(S)-3,7-Dimethyl-1,6-octadiene (BioDeep_00000021231)

   

human metabolite Endogenous


代谢物信息卡片


(3S)-3,7-dimethylocta-1,6-diene

化学式: C10H18 (138.1408)
中文名称: 二氢月桂烯, （3S）-3,7-二甲基辛-1,6-二烯
谱图信息: 最多检出来源 Homo sapiens(feces) 100%

分子结构信息

SMILES: C=CC(C)CCC=C(C)C
InChI: InChI=1S/C10H18/c1-5-10(4)8-6-7-9(2)3/h5,7,10H,1,6,8H2,2-4H3

描述信息

(S)-3,7-Dimethyl-1,6-octadiene belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

同义名列表

8 个代谢物同义名

(3S)-3,7-dimethylocta-1,6-diene; (S)-3,7-Dimethyl-1,6-octadiene; beta-Citronellene; DIHYDROMYRCENE; Citronellene; (S)-Linalol; Dihydromyrcene; (3S)-3,7-dimethylocta-1,6-diene



数据库引用编号

10 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)

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。

亚细胞结构定位 关联基因列表


文献列表

  • Hiroshi Ueno, Atsumi Shimada, Shunsuke Suemitsu, Shinji Murakami, Naoya Kitamura, Kenta Wani, Yu Takahashi, Yosuke Matsumoto, Motoi Okamoto, Takeshi Ishihara. Increased anxiety-related behavior in mice following β-citronellol inhalation. The Libyan journal of medicine. 2020 Dec; 15(1):1767275. doi: 10.1080/19932820.2020.1767275. [PMID: 32475228]
  • Laetitia Bonifait, Annie Marquis, Salvatore Genovese, Francesco Epifano, Daniel Grenier. Synthesis and antimicrobial activity of geranyloxy- and farnesyloxy-acetophenone derivatives against oral pathogens. Fitoterapia. 2012 Sep; 83(6):996-9. doi: 10.1016/j.fitote.2012.06.003. [PMID: 22698715]
  • Chin-Lin Hsu, Fang-Rong Chang, Pei-Yu Tseng, Yi-Fen Chen, Mohamed El-Shazly, Ying-Chi Du, Song-Chwan Fang. Geranyl flavonoid derivatives from the fresh leaves of Artocarpus communis and their anti-inflammatory activity. Planta medica. 2012 Jun; 78(10):995-1001. doi: 10.1055/s-0031-1298580. [PMID: 22618373]
  • Jung Keun Cho, Young Bae Ryu, Marcus J Curtis-Long, Hyung Won Ryu, Heung Joo Yuk, Dae Wook Kim, Hye Jin Kim, Woo Song Lee, Ki Hun Park. Cholinestrase inhibitory effects of geranylated flavonoids from Paulownia tomentosa fruits. Bioorganic & medicinal chemistry. 2012 Apr; 20(8):2595-602. doi: 10.1016/j.bmc.2012.02.044. [PMID: 22445674]
  • Mi-Yeon Cho, Su-Young Park, Sumin Park, Yong Rok Lee, Gi-Dong Han, Jung-Ae Kim. Geranyl derivative of phloroacetophenone induces cancer cell-specific apoptosis through Bax-mediated mitochondrial pathway in MCF-7 human breast cancer cells. Biological & pharmaceutical bulletin. 2012; 35(1):98-104. doi: 10.1248/bpb.35.98. [PMID: 22223344]
  • Md Sarfaraj Hussain, Sheeba Fareed, Saba Ansari, Md Akhlaquer Rahman, Iffat Zareen Ahmad, Mohd Saeed. Current approaches toward production of secondary plant metabolites. Journal of pharmacy & bioallied sciences. 2012 Jan; 4(1):10-20. doi: 10.4103/0975-7406.92725. [PMID: 22368394]
  • Axel Schmidt, Raimund Nagel, Trygve Krekling, Erik Christiansen, Jonathan Gershenzon, Paal Krokene. Induction of isoprenyl diphosphate synthases, plant hormones and defense signalling genes correlates with traumatic resin duct formation in Norway spruce (Picea abies). Plant molecular biology. 2011 Dec; 77(6):577-90. doi: 10.1007/s11103-011-9832-7. [PMID: 22002747]
  • Petra M Bleeker, Eleni A Spyropoulou, Paul J Diergaarde, Hanne Volpin, Michiel T J De Both, Philipp Zerbe, Joerg Bohlmann, Vasiliki Falara, Yuki Matsuba, Eran Pichersky, Michel A Haring, Robert C Schuurink. RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes. Plant molecular biology. 2011 Nov; 77(4-5):323-36. doi: 10.1007/s11103-011-9813-x. [PMID: 21818683]
  • 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]
  • Nora C Lawo, Georg J F Weingart, Rainer Schuhmacher, Astrid Forneck. The volatile metabolome of grapevine roots: first insights into the metabolic response upon phylloxera attack. Plant physiology and biochemistry : PPB. 2011 Sep; 49(9):1059-63. doi: 10.1016/j.plaphy.2011.06.008. [PMID: 21764593]
  • Juliana Almeida, Leandro Quadrana, Ramón Asís, Nathalia Setta, Fabiana de Godoy, Luisa Bermúdez, Santiago N Otaiza, Junia V Corrêa da Silva, Alisdair R Fernie, Fernando Carrari, Magdalena Rossi. Genetic dissection of vitamin E biosynthesis in tomato. Journal of experimental botany. 2011 Jul; 62(11):3781-98. doi: 10.1093/jxb/err055. [PMID: 21527625]
  • Helge Joa, Sylvia Vogl, Atanas G Atanasov, Martin Zehl, Thomas Nakel, Nanang Fakhrudin, Elke H Heiss, Paolo Picker, Ernst Urban, Christoph Wawrosch, Johannes Saukel, Gottfried Reznicek, Brigitte Kopp, Verena M Dirsch. Identification of ostruthin from Peucedanum ostruthium rhizomes as an inhibitor of vascular smooth muscle cell proliferation. Journal of natural products. 2011 Jun; 74(6):1513-6. doi: 10.1021/np200072a. [PMID: 21627108]
  • Enrique C Morales-Villegas, Germano Di Sciascio, Carlo Briguori. Statins: cardiovascular risk reduction in percutaneous coronary intervention-basic and clinical evidence of hyperacute use of statins. International journal of hypertension. 2011 Mar; 2011(?):904742. doi: 10.4061/2011/904742. [PMID: 21461336]
  • Christopher I Keeling, Sabrina Weisshaar, Steven G Ralph, Sharon Jancsik, Britta Hamberger, Harpreet K Dullat, Jörg Bohlmann. Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.). BMC plant biology. 2011 Mar; 11(?):43. doi: 10.1186/1471-2229-11-43. [PMID: 21385377]
  • Jer-An Lin, Song-Chwan Fang, Chi-Hao Wu, Shang-Ming Huang, Gow-Chin Yen. Anti-inflammatory effect of the 5,7,4'-trihydroxy-6-geranylflavanone isolated from the fruit of Artocarpus communis in S100B-induced human monocytes. Journal of agricultural and food chemistry. 2011 Jan; 59(1):105-11. doi: 10.1021/jf103455g. [PMID: 21126004]
  • Eric T McDowell, Jeremy Kapteyn, Adam Schmidt, Chao Li, Jin-Ho Kang, Anne Descour, Feng Shi, Matthew Larson, Anthony Schilmiller, Lingling An, A Daniel Jones, Eran Pichersky, Carol A Soderlund, David R Gang. Comparative functional genomic analysis of Solanum glandular trichome types. Plant physiology. 2011 Jan; 155(1):524-39. doi: 10.1104/pp.110.167114. [PMID: 21098679]
  • Jyotsana Singhal, Lokesh Nagaprashantha, Rit Vatsyayan, Sanjay Awasthi, Sharad S Singhal. RLIP76, a glutathione-conjugate transporter, plays a major role in the pathogenesis of metabolic syndrome. PloS one. 2011; 6(9):e24688. doi: 10.1371/journal.pone.0024688. [PMID: 21931813]
  • Qingping Xu, Tadashi Eguchi, Irimpan I Mathews, Christopher L Rife, Hsiu-Ju Chiu, Carol L Farr, Julie Feuerhelm, Lukasz Jaroszewski, Heath E Klock, Mark W Knuth, Mitchell D Miller, Dana Weekes, Marc-André Elsliger, Ashley M Deacon, Adam Godzik, Scott A Lesley, Ian A Wilson. Insights into substrate specificity of geranylgeranyl reductases revealed by the structure of digeranylgeranylglycerophospholipid reductase, an essential enzyme in the biosynthesis of archaeal membrane lipids. Journal of molecular biology. 2010 Dec; 404(3):403-17. doi: 10.1016/j.jmb.2010.09.032. [PMID: 20869368]
  • Eric Martinez, Gunnar N Schroeder, Cedric N Berger, Sau Fung Lee, Keith S Robinson, Luminita Badea, Nandi Simpson, Randy A Hall, Elizabeth L Hartland, Valerie F Crepin, Gad Frankel. Binding to Na(+) /H(+) exchanger regulatory factor 2 (NHERF2) affects trafficking and function of the enteropathogenic Escherichia coli type III secretion system effectors Map, EspI and NleH. Cellular microbiology. 2010 Dec; 12(12):1718-31. doi: 10.1111/j.1462-5822.2010.01503.x. [PMID: 20618342]
  • Diane M Martin, Sébastien Aubourg, Marina B Schouwey, Laurent Daviet, Michel Schalk, Omid Toub, Steven T Lund, Jörg Bohlmann. Functional annotation, genome organization and phylogeny of the grapevine (Vitis vinifera) terpene synthase gene family based on genome assembly, FLcDNA cloning, and enzyme assays. BMC plant biology. 2010 Oct; 10(?):226. doi: 10.1186/1471-2229-10-226. [PMID: 20964856]
  • Geng Yu, Thuong T H Nguyen, Yongxia Guo, Ines Schauvinhold, Michele E Auldridge, Nazmul Bhuiyan, Imri Ben-Israel, Yoko Iijima, Eyal Fridman, Joseph P Noel, Eran Pichersky. Enzymatic functions of wild tomato methylketone synthases 1 and 2. Plant physiology. 2010 Sep; 154(1):67-77. doi: 10.1104/pp.110.157073. [PMID: 20605911]
  • Jin-Ho Kang, Guanghui Liu, Feng Shi, A Daniel Jones, Randolph M Beaudry, Gregg A Howe. The tomato odorless-2 mutant is defective in trichome-based production of diverse specialized metabolites and broad-spectrum resistance to insect herbivores. Plant physiology. 2010 Sep; 154(1):262-72. doi: 10.1104/pp.110.160192. [PMID: 20668059]
  • Anthony L Schilmiller, Dennis P Miner, Matthew Larson, Eric McDowell, David R Gang, Curtis Wilkerson, Robert L Last. Studies of a biochemical factory: tomato trichome deep expressed sequence tag sequencing and proteomics. Plant physiology. 2010 Jul; 153(3):1212-23. doi: 10.1104/pp.110.157214. [PMID: 20431087]
  • Anthony Schilmiller, Feng Shi, Jeongwoon Kim, Amanda L Charbonneau, Daniel Holmes, A Daniel Jones, Robert L Last. Mass spectrometry screening reveals widespread diversity in trichome specialized metabolites of tomato chromosomal substitution lines. The Plant journal : for cell and molecular biology. 2010 May; 62(3):391-403. doi: 10.1111/j.1365-313x.2010.04154.x. [PMID: 20113441]
  • Karel Smejkal, Jana Svacinová, Tereza Slapetová, Kristýna Schneiderová, Stefano Dall'acqua, Gabbriella Innocenti, Veronika Závalová, Peter Kollár, Stanislav Chudík, Radek Marek, Ondrej Julínek, Marie Urbanová, Murat Kartal, Marek Csöllei, Karel Dolezal. Cytotoxic activities of several geranyl-substituted flavanones. Journal of natural products. 2010 Apr; 73(4):568-72. doi: 10.1021/np900681y. [PMID: 20192247]
  • Brenda Modak, Ana María Sandino, Loredana Arata, Gloria Cárdenas-Jirón, René Torres. Inhibitory effect of aromatic geranyl derivatives isolated from Heliotropium filifolium on infectious pancreatic necrosis virus replication. Veterinary microbiology. 2010 Feb; 141(1-2):53-8. doi: 10.1016/j.vetmic.2009.09.005. [PMID: 19818567]
  • Axel Schmidt, Betty Wächtler, Ulrike Temp, Trygve Krekling, Armand Séguin, Jonathan Gershenzon. A bifunctional geranyl and geranylgeranyl diphosphate synthase is involved in terpene oleoresin formation in Picea abies. Plant physiology. 2010 Feb; 152(2):639-55. doi: 10.1104/pp.109.144691. [PMID: 19939949]
  • Jin-Ho Kang, Feng Shi, A Daniel Jones, M David Marks, Gregg A Howe. Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry. Journal of experimental botany. 2010 Feb; 61(4):1053-64. doi: 10.1093/jxb/erp370. [PMID: 20018901]
  • Tao-Hsin Chang, Fu-Lien Hsieh, Tzu-Ping Ko, Kuo-Hsun Teng, Po-Huang Liang, Andrew H-J Wang. Structure of a heterotetrameric geranyl pyrophosphate synthase from mint (Mentha piperita) reveals intersubunit regulation. The Plant cell. 2010 Feb; 22(2):454-67. doi: 10.1105/tpc.109.071738. [PMID: 20139160]
  • S Hooper, C Gaggioli, E Sahai. A chemical biology screen reveals a role for Rab21-mediated control of actomyosin contractility in fibroblast-driven cancer invasion. British journal of cancer. 2010 Jan; 102(2):392-402. doi: 10.1038/sj.bjc.6605469. [PMID: 19953096]
  • Brenda Modak, Melissa Salina, Jesús Rodilla, René Torres. Study of the chemical composition of the resinous exudate isolated from Heliotropium sclerocarpum and evaluation of the antioxidant properties of the phenolic compounds and the resin. Molecules (Basel, Switzerland). 2009 Nov; 14(11):4625-33. doi: 10.3390/molecules14114625. [PMID: 19924090]
  • Virginie Party, Christophe Hanot, Imene Said, Didier Rochat, Michel Renou. Plant terpenes affect intensity and temporal parameters of pheromone detection in a moth. Chemical senses. 2009 Nov; 34(9):763-74. doi: 10.1093/chemse/bjp060. [PMID: 19770215]
  • Brenda Modak, Macarena Rojas, René Torres. Chemical analysis of the resinous exudate isolated from Heliotropium taltalense and evaluation of the antioxidant activity of the phenolics components and the resin in homogeneous and heterogeneous systems. Molecules (Basel, Switzerland). 2009 Jun; 14(6):1980-9. doi: 10.3390/molecules14061980. [PMID: 19512999]
  • Jorge M S Faria, Inês S Nunes, A Cristina Figueiredo, Luis G Pedro, Helena Trindade, José G Barroso. Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components. Biotechnology letters. 2009 Jun; 31(6):897-903. doi: 10.1007/s10529-009-9934-3. [PMID: 19205895]
  • Sieglinde Kofler, Christoph Schlichting, Sarika Jankl, Thomas Nickel, Michael Weis. Dual mode of HMG-CoA reductase inhibition on dendritic cell invasion. Atherosclerosis. 2008 Mar; 197(1):105-10. doi: 10.1016/j.atherosclerosis.2007.08.005. [PMID: 17888931]
  • Shigenori Kumazawa, Reika Ueda, Tomoko Hamasaka, Syuichi Fukumoto, Takunori Fujimoto, Tsutomu Nakayama. Antioxidant prenylated flavonoids from propolis collected in Okinawa, Japan. Journal of agricultural and food chemistry. 2007 Sep; 55(19):7722-5. doi: 10.1021/jf071187h. [PMID: 17711339]
  • Yu Wang, Kedi Xu, Lin Lin, Yuanjiang Pan, Xiaoxiang Zheng. Geranyl flavonoids from the leaves of Artocarpus altilis. Phytochemistry. 2007 May; 68(9):1300-6. doi: 10.1016/j.phytochem.2007.01.009. [PMID: 17363017]
  • Nicholas A Malmquist, Jeffrey Baldwin, Margaret A Phillips. Detergent-dependent kinetics of truncated Plasmodium falciparum dihydroorotate dehydrogenase. The Journal of biological chemistry. 2007 Apr; 282(17):12678-86. doi: 10.1074/jbc.m609893200. [PMID: 17329250]
  • Marimuthu Srinivasan, Adluri R Sudheer, Venugopal P Menon. Ferulic Acid: therapeutic potential through its antioxidant property. Journal of clinical biochemistry and nutrition. 2007 Mar; 40(2):92-100. doi: 10.3164/jcbn.40.92. [PMID: 18188410]
  • Clive Bate, Louis Rumbold, Alun Williams. Cholesterol synthesis inhibitors protect against platelet-activating factor-induced neuronal damage. Journal of neuroinflammation. 2007 Jan; 4(?):5. doi: 10.1186/1742-2094-4-5. [PMID: 17233902]
  • Natsajee Nualkaew, Wanchai De-Eknamkul, Toni M Kutchan, Meinhart H Zenk. Membrane-bound geranylgeranyl diphosphate phosphatases: purification and characterization from Croton stellatopilosus leaves. Phytochemistry. 2006 Aug; 67(15):1613-20. doi: 10.1016/j.phytochem.2005.12.014. [PMID: 16445953]
  • L Del Toro-Sánchez, S Sánchez, M A Ortiz, S Villanueva, E Lugo-Cervantes. Generation of aroma compounds from Ditaxis heterantha by Saccharomyces cerevisiae. Applied microbiology and biotechnology. 2006 Aug; 72(1):155-162. doi: 10.1007/s00253-005-0244-y. [PMID: 16547703]
  • Tomohisa Kuzuyama, Joseph P Noel, Stéphane B Richard. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature. 2005 Jun; 435(7044):983-7. doi: 10.1038/nature03668. [PMID: 15959519]
  • Michael Wolfertz, Thomas D Sharkey, Wilhelm Boland, Frank Kühnemann. Rapid regulation of the methylerythritol 4-phosphate pathway during isoprene synthesis. Plant physiology. 2004 Aug; 135(4):1939-45. doi: 10.1104/pp.104.043737. [PMID: 15286290]
  • Martin Völkert, Koji Uwai, Andreas Tebbe, Boriana Popkirova, Melanie Wagner, Jürgen Kuhlmann, Herbert Waldmann. Synthesis and biological activity of photoactivatable N-ras peptides and proteins. Journal of the American Chemical Society. 2003 Oct; 125(42):12749-58. doi: 10.1021/ja036178d. [PMID: 14558822]
  • Chien-Chih Chen, Yu-Ling Huang, Pei-Yu Yeh, Jun-Chih Ou. Cyclized geranyl stilbenes from the rhizomes of Helminthostachys zeylanica. Planta medica. 2003 Oct; 69(10):964-7. doi: 10.1055/s-2003-45112. [PMID: 14648406]
  • Chihiro Ito, Masataka Itoigawa, Tomoko Takakura, Nijisiri Ruangrungsi, Fumio Enjo, Harukuni Tokuda, Hoyoku Nishino, Hiroshi Furukawa. Chemical constituents of Garcinia fusca: structure elucidation of eight new xanthones and their cancer chemopreventive activity. Journal of natural products. 2003 Feb; 66(2):200-5. doi: 10.1021/np020290s. [PMID: 12608849]
  • Akiyuki Takaya, Yuan-Wei Zhang, Kasem Asawatreratanakul, Dhirayos Wititsuwannakul, Rapepun Wititsuwannakul, Seiji Takahashi, Tanetoshi Koyama. Cloning, expression and characterization of a functional cDNA clone encoding geranylgeranyl diphosphate synthase of Hevea brasiliensis. Biochimica et biophysica acta. 2003 Jan; 1625(2):214-20. doi: 10.1016/s0167-4781(02)00602-4. [PMID: 12531482]
  • Ibrahim Jantan, Mazura Md Pisar, Muhammad Sum Idris, M Taher, Rasadah Mat Ali. In vitro inhibitory effect of rubraxanthone isolated from Garcinia parvifolia on platelet-activating factor receptor binding. Planta medica. 2002 Dec; 68(12):1133-4. doi: 10.1055/s-2002-36343. [PMID: 12494345]
  • Anastasia L Crowell, David C Williams, Edward M Davis, Mark R Wildung, Rodney Croteau. Molecular cloning and characterization of a new linalool synthase. Archives of biochemistry and biophysics. 2002 Sep; 405(1):112-21. doi: 10.1016/s0003-9861(02)00348-x. [PMID: 12176064]
  • Mitchell L Wise, Marek Urbansky, Gregory L Helms, Robert M Coates, Rodney Croteau. Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis. Journal of the American Chemical Society. 2002 Jul; 124(29):8546-7. doi: 10.1021/ja0265714. [PMID: 12121093]
  • Y J Xu, Y H Lai, Z Imiyabir, S H Goh. Xanthones from Garcinia parvifolia. Journal of natural products. 2001 Sep; 64(9):1191-5. doi: 10.1021/np0101393. [PMID: 11575954]
  • J Potter, R L Smith, A M Api. An assessment of the release of inorganic cyanide from the fragrance materials benzyl cyanide, geranyl nitrile and citronellyl nitrile applied dermally to the rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Feb; 39(2):147-51. doi: 10.1016/s0278-6915(00)00125-3. [PMID: 11267708]
  • J Potter, R L Smith, A M Api. Urinary thiocyanate levels as a biomarker for the generation of inorganic cyanide from benzyl cyanide in the rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Feb; 39(2):141-6. doi: 10.1016/s0278-6915(00)00126-5. [PMID: 11267707]