taxa-4,11-diene (BioDeep_00000008942)
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C20H32 (272.2504)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(otcml) 10.16%
分子结构信息
SMILES: CC1=C2CCC3(CCC=C(C3CC(C2(C)C)CC1)C)C
InChI: InChI=1S/C20H32/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h7,16,18H,6,8-13H2,1-5H3/t16-,18+,20-/m0/s1
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:30037
- KEGG: C11894
- PubChem: 443484
- PubChem: 22239694
- Metlin: METLIN41256
- ChEMBL: CHEMBL4467915
- LipidMAPS: LMPR0104390002
- MetaCyc: TAXA-411-DIENE
- KNApSAcK: C00000900
- CAS: 163594-75-0
- PMhub: MS000022663
- PubChem: 14056
- 3DMET: B04369
- NIKKAJI: J651.843E
- KNApSAcK: 30037
分类词条
相关代谢途径
Reactome(0)
代谢反应
4 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(2)
- taxol biosynthesis:
acetyl-CoA + taxa-4(20),11-dien-5α-ol ⟶ coenzyme A + taxa-4(20),11-dien-5-α-yl acetate
- taxadiene biosynthesis (engineered):
IPP ⟶ DMAPP
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(2)
- 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
- taxadiene biosynthesis (engineered):
GGPP ⟶ diphosphate + taxa-4,11-diene
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 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
- Zihan Zhang, Longhao Huang, Zhi-Jun Zhang, Jian-He Xu, Hui-Lei Yu. Rational Design of Taxadiene Hydroxylase by Ancestral Enzyme Construction and the Elucidation of Key Amino Acids.
Biochemistry.
2023 Oct; ?(?):. doi:
10.1021/acs.biochem.3c00411
. [PMID: 37902563] - Ricardo De La Peña, Elizabeth S Sattely. Rerouting plant terpene biosynthesis enables momilactone pathway elucidation.
Nature chemical biology.
2021 02; 17(2):205-212. doi:
10.1038/s41589-020-00669-3
. [PMID: 33106662] - Jianhua Li, Ishmael Mutanda, Kaibo Wang, Lei Yang, Jiawei Wang, Yong Wang. Chloroplastic metabolic engineering coupled with isoprenoid pool enhancement for committed taxanes biosynthesis in Nicotiana benthamiana.
Nature communications.
2019 10; 10(1):4850. doi:
10.1038/s41467-019-12879-y
. [PMID: 31649252] - Tamar Ansbacher, Yehoshua Freud, Dan Thomas Major. Slow-Starter Enzymes: Role of Active-Site Architecture in the Catalytic Control of the Biosynthesis of Taxadiene by Taxadiene Synthase.
Biochemistry.
2018 07; 57(26):3773-3779. doi:
10.1021/acs.biochem.8b00452
. [PMID: 29791145] - Laxmi Sagwan-Barkdoll, Aldwin M Anterola. Taxadiene-5α-ol is a minor product of CYP725A4 when expressed in Escherichia coli.
Biotechnology and applied biochemistry.
2018 May; 65(3):294-305. doi:
10.1002/bab.1606
. [PMID: 28876471] - John Edward Rouck, Bradley Walters Biggs, Amogh Kambalyal, William R Arnold, Marjan De Mey, Parayil Kumaran Ajikumar, Aditi Das. Heterologous expression and characterization of plant Taxadiene-5α-Hydroxylase (CYP725A4) in Escherichia coli.
Protein expression and purification.
2017 04; 132(?):60-67. doi:
10.1016/j.pep.2017.01.008
. [PMID: 28109855] - Guangkai Bian, Yujie Yuan, Hui Tao, Xiaofei Shi, Xiaofang Zhong, Yichao Han, Shuai Fu, Chengxiang Fang, Zixin Deng, Tiangang Liu. Production of taxadiene by engineering of mevalonate pathway in Escherichia coli and endophytic fungus Alternaria alternata TPF6.
Biotechnology journal.
2017 Apr; 12(4):. doi:
10.1002/biot.201600697
. [PMID: 28217906] - Bradley Walters Biggs, John Edward Rouck, Amogh Kambalyal, William Arnold, Chin Giaw Lim, Marjan De Mey, Mark O'Neil-Johnson, Courtney M Starks, Aditi Das, Parayil Kumaran Ajikumar. Orthogonal Assays Clarify the Oxidative Biochemistry of Taxol P450 CYP725A4.
ACS chemical biology.
2016 05; 11(5):1445-51. doi:
10.1021/acschembio.5b00968
. [PMID: 26930136] - Linfeng You, Haixing Yang, Junfang Lin, Zhiwei Ye, Liqiong Guo, Yanhua Xin. [Combinational expression of geranylgeranyl diphosphate synthase and taxadiene synthase in Coprinopsis cinerea].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2015 Mar; 31(3):375-83. doi:
. [PMID: 26204758]
- Sameh Soliman, Yi Tang. Natural and engineered production of taxadiene with taxadiene synthase.
Biotechnology and bioengineering.
2015 Feb; 112(2):229-35. doi:
10.1002/bit.25468
. [PMID: 25257933] - Meiya Li, Fusheng Jiang, Xiangli Yu, Zhiqi Miao. Engineering isoprenoid biosynthesis in Artemisia annua L. for the production of taxadiene: a key intermediate of taxol.
BioMed research international.
2015; 2015(?):504932. doi:
10.1155/2015/504932
. [PMID: 25705665] - Md Mohidul Hasan, Hyun-Soon Kim, Jae-Heung Jeon, Sung Hong Kim, BoKyung Moon, Jai-Young Song, Sang Hee Shim, Kwang-Hyun Baek. Metabolic engineering of Nicotiana benthamiana for the increased production of taxadiene.
Plant cell reports.
2014 Jun; 33(6):895-904. doi:
10.1007/s00299-014-1568-9
. [PMID: 24463610] - Mijeong Cha, Sang Hee Shim, Sung Hong Kim, Ok Tae Kim, Se-Weon Lee, Suk-Yoon Kwon, Kwang-Hyun Baek. Production of taxadiene from cultured ginseng roots transformed with taxadiene synthase gene.
BMB reports.
2012 Oct; 45(10):589-94. doi:
10.5483/bmbrep.2012.45.10.085
. [PMID: 23101514] - Aldwin Anterola, Erin Shanle, Pierre-François Perroud, Ralph Quatrano. Production of taxa-4(5),11(12)-diene by transgenic Physcomitrella patens.
Transgenic research.
2009 Aug; 18(4):655-60. doi:
10.1007/s11248-009-9252-5
. [PMID: 19241134] - Denis Rontein, Sandrine Onillon, Gaëtan Herbette, Agnes Lesot, Danièle Werck-Reichhart, Christophe Sallaud, Alain Tissier. CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane.
The Journal of biological chemistry.
2008 Mar; 283(10):6067-75. doi:
10.1074/jbc.m708950200
. [PMID: 18167342] - Katalin Kovacs, Lina Zhang, Robert S T Linforth, Benjamin Whittaker, Christopher J Hayes, Rupert G Fray. Redirection of carotenoid metabolism for the efficient production of taxadiene [taxa-4(5),11(12)-diene] in transgenic tomato fruit.
Transgenic research.
2007 Feb; 16(1):121-6. doi:
10.1007/s11248-006-9039-x
. [PMID: 17106766] - Oscar Besumbes, Susanna Sauret-Güeto, Michael A Phillips, Santiago Imperial, Manuel Rodríguez-Concepción, Albert Boronat. Metabolic engineering of isoprenoid biosynthesis in Arabidopsis for the production of taxadiene, the first committed precursor of Taxol.
Biotechnology and bioengineering.
2004 Oct; 88(2):168-75. doi:
10.1002/bit.20237
. [PMID: 15449291] - M Hezari, N G Lewis, R Croteau. Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis.
Archives of biochemistry and biophysics.
1995 Oct; 322(2):437-44. doi:
10.1006/abbi.1995.1486
. [PMID: 7574719]