Isatin (BioDeep_00000858436)

Main id: BioDeep_00000003332

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


InChI=1\C8H5NO2\c10-7-5-3-1-2-4-6(5)9-8(7)11\h1-4H,(H,9,10,11

化学式: C8H5NO2 (147.032027)
中文名称: 靛红
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=O)C(=O)N2
InChI: InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

描述信息

COVID info from PDB, Protein Data Bank
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Isatin (Indoline-2,3-dione) is a potent inhibitor of monoamine oxidase (MAO) with an IC50 of 3 μM. Also binds to central benzodiazepine receptors (IC50 against clonazepam, 123 μM)[1]. Also acts as an antagonist of both atrial natriuretic peptide stimulated and nitric oxide-stimulated guanylate cyclase activity[2]. Shows effect on the serotonergic system[3].
Isatin (Indoline-2,3-dione) is a potent inhibitor of monoamine oxidase (MAO) with an IC50 of 3 μM. Also binds to central benzodiazepine receptors (IC50 against clonazepam, 123 μM)[1]. Also acts as an antagonist of both atrial natriuretic peptide stimulated and nitric oxide-stimulated guanylate cyclase activity[2]. Shows effect on the serotonergic system[3].

同义名列表

39 个代谢物同义名

InChI=1\C8H5NO2\c10-7-5-3-1-2-4-6(5)9-8(7)11\h1-4H,(H,9,10,11; 5-21-10-00221 (Beilstein Handbook Reference); o-Aminobenzoylformic anhydride; 2,3-Dioxo-2,3-dihydroindole; Isatinic acid anhydride; 1H-Indole-2,3-dione; Isatic acid lactam; Indoline-2,3-dione; 2,3-Diketoindoline; 2,3-Indolinedione; 2,3-Dioxoindoline; 2,3-Ketoindoline; EINECS 202-077-8; INDOLE-2,3-DIONE; WLN: T56 BMVVJ; 114618_ALDRICH; MLS001066355; ZINC01532171; Pseudoisatin; SMR000471835; 58240_FLUKA; CHEBI:27539; AIDS-020002; BRN 0383659; AIDS020002; 84788-92-1; 5815-00-9; AI3-03111; SBB009100; NSC 9262; Tribulin; NSC9262; 91-56-5; S00335a; Isatine; C11129; Isatin; Isotin; isn



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

45 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

  • Mohammad Altamimi, Saeed Ali Syed, Burak Tuzun, Mohammad Rashid Alhazani, Osamah Alnemer, Ahmed Bari. Synthesis biological evaluation and molecular docking of isatin hybrids as anti-cancer and anti-microbial agents. Journal of enzyme inhibition and medicinal chemistry. 2024 Dec; 39(1):2288548. doi: 10.1080/14756366.2023.2288548. [PMID: 38073431]
  • Heba E Saad, Gaber M Abu El-Reash, Mohamed Gaber, Mohamed A Hashem, Yasmeen G Abou El-Reash, Nuha Y Elamin, Mohamed R Elamin, Yusif S El-Sayed. A novel isatin Schiff based cerium complex: synthesis, characterization, antimicrobial activity and molecular docking studies. BMC genomics. 2024 Feb; 25(1):162. doi: 10.1186/s12864-024-10037-3. [PMID: 38331729]
  • Weihuan Zeng, Jun Qian, Yue Wang, Minyu Shou, Guoyin Kai. Bletilla Striata polysaccharides thermosensitive gel for photothermal treatment of bacterial infection. International journal of biological macromolecules. 2023 Oct; ?(?):127430. doi: 10.1016/j.ijbiomac.2023.127430. [PMID: 37838114]
  • Andrei V Bogdanov, Margarita Neganova, Alexandra Voloshina, Anna Lyubina, Syumbelya Amerhanova, Igor A Litvinov, Olga Tsivileva, Nurgali Akylbekov, Rakhmetulla Zhapparbergenov, Zulfiia Valiullina, Alexandr V Samorodov, Igor Alabugin. Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015119. [PMID: 37894799]
  • Shaohuan Liu, Shu Wang, Dan Xu, Bowen Pan, Linzhi Chen, Shijia Zhao, Zhi Xu, Wei Zhou. Novel ester tethered dihydroartemisinin-3-(oxime/thiosemicarbazide)isatin hybrids as potential anti-breast cancer agents: Synthesis, in vitro cytotoxicity and structure-activity relationship. Drug development research. 2023 May; ?(?):. doi: 10.1002/ddr.22078. [PMID: 37165798]
  • Zhi Xu, Bowen Pan, Linzhi Chen, Dan Xu. Design, synthesis, and in vitro cytotoxicity evaluation of novel dihydroartemisinin-isatin hybrids tethered via different length of esters as potential anti-breast cancer agents. Fitoterapia. 2023 Apr; 166(?):105436. doi: 10.1016/j.fitote.2023.105436. [PMID: 36693438]
  • Zhi Xu, Xiaoyan Zhang, Jie Liu, Shijia Zhao, Junna Liu, Wei Zhou. Design, Synthesis, and Biological Evaluation of Novel Amyl Ester Tethered Dihydroartemisinin-Isatin Hybrids as Potent Anti-Breast Cancer Agents. Chemistry & biodiversity. 2023 Mar; 20(3):e202201257. doi: 10.1002/cbdv.202201257. [PMID: 36808231]
  • Vishnu Nayak Badavath, Akhil Kumar, Pralok K Samanta, Siddhartha Maji, Anik Das, Galia Blum, Anjali Jha, Anik Sen. Determination of potential inhibitors based on isatin derivatives against SARS-CoV-2 main protease (mpro): a molecular docking, molecular dynamics and structure-activity relationship studies. Journal of biomolecular structure & dynamics. 2022 04; 40(7):3110-3128. doi: 10.1080/07391102.2020.1845800. [PMID: 33200681]
  • Nasima Arshad, Muhammad Ismail Mir, Fouzia Perveen, Aneela Javed, Memona Javaid, Aamer Saeed, Pervaiz Ali Channar, Shahid Iqbal Farooqi, Saad Alkahtani, Jamshed Anwar. Investigations on Anticancer Potentials by DNA Binding and Cytotoxicity Studies for Newly Synthesized and Characterized Imidazolidine and Thiazolidine-Based Isatin Derivatives. Molecules (Basel, Switzerland). 2022 Jan; 27(2):. doi: 10.3390/molecules27020354. [PMID: 35056668]
  • Divya Utreja, Komalpreet Kaur, Narpinderjeet K Dhillon, Rajesh K Pathak. 3-Hydroxy-3-alkylindolin-2-ones: regioselective synthesis, molecular docking and nematicidal studies against Meloidogyne incognita. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2022; 57(8):657-669. doi: 10.1080/03601234.2022.2097504. [PMID: 35930393]
  • Matt D Johansen, Shalini, Sumit Kumar, Clément Raynaud, Diana H Quan, Warwick J Britton, Philip M Hansbro, Vipan Kumar, Laurent Kremer. Biological and Biochemical Evaluation of Isatin-Isoniazid Hybrids as Bactericidal Candidates against Mycobacterium tuberculosis. Antimicrobial agents and chemotherapy. 2021 07; 65(8):e0001121. doi: 10.1128/aac.00011-21. [PMID: 33972252]
  • Paul Awolade, Nosipho Cele, Oluwakemi Ebenezer, Nagaraju Kerru, Lalitha Gummidi, Liang Gu, Gabriella Palma, Mandeep Kaur, Parvesh Singh. Synthesis of 1H-1,2,3-Triazole-Linked Quinoline-Isatin Molecular Hybrids as Anti-Breast Cancer and Anti-Methicillin-Resistant Staphylococcus aureus (MRSA) Agents. Anti-cancer agents in medicinal chemistry. 2021; 21(10):1228-1239. doi: 10.2174/1871520620666200929153138. [PMID: 32990543]
  • Konda Swathi, K Sowjanya, Lavanya Sara, P Naveena. Design, Characterization, and Docking Studies of Some Novel Isatin Derivatives for Anticonvulsant and Antidepressant Activity. Advances in experimental medicine and biology. 2021; 1339(?):359-369. doi: 10.1007/978-3-030-78787-5_44. [PMID: 35023126]
  • Komalpreet Kaur, Divya Utreja, Narpinderjeet K Dhillon, Rajesh K Pathak, Kamaljit Singh. N-alkyl isatin derivatives: Synthesis, nematicidal evaluation and protein target identifications for their mode of action. Pesticide biochemistry and physiology. 2021 Jan; 171(?):104736. doi: 10.1016/j.pestbp.2020.104736. [PMID: 33357558]
  • Pei Liu, Hongbo Liu, Qi Sun, Hao Liang, Chunmei Li, Xiaobing Deng, Ying Liu, Luhua Lai. Potent inhibitors of SARS-CoV-2 3C-like protease derived from N-substituted isatin compounds. European journal of medicinal chemistry. 2020 Nov; 206(?):112702. doi: 10.1016/j.ejmech.2020.112702. [PMID: 32798789]
  • Anne Suély Pinto Savall, Eduarda Monteiro Fidélis, Maria Eduarda Ziani Gutierrez, Bianca Barreto Martins, Vanessa Carratú Gervini, Robson Luiz Puntel, Daniel Henrique Roos, Daiana Silva Ávila, Simone Pinton. Pre-clinical evidence of safety and protective effect of isatin and oxime derivatives against malathion-induced toxicity. Basic & clinical pharmacology & toxicology. 2020 Apr; 126(4):399-410. doi: 10.1111/bcpt.13359. [PMID: 31694074]
  • Yong Wang, Wing-Lam Cheong, Zhiguang Liang, Lok-Yan So, Kin-Fai Chan, Pui-Kin So, Yu Wai Chen, Wing-Leung Wong, Kwok-Yin Wong. Hydrophobic substituents on isatin derivatives enhance their inhibition against bacterial peptidoglycan glycosyltransferase activity. Bioorganic chemistry. 2020 04; 97(?):103710. doi: 10.1016/j.bioorg.2020.103710. [PMID: 32146179]
  • Ya-Zhou Zhang, Hong-Zhi Du, Hai-Lin Liu, Qian-Song He, Zhi Xu. Isatin dimers and their biological activities. Archiv der Pharmazie. 2020 Mar; 353(3):e1900299. doi: 10.1002/ardp.201900299. [PMID: 31985855]
  • Mingli Yang, Hailin Liu, Yazhou Zhang, Xiujun Wang, Zhi Xu. Moxifloxacin-isatin Hybrids Tethered by 1,2,3-triazole and their Anticancer Activities. Current topics in medicinal chemistry. 2020; 20(16):1461-1467. doi: 10.2174/1568026620666200128144825. [PMID: 31994464]
  • L L S F R Dantas, A G Fonseca, J R Pereira, A A Furtado, P A T M Gomes, M F Fernandes-Pedrosa, A C L Leite, M J B M Rêgo, M G R Pitta, T M A M Lemos. Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2020; 53(10):e10204. doi: 10.1590/1414-431x202010204. [PMID: 32901685]
  • Govindasami Periyasami, Paulrayer Antonisamy, Karthikeyan Perumal, Antony Stalin, Mostafizur Rahaman, Asma A Alothman. A competent synthesis and efficient anti-inflammatory responses of isatinimino acridinedione moiety via suppression of in vivo NF-κB, COX-2 and iNOS signaling. Bioorganic chemistry. 2019 09; 90(?):103047. doi: 10.1016/j.bioorg.2019.103047. [PMID: 31234130]
  • Sara Zeeshan, Muhammad Naveed, Adnan Khan, Ayesha Atiq, Maryam Arif, Muhammad Naeem Ahmed, Yeong Shik Kim, Salman Khan. N-Pyrazoloyl and N-thiopheneacetyl hydrazone of isatin exhibited potent anti-inflammatory and anti-nociceptive properties through suppression of NF-κB, MAPK and oxidative stress signaling in animal models of inflammation. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2019 Jul; 68(7):613-632. doi: 10.1007/s00011-019-01245-9. [PMID: 31079165]
  • Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
  • Babita Aneja, Nashrah Sharif Khan, Parvez Khan, Aarfa Queen, Afzal Hussain, Md Tabish Rehman, Mohamed F Alajmi, Hesham R El-Seedi, Sher Ali, Md Imtaiyaz Hassan, Mohammad Abid. Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis. European journal of medicinal chemistry. 2019 Feb; 163(?):840-852. doi: 10.1016/j.ejmech.2018.12.026. [PMID: 30579124]
  • Wenyan Gao, Luding Zhang, Xiaoqian Wang, Li Yu, Changhong Wang, Yang Gong. The combination of indirubin and isatin attenuates dextran sodium sulfate induced ulcerative colitis in mice. Biochemistry and cell biology = Biochimie et biologie cellulaire. 2018 10; 96(5):636-645. doi: 10.1139/bcb-2018-0041. [PMID: 29671340]
  • Qiaomei Jin, Jian Zhang, Cuihua Jiang, Dongjian Zhang, Meng Gao, Shihe Hu. Self [3 + 4] Cycloadditions of Isatin N, N'-Cyclic Azomethine Imine 1,3-Dipole with N-( o-Chloromethyl)aryl Amides. The Journal of organic chemistry. 2018 08; 83(15):8410-8416. doi: 10.1021/acs.joc.8b01055. [PMID: 29846070]
  • Xiaoze Bao, Shiqiang Wei, Xingkai Qian, Jingping Qu, Baomin Wang, Liwei Zou, Guangbo Ge. Asymmetric Construction of a Multi-Pharmacophore-Containing Dispirotriheterocyclic Scaffold and Identification of a Human Carboxylesterase 1 Inhibitor. Organic letters. 2018 06; 20(11):3394-3398. doi: 10.1021/acs.orglett.8b01316. [PMID: 29786435]
  • Anirban Ganguly, Hari Krishna Reddy Rachamalla, Dwaipayan Bhattacharya, Keerti Bhamidipati, Abhishek Pal, Halley Gora Ravuri, Sumana Chakravarty, Susanta Sekhar Adhikari, Rajkumar Banerjee. Oestrogen receptor-mediated liposomal drug delivery for treating melanoma. Journal of drug targeting. 2018 Jun; 26(5-6):481-493. doi: 10.1080/1061186x.2018.1433679. [PMID: 29376759]
  • Bence Szilágyi, Péter Kovács, György G Ferenczy, Anita Rácz, Krisztina Németh, Júlia Visy, Pál Szabó, Janez Ilas, György T Balogh, Katalin Monostory, István Vincze, Tamás Tábi, Éva Szökő, György M Keserű. Discovery of isatin and 1H-indazol-3-ol derivatives as d-amino acid oxidase (DAAO) inhibitors. Bioorganic & medicinal chemistry. 2018 05; 26(8):1579-1587. doi: 10.1016/j.bmc.2018.02.004. [PMID: 29472125]
  • Mary Ensch, Vanessa Y Maldonado, Greg M Swain, Robert Rechenberg, Michael F Becker, Thomas Schuelke, Cory A Rusinek. Isatin Detection Using a Boron-Doped Diamond 3-in-1 Sensing Platform. Analytical chemistry. 2018 02; 90(3):1951-1958. doi: 10.1021/acs.analchem.7b04045. [PMID: 29298039]
  • Manoela Viar Fogaça, Priscila de Matos Cândido-Bacani, Lucas Milanez Benicio, Lara Martinelli Zapata, Priscilla de Freitas Cardoso, Marcelo Tempesta de Oliveira, Tamara Regina Calvo, Eliana Aparecida Varanda, Wagner Vilegas, Ilce Mara de Syllos Cólus. Effects of indirubin and isatin on cell viability, mutagenicity, genotoxicity and BAX/ERCC1 gene expression. Pharmaceutical biology. 2017 Dec; 55(1):2005-2014. doi: 10.1080/13880209.2017.1354387. [PMID: 28738722]
  • Tarek B Ahmad, David Rudd, Joshua Smith, Michael Kotiw, Peter Mouatt, Lisa M Seymour, Lei Liu, Kirsten Benkendorff. Anti-Inflammatory Activity and Structure-Activity Relationships of Brominated Indoles from a Marine Mollusc. Marine drugs. 2017 May; 15(5):. doi: 10.3390/md15050133. [PMID: 28481239]
  • Moustafa T Gabr, Nadia S El-Gohary, Eman R El-Bendary, Mohamed M El-Kerdawy, Nanting Ni. Isatin-β-thiocarbohydrazones: Microwave-assisted synthesis, antitumor activity and structure-activity relationship. European journal of medicinal chemistry. 2017 Mar; 128(?):36-44. doi: 10.1016/j.ejmech.2017.01.030. [PMID: 28147307]
  • Maninder Kaur, Manjinder Singh, Navriti Chadha, Om Silakari. Oxindole: A chemical prism carrying plethora of therapeutic benefits. European journal of medicinal chemistry. 2016 Nov; 123(?):858-894. doi: 10.1016/j.ejmech.2016.08.011. [PMID: 27543880]
  • Jinning Hou, Kang Jin, Jin Li, Yuqi Jiang, Xiaoyang Li, Xuejian Wang, Yongxue Huang, Yingjie Zhang, Wenfang Xu. LJNK, an indoline-2,3-dione-based aminopeptidase N inhibitor with promising antitumor potency. Anti-cancer drugs. 2016 07; 27(6):496-507. doi: 10.1097/cad.0000000000000351. [PMID: 26872309]
  • Maria C A Melo, Luciana R Teixeira, Laercio Pol-Fachin, Claudio G Rodrigues. Inhibition of the hemolytic activity caused by Staphylococcus aureus alpha-hemolysin through isatin-Schiff copper(II) complexes. FEMS microbiology letters. 2016 Jan; 363(1):fnv207. doi: 10.1093/femsle/fnv207. [PMID: 26519261]
  • A Ren, Q Wang, Z Fang, M Gao, H Wang, J Zhang, W Xu, W Yue, L Yin, Z Liu, X Li, B Ding. Pharmacokinetic study of isatin in dog plasma by liquid chromatography tandem mass spectrometry. Panminerva medica. 2015 Dec; 57(4):177-82. doi: NULL. [PMID: 26018409]
  • Maria Damgaard, Anas Al-Khawaja, Stine B Vogensen, Andreas Jurik, Maarten Sijm, Maria E K Lie, Mathias I Bæk, Emil Rosenthal, Anders A Jensen, Gerhard F Ecker, Bente Frølund, Petrine Wellendorph, Rasmus P Clausen. Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3. ACS chemical neuroscience. 2015 Sep; 6(9):1591-9. doi: 10.1021/acschemneuro.5b00150. [PMID: 26154082]
  • Theis Sommer, Kaare Bjerregaard-Andersen, Stine Marie Simensen, Jan K Jensen, Bjarne Jochimsen, Patrick J Riss, Michael Etzerodt, J Preben Morth. Enzymatic detection and quantification assay of isatin, a putative stress biomarker in blood. ACS chemical neuroscience. 2015 Aug; 6(8):1353-60. doi: 10.1021/cn500346x. [PMID: 25891478]
  • Ayman El-Faham, Muhammad Farooq, Sherine N Khattab, Nael Abutaha, Mohammad A Wadaan, Hazem A Ghabbour, Hoong-Kun Fun. Synthesis, Characterization, and Anti-Cancer Activity of Some New N'-(2-Oxoindolin-3-ylidene)-2-propylpentane hydrazide-hydrazones Derivatives. Molecules (Basel, Switzerland). 2015 Aug; 20(8):14638-55. doi: 10.3390/molecules200814638. [PMID: 26287132]
  • Panupun Limpachayaporn, Stefan Wagner, Klaus Kopka, Otmar Schober, Michael Schäfers, Günter Haufe. Synthesis of 7-halogenated isatin sulfonamides: nonradioactive counterparts of caspase-3/-7 inhibitor-based potential radiopharmaceuticals for molecular imaging of apoptosis. Journal of medicinal chemistry. 2014 Nov; 57(22):9383-95. doi: 10.1021/jm500718e. [PMID: 25358116]
  • Babak Esmaeelian, Catherine A Abbott, Richard K Le Leu, Kirsten Benkendorff. 6-bromoisatin found in muricid mollusc extracts inhibits colon cancer cell proliferation and induces apoptosis, preventing early stage tumor formation in a colorectal cancer rodent model. Marine drugs. 2013 Dec; 12(1):17-35. doi: 10.3390/md12010017. [PMID: 24368567]
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