Caproic acid (BioDeep_00000002191)

 

Secondary id: BioDeep_00000229603, BioDeep_00000405296, BioDeep_00000861084, BioDeep_00000872171

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


Hexanoic acid, sodium salt, 1-(11)C-labeled

化学式: C6H12O2 (116.08372519999999)
中文名称: 正己酸, 己酸, 己酸-1,2-13C2, 己酸, 己酸, 己酸, 己酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.41%

分子结构信息

SMILES: C(=O)(O)CCCCC
InChI: InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

描述信息

Caproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15\\% of the fat in goats milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230).
Present in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient
KEIO_ID C035

同义名列表

53 个代谢物同义名

Hexanoic acid, sodium salt, 1-(11)C-labeled; Hexanoic acid, manganese (2+) salt; Hexanoic acid, sodium salt (1:1); Hexanoic acid, rhodium (2+) salt; Hexanoic acid, copper (2+) salt; Hexanoic acid, nickel (2+) salt; Hexanoic acid, potassium salt; Hexanoic acid, calcium salt; Hexanoic acid, sodium salt; Hexanoic acid, barium salt; Caproic acid sodium salt; 1-Pentanecarboxylic acid; Pentanecarboxylic acid; Bismuth(III)hexanoate; 1-Pentanecarboxylate; Calcium N-hexanoate; Pentanecarboxylate; Calcium hexanoate; Pentylformic acid; Butylacetic acid; Sodium capronate; Sodium hexanoate; Pentiformic acid; 1-Hexanoic acid; Sodium caproate; n-Hexanoic acid; CH3-[CH2]4-COOH; N-Caproic acid; N-Hexylic acid; Capronic acid; HEXANOIC ACID; N-Hexoic acid; Pentylformate; Caproic acid; Pentiformate; Hexylic acid; Butylacetate; 1-Hexanoate; N-Hexanoate; Hexoic acid; N-Hexylate; N-Caproate; Capronate; Bi(ohex)3; N-Hexoate; Hexanoate; Caproate; Hexylate; FA(6:0); Hexoate; C6:0; 6:0; Hexanoic acid



数据库引用编号

30 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

18 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(18)

PharmGKB(0)

59 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

  • Rikard Fristedt, Vanessa Ruppert, Tania Trower, Janine Cooney, Rikard Landberg. Quantitation of circulating short-chain fatty acids in small volume blood samples from animals and humans. Talanta. 2024 May; 272(?):125743. doi: 10.1016/j.talanta.2024.125743. [PMID: 38382298]
  • Huiqin Shi, Wei Li, Hongyu Chen, Yao Meng, Huifang Wu, Jian Wang, Shuo Shen. Synthetic Microbial Community Members Interact to Metabolize Caproic Acid to Inhibit Potato Dry Rot Disease. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084437. [PMID: 38674022]
  • Sergio Morales-Palomo, Clara Navarrete, José Luis Martínez, Cristina González-Fernández, Elia Tomás-Pejó. Transcriptomic profiling of an evolved Yarrowia lipolytica strain: tackling hexanoic acid fermentation to increase lipid production from short-chain fatty acids. Microbial cell factories. 2024 Apr; 23(1):101. doi: 10.1186/s12934-024-02367-4. [PMID: 38566056]
  • Yiming Ni, Liangyin Cai, Xiaojun Gou, Wenjie Li, Mingmei Zhou, Ying Huang. Therapeutic effect of Sanhua decoction on rats with middle cerebral artery occlusion and the associated changes in gut microbiota and short-chain fatty acids. PloS one. 2024; 19(2):e0298148. doi: 10.1371/journal.pone.0298148. [PMID: 38363776]
  • Hongbo Yuan, Bingke Shi, Zhuoni Wang, Genhong Qin, Hui Hou, Hongtao Tu, Li Wang. Exploration of the Biocontrol Activity of Bacillus atrophaeus Strain HF1 against Pear Valsa Canker Caused by Valsa pyri. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015477. [PMID: 37895155]
  • Valentino Casolo, Marco Zancani, Elisa Pellegrini, Antonio Filippi, Sara Gargiulo, Dennis Konnerup, Piero Morandini, Ole Pedersen. Restricted O2 consumption in pea roots induced by hexanoic acid is linked to depletion of Krebs cycle substrates. Physiologia plantarum. 2023 Sep; 175(5):e14024. doi: 10.1111/ppl.14024. [PMID: 37882315]
  • Ji Wang, Yanhao Zhang, Shuo Dong, Wenhui Zha, Chao Liu, Yang Wang, Yuhao Jiang, Hanlei Xing, Xinsong Li. Bivalent mRNA vaccines against three SARS-CoV-2 variants mediated by new ionizable lipid nanoparticles. International journal of pharmaceutics. 2023 Jul; 642(?):123155. doi: 10.1016/j.ijpharm.2023.123155. [PMID: 37402442]
  • 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]
  • Tinh Van Nguyen, Tomeu Viver, Ilse Smets, Kristel Bernaerts, Karoline Faust, Rob Lavigne, Laurent Poughon, Claude-Gilles Dussap, Dirk Springael. Thermocaproicibacter melissae gen. nov., sp. nov., a thermophilic chain-elongating bacterium, producing n-caproate from polymeric carbohydrates. International journal of systematic and evolutionary microbiology. 2023 May; 73(5):. doi: 10.1099/ijsem.0.005893. [PMID: 37200213]
  • Ying He, Bang Cheng, Bing-Jian Guo, Zheng Huang, Jing-Hua Qin, Qian-Yi Wang, Lin-Lin Feng, Yun-Yuan Nong, Dan Zhu, Hong-Wei Guo, Zhi-Heng Su. Metabonomics and 16S rRNA gene sequencing to study the therapeutic mechanism of Danggui Sini decoction on collagen-induced rheumatoid arthritis rats with Cold Bi syndrome. Journal of pharmaceutical and biomedical analysis. 2023 Jan; 222(?):115109. doi: 10.1016/j.jpba.2022.115109. [PMID: 36270097]
  • Chongrong Shen, Yanru Chen, Qiaoling Wang, Yingkai Sun, Huibin Lin, Mengshan Ni, Yufei Chen, Ling Zhang, Jiabin Jin, Xiayang Ying, Yuyao Zou, Xiaolin Wang, Yaorui Ye, Miaomiao Yuan, Nan Yin, Zhiwen Cao, Yifei Zhang, Weiqiong Gu, Weiqing Wang, Guang Ning, Jiqiu Wang, Shaoqian Zhao, Jie Hong, Ruixin Liu. Fecal short chain fatty acids modify therapeutic effects of sleeve gastrectomy. Frontiers in endocrinology. 2023; 14(?):1277035. doi: 10.3389/fendo.2023.1277035. [PMID: 38027127]
  • Zachary A Drum, Stephen M Lanno, Sara M Gregory, Serena J Shimshak, Mukshud Ahamed, Will Barr, Bethlehem Bekele, Alison Biester, Colleen Castro, Lauren Connolly, Nicole DelGaudio, William Humphrey, Helen Karimi, Sophie Karolczak, Tay-Shaun Lawrence, Andrew McCracken, Noah Miller-Medzon, Leah Murphy, Cameron Park, Sojeong Park, Chloe Qiu, Kevin Serra, Gigi Snyder, Alexa Strauss, Spencer Tang, Christina Vyzas, Joseph D Coolon. Genomics analysis of hexanoic acid exposure in Drosophila species. G3 (Bethesda, Md.). 2022 01; 12(1):. doi: 10.1093/g3journal/jkab354. [PMID: 34718544]
  • M N Caccalano, G Dilarri, C F C Zamuner, D S Domingues, H Ferreira. Hexanoic acid: a new potential substitute for copper-based agrochemicals against citrus canker. Journal of applied microbiology. 2021 Nov; 131(5):2488-2499. doi: 10.1111/jam.15125. [PMID: 34008224]
  • Ping Song, Hui Xu, Jixiu Zhang, Huatao Chen, Li Li, Yana Qu, Feng Lin, Qun Zhang. Functional analysis of indole 3-hexanoic acid as a novel auxin from Arabidopsis thaliana. Planta. 2021 Sep; 254(4):69. doi: 10.1007/s00425-021-03719-9. [PMID: 34498125]
  • Takahiro Mori, Kiyofumi Wanibuchi, Hiroyuki Morita, Ikuro Abe. Amide Bond Formation Using 4-Coumarate: CoA Ligase from Arabidopsis thaliana. Chemical & pharmaceutical bulletin. 2021 Aug; 69(8):717-720. doi: 10.1248/cpb.c21-00404. [PMID: 34053981]
  • David R Hall, Steven J Harte, Daniel P Bray, Dudley I Farman, Rob James, Celine X Silva, Michelle T Fountain. Hero Turned Villain: Identification of Components of the Sex Pheromone of the Tomato Bug, Nesidiocoris tenuis. Journal of chemical ecology. 2021 May; 47(4-5):394-405. doi: 10.1007/s10886-021-01270-1. [PMID: 33844148]
  • Mohamed El-Far, Madeleine Durand, Isabelle Turcotte, Etienne Larouche-Anctil, Mohamed Sylla, Sarah Zaidan, Carl Chartrand-Lefebvre, Rémi Bunet, Hardik Ramani, Manel Sadouni, Irina Boldeanu, Annie Chamberland, Sylvie Lesage, Jean-Guy Baril, Benoit Trottier, Réjean Thomas, Emmanuel Gonzalez, Ali Filali-Mouhim, Jean-Philippe Goulet, Jeffrey A Martinson, Seble Kassaye, Roksana Karim, Jorge R Kizer, Audrey L French, Stephen J Gange, Petronela Ancuta, Jean-Pierre Routy, David B Hanna, Robert C Kaplan, Nicolas Chomont, Alan L Landay, Cécile L Tremblay. Upregulated IL-32 Expression And Reduced Gut Short Chain Fatty Acid Caproic Acid in People Living With HIV With Subclinical Atherosclerosis. Frontiers in immunology. 2021; 12(?):664371. doi: 10.3389/fimmu.2021.664371. [PMID: 33936102]
  • Jacob Bejder, Gözde Gürdeniz, Cătălina Cuparencu, Frederikke Hall, Mikkel Gybel-Brask, Andreas Breenfeldt Andersen, Lars Ove Dragsted, Niels H Secher, Pär I Johansson, Nikolai Baastrup Nordsborg. An Untargeted Urine Metabolomics Approach for Autologous Blood Transfusion Detection. Medicine and science in sports and exercise. 2021 01; 53(1):236-243. doi: 10.1249/mss.0000000000002442. [PMID: 32694367]
  • Marina Saresella, Ivana Marventano, Monica Barone, Francesca La Rosa, Federica Piancone, Laura Mendozzi, Alessia d'Arma, Valentina Rossi, Luigi Pugnetti, Gabriella Roda, Eleonora Casagni, Michele Dei Cas, Rita Paroni, Patrizia Brigidi, Silvia Turroni, Mario Clerici. Alterations in Circulating Fatty Acid Are Associated With Gut Microbiota Dysbiosis and Inflammation in Multiple Sclerosis. Frontiers in immunology. 2020; 11(?):1390. doi: 10.3389/fimmu.2020.01390. [PMID: 32733460]
  • Wyckliff P Omondi, Eunice A Owino, David Odongo, Joseph M Mwangangi, Baldwyn Torto, David P Tchouassi. Differential response to plant- and human-derived odorants in field surveillance of the dengue vector, Aedes aegypti. Acta tropica. 2019 Dec; 200(?):105163. doi: 10.1016/j.actatropica.2019.105163. [PMID: 31494122]
  • S M Lanno, J D Coolon. Derived esterase activity in Drosophila sechellia contributes to evolved octanoic acid resistance. Insect molecular biology. 2019 12; 28(6):798-806. doi: 10.1111/imb.12587. [PMID: 30977928]
  • Soshi Takahashi, Jun Saegusa, Akira Onishi, Akio Morinobu. Biomarkers identified by serum metabolomic analysis to predict biologic treatment response in rheumatoid arthritis patients. Rheumatology (Oxford, England). 2019 12; 58(12):2153-2161. doi: 10.1093/rheumatology/kez199. [PMID: 31143951]
  • Fei Shi, Xin Zhou, Miao-Miao Yao, Qian Zhou, Shu-Juan Ji, Yu Wang. Low-temperature stress-induced aroma loss by regulating fatty acid metabolism pathway in 'Nanguo' pear. Food chemistry. 2019 Nov; 297(?):124927. doi: 10.1016/j.foodchem.2019.05.201. [PMID: 31253294]
  • Jin Zhang, Sonja Bisch-Knaden, Richard A Fandino, Shuwei Yan, George F Obiero, Ewald Grosse-Wilde, Bill S Hansson, Markus Knaden. The olfactory coreceptor IR8a governs larval feces-mediated competition avoidance in a hawkmoth. Proceedings of the National Academy of Sciences of the United States of America. 2019 10; 116(43):21828-21833. doi: 10.1073/pnas.1913485116. [PMID: 31591212]
  • María José López-Galiano, Inmaculada García-Robles, Víctor Manuel Ruiz-Arroyo, Sara Sanchís Oltra, Marko Petek, Carolina Rausell, M Dolores Real. Colorado potato beetle chymotrypsin genes are differentially regulated in larval midgut in response to the plant defense inducer hexanoic acid or the Bacillus thuringiensis Cry3Aa toxin. Journal of invertebrate pathology. 2019 09; 166(?):107224. doi: 10.1016/j.jip.2019.107224. [PMID: 31362005]
  • Qianhong Ye, Shuang Cai, Shuai Wang, Xiangzhou Zeng, Changchuan Ye, Meixia Chen, Xiangfang Zeng, Shiyan Qiao. Maternal short and medium chain fatty acids supply during early pregnancy improves embryo survival through enhancing progesterone synthesis in rats. The Journal of nutritional biochemistry. 2019 07; 69(?):98-107. doi: 10.1016/j.jnutbio.2019.03.015. [PMID: 31063920]
  • Li-Chun Chen, Ke-Xian Chen, Xi-Ying Huang, Jian Lou, Jing-Yuan Li, Shao-Ping Deng. Vesicles from the self-assembly of the ultra-small fatty acids with amino acids under aqueous conditions. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):69-76. doi: 10.1016/j.colsurfb.2018.07.007. [PMID: 30267956]
  • Wei Wei, Zhonggui He, Jincheng Yang, Mengchi Sun, Jin Sun. Cytosine arabinoside prodrug designed to bind plasma serum albumin for drug delivery. Drug delivery and translational research. 2018 10; 8(5):1162-1170. doi: 10.1007/s13346-018-0534-4. [PMID: 29748833]
  • Lisa R Hoving, Marieke Heijink, Vanessa van Harmelen, Ko Willems van Dijk, Martin Giera. GC-MS Analysis of Short-Chain Fatty Acids in Feces, Cecum Content, and Blood Samples. Methods in molecular biology (Clifton, N.J.). 2018; 1730(?):247-256. doi: 10.1007/978-1-4939-7592-1_17. [PMID: 29363078]
  • R D Peyser, S M Lanno, S J Shimshak, J D Coolon. Analysis of cytochrome P450 contribution to evolved plant toxin resistance in Drosophila sechellia. Insect molecular biology. 2017 Dec; 26(6):715-720. doi: 10.1111/imb.12329. [PMID: 28703934]
  • Arnaud T Djami-Tchatchou, Efficient N Ncube, Paul A Steenkamp, Ian A Dubery. Similar, but different: structurally related azelaic acid and hexanoic acid trigger differential metabolomic and transcriptomic responses in tobacco cells. BMC plant biology. 2017 Nov; 17(1):227. doi: 10.1186/s12870-017-1157-5. [PMID: 29187153]
  • M José López-Galiano, Víctor Manuel Ruiz-Arroyo, Emma Fernández-Crespo, Carolina Rausell, M Dolores Real, Pilar García-Agustín, Carmen González-Bosch, Inmaculada García-Robles. Oxylipin mediated stress response of a miraculin-like protease inhibitor in Hexanoic acid primed eggplant plants infested by Colorado potato beetle. Journal of plant physiology. 2017 Aug; 215(?):59-64. doi: 10.1016/j.jplph.2017.04.013. [PMID: 28578135]
  • Jing Liu, Dujuan Zhao, Wenxiu He, Huiyuan Zhang, Zhonghao Li, Yuxia Luan. Nanoassemblies from amphiphilic cytarabine prodrug for leukemia targeted therapy. Journal of colloid and interface science. 2017 Feb; 487(?):239-249. doi: 10.1016/j.jcis.2016.10.041. [PMID: 27776282]
  • Yu V Holota, O O Holubenko, A M Ostapchuk, T M Serhiychuk, L V Zakordonets, G M Tolstanova. Fecal short-chain fatty acids at different time points after ceftriaxone administration in rats. Ukrainian biochemical journal. 2017 Jan; 89(1):50-8. doi: 10.15407/ubj89.01.050. [PMID: 29236389]
  • M Roostaei-Ali Mehr, P Parisoush. Effect of Different Levels of Silymarin and Caproic Acid on Storage of Ram Semen in Liquid Form. Reproduction in domestic animals = Zuchthygiene. 2016 Aug; 51(4):569-74. doi: 10.1111/rda.12721. [PMID: 27321767]
  • Byung-Chun Kim, Byoung Seung Jeon, Seil Kim, Hyunook Kim, Youngsoon Um, Byoung-In Sang. Caproiciproducens galactitolivorans gen. nov., sp. nov., a bacterium capable of producing caproic acid from galactitol, isolated from a wastewater treatment plant. International journal of systematic and evolutionary microbiology. 2015 Dec; 65(12):4902-4908. doi: 10.1099/ijsem.0.000665. [PMID: 26474980]
  • Alberto Caminero, Esther Nistal, Alexandra R Herrán, Jénifer Pérez-Andrés, Miguel A Ferrero, Luis Vaquero Ayala, Santiago Vivas, José M G Ruiz de Morales, Silvia M Albillos, Francisco Javier Casqueiro. Differences in gluten metabolism among healthy volunteers, coeliac disease patients and first-degree relatives. The British journal of nutrition. 2015 Oct; 114(8):1157-67. doi: 10.1017/s0007114515002767. [PMID: 26428276]
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