman, R A Altschuld, C M Hohl, G P Brierley, A J Merola. Cellular glutathione and the response of adult rat heart myocytes to oxidant stress. Journal of molecular and cellular cardiology. 1990 May; 22(5):565-75. doi: 10.1016/0022-2828(90)90958-5. [PMID: 2388282]
  • T Masukawa, M Sai, Y Tochino. 2-cyclohexene-1-one-induced hyperglycemia in the mice. Japanese journal of pharmacology. 1989 Jul; 50(3):347-9. doi: 10.1254/jjp.50.347. [PMID: 2761134]
  • J P Shaw, I N Chou. Elevation of intracellular glutathione content associated with mitogenic stimulation of quiescent fibroblasts. Journal of cellular physiology. 1986 Nov; 129(2):193-8. doi: 10.1002/jcp.1041290210. [PMID: 3771652]
  • R G Schnellmann, L J Mandel. Multiple effects of presumed glutathione depletors on rabbit proximal tubules. Kidney international. 1986 Apr; 29(4):858-62. doi: 10.1038/ki.1986.77. [PMID: 3712969]
  • M Brezis, S Rosen, P Silva, F H Epstein. Selective glutathione depletion on function and structure of the isolated perfused rat kidney. Kidney international. 1983 Aug; 24(2):178-84. doi: 10.1038/ki.1983.142. [PMID: 6632520]
  • T Uemura, G Sakaguchi, T Ito, K Okazawa, S Sakai. Experimental diarrhea in cynomolgus monkeys by oral administration with Clostridium perfringens type A viable cells or enterotoxin. Japanese journal of medical science & biology. 1975 Jun; 28(3):165-77. doi: 10.7883/yoken1952.28.165. [PMID: 525]