Phytanate (BioDeep_00000004722)

 

Secondary id: BioDeep_00000019509, BioDeep_00000405369

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


3,7,11,15-Tetramethylhexadecoanoic acid

化学式: C20H40O2 (312.302814)
中文名称: 植烷酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.05%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Phytanate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phytanate (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000004722). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O
InChI: InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

描述信息

Phytanic acid (or 3,7,11,15-tetramethylhexadecanoic acid) is a 20-carbon branched-chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish. It is primarily formed by bacterial degradation of chlorophyll in the intestinal tract of ruminants. Unlike most fatty acids, phytanic acid cannot be metabolized by beta-oxidation (because of a methyl group in the beta position). Instead, it undergoes alpha-oxidation in the peroxisome, where it is converted into pristanic acid by the removal of one carbon. Pristanic acid can undergo several rounds of beta-oxidation in the peroxisome to form medium-chain fatty acids that can be converted into carbon dioxide and water in mitochondria. Refsum disease, an autosomal recessive neurological disorder caused by mutations in the PHYH gene, is characterized by having impaired alpha-oxidation activity. Individuals with Refsum disease accumulate large stores of phytanic acid in their blood and tissues. This frequently leads to peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Therefore, chronically high levels of phytanic acid can be neurotoxic. Phytanic acids neurotoxicity appears to lie in its ability to initiate astrocyte/neural cell death by activating the mitochondrial route of apoptosis. In particular, phytanic acid can induce the substantial generation of reactive oxygen species in isolated mitochondria as well as in intact cells. It also induces the release of cytochrome c from mitochondria.
A 20-carbon branched chain fatty acid, Phytanic acid is present in animal (primarily herbivores or omnivores) tissues where it may be derived from the chlorophyll in consumed plant material. Phytanic acid derives from the corresponding alcohol, phytol, and is ultimately oxidized into pristanic acid. In phytanic acid storage disease (Refsum disease) this lipid may comprise as much as 30\\% of the total fatty acids in plasma. These high levels in Refsum disease (a neurological disorder) are due to a phytanic acid alpha-hydroxylase deficiency.; A 20-carbon branched chain fatty acid. In phytanic acid storage disease (Refsum disease) this lipid may comprise as much as 30\\% of the total fatty acids of the plasma. This is due to a phytanic acid alpha-hydroxylase deficiency. [HMDB]

同义名列表

15 个代谢物同义名

3,7,11,15-Tetramethylhexadecoanoic acid; 3,7,11,15-Tetramethyl-hexadecanoic acid; 3,7,11,15-Tetramethyl hexadecanoic acid; 3,7,11,15-Tetramethylhexadecanoic acid; 3,7,11,15-Tetramethyl-hexadecansaeure; 3,7,11,15-Tetramethyl-hexadecanoate; 3,7,11,15-Tetramethylhexadecoanoate; 3,7,11,15-Tetramethyl hexadecanoate; 3,7,11,15-Tetramethylhexadecanoate; Phytanoic acid; Acid, phytanic; PHYTANIC ACID; Phytanoate; Phytanate; Phytanate



数据库引用编号

17 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

70 个相关的代谢反应过程信息。

Reactome(55)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(15)

PharmGKB(0)

4 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

  • Wentao Yang, Philipp Gutbrod, Katharina Gutbrod, Helga Peisker, Xiaoning Song, Anna-Lena Falz, Andreas J Meyer, Peter Dörmann. 2-Hydroxy-phytanoyl-CoA lyase (AtHPCL) is involved in phytol metabolism in Arabidopsis. The Plant journal : for cell and molecular biology. 2022 03; 109(5):1290-1304. doi: 10.1111/tpj.15632. [PMID: 34902195]
  • Maaike Blankestijn, Vincent W Bloks, Dicky Struik, Nicolette Huijkman, Niels Kloosterhuis, Justina C Wolters, Ronald J A Wanders, Frédéric M Vaz, Markus Islinger, Folkert Kuipers, Bart van de Sluis, Albert K Groen, Henkjan J Verkade, Johan W Jonker. Mice with a deficiency in Peroxisomal Membrane Protein 4 (PXMP4) display mild changes in hepatic lipid metabolism. Scientific reports. 2022 02; 12(1):2512. doi: 10.1038/s41598-022-06479-y. [PMID: 35169201]
  • Youssef Khalil, Sara Carrino, Fujun Lin, Anna Ferlin, Heena V Lad, Francesca Mazzacuva, Sara Falcone, Natalie Rivers, Gareth Banks, Danilo Concas, Carlos Aguilar, Andrew R Haynes, Andy Blease, Thomas Nicol, Raya Al-Shawi, Wendy Heywood, Paul Potter, Kevin Mills, Daniel P Gale, Peter T Clayton. Tissue Proteome of 2-Hydroxyacyl-CoA Lyase Deficient Mice Reveals Peroxisome Proliferation and Activation of ω-Oxidation. International journal of molecular sciences. 2022 Jan; 23(2):. doi: 10.3390/ijms23020987. [PMID: 35055171]
  • Luz Díaz-Storani, Anaelle A Clary, Diego M Moreno, María Sol Ballari, Exequiel O J Porta, Andrea B J Bracca, Jonathan B Johnston, Guillermo R Labadie. Synthesis and interaction of terminal unsaturated chemical probes with Mycobacterium tuberculosis CYP124A1. Bioorganic & medicinal chemistry. 2021 08; 44(?):116304. doi: 10.1016/j.bmc.2021.116304. [PMID: 34289431]
  • Masahiro Okamura, Takahiro Ueno, Sho Tanaka, Yusuke Murata, Hiroki Kobayashi, Aoi Miyamoto, Masanori Abe, Noboru Fukuda. Increased expression of acyl-CoA oxidase 2 in the kidney with plasma phytanic acid and altered gut microbiota in spontaneously hypertensive rats. Hypertension research : official journal of the Japanese Society of Hypertension. 2021 Jun; 44(6):651-661. doi: 10.1038/s41440-020-00611-z. [PMID: 33504992]
  • Tomonori Nakanishi, Kazuhiro Kagamizono, Sayaka Yokoyama, Ryoji Suzuki, Hiroyuki Sakakibara, Kazuhiro Sugamoto, Laurie Erickson, Satoshi Kawahara. Dietary phytanic acid-induced changes in tissue fatty acid profiles in mice. The Journal of dairy research. 2020 Nov; 87(4):498-500. doi: 10.1017/s0022029920001089. [PMID: 33243312]
  • Eui Hyun Kim, Geon A Kim, Anukul Taweechaipaisankul, Muhammad Rosyid Ridlo, Seok Hee Lee, Kihae Ra, Curie Ahn, Byeong Chun Lee. Phytanic acid-derived peroxisomal lipid metabolism in porcine oocytes. Theriogenology. 2020 Nov; 157(?):276-285. doi: 10.1016/j.theriogenology.2020.07.007. [PMID: 32823023]
  • Tomonori Nakanishi, Kazuhiro Kagamizono, Sayaka Yokoyama, Ryoji Suzuki, Hiroyuki Sakakibara, Laurie Erickson, Satoshi Kawahara. Effects of dietary phytol on tissue accumulation of phytanic acid and pristanic acid and on the tissue lipid profiles in mice. Animal science journal = Nihon chikusan Gakkaiho. 2020 Jan; 91(1):e13424. doi: 10.1111/asj.13424. [PMID: 32618084]
  • Pammi Subhashini, Sampangi Jaya Krishna, Ganni Usha Rani, Nooguri Sushma Chander, Gummadi Maheshwar Reddy, Shaik Mohammad Naushad. Application of machine learning algorithms for the differential diagnosis of peroxisomal disorders. Journal of biochemistry. 2019 Jan; 165(1):67-73. doi: 10.1093/jb/mvy085. [PMID: 30295825]
  • Ji-Yeong An, Huei-Fen Jheng, Hiroyuki Nagai, Kohei Sanada, Haruya Takahashi, Mari Iwase, Natsumi Watanabe, Young-Il Kim, Aki Teraminami, Nobuyuki Takahashi, Rieko Nakata, Hiroyasu Inoue, Shigeto Seno, Hideo Mastuda, Teruo Kawada, Tsuyoshi Goto. A Phytol-Enriched Diet Activates PPAR-α in the Liver and Brown Adipose Tissue to Ameliorate Obesity-Induced Metabolic Abnormalities. Molecular nutrition & food research. 2018 03; 62(6):e1700688. doi: 10.1002/mnfr.201700688. [PMID: 29377597]
  • Avery L McIntosh, Stephen M Storey, Huan Huang, Ann B Kier, Friedhelm Schroeder. Sex-dependent impact of Scp-2/Scp-x gene ablation on hepatic phytol metabolism. Archives of biochemistry and biophysics. 2017 12; 635(?):17-26. doi: 10.1016/j.abb.2017.10.011. [PMID: 29051070]
  • Shaista Chaudhary, Suhel Parvez. Phytanic acid induced neurological alterations in rat brain synaptosomes and its attenuation by melatonin. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Nov; 95(?):37-46. doi: 10.1016/j.biopha.2017.07.156. [PMID: 28826095]
  • Serena Mezzar, Evelyn De Schryver, Stanny Asselberghs, Els Meyhi, Petruta L Morvay, Myriam Baes, Paul P Van Veldhoven. Phytol-induced pathology in 2-hydroxyacyl-CoA lyase (HACL1) deficient mice. Evidence for a second non-HACL1-related lyase. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 Sep; 1862(9):972-990. doi: 10.1016/j.bbalip.2017.06.004. [PMID: 28629946]
  • Katharina Herzog, Henk van Lenthe, Ronald J A Wanders, Frédéric M Vaz, Hans R Waterham, Sacha Ferdinandusse. Identification and diagnostic value of phytanoyl- and pristanoyl-carnitine in plasma from patients with peroxisomal disorders. Molecular genetics and metabolism. 2017 07; 121(3):279-282. doi: 10.1016/j.ymgme.2017.05.003. [PMID: 28566232]
  • Samia Hadj Ahmed, Nadia Koubaa, Wafa Kharroubi, Amira Zarrouk, Amira Mnari, Fethi Batbout, Habib Gamra, Sonia Hammami, Gérard Lizard, Mohamed Hammami. Identification of long and very long chain fatty acids, plasmalogen-C16:0 and phytanic acid as new lipid biomarkers in Tunisian coronary artery disease patients. Prostaglandins & other lipid mediators. 2017 07; 131(?):49-58. doi: 10.1016/j.prostaglandins.2017.08.001. [PMID: 28789919]
  • Stephen M Storey, Huan Huang, Avery L McIntosh, Gregory G Martin, Ann B Kier, Friedhelm Schroeder. Impact of Fabp1/Scp-2/Scp-x gene ablation (TKO) on hepatic phytol metabolism in mice. Journal of lipid research. 2017 06; 58(6):1153-1165. doi: 10.1194/jlr.m075457. [PMID: 28411199]
  • Aoi Miyamoto, Takahiko Aoyama, Masahiro Okamura, Noboru Fukuda, Takahiro Ueno, Masanori Abe, Yoshiaki Matsumoto. Development of a Method for Measuring Phytanic Acid as a Lifestyle-related Disease Biomarker in Rat Serum Using Ultra-fast Liquid Chromatography-Ultraviolet Spectrophotometry Combined with a Modified 2-Nitrophenylhydrazine Derivatization Method. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2017; 33(3):365-368. doi: 10.2116/analsci.33.365. [PMID: 28302979]
  • Stephanie Krauß, Simon Hammann, Walter Vetter. Phytyl Fatty Acid Esters in the Pulp of Bell Pepper (Capsicum annuum). Journal of agricultural and food chemistry. 2016 Aug; 64(32):6306-11. doi: 10.1021/acs.jafc.6b02645. [PMID: 27458658]
  • Michela Semeraro, Cristiano Rizzo, Sara Boenzi, Marco Cappa, Enrico Bertini, Giacomo Antonetti, Carlo Dionisi-Vici. A new multiplex method for the diagnosis of peroxisomal disorders allowing simultaneous determination of plasma very-long-chain fatty acids, phytanic, pristanic, docosahexaenoic and bile acids by high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 2016 Jul; 458(?):159-64. doi: 10.1016/j.cca.2016.05.009. [PMID: 27189059]
  • Gursev S Dhaunsi, Mayra Alsaeid, Saghir Akhtar. Phytanic acid activates NADPH oxidase through transactivation of epidermal growth factor receptor in vascular smooth muscle cells. Lipids in health and disease. 2016 Jun; 15(?):105. doi: 10.1186/s12944-016-0273-9. [PMID: 27287039]
  • Masatoshi Matsunami, Nobuyuki Shimozawa, Akinari Fukuda, Tadayuki Kumagai, Masaya Kubota, Pin Fee Chong, Mureo Kasahara. Living-Donor Liver Transplantation From a Heterozygous Parent for Infantile Refsum Disease. Pediatrics. 2016 06; 137(6):. doi: 10.1542/peds.2015-3102. [PMID: 27221287]
  • Arthur Sorlin, Gilbert Briand, David Cheillan, Arnaud Wiedemann, Bettina Montaut-Verient, Emmanuelle Schmitt, François Feillet. Effect of l-Arginine in One Patient with Peroxisome Biogenesis Disorder due to PEX12 Deficiency. Neuropediatrics. 2016 Jun; 47(3):179-81. doi: 10.1055/s-0036-1578798. [PMID: 26947510]
  • Yachana Kataria, Margaret Wright, Ryan J Deaton, Erika Enk Rueter, Benjamin A Rybicki, Ann B Moser, Vijayalakshmi Ananthanrayanan, Peter H Gann. Dietary influences on tissue concentrations of phytanic acid and AMACR expression in the benign human prostate. The Prostate. 2015 Feb; 75(2):200-10. doi: 10.1002/pros.22905. [PMID: 25307752]
  • Margaret E Wright, Demetrius Albanes, Ann B Moser, Stephanie J Weinstein, Kirk Snyder, Satu Männistö, Peter H Gann. Serum phytanic and pristanic acid levels and prostate cancer risk in Finnish smokers. Cancer medicine. 2014 Dec; 3(6):1562-9. doi: 10.1002/cam4.319. [PMID: 25132681]
  • Nageshwar R Yepuri, Stephen A Holt, Greta Moraes, Peter J Holden, Khondker R Hossain, Stella M Valenzuela, Michael James, Tamim A Darwish. Stereoselective synthesis of perdeuterated phytanic acid, its phospholipid derivatives and their formation into lipid model membranes for neutron reflectivity studies. Chemistry and physics of lipids. 2014 Oct; 183(?):22-33. doi: 10.1016/j.chemphyslip.2014.04.004. [PMID: 24794716]
  • Federico Buonanno, Andrea Anesi, Graziano Guella, Santosh Kumar, Daizy Bharti, Antonietta La Terza, Luana Quassinti, Massimo Bramucci, Claudio Ortenzi. Chemical offense by means of toxicysts in the freshwater ciliate, Coleps hirtus. The Journal of eukaryotic microbiology. 2014 May; 61(3):293-304. doi: 10.1111/jeu.12106. [PMID: 24512001]
  • Tõnu Püssa. Toxicological issues associated with production and processing of meat. Meat science. 2013 Dec; 95(4):844-53. doi: 10.1016/j.meatsci.2013.04.032. [PMID: 23660174]
  • Ann B Moser, Jody Hey, Patricia K Dranchak, Mazen W Karaman, Junsong Zhao, Laura A Cox, Oliver A Ryder, Joseph G Hacia. Diverse captive non-human primates with phytanic acid-deficient diets rich in plant products have substantial phytanic acid levels in their red blood cells. Lipids in health and disease. 2013 Feb; 12(?):10. doi: 10.1186/1476-511x-12-10. [PMID: 23379307]
  • Estela Natacha Brandt Busanello, Ângela Zanatta, Anelise Miotti Tonin, Carolina Maso Viegas, Carmen Regla Vargas, Guilhian Leipnitz, César Augusto João Ribeiro, Moacir Wajner. Marked inhibition of Na+, K(+)- ATPase activity and the respiratory chain by phytanic acid in cerebellum from young rats: possible underlying mechanisms of cerebellar ataxia in Refsum disease. Journal of bioenergetics and biomembranes. 2013 Feb; 45(1-2):137-44. doi: 10.1007/s10863-012-9491-7. [PMID: 23151916]
  • Milena Povolo, Valeria Pelizzola, Luigi Passolungo, Elisa Biazzi, Aldo Tava, Giovanna Contarini. Characterization of two Agrostis-Festuca alpine pastures and their influence on cheese composition. Journal of agricultural and food chemistry. 2013 Jan; 61(2):447-55. doi: 10.1021/jf304756w. [PMID: 23259614]
  • Mohamed M Elmazar, Hanan S El-Abhar, Mona F Schaalan, Nahla A Farag. Phytol/Phytanic acid and insulin resistance: potential role of phytanic acid proven by docking simulation and modulation of biochemical alterations. PloS one. 2013; 8(1):e45638. doi: 10.1371/journal.pone.0045638. [PMID: 23300941]
  • Hugh J McMillan, Thea Worthylake, Jeremy Schwartzentruber, Chloe C Gottlieb, Sarah E Lawrence, Alex Mackenzie, Chandree L Beaulieu, Petra A W Mooyer, Ronald J A Wanders, Jacek Majewski, Dennis E Bulman, Michael T Geraghty, Sacha Ferdinandusse, Kym M Boycott. Specific combination of compound heterozygous mutations in 17β-hydroxysteroid dehydrogenase type 4 (HSD17B4) defines a new subtype of D-bifunctional protein deficiency. Orphanet journal of rare diseases. 2012 Nov; 7(?):90. doi: 10.1186/1750-1172-7-90. [PMID: 23181892]
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