Maytansine (BioDeep_00000008198)

 

Secondary id: BioDeep_00000395681

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[acetyl(methyl)amino]propanoate

化学式: C34H46ClN3O10 (691.2871566)
中文名称: 美坦新
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.81%

分子结构信息

SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
InChI: InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11-

描述信息

D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product
C1907 - Drug, Natural Product
Same as: D04864
Maytansine is a highly potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at subnanomolar concentrations[1].

同义名列表

5 个代谢物同义名

[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[acetyl(methyl)amino]propanoate; Maytansine; Maitansine; NSC 153858; Maytansine



数据库引用编号

18 个数据库交叉引用编号

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)

4 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

  • Ryuto Tomabechi, Miki Miyasato, Taeka Sato, Tappei Takada, Kei Higuchi, Hisanao Kishimoto, Yoshiyuki Shirasaka, Katsuhisa Inoue. Identification of 5-Carboxyfluorescein as a Probe Substrate of SLC46A3 and Its Application in a Fluorescence-Based In Vitro Assay Evaluating the Interaction with SLC46A3. Molecular pharmaceutics. 2023 01; 20(1):491-499. doi: 10.1021/acs.molpharmaceut.2c00741. [PMID: 36458938]
  • Clemence Pouzin, Leonid Gibiansky, Nathalie Fagniez, Mustapha Chadjaa, Michel Tod, Laurent Nguyen. Integrated multiple analytes and semi-mechanistic population pharmacokinetic model of tusamitamab ravtansine, a DM4 anti-CEACAM5 antibody-drug conjugate. Journal of pharmacokinetics and pharmacodynamics. 2022 06; 49(3):381-394. doi: 10.1007/s10928-021-09799-0. [PMID: 35166967]
  • Hai-Na Xie, Yu-Yuan Chen, Guo-Biao Zhu, Hai-Hao Han, Xi-Le Hu, Zhi-Qiang Pan, Yi Zang, Dong-Hao Xie, Xiao-Peng He, Jia Li, Tony D James. Targeted delivery of maytansine to liver cancer cells via galactose-modified supramolecular two-dimensional glycomaterial. Chemical communications (Cambridge, England). 2022 Apr; 58(32):5029-5032. doi: 10.1039/d1cc06809a. [PMID: 35373789]
  • Yunlin Fu, Shashank Gorityala, Wenkui Li, David Humphries, Aaron Ledvina, Stephanie Cape, Franck Picard. Sensitive LC-MS/MS quantification of unconjugated maytansinoid DM4 and its metabolite S-methyl-DM4 in human plasma. Bioanalysis. 2022 Mar; 14(6):357-368. doi: 10.4155/bio-2021-0275. [PMID: 35234045]
  • Chao Xu, Shaojie Liu, Fa Yang, Keying Zhang, Yu Li, Xiaolong Zhao, Jiayu Zhang, Tong Lu, Shiqi Lu, Yao Jiang, Weijun Qin, Changhong Shi, Rui Zhang, An-Gang Yang, Aizhi Zhao, Donghui Han, Weihong Wen. Antibody-drug conjugates targeting CD248+ myofibroblasts effectively alleviate renal fibrosis in mice. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2022 02; 36(2):e22102. doi: 10.1096/fj.202101441r. [PMID: 34972243]
  • Yuan-Yuan Huang, Lu Chen, Guo-Xu Ma, Xu-Dong Xu, Xue-Gong Jia, Fu-Sheng Deng, Xue-Jian Li, Jing-Quan Yuan. A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154563. [PMID: 34361712]
  • Li Li, Chanrui Wang, Yijue Wu, Lihou Dong, Fang Chen, Kelly Dong, Haifeng Song. Simple and Rapid LC-MS/MS Methods for Quantifying Catabolites of Antibody-Drug Conjugates with SMCC Linker. Journal of chromatographic science. 2021 Jun; 59(7):642-649. doi: 10.1093/chromsci/bmaa122. [PMID: 33420505]
  • Juan Li, Siyu Guo, Qiang Hua, Fengxian Hu. Improved AP-3 production through combined ARTP mutagenesis, fermentation optimization, and subsequent genome shuffling. Biotechnology letters. 2021 Jun; 43(6):1143-1154. doi: 10.1007/s10529-020-03034-5. [PMID: 33751317]
  • Pengcheng Xu, Ru Wang, Wenqian Yang, Yanyan Liu, Dongsheng He, Zixuan Ye, Daquan Chen, Yuan Ding, Jiasheng Tu, Yan Shen. A DM1-doped porous gold nanoshell system for NIR accelerated redox-responsive release and triple modal imaging guided photothermal synergistic chemotherapy. Journal of nanobiotechnology. 2021 Mar; 19(1):77. doi: 10.1186/s12951-021-00824-5. [PMID: 33741008]
  • Tengteng Yu, Bharat Chaganty, Liang Lin, Lijie Xing, Boopathy Ramakrishnan, Kenneth Wen, Phillip A Hsieh, Andrew Wollacott, Karthik Viswanathan, Hedy Adari, Shih-Feng Cho, Yuyin Li, Hailin Chen, Wenjuan Yang, Yan Xu, Gang An, Lugui Qiu, Nikhil Munshi, Gregory Babcock, Zachary Shriver, James R Myette, Kenneth C Anderson, Yu-Tzu Tai. VIS832, a novel CD138-targeting monoclonal antibody, potently induces killing of human multiple myeloma and further synergizes with IMiDs or bortezomib in vitro and in vivo. Blood cancer journal. 2020 11; 10(11):110. doi: 10.1038/s41408-020-00378-z. [PMID: 33149123]
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  • Vineesh Indira Chandran, Ann-Sofie Månsson, Magdalena Barbachowska, Myriam Cerezo-Magaña, Björn Nodin, Bharat Joshi, Neelima Koppada, Ola M Saad, Oleg Gluz, Karolin Isaksson, Signe Borgquist, Karin Jirström, Ivan Robert Nabi, Helena Jernström, Mattias Belting. Hypoxia Attenuates Trastuzumab Uptake and Trastuzumab-Emtansine (T-DM1) Cytotoxicity through Redistribution of Phosphorylated Caveolin-1. Molecular cancer research : MCR. 2020 04; 18(4):644-656. doi: 10.1158/1541-7786.mcr-19-0856. [PMID: 31900313]
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  • Wen Jin, Lyle Burton, Ian Moore. LC-HRMS quantitation of intact antibody drug conjugate trastuzumab emtansine from rat plasma. Bioanalysis. 2018 Jun; 10(11):851-862. doi: 10.4155/bio-2018-0003. [PMID: 29863890]
  • Cornelius Cilliers, Bruna Menezes, Ian Nessler, Jennifer Linderman, Greg M Thurber. Improved Tumor Penetration and Single-Cell Targeting of Antibody-Drug Conjugates Increases Anticancer Efficacy and Host Survival. Cancer research. 2018 02; 78(3):758-768. doi: 10.1158/0008-5472.can-17-1638. [PMID: 29217763]
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  • Noriko Iwamoto, Akihiko Shimomura, Kenji Tamura, Akinobu Hamada, Takashi Shimada. LC-MS bioanalysis of Trastuzumab and released emtansine using nano-surface and molecular-orientation limited (nSMOL) proteolysis and liquid-liquid partition in plasma of Trastuzumab emtansine-treated breast cancer patients. Journal of pharmaceutical and biomedical analysis. 2017 Oct; 145(?):33-39. doi: 10.1016/j.jpba.2017.06.032. [PMID: 28648785]
  • Chunze Li, Priya Agarwal, Ekaterina Gibiansky, Jin Yan Jin, Susan Dent, Anthony Gonçalves, Ihsan Nijem, Alexander Strasak, Marie-Laurence Harle-Yge, Nataliya Chernyukhin, Pat LoRusso, Sandhya Girish. A Phase I Pharmacokinetic Study of Trastuzumab Emtansine (T-DM1) in Patients with Human Epidermal Growth Factor Receptor 2-Positive Metastatic Breast Cancer and Normal or Reduced Hepatic Function. Clinical pharmacokinetics. 2017 09; 56(9):1069-1080. doi: 10.1007/s40262-016-0496-y. [PMID: 27995530]
  • Kathleen N Moore, Hossein Borghaei, David M O'Malley, Woondong Jeong, Shelly M Seward, Todd M Bauer, Raymond P Perez, Ursula A Matulonis, Kelli L Running, Xiaoyan Zhang, Jose F Ponte, Rodrigo Ruiz-Soto, Michael J Birrer. Phase 1 dose-escalation study of mirvetuximab soravtansine (IMGN853), a folate receptor α-targeting antibody-drug conjugate, in patients with solid tumors. Cancer. 2017 Aug; 123(16):3080-3087. doi: 10.1002/cncr.30736. [PMID: 28440955]
  • Ping Zhong, Hao Meng, Jie Qiu, Jian Zhang, Huanli Sun, Ru Cheng, Zhiyuan Zhong. αvβ3 Integrin-targeted reduction-sensitive micellar mertansine prodrug: Superb drug loading, enhanced stability, and effective inhibition of melanoma growth in vivo. Journal of controlled release : official journal of the Controlled Release Society. 2017 08; 259(?):176-186. doi: 10.1016/j.jconrel.2016.12.011. [PMID: 27986551]
  • Dennis Eckelmann, Souvik Kusari, Michael Spiteller. Spatial profiling of maytansine during the germination process of Maytenus senegalensis seeds. Fitoterapia. 2017 Jun; 119(?):51-56. doi: 10.1016/j.fitote.2017.03.014. [PMID: 28385670]
  • Li-Wei Yap, Jesper Brok, Kathy Pritchard-Jones. Role of CD56 in Normal Kidney Development and Wilms Tumorigenesis. Fetal and pediatric pathology. 2017 Feb; 36(1):62-75. doi: 10.1080/15513815.2016.1256358. [PMID: 27935326]
  • Yang Li, Yanhong Duo, Shiyun Bao, Lisheng He, Kai Ling, Jinfeng Luo, Yue Zhang, Hao Huang, Han Zhang, Xiaofang Yu. EpCAM aptamer-functionalized polydopamine-coated mesoporous silica nanoparticles loaded with DM1 for targeted therapy in colorectal cancer. International journal of nanomedicine. 2017; 12(?):6239-6257. doi: 10.2147/ijn.s143293. [PMID: 28894364]
  • Mark A Socinski, Frederic J Kaye, David R Spigel, Fred J Kudrik, Santiago Ponce, Peter M Ellis, Margarita Majem, Paul Lorigan, Leena Gandhi, Martin E Gutierrez, Dale Nepert, Jesus Corral, Luis Paz Ares. Phase 1/2 Study of the CD56-Targeting Antibody-Drug Conjugate Lorvotuzumab Mertansine (IMGN901) in Combination With Carboplatin/Etoposide in Small-Cell Lung Cancer Patients With Extensive-Stage Disease. Clinical lung cancer. 2017 01; 18(1):68-76.e2. doi: 10.1016/j.cllc.2016.09.002. [PMID: 28341109]
  • Dennis Eckelmann, Souvik Kusari, Michael Spiteller. Occurrence and spatial distribution of maytansinoids in Putterlickia pyracantha, an unexplored resource of anticancer compounds. Fitoterapia. 2016 Sep; 113(?):175-81. doi: 10.1016/j.fitote.2016.08.006. [PMID: 27521896]
  • Jose F Ponte, Xiuxia Sun, Nicholas C Yoder, Nathan Fishkin, Rassol Laleau, Jennifer Coccia, Leanne Lanieri, Megan Bogalhas, Lintao Wang, Sharon Wilhelm, Wayne Widdison, Jan Pinkas, Thomas A Keating, Ravi Chari, Hans K Erickson, John M Lambert. Understanding How the Stability of the Thiol-Maleimide Linkage Impacts the Pharmacokinetics of Lysine-Linked Antibody-Maytansinoid Conjugates. Bioconjugate chemistry. 2016 07; 27(7):1588-98. doi: 10.1021/acs.bioconjchem.6b00117. [PMID: 27174129]
  • Markus Walles, Bettina Rudolph, Thierry Wolf, Julien Bourgailh, Martina Suetterlin, Thomas Moenius, Gisela Peraus, Olivier Heudi, Walid Elbast, Christian Lanshoeft, Sanela Bilic. New Insights in Tissue Distribution, Metabolism, and Excretion of [3H]-Labeled Antibody Maytansinoid Conjugates in Female Tumor-Bearing Nude Rats. Drug metabolism and disposition: the biological fate of chemicals. 2016 07; 44(7):897-910. doi: 10.1124/dmd.115.069021. [PMID: 27122302]
  • Rachelle L Dillon, Shilpa Chooniedass, Arjune Premsukh, Gregory P Adams, Joycelyn Entwistle, Glen C MacDonald, Jeannick Cizeau. Trastuzumab-deBouganin Conjugate Overcomes Multiple Mechanisms of T-DM1 Drug Resistance. Journal of immunotherapy (Hagerstown, Md. : 1997). 2016 Apr; 39(3):117-26. doi: 10.1097/cji.0000000000000115. [PMID: 26938945]
  • Haoheng Yan, Yukinori Endo, Yi Shen, David Rotstein, Milos Dokmanovic, Nishant Mohan, Partha Mukhopadhyay, Bin Gao, Pal Pacher, Wen Jin Wu. Ado-Trastuzumab Emtansine Targets Hepatocytes Via Human Epidermal Growth Factor Receptor 2 to Induce Hepatotoxicity. Molecular cancer therapeutics. 2016 Mar; 15(3):480-90. doi: 10.1158/1535-7163.mct-15-0580. [PMID: 26712117]
  • Olivier Heudi, Samuel Barteau, Franck Picard, Olivier Kretz. Quantitative analysis of maytansinoid (DM1) in human serum by on-line solid phase extraction coupled with liquid chromatography tandem mass spectrometry - Method validation and its application to clinical samples. Journal of pharmaceutical and biomedical analysis. 2016 Feb; 120(?):322-32. doi: 10.1016/j.jpba.2015.12.026. [PMID: 26771131]
  • Yong-Guang Zhang, Qing Liu, Hong-Fei Wang, Dong-Jin Park, Jian-Wei Guo, Chang-Jin Kim, Yuan-Ming Zhang, Wen-Jun Li. Nocardiopsis ansamitocini sp. nov., a new producer of ansamitocin P-3 of the genus Nocardiopsis. International journal of systematic and evolutionary microbiology. 2016 Jan; 66(1):230-235. doi: 10.1099/ijsem.0.000703. [PMID: 26486850]
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  • Rémy Gébleux, Sarah Wulhfard, Giulio Casi, Dario Neri. Antibody Format and Drug Release Rate Determine the Therapeutic Activity of Noninternalizing Antibody-Drug Conjugates. Molecular cancer therapeutics. 2015 Nov; 14(11):2606-12. doi: 10.1158/1535-7163.mct-15-0480. [PMID: 26294742]
  • Ben-Quan Shen, Daniela Bumbaca, Qin Yue, Ola Saad, Jay Tibbitts, S Cyrus Khojasteh, Sandhya Girish. Non-Clinical Disposition and Metabolism of DM1, a Component of Trastuzumab Emtansine (T-DM1), in Sprague Dawley Rats. Drug metabolism letters. 2015; 9(2):119-31. doi: 10.2174/1872312809666150602151922. [PMID: 26031461]
  • Hirdesh Uppal, Estelle Doudement, Kaushiki Mahapatra, Walter C Darbonne, Daniela Bumbaca, Ben-Quan Shen, Xiaoyan Du, Ola Saad, Kristin Bowles, Steve Olsen, Gail D Lewis Phillips, Dylan Hartley, Mark X Sliwkowski, Sandhya Girish, Donna Dambach, Vanitha Ramakrishnan. Potential mechanisms for thrombocytopenia development with trastuzumab emtansine (T-DM1). Clinical cancer research : an official journal of the American Association for Cancer Research. 2015 Jan; 21(1):123-33. doi: 10.1158/1078-0432.ccr-14-2093. [PMID: 25370470]
  • Souvik Kusari, Marc Lamshöft, Parijat Kusari, Sebastian Gottfried, Sebastian Zühlke, Kathrin Louven, Ute Hentschel, Oliver Kayser, Michael Spiteller. Endophytes are hidden producers of maytansine in Putterlickia roots. Journal of natural products. 2014 Dec; 77(12):2577-84. doi: 10.1021/np500219a. [PMID: 25478947]
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