FA(16:1) (BioDeep_00000229658)

   

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


cis-9-hexadecenoic acid

化学式: C16H30O2 (254.224568)
中文名称: 顺-9-十六碳烯酸
谱图信息: 最多检出来源 Viridiplantae(plant) 7.84%

Reviewed

Last reviewed on 2024-07-15.

Cite this Page

FA(16:1). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/fa(16:1) (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000229658). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CCCCCCC(=O)O)/C=C\CCCCCC
InChI: InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

描述信息

Palmitoleic acid (FA 16:1), also known as hexadecenoic acid, is a monounsaturated omega-7 fatty acid with a 16-carbon chain and a double bond at the 9th position. In biological terms, palmitoleic acid serves several important functions:
1. **Energy Source:** Like other fatty acids, palmitoleic acid is a significant source of energy. It can be oxidized through beta-oxidation to produce ATP, the energy currency of the cell.
2. **Cell Membrane Structure:** Palmitoleic acid is a component of phospholipids, which are major constituents of cell membranes. The presence of monounsaturated fatty acids like palmitoleic acid helps maintain the fluidity and flexibility of cell membranes, which is crucial for various cellular processes.
3. **Lipid Signaling:** Palmitoleic acid and its derivatives can act as signaling molecules. For example, it is converted into the lipid mediator called palmitoleoyl-lysophosphatidylcholine (LPC), which plays a role in inflammation and blood clotting.
4. **Insulin Sensitivity:** Palmitoleic acid has been shown to improve insulin sensitivity, which is important for glucose metabolism and can help in the prevention and treatment of type 2 diabetes.
5. **Inflammation Modulation:** Some studies suggest that palmitoleic acid may have anti-inflammatory effects, which could be beneficial in reducing the risk of chronic diseases associated with inflammation.
6. **Skin Health:** Palmitoleic acid is naturally present in the skin and is considered a component of the skin's surface lipids, contributing to the skin's barrier function and helping to prevent water loss.
7. **Biosynthesis of Other Lipids:** Palmitoleic acid serves as a precursor for the synthesis of other complex lipids, including prostaglandins and other eicosanoids, which are involved in a wide range of physiological processes such as inflammation and blood pressure regulation.
8. **Cardiovascular Health:** The consumption of monounsaturated fatty acids like palmitoleic acid is often associated with a lower risk of cardiovascular diseases, although the direct role of palmitoleic acid in this context is still under investigation.
It's important to note that while palmitoleic acid has these potential biological functions, the overall impact on health can depend on the balance of fatty acids in the diet and the context of the individual's overall metabolic health.

Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.
Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

同义名列表

12 个代谢物同义名

cis-9-hexadecenoic acid; cis-9-palmitoleic acid; 9Z-hexadecenoic acid; cis-Palmitoleic acid; 9Z-palmitoleic acid; Oleopalmitic acid; Palmitoleic acid; Physetoleic acid; Zoomeric acid; Zoomaric acid; C16:1n-7; FA 16:1



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)

412 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

  • Junhui Zhang, Minjie Zhao, Huilin Yu, Qianqian Wang, Fei Shen, Haiying Cai, Fengqin Feng, Jun Tang. Palmitoleic Acid Ameliorates Metabolic Disorders and Inflammation by Modulating Gut Microbiota and Serum Metabolites. Molecular nutrition & food research. 2024 Apr; 68(7):e2300749. doi: 10.1002/mnfr.202300749. [PMID: 38511225]
  • Qingting Yu, Yanzhuo Yang, Ting Xu, Yinsheng Cai, Zuisu Yang, Falei Yuan. Palmitoleic acid protects microglia from palmitate-induced neurotoxicity in vitro. PloS one. 2024; 19(1):e0297031. doi: 10.1371/journal.pone.0297031. [PMID: 38241239]
  • Xiujuan Qian, Huirui Lei, Xinhai Zhou, Lili Zhang, Wenxing Cui, Jie Zhou, Fengxue Xin, Weiliang Dong, Min Jiang, Katrin Ochsenreither. Engineering Scheffersomyces segobiensis for palmitoleic acid-rich lipid production. Microbial biotechnology. 2024 Jan; 17(1):e14301. doi: 10.1111/1751-7915.14301. [PMID: 37351580]
  • Jing Ning, Xiaoting Gu, Jiao Zhou, Hongxia Zhang, Jianghua Sun, Lilin Zhao. Palmitoleic acid as a coordinating molecule between the invasive pinewood nematode and its newly associated fungi. The ISME journal. 2023 11; 17(11):1862-1871. doi: 10.1038/s41396-023-01489-8. [PMID: 37604917]
  • Eliza Korkus, Marcin Szustak, Rafal Madaj, Arkadiusz Chworos, Anna Drzazga, Maria Koziołkiewicz, Grzegorz Dąbrowski, Sylwester Czaplicki, Iwona Konopka, Edyta Gendaszewska-Darmach. Trans-palmitoleic acid, a dairy fat biomarker, stimulates insulin secretion and activates G protein-coupled receptors with a different mechanism from the cis isomer. Food & function. 2023 Jul; 14(14):6496-6512. doi: 10.1039/d2fo03412c. [PMID: 37368452]
  • 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]
  • Ecesu Cetin, Brian Pedersen, Lindsey M Porter, Gail K Adler, Mehmet Furkan Burak. Protocol for a randomized placebo-controlled clinical trial using pure palmitoleic acid to ameliorate insulin resistance and lipogenesis in overweight and obese subjects with prediabetes. Frontiers in endocrinology. 2023; 14(?):1306528. doi: 10.3389/fendo.2023.1306528. [PMID: 38313838]
  • Yiwei Chen, Qiongdan Mai, Zixu Chen, Tao Lin, Yongjie Cai, Jing Han, Ying Wang, Mudan Zhang, Shimin Tan, Zhiying Wu, Lingming Chen, Zhiyi Zhang, Yi Yang, Taimei Cui, Beiyin Ouyang, Yue Sun, Lijia Yang, Lin Xu, Sien Zhang, Jian Li, Hongbo Shen, Linna Liu, Lingchan Zeng, Shenghong Zhang, Gucheng Zeng. Dietary palmitoleic acid reprograms gut microbiota and improves biological therapy against colitis. Gut microbes. 2023 Jan; 15(1):2211501. doi: 10.1080/19490976.2023.2211501. [PMID: 37203220]
  • Wenwen Huang, Yiping Zhang, Liping Zhong, Chunlong Sun, Zaiwang Zhang. Simultaneous determination of cis- and trans-palmitoleic acid in rat serum by UPLC-MS/MS. Scientific reports. 2022 10; 12(1):16637. doi: 10.1038/s41598-022-20739-x. [PMID: 36198714]
  • Yasuhiro Takenouchi, Yoshie Seki, Sachiko Shiba, Kazuo Ohtake, Koji Nobe, Keizo Kasono. Effects of dietary palmitoleic acid on vascular function in aorta of diabetic mice. BMC endocrine disorders. 2022 Apr; 22(1):103. doi: 10.1186/s12902-022-01018-2. [PMID: 35436932]
  • Jian Ding, Chengjiang Ruan, Ying Guan, He Li, Wei Du, Shunguang Lu, Xiufeng Wen, Ke Tang, Ye Chen. Nontargeted metabolomic and multigene expression analyses reveal the mechanism of oil biosynthesis in sea buckthorn berry pulp rich in palmitoleic acid. Food chemistry. 2022 Apr; 374(?):131719. doi: 10.1016/j.foodchem.2021.131719. [PMID: 34875440]
  • Lidia Irasema Chávaro-Ortiz, Brenda D Tapia, Mariel Rico-Hidalgo, Ruth Gutiérrez-Aguilar, María E Frigolet. Trans-palmitoleic acid reduces adiposity via increased lipolysis in a rodent model of diet-induced obesity. The British journal of nutrition. 2022 03; 127(6):801-809. doi: 10.1017/s0007114521001501. [PMID: 33958011]
  • Oliver Konzock, Yuika Matsushita, Simone Zaghen, Aboubakar Sako, Joakim Norbeck. Altering the fatty acid profile of Yarrowia lipolytica to mimic cocoa butter by genetic engineering of desaturases. Microbial cell factories. 2022 Feb; 21(1):25. doi: 10.1186/s12934-022-01748-x. [PMID: 35183179]
  • Erin Vanessa LaRae Smith, Rebecca Maree Dyson, Christina M G Vanderboor, Ousseynou Sarr, Jane Anderson, Mary J Berry, Timothy R H Regnault, Lifeng Peng, Clint Gray. Maternal Fructose Intake Causes Developmental Reprogramming of Hepatic Mitochondrial Catalytic Activity and Lipid Metabolism in Weanling and Young Adult Offspring. International journal of molecular sciences. 2022 Jan; 23(2):. doi: 10.3390/ijms23020999. [PMID: 35055185]
  • Herlambang Herlambang, Anggelia Puspasari, Citra Maharani, Rina Nofri Enis, Susan Tarawifa, Amelia Dwi Fitri, Huntari Harahap, Asro Hayani Harahap, Erny Kusdiyah, Mas Rizky Anggun Adipurna Syamsunarno. Comprehensive fatty acid fractionation profilling in preeclampsia: a case control study with multivariable analysis. BMC pregnancy and childbirth. 2022 Jan; 22(1):8. doi: 10.1186/s12884-021-04313-3. [PMID: 34980007]
  • Denisa Miklankova, Irena Markova, Martina Hüttl, Barbora Stankova, Hana Malinska. The Different Insulin-Sensitising and Anti-Inflammatory Effects of Palmitoleic Acid and Oleic Acid in a Prediabetes Model. Journal of diabetes research. 2022; 2022(?):4587907. doi: 10.1155/2022/4587907. [PMID: 36147256]
  • Iris Rosa Betz, Sarah Julia Qaiyumi, Madeleine Goeritzer, Arne Thiele, Sarah Brix, Niklas Beyhoff, Jana Grune, Robert Klopfleisch, Franziska Greulich, Nina Henriette Uhlenhaut, Ulrich Kintscher, Anna Foryst-Ludwig. Cardioprotective Effects of Palmitoleic Acid (C16:1n7) in a Mouse Model of Catecholamine-Induced Cardiac Damage Are Mediated by PPAR Activation. International journal of molecular sciences. 2021 Nov; 22(23):. doi: 10.3390/ijms222312695. [PMID: 34884498]
  • Yanan Song, Xiaodan Wang, Hongli Cui, Chunli Ji, Jinai Xue, Xiaoyun Jia, Ruiyan Ma, Runzhi Li. Enhancing growth and oil accumulation of a palmitoleic acid-rich Scenedesmus obliquus in mixotrophic cultivation with acetate and its potential for ammonium-containing wastewater purification and biodiesel production. Journal of environmental management. 2021 Nov; 297(?):113273. doi: 10.1016/j.jenvman.2021.113273. [PMID: 34311253]
  • Neil K Huang, Petra Bůžková, Nirupa R Matthan, Luc Djoussé, Jorge R Kizer, Kenneth J Mukamal, Joseph F Polak, Alice H Lichtenstein. Serum Non-Esterified Fatty Acids, Carotid Artery Intima-Media Thickness and Flow-Mediated Dilation in Older Adults: The Cardiovascular Health Study (CHS). Nutrients. 2021 Aug; 13(9):. doi: 10.3390/nu13093052. [PMID: 34578930]
  • Yuko Akazawa, Tomohito Morisaki, Hiroko Fukuda, Kiyuu Norimatsu, Junya Shiota, Keiichi Hashiguchi, Maiko Tabuchi, Moto Kitayama, Kayoko Matsushima, Naoyuki Yamaguchi, Hisayoshi Kondo, Fumihiko Fujita, Hiroaki Takeshita, Kazuhiko Nakao, Fuminao Takeshima. Significance of serum palmitoleic acid levels in inflammatory bowel disease. Scientific reports. 2021 08; 11(1):16260. doi: 10.1038/s41598-021-95923-6. [PMID: 34376800]
  • Carmela Maria Montone, Sara Elsa Aita, Martina Catani, Chiara Cavaliere, Andrea Cerrato, Susy Piovesana, Aldo Laganà, Anna Laura Capriotti. Profiling and quantitative analysis of underivatized fatty acids in Chlorella vulgaris microalgae by liquid chromatography-high resolution mass spectrometry. Journal of separation science. 2021 Aug; 44(16):3041-3051. doi: 10.1002/jssc.202100306. [PMID: 34101991]
  • Rubén Tovar, Ana Luisa Gavito, Antonio Vargas, Laura Soverchia, Laura Hernandez-Folgado, Nadine Jagerovic, Elena Baixeras, Roberto Ciccocioppo, Fernando Rodríguez de Fonseca, Juan Decara. Palmitoleoylethanolamide Is an Efficient Anti-Obesity Endogenous Compound: Comparison with Oleylethanolamide in Diet-Induced Obesity. Nutrients. 2021 Jul; 13(8):. doi: 10.3390/nu13082589. [PMID: 34444748]
  • Emma Solé, Roger Ros-Freixedes, Marc Tor, Ramona N Pena, Joan Estany. A sequence variant in the diacylglycerol O-acyltransferase 2 gene influences palmitoleic acid content in pig muscle. Scientific reports. 2021 07; 11(1):14797. doi: 10.1038/s41598-021-94235-z. [PMID: 34285308]
  • Jason I E Bruce, Rosa Sánchez-Alvarez, Maria Dolors Sans, Sarah A Sugden, Nathan Qi, Andrew D James, John A Williams. Insulin protects acinar cells during pancreatitis by preserving glycolytic ATP supply to calcium pumps. Nature communications. 2021 07; 12(1):4386. doi: 10.1038/s41467-021-24506-w. [PMID: 34282152]
  • Shanjie Wang, Wei Tian, Yige Liu, Guangcan Yan, Shaohong Fang, Yafeng Wang, Bo Yu. Temporal trend of circulating trans-fatty acids and risk of long-term mortality in general population. Clinical nutrition (Edinburgh, Scotland). 2021 03; 40(3):1095-1101. doi: 10.1016/j.clnu.2020.07.010. [PMID: 32768317]
  • M Plante-Dubé, C Picard, I Gilbert, C Robert, V Fievez, B Vlaeminck, C Belleannée, R Gervais, P Y Chouinard. Effects of a dietary supplement enriched in palmitoleic acid on fatty acid composition of follicular fluid, granulosa cell metabolism, and oocyte developmental capacity in early lactation dairy cows. Journal of dairy science. 2021 Mar; 104(3):3693-3706. doi: 10.3168/jds.2020-19191. [PMID: 33455772]
  • Xinyi Cheng, Yaqi Huang, Zhuangzhuang Yang, Tong Wang, Xiaosan Wang. Enrichment of Palmitoleic Acid by a Combination of Two-step Solvent Crystallization and Molecular Distillation. Journal of oleo science. 2021; 70(5):599-606. doi: 10.5650/jos.ess20273. [PMID: 33952786]
  • N L Weir, B T Steffen, W Guan, L M Johnson, L Djousse, K J Mukamal, M Y Tsai. Circulating omega-7 fatty acids are differentially related to metabolic dysfunction and incident type II diabetes: The Multi-Ethnic Study of Atherosclerosis (MESA). Diabetes & metabolism. 2020 09; 46(4):319-325. doi: 10.1016/j.diabet.2019.10.005. [PMID: 31706030]
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  • Myriam Lamine, Mahmoud Gargouri, Ahmed Mliki. Identification of the NaCl-responsive metabolites in Citrus roots: A lipidomic and volatomic signature. Plant signaling & behavior. 2020 08; 15(8):1777376. doi: 10.1080/15592324.2020.1777376. [PMID: 32508206]
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  • Ping Jiang, Lixin Xia, ZiKang Jin, Shaokat Ali, Mengyan Wang, Xiaohui Li, Runjun Yang, Xibi Fang, Zhihui Zhao. New function of the CD44 gene: Lipid metabolism regulation in bovine mammary epithelial cells. Journal of dairy science. 2020 Jul; 103(7):6661-6671. doi: 10.3168/jds.2019-17415. [PMID: 32359993]
  • Xinyue Huang, Shenglan Yi, Jianping Hu, Ziyu Du, Qingfeng Wang, Zi Ye, Qingfeng Cao, Guannan Su, Gangxiang Yuan, Chunjiang Zhou, Yao Wang, Aize Kijlstra, Peizeng Yang. Analysis of the role of palmitoleic acid in acute anterior uveitis. International immunopharmacology. 2020 Jul; 84(?):106552. doi: 10.1016/j.intimp.2020.106552. [PMID: 32422526]
  • Paweł Rostoff, Magdalena Frączek-Jucha, Ewa Konduracka, Jadwiga Nessler, Grzegorz Gajos. Serum phospholipid cis-palmitoleic acid in patients with type 2 diabetes and chronic coronary syndrome: an assessment of the relationship with diabetes duration, systemic low-grade inflammation and circulating oxidized low-density lipoprotein. Kardiologia polska. 2020 06; 78(6):584-587. doi: 10.33963/kp.15285. [PMID: 32267132]
  • Neil K Huang, Nirupa R Matthan, Jean M Galluccio, Peilin Shi, Alice H Lichtenstein, Dariush Mozaffarian. Supplementation with Seabuckthorn Oil Augmented in 16:1n-7t Increases Serum Trans-Palmitoleic Acid in Metabolically Healthy Adults: A Randomized Crossover Dose-Escalation Study. The Journal of nutrition. 2020 06; 150(6):1388-1396. doi: 10.1093/jn/nxaa060. [PMID: 32140719]
  • Hans Albert Pedersen, Chi Ndi, Susan J Semple, Bevan Buirchell, Birger Lindberg Møller, Dan Staerk. PTP1B-Inhibiting Branched-Chain Fatty Acid Dimers from Eremophila oppositifolia subsp. angustifolia Identified by High-Resolution PTP1B Inhibition Profiling and HPLC-PDA-HRMS-SPE-NMR Analysis. Journal of natural products. 2020 05; 83(5):1598-1610. doi: 10.1021/acs.jnatprod.0c00070. [PMID: 32255628]
  • Yuki Murakami, Chiaki Murakami, Fumi Hoshino, Qiang Lu, Rino Akiyama, Atsumi Yamaki, Daisuke Takahashi, Fumio Sakane. Palmitic acid- and/or palmitoleic acid-containing phosphatidic acids are generated by diacylglycerol kinase α in starved Jurkat T cells. Biochemical and biophysical research communications. 2020 05; 525(4):1054-1060. doi: 10.1016/j.bbrc.2020.02.162. [PMID: 32184022]
  • Takahiko Mitsui, Satoru Kira, Tatsuya Ihara, Norifumi Sawada, Hiroshi Nakagomi, Tatsuya Miyamoto, Hiroshi Shimura, Sachiko Tsuchiya, Mie Kanda, Masayuki Takeda. Metabolism of fatty acids and bile acids in plasma is associated with overactive bladder in males: potential biomarkers and targets for novel treatments in a metabolomics analysis. International urology and nephrology. 2020 Feb; 52(2):233-238. doi: 10.1007/s11255-019-02299-8. [PMID: 31587188]
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  • Paloma Acosta-Montaño, Eustolia Rodríguez-Velázquez, Esmeralda Ibarra-López, Héctor Frayde-Gómez, Jaime Mas-Oliva, Blanca Delgado-Coello, Ignacio A Rivero, Manuel Alatorre-Meda, Jorge Aguilera, Lizbeth Guevara-Olaya, Victor García-González. Fatty Acid and Lipopolysaccharide Effect on Beta Cells Proteostasis and its Impact on Insulin Secretion. Cells. 2019 08; 8(8):. doi: 10.3390/cells8080884. [PMID: 31412623]
  • Zhi-Hong Yang, Milton Pryor, Audrey Noguchi, Maureen Sampson, Brittany Johnson, Matthew Pryor, Kwame Donkor, Marcelo Amar, Alan T Remaley. Dietary Palmitoleic Acid Attenuates Atherosclerosis Progression and Hyperlipidemia in Low-Density Lipoprotein Receptor-Deficient Mice. Molecular nutrition & food research. 2019 06; 63(12):e1900120. doi: 10.1002/mnfr.201900120. [PMID: 30921498]
  • Jian Ding, Chengjiang Ruan, Wei Du, Ying Guan. RNA-seq data reveals a coordinated regulation mechanism of multigenes involved in the high accumulation of palmitoleic acid and oil in sea buckthorn berry pulp. BMC plant biology. 2019 May; 19(1):207. doi: 10.1186/s12870-019-1815-x. [PMID: 31109294]
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