Undecane (BioDeep_00000019471)

   

human metabolite Endogenous natural product


代谢物信息卡片


CH3-[CH2]9-CH3

化学式: C11H24 (156.1878)
中文名称: 正十一烷标准溶液, 十一烷
谱图信息: 最多检出来源 Mus musculus(feces) 1.77%

分子结构信息

SMILES: CCCCCCCCCCC
InChI: InChI=1S/C11H24/c1-3-5-7-9-11-10-8-6-4-2/h3-11H2,1-2H3

描述信息

Undecane, also known as CH3-[CH2]9-CH3 or hendekan, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, undecane is considered to be a hydrocarbon lipid molecule. Undecane may also be used as an internal standard in gas chromatography when working with other hydrocarbons. For example, if one is working with a 50 m crosslinked methyl silicone capillary column with an oven temperature increasing slowly, beginning around 60 °C, an 11-carbon molecule like undecane may be used as an internal standard to be compared with the retention times of other 10-, 11-, or 12- carbon molecules, depending on their structures. Undecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. undecane has been detected, but not quantified, in cardamoms. This could make undecane a potential biomarker for the consumption of these foods. Since the boiling point of undecane (196 °C) is well known, it may be used as a comparison for retention times in a gas chromatograph for molecules whose structure has been freshly elucidated. It has 159 isomers. It is used as a mild sex attractant for various types of moths and cockroaches, and an alert signal for a variety of ants.
Undecane, also known as ch3-[ch2]9-ch3 or hendekan, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, undecane is considered to be a hydrocarbon lipid molecule. Undecane can be found in cardamom, which makes undecane a potential biomarker for the consumption of this food product. Undecane can be found primarily in feces, saliva, and urine. Undecane may also be used as an internal standard in gas chromatography when working with other hydrocarbons. Since the boiling point of undecane (196 °C) is well known, it may be used as a comparison for retention times in a gas chromatograph for molecules whose structure has been freshly elucidated. For example, if one is working with a 50 m crosslinked methyl silicone capillary column with an oven temperature increasing slowly, beginning around 60 °C, an 11-carbon molecule like undecane may be used as an internal standard to be compared with the retention times of other 10-, 11-, or 12- carbon molecules, depending on their structures .

同义名列表

8 个代谢物同义名

CH3-[CH2]9-CH3; N-Undecane; 2-Undecane; Hendecane; Hendekan; Undecane; Undekan; Undecane



数据库引用编号

14 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)

216 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

  • Muhammad Imran, Arshad Iqbal, Syed Lal Badshah, Ayaz Ali Sher, Hammad Ullah, Muhammad Ayaz, Osama F Mosa, Nada M Mostafa, Maria Daglia. Chemical and Nutritional Profiling of the Seaweed Dictyota dichotoma and Evaluation of Its Antioxidant, Antimicrobial and Hypoglycemic Potentials. Marine drugs. 2023 Apr; 21(5):. doi: 10.3390/md21050273. [PMID: 37233467]
  • Dabin Choi, Wesuk Kang, Taesun Park. Anti-Allergic and Anti-Inflammatory Effects of Undecane on Mast Cells and Keratinocytes. Molecules (Basel, Switzerland). 2020 Mar; 25(7):. doi: 10.3390/molecules25071554. [PMID: 32231089]
  • Guo-Fei Qin, Hong-Bao Liang, Wen-Xiu Liu, Feng Zhu, Ping-Lin Li, Guo-Qiang Li, Jing-Chun Yao. Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses. Molecules (Basel, Switzerland). 2019 Oct; 24(21):. doi: 10.3390/molecules24213912. [PMID: 31671644]
  • Nawroz Abdul-Razzak Tahir, Hoshyar Abdullah Azeez, Kadhm Abdullah Muhammad, Shewa Anwer Faqe, Dlshad Ali Omer. Exploring of bioactive compounds in essential oil acquired from the stem and root derivatives of Hypericum triquetrifolium callus cultures. Natural product research. 2019 May; 33(10):1504-1508. doi: 10.1080/14786419.2017.1419228. [PMID: 29277112]
  • Lei Yin, Kevin Shengyang Yu, Kun Lu, Xiaozhong Yu. Benzyl butyl phthalate promotes adipogenesis in 3T3-L1 preadipocytes: A High Content Cellomics and metabolomic analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2016 Apr; 32(?):297-309. doi: 10.1016/j.tiv.2016.01.010. [PMID: 26820058]
  • Yi-Ming Shi, Song-Liang Cai, Xiao-Nian Li, Miao Liu, Shan-Zhai Shang, Xue Du, Wei-Lie Xiao, Jian-Xin Pu, Han-Dong Sun. LC-UV-Guided Isolation and Structure Determination of Lancolide E: A Nortriterpenoid with a Tetracyclo[5.4.0.0(2,4).0(3,7)]undecane-Bridged System from a 'Talented' Schisandra Plant. Organic letters. 2016 Jan; 18(1):100-3. doi: 10.1021/acs.orglett.5b03334. [PMID: 26673855]
  • Yuko Kato, Nobuhiro Fuchi, Yutaka Nishimura, Ayano Watanabe, Mai Yagi, Yasuhito Nakadera, Eriko Higashi, Masateru Yamada, Takumi Aoki, Hideo Kigoshi. Discovery of 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating of chronic kidney diseases. Bioorganic & medicinal chemistry letters. 2014 Jan; 24(2):565-70. doi: 10.1016/j.bmcl.2013.12.020. [PMID: 24373724]
  • Yi-Ming Shi, Xin-Bo Wang, Xiao-Nian Li, Xiao Luo, Zi-Ying Shen, Yi-Ping Wang, Wei-Lie Xiao, Han-Dong Sun. Lancolides, antiplatelet aggregation nortriterpenoids with tricyclo[6.3.0.0(2,11)]undecane-bridged system from Schisandra lancifolia. Organic letters. 2013 Oct; 15(19):5068-71. doi: 10.1021/ol402414z. [PMID: 24059675]
  • Aleksandra Dorđević, Jelena Lazarević, Andrija Smelcerović, Gordana Stojanović. The case of Hypericum rochelii Griseb. & Schenk and Hypericum umbellatum A. Kern. essential oils: chemical composition and antimicrobial activity. Journal of pharmaceutical and biomedical analysis. 2013 Apr; 77(?):145-8. doi: 10.1016/j.jpba.2013.01.024. [PMID: 23416368]
  • Niko S Radulović, Polina D Blagojević. Chemical composition of Hypericum rumeliacum Boiss. essential oil. A new chemotype of this pharmacologically valuable species?. Chemistry & biodiversity. 2012 Oct; 9(10):2324-41. doi: 10.1002/cbdv.201200139. [PMID: 23081930]
  • Urszula Kotowska, Maciej Żalikowski, Valery A Isidorov. HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge. Environmental monitoring and assessment. 2012 May; 184(5):2893-907. doi: 10.1007/s10661-011-2158-8. [PMID: 21688031]
  • P A Olounladé, E V B Azando, M S Hounzangbé-Adoté, T B Tam Ha, E Leroy, C Moulis, N Fabre, J F Magnaval, H Hoste, A Valentin. In vitro anthelmintic activity of the essential oils of Zanthoxylum zanthoxyloides and Newbouldia laevis against Strongyloides ratti. Parasitology research. 2012 Apr; 110(4):1427-33. doi: 10.1007/s00436-011-2645-4. [PMID: 21960378]
  • Aline S Borer, Paul Wassmann, Margit Schmidt, Donald R Hoffman, Jing-Jiang Zhou, Christine Wright, Tilman Schirmer, Zora Marković-Housley. Crystal structure of Sol I 2: a major allergen from fire ant venom. Journal of molecular biology. 2012 Jan; 415(4):635-48. doi: 10.1016/j.jmb.2011.10.009. [PMID: 22100449]
  • Jiao Yin, Honglin Feng, Hongyan Sun, Jinghui Xi, Yazhong Cao, Kebin Li. Functional analysis of general odorant binding protein 2 from the meadow moth, Loxostege sticticalis L. (Lepidoptera: Pyralidae). PloS one. 2012; 7(3):e33589. doi: 10.1371/journal.pone.0033589. [PMID: 22479417]
  • David J Gonthier. Do herbivores eavesdrop on ant chemical communication to avoid predation?. PloS one. 2012; 7(1):e28703. doi: 10.1371/journal.pone.0028703. [PMID: 22235248]
  • Margarita Delgado-Rodríguez, Mercedes Ruiz-Montoya, Inmaculada Giraldez, Rafael López, Engracia Madejón, Manuel Jesús Díaz. Influence of control parameters in VOCs evolution during MSW trimming residues composting. Journal of agricultural and food chemistry. 2011 Dec; 59(24):13035-42. doi: 10.1021/jf2036017. [PMID: 22060272]
  • Iman Elidrisi, Saeedeh Negin, Pralav V Bhatt, Thavendran Govender, Hendrick G Kruger, George W Gokel, Glenn E M Maguire. Pore formation in phospholipid bilayers by amphiphilic cavitands. Organic & biomolecular chemistry. 2011 Jun; 9(12):4498-506. doi: 10.1039/c0ob01236j. [PMID: 21509358]
  • Lay-Jing Seow, Hooi-Kheng Beh, Amin Malik Shah Abdul Majid, Vikneswaran Murugaiyah, Norhayati Ismail, Mohd Zaini Asmawi. Anti-angiogenic activity of Gynura segetum leaf extracts and its fractions. Journal of ethnopharmacology. 2011 Mar; 134(2):221-7. doi: 10.1016/j.jep.2010.12.007. [PMID: 21167271]
  • Hamzeh Al Zabadi, Luc Ferrari, Irène Sari-Minodier, Marie-Aude Kerautret, Aziz Tiberguent, Christophe Paris, Denis Zmirou-Navier. Integrated exposure assessment of sewage workers to genotoxicants: an urinary biomarker approach and oxidative stress evaluation. Environmental health : a global access science source. 2011 Mar; 10(?):23. doi: 10.1186/1476-069x-10-23. [PMID: 21435260]
  • Carlo Bicchi, Manuela Rosanna Ruosi, Cecilia Cagliero, Chiara Cordero, Erica Liberto, Patrizia Rubiolo, Barbara Sgorbini. Quantitative analysis of volatiles from solid matrices of vegetable origin by high concentration capacity headspace techniques: determination of furan in roasted coffee. Journal of chromatography. A. 2011 Feb; 1218(6):753-62. doi: 10.1016/j.chroma.2010.12.002. [PMID: 21196009]
  • Chaozhan Wang, Ute Neugebauer, Jochen Bürck, Matti Myllykoski, Peter Baumgärtel, Jürgen Popp, Petri Kursula. Charge isomers of myelin basic protein: structure and interactions with membranes, nucleotide analogues, and calmodulin. PloS one. 2011; 6(5):e19915. doi: 10.1371/journal.pone.0019915. [PMID: 21647440]
  • Raphael T Tremblay, Sheppard A Martin, Jeffrey W Fisher. Metabolites from inhalation of aerosolized S-8 synthetic jet fuel in rats. Inhalation toxicology. 2011 Jan; 23(1):11-6. doi: 10.3109/08958378.2010.535573. [PMID: 21222558]
  • Samuel D Banister, Iman A Moussa, Corinne Beinat, Aaron J Reynolds, Paolo Schiavini, William T Jorgensen, Michael Kassiou. Trishomocubane as a scaffold for the development of selective dopamine transporter (DAT) ligands. Bioorganic & medicinal chemistry letters. 2011 Jan; 21(1):38-41. doi: 10.1016/j.bmcl.2010.11.075. [PMID: 21146989]
  • Mohammed El Amine Dib, Nassim Djabou, Jean-Marie Desjobert, Houcine Allali, Boufeldja Tabti, Alain Muselli, Jean Costa. Characterization of volatile compounds of Daucus crinitus Desf. Headspace Solid Phase Microextraction as alternative technique to Hydrodistillation. Chemistry Central journal. 2010 Sep; 4(?):16. doi: 10.1186/1752-153x-4-16. [PMID: 20858266]
  • Ill-Min Chung, Su-Hyun Seo, Eun-Young Kang, Won-Hwan Park, Hyung-In Moon. Larvicidal effects of the major essential oil of Pittosporum tobira against Aedes aegypti (L.). Journal of enzyme inhibition and medicinal chemistry. 2010 Jun; 25(3):391-3. doi: 10.3109/14756360903185952. [PMID: 19874194]
  • Rebecca M Lennen, Drew J Braden, Ryan A West, James A Dumesic, Brian F Pfleger. A process for microbial hydrocarbon synthesis: Overproduction of fatty acids in Escherichia coli and catalytic conversion to alkanes. Biotechnology and bioengineering. 2010 Jun; 106(2):193-202. doi: 10.1002/bit.22660. [PMID: 20073090]
  • Daniel Bourdeaux, Valérie Sautou-Miranda, Agnès Montagner, Sébastien Perbet, Jean Michel Constantin, Jean-Etienne Bazin, Jean Chopineau. Simple assay of plasma sevoflurane and its metabolite hexafluoroisopropanol by headspace GC-MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jan; 878(1):45-50. doi: 10.1016/j.jchromb.2009.11.018. [PMID: 19948429]
  • Oluseye K Onajole, Karnishree Govender, Patrick Govender, Paul D van Helden, Hendrik G Kruger, Glenn E M Maguire, Karen Muthusamy, Manormoney Pillay, Ian Wiid, Thavendran Govender. Pentacyclo-undecane derived cyclic tetra-amines: synthesis and evaluation as potent anti-tuberculosis agents. European journal of medicinal chemistry. 2009 Nov; 44(11):4297-305. doi: 10.1016/j.ejmech.2009.07.015. [PMID: 19679378]
  • Rose N Kigathi, Sybille B Unsicker, Michael Reichelt, Jürgen Kesselmeier, Jonathan Gershenzon, Wolfgang W Weisser. Emission of volatile organic compounds after herbivory from Trifolium pratense (L.) under laboratory and field conditions. Journal of chemical ecology. 2009 Nov; 35(11):1335-48. doi: 10.1007/s10886-009-9716-3. [PMID: 20013039]
  • Mohamed L Ashour, Mahmoud El-Readi, Mahmoud Youns, Sri Mulyaningsih, Frank Sporer, Thomas Efferth, Michael Wink. Chemical composition and biological activity of the essential oil obtained from Bupleurum marginatum (Apiaceae). The Journal of pharmacy and pharmacology. 2009 Aug; 61(8):1079-87. doi: 10.1211/jpp/61.08.0012. [PMID: 19703352]
  • Karla J Medina-Ortega, Nilsa A Bosque-Pérez, Esther Ngumbi, Edgardo S Jiménez-Martínez, Sanford D Eigenbrode. Rhopalosiphum padi (Hemiptera: Aphididae) responses to volatile cues from Barley yellow dwarf virus-infected wheat. Environmental entomology. 2009 Jun; 38(3):836-45. doi: 10.1603/022.038.0337. [PMID: 19508794]
  • Tomás Hendrych, Marie Kodedová, Karel Sigler, Dana Gásková. Characterization of the kinetics and mechanisms of inhibition of drugs interacting with the S. cerevisiae multidrug resistance pumps Pdr5p and Snq2p. Biochimica et biophysica acta. 2009 Mar; 1788(3):717-23. doi: 10.1016/j.bbamem.2008.12.001. [PMID: 19111673]
  • Gary A Strobel, Berk Knighton, Katreena Kluck, Yuhao Ren, Tom Livinghouse, Meghan Griffin, Daniel Spakowicz, Joe Sears. The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072). Microbiology (Reading, England). 2008 Nov; 154(Pt 11):3319-3328. doi: 10.1099/mic.0.2008/022186-0. [PMID: 18957585]
  • Jae-Hwan Kwak, Hae-Eun Kang, Jae-Kyung Jung, Hwajung Kim, Jungsook Cho, Heesoon Lee. Synthesis of 7-hydroxy-4-oxo-4H-chromene- and 7-hydroxychroman-2-carboxylic acid N-alkyl amides and their antioxidant activities. Archives of pharmacal research. 2006 Sep; 29(9):728-34. doi: 10.1007/bf02974071. [PMID: 17024844]
  • Pamela R D Williams, Jacqueline Patterson, Daniel W Briggs. VCCEP pilot: progress on evaluating children's risks and data needs. Risk analysis : an official publication of the Society for Risk Analysis. 2006 Jun; 26(3):781-801. doi: 10.1111/j.1539-6924.2006.00766.x. [PMID: 16834634]
  • F Muhammad, N A Monteiro-Riviere, R E Baynes, J E Riviere. Effect of in vivo jet fuel exposure on subsequent in vitro dermal absorption of individual aromatic and aliphatic hydrocarbon fuel constituents. Journal of toxicology and environmental health. Part A. 2005 May; 68(9):719-37. doi: 10.1080/15287390590925456. [PMID: 16020199]
  • F Muhammad, N A Monteiro-Riviere, J E Riviere. Comparative in vivo toxicity of topical JP-8 jet fuel and its individual hydrocarbon components: identification of tridecane and tetradecane as key constituents responsible for dermal irritation. Toxicologic pathology. 2005; 33(2):258-66. doi: 10.1080/01926230590908222. [PMID: 15902969]
  • A Q Smith, J L Campbell, D A Keys, J W Fisher. Rat tissue and blood partition coefficients for n-alkanes (C8 to C12). International journal of toxicology. 2005 Jan; 24(1):35-41. doi: 10.1080/10915810590918698. [PMID: 15981738]
  • Yinan Wei, Huilin Li, Dax Fu. Oligomeric state of the Escherichia coli metal transporter YiiP. The Journal of biological chemistry. 2004 Sep; 279(38):39251-9. doi: 10.1074/jbc.m407044200. [PMID: 15258151]
  • J Trocewicz. Urine sample preparation of tricyclic antidepressants by means of a supported liquid membrane technique for high-performance liquid chromatographic analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 801(2):213-20. doi: 10.1016/j.jchromb.2003.11.013. [PMID: 14751789]
  • Anna Krasowska, Lucyna Chmielewska, Ryszard Adamski, Jacek Luczyński, Stanisław Witek, Karel Sigler. The sensitivity of yeast and yeast-like cells to new lysosomotropic agents. Cellular & molecular biology letters. 2004; 9(4A):675-83. doi: NULL. [PMID: 15647790]
  • Yoshinori Mine, Prithy Rupa. Genetic attachment of undecane peptides to ovomucoid third domain can suppress the production of specific IgG and IgE antibodies. Biochemical and biophysical research communications. 2003 Nov; 311(1):223-8. doi: 10.1016/j.bbrc.2003.09.201. [PMID: 14575717]
  • Wha Bin Im, Christopher L Chio, Glen L Alberts, Dac M Dinh. Positive allosteric modulator of the human 5-HT2C receptor. Molecular pharmacology. 2003 Jul; 64(1):78-84. doi: 10.1124/mol.64.1.78. [PMID: 12815163]
  • Baoyu Han, Zongmao Chen. Behavioral and electrophysiological responses of natural enemies to synomones from tea shoots and kairomones from tea aphids, Toxoptera aurantii. Journal of chemical ecology. 2002 Nov; 28(11):2203-19. doi: 10.1023/a:1021045231501. [PMID: 12523563]
  • Sung Han Kim, Sang Jun Lee, Joo Hyoung Lee, Won Suck Sun, Jung Han Kim. Antimicrobial activity of 9-O-acyl- and 9-O-alkylberberrubine derivatives. Planta medica. 2002 Mar; 68(3):277-81. doi: 10.1055/s-2002-23128. [PMID: 11914971]
  • K R Kumar, G Archunan, R Jeyaraman, S Narasimhan. Chemical characterization of bovine urine with special reference to oestrus. Veterinary research communications. 2000 Nov; 24(7):445-54. doi: 10.1023/a:1006495404407. [PMID: 11085464]
  • L Giuliani, G Carmignani, E Belgrano, P Puppo. Transcatheter arterial embolization in urological tumors: the use of isobutyl-2-cyanoacrylate. The Journal of urology. 1979 May; 121(5):630-4. doi: 10.1016/s0022-5347(17)56913-x. [PMID: 439260]
  • A C Buck. Disorders of micturition in bacterial prostatitis. Proceedings of the Royal Society of Medicine. 1975 Aug; 68(8):508-11. doi: NULL. [PMID: 681]