Caprate (10:0) (BioDeep_00000002198)

 

Secondary id: BioDeep_00000229630, BioDeep_00000400541, BioDeep_00000405291, BioDeep_00000860736

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product BioNovoGene_Lab2019


代谢物信息卡片


decanoic acid

化学式: C10H20O2 (172.14632200000003)
中文名称: 正癸酸, 癸酸, 癸酸(C10:0)
谱图信息: 最多检出来源 Homo sapiens(feces) 0.04%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Caprate (10:0). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/caprate_(10:0) (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000002198). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCCCC(=O)O
InChI: InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

描述信息

Capric acid, also known as decanoic acid is a C10 saturated fatty acid. It is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with a sweaty, unpleasant aroma that is reminiscent of goats. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid occurs naturally in coconut oil (about 10\\\\\\%) and palm kernel oil (about 4\\\\\\%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid, caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid) account for about 15\\\\\\% of the fatty acids in goat milk fat (PMID 16747831). Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, which may occur via PPARgamma receptor agonism and the targeting of genes involved in mitochondrial biogenesis (PMIDL 24383952).
Widespread in plant oils and as glycerides in seed oilsand is also present in apple, apricot, banana, morello cherry, citrus fruits, cheese, butter, white wine, Japanese whiskey, peated malt, wort and scallops. It is used as a defoamer, lubricant and citrus fruit coating. Salts (Na, K, Mg, Ca, Al) used as binders, emulsifiers and anticaking agents in food manuf. Decanoic acid is found in many foods, some of which are radish (variety), meatball, phyllo dough, and american shad.

Decanoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=334-48-5 (retrieved 2024-06-29) (CAS RN: 334-48-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].
Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].
Decanoic acid, a component of medium chain triclycerides, is a brain-penetrant and non-competitive inhibitor of AMPA receptor. Decanoic acid has antiseizure effects[1][2][3].

同义名列表

37 个代谢物同义名

Decanoic acid, sodium salt; 1-Nonanecarboxylic acid; 1-Nonanecarboxylate; Sodium decanoate; n-Decanoic acid; CH3-[CH2]8-COOH; Sodium caprate; N-Decylic acid; N-Capric acid; Decanoic acid; Caprynic acid; N-Decoic acid; Caprinic acid; Kaprinsaeure; Decylic acid; Lunac 10-95; N-Decanoate; Capric acid; Decoic acid; Dekansaeure; Lunac 10-98; Prifac 2906; N-Decylate; Prifac 296; Emery 659; N-Caprate; Caprinate; Decanoate; N-Decoate; Caprynate; FA(10:0); Decylate; Caprate; Decoate; C10:0; 10:0; Decanoic acid



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

37 个相关的代谢反应过程信息。

Reactome(28)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(9)

PharmGKB(0)

393 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

  • Shang Li, Junyu Zhai, Weiwei Chu, Xueying Geng, Dongshuang Wang, Luwei Jiao, Gang Lu, Wai-Yee Chan, Kang Sun, Yun Sun, Zi-Jiang Chen, Yanzhi Du. Alleviation of Limosilactobacillus reuteri in polycystic ovary syndrome protects against circadian dysrhythmia-induced dyslipidemia via capric acid and GALR1 signaling. NPJ biofilms and microbiomes. 2023 Jul; 9(1):47. doi: 10.1038/s41522-023-00415-2. [PMID: 37422471]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Huyen Tran, Eitaro Aihara, Faiz Ahmad Mohammed, Hongchang Qu, Andrew Riley, Yuan Su, Xianyin Lai, Siyuan Huang, Aktham Aburub, Jack Jia Hua Chen, Olivia Hope Vitale, Yanbin Lao, Selina Estwick, Zhonghua Qi, Mohamed E H ElSayed. In Vivo Mechanism of Action of Sodium Caprate for Improving the Intestinal Absorption of a GLP1/GIP Coagonist Peptide. Molecular pharmaceutics. 2023 02; 20(2):929-941. doi: 10.1021/acs.molpharmaceut.2c00443. [PMID: 36592951]
  • Cigdem Sahin, Lilia Magomedova, Thais A M Ferreira, Jiabao Liu, Jens Tiefenbach, Priscilla S Alves, Fellipe J G Queiroz, Andressa S de Oliveira, Mousumi Bhattacharyya, Julie Grouleff, Patrícia C N Nogueira, Edilberto R Silveira, Daniel C Moreira, José Roberto Souza de Almeida Leite, Guilherme D Brand, David Uehling, Gennady Poda, Henry Krause, Carolyn L Cummins, Luiz A S Romeiro. Phenolic Lipids Derived from Cashew Nut Shell Liquid to Treat Metabolic Diseases. Journal of medicinal chemistry. 2022 02; 65(3):1961-1978. doi: 10.1021/acs.jmedchem.1c01542. [PMID: 35089724]
  • Ruimin Miao, Fanqi Jin, Zhigao Wang, Weijia Lu, Junhong Liu, Xinyang Li, Rui Xue Zhang. Oral delivery of decanoic acid conjugated plant protein shell incorporating hybrid nanosystem leverage intestinal absorption of polyphenols. Biomaterials. 2022 02; 281(?):121373. doi: 10.1016/j.biomaterials.2022.121373. [PMID: 35063742]
  • Staffan Berg, Lillevi Kärrberg, Denny Suljovic, Frank Seeliger, Magnus Söderberg, Marta Perez-Alcazar, Natalie Van Zuydam, Bertil Abrahamsson, Andreas M Hugerth, Nigel Davies, Christel A S Bergström. Impact of Intestinal Concentration and Colloidal Structure on the Permeation-Enhancing Efficiency of Sodium Caprate in the Rat. Molecular pharmaceutics. 2022 01; 19(1):200-212. doi: 10.1021/acs.molpharmaceut.1c00724. [PMID: 34928160]
  • Rosita Kneiszl, Shakhawath Hossain, Per Larsson. In Silico-Based Experiments on Mechanistic Interactions between Several Intestinal Permeation Enhancers with a Lipid Bilayer Model. Molecular pharmaceutics. 2022 01; 19(1):124-137. doi: 10.1021/acs.molpharmaceut.1c00689. [PMID: 34913341]
  • Huijuan Zheng, Weilin Liu, Shuibing Yang. Carboxymethyl chitosan coated medium-chain fatty acid nanoliposomes: structure, composition, stability and in vitro release investigation. Food & function. 2021 Oct; 12(20):9947-9954. doi: 10.1039/d1fo01985f. [PMID: 34492679]
  • Julián Paul Martínez-Galán, Catalina María Ontibón-Echeverri, Mariana Campos Costa, Alexander Batista-Duharte, Vinicius Guerso Batista, Victoria Mesa, Rubens Monti, Ariela Veloso de Paula, Amanda Martins Baviera. Enzymatic synthesis of capric acid-rich structured lipids and their effects on mice with high-fat diet-induced obesity. Food research international (Ottawa, Ont.). 2021 10; 148(?):110602. doi: 10.1016/j.foodres.2021.110602. [PMID: 34507747]
  • Jens V Andersen, Emil W Westi, Emil Jakobsen, Nerea Urruticoechea, Karin Borges, Blanca I Aldana. Astrocyte metabolism of the medium-chain fatty acids octanoic acid and decanoic acid promotes GABA synthesis in neurons via elevated glutamine supply. Molecular brain. 2021 09; 14(1):132. doi: 10.1186/s13041-021-00842-2. [PMID: 34479615]
  • Jakub Suchodolski, Daria Derkacz, Przemysław Bernat, Anna Krasowska. Capric acid secreted by Saccharomyces boulardii influences the susceptibility of Candida albicans to fluconazole and amphotericin B. Scientific reports. 2021 03; 11(1):6519. doi: 10.1038/s41598-021-86012-9. [PMID: 33753842]
  • Witek Kwiatkowski, Radoslaw Bomba, Pavel Afanasyev, Daniel Boehringer, Roland Riek, Jason Greenwald. Prebiotic Peptide Synthesis and Spontaneous Amyloid Formation Inside a Proto-Cellular Compartment. Angewandte Chemie (International ed. in English). 2021 03; 60(10):5561-5568. doi: 10.1002/anie.202015352. [PMID: 33325627]
  • Xiumei Wang, Xiaoxu Zhao, Xiaoli Qin, Zexin Zhao, Bo Yang, Yonghua Wang. Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents. Journal of oleo science. 2021 Feb; 70(2):227-236. doi: 10.5650/jos.ess20200. [PMID: 33456003]
  • Partha Dabke, Graham Brogden, Hassan Y Naim, Anibh M Das. Ketogenic Diet: Impact on Cellular Lipids in Hippocampal Murine Neurons. Nutrients. 2020 Dec; 12(12):. doi: 10.3390/nu12123870. [PMID: 33352829]
  • Partha Dabke, Anibh M Das. Mechanism of Action of Ketogenic Diet Treatment: Impact of Decanoic Acid and Beta-Hydroxybutyrate on Sirtuins and Energy Metabolism in Hippocampal Murine Neurons. Nutrients. 2020 Aug; 12(8):. doi: 10.3390/nu12082379. [PMID: 32784510]
  • Mohamad Nasir Shafiee, Catharine A Ortori, David A Barrett, Nigel P Mongan, Jafaru Abu, William Atiomo. Lipidomic Biomarkers in Polycystic Ovary Syndrome and Endometrial Cancer. International journal of molecular sciences. 2020 Jul; 21(13):. doi: 10.3390/ijms21134753. [PMID: 32635401]
  • Caroline Twarog, Kai Liu, Peter J O'Brien, Kenneth A Dawson, Elias Fattal, Brigitte Illel, David J Brayden. A head-to-head Caco-2 assay comparison of the mechanisms of action of the intestinal permeation enhancers: SNAC and sodium caprate (C10). European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2020 Jul; 152(?):95-107. doi: 10.1016/j.ejpb.2020.04.023. [PMID: 32387703]
  • Seyedeh Maedeh Majidi, Mohammad Reza Hadjmohammadi. Hydrophobic borneol-based natural deep eutectic solvents as a green extraction media for air-assisted liquid-liquid micro-extraction of warfarin in biological samples. Journal of chromatography. A. 2020 Jun; 1621(?):461030. doi: 10.1016/j.chroma.2020.461030. [PMID: 32192705]
  • Abbey E Wilson, Darrell L Sparks, Katrina K Knott, Scott Willard, Ashli Brown. Simultaneous choice bioassays accompanied by physiological changes identify civetone and decanoic acid as pheromone candidates for giant pandas. Zoo biology. 2020 May; 39(3):176-185. doi: 10.1002/zoo.21532. [PMID: 31919913]
  • 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]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Hubertine M E Willems, Jeremy S Stultz, Molly E Coltrane, Jabez P Fortwendel, Brian M Peters. Disparate Candida albicans Biofilm Formation in Clinical Lipid Emulsions Due to Capric Acid-Mediated Inhibition. Antimicrobial agents and chemotherapy. 2019 11; 63(11):. doi: 10.1128/aac.01394-19. [PMID: 31405860]
  • Julie Enderlin, Anna Loussouarn, Jean-François Benoist, Blandine Dozières-Puyravel, Stéphane Auvin. Absence of increased blood decanoic acid levels in children with epilepsy treated with classic ketogenic diet. Epileptic disorders : international epilepsy journal with videotape. 2019 Aug; 21(4):366-369. doi: 10.1684/epd.2019.1079. [PMID: 31366451]
  • Sung Ill Jang, Seok Jeong, Don Haeng Lee, Kun Na, Sugeun Yang, Dong Ki Lee. Safety Evaluation of Paclitaxel-Eluting Biliary Metal Stent with Sodium Caprate in Porcine Biliary Tract. Gut and liver. 2019 04; 13(4):471-478. doi: 10.5009/gnl18454. [PMID: 30970427]
  • Chunxiao Ren, Qiqi Zhou, Wutai Guan, Xiaofeng Lin, Yijiang Wang, Hanqing Song, Yinzhi Zhang. Immune Response of Piglets Receiving Mixture of Formic and Propionic Acid Alone or with Either Capric Acid or Bacillus Licheniformis after Escherichia coli Challenge. BioMed research international. 2019; 2019(?):6416187. doi: 10.1155/2019/6416187. [PMID: 31019970]
  • Yawen Li, Angelina Angelova, Jianwen Liu, Vasil M Garamus, Na Li, Markus Drechsler, Yabin Gong, Aihua Zou. In situ phase transition of microemulsions for parenteral injection yielding lyotropic liquid crystalline carriers of the antitumor drug bufalin. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):217-225. doi: 10.1016/j.colsurfb.2018.09.023. [PMID: 30296646]
  • A Yu Lyudinina, G E Ivankova, E R Bojko. Priority use of medium-chain fatty acids during high-intensity exercise in cross-country skiers. Journal of the International Society of Sports Nutrition. 2018 Dec; 15(1):57. doi: 10.1186/s12970-018-0265-4. [PMID: 30526607]
  • Tim Erkens, Ruud Bueters, Marjolein van Heerden, Filip Cuyckens, Rob Vreeken, Nick Goeminne, Lieve Lammens. Translational safety biomarkers of colonic barrier integrity in the rat. Journal of applied toxicology : JAT. 2018 10; 38(10):1282-1292. doi: 10.1002/jat.3639. [PMID: 29781175]
  • 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]
  • John P Gleeson, Jesús M Frías, Sinéad M Ryan, David J Brayden. Sodium caprate enables the blood pressure-lowering effect of Ile-Pro-Pro and Leu-Lys-Pro in spontaneously hypertensive rats by indirectly overcoming PepT1 inhibition. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 Jul; 128(?):179-187. doi: 10.1016/j.ejpb.2018.04.021. [PMID: 29684535]
  • Joanne Heade, Sam Maher, Sinead B Bleiel, David J Brayden. Labrasol® and Salts of Medium-Chain Fatty Acids Can Be Combined in Low Concentrations to Increase the Permeability of a Macromolecule Marker Across Isolated Rat Intestinal Mucosae. Journal of pharmaceutical sciences. 2018 06; 107(6):1648-1655. doi: 10.1016/j.xphs.2018.02.012. [PMID: 29462634]
  • Cristina Caleja, Lillian Barros, João C M Barreira, Ana Ciric, Marina Sokovic, Ricardo C Calhelha, M Beatriz, P P Oliveira, Isabel C F R Ferreira. Suitability of lemon balm (Melissa officinalis L.) extract rich in rosmarinic acid as a potential enhancer of functional properties in cupcakes. Food chemistry. 2018 Jun; 250(?):67-74. doi: 10.1016/j.foodchem.2018.01.034. [PMID: 29412929]
  • Changwon Yang, Whasun Lim, Fuller W Bazer, Gwonhwa Song. Decanoic acid suppresses proliferation and invasiveness of human trophoblast cells by disrupting mitochondrial function. Toxicology and applied pharmacology. 2018 01; 339(?):121-132. doi: 10.1016/j.taap.2017.12.009. [PMID: 29248464]
  • Jitka Čejková, Martin M Hanczyc, František Štěpánek. Multi-Armed Droplets as Shape-Changing Protocells. Artificial life. 2018; 24(1):71-79. doi: 10.1162/artl_a_00255. [PMID: 29369709]
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