FA 5:0;O (BioDeep_00000629016)

Main id: BioDeep_00000017754

Secondary id: BioDeep_00000405265

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid

化学式: C5H10O3 (118.06299100000001)
中文名称: 3-羟基-2-甲基丁酸, 2-羟基-3-甲基丁酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.11%

分子结构信息

SMILES: C(=O)(O)C(C)C(O)C
InChI: InChI=1S/C5H10O3/c6-4-2-1-3-5(7)8/h6H,1-4H2,(H,7,8)

描述信息

2-Hydroxy-3-methylbutanoic acid is a close structure analogue of GHB, which is a naturally occurring neurotransmitter and a psychoactive agent.

同义名列表

32 个代谢物同义名

3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid; (2R,3R)-3-hydroxy-2-methylbutanoic acid; FA 5:0;O; 3-hydroxy-2-methyl-[R-(R,S)]-butanoic acid; (2S,3R)-3-hydroxy-2-methylbutanoic acid; 2-hydroxy-3-methylbutanoic acid; 2-Hydroxy-3-methylbutyric acid; 3-methyl-4-hydroxy-butanoic acid; 4-hydroxy-isovaleric acid; 3-hydroxy-3-methyl-butanoic acid; 3-hydroxy-isovaleric acid; 3S-hydroxy-2S-methyl-butanoic acid; 3R-hydroxy-2S-methyl-butanoic acid; 2-methyl-3-hydroxy-2-butanoic acid; 2-Methyl-3-hydroxybutyric acid; 2S-hydroxy-3-methyl-butanoic acid; 2-hydroxy-3-methyl-butyric acid; 2-hydroxy-2-methyl-butanoic acid; 2-hydroxy-2-methyl-butyric acid; 2-ethyl-3-hydroxy-propionic acid; 2-ethyl-hydracrylic acid; delta-hydrox yvaleric acid; 5-hydroxy-pentanoic acid; 5-hydroxy valeric acid; 4-hydroxy-pentanoic acid; 4-hydroxy-valeric acid; 3-ethyl hydroxy acrylic acid; 3-hydroxy-pentanoic acid; 3-hydroxy valeric acid; DL-2-hydroxy valeric acid; 2-hydroxy-pentanoic acid; 2-Hydroxy-3-methylbutyric acid



数据库引用编号

29 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)

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

  • Léo-Paul Bancel, Nicolas Germain, Anne-Sophie Guemann, Marie Joncquel Chevalier Curt, Anne-Frédérique Dessein. Abnormal Ketone Bodies in a 22-Month-Old Boy Presenting with Recurrent Vomiting and Metabolic Acidosis. Clinical chemistry. 2019 11; 65(11):1460-1462. doi: 10.1373/clinchem.2019.306712. [PMID: 31662337]
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  • Tao Sun, Ying Wu, Xueping Wu, Haifeng Ma. Metabolomic profiles investigation on athletes' urine 35 minutes after an 800-meter race. The Journal of sports medicine and physical fitness. 2017 Jun; 57(6):839-849. doi: 10.23736/s0022-4707.17.06254-5. [PMID: 26699119]
  • Hamza Mostafa, Arwa M Amin, Chin-Hoe Teh, Vikneswaran Murugaiyah, Nor Hayati Arif, Baharudin Ibrahim. Metabolic phenotyping of urine for discriminating alcohol-dependent from social drinkers and alcohol-naive subjects. Drug and alcohol dependence. 2016 Dec; 169(?):80-84. doi: 10.1016/j.drugalcdep.2016.10.016. [PMID: 27788404]
  • Toshiyuki Fukao, Kazuhisa Akiba, Masahiro Goto, Nobuki Kuwayama, Mikiko Morita, Tomohiro Hori, Yuka Aoyama, Rajaram Venkatesan, Rik Wierenga, Yohsuke Moriyama, Takashi Hashimoto, Nobuteru Usuda, Kei Murayama, Akira Ohtake, Yuki Hasegawa, Yosuke Shigematsu, Yukihiro Hasegawa. The first case in Asia of 2-methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency (HSD10 disease) with atypical presentation. Journal of human genetics. 2014 Nov; 59(11):609-14. doi: 10.1038/jhg.2014.79. [PMID: 25231369]
  • Su-Qing Qu, Li-Cai Yang, Zuo Luan, Kan Du, Hui Yang. [Acute encephalopathy due to late-onset maple syrup urine disease in a school boy]. Zhongguo dang dai er ke za zhi = Chinese journal of contemporary pediatrics. 2012 Mar; 14(3):161-4. doi: . [PMID: 22433398]
  • Vefik Arica, Secil Gunher Arica, Huseyin Dag, Hatice Onur, Omer Obut, Sayat Gülbayzar. Beta-ketothiolase deficiency brought with lethargy: case report. Human & experimental toxicology. 2011 Oct; 30(10):1724-7. doi: 10.1177/0960327110396533. [PMID: 21247997]
  • Ram Chandra, Ram Naresh Bharagava, Atya Kapley, Hemant J Purohit. Bacterial diversity, organic pollutants and their metabolites in two aeration lagoons of common effluent treatment plant (CETP) during the degradation and detoxification of tannery wastewater. Bioresource technology. 2011 Feb; 102(3):2333-41. doi: 10.1016/j.biortech.2010.10.087. [PMID: 21075615]
  • Laurie H Seaver, Xue-Ying He, Keith Abe, Tina Cowan, Gregory M Enns, Lawrence Sweetman, Manfred Philipp, Sansan Lee, Mazhar Malik, Song-Yu Yang. A novel mutation in the HSD17B10 gene of a 10-year-old boy with refractory epilepsy, choreoathetosis and learning disability. PloS one. 2011; 6(11):e27348. doi: 10.1371/journal.pone.0027348. [PMID: 22132097]
  • Chunfeng Lu, Yimei Wang, Zhiguo Sheng, Gang Liu, Ze Fu, Jing Zhao, Jun Zhao, Xianzhong Yan, Benzhan Zhu, Shuangqing Peng. NMR-based metabonomic analysis of the hepatotoxicity induced by combined exposure to PCBs and TCDD in rats. Toxicology and applied pharmacology. 2010 Nov; 248(3):178-84. doi: 10.1016/j.taap.2010.07.020. [PMID: 20691717]
  • Guilhian Leipnitz, Bianca Seminotti, Alexandre U Amaral, Carolina G Fernandes, Carlos S Dutra-Filho, Moacir Wajner. Evidence that 2-methylacetoacetate induces oxidative stress in rat brain. Metabolic brain disease. 2010 Sep; 25(3):261-7. doi: 10.1007/s11011-010-9204-z. [PMID: 20838866]
  • Alexandre Umpierrez Amaral, Guilhian Leipnitz, Carolina Gonçalves Fernandes, Bianca Seminotti, Patrícia Fernanda Schuck, Moacir Wajner. Alpha-ketoisocaproic acid and leucine provoke mitochondrial bioenergetic dysfunction in rat brain. Brain research. 2010 Apr; 1324(?):75-84. doi: 10.1016/j.brainres.2010.02.018. [PMID: 20153737]
  • V A Khripach, V N Zhabinskiĭ, K V Parkhimovich, O V Gyliakevich. [Synthesis of brassinolide and its biosynthetic precursors using methyl-3-hydroxy-2-methylpropionate]. Bioorganicheskaia khimiia. 2009 Mar; 35(2):260-9. doi: 10.1134/s1068162009020137. [PMID: 19537178]
  • Judit García-Villoria, Aleix Navarro-Sastre, Carme Fons, Celia Pérez-Cerdá, Antonio Baldellou, Miguel Angel Fuentes-Castelló, Inmaculada González, Arturo Hernández-Gonzalez, Cristina Fernández, Jaume Campistol, Carina Delpiccolo, Nuria Cortés, Angel Messeguer, Paz Briones, Antonia Ribes. Study of patients and carriers with 2-methyl-3-hydroxybutyryl-CoA dehydrogenase (MHBD) deficiency: difficulties in the diagnosis. Clinical biochemistry. 2009 Jan; 42(1-2):27-33. doi: 10.1016/j.clinbiochem.2008.10.006. [PMID: 18996107]
  • Chang Shi, Chun-Qi Wu, An-Min Cao, He-Zhang Sheng, Xian-Zhong Yan, Ming-Yang Liao. NMR-spectroscopy-based metabonomic approach to the analysis of Bay41-4109, a novel anti-HBV compound, induced hepatotoxicity in rats. Toxicology letters. 2007 Sep; 173(3):161-7. doi: 10.1016/j.toxlet.2007.07.010. [PMID: 17826925]
  • Gregory Kaler, David M Truong, Akash Khandelwal, Megha Nagle, Satish A Eraly, Peter W Swaan, Sanjay K Nigam. Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. The Journal of biological chemistry. 2007 Aug; 282(33):23841-53. doi: 10.1074/jbc.m703467200. [PMID: 17553798]
  • Hye-Ran Yoon. Two step derivatization for the analyses of organic, amino acids and glycines on filter paper plasma by GC-MS/SIM. Archives of pharmacal research. 2007 Mar; 30(3):387-95. doi: 10.1007/bf02977623. [PMID: 17424948]
  • Till Beuerle, Claudine Theuring, Nico Klewer, Stefan Schulz, Thomas Hartmann. Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids. Insect biochemistry and molecular biology. 2007 Jan; 37(1):80-9. doi: 10.1016/j.ibmb.2006.10.005. [PMID: 17175448]
  • Anton Pohanka, Audrius Menkis, Jolanta Levenfors, Anders Broberg. Low-abundance kutznerides from Kutzneria sp. 744. Journal of natural products. 2006 Dec; 69(12):1776-81. doi: 10.1021/np0604331. [PMID: 17190458]
  • Vilson de Castro Vasques, Fabrício Brinco, Moacir Wajner. Intrahippocampal administration of the branched-chain alpha-hydroxy acids accumulating in maple syrup urine disease compromises rat performance in aversive and non-aversive behavioral tasks. Journal of the neurological sciences. 2005 May; 232(1-2):11-21. doi: 10.1016/j.jns.2004.12.015. [PMID: 15850577]
  • Jörn Oliver Sass, Rosemarie Forstner, Wolfgang Sperl. 2-Methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency: impaired catabolism of isoleucine presenting as neurodegenerative disease. Brain & development. 2004 Jan; 26(1):12-4. doi: 10.1016/s0387-7604(03)00071-8. [PMID: 14729408]
  • T Fukao, G X Zhang, N Sakura, T Kubo, H Yamaga, A Hazama, Y Kohno, N Matsuo, M Kondo, S Yamaguchi, Y Shigematsu, N Kondo. The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. Journal of inherited metabolic disease. 2003; 26(5):423-31. doi: 10.1023/a:1025117226051. [PMID: 14518824]
  • V R Sutton, W E O'Brien, G D Clark, J Kim, R J A Wanders. 3-Hydroxy-2-methylbutyryl-CoA dehydrogenase deficiency. Journal of inherited metabolic disease. 2003; 26(1):69-71. doi: 10.1023/a:1024083715568. [PMID: 12872843]
  • S H Korman, H Mandel, A Gutman. Characteristic urine organic acid profile in peroxisomal biogenesis disorders. Journal of inherited metabolic disease. 2000 Jun; 23(4):425-8. doi: 10.1023/a:1005624523611. [PMID: 10896310]
  • K R Kim, J Lee, D Ha, J Jeon, H G Park, J H Kim. Enantiomeric separation and discrimination of 2-hydroxy acids as O-trifluoroacetylated (S)-(+)-3-methyl-2-butyl esters by achiral dual-capillary column gas chromatography. Journal of chromatography. A. 2000 Mar; 874(1):91-100. doi: 10.1016/s0021-9673(00)00072-8. [PMID: 10768503]
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  • T Nakanishi, A Shimizu. Identification of 3-hydroxyisovalerylcarnitine in the urine of a patient with multiple carboxylase deficiency. Annals of clinical biochemistry. 1993 May; 30 ( Pt 3)(?):318-20. doi: 10.1177/000456329303000315. [PMID: 8517616]
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  • S Aramaki, D Lehotay, L Sweetman, W L Nyhan, S C Winter, B Middleton. Urinary excretion of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. Journal of inherited metabolic disease. 1991; 14(1):63-74. doi: 10.1007/bf01804391. [PMID: 1861461]
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