(R)-5-Diphosphomevalonic acid (BioDeep_00000004590)

 

Secondary id: BioDeep_00000027737, BioDeep_00001868878

human metabolite Endogenous


代谢物信息卡片


(3r)-3-Hydroxy-5-{[(R)-Hydroxy(Phosphonooxy)phosphoryl]oxy}-3-Methylpentanoic Acid

化学式: C6H14O10P2 (308.0062204)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.11%

分子结构信息

SMILES: CC(CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O)O
InChI: InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1

描述信息

Mevalonate-diphosphate, also known as 5-diphosphomevalonic acid or mevelonic acid-5-diphosphoric acid, is a member of the class of compounds known as organic pyrophosphates. Organic pyrophosphates are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Thus, mevalonate-diphosphate is considered to be a fatty acid lipid molecule. Mevalonate-diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Mevalonate-diphosphate can be found in a number of food items such as kohlrabi, enokitake, avocado, and redcurrant, which makes mevalonate-diphosphate a potential biomarker for the consumption of these food products. Mevalonate-diphosphate exists in all eukaryotes, ranging from yeast to humans. In humans, mevalonate-diphosphate is involved in several metabolic pathways, some of which include zoledronate action pathway, lovastatin action pathway, pamidronate action pathway, and desmosterolosis. Mevalonate-diphosphate is also involved in several metabolic disorders, some of which include wolman disease, lysosomal acid lipase deficiency (wolman disease), cholesteryl ester storage disease, and CHILD syndrome.
5-Diphosphomevalonic acid (CAS: 1492-08-6) is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme phosphomevalonate kinase from 5-phosphomevalonate (Wikipedia).

同义名列表

28 个代谢物同义名

(3r)-3-Hydroxy-5-{[(R)-Hydroxy(Phosphonooxy)phosphoryl]oxy}-3-Methylpentanoic Acid; (3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoic acid; (3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid; (3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoate; Mevalonic acid 5-pyrophosphic acid; Mevalonic acid pyrophosphic acid; Mevalonic acid 5-diphosphic acid; Mevalonic acid 5-pyrophosphate; Mevalonic 5-pyrophosphic acid; (R)-5-Diphosphomevalonic acid; Mevalonic acid pyrophosphate; Mevalonic acid 5-diphosphate; 5-Pyrophosphomevalonic acid; (R)-Diphosphomevalonic acid; (RS)-5-diphosphomevalonate; Mevalonate 5-pyrophosphate; 5-Diphosphomevalonic acid; Mevalonic 5-pyrophosphate; (R)-5-Diphosphomevalonate; Pyrophosphomevalonic acid; Mevalonate 5-diphosphate; Mevalonate pyrophosphate; 5-Pyrophosphomevalonate; (R)-Diphosphomevalonate; Mevalonate-diphosphate; Pyrophosphomevalonate; 5-Diphosphomevalonate; R-Diphosphomevalonate



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(10)

BioCyc(1)

PlantCyc(0)

代谢反应

458 个相关的代谢反应过程信息。

Reactome(170)

BioCyc(5)

WikiPathways(3)

Plant Reactome(225)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(54)

PharmGKB(0)

5 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

  • Shakeel J Abbassi, Rishi K Vishwakarma, Parth Patel, Uma Kumari, Bashir M Khan. Bacopa monniera recombinant mevalonate diphosphate decarboxylase: Biochemical characterization. International journal of biological macromolecules. 2015 Aug; 79(?):661-8. doi: 10.1016/j.ijbiomac.2015.05.041. [PMID: 26027607]
  • 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]
  • 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]
  • 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]
  • Chao Tan, Hui Wang, Yue Zhang, Bin Qi, Guoxin Xu, Huiqiong Zheng. A proteomic approach to analyzing responses of Arabidopsis thaliana root cells to different gravitational conditions using an agravitropic mutant, pin2 and its wild type. Proteome science. 2011 Nov; 9(?):72. doi: 10.1186/1477-5956-9-72. [PMID: 22085406]
  • 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]
  • Ching-Wei Chang, Frederick A Beland, Wade M Hines, James C Fuscoe, Tao Han, James J Chen. Identification and categorization of liver toxicity markers induced by a related pair of drugs. International journal of molecular sciences. 2011; 12(7):4609-24. doi: 10.3390/ijms12074609. [PMID: 21845099]
  • Anthony L Schilmiller, Dennis P Miner, Matthew Larson, Eric McDowell, David R Gang, Curtis Wilkerson, Robert L Last. Studies of a biochemical factory: tomato trichome deep expressed sequence tag sequencing and proteomics. Plant physiology. 2010 Jul; 153(3):1212-23. doi: 10.1104/pp.110.157214. [PMID: 20431087]
  • 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]
  • L E Harrison, D C Wojciechowicz, M F Brennan, P B Paty. Phenylacetate inhibits isoprenoid biosynthesis and suppresses growth of human pancreatic carcinoma. Surgery. 1998 Sep; 124(3):541-50. doi: . [PMID: 9736908]
  • 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]
  • J A Cuthbert, P E Lipsky. Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. The Journal of biological chemistry. 1990 Oct; 265(30):18568-75. doi: . [PMID: 2211719]
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