FOH 5:1 (BioDeep_00000629759)

 

Secondary id: BioDeep_00000003914, BioDeep_00000408265, BioDeep_00001868078

PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


3-METHYL-3-BUTEN-1-OL

化学式: C5H10O (86.07316100000001)
中文名称: 3-甲基-3-丁烯-1-醇, 3-甲基-2-丁烯-1-醇, 2-甲基-3-丁烯-1-醇
谱图信息: 最多检出来源 Homo sapiens(bile_acids) 22.35%

分子结构信息

SMILES: C/C(C)=C\CO
InChI: InChI=1S/C5H10O/c1-3-5(2)4-6/h6H,2-4H2,1H3

描述信息

3-Methyl-2-buten-1-ol is an endogenous metabolite.
3-Methyl-2-buten-1-ol is an endogenous metabolite.

同义名列表

11 个代谢物同义名

2Z-Penten-1-ol; FOH 5:1; 3-METHYL-3-BUTEN-1-OL; ISOPRENOL; 3-METHYL-2-BUTEN-1-OL; 2-Methylenebutan-1-ol; 2-Methyl-3-buten-1-ol; Prenol; 3-Methyl-3-buten-1-OL; 3-Methyl-2-buten-1-OL; 2-Methyl-3-buten-1-ol



数据库引用编号

24 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)

20 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

  • Xin Jin, Michael Ackah, Lei Wang, Frank Kwarteng Amoako, Yisu Shi, Lionnelle Gyllye Essoh, Jianbin Li, Qiaonan Zhang, Haonan Li, Weiguo Zhao. Magnesium Nutrient Application Induces Metabolomics and Physiological Responses in Mulberry (Morus alba) Plants. International journal of molecular sciences. 2023 Jun; 24(11):. doi: 10.3390/ijms24119650. [PMID: 37298601]
  • Ryan P Sweeney, Todd L Lowary. A Route to Polyprenol Pyrophosphate-Based Probes of O-Polysaccharide Biosynthesis in Klebsiella pneumoniae O2a. Organic letters. 2019 02; 21(4):1050-1053. doi: 10.1021/acs.orglett.8b04093. [PMID: 30681873]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Ran Tao, Chengzhang Wang, Changwei Zhang, WenJun Li, Hao Zhou, Hongxia Chen, Jianzhong Ye. Characterization, Cytotoxicity, and Genotoxicity of TiO2 and Folate-Coupled Chitosan Nanoparticles Loading Polyprenol-Based Nanoemulsion. Biological trace element research. 2018 Jul; 184(1):60-74. doi: 10.1007/s12011-017-1184-y. [PMID: 28993980]
  • Hiroshi Sagami, Ewa Swiezewska, Yoshihiro Shidoji. The history and recent advances in research of polyprenol and its derivatives. Bioscience, biotechnology, and biochemistry. 2018 Jun; 82(6):947-955. doi: 10.1080/09168451.2017.1411775. [PMID: 29297247]
  • Miroslav Lísa, Michal Holčapek. UHPSFC/ESI-MS Analysis of Lipids. Methods in molecular biology (Clifton, N.J.). 2018; 1730(?):73-82. doi: 10.1007/978-1-4939-7592-1_5. [PMID: 29363066]
  • Jerry Eichler, Barbara Imperiali. Stereochemical Divergence of Polyprenol Phosphate Glycosyltransferases. Trends in biochemical sciences. 2018 01; 43(1):10-17. doi: 10.1016/j.tibs.2017.10.008. [PMID: 29183665]
  • Ruta Muceniece, Jana Namniece, Ilva Nakurte, Kaspars Jekabsons, Una Riekstina, Baiba Jansone. Pharmacological research on natural substances in Latvia: Focus on lunasin, betulin, polyprenol and phlorizin. Pharmacological research. 2016 11; 113(Pt B):760-770. doi: 10.1016/j.phrs.2016.03.040. [PMID: 27109319]
  • Emanuela Camera, Matteo Ludovici, Sara Tortorella, Jo-Linda Sinagra, Bruno Capitanio, Laura Goracci, Mauro Picardo. Use of lipidomics to investigate sebum dysfunction in juvenile acne. Journal of lipid research. 2016 06; 57(6):1051-8. doi: 10.1194/jlr.m067942. [PMID: 27127078]
  • Vyacheslav V Kozlov, Leonid L Danilov. Reversed-phase ion-pair high-performance liquid chromatography assay of polyprenyl diphosphate oligomer homologues. Journal of separation science. 2016 Feb; 39(3):525-7. doi: 10.1002/jssc.201501098. [PMID: 26608950]
  • Ran Tao, Chengzhang Wang, Jianzhong Ye, Hao Zhou, Hongxia Chen. Polyprenols of Ginkgo biloba Enhance Antibacterial Activity of Five Classes of Antibiotics. BioMed research international. 2016; 2016(?):4191938. doi: 10.1155/2016/4191938. [PMID: 27642597]
  • Chiara Martano, Vera Mugoni, Federica Dal Bello, Massimo M Santoro, Claudio Medana. Rapid high performance liquid chromatography-high resolution mass spectrometry methodology for multiple prenol lipids analysis in zebrafish embryos. Journal of chromatography. A. 2015 Sep; 1412(?):59-66. doi: 10.1016/j.chroma.2015.07.115. [PMID: 26283533]
  • Ewa Molińska nee Sosińska, Urszula Klimczak, Joanna Komaszyło, Dorota Derewiaka, Mieczysław Obiedziński, Magdalena Kania, Witold Danikiewicz, Ewa Swiezewska. Double bond stereochemistry influences the susceptibility of short-chain isoprenoids and polyprenols to decomposition by thermo-oxidation. Lipids. 2015 04; 50(4):359-70. doi: 10.1007/s11745-015-3998-8. [PMID: 25739731]
  • Ran Tao, Cheng-Zhang Wang, Zhen-Wu Kong. Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L. leaves. Molecules (Basel, Switzerland). 2013 Feb; 18(2):2166-82. doi: 10.3390/molecules18022166. [PMID: 23434869]
  • Mei-Juan Xu, Bin Wu, Tao Ding, Ji-Hong Chu, Chang-Yin Li, Jun Zhang, Ting Wu, Jian Wu, Shi-Jia Liu, Shen-Lin Liu, Wen-Zheng Ju, Ping Li. Simultaneous characterization of prenylated flavonoids and isoflavonoids in Psoralea corylifolia L. by liquid chromatography with diode-array detection and quadrupole time-of-flight mass spectrometry. Rapid communications in mass spectrometry : RCM. 2012 Oct; 26(19):2343-58. doi: 10.1002/rcm.6361. [PMID: 22956327]
  • Atena Jabbari, Mahdieh Davoodnejad, Maliheh Alimardani, Amir Assadieskandar, Ali Sadeghian, Hadi Safdari, Jebraeel Movaffagh, Hamid Sadeghian. Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors. Bioorganic & medicinal chemistry. 2012 Sep; 20(18):5518-26. doi: 10.1016/j.bmc.2012.07.025. [PMID: 22917856]
  • Jinhui Yu, Yanbin Wang, Hua Qian, Yunpeng Zhao, Bentong Liu, Chengxin Fu. Polyprenols from the needles of Taxus chinensis var. mairei. Fitoterapia. 2012 Jul; 83(5):831-7. doi: 10.1016/j.fitote.2012.01.007. [PMID: 22305943]
  • Sol A Green, Xiuyin Chen, Niels J Nieuwenhuizen, Adam J Matich, Mindy Y Wang, Barry J Bunn, Yar-Khing Yauk, Ross G Atkinson. Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). Journal of experimental botany. 2012 Mar; 63(5):1951-67. doi: 10.1093/jxb/err393. [PMID: 22162874]
  • Roberto Cecotti, Emanuele Carpana, Luca Falchero, Renato Paoletti, Aldo Tava. Determination of the volatile fraction of Polygonum bistorta L. at different growing stages and evaluation of its antimicrobial activity against two major honeybee (Apis mellifera) pathogens. Chemistry & biodiversity. 2012 Feb; 9(2):359-69. doi: 10.1002/cbdv.201100326. [PMID: 22344911]
  • Ana Marta Silva, Anabela Cordeiro-da-Silva, Graham H Coombs. Metabolic variation during development in culture of Leishmania donovani promastigotes. PLoS neglected tropical diseases. 2011 Dec; 5(12):e1451. doi: 10.1371/journal.pntd.0001451. [PMID: 22206037]
  • Maria Graça Miguel, Maria Dulce Antunes. Is propolis safe as an alternative medicine?. Journal of pharmacy & bioallied sciences. 2011 Oct; 3(4):479-95. doi: 10.4103/0975-7406.90101. [PMID: 22219581]
  • Lan Yang, Cheng-zhang Wang, Jian-zhong Ye, Hai-tao Li. Hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves on CCl4-induced hepatotoxicity in rats. Fitoterapia. 2011 Sep; 82(6):834-40. doi: 10.1016/j.fitote.2011.04.009. [PMID: 21596107]
  • Mara Schuler, Andreas Keller, Christina Backes, Katrin Philippar, Hans-Peter Lenhof, Petra Bauer. Transcriptome analysis by GeneTrail revealed regulation of functional categories in response to alterations of iron homeostasis in Arabidopsis thaliana. BMC plant biology. 2011 May; 11(?):87. doi: 10.1186/1471-2229-11-87. [PMID: 21592396]
  • Abdul Ahad, Mohammed Aqil, Kanchan Kohli, Yasmin Sultana, Mohd Mujeeb, Asgar Ali. Role of novel terpenes in transcutaneous permeation of valsartan: effectiveness and mechanism of action. Drug development and industrial pharmacy. 2011 May; 37(5):583-96. doi: 10.3109/03639045.2010.532219. [PMID: 21469947]
  • Ewa Ciepichal, Malgorzata Jemiola-Rzeminska, Jozefina Hertel, Ewa Swiezewska, Kazimierz Strzalka. Configuration of polyisoprenoids affects the permeability and thermotropic properties of phospholipid/polyisoprenoid model membranes. Chemistry and physics of lipids. 2011 May; 164(4):300-6. doi: 10.1016/j.chemphyslip.2011.03.004. [PMID: 21440533]
  • William B Rizzo. The role of fatty aldehyde dehydrogenase in epidermal structure and function. Dermato-endocrinology. 2011 Apr; 3(2):91-9. doi: 10.4161/derm.3.2.14619. [PMID: 21695018]
  • Codruta Ignea, Ivana Cvetkovic, Sofia Loupassaki, Panagiotis Kefalas, Christopher B Johnson, Sotirios C Kampranis, Antonios M Makris. Improving yeast strains using recyclable integration cassettes, for the production of plant terpenoids. Microbial cell factories. 2011 Jan; 10(?):4. doi: 10.1186/1475-2859-10-4. [PMID: 21276210]
  • Jan F C Glatz. Challenges in Fatty Acid and lipid physiology. Frontiers in physiology. 2011; 2(?):45. doi: 10.3389/fphys.2011.00045. [PMID: 21852975]
  • Martin Cerny, Filip Dycka, Janette Bobál'ová, Bretislav Brzobohaty. Early cytokinin response proteins and phosphoproteins of Arabidopsis thaliana identified by proteome and phosphoproteome profiling. Journal of experimental botany. 2011 Jan; 62(3):921-37. doi: 10.1093/jxb/erq322. [PMID: 20974740]
  • Jayaram Bhandari, A Heather Fitzpatrick, Dring N Crowell. Identification of a novel abscisic acid-regulated farnesol dehydrogenase from Arabidopsis. Plant physiology. 2010 Nov; 154(3):1116-27. doi: 10.1104/pp.110.157784. [PMID: 20807998]
  • S Genovese, F Epifano, G Carlucci, M C Marcotullio, M Curini, M Locatelli. Quantification of 4'-geranyloxyferulic acid, a new natural colon cancer chemopreventive agent, by HPLC-DAD in grapefruit skin extract. Journal of pharmaceutical and biomedical analysis. 2010 Oct; 53(2):212-4. doi: 10.1016/j.jpba.2010.01.041. [PMID: 20172682]
  • Tsuyoshi Goto, Nobuyuki Takahashi, Shizuka Hirai, Teruo Kawada. Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism. PPAR research. 2010; 2010(?):483958. doi: 10.1155/2010/483958. [PMID: 20613991]
  • Yuwen Wu, Qiuhong Pan, Wenjun Qu, Changqing Duan. Comparison of volatile profiles of nine litchi (Litchi chinensis Sonn.) cultivars from Southern China. Journal of agricultural and food chemistry. 2009 Oct; 57(20):9676-81. doi: 10.1021/jf902144c. [PMID: 19803519]
  • Y B Ryu, T J Ha, M J Curtis-Long, H W Ryu, S W Gal, K H Park. Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz. Journal of enzyme inhibition and medicinal chemistry. 2008 Dec; 23(6):922-30. doi: 10.1080/14756360701810207. [PMID: 18608767]
  • Masayoshi Muramatsu, Chikara Ohto, Shusei Obata, Eiji Sakuradani, Sakayu Shimizu. Various oils and detergents enhance the microbial production of farnesol and related prenyl alcohols. Journal of bioscience and bioengineering. 2008 Sep; 106(3):263-7. doi: 10.1263/jbb.106.263. [PMID: 18930003]
  • Geetu Singh, Prasoon Gupta, Preeti Rawat, Anju Puri, Gitika Bhatia, Rakesh Maurya. Antidyslipidemic activity of polyprenol from Coccinia grandis in high-fat diet-fed hamster model. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2007 Dec; 14(12):792-8. doi: 10.1016/j.phymed.2007.06.008. [PMID: 17689941]
  • Ewa Ciepichal, Jacek Wojcik, Tomasz Bienkowski, Magdalena Kania, Malgorzata Swist, Witold Danikiewicz, Andrzej Marczewski, Jozefina Hertel, Zdzislaw Matysiak, Ewa Swiezewska, Tadeusz Chojnacki. Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus. Chemistry and physics of lipids. 2007 Jun; 147(2):103-12. doi: 10.1016/j.chemphyslip.2007.04.002. [PMID: 17507003]
  • Francesco Epifano, Salvatore Genovese, Luigi Menghini, Massimo Curini. Chemistry and pharmacology of oxyprenylated secondary plant metabolites. Phytochemistry. 2007 Apr; 68(7):939-53. doi: 10.1016/j.phytochem.2007.01.019. [PMID: 17343885]
  • Andrzej Marczewski, Ewa Ciepichal, Le Xuan Canh, Tran The Bach, Ewa Swiezewska, Tadeusz Chojnacki. The search for polyprenols in dendroflora of Vietnam. Acta biochimica Polonica. 2007; 54(4):727-32. doi: 10.18388/abp.2007_3142. [PMID: 18066396]
  • Teresa A Garrett, Ziqiang Guan, Christian R H Raetz. Analysis of ubiquinones, dolichols, and dolichol diphosphate-oligosaccharides by liquid chromatography-electrospray ionization-mass spectrometry. Methods in enzymology. 2007; 432(?):117-43. doi: 10.1016/s0076-6879(07)32005-3. [PMID: 17954215]
  • Frank Röck, Sven Mueller, Udo Weimar, Hans-Georg Rammensee, Peter Overath. Comparative analysis of volatile constituents from mice and their urine. Journal of chemical ecology. 2006 Jun; 32(6):1333-46. doi: 10.1007/s10886-006-9091-2. [PMID: 16770722]
  • Massimo Curini, Giancarlo Cravotto, Francesco Epifano, Giovanni Giannone. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Current medicinal chemistry. 2006; 13(2):199-222. doi: 10.2174/092986706775197890. [PMID: 16472213]
  • Takeshi Bamba, Eiiciro Fukusaki, Hiroshi Minakuchi, Yoshihisa Nakazawa, Akio Kobayashi. Separation of polyprenol and dolichol by monolithic silica capillary column chromatography. Journal of lipid research. 2005 Oct; 46(10):2295-8. doi: 10.1194/jlr.m500185-jlr200. [PMID: 16061949]
  • Jullian Jones, Karthik Viswanathan, Sharon S Krag, Michael J Betenbaugh. Polyprenyl lipid synthesis in mammalian cells expressing human cis-prenyl transferase. Biochemical and biophysical research communications. 2005 Jun; 331(2):379-83. doi: 10.1016/j.bbrc.2005.03.181. [PMID: 15850770]
  • Eoin Fahy, Shankar Subramaniam, H Alex Brown, Christopher K Glass, Alfred H Merrill, Robert C Murphy, Christian R H Raetz, David W Russell, Yousuke Seyama, Walter Shaw, Takao Shimizu, Friedrich Spener, Gerrit van Meer, Michael S VanNieuwenhze, Stephen H White, Joseph L Witztum, Edward A Dennis. A comprehensive classification system for lipids. Journal of lipid research. 2005 May; 46(5):839-61. doi: 10.1194/jlr.e400004-jlr200. [PMID: 15722563]
  • Marcin Chouda, Wiesław Jankowski. The occurrence of polyprenols in seeds and leaves of woody plants. Acta biochimica Polonica. 2005; 52(1):243-53. doi: 055201243. [PMID: 15827621]
  • Agnieszka Bajda, Tadeusz Chojnacki, Józefina Hertel, Ewa Swiezewska, Jacek Wójcik, Alicja Kaczkowska, Andrzej Marczewski, Tomasz Bojarczuk, Piotr Karolewski, Jacek Oleksyn. Light conditions alter accumulation of long chain polyprenols in leaves of trees and shrubs throughout the vegetation season. Acta biochimica Polonica. 2005; 52(1):233-41. doi: 055201233. [PMID: 15827620]
  • Yonghui Li, Shulan Su, Zhen Ouyang, Kedi Yang. [Studies on purification of polyprenol from Ginkgo biloba L. leaves]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 May; 27(5):337-9. doi: ". [PMID: 15376386]
  • Alvaro Acosta-Serrano, Jessica O'Rear, George Quellhorst, Soo Hee Lee, Kuo-Yuan Hwa, Sharon S Krag, Paul T Englund. Defects in the N-linked oligosaccharide biosynthetic pathway in a Trypanosoma brucei glycosylation mutant. Eukaryotic cell. 2004 Apr; 3(2):255-63. doi: 10.1128/ec.3.2.255-263.2004. [PMID: 15075256]
  • Karina Sinding Hansen, Charlotte Kristensen, David Bruce Tattersall, Patrik Raymond Jones, Carl Erik Olsen, Søren Bak, Birger Lindberg Møller. The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor. Phytochemistry. 2003 Sep; 64(1):143-51. doi: 10.1016/s0031-9422(03)00261-9. [PMID: 12946413]
  • Yidong Lei, Peng Nan, Tashi Tsering, Zhankui Bai, Chunjie Tian, Yang Zhong. Chemical composition of the essential oils of two Rhodiola species from Tibet. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Mar; 58(3-4):161-4. doi: 10.1515/znc-2003-3-402. [PMID: 12710720]
  • Teris A van Beek. Chemical analysis of Ginkgo biloba leaves and extracts. Journal of chromatography. A. 2002 Aug; 967(1):21-55. doi: 10.1016/s0021-9673(02)00172-3. [PMID: 12219929]
  • Adrián A Vojnov, Daniel E Bassi, Michael J Daniels, Marcelo A Dankert. Biosynthesis of a substituted cellulose from a mutant strain of Xanthomonas campestris. Carbohydrate research. 2002 Feb; 337(4):315-26. doi: 10.1016/s0008-6215(01)00322-6. [PMID: 11841812]
  • C Bertrand, N Fabre, C Moulis. Constituents of Pilocarpus trachylophus. Fitoterapia. 2001 Nov; 72(7):844-7. doi: 10.1016/s0367-326x(01)00325-2. [PMID: 11677031]
  • T Bamba, W Fukasaki, S Kajiyama, K Ute, T Kitayama, A Kobayashi. High-resolution analysis of polyprenols by supercritical fluid chromatography. Journal of chromatography. A. 2001 Mar; 911(1):113-7. doi: 10.1016/s0021-9673(00)01250-4. [PMID: 11269588]
  • C W Hall, K R McLachlan, S S Krag, A R Robbins. Reduced utilization of Man5GlcNAc2-P-P-lipid in a Lec9 mutant of Chinese hamster ovary cells: analysis of the steps in oligosaccharide-lipid assembly. Journal of cellular biochemistry. 1997 Nov; 67(2):201-15. doi: . [PMID: 9328825]
  • E Yasugi, Y Yokoyama, Y Seyama, K Kano, Y Hayashi, M Oshima. Dolichyl phosphate, a potent inducer of apoptosis in rat glioma C6 cells. Biochemical and biophysical research communications. 1995 Nov; 216(3):848-53. doi: 10.1006/bbrc.1995.2699. [PMID: 7488203]
  • A R Kendall. Cost containment: why unnecessary urine cultures?. The Journal of urology. 1979 May; 121(5):691. doi: 10.1016/s0022-5347(17)56955-4. [PMID: 439280]
  • E N Nemchinov, O N Ankhimiuk. [Periarteritis nodosa complicated by perirenal hematoma]. Klinicheskaia meditsina. 1975 Jun; 53(6):122-3. doi: NULL. [PMID: 2801]
  • K J Thorne. Incorporation of radioactive mevalonate into C50 and C55 phenols by Streptococcus mutans. The Biochemical journal. 1973 Nov; 135(3):567-8. doi: 10.1042/bj1350567. [PMID: 4772282]
  • . . . . doi: . [PMID: 14725857]