INDIRUBIN-3-MONOXIME (BioDeep_00000393120)
代谢物信息卡片
3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one
化学式: C16H11N3O2 (277.0851)
中文名称: 靛玉红-3-单肟
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=C(C4=CC=CC=C4N3)N=O
InChI: InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H
描述信息
A member of the class of biindoles that is indirubin in which the keto group at position 3 has undergone condensation with hydroxylamine to form the corresponding oxime.
Indirubin-3'-monoxime is a potent GSK-3β inhibitor, and weakly inhibits 5-Lipoxygenase, with IC50s of 22 nM and 7.8-10 μM, respectively; Indirubin-3'-monoxime also shows inhibitory activities against CDK5/p25 and CDK1/cyclin B, with IC50s of 100 and 180 nM.
同义名列表
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:92352
- ChEBI: CHEBI:43645
- PubChem: 3707
- Metlin: METLIN45531
- DrugBank: DB02052
- ChEMBL: CHEMBL1496098
- ChEMBL: CHEMBL126077
- ChEMBL: CHEMBL216543
- CAS: 160807-49-8
- CAS: 667463-82-3
- PMhub: MS000243451
- MetaboLights: MTBLC43645
- medchemexpress: HY-19807
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
- Chunjie Jiang, Lu Qi, Jiang Xue, Yibiao Wang. Indirubin-3'-oxime promotes the efficacy of GnRHa in obese-induced central precocious puberty and maintains normal bone growth and body weight via the ERK-Sp1-KISS-1/GPR54 axis.
Cellular and molecular biology (Noisy-le-Grand, France).
2023 Apr; 69(4):188-194. doi:
10.14715/cmb/2023.69.4.29. [PMID: 37329527] - Alica Fischle, Rico Schwarz, Franziska Wendt, Marcel Kordt, Robert Ramer, Lars Boeckmann, Martin Hein, Peter Langer, Steffen Emmert, Brigitte Vollmar, Burkhard Hinz. A Sensitive LC-MS/MS Method for the Simultaneous Determination of Two Thia-Analogous Indirubin N-Glycosides and Indirubin-3'-Monoxime in Plasma and Cell Culture Medium.
Molecules (Basel, Switzerland).
2022 May; 27(9):. doi:
10.3390/molecules27093031. [PMID: 35566381] - Zhen Yu, Xiaojing Wei, Lanting Liu, Hao Sun, Teng Fang, Lu Wang, Ying Li, Weiwei Sui, Kefei Wang, Yi He, Yaozhong Zhao, Wenyang Huang, Gang An, Fancui Meng, Changjiang Huang, Tengteng Yu, Kenneth C Anderson, Tao Cheng, Lugui Qiu, Mu Hao. Indirubin-3'-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma.
EBioMedicine.
2022 Apr; 78(?):103950. doi:
10.1016/j.ebiom.2022.103950. [PMID: 35344764] - Henrike Rebl, Marie Sawade, Martin Hein, Claudia Bergemann, Manuela Wende, Michael Lalk, Peter Langer, Steffen Emmert, Barbara Nebe. Synergistic effect of plasma-activated medium and novel indirubin derivatives on human skin cancer cells by activation of the AhR pathway.
Scientific reports.
2022 02; 12(1):2528. doi:
10.1038/s41598-022-06523-x. [PMID: 35169210] - Hezhen Wang, Zhiyuan Wang, Chunyong Wei, Jing Wang, Yingshu Xu, Guohui Bai, Qizheng Yao, Lei Zhang, Yongzheng Chen. Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.
European journal of medicinal chemistry.
2021 Nov; 223(?):113652. doi:
10.1016/j.ejmech.2021.113652. [PMID: 34161865] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Nguyen Trong Dan, Hoang Duc Quang, Vuong Van Truong, Do Huu Nghi, Nguyen Manh Cuong, To Dao Cuong, Tran Quoc Toan, Long Giang Bach, Nguyen Huu Thuan Anh, Nguyen Thi Mai, Ngo Thi Lan, Luu Van Chinh, Pham Minh Quan. Design, synthesis, structure, in vitro cytotoxic activity evaluation and docking studies on target enzyme GSK-3β of new indirubin-3'-oxime derivatives.
Scientific reports.
2020 07; 10(1):11429. doi:
10.1038/s41598-020-68134-8. [PMID: 32651416] - Na Yoon Kim, Yong-Chul Kim, Yoon Gyoon Kim. Development of UHPLC-MS/MS Method for Indirubin-3'-Oxime Derivative as a Novel FLT3 Inhibitor and Pharmacokinetic Study in Rats.
Molecules (Basel, Switzerland).
2020 Apr; 25(9):. doi:
10.3390/molecules25092039. [PMID: 32349415] - Yasuhito Nobushi, Hiroaki Saito, Shinichi Miyairi, Taketo Uchiyama, Yukinaga Kishikawa. Inhibitory Effects of Indirubin-3'-oxime Derivatives on Lipid Accumulation in 3T3-L1 Cells.
Biological & pharmaceutical bulletin.
2020; 43(3):503-508. doi:
10.1248/bpb.b19-00910. [PMID: 32115509] - Saynaz A Choudhary, Nikita Bora, Dipanjan Banerjee, Leena Arora, Anindhya Sundar Das, Rakesh Yadav, Karl-Norbert Klotz, Durba Pal, Anupam Nath Jha, Suman Dasgupta. A novel small molecule A2A adenosine receptor agonist, indirubin-3'-monoxime, alleviates lipid-induced inflammation and insulin resistance in 3T3-L1 adipocytes.
The Biochemical journal.
2019 08; 476(16):2371-2391. doi:
10.1042/bcj20190251. [PMID: 31409652] - Chunqiu Liu, Peipei Jiang, Yuanhong Xu, Meijuan Zheng, Jinpin Qiao, Xueyong Zhou, Dake Huang, Maohong Bian. Inhibition of Suicidal Erythrocyte Death by Indirubin-3'-Monoxime.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2018; 45(3):1108-1120. doi:
10.1159/000487352. [PMID: 29439254] - Sandra Medina-Moreno, Thomas C Dowling, Juan C Zapata, Nhut M Le, Edward Sausville, Joseph Bryant, Robert R Redfield, Alonso Heredia. Targeting of CDK9 with indirubin 3'-monoxime safely and durably reduces HIV viremia in chronically infected humanized mice.
PloS one.
2017; 12(8):e0183425. doi:
10.1371/journal.pone.0183425. [PMID: 28817720] - Nicolas Gaboriaud-Kolar, Vasillios Myrianthopoulos, Konstantina Vougogiannopoulou, Panagiotis Gerolymatos, David A Horne, Richard Jove, Emmanuel Mikros, Sangkil Nam, Alexios-Leandros Skaltsounis. Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines.
Journal of natural products.
2016 10; 79(10):2464-2471. doi:
10.1021/acs.jnatprod.6b00285. [PMID: 27726390] - Shengquan Hu, Wei Cui, Zaijun Zhang, Shinghung Mak, Daping Xu, Gang Li, Yuanjia Hu, Yuqiang Wang, Mingyuen Lee, Karl Wahkeung Tsim, Yifan Han. Indirubin-3-Oxime Effectively Prevents 6OHDA-Induced Neurotoxicity in PC12 Cells via Activating MEF2D Through the Inhibition of GSK3β.
Journal of molecular neuroscience : MN.
2015 Dec; 57(4):561-70. doi:
10.1007/s12031-015-0638-y. [PMID: 26346600] - Chun-Tang Chiou, Wei-Chun Lee, Jiahn-Haur Liao, Jing-Jy Cheng, Lie-Chwen Lin, Chih-Yu Chen, Jen-Shin Song, Ming-Hsien Wu, Kak-Shan Shia, Wen-Tai Li. Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents.
European journal of medicinal chemistry.
2015 Jun; 98(?):1-12. doi:
10.1016/j.ejmech.2015.04.062. [PMID: 25988923] - Sorabh Sharma, Rajeev Taliyan. Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice.
Biochemical and biophysical research communications.
2014 Oct; 452(4):1009-15. doi:
10.1016/j.bbrc.2014.09.034. [PMID: 25234596] - O M Choi, Y-H Cho, S Choi, S-H Lee, S H Seo, H-Y Kim, G Han, D S Min, T Park, K Y Choi. The small molecule indirubin-3'-oxime activates Wnt/β-catenin signaling and inhibits adipocyte differentiation and obesity.
International journal of obesity (2005).
2014 Aug; 38(8):1044-52. doi:
10.1038/ijo.2013.209. [PMID: 24232498] - Alonso Heredia, Senthilkumar Natesan, Nhut M Le, Sandra Medina-Moreno, Juan C Zapata, Marvin Reitz, Joseph Bryant, Robert R Redfield. Indirubin 3'-monoxime, from a Chinese traditional herbal formula, suppresses viremia in humanized mice infected with multidrug-resistant HIV.
AIDS research and human retroviruses.
2014 May; 30(5):403-6. doi:
10.1089/aid.2013.0249. [PMID: 24401082] - Ming-Yang Lee, Yi-Wen Liu, Ming-Ho Chen, Jin-Yi Wu, Hsing-Ying Ho, Qwa-Fun Wang, Jing-Jing Chuang. Indirubin-3'-monoxime promotes autophagic and apoptotic death in JM1 human acute lymphoblastic leukemia cells and K562 human chronic myelogenous leukemia cells.
Oncology reports.
2013 May; 29(5):2072-8. doi:
10.3892/or.2013.2334. [PMID: 23468088] - Luisa F González Arbeláez, Ignacio A Pérez Núñez, Susana M Mosca. Gsk-3β inhibitors mimic the cardioprotection mediated by ischemic pre- and postconditioning in hypertensive rats.
BioMed research international.
2013; 2013(?):317456. doi:
10.1155/2013/317456. [PMID: 24288674] - Wan-Yu Lo, Nai-Wen Chang. An indirubin derivative, indirubin-3'-monoxime suppresses oral cancer tumorigenesis through the downregulation of survivin.
PloS one.
2013; 8(8):e70198. doi:
10.1371/journal.pone.0070198. [PMID: 23967071] - Frank G E Perabo, Gregor Landwehrs, Christian Frössler, Doris H Schmidt, S C Mueller. Antiproliferative and apoptosis inducing effects of indirubin-3'-monoxime in renal cell cancer cells.
Urologic oncology.
2011 Nov; 29(6):815-20. doi:
10.1016/j.urolonc.2009.10.005. [PMID: 19945313] - Ana T Varela, Ana P Gomes, Anabela M Simões, João S Teodoro, Filipe V Duarte, Anabela P Rolo, Carlos M Palmeira. Indirubin-3'-oxime impairs mitochondrial oxidative phosphorylation and prevents mitochondrial permeability transition induction.
Toxicology and applied pharmacology.
2008 Dec; 233(2):179-85. doi:
10.1016/j.taap.2008.08.005. [PMID: 18786556] - Lan Wang, Guang-Biao Zhou, Ping Liu, Jun-Hong Song, Yang Liang, Xiao-Jing Yan, Fang Xu, Bing-Shun Wang, Jian-Hua Mao, Zhi-Xiang Shen, Sai-Juan Chen, Zhu Chen. Dissection of mechanisms of Chinese medicinal formula Realgar-Indigo naturalis as an effective treatment for promyelocytic leukemia.
Proceedings of the National Academy of Sciences of the United States of America.
2008 Mar; 105(12):4826-31. doi:
10.1073/pnas.0712365105. [PMID: 18344322] - Julian C K Lui, Judy W Y Wong, Y K Suen, T T Kwok, K P Fung, S K Kong. Cordycepin induced eryptosis in mouse erythrocytes through a Ca2+-dependent pathway without caspase-3 activation.
Archives of toxicology.
2007 Dec; 81(12):859-65. doi:
10.1007/s00204-007-0214-5. [PMID: 17541556] - Yoan Ferandin, Karima Bettayeb, Marina Kritsanida, Olivier Lozach, Panagiotis Polychronopoulos, Prokopios Magiatis, Alexios-Leandros Skaltsounis, Laurent Meijer. 3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents.
Journal of medicinal chemistry.
2006 Jul; 49(15):4638-49. doi:
10.1021/jm060314i. [PMID: 16854069] - Frank G E Perabo, Christian Frössler, Gregor Landwehrs, Doris H Schmidt, Alexander von Rücker, Andreas Wirger, Stefan C Müller. Indirubin-3'-monoxime, a CDK inhibitor induces growth inhibition and apoptosis-independent up-regulation of survivin in transitional cell cancer.
Anticancer research.
2006 May; 26(3A):2129-35. doi:
. [PMID: 16827155] - F Peter Guengerich, Martha V Martin, W Andrew McCormick, Linh P Nguyen, Edward Glover, Christopher A Bradfield. Aryl hydrocarbon receptor response to indigoids in vitro and in vivo.
Archives of biochemistry and biophysics.
2004 Mar; 423(2):309-16. doi:
10.1016/j.abb.2004.01.002. [PMID: 15001395] - S Leclerc, M Garnier, R Hoessel, D Marko, J A Bibb, G L Snyder, P Greengard, J Biernat, Y Z Wu, E M Mandelkow, G Eisenbrand, L Meijer. Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors?.
The Journal of biological chemistry.
2001 Jan; 276(1):251-60. doi:
10.1074/jbc.m002466200. [PMID: 11013232]
