10-Deacetylbaccatin III (BioDeep_00000002134)

 

Secondary id: BioDeep_00000230418

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


7-epi-10-Deacetylbaccatin III

化学式: C29H36O10 (544.2308356)
中文名称: 10-脱乙酰基巴卡丁Ⅲ, 10-脱乙酰基巴卡丁 III (10-DAB)
谱图信息: 最多检出来源 Viridiplantae(plant) 0.1%

分子结构信息

SMILES: CC(=O)OC12COC1CC(O)C1(C)C(=O)C(O)C3=C(C)C(O)CC(O)(C(OC(=O)c4ccccc4)C21)C3(C)C
InChI: InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1

描述信息

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.908
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.907
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2261
10-Deacetylbaccatin-III is an intermediate for taxol analog preparations. IC50 value: Target: Taxols have exhibit antitumor agents. Several of these taxols can be synthesized from 10- Deacetylbaccatin-III. 10-Deacetylbaccine III is the fifth intermediate of paclitaxel biosynthesis. The biosynthetic pathway consists of approximately 20 enzymatic steps but is not fully elucidated. 10-Deacetylbaccine III is an antineoplastic agent and an anti-cancer intermediate.
10-Deacetylbaccatin-III is an intermediate for taxol analog preparations. IC50 value: Target: Taxols have exhibit antitumor agents. Several of these taxols can be synthesized from 10- Deacetylbaccatin-III. 10-Deacetylbaccine III is the fifth intermediate of paclitaxel biosynthesis. The biosynthetic pathway consists of approximately 20 enzymatic steps but is not fully elucidated. 10-Deacetylbaccine III is an antineoplastic agent and an anti-cancer intermediate.

同义名列表

5 个代谢物同义名

7-epi-10-Deacetylbaccatin III; 10-Deacetylbaccatin III; 10-deacetylbaccatin (10-DAB); 10-DEACETYLBACCATIN-III; 10-Deacetylbaccatin III



数据库引用编号

26 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(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • taxol biosynthesis: acetyl-CoA + taxa-4(20),11-dien-5α-ol ⟶ coenzyme A + taxa-4(20),11-dien-5-α-yl acetate

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • taxol biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + taxa-4(20),11-dien-5α-ol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + taxa-4(20),11-dien-5α,13α-diol

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

122 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

  • Xiaodan Wu, Ying Wang, Bingyang Qin, Guansong Shao, Zihan Wang, Tao Wang, Yujie Fu. A nanocellulose molecularly imprinted membrane: Preparation, characterization and application in targeted separation of taxane 10-deacetylbaccatin III. International journal of biological macromolecules. 2023 Sep; ?(?):126794. doi: 10.1016/j.ijbiomac.2023.126794. [PMID: 37699463]
  • Md Nurullah, Zakiya Usmani, Sheeraz Ahmad, Bibhu Prasad Panda, Saima Amin, Showkat Rasool Mir. Purification and characterization of Taxol and 10-Deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high-performance liquid chromatography, ultra-high-performance liquid chromatography-mass spectrometry, and nuclear magnetic resonance. Journal of separation science. 2023 Jan; ?(?):e2200841. doi: 10.1002/jssc.202200841. [PMID: 36695632]
  • Balabhadrapatruni V S K Chakravarthi, Satpal Singh, Subban Kamalraj, Vijai Kumar Gupta, Chelliah Jayabaskaran. Evaluation of spore inoculum and confirmation of pathway genetic blueprint of T13αH and DBAT from a Taxol-producing endophytic fungus. Scientific reports. 2020 12; 10(1):21139. doi: 10.1038/s41598-020-77605-x. [PMID: 33273486]
  • Balendra Sah, Kamalraj Subban, Chelliah Jayabaskaran. Biochemical insights into the recombinant 10-deacetylbaccatin III-10-β-O-acetyltransferase enzyme from the Taxol-producing endophytic fungus Lasiodiplodia theobromae. FEMS microbiology letters. 2019 04; 366(7):. doi: 10.1093/femsle/fnz072. [PMID: 31062024]
  • Bi Wang, Shu Xu, Yan Cao, Fei Liu, Xingzeng Zhao, Xu Feng. Fungicidal activity of 10-deacetylbacatin III against Phytophthora capsici via inhibiting lysine biosynthesis. Pesticide biochemistry and physiology. 2018 Nov; 152(?):114-121. doi: 10.1016/j.pestbp.2018.09.008. [PMID: 30497701]
  • Bing-Juan Li, Hao Wang, Ting Gong, Jing-Jing Chen, Tian-Jiao Chen, Jin-Ling Yang, Ping Zhu. Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production. Nature communications. 2017 05; 8(?):15544. doi: 10.1038/ncomms15544. [PMID: 28516951]
  • Xueli Zhang, Jiajia Lv, Liling Wang, Hua Shao. Comparison of Pharmacokinetics and Biodistribution of 10-Deacetylbaccatin III after Oral Administration as Pure Compound or in Taxus chinensis Extract: A Pilot Study. Planta medica. 2016 Feb; 82(3):230-7. doi: 10.1055/s-0035-1558207. [PMID: 26838275]
  • Gennadi Gudi, Andrea Krähmer, Iraj Koudous, Jochen Strube, Hartwig Schulz. Infrared and Raman spectroscopic methods for characterization of Taxus baccata L.--Improved taxane isolation by accelerated quality control and process surveillance. Talanta. 2015 Oct; 143(?):42-49. doi: 10.1016/j.talanta.2015.04.090. [PMID: 26078126]
  • Yang-qin Tang, Hai-chi Li, Wen-jie Huang, Yan Xiong, Fa-huan Ge. [Extraction of 10-Deacetyl Baccatin by Supercritical CO2 from Taxus yunnanensis Branches and Leaves]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Apr; 38(4):827-30. doi: . [PMID: 26672353]
  • Bin Liu, Xiaoli Gou, Xupeng Bai, Xiangyu Hou, Dongshun Li, Guoping Zhong, Jing Jin, Min Huang. Simultaneous determination of seven taxoids in rat plasma by UPLC-MS/MS and pharmacokinetic study after oral administration of Taxus yunnanensis extracts. Journal of pharmaceutical and biomedical analysis. 2015 Mar; 107(?):346-54. doi: 10.1016/j.jpba.2015.01.001. [PMID: 25645339]
  • Zhang-Hua Sun, Yu Chen, Yan-Qiong Guo, Jie Qiu, Cui-Ge Zhu, Jing Jin, Gui-Hua Tang, Xian-Zhang Bu, Sheng Yin. Isolation and cytotoxicity evaluation of taxanes from the barks of Taxus wallichiana var. mairei. Bioorganic & medicinal chemistry letters. 2015 Mar; 25(6):1240-3. doi: 10.1016/j.bmcl.2015.01.056. [PMID: 25682561]
  • Yongchao Li, Jing Yang, Xiuren Zhou, Wenen Zhao, Zaiyou Jian. Isolation and identification of a 10-deacetyl baccatin-III-producing endophyte from Taxus wallichiana. Applied biochemistry and biotechnology. 2015 Feb; 175(4):2224-31. doi: 10.1007/s12010-014-1422-0. [PMID: 25475888]
  • Fei Han, Lin-Zhi Kang, Xian-Lu Zeng, Zhi-Wei Ye, Li-Qiong Guo, Jun-Fang Lin. Bioproduction of baccatin III, an advanced precursor of paclitaxol, with transgenic Flammulina velutipes expressing the 10-deacetylbaccatin III-10-O-acetyl transferase gene. Journal of the science of food and agriculture. 2014 Sep; 94(12):2376-83. doi: 10.1002/jsfa.6562. [PMID: 24403190]
  • S Li, P Zhang, M Zhang, C Fu, L Yu. Functional analysis of a WRKY transcription factor involved in transcriptional activation of the DBAT gene in Taxus chinensis. Plant biology (Stuttgart, Germany). 2013 Jan; 15(1):19-26. doi: 10.1111/j.1438-8677.2012.00611.x. [PMID: 22686366]
  • Masoumeh Safari, Faezeh Ghanati, Abazar Hajnoruzi, Ayatollah Rezaei, Parviz Abdolmaleki, Manigeh Mokhtari-Dizaji. Maintenance of membrane integrity and increase of taxanes production in hazel (Corylus avellana L.) cells induced by low-intensity ultrasound. Biotechnology letters. 2012 Jun; 34(6):1137-41. doi: 10.1007/s10529-012-0865-z. [PMID: 22315099]
  • T Grobosch, B Schwarze, D Stoecklein, T Binscheck. Fatal poisoning with Taxus baccata: quantification of paclitaxel (taxol A), 10-deacetyltaxol, baccatin III, 10-deacetylbaccatin III, cephalomannine (taxol B), and 3,5-dimethoxyphenol in body fluids by liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2012 Jan; 36(1):36-43. doi: 10.1093/jat/bkr012. [PMID: 22290751]
  • M Onrubia, E Moyano, M Bonfill, J Palazón, A Goossens, R M Cusidó. The relationship between TXS, DBAT, BAPT and DBTNBT gene expression and taxane production during the development of Taxus baccata plantlets. Plant science : an international journal of experimental plant biology. 2011 Sep; 181(3):282-7. doi: 10.1016/j.plantsci.2011.06.006. [PMID: 21763539]
  • Xiaoxian Li, Yaokang Xiong, Chenhuan Yu, Chunchun Zhang. [High performance liquid chromatographic fingerprints method for the analysis of chloroform extracts of Taxus wallichiana]. Se pu = Chinese journal of chromatography. 2010 Nov; 28(11):1067-70. doi: . [PMID: 21381424]
  • Katarzyna Syklowska-Baranek, Agnieszka Pietrosiuk, Anna Kokoszka, Miroslawa Furmanowa. Enhancement of taxane production in hairy root culture of Taxus x media var. Hicksii. Journal of plant physiology. 2009 Nov; 166(17):1950-4. doi: 10.1016/j.jplph.2009.05.001. [PMID: 19573947]
  • Rui Sun, Kusng Fu, Yujie Fu, Yuangang Zu, Ying Wang, Meng Luo, Shuangming Li, Hao Luo, Zhengnan Li. Preparative separation and enrichment of four taxoids from Taxus chinensis needles extracts by macroporous resin column chromatography. Journal of separation science. 2009 May; 32(9):1284-93. doi: 10.1002/jssc.200800689. [PMID: 19360728]
  • Yujie Fu, Yuangang Zu, Shuangming Li, Rui Sun, Thomas Efferth, Wei Liu, Shougang Jiang, Hao Luo, Ying Wang. Separation of 7-xylosyl-10-deacetyl paclitaxel and 10-deacetylbaccatin III from the remainder extracts free of paclitaxel using macroporous resins. Journal of chromatography. A. 2008 Jan; 1177(1):77-86. doi: 10.1016/j.chroma.2007.11.020. [PMID: 18054030]
  • Laura Ottaggio, Federica Bestoso, Andrea Armirotti, Alessandro Balbi, Gianluca Damonte, Mauro Mazzei, Monica Sancandi, Mariangela Miele. Taxanes from Shells and Leaves of Corylus avellana. Journal of natural products. 2008 Jan; 71(1):58-60. doi: 10.1021/np0704046. [PMID: 18163585]
  • Jianhua Li, Jungui Dai, Xiaoguang Chen, Ping Zhu. Microbial transformation of cephalomannine by Luteibacter sp. Journal of natural products. 2007 Dec; 70(12):1846-9. doi: 10.1021/np0701531. [PMID: 18001087]
  • Katerina Georgopoulou, Despina Smirlis, Sylvia Bisti, Evangelia Xingi, Leandros Skaltsounis, Ketty Soteriadou. In vitro activity of 10-deacetylbaccatin III against Leishmania donovani promastigotes and intracellular amastigotes. Planta medica. 2007 Aug; 73(10):1081-8. doi: 10.1055/s-2007-981579. [PMID: 17691059]
  • Binhui Guo, Guoyin Kai, Yifu Gong, Hongbin Jin, Yechun Wang, Zhiqi Miao, Xiaofen Sun, Kexuan Tang. Molecular cloning and heterologous expression of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus x media. Molecular biology reports. 2007 Jun; 34(2):89-95. doi: 10.1007/s11033-006-9018-6. [PMID: 17094009]
  • Yuangang Zu, Yujie Fu, Shuangming Li, Rui Sun, Qingyong Li, Günter Schwarz. Rapid separation of four main taxoids in Taxus species by a combined LLP-SPE-HPLC (PAD) procedure. Journal of separation science. 2006 Jun; 29(9):1237-44. doi: 10.1002/jssc.200500483. [PMID: 16833081]
  • Mian-Bin Wu, Shu-Zhen Ma. [The extraction and separation of an active and available component from Taxus mairei]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2006 Apr; 29(4):329-31. doi: . [PMID: 16913484]
  • Ya-Ching Shen, Kuen-Ching Cheng, Yun-Chi Lin, Yuan-Bin Cheng, Ashraf Taha Khalil, Jih-Hwa Guh, Ching-Te Chien, Che-Ming Teng, Yao-To Chang. Three new taxane diterpenoids from Taxus sumatrana. Journal of natural products. 2005 Jan; 68(1):90-3. doi: 10.1021/np040132w. [PMID: 15679325]
  • Guy Parc, Aurélie Canaguier, Pierre Landré, Reynald Hocquemiller, Dominique Chriqui, Michèle Meyer. Production of taxoids with biological activity by plants and callus culture from selected Taxus genotypes. Phytochemistry. 2002 Apr; 59(7):725-30. doi: 10.1016/s0031-9422(02)00043-2. [PMID: 11909629]
  • G Theodoridis, W Haasnoot, G Cazemier, R Schilt, M Jaziri, B Diallo, I N Papadoyannis, G J de Jong. Immunoaffinity chromatography for the sample pretreatment of Taxus plant and cell extracts prior to analysis of taxanes by high-performance liquid chromatography. Journal of chromatography. A. 2002 Mar; 948(1-2):177-85. doi: 10.1016/s0021-9673(01)01456-x. [PMID: 12831195]
  • T Mroczek, K Glowniak. Solid-phase extraction and simplified high-performance liquid chromatographic determination of 10-deacetylbaccatin III and related taxoids in yew species. Journal of pharmaceutical and biomedical analysis. 2001 Aug; 26(1):89-102. doi: 10.1016/s0731-7085(01)00353-3. [PMID: 11451646]
  • M L Hajnos, A M Zobel, K Głowniak. The influence of ultraviolet radiation on the content of pharmacologically active taxoids in yew tissues. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2001 Mar; 8(2):139-43. doi: 10.1078/0944-7113-00010. [PMID: 11315757]
  • S H Sheikh, B A Abela, A Mulchandani. Development of a fluorescence immunoassay for measurement of paclitaxel in human plasma. Analytical biochemistry. 2000 Jul; 283(1):33-8. doi: 10.1006/abio.2000.4630. [PMID: 10929805]
  • K Walker, R Croteau. Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Proceedings of the National Academy of Sciences of the United States of America. 2000 Jan; 97(2):583-7. doi: 10.1073/pnas.97.2.583. [PMID: 10639122]
  • K Glowniak, T Mroczek, A M Zobel. Seasonal changes in the concentrations of four taxoids in Taxus baccata L. during the autumn-spring period. Phytomedicine : international journal of phytotherapy and phytopharmacology. 1999 May; 6(2):135-40. doi: 10.1016/s0944-7113(99)80049-x. [PMID: 10374254]
  • K Walker, R E Ketchum, M Hezari, D Gatfield, M Goleniowski, A Barthol, R Croteau. Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis. Archives of biochemistry and biophysics. 1999 Apr; 364(2):273-9. doi: 10.1006/abbi.1999.1125. [PMID: 10190984]
  • X Cao, Y Tian, T Y Zhang, Y Ito. Separation and purification of 10-deacetylbaccatin III by high-speed counter-current chromatography. Journal of chromatography. A. 1998 Jul; 813(2):397-401. doi: 10.1016/s0021-9673(98)00360-4. [PMID: 9700932]
  • R Zocher, W Weckwerth, C Hacker, B Kammer, T Hornbogen, D Ewald. Biosynthesis of taxol: enzymatic acetylation of 10-deacetylbaccatin-III to baccatin-III in crude extracts from roots of Taxus baccata. Biochemical and biophysical research communications. 1996 Dec; 229(1):16-20. doi: 10.1006/bbrc.1996.1751. [PMID: 8954077]
  • F Kirikae, T Kirikae, N Qureshi, K Takayama, D C Morrison, M Nakano. CD14 is not involved in Rhodobacter sphaeroides diphosphoryl lipid A inhibition of tumor necrosis factor alpha and nitric oxide induction by taxol in murine macrophages. Infection and immunity. 1995 Feb; 63(2):486-97. doi: 10.1128/iai.63.2.486-497.1995. [PMID: 7529746]
  • A Concetti, E Ripani, L Barboni, E Torregiani, E Bombardelli, P Gariboldi, F M Venanzi. Immunorecognition of ring skeleton of taxanes by chicken egg yolk antibodies. Biological chemistry Hoppe-Seyler. 1994 Jun; 375(6):419-23. doi: 10.1515/bchm3.1994.375.6.419. [PMID: 7980875]
  • Y Guo, M Jaziri, B Diallo, R Vanhaelen-Fastre, A Zhiri, M Vanhaelen, J Homès, E Bombardelli. Immunological detection and quantitation of 10-deacetylbaccatin III in Taxus sp. plant and tissue cultures. Biological chemistry Hoppe-Seyler. 1994 Apr; 375(4):281-7. doi: 10.1515/bchm3.1994.375.4.281. [PMID: 8060537]
  • P G Grothaus, T J Raybould, G S Bignami, C B Lazo, J B Byrnes. An enzyme immunoassay for the determination of taxol and taxanes in Taxus sp. tissues and human plasma. Journal of immunological methods. 1993 Jan; 158(1):5-15. doi: 10.1016/0022-1759(93)90253-4. [PMID: 8094087]
  • D G Kingston, D R Hawkins, L Ovington. New taxanes from Taxus brevifolia. Journal of natural products. 1982 Jul; 45(4):466-70. doi: 10.1021/np50022a019. [PMID: 7130988]