Methylselenic acid (BioDeep_00000012471)
Secondary id: BioDeep_00001868769
human metabolite
代谢物信息卡片
Methaneseleninic acid
化学式: CH4O2Se (127.9376494)
中文名称: 甲亚硒酸
谱图信息:
最多检出来源 Homo sapiens(blood) 40%
分子结构信息
SMILES: C[Se](=O)O
InChI: InChI=1S/CH4O2Se/c1-4(2)3/h1H3,(H,2,3)
描述信息
This compound belongs to the family of Seleninic Acids and Derivatives. These are compounds containing a seleninic acid moiety, with the general structure Rse(=O)OH
同义名列表
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:77012
- KEGG: C18902
- PubChem: 161597
- HMDB: HMDB0060489
- Metlin: METLIN72663
- ChEMBL: CHEMBL399906
- Wikipedia: Methaneseleninic_Acid
- CAS: 28274-57-9
- PMhub: MS000026790
- PubChem: 124489574
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
39 个相关的代谢反应过程信息。
Reactome(39)
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
H2O + SeMet ⟶ 2OBUTA + MeSeH + ammonia - Formation of selenosugars for excretion:
MeSebGalNac ⟶ 2-acetamidoglucal + MeSeO2H - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
ATP + H2O + H2Se ⟶ AMP + H+ + Pi + SELP - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
Sec ⟶ H2Se + L-Ala - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
Sec ⟶ H2Se + L-Ala - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
Sec ⟶ H2Se + L-Ala - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
Sec ⟶ H2Se + L-Ala - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
Sec ⟶ H2Se + L-Ala - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN - Metabolism of ingested MeSeO2H into MeSeH:
H+ + MeSeO2H + TPNH ⟶ H2O + MeSeOH + TPN
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Valentina N Mal'tseva, Michael V Goltyaev, Egor A Turovsky, Elena G Varlamova. Immunomodulatory and Anti-Inflammatory Properties of Selenium-Containing Agents: Their Role in the Regulation of Defense Mechanisms against COVID-19.
International journal of molecular sciences.
2022 Feb; 23(4):. doi:
10.3390/ijms23042360. [PMID: 35216476] - Rania A Gawish, Hanan A Fahmy, Abeer I Abd El Fattah, Ahmed S Nada. The potential effect of methylseleninic acid (MSA) against γ-irradiation induced testicular damage in rats: Impact on JAK/STAT pathway.
Archives of biochemistry and biophysics.
2020 01; 679(?):108205. doi:
10.1016/j.abb.2019.108205. [PMID: 31758927] - John T Lafin, Ehab H Sarsour, Amanda L Kalen, Brett A Wagner, Garry R Buettner, Prabhat C Goswami. Methylseleninic Acid Induces Lipid Peroxidation and Radiation Sensitivity in Head and Neck Cancer Cells.
International journal of molecular sciences.
2019 Jan; 20(1):. doi:
10.3390/ijms20010225. [PMID: 30626124] - Sneha Sundaram, Lin Yan. Dietary Supplementation with Methylseleninic Acid Inhibits Mammary Tumorigenesis and Metastasis in Male MMTV-PyMT Mice.
Biological trace element research.
2018 Jul; 184(1):186-195. doi:
10.1007/s12011-017-1188-7. [PMID: 29032404] - Xiaotong Lu, Enxiang Zhang, Shutao Yin, Lihong Fan, Hongbo Hu. Methylseleninic Acid Prevents Patulin-Induced Hepatotoxicity and Nephrotoxicity via the Inhibition of Oxidative Stress and Inactivation of p53 and MAPKs.
Journal of agricultural and food chemistry.
2017 Jul; 65(26):5299-5305. doi:
10.1021/acs.jafc.7b01338. [PMID: 28594550] - Huawei Zeng, Min Wu. The Inhibitory Efficacy of Methylseleninic Acid Against Colon Cancer Xenografts in C57BL/6 Mice.
Nutrition and cancer.
2015; 67(5):831-8. doi:
10.1080/01635581.2015.1042547. [PMID: 26011019] - Naveen Kaushal, Avinash K Kudva, Andrew D Patterson, Christopher Chiaro, Mary J Kennett, Dhimant Desai, Shantu Amin, Bradley A Carlson, Margherita T Cantorna, K Sandeep Prabhu. Crucial role of macrophage selenoproteins in experimental colitis.
Journal of immunology (Baltimore, Md. : 1950).
2014 Oct; 193(7):3683-92. doi:
10.4049/jimmunol.1400347. [PMID: 25187657] - Lin Yan, Gerald F Combs. Consumption of a high-fat diet abrogates inhibitory effects of methylseleninic acid on spontaneous metastasis of Lewis lung carcinoma in mice.
Carcinogenesis.
2014 Oct; 35(10):2308-13. doi:
10.1093/carcin/bgu153. [PMID: 25053624] - Chandra K Singh, Mary A Ndiaye, Imtiaz A Siddiqui, Minakshi Nihal, Thomas Havighurst, KyungMann Kim, Weixiong Zhong, Hasan Mukhtar, Nihal Ahmad. Methaneseleninic acid and γ-Tocopherol combination inhibits prostate tumor growth in Vivo in a xenograft mouse model.
Oncotarget.
2014 Jun; 5(11):3651-61. doi:
10.18632/oncotarget.1979. [PMID: 25004451] - Yu-Chi Chen, K Sandeep Prabhu, Arunangshu Das, Andrea M Mastro. Dietary selenium supplementation modifies breast tumor growth and metastasis.
International journal of cancer.
2013 Nov; 133(9):2054-64. doi:
10.1002/ijc.28224. [PMID: 23613334] - Lv-Hui Sun, Jun-Gang Li, Hua Zhao, Jing Shi, Jia-Qiang Huang, Kang-Ning Wang, Xin-Jie Xia, Li Li, Xin Gen Lei. Porcine serum can be biofortified with selenium to inhibit proliferation of three types of human cancer cells.
The Journal of nutrition.
2013 Jul; 143(7):1115-22. doi:
10.3945/jn.113.177410. [PMID: 23677865] - Lin Yan, Lana C DeMars. Dietary supplementation with methylseleninic acid, but not selenomethionine, reduces spontaneous metastasis of Lewis lung carcinoma in mice.
International journal of cancer.
2012 Sep; 131(6):1260-6. doi:
10.1002/ijc.27355. [PMID: 22095442] - Sreenivasulu Chintala, Tanbir Najrana, Karoly Toth, Shousong Cao, Farukh A Durrani, Roberto Pili, Youcef M Rustum. Prolyl hydroxylase 2 dependent and Von-Hippel-Lindau independent degradation of Hypoxia-inducible factor 1 and 2 alpha by selenium in clear cell renal cell carcinoma leads to tumor growth inhibition.
BMC cancer.
2012 Jul; 12(?):293. doi:
10.1186/1471-2407-12-293. [PMID: 22804960] - Carolin S Hoefig, Kostja Renko, Josef Köhrle, Marc Birringer, Lutz Schomburg. Comparison of different selenocompounds with respect to nutritional value vs. toxicity using liver cells in culture.
The Journal of nutritional biochemistry.
2011 Oct; 22(10):945-55. doi:
10.1016/j.jnutbio.2010.08.006. [PMID: 21190829] - Shuang Liu, Yanfeng Qi, Yubin Ge, Tamika Duplessis, Brian G Rowan, Clement Ip, Helen Cheng, Paul S Rennie, Izumi Horikawa, Arthur J Lustig, Qun Yu, Haitao Zhang, Yan Dong. Telomerase as an important target of androgen signaling blockade for prostate cancer treatment.
Molecular cancer therapeutics.
2010 Jul; 9(7):2016-25. doi:
10.1158/1535-7163.mct-09-0924. [PMID: 20571066] - Matthew Honeggar, Robert Beck, Philip J Moos. Thioredoxin reductase 1 ablation sensitizes colon cancer cells to methylseleninate-mediated cytotoxicity.
Toxicology and applied pharmacology.
2009 Dec; 241(3):348-55. doi:
10.1016/j.taap.2009.09.010. [PMID: 19782697] - Usha Gundimeda, Jason Eric Schiffman, Simcha Neeli Gottlieb, Brandon Ian Roth, Rayudu Gopalakrishna. Negation of the cancer-preventive actions of selenium by over-expression of protein kinase Cepsilon and selenoprotein thioredoxin reductase.
Carcinogenesis.
2009 Sep; 30(9):1553-61. doi:
10.1093/carcin/bgp164. [PMID: 19578042] - Usha Gundimeda, Jason Eric Schiffman, Divya Chhabra, Jourdan Wong, Adela Wu, Rayudu Gopalakrishna. Locally generated methylseleninic acid induces specific inactivation of protein kinase C isoenzymes: relevance to selenium-induced apoptosis in prostate cancer cells.
The Journal of biological chemistry.
2008 Dec; 283(50):34519-31. doi:
10.1074/jbc.m807007200. [PMID: 18922790] - Kazuo T Suzuki, Yoshiro Tsuji, Yuki Ohta, Noriyuki Suzuki. Preferential organ distribution of methylselenol source Se-methylselenocysteine relative to methylseleninic acid.
Toxicology and applied pharmacology.
2008 Feb; 227(1):76-83. doi:
10.1016/j.taap.2007.10.001. [PMID: 18035386] - Kazuo T Suzuki, Yuki Ohta, Noriyuki Suzuki. Availability and metabolism of 77Se-methylseleninic acid compared simultaneously with those of three related selenocompounds.
Toxicology and applied pharmacology.
2006 Nov; 217(1):51-62. doi:
10.1016/j.taap.2006.07.005. [PMID: 16962623] - Kazuo T Suzuki, Kazuki Kurasaki, Sayaka Ogawa, Noriyuki Suzuki. Metabolic transformation of methylseleninic acid through key selenium intermediate selenide.
Toxicology and applied pharmacology.
2006 Sep; 215(2):189-97. doi:
10.1016/j.taap.2006.02.011. [PMID: 16600319] - K Last, L Maharaj, J Perry, S Strauss, J Fitzgibbon, T A Lister, S Joel. The activity of methylated and non-methylated selenium species in lymphoma cell lines and primary tumours.
Annals of oncology : official journal of the European Society for Medical Oncology.
2006 May; 17(5):773-9. doi:
10.1093/annonc/mdl004. [PMID: 16469755] - Rizky Abdulah, Kaori Miyazaki, Minato Nakazawa, Hiroshi Koyama. Chemical forms of selenium for cancer prevention.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS).
2005; 19(2-3):141-50. doi:
10.1016/j.jtemb.2005.09.003. [PMID: 16325529] - Z Wang, C Jiang, H Ganther, J Lü. Antimitogenic and proapoptotic activities of methylseleninic acid in vascular endothelial cells and associated effects on PI3K-AKT, ERK, JNK and p38 MAPK signaling.
Cancer research.
2001 Oct; 61(19):7171-8. doi:
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