Taxol B (BioDeep_00000001931)

   

PANOMIX_OTCML-2023


代谢物信息卡片


Benzenepropanoic acid, alpha-hydroxy-beta-((2-methyl-1-oxo-2-butenyl)amino)-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(aR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-

化学式: C45H53NO14 (831.3465878)
中文名称: 三尖杉宁碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.19%

分子结构信息

SMILES: CC=C(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
InChI: InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1

描述信息

Taxol B is a natural product found in Corylus avellana, Taxus wallichiana, and other organisms with data available.
Cephalomannine is a diterpene taxane obtained from the bark and leaves of the yew tree (Taxus brevifolia) and can convert to taxol. (NCI)
Cephalomannine is a Paclitaxel (HY-B0015) alkaloidal analog and isolated from most Cephalotaxus species. Cephalomannine is an orally active anti-tumor agent and can be used as a chemotherapy agent for cancer research[1][2].
Cephalomannine is a Paclitaxel (HY-B0015) alkaloidal analog that can be isolated from most Cephalotaxus species. Cephalomannine is an orally active anti-tumor agent and can be used as a chemotherapy agent for cancer research[1][2][3][4].
Cephalomannine is a Paclitaxel (HY-B0015) alkaloidal analog and isolated from most Cephalotaxus species. Cephalomannine is an orally active anti-tumor agent and can be used as a chemotherapy agent for cancer research[1][2].

同义名列表

14 个代谢物同义名

Benzenepropanoic acid, alpha-hydroxy-beta-((2-methyl-1-oxo-2-butenyl)amino)-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(aR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-; BENZENEPROPANOIC ACID, .ALPHA.-HYDROXY-.BETA.-(((2E)-2-METHYL-1-OXO-2-BUTEN-1-YL)AMINO)-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-6,12B-BIS(ACETYLOXY)-12-(BENZOYLOXY)-2A,3,4,4A,5,6,9,10,11,12,12A,12B-DODECAHYDRO-4,11-DIHYDROXY-4A,8,13,13-TETRAMETHYL-5-OXO-7,11-METHANO-1H-CYCLODECA(3,4)BENZ(1,2-B)OXET-9-YL ESTER, (.ALPHA.R,.BETA.S)-; Benzenepropanoic acid, alpha-hydroxy-beta-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-; Benzenepropanoic acid, alpha-hydroxy-beta-(((2E)-2-methyl-1-oxo-2-butenyl)amino)-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (alphaR,betaS)-; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-4,11-dihydroxy-9-(((2R,3S)-2-hydroxy-3-((E)-2-methylbut-2-enamido)-3-phenylpropanoyl)oxy)-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate; [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl]benzoate; 4,10beta-bis(acetyloxy)-1,7beta-dihydroxy-13alpha-[[(2R,3S)-2-hydroxy-3-[[(2E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy]-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate; N-Debenzoyl-N-tigloylpaclitaxel (Cephalomannine); PACLITAXEL IMPURITY B [EP IMPURITY]; DBXFAPJCZABTDR-WBYYIXQISA-N; Taxol B (Cephalomannine); Cephalomannine; Taxol B; 7-epi-Cephalomannine



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)

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

  • 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]
  • Xin-Shuai Wang, Jia-Chun Sun, Rui-Na Yang, Jing Ren, Shuo Liang, Ming Sun, Ying-Fei Wang, She-Gan Gao. Determination of cephalomannine in rat plasma by gradient elution UPLC-MS/MS method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 963(?):70-4. doi: 10.1016/j.jchromb.2014.05.045. [PMID: 24929960]
  • Feng Gao, Dan Wang, Xing Huang. Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine. Fitoterapia. 2013 Oct; 90(?):79-84. doi: 10.1016/j.fitote.2013.07.011. [PMID: 23876369]
  • Shao-Shuai Yu, Qi-Wu Sun, Xiao-Ping Zhang, Sheng-Ni Tian, Pei-Lei Bo. [Content and distribution of active components in cultivated and wild Taxus chinensis var. mairei plants]. Ying yong sheng tai xue bao = The journal of applied ecology. 2012 Oct; 23(10):2641-7. doi: . [PMID: 23359921]
  • 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]
  • Zui Chang, Na Guo, Tong Liu, Zhiqiang Zhou, Yang Wang. [Distribution and variation of paclitaxel and cephalomannine contents in wild Taxus cuspidata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Feb; 36(3):294-8. doi: 10.4268/cjcmm20110314. [PMID: 21585029]
  • Siva A Vanapalli, Yixuan Li, Frieder Mugele, Michel H G Duits. On the origins of the universal dynamics of endogenous granules in mammalian cells. Molecular & cellular biomechanics : MCB. 2009 Dec; 6(4):191-201. doi: ". [PMID: 19899443]
  • 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]
  • Richard G Powell. Plant seeds as sources of potential industrial chemicals, pharmaceuticals, and pest control agents. Journal of natural products. 2009 Mar; 72(3):516-23. doi: 10.1021/np8006217. [PMID: 19209890]
  • Xuan Li, Isabel Barasoain, Ruth Matesanz, J Fernando Díaz, Wei-Shuo Fang. Synthesis and biological activities of high affinity taxane-based fluorescent probes. Bioorganic & medicinal chemistry letters. 2009 Feb; 19(3):751-4. doi: 10.1016/j.bmcl.2008.12.018. [PMID: 19128972]
  • Feng-jian Yang, Hai-he Pang, Xue-ke Zhang, Jia-yin Sun, Yuan-gang Zu. [Quantitative changes of anti-cancer active components in Taxus chinensis var. mairei branches and leaves]. Ying yong sheng tai xue bao = The journal of applied ecology. 2008 Apr; 19(4):911-4. doi: ". [PMID: 18593057]
  • 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]
  • 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]
  • 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 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]
  • D D Woo, A P Tabancay, C J Wang. Microtubule active taxanes inhibit polycystic kidney disease progression in cpk mice. Kidney international. 1997 May; 51(5):1613-8. doi: 10.1038/ki.1997.222. [PMID: 9150481]
  • K Glowniak, G Zgórka, A Józefczyk, M Furmanowa. Sample preparation for taxol and cephalomannine determination in various organs of Taxus sp. Journal of pharmaceutical and biomedical analysis. 1996 Jun; 14(8-10):1215-20. doi: 10.1016/s0731-7085(96)01728-1. [PMID: 8818036]
  • D Song, J L Au. Isocratic high-performance liquid chromatographic assay of taxol in biological fluids and tissues using automated column switching. Journal of chromatography. B, Biomedical applications. 1995 Jan; 663(2):337-44. doi: 10.1016/0378-4347(94)00456-f. [PMID: 7735481]
  • S H Hoke, R G Cooks, C J Chang, R C Kelly, S J Qualls, B Alvarado, M T McGuire, K M Snader. Determination of taxanes in Taxus brevifolia extracts by tandem mass spectrometry and high-performance liquid chromatography. Journal of natural products. 1994 Feb; 57(2):277-86. doi: 10.1021/np50104a013. [PMID: 7909835]
  • 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]
  • J G Leu, K S Jech, N C Wheeler, B X Chen, B F ERlanger. Immunoassay of taxol and taxol-like compounds in plant extracts. Life sciences. 1993; 53(12):PL183-7. doi: 10.1016/0024-3205(93)90128-p. [PMID: 8103185]
  • S H Hoke, J M Wood, R G Cooks, X H Li, C J Chang. Rapid screening for taxanes by tandem mass spectrometry. Analytical chemistry. 1992 Oct; 64(20):2313-5. doi: 10.1021/ac00044a002. [PMID: 1361307]
  • N C Wheeler, K Jech, S Masters, S W Brobst, A B Alvarado, A J Hoover, K M Snader. Effects of genetic, epigenetic, and environmental factors on taxol content in Taxus brevifolia and related species. Journal of natural products. 1992 Apr; 55(4):432-40. doi: 10.1021/np50082a005. [PMID: 1355111]
  • C Rao, X Liu, P L Zhang, W M Chen, Q C Fang. [Application of high speed countercurrent chromatography for the isolation of natural products--preparative isolation of taxane-diterpenoids and diterpene alkaloids]. Yao xue xue bao = Acta pharmaceutica Sinica. 1991; 26(7):510-4. doi: ". [PMID: 1687187]