Raupine (BioDeep_00000007254)

   


代谢物信息卡片


Sarpagan-10,17-diol

化学式: C19H22N2O2 (310.1681)
中文名称: 萨杷晋碱
谱图信息: 最多检出来源 Viridiplantae(plant) 80.37%

分子结构信息

SMILES: CC=C1CN2C3CC1C(C2CC4=C3NC5=C4C=C(C=C5)O)CO
InChI: InChI=1S/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-/t12-,15+,17-,18-/m0/s1

描述信息

同义名列表

4 个代谢物同义名

Sarpagan-10,17-diol; Raupine; Sarpagine; Sarpagine



数据库引用编号

14 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(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 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 2 MSMP, TUBB4B
Peripheral membrane protein 3 ACHE, CYP1B1, GORASP1
Endosome membrane 1 ATP6AP1
Endoplasmic reticulum membrane 2 ATP6AP1, CYP1B1
Nucleus 2 ACHE, TUBB4B
cytosol 1 TUBB4B
Cell membrane 1 ACHE
Cytoplasmic side 1 GORASP1
Golgi apparatus membrane 1 GORASP1
Synapse 1 ACHE
cell surface 1 ACHE
Golgi apparatus 2 ACHE, GORASP1
Golgi membrane 2 ATP6AP1, GORASP1
lysosomal membrane 1 ATP6AP1
neuromuscular junction 1 ACHE
plasma membrane 2 ACHE, ATP6AP1
synaptic vesicle membrane 1 ATP6AP1
Membrane 3 ACHE, ATP6AP1, CYP1B1
extracellular exosome 2 ATP6AP1, TUBB4B
extracellular space 2 ACHE, MSMP
perinuclear region of cytoplasm 1 ACHE
mitochondrion 1 CYP1B1
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 ATP6AP1
Secreted 2 ACHE, MSMP
extracellular region 2 ACHE, TUBB4B
Single-pass membrane protein 1 ATP6AP1
Extracellular side 1 ACHE
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP6AP1
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 1 TUBB4B
Cytoplasmic vesicle, clathrin-coated vesicle membrane 1 ATP6AP1
clathrin-coated vesicle membrane 1 ATP6AP1
Cytoplasm, cytoskeleton 1 TUBB4B
microtubule 1 TUBB4B
cis-Golgi network 1 GORASP1
basement membrane 1 ACHE
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
axonemal microtubule 1 TUBB4B
side of membrane 1 ACHE
azurophil granule lumen 1 TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 ATP6AP1, GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
synaptic cleft 1 ACHE
proton-transporting V-type ATPase complex 1 ATP6AP1
proton-transporting two-sector ATPase complex 1 ATP6AP1
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Jianquan Zhu, Chao Zhang, Luyi Liu, Chaoyun Xue, Yukun Cai, Xiao-Yu Liu, Fei Xue, Yong Qin. Total Synthesis of Sarpagine Alkaloid (-)-Normacusine B. Organic letters. 2022 05; 24(19):3515-3520. doi: 10.1021/acs.orglett.2c01177. [PMID: 35544733]
  • Puteri Amelia, Alfarius Eko Nugroho, Yusuke Hirasawa, Toshio Kaneda, Takahiro Tougan, Toshihiro Horii, Hiroshi Morita. Two new bisindole alkaloids from Tabernaemontana macrocarpa Jack. Journal of natural medicines. 2021 Jun; 75(3):633-642. doi: 10.1007/s11418-021-01510-4. [PMID: 33822287]
  • Chun-Hoe Tan, Joanne Soon-Yee Yeap, Siew-Huah Lim, Yun-Yee Low, Kae-Shin Sim, Toh-Seok Kam. The Bisindole Alkaloids Angustilongines M and A from Alstonia penangiana Induce Mitochondrial Apoptosis and G0/G1 Cell Cycle Arrest in HT-29 Cells through Promotion of Tubulin Polymerization. Journal of natural products. 2021 05; 84(5):1524-1533. doi: 10.1021/acs.jnatprod.1c00013. [PMID: 33872002]
  • Puteri Amelia, Alfarius Eko Nugroho, Yusuke Hirasawa, Toshio Kaneda, Takahiro Tougan, Toshihiro Horii, Hiroshi Morita. Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. Journal of natural medicines. 2019 Sep; 73(4):820-825. doi: 10.1007/s11418-019-01317-4. [PMID: 31140017]
  • Md Toufiqur Rahman, Veera V N Phani Babu Tiruveedhula, James M Cook. Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review. Molecules (Basel, Switzerland). 2016 Nov; 21(11):. doi: 10.3390/molecules21111525. [PMID: 27854259]
  • Fangrui Wu, Petra Kerčmar, Chenggui Zhang, Joachim Stöckigt. Sarpagan-Ajmalan-Type Indoles: Biosynthesis, Structural Biology, and Chemo-Enzymatic Significance. The Alkaloids. Chemistry and biology. 2016; 76(?):1-61. doi: 10.1016/bs.alkal.2015.10.001. [PMID: 26827882]
  • Ojas A Namjoshi, James M Cook. Sarpagine and Related Alkaloids. The Alkaloids. Chemistry and biology. 2016; 76(?):63-169. doi: 10.1016/bs.alkal.2015.08.002. [PMID: 26827883]
  • Shin-Jowl Tan, Jun-Lee Lim, Yun-Yee Low, Kae-Shin Sim, Siew-Huah Lim, Toh-Seok Kam. Oxidized derivatives of macroline, sarpagine, and pleiocarpamine alkaloids from Alstonia angustifolia. Journal of natural products. 2014 Sep; 77(9):2068-80. doi: 10.1021/np500439u. [PMID: 25211145]
  • Siew-Huah Lim, Yun-Yee Low, Saravana Kumar Sinniah, Kien-Thai Yong, Kae-Shin Sim, Toh-Seok Kam. Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla. Phytochemistry. 2014 Feb; 98(?):204-15. doi: 10.1016/j.phytochem.2013.11.014. [PMID: 24342109]
  • Christiane Hinse, Christian Richter, Alessandro Provenzani, Joachim Stöckigt. In vivo monitoring of alkaloid metabolism in hybrid plant cell cultures by 2D cryo-NMR without labelling. Bioorganic & medicinal chemistry. 2003 Sep; 11(18):3913-9. doi: 10.1016/s0968-0896(03)00430-9. [PMID: 12927851]
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