Methylphosphonate (BioDeep_00001030994)
代谢物信息卡片
Methylphosphonate
化学式: CH3O3P-2 (93.9819818)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CP(=O)([O-])[O-]
InChI: InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)/p-2
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)
0 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
- Marion Kanwischer, Thomas Klintzsch, Oliver Schmale. Stable Isotope Approach to Assess the Production and Consumption of Methylphosphonate and Its Contribution to Oxic Methane Formation in Surface Waters.
Environmental science & technology.
2023 10; 57(42):15904-15913. doi:
10.1021/acs.est.3c04098. [PMID: 37842867] - Liang Zhao, Li-Zhou Lin, Ying Zeng, Wen-Kai Teng, Meng-Yun Chen, Jerry J Brand, Ling-Ling Zheng, Nan-Qin Gan, Yong-Hui Gong, Xin-Yi Li, Jin Lv, Ting Chen, Bo-Ping Han, Li-Rong Song, Wen-Sheng Shu. The facilitating role of phycospheric heterotrophic bacteria in cyanobacterial phosphonate availability and Microcystis bloom maintenance.
Microbiome.
2023 06; 11(1):142. doi:
10.1186/s40168-023-01582-2. [PMID: 37365664] - Liang Zhao, Li-Zhou Lin, Meng-Yun Chen, Wen-Kai Teng, Ling-Ling Zheng, Liang Peng, Jin Lv, Jerry J Brand, Chun-Xiang Hu, Bo-Ping Han, Li-Rong Song, Wen-Sheng Shu. The widespread capability of methylphosphonate utilization in filamentous cyanobacteria and its ecological significance.
Water research.
2022 Jun; 217(?):118385. doi:
10.1016/j.watres.2022.118385. [PMID: 35405550] - Merav Blanca, Avital Shifrovitch, Shlomit Dachir, Shlomi Lazar, Maor Elgarisi, Dana Marder, Tamar Shamai Yamin, Shlomi Baranes, Meir Avraham, Hani Dekel Jaoui, Shai Dagan, Avi Weissberg. Highly sensitive retrospective determination of organophosphorous nerve agent biomarkers in human urine implemented in vivo in rabbit.
Archives of toxicology.
2020 09; 94(9):3033-3044. doi:
10.1007/s00204-020-02827-x. [PMID: 32627075] - Boris Sarvin, Markus Himmelsbach, Timur Baygildiev, Oleg Shpigun, Igor Rodin, Andrey Stavrianidi, Wolfgang Buchberger. Nerve agent markers screening after accumulation in garden cress (Lepidium sativum) used as a model plant object.
Journal of chromatography. A.
2019 Jul; 1597(?):214-219. doi:
10.1016/j.chroma.2019.04.025. [PMID: 31010635] - Mai Otsuka, Koichiro Tsuge, Yasuo Seto, Hajime Miyaguchi, Masanobu Uchiyama. Analysis of degradation products of nerve agents via post-pentafluorobenzylation liquid chromatography-tandem mass spectrometry.
Journal of chromatography. A.
2018 Nov; 1577(?):31-37. doi:
10.1016/j.chroma.2018.09.042. [PMID: 30274693] - Chao Xu, Yuan Zhou, Ruilin Qi, Guoqiang Dai, Xiaosong Tan, Hongwu He. Synthesis and herbicidal activity of optically active α-(substituted phenoxyacetoxy) (substituted phenyl) methylphosphonates.
Pesticide biochemistry and physiology.
2017 Nov; 143(?):298-305. doi:
10.1016/j.pestbp.2016.11.009. [PMID: 29183605] - Timur Baygildiev, Alexandra Zatirakha, Igor Rodin, Arkady Braun, Andrey Stavrianidi, Nadezhda Koryagina, Igor Rybalchenko, Oleg Shpigun. Rapid IC-MS/MS determination of methylphosphonic acid in urine of rats exposed to organophosphorus nerve agents.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jul; 1058(?):32-39. doi:
10.1016/j.jchromb.2017.05.005. [PMID: 28531843] - Yasuo Seto, Masumi Tachikawa, Mieko Kanamori-Kataoka, Kikuo Sasamoto, Nobuo Ochiai. Target analysis of tert-butyldimethylsilyl derivatives of nerve agent hydrolysis products by selectable one-dimensional or two-dimensional gas chromatography-mass spectrometry.
Journal of chromatography. A.
2017 Jun; 1501(?):99-106. doi:
10.1016/j.chroma.2017.04.024. [PMID: 28434709] - Chih-Kai Chao, S Kaleem Ahmed, John M Gerdes, Charles M Thompson. Novel Organophosphate Ligand O-(2-Fluoroethyl)-O-(p-Nitrophenyl)Methylphosphonate: Synthesis, Hydrolytic Stability and Analysis of the Inhibition and Reactivation of Cholinesterases.
Chemical research in toxicology.
2016 11; 29(11):1810-1817. doi:
10.1021/acs.chemrestox.6b00160. [PMID: 27551891] - Chang-Cai Liu, Gui-Lan Huang, Hai-Ling Xi, Shi-Lei Liu, Jing-Quan Liu, Hui-Lan Yu, Shi-Kun Zhou, Long-Hui Liang, Ling Yuan. Simultaneous quantification of soman and VX adducts to butyrylcholinesterase, their aged methylphosphonic acid adduct and butyrylcholinesterase in plasma using an off-column procainamide-gel separation method combined with UHPLC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2016 Nov; 1036-1037(?):57-65. doi:
10.1016/j.jchromb.2016.09.044. [PMID: 27718463] - T M Baygildiev, I A Rodin, A N Stavrianidi, A V Braun, A T Lebedev, I V Rybalchenko, O A Shpigun. Hydrophilic interaction liquid chromatography-tandem mass spectrometry methylphosponic and alkyl methylphosphonic acids determination in environmental samples after pre-column derivatization with p-bromophenacyl bromide.
Journal of chromatography. A.
2016 Apr; 1442(?):19-25. doi:
10.1016/j.chroma.2016.03.001. [PMID: 26965649] - Tsang-Pai Liu, Si-Han Wu, Yi-Ping Chen, Chih-Ming Chou, Chien-Tsu Chen. Biosafety evaluations of well-dispersed mesoporous silica nanoparticles: towards in vivo-relevant conditions.
Nanoscale.
2015 Apr; 7(15):6471-80. doi:
10.1039/c4nr07421a. [PMID: 25804371] - Melissa D Carter, Brian S Crow, Brooke G Pantazides, Caroline M Watson, Jerry D Thomas, Thomas A Blake, Rudolph C Johnson. Direct quantitation of methyl phosphonate adducts to human serum butyrylcholinesterase by immunomagnetic-UHPLC-MS/MS.
Analytical chemistry.
2013 Nov; 85(22):11106-11. doi:
10.1021/ac4029714. [PMID: 24205842] - Laura-Anne Brown, Tony R Larson, Ian A Graham, Chris Hawes, Rupesh Paudyal, Stuart L Warriner, Alison Baker. An inhibitor of oil body mobilization in Arabidopsis.
The New phytologist.
2013 Nov; 200(3):641-649. doi:
10.1111/nph.12467. [PMID: 24033128] - Renuka Gupte, Renukadevi Patil, Jianxiong Liu, Yaohong Wang, Sue C Lee, Yuko Fujiwara, James Fells, Alyssa L Bolen, Karin Emmons-Thompson, C Ryan Yates, Anjaih Siddam, Nattapon Panupinthu, Truc-Chi T Pham, Daniel L Baker, Abby L Parrill, Gordon B Mills, Gabor Tigyi, Duane D Miller. Benzyl and naphthalene methylphosphonic acid inhibitors of autotaxin with anti-invasive and anti-metastatic activity.
ChemMedChem.
2011 May; 6(5):922-35. doi:
10.1002/cmdc.201000425. [PMID: 21465666] - James Pratt, Anne-Marie Boisson, Elisabeth Gout, Richard Bligny, Roland Douce, Serge Aubert. Phosphate (Pi) starvation effect on the cytosolic Pi concentration and Pi exchanges across the tonoplast in plant cells: an in vivo 31P-nuclear magnetic resonance study using methylphosphonate as a Pi analog.
Plant physiology.
2009 Nov; 151(3):1646-57. doi:
10.1104/pp.109.144626. [PMID: 19755536] - D L Couldwell, R Dunford, N J Kruger, D C Lloyd, R G Ratcliffe, A M O Smith. Response of cytoplasmic pH to anoxia in plant tissues with altered activities of fermentation enzymes: application of methyl phosphonate as an NMR pH probe.
Annals of botany.
2009 Jan; 103(2):249-58. doi:
10.1093/aob/mcn174. [PMID: 18824473] - Melissa M Adams, María R Gómez-García, Arthur R Grossman, Devaki Bhaya. Phosphorus deprivation responses and phosphonate utilization in a thermophilic Synechococcus sp. from microbial mats.
Journal of bacteriology.
2008 Dec; 190(24):8171-84. doi:
10.1128/jb.01011-08. [PMID: 18931115] - Douglas D Richardson, Joseph A Caruso. Derivatization of organophosphorus nerve agent degradation products for gas chromatography with ICPMS and TOF-MS detection.
Analytical and bioanalytical chemistry.
2007 Jun; 388(4):809-23. doi:
10.1007/s00216-007-1164-8. [PMID: 17356819] - Fernanda Marques, Lurdes Gano, M Paula Campello, Sara Lacerda, Isabel Santos, Luís M P Lima, Judite Costa, Patrícia Antunes, Rita Delgado. 13- and 14-membered macrocyclic ligands containing methylcarboxylate or methylphosphonate pendant arms: chemical and biological evaluation of their (153)Sm and (166)Ho complexes as potential agents for therapy or bone pain palliation.
Journal of inorganic biochemistry.
2006 Feb; 100(2):270-80. doi:
10.1016/j.jinorgbio.2005.11.011. [PMID: 16387365] - Jean-Marie Mouillon, Bengt L Persson. Inhibition of the protein kinase A alters the degradation of the high-affinity phosphate transporter Pho84 in Saccharomyces cerevisiae.
Current genetics.
2005 Oct; 48(4):226-34. doi:
10.1007/s00294-005-0019-0. [PMID: 16160831] - James R Pratt, Jean-Marie Mouillon, Jens O Lagerstedt, Johanna Pattison-Granberg, Kent I Lundh, Bengt L Persson. Effects of methylphosphonate, a phosphate analogue, on the expression and degradation of the high-affinity phosphate transporter Pho84, in Saccharomyces cerevisiae.
Biochemistry.
2004 Nov; 43(45):14444-53. doi:
10.1021/bi049327t. [PMID: 15533049] - Fernanda Marques, Krassimira P Guerra, Lurdes Gano, Judite Costa, M Paula Campello, Luís M P Lima, Rita Delgado, Isabel Santos. 153Sm and 166Ho complexes with tetraaza macrocycles containing pyridine and methylcarboxylate or methylphosphonate pendant arms.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry.
2004 Oct; 9(7):859-72. doi:
10.1007/s00775-004-0587-3. [PMID: 15338314] - Chrissy E Prater, Paul S Miller. 3'-methylphosphonate-modified oligo-2'-O-methylribonucleotides and their Tat peptide conjugates: uptake and stability in mouse fibroblasts in culture.
Bioconjugate chemistry.
2004 May; 15(3):498-507. doi:
10.1021/bc049977+. [PMID: 15149177] - Mieko Kataoka, Yasuo Seto. Discriminative determination of alkyl methylphosphonates and methylphosphonate in blood plasma and urine by gas chromatography-mass spectrometry after tert.-butyldimethylsilylation.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 Sep; 795(1):123-32. doi:
10.1016/s1570-0232(03)00548-8. [PMID: 12957176] - Tomoko Hamma, Paul S Miller. Interactions of hairpin oligo-2'-O-methylribonucleotides containing methylphosphonate linkages with HIV TAR RNA.
Antisense & nucleic acid drug development.
2003 Feb; 13(1):19-30. doi:
10.1089/108729003764097313. [PMID: 12691533] - D M Hui, M Minami. Monitoring of fluorine in urine samples of patients involved in the tokyo sarin disaster, in connection with the detection of other decomposition products of sarin and the by-products generated during sarin synthesis.
Clinica chimica acta; international journal of clinical chemistry.
2000 Dec; 302(1-2):171-88. doi:
10.1016/s0009-8981(00)00364-8. [PMID: 11074074] - P S Miller, R A Cassidy, T Hamma, N S Kondo. Studies on anti-human immunodeficiency virus oligonucleotides that have alternating methylphosphonate/phosphodiester linkages.
Pharmacology & therapeutics.
2000 Mar; 85(3):159-63. doi:
10.1016/s0163-7258(99)00054-6. [PMID: 10739870] - T Hamma, P S Miller. Syntheses of alternating oligo-2'-O-methylribonucleoside methylphosphonates and their interactions with HIV TAR RNA.
Biochemistry.
1999 Nov; 38(46):15333-42. doi:
10.1021/bi991962p. [PMID: 10563819] - P S Miller, S A Kipp, C McGill. A psoralen-conjugated triplex-forming oligodeoxyribonucleotide containing alternating methylphosphonate-phosphodiester linkages: synthesis and interactions with DNA.
Bioconjugate chemistry.
1999 Jul; 10(4):572-7. doi:
10.1021/bc980140m. [PMID: 10411453] - T Nakajima, K Sasaki, H Ozawa, Y Sekjima, H Morita, Y Fukushima, N Yanagisawa. Urinary metabolites of sarin in a patient of the Matsumoto sarin incident.
Archives of toxicology.
1998 Sep; 72(9):601-3. doi:
10.1007/s002040050549. [PMID: 9806433] - M Katagi, M Nishikawa, M Tatsuno, H Tsuchihashi. Determination of the main hydrolysis products of organophosphorus nerve agents, methylphosphonic acids, in human serum by indirect photometric detection ion chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Sep; 698(1-2):81-8. doi:
10.1016/s0378-4347(97)00284-3. [PMID: 9367195] - M Minami, D M Hui, M Katsumata, H Inagaki, C A Boulet. Method for the analysis of the methylphosphonic acid metabolites of sarin and its ethanol-substituted analogue in urine as applied to the victims of the Tokyo sarin disaster.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Aug; 695(2):237-44. doi:
10.1016/s0378-4347(97)00203-x. [PMID: 9300859] - M Katagi, M Nishikawa, M Tatsuno, H Tsuchihashi. Determination of the main hydrolysis product of O-ethyl S-2-diisopropylaminoethyl methylphosphonothiolate, ethyl methylphosphonic acid, in human serum.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Feb; 689(2):327-33. doi:
10.1016/s0378-4347(96)00356-8. [PMID: 9080318] - S Agrawal, R Zhang. Pharmacokinetics of oligonucleotides.
Ciba Foundation symposium.
1997; 209(?):60-75; discussion 75. doi:
10.1002/9780470515396.ch6. [PMID: 9383569] - O Zhao, I M Kovach. Reversible modification of tissue-type plasminogen activator by methylphosphonate esters.
Bioorganic & medicinal chemistry.
1996 Apr; 4(4):523-9. doi:
10.1016/0968-0896(96)84792-4. [PMID: 8735839] - S Agrawal, J Temsamani, W Galbraith, J Tang. Pharmacokinetics of antisense oligonucleotides.
Clinical pharmacokinetics.
1995 Jan; 28(1):7-16. doi:
10.2165/00003088-199528010-00002. [PMID: 7712663] - J Thaden, P S Miller. Photoaffinity behavior of a conjugate of oligonucleoside methylphosphonate, rhodamine, and psoralen in the presence of complementary oligonucleotides.
Bioconjugate chemistry.
1993 Sep; 4(5):386-94. doi:
10.1021/bc00023a014. [PMID: 7506058] - E Wickstrom, T A Bacon, E L Wickstrom. Down-regulation of c-MYC antigen expression in lymphocytes of Emu-c-myc transgenic mice treated with anti-c-myc DNA methylphosphonates.
Cancer research.
1992 Dec; 52(24):6741-5. doi:
NULL. [PMID: 1458461] - S Akhtar, S Basu, E Wickstrom, R L Juliano. Interactions of antisense DNA oligonucleotide analogs with phospholipid membranes (liposomes).
Nucleic acids research.
1991 Oct; 19(20):5551-9. doi:
10.1093/nar/19.20.5551. [PMID: 1945832] - D M Tidd, H M Warenius. Partial protection of oncogene, anti-sense oligodeoxynucleotides against serum nuclease degradation using terminal methylphosphonate groups.
British journal of cancer.
1989 Sep; 60(3):343-50. doi:
10.1038/bjc.1989.283. [PMID: 2551358] - N R Shine, J A Xuan, A P Koretsky, M W Weiner. Determination of renal molar concentrations of phosphorus-containing metabolites in vivo using 31P NMR.
Magnetic resonance in medicine.
1987 Mar; 4(3):244-51. doi:
10.1002/mrm.1910040305. [PMID: 3574058]