Mevalonic acid-5P (BioDeep_00000004574)

 

Secondary id: BioDeep_00000182382, BioDeep_00001869060

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid

化学式: C6H13O7P (228.0398878)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 1.11%

分子结构信息

SMILES: CC(CCOP(=O)(O)O)(CC(=O)O)O
InChI: InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)

描述信息

Mevalonic acid-5p, also known as (R)-5-phosphomevalonate or mevalonate-5p, is a member of the class of compounds known as monoalkyl phosphates. Monoalkyl phosphates are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Thus, mevalonic acid-5p is considered to be a fatty acid lipid molecule. Mevalonic acid-5p is soluble (in water) and a moderately acidic compound (based on its pKa). Mevalonic acid-5p can be found in a number of food items such as rowanberry, common oregano, caraway, and cherry tomato, which makes mevalonic acid-5p a potential biomarker for the consumption of these food products. Mevalonic acid-5p can be found primarily throughout most human tissues. Mevalonic acid-5p exists in all eukaryotes, ranging from yeast to humans. In humans, mevalonic acid-5p is involved in several metabolic pathways, some of which include pamidronate action pathway, rosuvastatin action pathway, pravastatin action pathway, and lovastatin action pathway. Mevalonic acid-5p is also involved in several metabolic disorders, some of which include hypercholesterolemia, lysosomal acid lipase deficiency (wolman disease), hyper-igd syndrome, and mevalonic aciduria.
Mevalonic acid-5P (CAS: 1189-94-2), also known as 5-phosphomevalonic acid, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Within humans, mevalonic acid-5P participates in many enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonate; which is mediated by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into mevalonic acid-5-pyrophosphate through its interaction with the enzyme phosphomevalonate kinase. In humans, mevalonic acid-5P is involved in the mevalonate pathway. Outside of the human body, mevalonic acid-5P has been detected, but not quantified in, several different foods, such as oriental wheat, devilfish, pepper (spice), redcurrants, and star fruits. This could make mevalonic acid-5P a potential biomarker for the consumption of these foods.

同义名列表

23 个代谢物同义名

(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid; 3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid; 3-Hydroxy-3-methyl-5-phosphonooxypentanoic acid; (R)-Mevalonic acid 5-phosphoric acid; Phosphomevalonic acid, (+-)-isomer; (R)-Mevalonic acid 5-phosphate; (R)-5-Phosphomevaloonic acid; (R)-5-Phosphomevalonic acid; (R)-Mevalonate 5-phosphate; Mevalonic acid phosphate; (R)-5-Phosphomevaloonate; (R)-5-Phosphomevalonate; 5-Phosphomevalonic acid; Mevalonate-5-phosphate; Mevalonate 5-phosphate; Phosphomevalonic acid; 5-Phosphomevalonate; Mevalonic acid-5P; Phosphomevalonate; Mevalonate-5-p; Mevalonate-5P; p-Mevalonate; Mevalonate-P



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

291 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(5)

WikiPathways(4)

Plant Reactome(213)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(56)

PharmGKB(0)

3 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

  • Daniel P Duarte, Éden R Ferreira, Fabio M Lima, Franciane Batista, Michel De Groote, Eduardo Horjales, Luiz C Miletti, Diana Bahia. Molecular Characterization of Trypanosoma evansi Mevalonate Kinase (TeMVK). Frontiers in cellular and infection microbiology. 2018; 8(?):223. doi: 10.3389/fcimb.2018.00223. [PMID: 30042928]
  • Grégory Guirimand, Andrew John Simkin, Nicolas Papon, Sébastien Besseau, Vincent Burlat, Benoit St-Pierre, Nathalie Giglioli-Guivarc'h, Marc Clastre, Vincent Courdavault. Cycloheximide as a tool to investigate protein import in peroxisomes: a case study of the subcellular localization of isoprenoid biosynthetic enzymes. Journal of plant physiology. 2012 May; 169(8):825-9. doi: 10.1016/j.jplph.2012.01.020. [PMID: 22459325]
  • Yimian Ma, Lichai Yuan, Bin Wu, Xian'en Li, Shilin Chen, Shanfa Lu. Genome-wide identification and characterization of novel genes involved in terpenoid biosynthesis in Salvia miltiorrhiza. Journal of experimental botany. 2012 Apr; 63(7):2809-23. doi: 10.1093/jxb/err466. [PMID: 22291132]
  • Keng-See Chow, Mohd-Noor Mat-Isa, Azlina Bahari, Ahmad-Kamal Ghazali, Halimah Alias, Zainorlina Mohd-Zainuddin, Chee-Choong Hoh, Kiew-Lian Wan. Metabolic routes affecting rubber biosynthesis in Hevea brasiliensis latex. Journal of experimental botany. 2012 Mar; 63(5):1863-71. doi: 10.1093/jxb/err363. [PMID: 22162870]
  • Sol A Green, Xiuyin Chen, Niels J Nieuwenhuizen, Adam J Matich, Mindy Y Wang, Barry J Bunn, Yar-Khing Yauk, Ross G Atkinson. Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). Journal of experimental botany. 2012 Mar; 63(5):1951-67. doi: 10.1093/jxb/err393. [PMID: 22162874]
  • LingLin Wan, Juan Han, Min Sang, AiFen Li, Hong Wu, ShunJi Yin, ChengWu Zhang. De novo transcriptomic analysis of an oleaginous microalga: pathway description and gene discovery for production of next-generation biofuels. PloS one. 2012; 7(4):e35142. doi: 10.1371/journal.pone.0035142. [PMID: 22536352]
  • Tahira Fatima, Crystal L Snyder, William R Schroeder, Dustin Cram, Raju Datla, David Wishart, Randall J Weselake, Priti Krishna. Fatty acid composition of developing sea buckthorn (Hippophae rhamnoides L.) berry and the transcriptome of the mature seed. PloS one. 2012; 7(4):e34099. doi: 10.1371/journal.pone.0034099. [PMID: 22558083]
  • Hongmei Luo, Chao Sun, Yongzhen Sun, Qiong Wu, Ying Li, Jingyuan Song, Yunyun Niu, Xianglin Cheng, Hongxi Xu, Chuyuan Li, Juyan Liu, André Steinmetz, Shilin Chen. Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin-biosynthetic genes and genetic markers. BMC genomics. 2011 Dec; 12 Suppl 5(?):S5. doi: 10.1186/1471-2164-12-s5-s5. [PMID: 22369100]
  • Roberto A Barrero, Brett Chapman, Yanfang Yang, Paula Moolhuijzen, Gabriel Keeble-Gagnère, Nan Zhang, Qi Tang, Matthew I Bellgard, Deyou Qiu. De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes. BMC genomics. 2011 Dec; 12(?):600. doi: 10.1186/1471-2164-12-600. [PMID: 22151917]
  • Marc Clastre, Nicolas Papon, Vincent Courdavault, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Andrew J Simkin. Subcellular evidence for the involvement of peroxisomes in plant isoprenoid biosynthesis. Plant signaling & behavior. 2011 Dec; 6(12):2044-6. doi: 10.4161/psb.6.12.18173. [PMID: 22080790]
  • Chun Sui, Jie Zhang, Jianhe Wei, Shilin Chen, Ying Li, Jiesen Xu, Yue Jin, Caixiang Xie, Zhihui Gao, Hongjiang Chen, Chengmin Yang, Zheng Zhang, Yanhong Xu. Transcriptome analysis of Bupleurum chinense focusing on genes involved in the biosynthesis of saikosaponins. BMC genomics. 2011 Nov; 12(?):539. doi: 10.1186/1471-2164-12-539. [PMID: 22047182]
  • Andrew J Simkin, Grégory Guirimand, Nicolas Papon, Vincent Courdavault, Insaf Thabet, Olivia Ginis, Sadok Bouzid, Nathalie Giglioli-Guivarc'h, Marc Clastre. Peroxisomal localisation of the final steps of the mevalonic acid pathway in planta. Planta. 2011 Nov; 234(5):903-14. doi: 10.1007/s00425-011-1444-6. [PMID: 21655959]
  • Qi Tang, Xiaojun Ma, Changming Mo, Iain W Wilson, Cai Song, Huan Zhao, Yanfang Yang, Wei Fu, Deyou Qiu. An efficient approach to finding Siraitia grosvenorii triterpene biosynthetic genes by RNA-seq and digital gene expression analysis. BMC genomics. 2011 Jul; 12(?):343. doi: 10.1186/1471-2164-12-343. [PMID: 21729270]
  • Pilar Martinez-Moya, Steven Alexander Watt, Karsten Niehaus, Jennifer Alcaíno, Marcelo Baeza, Víctor Cifuentes. Proteomic analysis of the carotenogenic yeast Xanthophyllomyces dendrorhous. BMC microbiology. 2011 Jun; 11(?):131. doi: 10.1186/1471-2180-11-131. [PMID: 21669001]
  • Linda Olofsson, Alexander Engström, Anneli Lundgren, Peter E Brodelius. Relative expression of genes of terpene metabolism in different tissues of Artemisia annua L. BMC plant biology. 2011 Mar; 11(?):45. doi: 10.1186/1471-2229-11-45. [PMID: 21388533]
  • Rayko Becher, Fabian Weihmann, Holger B Deising, Stefan Gr Wirsel. Development of a novel multiplex DNA microarray for Fusarium graminearum and analysis of azole fungicide responses. BMC genomics. 2011 Jan; 12(?):52. doi: 10.1186/1471-2164-12-52. [PMID: 21255412]
  • Lei Wang, Wei Chen, Yun Feng, Yan Ren, Zhennan Gu, Haiqin Chen, Hongchao Wang, Michael J Thomas, Baixi Zhang, Isabelle M Berquin, Yang Li, Jiansheng Wu, Huanxin Zhang, Yuanda Song, Xiang Liu, James S Norris, Suriguga Wang, Peng Du, Junguo Shen, Na Wang, Yanlin Yang, Wei Wang, Lu Feng, Colin Ratledge, Hao Zhang, Yong Q Chen. Genome characterization of the oleaginous fungus Mortierella alpina. PloS one. 2011; 6(12):e28319. doi: 10.1371/journal.pone.0028319. [PMID: 22174787]
  • Lena Burri, Kjetil Berge, Karin Wibrand, Rolf K Berge, Jamie L Barger. Differential effects of krill oil and fish oil on the hepatic transcriptome in mice. Frontiers in genetics. 2011; 2(?):45. doi: 10.3389/fgene.2011.00045. [PMID: 22303341]
  • Lindsey R Boone, Patricia A Brooks, Melissa I Niesen, Gene C Ness. Mechanism of resistance to dietary cholesterol. Journal of lipids. 2011; 2011(?):101242. doi: 10.1155/2011/101242. [PMID: 22007308]
  • Wayne Chadwick, Randall Brenneman, Bronwen Martin, Stuart Maudsley. Complex and multidimensional lipid raft alterations in a murine model of Alzheimer's disease. International journal of Alzheimer's disease. 2010 Dec; 2010(?):604792. doi: 10.4061/2010/604792. [PMID: 21151659]
  • Ravi S Singh, Rishi K Gara, Pardeep K Bhardwaj, Anish Kaachra, Sonia Malik, Ravi Kumar, Madhu Sharma, Paramvir S Ahuja, Sanjay Kumar. Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston]. BMC molecular biology. 2010 Nov; 11(?):88. doi: 10.1186/1471-2199-11-88. [PMID: 21092138]
  • Diane M Martin, Sébastien Aubourg, Marina B Schouwey, Laurent Daviet, Michel Schalk, Omid Toub, Steven T Lund, Jörg Bohlmann. Functional annotation, genome organization and phylogeny of the grapevine (Vitis vinifera) terpene synthase gene family based on genome assembly, FLcDNA cloning, and enzyme assays. BMC plant biology. 2010 Oct; 10(?):226. doi: 10.1186/1471-2229-10-226. [PMID: 20964856]
  • Mitsuko Kishi-Kaboshi, Kazunori Okada, Leona Kurimoto, Shinya Murakami, Toshiaki Umezawa, Naoto Shibuya, Hisakazu Yamane, Akio Miyao, Hiroshi Takatsuji, Akira Takahashi, Hirohiko Hirochika. A rice fungal MAMP-responsive MAPK cascade regulates metabolic flow to antimicrobial metabolite synthesis. The Plant journal : for cell and molecular biology. 2010 Aug; 63(4):599-612. doi: 10.1111/j.1365-313x.2010.04264.x. [PMID: 20525005]
  • Chao Sun, Ying Li, Qiong Wu, Hongmei Luo, Yongzhen Sun, Jingyuan Song, Edmund M K Lui, Shilin Chen. De novo sequencing and analysis of the American ginseng root transcriptome using a GS FLX Titanium platform to discover putative genes involved in ginsenoside biosynthesis. BMC genomics. 2010 Apr; 11(?):262. doi: 10.1186/1471-2164-11-262. [PMID: 20416102]
  • Tsuyoshi Goto, Nobuyuki Takahashi, Shizuka Hirai, Teruo Kawada. Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism. PPAR research. 2010; 2010(?):483958. doi: 10.1155/2010/483958. [PMID: 20613991]
  • Jacob F de Wolff, Stephen J Dickinson, Alice C Smith, Karen Molyneux, John Feehally, Anna Simon, Jonathan Barratt. Abnormal IgD and IgA1 O-glycosylation in hyperimmunoglobulinaemia D and periodic fever syndrome. Clinical and experimental medicine. 2009 Dec; 9(4):291-6. doi: 10.1007/s10238-009-0056-y. [PMID: 19543954]
  • Kaijin Wu, Corrine Joffre, Xiaodong Li, Michelle MacVeigh-Aloni, Melinda Hom, Juliana Hwang, Chuanqing Ding, Stephane Gregoire, Lionel Bretillon, Jiang F Zhong, Sarah F Hamm-Alvarez. Altered expression of genes functioning in lipid homeostasis is associated with lipid deposition in NOD mouse lacrimal gland. Experimental eye research. 2009 Sep; 89(3):319-32. doi: 10.1016/j.exer.2009.03.020. [PMID: 19345210]
  • Ting Yang, Liron Bar-Peled, Lindsay Gebhart, Sung G Lee, Maor Bar-Peled. Identification of galacturonic acid-1-phosphate kinase, a new member of the GHMP kinase superfamily in plants, and comparison with galactose-1-phosphate kinase. The Journal of biological chemistry. 2009 Aug; 284(32):21526-35. doi: 10.1074/jbc.m109.014761. [PMID: 19509290]
  • Marcello Iriti, Franco Faoro. Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution. International journal of molecular sciences. 2009 Jul; 10(8):3371-3399. doi: 10.3390/ijms10083371. [PMID: 20111684]
  • Hiroko Tsuruta, Christopher J Paddon, Diana Eng, Jacob R Lenihan, Tizita Horning, Larry C Anthony, Rika Regentin, Jay D Keasling, Neil S Renninger, Jack D Newman. High-level production of amorpha-4,11-diene, a precursor of the antimalarial agent artemisinin, in Escherichia coli. PloS one. 2009; 4(2):e4489. doi: 10.1371/journal.pone.0004489. [PMID: 19221601]
  • Xavier Argout, Olivier Fouet, Patrick Wincker, Karina Gramacho, Thierry Legavre, Xavier Sabau, Ange Marie Risterucci, Corinne Da Silva, Julio Cascardo, Mathilde Allegre, David Kuhn, Joseph Verica, Brigitte Courtois, Gaston Loor, Regis Babin, Olivier Sounigo, Michel Ducamp, Mark J Guiltinan, Manuel Ruiz, Laurence Alemanno, Regina Machado, Wilberth Phillips, Ray Schnell, Martin Gilmour, Eric Rosenquist, David Butler, Siela Maximova, Claire Lanaud. Towards the understanding of the cocoa transcriptome: Production and analysis of an exhaustive dataset of ESTs of Theobroma cacao L. generated from various tissues and under various conditions. BMC genomics. 2008 Oct; 9(?):512. doi: 10.1186/1471-2164-9-512. [PMID: 18973681]
  • Caroline Hild Jakobsen, Gro Leite Størvold, Hilde Bremseth, Turid Follestad, Kristin Sand, Merete Mack, Karina Standahl Olsen, Anne Gøril Lundemo, Jens Gustav Iversen, Hans Einar Krokan, Svanhild Arentz Schønberg. DHA induces ER stress and growth arrest in human colon cancer cells: associations with cholesterol and calcium homeostasis. Journal of lipid research. 2008 Oct; 49(10):2089-100. doi: 10.1194/jlr.m700389-jlr200. [PMID: 18566476]
  • Grace Flock, Laurie L Baggio, Christine Longuet, Daniel J Drucker. Incretin receptors for glucagon-like peptide 1 and glucose-dependent insulinotropic polypeptide are essential for the sustained metabolic actions of vildagliptin in mice. Diabetes. 2007 Dec; 56(12):3006-13. doi: 10.2337/db07-0697. [PMID: 17717280]
  • Jia Mi, Itsaso Garcia-Arcos, Ruben Alvarez, Susana Cristobal. Age-related subproteomic analysis of mouse liver and kidney peroxisomes. Proteome science. 2007 Nov; 5(?):19. doi: 10.1186/1477-5956-5-19. [PMID: 18042274]
  • Sietske Hogenboom, Gerrit Jan Romeijn, Sander M Houten, Myriam Baes, Ronald J A Wanders, Hans R Waterham. Absence of functional peroxisomes does not lead to deficiency of enzymes involved in cholesterol biosynthesis. Journal of lipid research. 2002 Jan; 43(1):90-8. doi: . [PMID: 11792727]
  • D D Hinson, K L Chambliss, M J Toth, R D Tanaka, K M Gibson. Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways. Journal of lipid research. 1997 Nov; 38(11):2216-23. doi: . [PMID: 9392419]
  • C Feyerabend, M A Russell. Improved gas chromatographic method and micro-extraction technique for the measurement of nicotine in biological fluids. The Journal of pharmacy and pharmacology. 1979 Feb; 31(2):73-6. doi: 10.1111/j.2042-7158.1979.tb13435.x. [PMID: 33255]
  • J S Charnock, A F Almeida, R To. Temperature-activity relationships of cation activation and ouabain inhibition of (Na+ + K+)-ATPase. Archives of biochemistry and biophysics. 1975 Apr; 167(2):480-7. doi: 10.1016/0003-9861(75)90490-7. [PMID: 123731]
  • M TADA, F LYNEN. [On the biosynthesis of terpenes. XIV. On the determination of phosphomevalonic acid kinase and pyrophosphomevalonic acid decarboxylase in cell extracts]. Journal of biochemistry. 1961 Jun; 49(?):758-64. doi: 10.1093/oxfordjournals.jbchem.a127368. [PMID: 13774769]
  • . . . . doi: . [PMID: 16519518]
  • . . . . doi: . [PMID: 14729858]