UNDECANOIC ACID (BioDeep_00000400545)

Main id: BioDeep_00000002179

Secondary id: BioDeep_00000229668, BioDeep_00000398033, BioDeep_00000859545

PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds natural product


代谢物信息卡片


UNDECANOIC ACID

化学式: C11H22O2 (186.1619712)
中文名称: 十一酸, 十一烷酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.13%

分子结构信息

SMILES: CCCCCCCCCCC(=O)O
InChI: InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)

描述信息

A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.
C254 - Anti-Infective Agent > C514 - Antifungal Agent
Undecanoic acid (Undecanoate) is a monocarboxylic acid with antimycotic property, which inhibits the production of exocellular keratinase, lipase and the biosynthesis of several phospholipids in T. rubrum[1].
Undecanoic acid (Undecanoate) is a monocarboxylic acid with antimycotic property, which inhibits the production of exocellular keratinase, lipase and the biosynthesis of several phospholipids in T. rubrum[1].

同义名列表

5 个代谢物同义名

UNDECANOIC ACID; Undecanoate; Hendecanoic acid; Undecanoic acid; Undecanoic acid



数据库引用编号

23 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)

94 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

  • Marek Tatarko, Sandro Spagnolo, Martin Csiba, Veronika Šubjaková, Tibor Hianik. Analysis of the Interaction between DNA Aptamers and Cytochrome C on the Surface of Lipid Films and on the MUA Monolayer: A QCM-D Study. Biosensors. 2023 Feb; 13(2):. doi: 10.3390/bios13020251. [PMID: 36832017]
  • Antonio Rossi, Maíra P Martins, Tamires A Bitencourt, Nalu T A Peres, Carlos H L Rocha, Flaviane M G Rocha, João Neves-da-Rocha, Marcos E R Lopes, Pablo R Sanches, Júlio C Bortolossi, Nilce M Martinez-Rossi. Reassessing the Use of Undecanoic Acid as a Therapeutic Strategy for Treating Fungal Infections. Mycopathologia. 2021 Jun; 186(3):327-340. doi: 10.1007/s11046-021-00550-4. [PMID: 33835367]
  • Lin-Hai Chen, Qing Zhang, Xin Xie, Fa-Jun Nan. Modulation of the G-Protein-Coupled Receptor 84 (GPR84) by Agonists and Antagonists. Journal of medicinal chemistry. 2020 12; 63(24):15399-15409. doi: 10.1021/acs.jmedchem.0c01378. [PMID: 33267584]
  • Meryem Köse, Thanigaimalai Pillaiyar, Vigneshwaran Namasivayam, Elisabetta De Filippo, Katharina Sylvester, Trond Ulven, Ivar von Kügelgen, Christa E Müller. An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights. Journal of medicinal chemistry. 2020 03; 63(5):2391-2410. doi: 10.1021/acs.jmedchem.9b01339. [PMID: 31721581]
  • Niege S Mendes, Tamires A Bitencourt, Pablo R Sanches, Rafael Silva-Rocha, Nilce M Martinez-Rossi, Antonio Rossi. Transcriptome-wide survey of gene expression changes and alternative splicing in Trichophyton rubrum in response to undecanoic acid. Scientific reports. 2018 02; 8(1):2520. doi: 10.1038/s41598-018-20738-x. [PMID: 29410524]
  • Qiaoyan Huang, Dong Feng, Kai Liu, Peng Wang, Hongyan Xiao, Ying Wang, Shicui Zhang, Zhenhui Liu. A medium-chain fatty acid receptor Gpr84 in zebrafish: expression pattern and roles in immune regulation. Developmental and comparative immunology. 2014 Aug; 45(2):252-8. doi: 10.1016/j.dci.2014.03.017. [PMID: 24704214]
  • Michael T L Casford, Aimin Ge, Peter J N Kett, Shen Ye, Paul B Davies. The structure of lipid bilayers adsorbed on activated carboxy-terminated monolayers investigated by sum frequency generation spectroscopy. The journal of physical chemistry. B. 2014 Mar; 118(12):3335-45. doi: 10.1021/jp410401z. [PMID: 24628457]
  • Amarpreet Chahal, Carlos M Monreal, John Bissett, Owen Rowland, Myron L Smith, S Shea Miller. Metabolism of n-C10:0 and n-C11:0 fatty acids by Trichoderma koningii, Penicillium janthinellum and their mixed culture: I. Biomass and CO2 production, and allocation of intracellular lipids. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2014; 49(12):945-54. doi: 10.1080/03601234.2014.951581. [PMID: 25310810]
  • Carlos M Monreal, Amarpreet Chahal, Owen Rowland, Myron Smith, Morris Schnitzer. Metabolism of nC11 fatty acid fed to Trichoderma koningii and Penicillium janthinellum II: Production of intracellular and extracellular lipids. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2014; 49(12):955-65. doi: 10.1080/03601234.2014.951583. [PMID: 25310811]
  • Haixun Guo, Helen Hathaway, Melanie E Royce, Eric R Prossnitz, Yubin Miao. Influences of hydrocarbon linkers on the receptor binding affinities of gonadotropin-releasing hormone peptides. Bioorganic & medicinal chemistry letters. 2013 Oct; 23(20):5484-7. doi: 10.1016/j.bmcl.2013.08.075. [PMID: 24018188]
  • Jing Jin, Jiping Chen, Yuzeng Tian, Lili Zou, Longxing Wang, Fang Li. [Determination of undecanoic acid and 13-methyl-tetradecanoic acid connected to the glyceride with internal standard method and its application to the identification of adulteration of illegal cooking oil]. Se pu = Chinese journal of chromatography. 2013 Jun; 31(6):556-60. doi: 10.3724/sp.j.1123.2012.12036. [PMID: 24063195]
  • Smritilekha Bera, Ramesh Dhondikubeer, Brandon Findlay, George G Zhanel, Frank Schweizer. Synthesis and antibacterial activities of amphiphilic neomycin B-based bilipid conjugates and fluorinated neomycin B-based lipids. Molecules (Basel, Switzerland). 2012 Aug; 17(8):9129-41. doi: 10.3390/molecules17089129. [PMID: 22858839]
  • Anthony Y Yin, Michelle Htun, Ronald S Swerdloff, Maruja Diaz-Arjonilla, Robert E Dudley, Sandra Faulkner, Rachelle Bross, Andrew Leung, Sima Baravarian, Laura Hull, James A Longstreth, Steven Kulback, Gregory Flippo, Christina Wang. Reexamination of pharmacokinetics of oral testosterone undecanoate in hypogonadal men with a new self-emulsifying formulation. Journal of andrology. 2012 Mar; 33(2):190-201. doi: 10.2164/jandrol.111.013169. [PMID: 21474786]
  • Ranabir Salam, Achouba Singh Kshetrimayum, Reetu Keisam. Testosterone and metabolic syndrome: The link. Indian journal of endocrinology and metabolism. 2012 Mar; 16 Suppl 1(?):S12-9. doi: 10.4103/2230-8210.94248. [PMID: 22701831]
  • Yu Wang, Zhipu Luo, Xiaoli Shi, Huan Wang, Lei Nie, Mingdong Huang. A fluorescent fatty acid probe, DAUDA, selectively displaces two myristates bound in human serum albumin. Protein science : a publication of the Protein Society. 2011 Dec; 20(12):2095-101. doi: 10.1002/pro.749. [PMID: 21997768]
  • Barbara J Attardi, Jean A Engbring, David Gropp, Sheri Ann Hild. Development of dimethandrolone 17beta-undecanoate (DMAU) as an oral male hormonal contraceptive: induction of infertility and recovery of fertility in adult male rabbits. Journal of andrology. 2011 Sep; 32(5):530-40. doi: 10.2164/jandrol.110.011817. [PMID: 21164142]
  • Fuyuan Jing, David C Cantu, Jarmila Tvaruzkova, Jay P Chipman, Basil J Nikolau, Marna D Yandeau-Nelson, Peter J Reilly. Phylogenetic and experimental characterization of an acyl-ACP thioesterase family reveals significant diversity in enzymatic specificity and activity. BMC biochemistry. 2011 Aug; 12(?):44. doi: 10.1186/1471-2091-12-44. [PMID: 21831316]
  • Subramani Palani, Sundararajan Raja, Ramanujam Praveen Kumar, Ranganathan Selvaraj, Balasubramanian Senthil Kumar. Evaluation of phytoconstituents and anti-nephrotoxic and antioxidant activities of Monochoria vaginalis. Pakistan journal of pharmaceutical sciences. 2011 Jul; 24(3):293-301. doi: . [PMID: 21715262]
  • Amit Kumar, Rebekah L Bullard, Pritesh Patel, Lea C Paslay, Dipti Singh, Ewa A Bienkiewicz, Sarah E Morgan, Vijayaraghavan Rangachari. Non-esterified fatty acids generate distinct low-molecular weight amyloid-β (Aβ42) oligomers along pathway different from fibril formation. PloS one. 2011 Apr; 6(4):e18759. doi: 10.1371/journal.pone.0018759. [PMID: 21526230]
  • V A Giagulli, V Triggiani, G Corona, D Carbone, B Licchelli, E Tafaro, F Resta, C Sabbà, M Maggi, E Guastamacchia. Evidence-based medicine update on testosterone replacement therapy (TRT) in male hypogonadism: focus on new formulations. Current pharmaceutical design. 2011; 17(15):1500-11. doi: 10.2174/138161211796197160. [PMID: 21521164]
  • Jan Willmann, Herbert Thiele, Dieter Leibfritz. Combined reversed phase HPLC, mass spectrometry, and NMR spectroscopy for a fast separation and efficient identification of phosphatidylcholines. Journal of biomedicine & biotechnology. 2011; 2011(?):. doi: 10.1155/2011/385786. [PMID: 20871812]
  • Svetlana Y Kalinchenko, Yuliya A Tishova, George J Mskhalaya, Louis J G Gooren, Erik J Giltay, Farid Saad. Effects of testosterone supplementation on markers of the metabolic syndrome and inflammation in hypogonadal men with the metabolic syndrome: the double-blinded placebo-controlled Moscow study. Clinical endocrinology. 2010 Nov; 73(5):602-12. doi: 10.1111/j.1365-2265.2010.03845.x. [PMID: 20718771]
  • Yunbao Liu, Muraleedharan G Nair. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products. 2010 Jul; 73(7):1193-5. doi: 10.1021/np1000945. [PMID: 20565070]
  • Alessandra Cornoldi, Giuseppe Caminiti, Giuseppe Marazzi, Cristiana Vitale, Roberto Patrizi, Maurizio Volterrani, Marco Miceli, Massimo Fini, Giovanni Spera, Giuseppe Rosano. Effects of chronic testosterone administration on myocardial ischemia, lipid metabolism and insulin resistance in elderly male diabetic patients with coronary artery disease. International journal of cardiology. 2010 Jun; 142(1):50-5. doi: 10.1016/j.ijcard.2008.12.107. [PMID: 19361872]
  • Sheng Lin, Zhongxiao Zhanf, Yunheng Shen, Huiliang Li, Lei Shan, Runhui Liu, Xike Xu, Weidong Zhanf. [Ethyl acetate-soluble chemical constituents from whole plants of Senecio chrysanthemoides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 May; 35(9):1137-41. doi: 10.4268/cjcmm20100911. [PMID: 20707068]
  • Alvaro Morales, Angela Black, Laurel Emerson, Jack Barkin, Irwin Kuzmarov, Andrew Day. Androgens and sexual function: a placebo-controlled, randomized, double-blind study of testosterone vs. dehydroepiandrosterone in men with sexual dysfunction and androgen deficiency. The aging male : the official journal of the International Society for the Study of the Aging Male. 2009 Dec; 12(4):104-12. doi: 10.3109/13685530903294388. [PMID: 19883295]
  • 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]
  • 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]
  • Christian Abel, Maria Clauss, Andrea Schaub, Jonathan Gershenzon, Dorothea Tholl. Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana. Planta. 2009 Jun; 230(1):1-11. doi: 10.1007/s00425-009-0921-7. [PMID: 19322583]
  • L J Gooren, F Saad, A Haide, A Yassin. Decline of plasma 5alpha-dihydrotestosterone (DHT) levels upon testosterone administration to elderly men with subnormal plasma testosterone and high DHT levels. Andrologia. 2008 Oct; 40(5):298-302. doi: 10.1111/j.1439-0272.2008.00857.x. [PMID: 18811920]
  • Maria Cristina Meriggiola, Francesca Armillotta, Antonietta Costantino, Paola Altieri, Farid Saad, Thomas Kalhorn, Anna Myriam Perrone, Tullio Ghi, Carlotta Pelusi, Giuseppe Pelusi. Effects of testosterone undecanoate administered alone or in combination with letrozole or dutasteride in female to male transsexuals. The journal of sexual medicine. 2008 Oct; 5(10):2442-53. doi: 10.1111/j.1743-6109.2008.00909.x. [PMID: 18624972]
  • P Anielski. Hair analysis of anabolic steroids in connection with doping control-results from horse samples. Journal of mass spectrometry : JMS. 2008 Jul; 43(7):1001-8. doi: 10.1002/jms.1446. [PMID: 18563854]
  • Carolyn M Webb, Andrew G Elkington, Mustafa M Kraidly, Niall Keenan, Dudley J Pennell, Peter Collins. Effects of oral testosterone treatment on myocardial perfusion and vascular function in men with low plasma testosterone and coronary heart disease. The American journal of cardiology. 2008 Mar; 101(5):618-24. doi: 10.1016/j.amjcard.2007.09.114. [PMID: 18308009]
  • Farid Saad, Louis J Gooren, Ahmad Haider, Aksam Yassin. A dose-response study of testosterone on sexual dysfunction and features of the metabolic syndrome using testosterone gel and parenteral testosterone undecanoate. Journal of andrology. 2008 Jan; 29(1):102-5. doi: 10.2164/jandrol.107.002774. [PMID: 17916569]
  • Ying-Li Lu, Lin Kuang, Hui Zhu, Hui Wu, Xue-Fang Wang, Yu-Ping Pang, Ning-Jian Wang, Dan-Lu Yu. Changes in aortic endothelium ultrastructure in male rats following castration, replacement with testosterone and administration of 5alpha-reductase inhibitor. Asian journal of andrology. 2007 Nov; 9(6):843-7. doi: 10.1111/j.1745-7262.2007.00327.x. [PMID: 17968472]
  • Eric D Kaufman, Jennifer Belyea, Marcus C Johnson, Zach M Nicholson, Jennifer L Ricks, Pavak K Shah, Michael Bayless, Torbjörn Pettersson, Zsombor Feldotö, Eva Blomberg, Per Claesson, Stefan Franzen. Probing protein adsorption onto mercaptoundecanoic acid stabilized gold nanoparticles and surfaces by quartz crystal microbalance and zeta-potential measurements. Langmuir : the ACS journal of surfaces and colloids. 2007 May; 23(11):6053-62. doi: 10.1021/la063725a. [PMID: 17465581]
  • Farid Saad, Axel Kamischke, Aksam Yassin, Michael Zitzmann, Markus Schubert, Friedrich Jockenhel, Hermann M Behre, Louis Gooren, Eberhard Nieschlag. More than eight years' hands-on experience with the novel long-acting parenteral testosterone undecanoate. Asian journal of andrology. 2007 May; 9(3):291-7. doi: 10.1111/j.1745-7262.2007.00275.x. [PMID: 17486268]
  • Aksam A Yassin, Mohamed Haffejee. Testosterone depot injection in male hypogonadism: a critical appraisal. Clinical interventions in aging. 2007; 2(4):577-90. doi: NULL. [PMID: 18225458]
  • Muhammad Ishtiaq Ch, Yang F Wen, YiYu Cheng. Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. Journal of AOAC International. 2007 Jan; 90(1):60-7. doi: . [PMID: 17373437]
  • Heliana C Salles, Evelyn Cristina F R Volsi, Maurício R Marques, Bibiana M Souza, Lucilene D dos Santos, Cláudio F Tormena, Maria A Mendes, Mario S Palma. The venomous secrets of the web droplets from the viscid spiral of the orb-weaver spider Nephila clavipes (Araneae, Tetragnatidae). Chemistry & biodiversity. 2006 Jul; 3(7):727-41. doi: 10.1002/cbdv.200690075. [PMID: 17193305]
  • Bradley D Anawalt, John K Amory, Karen L Herbst, Andrea D Coviello, Stephanie T Page, William J Bremner, Alvin M Matsumoto. Intramuscular testosterone enanthate plus very low dosage oral levonorgestrel suppresses spermatogenesis without causing weight gain in normal young men: a randomized clinical trial. Journal of andrology. 2005 May; 26(3):405-13. doi: 10.2164/jandrol.04135. [PMID: 15867009]
  • Keerthi S Guruge, Sachi Taniyasu, Nobuyoshi Yamashita, Sumedha Wijeratna, Keerthi M Mohotti, Harsha R Seneviratne, Kurunthachalam Kannan, Noriko Yamanaka, Shigeru Miyazaki. Perfluorinated organic compounds in human blood serum and seminal plasma: a study of urban and rural tea worker populations in Sri Lanka. Journal of environmental monitoring : JEM. 2005 Apr; 7(4):371-7. doi: 10.1039/b412532k. [PMID: 15798805]
  • Matthew Haren, Ian Chapman, Penelope Coates, John Morley, Gary Wittert. Effect of 12 month oral testosterone on testosterone deficiency symptoms in symptomatic elderly males with low-normal gonadal status. Age and ageing. 2005 Mar; 34(2):125-30. doi: 10.1093/ageing/afi003. [PMID: 15596419]
  • Yu-Chang Tyan, Jiunn-Der Liao, Shiang-Bin Jong, Pao-Chi Liao, Ming-Hui Yang, Yin-Wei Chang, Ruth Klauser, Michael Himmelhaus, Michael Grunze. Characterization of trypsin immobilized on the functionable alkylthiolate self-assembled monolayers: a preliminary application for trypsin digestion chip on protein identification using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Journal of materials science. Materials in medicine. 2005 Feb; 16(2):135-42. doi: 10.1007/s10856-005-5987-6. [PMID: 15744601]
  • M Schubert, T Minnemann, D Hübler, D Rouskova, A Christoph, M Oettel, M Ernst, U Mellinger, W Krone, F Jockenhövel. Intramuscular testosterone undecanoate: pharmacokinetic aspects of a novel testosterone formulation during long-term treatment of men with hypogonadism. The Journal of clinical endocrinology and metabolism. 2004 Nov; 89(11):5429-34. doi: 10.1210/jc.2004-0897. [PMID: 15531493]
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