10-Deacetyltaxol 7-Xyloside (BioDeep_00000230703)

 

Secondary id: BioDeep_00000231286, BioDeep_00000402958, BioDeep_00000614675

PANOMIX_OTCML-2023


代谢物信息卡片


Benzenepropanoic acid, b-(benzoylamino)-a-hydroxy-,(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-(b-D-xylopyranosyloxy)-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (aR,bS)-

化学式: C50H57NO17 (943.3626311999999)
中文名称: 7-木糖甙-10-脱乙酰基紫杉醇, 10-脱乙酰基-7-木糖基紫杉醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.7%

分子结构信息

SMILES: CC(O[C@]([C@@]1([H])C[C@@H]2O[C@@](OC[C@@H](O)[C@@H]3O)([H])[C@@H]3O)(CO1)[C@]([C@@H]([C@]4(C(C)(C)C5=C(C)[C@@H](OC([C@H](O)[C@H](C6=CC=CC=C6)NC(C7=CC=CC=C7)=O)=O)C4)O)OC(C8=CC=CC=C8)=O)([H])[C@@]2(C([C@@H]5O)=O)C)=O
InChI: InChI=1S/C50H57NO17/c1-25-31(65-45(61)38(56)35(27-15-9-6-10-16-27)51-43(59)28-17-11-7-12-18-28)22-50(62)42(67-44(60)29-19-13-8-14-20-29)40-48(5,41(58)37(55)34(25)47(50,3)4)32(21-33-49(40,24-64-33)68-26(2)52)66-46-39(57)36(54)30(53)23-63-46/h6-20,30-33,35-40,42,46,53-57,62H,21-24H2,1-5H3,(H,51,59)/t30-,31+,32+,33-,35+,36+,37-,38-,39-,40+,42+,46+,48-,49+,50-/m1/s1

描述信息

10-Deacetyl-7-xylosyl paclitaxel is a Paclitaxel (a microtubule stabilizing agent; enhances tubulin polymerization) derivative with improved pharmacological features. IC50 value: Target: Microtubule inhibitor 10-Deacetyl-7-xylosyl paclitaxel induced mitotic cell cycle arrest and apoptosis as measured by flow cytometry, DNA laddering, and transmission electron microscopy. Pro-apoptotic Bax and Bad protein expression was up-regulated and anti-apoptotic Bcl-2 and Bcl-XL expression down-regulated, which lead to a disturbance of the mitochondrial membrane permeability and to the activation of caspase-9. In turn, caspase-9 activated downstream caspases-3 and -6, but not caspase-8. Bid was also activated by caspase-3. Reversely, treatment with a caspase-10-specific inhibitor could not protect PC-3 cells from 7-xylosyl-10-deacetyl-paclitaxel-triggered apoptosis. Moreover, 7-xylosyl-10-deacetylpaclitaxel had no effect on the expression of CD95 and NF-kappaB proteins, indicating that apoptosis was induced through the mitochondrial-dependent pathway in PC-3 cells.
10-Deacetyl-7-xylosyl paclitaxel is a Paclitaxel (a microtubule stabilizing agent; enhances tubulin polymerization) derivative with improved pharmacological features. IC50 value: Target: Microtubule inhibitor 10-Deacetyl-7-xylosyl paclitaxel induced mitotic cell cycle arrest and apoptosis as measured by flow cytometry, DNA laddering, and transmission electron microscopy. Pro-apoptotic Bax and Bad protein expression was up-regulated and anti-apoptotic Bcl-2 and Bcl-XL expression down-regulated, which lead to a disturbance of the mitochondrial membrane permeability and to the activation of caspase-9. In turn, caspase-9 activated downstream caspases-3 and -6, but not caspase-8. Bid was also activated by caspase-3. Reversely, treatment with a caspase-10-specific inhibitor could not protect PC-3 cells from 7-xylosyl-10-deacetyl-paclitaxel-triggered apoptosis. Moreover, 7-xylosyl-10-deacetylpaclitaxel had no effect on the expression of CD95 and NF-kappaB proteins, indicating that apoptosis was induced through the mitochondrial-dependent pathway in PC-3 cells.

同义名列表

11 个代谢物同义名

Benzenepropanoic acid, b-(benzoylamino)-a-hydroxy-,(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-(b-D-xylopyranosyloxy)-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (aR,bS)-; [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,12-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate; Benzenepropanoic acid, b-(benzoylamino)-a-hydroxy-,(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-(b-D-xylopyranosyloxy)-7,11-methano-1H-cyclo; 10-O-Deacetyl-7-O-(beta-xylosyl)paclitaxel; 10-Deacetylpaclitaxel 7-Xyloside; 10-Deacetyl-7-xylosyl Paclitaxel; 7-xylosyl-10-deacetyl taxol; 7-xylosyl-10-deacetyl-taxol; 10-Deacetyltaxol 7-Xyloside; 7-Xylosyl-10-deacetyltaxol; 10-Deacetyl-7-xylosyltaxol



数据库引用编号

4 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)

2 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

  • Tong-Yi Dou, Hong-Wei Luan, Guang-Bo Ge, Ming-Ming Dong, Han-Fa Zou, Yu-Qi He, Pan Cui, Jia-Yue Wang, Da-Cheng Hao, Shi-Lin Yang, Ling Yang. Functional and structural properties of a novel cellulosome-like multienzyme complex: efficient glycoside hydrolysis of water-insoluble 7-xylosyl-10-deacetylpaclitaxel. Scientific reports. 2015 Sep; 5(?):13768. doi: 10.1038/srep13768. [PMID: 26347949]
  • 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]
  • Shougang Jiang, Yuangang Zu, Zhuo Wang, Yu Zhang, Yuejie Fu. Involvement of mitochondrial permeability transition pore opening in 7-xylosyl-10-deacetylpaclitaxel-induced apoptosis. Planta medica. 2011 Jul; 77(10):1005-12. doi: 10.1055/s-0030-1270732. [PMID: 21294074]
  • Shougang Jiang, Yuangang Zu, Yu Zhang, Yujie Fu, Zhuo Wang, Jingtao Wang. Transport of a hydrophilic paclitaxel derivative, 7-xylosyl-10-deacetylpaclitaxel, by human intestinal epithelial Caco-2 cells. Planta medica. 2010 Oct; 76(14):1592-5. doi: 10.1055/s-0030-1249836. [PMID: 20414861]
  • Shou Gang Jiang, Yuan Gang Zu, Lin Zhang, Yu Jie Fu, Yu Zhang, Zhou Wang, Xin Hua, Jing Tao Wang. Determination of a hydrophilic paclitaxel derivative, 7-xylosyl-10-deacetylpaclitaxel in rat plasma by LC-MS/MS. Biomedical chromatography : BMC. 2009 May; 23(5):472-9. doi: 10.1002/bmc.1138. [PMID: 19016230]
  • Shougang Jiang, Yuangang Zu, Yuejie Fu, Yu Zhang, Thomas Efferth. Activation of the mitochondria-driven pathway of apoptosis in human PC-3 prostate cancer cells by a novel hydrophilic paclitaxel derivative, 7-xylosyl-10-deacetylpaclitaxel. International journal of oncology. 2008 Jul; 33(1):103-11. doi: 10.3892/ijo.33.1.103. [PMID: 18575755]