(S)-2,3-Epoxysqualene (BioDeep_00000004555)

 

Secondary id: BioDeep_00000598282, BioDeep_00001869013

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(3S)-2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaen-1-yl]oxirane

化学式: C30H50O (426.386145)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 1.54%

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

(S)-2,3-Epoxysqualene, also known as 2,3-oxidosqualene or (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, (S)-2,3-epoxysqualene is considered to be an isoprenoid lipid molecule. (S)-2,3-Epoxysqualene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of terpenoid. It is a substrate for squalene monooxygenase and lanosterol synthase.
(S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Squalene monooxygenase and Lanosterol synthase. [HMDB]. (S)-2,3-Epoxysqualene is found in many foods, some of which are new zealand spinach, lime, cassava, and cloves.

同义名列表

43 个代谢物同义名

(3S)-2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaen-1-yl]oxirane; (3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane; (S)-2,3-Epoxysqualene;(S)-2,3-epoxysqualene;(S)-Squalene-2,3-epoxide;(S)-squalene-2,3-epoxide; 2,3-Oxidosqualene, (all-e)-(+-)-isomer; 2,3-Oxidosqualene, (R-(all-e))-isomer; 2,3-Oxidosqualene, (S-(all-e))-isomer; (RS)-2,3-Epoxy-2,3-dihydrosqualene; (3S)-2,3-Epoxy-2,3-dihydrosqualene; (3S)-2,3-Dihydro-2,3-epoxysqualene; (S)-2,3-Dihydro-2,3-epoxysqualene; (S)-2,3-Epoxy-2,3-dihydrosqualene; 2,3-Epoxy-2,3-dihydrosqualene; 2,3-Oxidosqualene, (R)-isomer; 2,3-Oxidosqualene, (S)-isomer; (R,S)-Squalene 2,3-epoxide; Squalene monohydroperoxide; (3S)-Squalene-2,3-epoxide; (S)-Squalene 2,3-epoxide; (S)-Squalene-2,3-epoxide; (3S)-2,3-Oxidosqualene; (3S)-2,3-Epoxysqualene; (S)-2,3-Oxidosqualene; (S)-2,3-epoxysqualene; (±)-2,3-epoxysqualene; Squalene 2,3(S)-oxide; 2,3(S)-Oxidosqualene; (3R,S)-Oxidosqualene; Squalene 2,3-epoxide; Squalene-2,3-epoxide; 3(S)-Oxidosqualene; (3S)-Oxidosqualene; (±)-squalene oxide; Squalene-2,3-oxide; Squalene 2,3-oxide; 2,3-Epoxisqualene; 2,3-Epoxysqualene; Squalene peroxide; 2,3-Oxidosqualene; Squalene epoxide; Squalene oxide; Squslene oxide; Oxidosqualene; 2,3-EDSQ



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(13)

PlantCyc(4)

代谢反应

951 个相关的代谢反应过程信息。

Reactome(60)

BioCyc(37)

WikiPathways(7)

Plant Reactome(91)

INOH(2)

PlantCyc(753)

COVID-19 Disease Map(1)

PathBank(0)

PharmGKB(0)

3 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

  • 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]
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  • Lili Huang, Jia Li, Hechun Ye, Changfu Li, Hong Wang, Benye Liu, Yansheng Zhang. Molecular characterization of the pentacyclic triterpenoid biosynthetic pathway in Catharanthus roseus. Planta. 2012 Nov; 236(5):1571-81. doi: 10.1007/s00425-012-1712-0. [PMID: 22837051]
  • Zheyong Xue, Lixin Duan, Dan Liu, Jie Guo, Song Ge, Jo Dicks, Paul ÓMáille, Anne Osbourn, Xiaoquan Qi. Divergent evolution of oxidosqualene cyclases in plants. The New phytologist. 2012 Mar; 193(4):1022-1038. doi: 10.1111/j.1469-8137.2011.03997.x. [PMID: 22150097]
  • Chunhua Zhou, Daqiu Zhao, Yanle Sheng, Guohua Liang, Jun Tao. Molecular cloning and expression of squalene synthase and 2,3-oxidosqualene cyclase genes in persimmon (Diospyros kaki L.) fruits. Molecular biology reports. 2012 Feb; 39(2):1125-32. doi: 10.1007/s11033-011-0841-z. [PMID: 21573791]
  • Hongmei Luo, Chao Sun, Yongzhen Sun, Qiong Wu, Ying Li, Jingyuan Song, Yunyun Niu, Xianglin Cheng, Hongxi Xu, Chuyuan Li, Juyan Liu, André Steinmetz, Shilin Chen. Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin-biosynthetic genes and genetic markers. BMC genomics. 2011 Dec; 12 Suppl 5(?):S5. doi: 10.1186/1471-2164-12-s5-s5. [PMID: 22369100]
  • Hikaru Seki, Satoru Sawai, Kiyoshi Ohyama, Masaharu Mizutani, Toshiyuki Ohnishi, Hiroshi Sudo, Ery Odette Fukushima, Tomoyoshi Akashi, Toshio Aoki, Kazuki Saito, Toshiya Muranaka. Triterpene functional genomics in licorice for identification of CYP72A154 involved in the biosynthesis of glycyrrhizin. The Plant cell. 2011 Nov; 23(11):4112-23. doi: 10.1105/tpc.110.082685. [PMID: 22128119]
  • Yoshi-Shige Inagaki, Graham Etherington, Katrin Geisler, Ben Field, Melissa Dokarry, Kousuke Ikeda, Yukako Mutsukado, Jo Dicks, Anne Osbourn. Investigation of the potential for triterpene synthesis in rice through genome mining and metabolic engineering. The New phytologist. 2011 Jul; 191(2):432-448. doi: 10.1111/j.1469-8137.2011.03712.x. [PMID: 21501172]
  • Marko Lens, Marie-Helen Podesta Marty. Assessment of the kinetics of the antioxidative capacity of topical antioxidants. Journal of drugs in dermatology : JDD. 2011 Mar; 10(3):262-7. doi: ". [PMID: 21369642]
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