3-Hydroxy-3-methylglutaryl-CoA (BioDeep_00000004418)

 

Secondary id: BioDeep_00001868804

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid

化学式: C27H44N7O20P3S (911.1574614)
中文名称: 三羟基三甲基戊二酸单酰辅酶A
谱图信息: 最多检出来源 Macaca mulatta(otcml) 8.79%

分子结构信息

SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)CC(C)(CC(=O)O)O)O
InChI: InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)

描述信息

3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582).
(s)-3-hydroxy-3-methylglutaryl-coa, also known as hmg-coa or hydroxymethylglutaroyl coenzyme a, is a member of the class of compounds known as (s)-3-hydroxy-3-alkylglutaryl coas (s)-3-hydroxy-3-alkylglutaryl coas are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration. Thus, (s)-3-hydroxy-3-methylglutaryl-coa is considered to be a fatty ester lipid molecule (s)-3-hydroxy-3-methylglutaryl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). (s)-3-hydroxy-3-methylglutaryl-coa can be found in a number of food items such as watercress, burdock, spirulina, and chicory, which makes (s)-3-hydroxy-3-methylglutaryl-coa a potential biomarker for the consumption of these food products (s)-3-hydroxy-3-methylglutaryl-coa may be a unique S.cerevisiae (yeast) metabolite.

同义名列表

25 个代谢物同义名

(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid; S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A; beta-Hydroxy-beta-methylglutaryl-coenzyme A; (3S)-3-Hydroxy-3-methylglutaryl-coenzyme A; (S)-3-Hydroxy-3-methylglutaryl-coenzyme A; (S)-3-Hydroxy-3-methylglutaryl coenzyme A; Β-hydroxy-β-methylglutaryl-coenzyme A; 3-Hydroxy-3-methylglutaryl coenzyme A; beta-Hydroxy-beta-methylglutaryl CoA; beta-Hydroxy-beta-methylglutaryl-CoA; (3S)-3-hydroxy-3-methylglutaryl-CoA; (S)-3-Hydroxy-3-methylglutaryl-CoA; Hydroxymethylglutaroyl coenzyme A; Hydroxymethylglutaryl coenzyme A; 3 Hydroxy-3-methylglutaryl CoA; Β-hydroxy-β-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl-CoA; 3-Hydroxy-3-methylglutaryl CoA; b-Hydroxy-b-methylglutaryl CoA; Β-hydroxy-β-methylglutaryl-CoA; Hydroxymethylglutaryl CoA; Hydroxymethylglutaryl-CoA; HMG-coenzyme A; HMG-CoA; 3-Hydroxy-3-methyl-Glutaryl-CoA



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(2)

BioCyc(1)

PlantCyc(0)

代谢反应

337 个相关的代谢反应过程信息。

Reactome(80)

BioCyc(5)

WikiPathways(12)

Plant Reactome(234)

INOH(5)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(0)

PharmGKB(0)

7 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

  • Jianqiu Wang, Markus Kunze, Andrea Villoria-González, Isabelle Weinhofer, Johannes Berger. Peroxisomal Localization of a Truncated HMG-CoA Reductase under Low Cholesterol Conditions. Biomolecules. 2024 Feb; 14(2):. doi: 10.3390/biom14020244. [PMID: 38397481]
  • Xiao-Zheng Su, Lin-Fei Zhang, Kun Hu, Yang An, Qiao-Peng Zhang, Jian-Wei Tang, Bing-Chao Yan, Xing-Ren Li, Jie Cai, Xiao-Nian Li, Han-Dong Sun, Shi-You Jiang, Pema-Tenzin Puno. Discovery of Natural Potent HMG-CoA Reductase Degraders for Lowering Cholesterol. Angewandte Chemie (International ed. in English). 2024 Feb; 63(6):e202313859. doi: 10.1002/anie.202313859. [PMID: 38055195]
  • You Bin Cho, Hyunbeom Lee, Hui-Jeon Jeon, Jae Yeol Lee, Hyoung Ja Kim. Antioxidant and Inhibitory Activities of Filipendula glaberrima Leaf Constituents against HMG-CoA Reductase and Macrophage Foam Cell Formation. Molecules (Basel, Switzerland). 2024 Jan; 29(2):. doi: 10.3390/molecules29020354. [PMID: 38257267]
  • Dan Xie, Lijun Song, Dongyang Xiang, Xiangyu Gao, Wenchang Zhao. Salvianolic acid A alleviates atherosclerosis by inhibiting inflammation through Trc8-mediated 3-hydroxy-3-methylglutaryl-coenzyme A reductase degradation. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Feb; 112(?):154694. doi: 10.1016/j.phymed.2023.154694. [PMID: 36804757]
  • Janani Balraj, Thandeeswaran Murugesan, Anand Raj Dhanapal, Vidhya Kalieswaran, Karunyadevi Jairaman, Govindaraju Archunan, Angayarkanni Jayaraman. Bioconversion of lovastatin to simvastatin by Streptomyces carpaticus toward the inhibition of HMG-CoA activity. Biotechnology and applied biochemistry. 2022 Dec; ?(?):. doi: 10.1002/bab.2429. [PMID: 36524308]
  • Michalina Zaborowska, Dorota Matyszewska, Renata Bilewicz. Model Lipid Raft Membranes for Embedding Integral Membrane Proteins: Reconstitution of HMG-CoA Reductase and Its Inhibition by Statins. Langmuir : the ACS journal of surfaces and colloids. 2022 11; 38(45):13888-13897. doi: 10.1021/acs.langmuir.2c02115. [PMID: 36335466]
  • Joel Haywood, Karen J Breese, Jingjing Zhang, Mark T Waters, Charles S Bond, Keith A Stubbs, Joshua S Mylne. A fungal tolerance trait and selective inhibitors proffer HMG-CoA reductase as a herbicide mode-of-action. Nature communications. 2022 09; 13(1):5563. doi: 10.1038/s41467-022-33185-0. [PMID: 36137996]
  • Daniel B Rosoff, Andrew S Bell, Jeesun Jung, Josephin Wagner, Lucas A Mavromatis, Falk W Lohoff. Mendelian Randomization Study of PCSK9 and HMG-CoA Reductase Inhibition and Cognitive Function. Journal of the American College of Cardiology. 2022 08; 80(7):653-662. doi: 10.1016/j.jacc.2022.05.041. [PMID: 35953131]
  • Małgorzata Majewska, Piotr Szymczyk, Jan Gomulski, Agnieszka Jeleń, Renata Grąbkowska, Ewa Balcerczak, Łukasz Kuźma. The Expression Profiles of the Salvia miltiorrhiza 3-Hydroxy-3-methylglutaryl-coenzyme A Reductase 4 Gene and Its Influence on the Biosynthesis of Tanshinones. Molecules (Basel, Switzerland). 2022 Jul; 27(14):. doi: 10.3390/molecules27144354. [PMID: 35889227]
  • Alexandria M Doerfler, Jun Han, Kelsey E Jarrett, Li Tang, Antrix Jain, Alexander Saltzman, Marco De Giorgi, Marcel Chuecos, Ayrea E Hurley, Ang Li, Pauline Morand, Claudia Ayala, David R Goodlett, Anna Malovannaya, James F Martin, Thomas Q de Aguiar Vallim, Noah Shroyer, William R Lagor. Intestinal Deletion of 3-Hydroxy-3-Methylglutaryl-Coenzyme A Reductase Promotes Expansion of the Resident Stem Cell Compartment. Arteriosclerosis, thrombosis, and vascular biology. 2022 04; 42(4):381-394. doi: 10.1161/atvbaha.122.317320. [PMID: 35172604]
  • Jaykaran Charan, Priyanka Riyad, Heera Ram, Ashok Purohit, Sneha Ambwani, Priya Kashyap, Garima Singh, Abeer Hashem, Elsayed Fathi Abd Allah, Vijai Kumar Gupta, Ashok Kumar, Anil Panwar. Ameliorations in dyslipidemia and atherosclerotic plaque by the inhibition of HMG-CoA reductase and antioxidant potential of phytoconstituents of an aqueous seed extract of Acacia senegal (L.) Willd in rabbits. PloS one. 2022; 17(3):e0264646. doi: 10.1371/journal.pone.0264646. [PMID: 35239727]
  • Ching-Pei Chen, Kuei-Chuan Chan, Hsieh-Hsun Ho, Hui-Pei Huang, Li-Sung Hsu, Chau-Jong Wang. Mulberry polyphenol extracts attenuated senescence through inhibition of Ras/ERK via promoting Ras degradation in VSMC. International journal of medical sciences. 2022; 19(1):89-97. doi: 10.7150/ijms.64763. [PMID: 34975302]
  • Damilohun Samuel Metibemu, Oluseyi Adeboye Akinloye, Adio Jamiu Akamo, Jude Ogechukwu Okoye, Idowu Olaposi Omotuyi. In-silico HMG-CoA reductase-inhibitory and in-vivo anti-lipidaemic/anticancer effects of carotenoids from Spondias mombin. The Journal of pharmacy and pharmacology. 2021 Sep; 73(10):1377-1386. doi: 10.1093/jpp/rgab103. [PMID: 34343336]
  • Shanshan Zhong, Luxiao Li, Ningning Liang, Lili Zhang, Xiaodong Xu, Shiting Chen, Huiyong Yin. Acetaldehyde Dehydrogenase 2 regulates HMG-CoA reductase stability and cholesterol synthesis in the liver. Redox biology. 2021 05; 41(?):101919. doi: 10.1016/j.redox.2021.101919. [PMID: 33740503]
  • Jingbo Ma, Yang Gu, Monireh Marsafari, Peng Xu. Synthetic biology, systems biology, and metabolic engineering of Yarrowia lipolytica toward a sustainable biorefinery platform. Journal of industrial microbiology & biotechnology. 2020 Oct; 47(9-10):845-862. doi: 10.1007/s10295-020-02290-8. [PMID: 32623653]
  • Liwen Wu, Yunxiao Zhao, Qiyan Zhang, Yicun Chen, Ming Gao, Yangdong Wang. Overexpression of the 3-hydroxy-3-methylglutaryl-CoA synthase gene LcHMGS effectively increases the yield of monoterpenes and sesquiterpenes. Tree physiology. 2020 07; 40(8):1095-1107. doi: 10.1093/treephys/tpaa045. [PMID: 32325486]
  • Marwa M Abd-Rabo, Lobna F Wahman, Rania El Hosary, Iman S Ahmed. High-fat diet induced alteration in lipid enzymes and inflammation in cardiac and brain tissues: Assessment of the effects of Atorvastatin-loaded nanoparticles. Journal of biochemical and molecular toxicology. 2020 May; 34(5):e22465. doi: 10.1002/jbt.22465. [PMID: 32048413]
  • Maria Giovanna Lupo, Noemi Biancorosso, Elisa Brilli, Germano Tarantino, Maria Pia Adorni, Greta Vivian, Marika Salvalaio, Stefano Dall'Acqua, Stefania Sut, Cédric Neutel, Haixia Chen, Alessandro Bressan, Elisabetta Faggin, Marcello Rattazzi, Nicola Ferri. Cholesterol-Lowering Action of a Novel Nutraceutical Combination in Uremic Rats: Insights into the Molecular Mechanism in a Hepatoma Cell Line. Nutrients. 2020 Feb; 12(2):. doi: 10.3390/nu12020436. [PMID: 32050453]
  • Muthukumaran Jayachandran, Tongze Zhang, Ziyuan Wu, Yinhua Liu, Baojun Xu. Isoquercetin regulates SREBP-1C via AMPK pathway in skeletal muscle to exert antihyperlipidemic and anti-inflammatory effects in STZ induced diabetic rats. Molecular biology reports. 2020 Jan; 47(1):593-602. doi: 10.1007/s11033-019-05166-y. [PMID: 31677037]
  • Min Zhang, Heng Liu, Qing Wang, Shaohua Liu, Yuanhu Zhang. The 3-hydroxy-3-methylglutaryl-coenzyme A reductase 5 gene from Malus domestica enhances oxidative stress tolerance in Arabidopsis thaliana. Plant physiology and biochemistry : PPB. 2020 Jan; 146(?):269-277. doi: 10.1016/j.plaphy.2019.11.031. [PMID: 31783202]
  • Baskaran Gunasekaran, Mohd Yunus Shukor. HMG-CoA Reductase as Target for Drug Development. Methods in molecular biology (Clifton, N.J.). 2020; 2089(?):245-250. doi: 10.1007/978-1-0716-0163-1_16. [PMID: 31773659]
  • Andréa Hemmerlin, Alexandre Huchelmann, Denis Tritsch, Hubert Schaller, Thomas J Bach. The specific molecular architecture of plant 3-hydroxy-3-methylglutaryl-CoA lyase. The Journal of biological chemistry. 2019 11; 294(44):16186-16197. doi: 10.1074/jbc.ra119.008839. [PMID: 31515272]
  • Hao Liu, Jing-Kun Miao, Chao-Wen Yu, Ke-Xing Wan, Juan Zhang, Zhao-Jian Yuan, Jing Yang, Dong-Juan Wang, Yan Zeng, Lin Zou. Severe clinical manifestation of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase deficiency associated with two novel mutations: a case report. BMC pediatrics. 2019 10; 19(1):344. doi: 10.1186/s12887-019-1747-5. [PMID: 31597564]
  • Shen Rao, Xiangxiang Meng, Yongling Liao, Tian Yu, Jie Cao, Junping Tan, Feng Xu, Shuiyuan Cheng. Characterization and functional analysis of two novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase genes (GbHMGR2 and GbHMGR3) from Ginkgo biloba. Scientific reports. 2019 Oct; 9(1):14109. doi: 10.1038/s41598-019-50629-8. [PMID: 31575936]
  • Hudson W Coates, Andrew J Brown. A wolf in sheep's clothing: unmasking the lanosterol-induced degradation of HMG-CoA reductase. Journal of lipid research. 2019 10; 60(10):1643-1645. doi: 10.1194/jlr.c119000358. [PMID: 31462514]
  • Zhenzhou Zhu, Yuqi Huang, Xiao Luo, Qian Wu, Jingren He, Shuyi Li, Francisco J Barba. Modulation of lipid metabolism and colonic microbial diversity of high-fat-diet C57BL/6 mice by inulin with different chain lengths. Food research international (Ottawa, Ont.). 2019 09; 123(?):355-363. doi: 10.1016/j.foodres.2019.05.003. [PMID: 31284986]
  • Ying Lu, Yingjie He, Shihao Zhu, Xiaohong Zhong, Dong Chen, Zhonghua Liu. New Acylglycosides Flavones from Fuzhuan Brick Tea and Simulation Analysis of Their Bioactive Effects. International journal of molecular sciences. 2019 Jan; 20(3):. doi: 10.3390/ijms20030494. [PMID: 30678336]
  • Hangjun Zhang, Jianbo He, Ning Li, Nana Gao, Qiongxia Du, Bin Chen, Feifei Chen, Xiaodong Shan, Ying Ding, Weiqin Zhu, Yingzhu Wu, Juan Tang, Xiuying Jia. Lipid accumulation responses in the liver of Rana nigromaculata induced by perfluorooctanoic acid (PFOA). Ecotoxicology and environmental safety. 2019 Jan; 167(?):29-35. doi: 10.1016/j.ecoenv.2018.09.120. [PMID: 30292973]
  • Pragya Bhardwaj, Navendu Goswami, Pankhuri Narula, Chakresh Kumar Jain, Ashwani Mathur. Zinc oxide nanoparticles (ZnO NP) mediated regulation of bacosides biosynthesis and transcriptional correlation of HMG-CoA reductase gene in suspension culture of Bacopa monnieri. Plant physiology and biochemistry : PPB. 2018 Sep; 130(?):148-156. doi: 10.1016/j.plaphy.2018.07.001. [PMID: 29982171]
  • Vasanth Sathiyakumar, Karan Kapoor, Steven R Jones, Maciej Banach, Seth S Martin, Peter P Toth. Novel Therapeutic Targets for Managing Dyslipidemia. Trends in pharmacological sciences. 2018 08; 39(8):733-747. doi: 10.1016/j.tips.2018.06.001. [PMID: 29970260]
  • Aslaug Drotningsvik, Linn Anja Vikøren, Svein Are Mjøs, Åge Oterhals, Daniela Pampanin, Ola Flesland, Oddrun Anita Gudbrandsen. Water-Soluble Fish Protein Intake Led to Lower Serum and Liver Cholesterol Concentrations in Obese Zucker fa/fa Rats. Marine drugs. 2018 May; 16(5):. doi: 10.3390/md16050149. [PMID: 29724010]
  • Shilpi Bansal, Lokesh Kumar Narnoliya, Bhawana Mishra, Muktesh Chandra, Ritesh Kumar Yadav, Neelam Singh Sangwan. HMG-CoA reductase from Camphor Tulsi (Ocimum kilimandscharicum) regulated MVA dependent biosynthesis of diverse terpenoids in homologous and heterologous plant systems. Scientific reports. 2018 02; 8(1):3547. doi: 10.1038/s41598-017-17153-z. [PMID: 29476116]
  • Elena V Efimova, Natalia Ricco, Edwardine Labay, Helena J Mauceri, Amy C Flor, Aishwarya Ramamurthy, Harold G Sutton, Ralph R Weichselbaum, Stephen J Kron. HMG-CoA Reductase Inhibition Delays DNA Repair and Promotes Senescence After Tumor Irradiation. Molecular cancer therapeutics. 2018 02; 17(2):407-418. doi: 10.1158/1535-7163.mct-17-0288. [PMID: 29030460]
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  • Asma Ressaissi, Nebil Attia, Pedro Luis Falé, Rita Pacheco, Bruno L Victor, Miguel Machuqueiro, Maria Luísa M Serralheiro. Isorhamnetin derivatives and piscidic acid for hypercholesterolemia: cholesterol permeability, HMG-CoA reductase inhibition, and docking studies. Archives of pharmacal research. 2017 Nov; 40(11):1278-1286. doi: 10.1007/s12272-017-0959-1. [PMID: 28936788]
  • Ja-Jen Chang, Dai-Jung Chung, Yi-Ju Lee, Bo-Han Wen, Hsing-Yu Jao, Chau-Jong Wang. Solanum nigrum Polyphenol Extracts Inhibit Hepatic Inflammation, Oxidative Stress, and Lipogenesis in High-Fat-Diet-Treated Mice. Journal of agricultural and food chemistry. 2017 Oct; 65(42):9255-9265. doi: 10.1021/acs.jafc.7b03578. [PMID: 28982243]
  • Xiangxiang Meng, Qiling Song, Jiabao Ye, Lanlan Wang, Feng Xu. Characterization, Function, and Transcriptional Profiling Analysis of 3-Hydroxy-3-methylglutaryl-CoA Synthase Gene (GbHMGS1) towards Stresses and Exogenous Hormone Treatments in Ginkgo biloba. Molecules (Basel, Switzerland). 2017 Oct; 22(10):. doi: 10.3390/molecules22101706. [PMID: 29023415]
  • Troy D Jaskowski, Sonia L La'ulu, Michael Mahler, Anne E Tebo. Detection of autoantibodies to 3-hydroxy-3-methylglutaryl-coenzyme a reductase by ELISA in a reference laboratory setting. Clinica chimica acta; international journal of clinical chemistry. 2017 Sep; 472(?):30-34. doi: 10.1016/j.cca.2017.07.011. [PMID: 28709800]
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