(S)-2,3-epoxysqualene (BioDeep_00001869013)
Main id: BioDeep_00000004555
代谢物信息卡片
(S)-2,3-epoxysqualene
化学式: C30H50O (426.386145)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CC[C@H]1C(C)(C)O1)/C)/C)C
InChI: InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1
描述信息
A 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted into lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.
同义名列表
1 个代谢物同义名
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:15441
- KEGG: C01054
- PubChem: 5459811
- CAS: 54910-48-4
- CAS: 9029-62-3
- MetaboLights: MTBLC15441
- PubChem: 4295
- LipidMAPS: LMPR0106010010
- KNApSAcK: C00007282
- PDB-CCD: 2TX
- 3DMET: B01371
- NIKKAJI: J39.259F
- RefMet: (S)-2,3-Epoxysqualene
分类词条
相关代谢途径
BioCyc(13)
- plant sterol biosynthesis
- superpathway of sterol biosynthesis
- ginsenosides biosynthesis
- superpathway of ergosterol biosynthesis I
- superpathway of ergosterol biosynthesis
- diploterol and cycloartenol biosynthesis
- cholesterol biosynthesis I
- cholesterol biosynthesis III (via desmosterol)
- superpathway of cholesterol biosynthesis
- cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
- 7-dehydroporiferasterol biosynthesis
- marneral biosynthesis
- pentacyclic triterpene biosynthesis
PlantCyc(4)
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
- 76314 - Caulerpa prolifera: 10.1016/0031-9422(82)83189-0
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- Xiao-Bo Li, Chun-Li Huang, Ying Zhang, Jing-Yang Ding, Gui-Sheng Xiang, Guang-Hui Zhang, Sheng-Chao Yang, Bing Hao. Promiscuous Oxidosqualene Cyclases from Neoalsomitra integrifoliola Catalyzing the Formation of Tetracyclic, Pentacyclic, and Heterocyclic Triterpenes.
Organic letters.
2024 Apr; 26(15):3119-3123. doi:
10.1021/acs.orglett.4c00730. [PMID: 38588021] - Bhawana Mishra, Shilpi Bansal, Sandhya Tripathi, Smrati Mishra, Ritesh K Yadav, Neelam S Sangwan. Differential regulation of key triterpene synthase gene under abiotic stress in Withania somnifera L. Dunal and its co-relation to sterols and withanolides.
Plant physiology and biochemistry : PPB.
2024 Mar; 208(?):108419. doi:
10.1016/j.plaphy.2024.108419. [PMID: 38377888] - Shuang-Yan Zhang, Yu-Qing Peng, Gui-Sheng Xiang, Wan-Ling Song, Lei Feng, Xin-Yue Jiang, Xue-Jiao Li, Si-Mei He, Sheng-Chao Yang, Yan Zhao, Guang-Hui Zhang. Functional characterization of genes related to triterpene and flavonoid biosynthesis in Cyclocarya paliurus.
Planta.
2024 Jan; 259(2):50. doi:
10.1007/s00425-023-04282-1. [PMID: 38285114] - Yanan Huang, Helu Liu, Yang Zhou, Zaiqing Lu, Yujin Pu, Haibin Zhang. Cloning and functional characterization of the oxidative squalene cyclase gene in the deep-sea holothurian Chiridota sp.
Gene.
2023 Nov; ?(?):147971. doi:
10.1016/j.gene.2023.147971. [PMID: 37949417] - Jinling Li, Shuai Wang, Yinan Miao, Ya Wan, Chun Li, Ying Wang. Mining and modification of Oryza sativa-derived squalene epoxidase for improved β-amyrin production in Saccharomyces cerevisiae.
Journal of biotechnology.
2023 Aug; 375(?):1-11. doi:
10.1016/j.jbiotec.2023.08.004. [PMID: 37597655] - Hidayat Hussain, Jianbo Xiao, Akbar Ali, Ivan R Green, Bernhard Westermann. Unusually cyclized triterpenoids: occurrence, biosynthesis and chemical synthesis.
Natural product reports.
2023 Feb; 40(2):412-451. doi:
10.1039/d2np00033d. [PMID: 36458822] - Yibo Wang, Baojie Wang, Furong Xu, Xiaohui Ma. Molecular Cloning and Functional Characterization of Oxidosqualene Cyclases from Panax vietnamensis.
Chemistry & biodiversity.
2023 Feb; 20(2):e202200874. doi:
10.1002/cbdv.202200874. [PMID: 36635849] - Kuan Chen, Meng Zhang, Lulu Xu, Yang Yi, Linlin Wang, Haotian Wang, Zilong Wang, Jiangtao Xing, Pi Li, Xiaohui Zhang, Xiaomeng Shi, Min Ye, Anne Osbourn, Xue Qiao. Identification of oxidosqualene cyclases associated with saponin biosynthesis from Astragalus membranaceus reveals a conserved motif important for catalytic function.
Journal of advanced research.
2023 01; 43(?):247-257. doi:
10.1016/j.jare.2022.03.014. [PMID: 36585112] - Pornpatsorn Lertphadungkit, Xue Qiao, Min Ye, Somnuk Bunsupa. Characterization of oxidosqualene cyclases from Trichosanthes cucumerina L. reveals key amino acids responsible for substrate specificity of isomultiflorenol synthase.
Planta.
2022 Aug; 256(3):58. doi:
10.1007/s00425-022-03972-6. [PMID: 35980476] - Liufang Huang, Yonger Hu, Ruoshi Huang, Jiabo Chen, Xiande Zhang, Jingyang Yue, Laibao Feng, Yaru She, Aijia Ji, Ying Zheng, Zhongqiu Liu, Rongrong Zhang, Lixin Duan. Oxidosqualene Cyclases Involved in the Biosynthesis of Diverse Triterpenes in Camellia sasanqua.
Journal of agricultural and food chemistry.
2022 Jul; 70(26):8075-8084. doi:
10.1021/acs.jafc.2c03011. [PMID: 35729682] - Yusuke Otani, Takashi Maoka, Shigeko Kawai-Noma, Kyoichi Saito, Daisuke Umeno. A novel carotenoid biosynthetic route via oxidosqualene.
Biochemical and biophysical research communications.
2022 04; 599(?):75-80. doi:
10.1016/j.bbrc.2022.01.105. [PMID: 35176628] - Cuiyu Chen, Yaru Pang, Quanbing Chen, Chun Li, Bo Lü. [Oxidosqualene cyclases in triterpenoids biosynthesis: a review].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2022 Feb; 38(2):443-459. doi:
10.13345/j.cjb.210169. [PMID: 35234375] - Han Suk Choi, Jung Yeon Han, Yong Eui Choi. Identification of triterpenes and functional characterization of oxidosqualene cyclases involved in triterpene biosynthesis in lettuce (Lactuca sativa).
Plant science : an international journal of experimental plant biology.
2020 Dec; 301(?):110656. doi:
10.1016/j.plantsci.2020.110656. [PMID: 33218626] - Jian Wang, Hui-Xin Lin, Huan Zhao, Juan Guo, Ping Su, Jian Yang, Xiao-Yi Wu, Lu-Qi Huang, Wei Gao. Molecular cloning and functional characterization of multiple ApOSCs from Andrographis paniculata.
Chinese journal of natural medicines.
2020 Sep; 18(9):659-665. doi:
10.1016/s1875-5364(20)60004-8. [PMID: 32928509] - Rong Tian, Wei Gu, Yuchen Gu, Chao Geng, Fei Xu, Qinan Wu, Jianguo Chao, Wenda Xue, Chen Zhou, Fan Wang. Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale.
Scientific reports.
2019 12; 9(1):18139. doi:
10.1038/s41598-019-54629-6. [PMID: 31792343] - Hye-Jeong Jo, Jung Yeon Han, Hwan-Su Hwang, Yong Eui Choi. β-Amyrin synthase (EsBAS) and β-amyrin 28-oxidase (CYP716A244) in oleanane-type triterpene saponin biosynthesis in Eleutherococcus senticosus.
Phytochemistry.
2017 Mar; 135(?):53-63. doi:
10.1016/j.phytochem.2016.12.011. [PMID: 28012567] - Christelle M Andre, Sylvain Legay, Amélie Deleruelle, Niels Nieuwenhuizen, Matthew Punter, Cyril Brendolise, Janine M Cooney, Marc Lateur, Jean-François Hausman, Yvan Larondelle, William A Laing. Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids.
The New phytologist.
2016 09; 211(4):1279-94. doi:
10.1111/nph.13996. [PMID: 27214242] - Elisabet Gas-Pascual, Biljana Simonovik, Hubert Schaller, Thomas J Bach. Inhibition of Cycloartenol Synthase (CAS) Function in Tobacco BY-2 Cells.
Lipids.
2015 Aug; 50(8):761-72. doi:
10.1007/s11745-015-4036-6. [PMID: 26033687] - Elisabet Gas-Pascual, Anne Berna, Thomas J Bach, Hubert Schaller. Plant oxidosqualene metabolism: cycloartenol synthase-dependent sterol biosynthesis in Nicotiana benthamiana.
PloS one.
2014; 9(10):e109156. doi:
10.1371/journal.pone.0109156. [PMID: 25343375] - Ryousuke Ito, Ippei Hashimoto, Yukari Masukawa, Tsutomu Hoshino. Effect of cation-π interactions and steric bulk on the catalytic action of oxidosqualene cyclase: a case study of Phe728 of β-amyrin synthase from Euphorbia tirucalli L.
Chemistry (Weinheim an der Bergstrasse, Germany).
2013 Dec; 19(50):17150-8. doi:
10.1002/chem.201301917. [PMID: 24203491] - Ikuro Abe. [Engineering of squalene cyclizing enzymes].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2008 Aug; 128(8):1109-18. doi:
10.1248/yakushi.128.1109. [PMID: 18670176] - Masashi Suzuki, Ting Xiang, Kiyoshi Ohyama, Hikaru Seki, Kazuki Saito, Toshiya Muranaka, Hiroaki Hayashi, Yuji Katsube, Tetsuo Kushiro, Masaaki Shibuya, Yutaka Ebizuka. Lanosterol synthase in dicotyledonous plants.
Plant & cell physiology.
2006 May; 47(5):565-71. doi:
10.1093/pcp/pcj031. [PMID: 16531458] - O H Morand, J D Aebi, H Dehmlow, Y H Ji, N Gains, H Lengsfeld, J Himber. Ro 48-8.071, a new 2,3-oxidosqualene:lanosterol cyclase inhibitor lowering plasma cholesterol in hamsters, squirrel monkeys, and minipigs: comparison to simvastatin.
Journal of lipid research.
1997 Feb; 38(2):373-90. doi:
10.1016/s0022-2275(20)37449-6. [PMID: 9162756] - S D Atkin, B Morgan, K H Baggaley, J Green. The isolation of 2,3-oxidosqualene from the liver of rats treated with 1-dodecylimidazole, a novel hypocholesterolaemic agent.
The Biochemical journal.
1972 Nov; 130(1):153-7. doi:
10.1042/bj1300153. [PMID: 4655417]