Mezerein (BioDeep_00000001012)

 

Secondary id: BioDeep_00000180926, BioDeep_00000910976

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2,4-Pentadienoic acid, 5-phenyl-, (2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phenyl-6H-2,8b-epoxyoxireno(6,7)azulene(5,4-e)-1,3-benzodioxol-10-yl ester, (2E,4E)-

化学式: C38H38O10 (654.2465)
中文名称: 欧瑞香脂, 密执毒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 57.81%

分子结构信息

SMILES: C=C(C)C12OC3(c4ccccc4)OC1C1C4OC4(CO)C(O)C4(O)C(=O)C(C)=CC4C1(O3)C(C)C2OC(=O)C=CC=Cc1ccccc1
InChI: InChI=1S/C38H38O10/c1-21(2)36-30(44-27(40)18-12-11-15-24-13-7-5-8-14-24)23(4)37-26-19-22(3)29(41)35(26,43)33(42)34(20-39)31(45-34)28(37)32(36)46-38(47-36,48-37)25-16-9-6-10-17-25/h5-19,23,26,28,30-33,39,42-43H,1,20H2,2-4H3/b15-11+,18-12+/t23-,26-,28+,30-,31+,32-,33-,34+,35-,36+,37+,38?/m1/s1

描述信息

Crystals or white powder. (NTP, 1992)
Mezerein is a diterpenoid.
D009676 - Noxae > D002273 - Carcinogens
D000970 - Antineoplastic Agents

同义名列表

10 个代谢物同义名

2,4-Pentadienoic acid, 5-phenyl-, (2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phenyl-6H-2,8b-epoxyoxireno(6,7)azulene(5,4-e)-1,3-benzodioxol-10-yl ester, (2E,4E)-; [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] (2E,4E)-5-phenylpenta-2,4-dienoate; 2,4-Pentadienoic acid,5-phenyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10R,10aS)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-6-oxo-2-phen; 5-phenyl-2,4-pentadionate daphnetoxin; 1alpha-alkyldaphnane; tigliane-daphnane; SMP2_000004; Mezerein; daphnane; Mezerein



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)

9 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 5 CAT, IFIH1, MYC, ODC1, PRKX
Peripheral membrane protein 1 MBP
Endoplasmic reticulum membrane 1 HMOX1
Nucleus 8 HMOX1, IFIH1, JUN, MBP, MYC, PLCZ1, PRKX, RFC2
cytosol 8 CAT, HMOX1, IFIH1, IL1B, MBP, ODC1, PLCZ1, PRKCQ
nucleoplasm 6 HMOX1, JUN, MYC, PLCZ1, PRKX, RFC2
RNA polymerase II transcription regulator complex 1 JUN
Cell membrane 1 TNF
Cytoplasmic side 2 HMOX1, MBP
Synapse 1 MBP
cell surface 3 ICAM1, MBP, TNF
Golgi membrane 1 INS
lysosomal membrane 1 EGF
neuronal cell body 2 MBP, TNF
Cytoplasm, cytosol 1 IL1B
Lysosome 1 IL1B
plasma membrane 6 EGF, ICAM1, IFNLR1, MBP, PRKCQ, TNF
Membrane 6 CAT, EGF, HMOX1, ICAM1, IFNLR1, MYC
extracellular exosome 4 CAT, EGF, ICAM1, MBP
endoplasmic reticulum 1 HMOX1
extracellular space 9 EGF, HMOX1, ICAM1, IFNA1, IL1B, IL2, IL24, INS, TNF
perinuclear region of cytoplasm 2 HMOX1, PLCZ1
mitochondrion 2 CAT, IFIH1
protein-containing complex 3 CAT, MBP, MYC
intracellular membrane-bounded organelle 1 CAT
pronucleus 1 PLCZ1
Single-pass type I membrane protein 2 ICAM1, IFNLR1
Secreted 5 IFNA1, IL1B, IL2, IL24, INS
extracellular region 8 CAT, EGF, IL1B, IL2, IL24, INS, MBP, TNF
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 1 CAT
transcription regulator complex 1 JUN
centriolar satellite 1 PRKCQ
external side of plasma membrane 2 ICAM1, TNF
nucleolus 2 MYC, PLCZ1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 PLCZ1
Membrane raft 2 ICAM1, TNF
focal adhesion 2 CAT, ICAM1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 ICAM1, MBP
secretory granule 1 IL1B
chromatin 2 JUN, MYC
phagocytic cup 1 TNF
cell periphery 1 MBP
[Isoform 3]: Nucleus 1 MBP
Nucleus, nucleolus 1 MYC
nuclear chromosome 1 JUN
nuclear envelope 1 MYC
endosome lumen 1 INS
Nucleus, nucleoplasm 1 MYC
euchromatin 1 JUN
myelin sheath 1 MBP
ficolin-1-rich granule lumen 2 CAT, MBP
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
platelet alpha granule lumen 1 EGF
transport vesicle 2 INS, MBP
RNA polymerase II transcription repressor complex 1 MYC
Secreted, extracellular exosome 1 IL1B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 2 ICAM1, PRKCQ
aggresome 1 PRKCQ
Single-pass type IV membrane protein 1 HMOX1
clathrin-coated endocytic vesicle membrane 1 EGF
Rough endoplasmic reticulum 1 MYC
transcription factor AP-1 complex 1 JUN
Myc-Max complex 1 MYC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
compact myelin 1 MBP
internode region of axon 1 MBP
catalase complex 1 CAT
sperm head 1 PLCZ1
[Bone marrow proteoglycan]: Secreted 1 MBP
Ctf18 RFC-like complex 1 RFC2
DNA replication factor C complex 1 RFC2
Myelin membrane 1 MBP
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Xinyi Wang, Yujue Wang, Zijian Liu, Hongwei Zhao, Guo-Dong Yao, Qingbo Liu, Shao-Jiang Song. New daphnane diterpenoidal 1,3,4-oxdiazole derivatives as potential anti-hepatoma agents: Synthesis, biological evaluation and molecular modeling studies. Bioorganic chemistry. 2024 Apr; 145(?):107208. doi: 10.1016/j.bioorg.2024.107208. [PMID: 38354501]
  • Lingjian Tan, Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Di Zhou, Ning Li, Li Huang, Chin-Ho Chen, Wei Li. Daphnepedunins G and H, anti-HIV macrocyclic 3,4-seco-daphnane orthoesters from Daphne pedunculata. Journal of natural medicines. 2024 Jan; 78(1):114-122. doi: 10.1007/s11418-023-01750-6. [PMID: 37713094]
  • Kouharu Otsuki, Tsubasa Kobayashi, Kazuki Nakamura, Takashi Kikuchi, Li Huang, Chin-Ho Chen, Kazuo Koike, Wei Li. LC-MS identification, isolation, and structural elucidation of anti-HIV macrocyclic daphnane orthoesters from Edgeworthia chrysantha. Fitoterapia. 2024 Jan; 172(?):105731. doi: 10.1016/j.fitote.2023.105731. [PMID: 37935270]
  • Zhuo-Yang Cheng, Jing-Xian Ren, Xiao-Bian Xue, Man Wang, Xiao-Qi Yu, Bin Lin, Guo-Dong Yao, Shao-Jiang Song, Xiao-Xiao Huang. Daphnane-type diterpenoids from Stellera chamaejasme L. and their inhibitory activity against hepatocellular carcinoma cells. Phytochemistry. 2023 Aug; 212(?):113725. doi: 10.1016/j.phytochem.2023.113725. [PMID: 37224912]
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  • Lingjian Tan, Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Misaki Okayasu, Isao Azumaya, Di Zhou, Ning Li, Li Huang, Chin-Ho Chen, Wei Li. Daphnepedunins A-F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from Daphne pedunculata. Journal of natural products. 2022 12; 85(12):2856-2864. doi: 10.1021/acs.jnatprod.2c00894. [PMID: 36516989]
  • Xiaoyan He, Xiatiguli Abulizi, Xiaowan Li, Guoxu Ma, Zhaocui Sun, Hongyan Wei, Xudong Xu, Leiling Shi, Jing Zhang. Daphnane-Type Diterpenes from Stelleropsis tianschanica and Their Antitumor Activity. Molecules (Basel, Switzerland). 2022 Sep; 27(17):. doi: 10.3390/molecules27175701. [PMID: 36080468]
  • Babalwa Tembeni, Amanda Sciorillo, Luke Invernizzi, Thomas Klimkait, Lorena Urda, Phanankosi Moyo, Dashnie Naidoo-Maharaj, Nathan Levitties, Kwasi Gyampoh, Guorui Zu, Zhe Yuan, Karam Mounzer, Siphathimandla Nkabinde, Magugu Nkabinde, Nceba Gqaleni, Ian Tietjen, Luis J Montaner, Vinesh Maharaj. HPLC-Based Purification and Isolation of Potent Anti-HIV and Latency Reversing Daphnane Diterpenes from the Medicinal Plant Gnidia sericocephala (Thymelaeaceae). Viruses. 2022 06; 14(7):. doi: 10.3390/v14071437. [PMID: 35891417]
  • Si-Hui Mi, Peng Zhao, Qian Li, Hao Zhang, Rui Guo, Yu-Yang Liu, Bin Lin, Guo-Dong Yao, Shao-Jiang Song, Xiao-Xiao Huang. Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies. Phytochemistry. 2022 Jun; 198(?):113144. doi: 10.1016/j.phytochem.2022.113144. [PMID: 35283165]
  • Ahmed H H El-Desoky, Keisuke Eguchi, Naoki Kishimoto, Toshifumi Asano, Hikaru Kato, Yuki Hitora, Shunsuke Kotani, Teruya Nakamura, Soken Tsuchiya, Teppei Kawahara, Masato Watanabe, Mikiyo Wada, Makoto Nakajima, Takashi Watanabe, Shogo Misumi, Sachiko Tsukamoto. Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents. Journal of medicinal chemistry. 2022 02; 65(4):3460-3472. doi: 10.1021/acs.jmedchem.1c01973. [PMID: 35113551]
  • Christian Bailly. Yuanhuacin and Related Anti-Inflammatory and Anticancer Daphnane Diterpenes from Genkwa Flos-An Overview. Biomolecules. 2022 01; 12(2):. doi: 10.3390/biom12020192. [PMID: 35204693]
  • Kouharu Otsuki, Mi Zhang, Takashi Kikuchi, Minami Tsuji, Miyuko Tejima, Zi-Song Bai, Di Zhou, Li Huang, Chin-Ho Chen, Kuo-Hsiung Lee, Ning Li, Kazuo Koike, Wei Li. Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC-MS analysis and phytochemical investigation. Journal of natural medicines. 2021 Sep; 75(4):1058-1066. doi: 10.1007/s11418-021-01551-9. [PMID: 34287744]
  • Shi-Fei Li, Xue Liang, Xing-Kang Wu, Xiang Gao, Li-Wei Zhang. Discovering the Mechanisms of Wikstroelide E as a Potential HIV-Latency-Reversing Agent by Transcriptome Profiling. Journal of natural products. 2021 04; 84(4):1022-1033. doi: 10.1021/acs.jnatprod.0c01039. [PMID: 33721994]
  • Rihan Xie, Guiyang Xia, Jianxun Zhu, Pengcheng Lin, Xiaona Fan, Jiachen Zi. Daphnane-type diterpenoids from Euphorbia fischeriana Steud and their cytotoxic activities. Fitoterapia. 2021 Mar; 149(?):104810. doi: 10.1016/j.fitote.2020.104810. [PMID: 33359422]
  • Yun-Yao Liu, Yan-Ping Liu, Xiao-Ping Wang, Ze-Hua Qiao, Xiao-Mei Yu, Yi-Zhu Zhu, Lan Xie, Lei Qiang, Yan-Hui Fu. Bioactive daphnane diterpenes from Wikstroemia chuii with their potential anti-inflammatory effects and anti-HIV activities. Bioorganic chemistry. 2020 12; 105(?):104388. doi: 10.1016/j.bioorg.2020.104388. [PMID: 33130343]
  • Rong-Rong Pan, Chun-Yan Zhang, Yuan Li, Bing-Bing Zhang, Liang Zhao, Ying Ye, Ya-Nan Song, Miao Zhang, Hong-Yun Tie, Hong Zhang, Jian-Yong Zhu. Daphnane Diterpenoids from Daphne genkwa Inhibit PI3K/Akt/mTOR Signaling and Induce Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells. Journal of natural products. 2020 04; 83(4):1238-1248. doi: 10.1021/acs.jnatprod.0c00003. [PMID: 32223193]
  • Hua-Ding Zhao, Yan Lu, Min Yan, Chin-Ho Chen, Susan L Morris-Natschke, Kuo-Hsiung Lee, Dao-Feng Chen. Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSn. Journal of natural products. 2020 01; 83(1):134-141. doi: 10.1021/acs.jnatprod.9b00993. [PMID: 31860304]
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  • Sheng-Zhuo Huang, Xuan Zhang, Qing-Yun Ma, Hua Peng, Yong-Tang Zheng, Jiang-Miao Hu, Hao-Fu Dai, Jun Zhou, You-Xing Zhao. Anti-HIV-1 tigliane diterpenoids from Excoecaria acertiflia Didr. Fitoterapia. 2014 Jun; 95(?):34-41. doi: 10.1016/j.fitote.2014.02.018. [PMID: 24613801]
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