RHODANINE (BioDeep_00001868540)
Main id: BioDeep_00000006454
代谢物信息卡片
RHODANINE
化学式: C3H3NOS2 (132.9656)
中文名称: 罗丹宁
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1C(=O)NC(=S)S1
InChI: InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:8830
- KEGG: C07280
- PubChem: 1201546
- ChEMBL: CHEMBL224633
- MeSH: Rhodanine
- CAS: 162382-53-8
- CAS: 950981-11-0
- CAS: 162382-52-7
- CAS: 141-84-4
- PubChem: 9489
- PDB-CCD: E60
- NIKKAJI: J5.808D
- RefMet: Rhodanine
- KNApSAcK: 8830
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)
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
- Rozh Q Ameen, Zahra A Amin, Hiwa O Ahmad, Diler D Ghafur, Melodya G Toma, Nyan Sabah, Muhammad Fakhir, Gardoon Abdulla. Gastroprotective effect of rhodanine and 2,4-thiazolidinediones scaffolds in rat stomachs by contribution of anti-apoptotic (BCL-2) and tumor suppressor (P53) proteins.
Scientific reports.
2024 01; 14(1):1699. doi:
10.1038/s41598-024-51446-4. [PMID: 38242960] - Sakthiprabha Sampath, Sangilimuthu Alagar Yadav, Manjunath Meti, Sundaram Kaveri, Ravi Subban, Rajagopal Subramanyam. Elucidation of binding mechanism of rhodanine derivative P4OC on bovine serum albumin.
Journal of biomolecular structure & dynamics.
2024 Jan; 42(1):475-482. doi:
10.1080/07391102.2023.2194001. [PMID: 36974960] - Qing Han, Nan Wu, Jingyu Zhang, Tianyu Feng, Yunjiang Zi, Rulei Zhang, Renxuan Zou, Yaoyang Liu, Qing Yang, Hongxia Duan. Discovery of Rhodanine Inhibitors Targeting Of ChtI Based on the π-Stacking Effect and Aqueous Solubility.
Journal of agricultural and food chemistry.
2023 Dec; 71(48):18685-18695. doi:
10.1021/acs.jafc.3c05287. [PMID: 38006338] - Qing Han, Nan Wu, Yao-Yang Liu, Jing-Yu Zhang, Ru-Lei Zhang, Hui-Lin Li, Zhi-Yang Jiang, Jia-Xing Huang, Hong-Xia Duan, Qing Yang. Piperonyl-Tethered Rhodanine Derivatives Potently Inhibit Chitinolytic Enzymes of Ostrinia furnacalis.
Journal of agricultural and food chemistry.
2022 Jun; 70(24):7387-7399. doi:
10.1021/acs.jafc.2c02091. [PMID: 35687728] - Jing Pu, Xiaoyang He, Wei Xu, Cong Wang, Qiaoshuai Lan, Chen Hua, Kai Wang, Lu Lu, Shibo Jiang. The Analogs of Furanyl Methylidene Rhodanine Exhibit Broad-Spectrum Inhibitory and Inactivating Activities against Enveloped Viruses, including SARS-CoV-2 and Its Variants.
Viruses.
2022 02; 14(3):. doi:
10.3390/v14030489. [PMID: 35336896] - Julianne N Richard, Jennifer E Graham, Sharon A Center, Michael M Garner, Drury R Reavill. Hepatic copper accumulates in ferrets with and without hepatobiliary disease.
American journal of veterinary research.
2022 Jan; 83(4):371-380. doi:
10.2460/ajvr.21.08.0131. [PMID: 35092668] - Anna N Ligezka, Silvia Radenkovic, Mayank Saraswat, Kishore Garapati, Wasantha Ranatunga, Wirginia Krzysciak, Hitoshi Yanaihara, Graeme Preston, William Brucker, Renee M McGovern, Joel M Reid, David Cassiman, Karthik Muthusamy, Christin Johnsen, Saadet Mercimek-Andrews, Austin Larson, Christina Lam, Andrew C Edmondson, Bart Ghesquière, Peter Witters, Kimiyo Raymond, Devin Oglesbee, Akhilesh Pandey, Ethan O Perlstein, Tamas Kozicz, Eva Morava. Sorbitol Is a Severity Biomarker for PMM2-CDG with Therapeutic Implications.
Annals of neurology.
2021 12; 90(6):887-900. doi:
10.1002/ana.26245. [PMID: 34652821] - Sivakumar Lingappa, Muthugounder Subramanian Shivakumar, Thamilarasan Manivasagam, Somasundaram Thirugnanasambandan Somasundaram, Palaniappan Seedevi. Neuroprotective Effect of Epalrestat on Hydrogen Peroxide-Induced Neurodegeneration in SH-SY5Y Cellular Model.
Journal of microbiology and biotechnology.
2021 Jun; 31(6):867-874. doi:
10.4014/jmb.2101.01002. [PMID: 33820886] - Zubeyir Elmazoglu, Marta Soltesova Prnova, Milan Stefek, Asli F Ceylan, Michael Aschner, Edgar Rangel-López, Abel Santamaria, Cimen Karasu. Protective Effects of Novel Substituted Triazinoindole Inhibitors of Aldose Reductase and Epalrestat in Neuron-like PC12 Cells and BV2 Rodent Microglial Cells Exposed to Toxic Models of Oxidative Stress: Comparison with the Pyridoindole Antioxidant Stobadine.
Neurotoxicity research.
2021 Jun; 39(3):588-597. doi:
10.1007/s12640-021-00349-7. [PMID: 33713301] - Shalki Choudhary, Manoj Kumar, Om Silakari. QM/MM analysis, synthesis and biological evaluation of epalrestat based mutual-prodrugs for diabetic neuropathy and nephropathy.
Bioorganic chemistry.
2021 03; 108(?):104556. doi:
10.1016/j.bioorg.2020.104556. [PMID: 33376013] - Adam J Miller, Sharon A Center, John F Randolph, Cameron H Friesen, Andrew D Miller, Karen W Warner. Disparities in hepatic copper concentrations determined by atomic absorption spectroscopy, inductively coupled plasma mass spectrometry, and digital image analysis of rhodanine-stained sections in dogs.
Journal of the American Veterinary Medical Association.
2021 Feb; 258(4):395-406. doi:
10.2460/javma.258.4.395. [PMID: 33539202] - Keisuke Sato, Ryosuke Tatsunami, Koji Wakame. Epalrestat suppresses inflammatory response in lipopolysaccharide-stimulated RAW264.7 cells.
Allergologia et immunopathologia.
2021; 49(5):1-8. doi:
10.15586/aei.v49i5.102. [PMID: 34476915] - Zunaira Alvi, Muhammad Akhtar, Arshad Mahmood, Nisar Ur-Rahman, Imran Nazir, Hadia Sadaquat, Muhammad Ijaz, Shahzada Khurram Syed, Muhammad Khurram Waqas, Yi Wang. Enhanced Oral Bioavailability of Epalrestat SBE7-β-CD Complex Loaded Chitosan Nanoparticles: Preparation, Characterization and in-vivo Pharmacokinetic Evaluation.
International journal of nanomedicine.
2021; 16(?):8353-8373. doi:
10.2147/ijn.s339857. [PMID: 35002232] - Yanni Zhu, Yanjuan Sheng. RETRACTED: Sustained delivery of epalrestat to the retina using PEGylated solid lipid nanoparticles laden contact lens.
International journal of pharmaceutics.
2020 09; 587(?):119688. doi:
10.1016/j.ijpharm.2020.119688. [PMID: 32717281] - Yuki Murakami, Chiaki Murakami, Fumi Hoshino, Qiang Lu, Rino Akiyama, Atsumi Yamaki, Daisuke Takahashi, Fumio Sakane. Palmitic acid- and/or palmitoleic acid-containing phosphatidic acids are generated by diacylglycerol kinase α in starved Jurkat T cells.
Biochemical and biophysical research communications.
2020 05; 525(4):1054-1060. doi:
10.1016/j.bbrc.2020.02.162. [PMID: 32184022] - Ryosuke Tatsunami, Yu Murao, Keisuke Sato. [Protective Effect of Epalrestat against Oxidative Stress-induced Cytotoxicity].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2020; 140(11):1381-1388. doi:
10.1248/yakushi.20-00167. [PMID: 33132274] - Sangeetha Iyer, Feba S Sam, Nina DiPrimio, Graeme Preston, Jan Verheijen, Kausalya Murthy, Zachary Parton, Hillary Tsang, Jessica Lao, Eva Morava, Ethan O Perlstein. Repurposing the aldose reductase inhibitor and diabetic neuropathy drug epalrestat for the congenital disorder of glycosylation PMM2-CDG.
Disease models & mechanisms.
2019 11; 12(11):. doi:
10.1242/dmm.040584. [PMID: 31636082] - Sharon Pindar, Christina Ramirez. Predicting copper toxicosis: relationship between the ATP7A and ATP7B gene mutations and hepatic copper quantification in dogs.
Human genetics.
2019 May; 138(5):541-546. doi:
10.1007/s00439-019-02010-y. [PMID: 31062085] - Bai-Bing Yang, Zhi-Wei Hong, Zheng Zhang, Wen Yu, Tao Song, Lei-Lei Zhu, He-Song Jiang, Guo-Tao Chen, Yun Chen, Yu-Tian Dai. Epalrestat, an Aldose Reductase Inhibitor, Restores Erectile Function in Streptozocin-induced Diabetic Rats.
International journal of impotence research.
2019 Mar; 31(2):97-104. doi:
10.1038/s41443-018-0075-x. [PMID: 30214006] - Yun-Xing Gao, Juan Tang, Qian Zhang, Li-Li Jiang, Xian-Wei Li. [Interventional effect of epalrestat on renal interstitial fibrosis in unilateral ureteral obstruction rats and its mechanism].
Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology.
2019 Jan; 35(1):79-84. doi:
10.12047/j.cjap.5735.2019.019. [PMID: 31245958] - Jun He, Hao-Xue Gao, Na Yang, Xiao-Dong Zhu, Run-Bin Sun, Yuan Xie, Cai-Hong Zeng, Jing-Wei Zhang, Jian-Kun Wang, Fei Ding, Ji-Ye Aa, Guang-Ji Wang. The aldose reductase inhibitor epalrestat exerts nephritic protection on diabetic nephropathy in db/db mice through metabolic modulation.
Acta pharmacologica Sinica.
2019 Jan; 40(1):86-97. doi:
10.1038/s41401-018-0043-5. [PMID: 29930278] - Satoshi Yamaori, Noriyuki Araki, Mio Shionoiri, Kurumi Ikehata, Shinobu Kamijo, Shigeru Ohmori, Kazuhito Watanabe. A Specific Probe Substrate for Evaluation of CYP4A11 Activity in Human Tissue Microsomes and a Highly Selective CYP4A11 Inhibitor: Luciferin-4A and Epalrestat.
The Journal of pharmacology and experimental therapeutics.
2018 09; 366(3):446-457. doi:
10.1124/jpet.118.249557. [PMID: 29976573] - Chenge Li, Aurélien Mourton, Marie-Aude Plamont, Vanessa Rodrigues, Isabelle Aujard, Michel Volovitch, Thomas Le Saux, Franck Perez, Sophie Vriz, Ludovic Jullien, Alain Joliot, Arnaud Gautier. Fluorogenic Probing of Membrane Protein Trafficking.
Bioconjugate chemistry.
2018 06; 29(6):1823-1828. doi:
10.1021/acs.bioconjchem.8b00180. [PMID: 29791141] - Xiaotong Wang, Haixiong Lin, Shuai Xu, Yuanlin Jin, Ren Zhang. The clinical efficacy of epalrestat combined with α-lipoic acid in diabetic peripheral neuropathy: Protocol for a systematic review and meta-analysis.
Medicine.
2018 Feb; 97(6):e9828. doi:
10.1097/md.0000000000009828. [PMID: 29419686] - Valeria Cagno, Cristina Tintori, Andrea Civra, Roberta Cavalli, Marika Tiberi, Lorenzo Botta, Annalaura Brai, Giulio Poli, Caroline Tapparel, David Lembo, Maurizio Botta. Novel broad spectrum virucidal molecules against enveloped viruses.
PloS one.
2018; 13(12):e0208333. doi:
10.1371/journal.pone.0208333. [PMID: 30532192] - Xiaotong Wang, Haixiong Lin, Shuai Xu, Yuanlin Jin, Ren Zhang. Alpha lipoic acid combined with epalrestat: a therapeutic option for patients with diabetic peripheral neuropathy.
Drug design, development and therapy.
2018; 12(?):2827-2840. doi:
10.2147/dddt.s168878. [PMID: 30233145] - Cristina Tintori, Giulia Iovenitti, Elisa Rita Ceresola, Roberto Ferrarese, Claudio Zamperini, Annalaura Brai, Giulio Poli, Elena Dreassi, Valeria Cagno, David Lembo, Filippo Canducci, Maurizio Botta. Rhodanine derivatives as potent anti-HIV and anti-HSV microbicides.
PloS one.
2018; 13(6):e0198478. doi:
10.1371/journal.pone.0198478. [PMID: 29870553] - Oliver Hachmöller, Michaela Aichler, Kristina Schwamborn, Lisa Lutz, Martin Werner, Michael Sperling, Axel Walch, Uwe Karst. Investigating the influence of standard staining procedures on the copper distribution and concentration in Wilson's disease liver samples by laser ablation-inductively coupled plasma-mass spectrometry.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS).
2017 Dec; 44(?):71-75. doi:
10.1016/j.jtemb.2017.06.002. [PMID: 28965603] - Ahmad Nazaktabar, Mohammad Soleimani Lashkenari, Atefeh Araghi, Mohsen Ghorbani, Hannaneh Golshahi. In vivo evaluation of toxicity and antiviral activity of polyrhodanine nanoparticles by using the chicken embryo model.
International journal of biological macromolecules.
2017 Oct; 103(?):379-384. doi:
10.1016/j.ijbiomac.2017.05.069. [PMID: 28526349] - Jingqiu Huang, Runbin Sun, Siqi Feng, Jun He, Fei Fei, Haoxue Gao, Yuqing Zhao, Yue Zhang, Huilin Gu, Jiye Aa, Guangji Wang. Sensitive analysis and pharmacokinetic study of epalrestat in C57BL/6J mice.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jun; 1055-1056(?):98-103. doi:
10.1016/j.jchromb.2017.03.040. [PMID: 28445852] - Hong Sun, Yunhai Bo, Mingjie Zhang, Xiao Wu, Mingyang Zhou, Longshan Zhao, Zhili Xiong. Simultaneous determination of epalrestat and puerarin in rat plasma by UHPLC-MS/MS: Application to their pharmacokinetic interaction study.
Biomedical chromatography : BMC.
2017 Apr; 31(4):. doi:
10.1002/bmc.3855. [PMID: 27650591] - Zhiyong Huang, Quan Hong, Xueguang Zhang, Wenzhen Xiao, Liyuan Wang, Shaoyuan Cui, Zhe Feng, Yang Lv, Guangyan Cai, Xiangmei Chen, Di Wu. Aldose reductase mediates endothelial cell dysfunction induced by high uric acid concentrations.
Cell communication and signaling : CCS.
2017 01; 15(1):3. doi:
10.1186/s12964-016-0158-6. [PMID: 28057038] - Marcus Pickhardt, Carmen Lawatscheck, Hans G Borner, Eckhard Mandelkow. Inhibition of Tau Protein Aggregation by Rhodanine-based Compounds Solubilized Via Specific Formulation Additives to Improve Bioavailability and Cell Viability.
Current Alzheimer research.
2017; 14(7):742-752. doi:
10.2174/1567205014666170202103136. [PMID: 28155596] - Heba El Gamal, Ali Hussein Eid, Shankar Munusamy. Renoprotective Effects of Aldose Reductase Inhibitor Epalrestat against High Glucose-Induced Cellular Injury.
BioMed research international.
2017; 2017(?):5903105. doi:
10.1155/2017/5903105. [PMID: 28386557] - Liudas Slepikas, Gianpaolo Chiriano, Remo Perozzo, Sébastien Tardy, Agata Kranjc, Ophélie Patthey-Vuadens, Hajer Ouertatani-Sakouhi, Sébastien Kicka, Christopher F Harrison, Tiziana Scrignari, Karl Perron, Hubert Hilbi, Thierry Soldati, Pierre Cosson, Eduardas Tarasevicius, Leonardo Scapozza. In Silico Driven Design and Synthesis of Rhodanine Derivatives as Novel Antibacterials Targeting the Enoyl Reductase InhA.
Journal of medicinal chemistry.
2016 12; 59(24):10917-10928. doi:
10.1021/acs.jmedchem.5b01620. [PMID: 26730986] - Martin Krátký, Šárka Štěpánková, Katarína Vorčáková, Jarmila Vinšová. Synthesis and in vitro evaluation of novel rhodanine derivatives as potential cholinesterase inhibitors.
Bioorganic chemistry.
2016 10; 68(?):23-9. doi:
10.1016/j.bioorg.2016.07.004. [PMID: 27428597] - Kaori Yama, Keisuke Sato, Yu Murao, Ryosuke Tatsunami, Yoshiko Tampo. Epalrestat Upregulates Heme Oxygenase-1, Superoxide Dismutase, and Catalase in Cells of the Nervous System.
Biological & pharmaceutical bulletin.
2016 Sep; 39(9):1523-30. doi:
10.1248/bpb.b16-00332. [PMID: 27439473] - Ke Liu, Naoko Kunii, Megumi Sakuma, Atsumi Yamaki, Satoru Mizuno, Mayu Sato, Hiromichi Sakai, Sayaka Kado, Kazuo Kumagai, Hirotatsu Kojima, Takayoshi Okabe, Tetsuo Nagano, Yasuhito Shirai, Fumio Sakane. A novel diacylglycerol kinase α-selective inhibitor, CU-3, induces cancer cell apoptosis and enhances immune response.
Journal of lipid research.
2016 Mar; 57(3):368-79. doi:
10.1194/jlr.m062794. [PMID: 26768655] - Doyeon Kim, Yun Gyeong Kim, Jae Hong Seo, Kye Jung Shin. Identification and characterization of potent, selective and metabolically stable IKKβ inhibitor.
Bioorganic & medicinal chemistry letters.
2016 Feb; 26(4):1120-3. doi:
10.1016/j.bmcl.2016.01.065. [PMID: 26826731] - Ahmed AbdelKhalek, Charles R Ashby, Bhargav A Patel, Tanaji T Talele, Mohamed N Seleem. In Vitro Antibacterial Activity of Rhodanine Derivatives against Pathogenic Clinical Isolates.
PloS one.
2016; 11(10):e0164227. doi:
10.1371/journal.pone.0164227. [PMID: 27711156] - Stella Cascioferro, Demetrio Raffa, Benedetta Maggio, Maria Valeria Raimondi, Domenico Schillaci, Giuseppe Daidone. Sortase A Inhibitors: Recent Advances and Future Perspectives.
Journal of medicinal chemistry.
2015 Dec; 58(23):9108-23. doi:
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Biological research.
2015 Jul; 48(?):39. doi:
10.1186/s40659-015-0032-9. [PMID: 26209329] - Kaori Yama, Keisuke Sato, Natsuki Abe, Yu Murao, Ryosuke Tatsunami, Yoshiko Tampo. Epalrestat increases glutathione, thioredoxin, and heme oxygenase-1 by stimulating Nrf2 pathway in endothelial cells.
Redox biology.
2015; 4(?):87-96. doi:
10.1016/j.redox.2014.12.002. [PMID: 25529839] - William Sinko, Yang Wang, Wei Zhu, Yonghui Zhang, Ferran Feixas, Courtney L Cox, Douglas A Mitchell, Eric Oldfield, J Andrew McCammon. Undecaprenyl diphosphate synthase inhibitors: antibacterial drug leads.
Journal of medicinal chemistry.
2014 Jul; 57(13):5693-701. doi:
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The Biochemical journal.
2014 Apr; 459(1):161-70. doi:
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Surgery.
2013 Apr; 153(4):555-64. doi:
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Journal of pharmaceutical and biomedical analysis.
2013 Feb; 74(?):227-34. doi:
10.1016/j.jpba.2012.10.020. [PMID: 23245255] - Keisuke Sato, Kaori Yama, Yu Murao, Ryosuke Tatsunami, Yoshiko Tampo. Epalrestat increases intracellular glutathione levels in Schwann cells through transcription regulation.
Redox biology.
2013; 2(?):15-21. doi:
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The American journal of Chinese medicine.
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PLoS pathogens.
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2012 Apr; 11(4):715-23. doi:
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Journal of ethnopharmacology.
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European journal of medicinal chemistry.
2010 Dec; 45(12):5827-32. doi:
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Journal of diabetes and its complications.
2010 Nov; 24(6):424-32. doi:
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Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences.
2010 Apr; 35(4):395-400. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2010 Feb; 107(7):3157-62. doi:
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The Journal of biological chemistry.
2009 Sep; 284(39):26742-8. doi:
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Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
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