10-Deacetylbaccatin III (BioDeep_00000002134)

 

Secondary id: BioDeep_00000230418

natural product PANOMIX_OTCML-2023


代谢物信息卡片


7-epi-10-Deacetylbaccatin III

化学式: C29H36O10 (544.2308)
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) 17.05%

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。

亚细胞结构定位 关联基因列表
Cytoplasm 13 ABCB1, ANXA5, BCL2, EIF1, FGF2, GGPS1, HAP1, PDLIM4, PGP, RAF1, RB1, TUBB3, TUBB4B
Peripheral membrane protein 3 ANXA5, CAV1, PDLIM4
Endosome membrane 2 CD14, LY96
Endoplasmic reticulum membrane 3 BCL2, CAV1, TBXAS1
Cytoplasmic vesicle, autophagosome 1 HAP1
Nucleus 9 BCL2, EIF1, FGF2, HAP1, PDLIM4, RAF1, RB1, TUBB3, TUBB4B
autophagosome 1 HAP1
cytosol 8 ANXA5, BCL2, GGPS1, HAP1, RAF1, RB1, TBXAS1, TUBB4B
dendrite 2 HAP1, TUBB3
centrosome 1 HAP1
nucleoplasm 3 GGPS1, HAP1, RB1
Cell membrane 6 ABCB1, CAV1, CD14, CNTN2, RAF1, TNF
Cytoplasmic side 1 PDLIM4
lamellipodium 2 PDLIM4, TUBB3
Cell projection, axon 1 HAP1
Cell projection, growth cone 2 HAP1, TUBB3
Early endosome membrane 2 CAV1, PDLIM4
Multi-pass membrane protein 2 ABCB1, TBXAS1
Golgi apparatus membrane 1 CAV1
Synapse 2 CNTN2, PDLIM4
cell cortex 1 CAV1
cell surface 3 ABCB1, CNTN2, TNF
Golgi apparatus 3 CAV1, CD14, RAF1
Golgi membrane 1 CAV1
growth cone 2 HAP1, TUBB3
neuronal cell body 3 CNTN2, TNF, TUBB3
sarcolemma 1 ANXA5
synaptic vesicle 1 HAP1
Lysosome 1 HAP1
Presynapse 1 HAP1
endosome 1 CAV1
plasma membrane 7 ABCB1, CAV1, CD14, CNTN2, LY96, RAF1, TNF
Membrane 5 ABCB1, ANXA5, BCL2, CAV1, TBXAS1
apical plasma membrane 2 ABCB1, CAV1
axon 2 CNTN2, TUBB3
basolateral plasma membrane 1 CAV1
caveola 1 CAV1
extracellular exosome 6 ABCB1, ANXA5, CD14, DEFA3, TUBB3, TUBB4B
endoplasmic reticulum 4 BCL2, CAV1, HAP1, TBXAS1
extracellular space 4 CD14, DEFA3, FGF2, TNF
perinuclear region of cytoplasm 4 CAV1, GGPS1, HAP1, PDLIM4
adherens junction 1 PDLIM4
mitochondrion 3 BCL2, HAP1, RAF1
protein-containing complex 2 BCL2, CAV1
filopodium 1 TUBB3
Secreted 4 CD14, DEFA3, FGF2, LY96
extracellular region 7 ANXA5, CD14, DEFA3, FGF2, LY96, TNF, TUBB4B
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, RAF1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ANXA5, CD14, TNF
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 HAP1
dendritic spine 2 HAP1, PDLIM4
Z disc 2 GGPS1, PDLIM4
cytoplasmic vesicle 2 CAV1, HAP1
microtubule cytoskeleton 2 TUBB3, TUBB4B
nucleolus 1 HAP1
axon cytoplasm 1 HAP1
Early endosome 1 HAP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 CNTN2, PDLIM4
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 2 PDLIM4, TUBB3
Cytoplasm, perinuclear region 2 GGPS1, PDLIM4
Membrane raft 3 CAV1, CD14, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 4 HAP1, PDLIM4, TUBB3, TUBB4B
focal adhesion 2 ANXA5, CAV1
microtubule 2 TUBB3, TUBB4B
spindle 2 RB1, TUBB3
Cell projection, dendritic spine 2 HAP1, PDLIM4
PML body 1 RB1
collagen-containing extracellular matrix 1 ANXA5
nuclear speck 1 HAP1
Cell projection, filopodium 1 TUBB3
receptor complex 1 LY96
Cell projection, neuron projection 1 HAP1
Zymogen granule membrane 1 ANXA5
cilium 1 CAV1
chromatin 1 RB1
phagocytic cup 1 TNF
cell periphery 1 TUBB3
mitotic spindle 2 TUBB3, TUBB4B
cytoskeleton 3 HAP1, PDLIM4, TUBB4B
centriole 1 HAP1
Secreted, extracellular space 1 LY96
Golgi apparatus, trans-Golgi network 1 CAV1
chromosome, telomeric region 1 HAP1
Lipid-anchor, GPI-anchor 2 CD14, CNTN2
intercellular bridge 2 TUBB3, TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
Recycling endosome membrane 1 PDLIM4
Endomembrane system 1 PDLIM4
Lipid droplet 1 CAV1
Membrane, caveola 1 CAV1
axonemal microtubule 1 TUBB4B
filamentous actin 1 PDLIM4
axon initial segment 1 CNTN2
Cell projection, dendrite 1 HAP1
side of membrane 2 CD14, CNTN2
myelin sheath 2 BCL2, CNTN2
pseudopodium 1 RAF1
Cytoplasm, myofibril, sarcomere, Z line 1 GGPS1
stress fiber 1 PDLIM4
lipopolysaccharide receptor complex 2 CD14, LY96
secretory granule membrane 1 CD14
Golgi lumen 1 DEFA3
eukaryotic 43S preinitiation complex 1 EIF1
eukaryotic 48S preinitiation complex 1 EIF1
endocytic vesicle membrane 1 CAV1
node of Ranvier 1 CNTN2
azurophil granule lumen 2 DEFA3, TUBB4B
SWI/SNF complex 1 RB1
[Isoform 2]: Cytoplasm 1 PDLIM4
vesicle membrane 1 ANXA5
Synapse, synaptosome 1 PDLIM4
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cytoplasm, cytoskeleton 1 PDLIM4
acrosomal membrane 1 CAV1
ribosome 1 HAP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
inclusion body 1 HAP1
chromatin lock complex 1 RB1
Rb-E2F complex 1 RB1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 HAP1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
juxtaparanode region of axon 1 CNTN2
multi-eIF complex 1 EIF1
early endosome lumen 1 PDLIM4
recycling endosome lumen 1 PDLIM4
caveolar macromolecular signaling complex 1 CAV1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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