stylopine (BioDeep_00000005739)

 

Secondary id: BioDeep_00001891857

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


6,7,12b,13e-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4,5- g]quinolizine

化学式: C19H17NO4 (323.1158)
中文名称: 金罂粟碱
谱图信息: 最多检出来源 Viridiplantae(plant) 16.88%

分子结构信息

SMILES: c1cc2c(c3c1CC1c4cc5c(cc4CCN1C3)OCO5)OCO2
InChI: InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/s1

描述信息

同义名列表

5 个代谢物同义名

stylopine; 6,7,12b,13e-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4,5- g]quinolizine; l-Tetrahydrocoptisine; (S)-stylopine; Stylopine



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

10 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(8)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

133 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 7 AKR1C3, AKT1, CDK16, MAPK14, PTGS2, TJP1, VEGFA
Peripheral membrane protein 5 ACHE, CDK16, CYP1B1, PTGS2, TJP1
Endoplasmic reticulum membrane 2 CYP1B1, PTGS2
Nucleus 9 ACHE, AKR1C3, AKT1, CDK16, CSNK2A1, KDR, MAPK14, TJP1, VEGFA
cytosol 6 AKR1C3, AKT1, CDK16, CSNK2A1, MAPK14, TJP1
dendrite 1 CHRM1
nucleoplasm 3 AKT1, CSNK2A1, MAPK14
Cell membrane 9 ACHE, AKT1, CDK16, CHRM1, GPRC5A, KDR, PROKR2, TJP1, TNF
Cytoplasmic side 2 CDK16, TJP1
lamellipodium 1 AKT1
Multi-pass membrane protein 3 CHRM1, GPRC5A, PROKR2
Synapse 2 ACHE, CHRM1
cell cortex 1 AKT1
cell junction 2 KDR, TJP1
cell surface 3 ACHE, TNF, VEGFA
glutamatergic synapse 3 AKT1, CHRM1, MAPK14
Golgi apparatus 3 ACHE, KDR, VEGFA
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
postsynapse 1 AKT1
presynaptic membrane 1 CHRM1
synaptic vesicle 1 CDK16
Cytoplasmic vesicle, secretory vesicle 1 CDK16
endosome 1 KDR
plasma membrane 13 ACHE, AKT1, BCHE, CDK16, CHRM1, CSNK2A1, F2, GPRC5A, KDR, MUC2, PROKR2, TJP1, TNF
Membrane 5 ACHE, AKT1, CHRM1, CYP1B1, VEGFA
apical plasma membrane 1 TJP1
basolateral plasma membrane 1 TJP1
caveola 1 PTGS2
extracellular exosome 3 AKR1C3, F2, GPRC5A
endoplasmic reticulum 3 KDR, PTGS2, VEGFA
extracellular space 8 ACHE, BCHE, F2, IL17A, IL6, MUC2, TNF, VEGFA
perinuclear region of cytoplasm 1 ACHE
Schaffer collateral - CA1 synapse 1 CHRM1
Cell junction, tight junction 1 TJP1
adherens junction 2 TJP1, VEGFA
apicolateral plasma membrane 1 TJP1
bicellular tight junction 1 TJP1
gap junction 1 TJP1
intercalated disc 1 TJP1
intercellular canaliculus 1 TJP1
mitochondrion 3 CYP1B1, MAPK14, TJP1
protein-containing complex 3 AKT1, PTGS2, TJP1
intracellular membrane-bounded organelle 3 CSNK2A1, CYP1B1, GPRC5A
Microsome membrane 2 CYP1B1, PTGS2
Secreted 7 ACHE, BCHE, F2, IL17A, IL6, MUC2, VEGFA
extracellular region 10 ACHE, BCHE, F2, IL17A, IL6, KDR, MAPK14, MUC2, TNF, VEGFA
cytoplasmic side of plasma membrane 1 CDK16
[Isoform 2]: Secreted 1 KDR
Extracellular side 1 ACHE
anchoring junction 1 KDR
external side of plasma membrane 3 IL17A, KDR, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
microtubule cytoskeleton 2 AKT1, CDK16
nucleolus 1 GPRC5A
Early endosome 1 KDR
apical part of cell 1 TJP1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 2 AKT1, GPRC5A
postsynaptic membrane 1 CHRM1
Membrane raft 2 KDR, TNF
spindle 1 AKT1
extracellular matrix 2 MUC2, VEGFA
basement membrane 1 ACHE
PML body 1 CSNK2A1
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 2 F2, MUC2
secretory granule 1 VEGFA
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 CHRM1
receptor complex 2 GPRC5A, KDR
neuron projection 2 CDK16, PTGS2
ciliary basal body 1 AKT1
cell projection 1 TJP1
phagocytic cup 1 TNF
Cell projection, podosome 1 TJP1
podosome 1 TJP1
spindle pole 1 MAPK14
blood microparticle 2 BCHE, F2
Lipid-anchor, GPI-anchor 1 ACHE
sorting endosome 1 KDR
Cytoplasmic vesicle membrane 1 GPRC5A
side of membrane 1 ACHE
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
Golgi lumen 2 F2, MUC2
endoplasmic reticulum lumen 4 BCHE, F2, IL6, PTGS2
platelet alpha granule lumen 1 VEGFA
axon terminus 1 CHRM1
tight junction 1 TJP1
postsynaptic density membrane 1 CHRM1
nuclear envelope lumen 1 BCHE
Synapse, synaptosome 1 CDK16
synaptic cleft 1 ACHE
Sin3-type complex 1 CSNK2A1
apical junction complex 1 TJP1
cyclin-dependent protein kinase holoenzyme complex 1 CDK16
cholinergic synapse 1 CHRM1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
protein kinase CK2 complex 1 CSNK2A1
[Isoform H]: Cell membrane 1 ACHE
inner mucus layer 1 MUC2
outer mucus layer 1 MUC2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Jerald J Nair, Johannes van Staden. Antiprotozoal alkaloid principles of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2019 10; 29(20):126642. doi: 10.1016/j.bmcl.2019.126642. [PMID: 31515186]
  • Meng-Ting Zuo, Sha-Sha Liu, Li Lin, Zi-Yuan Wang, Xia Bai, Zhi-Liang Sun, Zhao-Ying Liu. Characterization of N-methylcanadine and N-methylstylopine metabolites in rat liver S9 by high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Rapid communications in mass spectrometry : RCM. 2018 Dec; 32(23):2047-2054. doi: 10.1002/rcm.8286. [PMID: 30252168]
  • Jae Woo Han, Sang Hee Shim, Kyoung Soo Jang, Yong Ho Choi, Hun Kim, Gyung Ja Choi. In Vivo Disease Control Efficacy of Isoquinoline Alkaloids Isolated from Corydalis ternata against Wheat Leaf Rust and Pepper Anthracnose. Journal of microbiology and biotechnology. 2018 Feb; 28(2):262-266. doi: 10.4014/jmb.1707.07009. [PMID: 29141127]
  • Mahdi Yahyazadeh, Purwanto Ratmoyo, Florian Bittner, Fumihiko Sato, Dirk Selmar. Cloning and Characterization of Cheilanthifoline and Stylopine Synthase Genes from Chelidonium majus. Plant & cell physiology. 2017 Aug; 58(8):1421-1430. doi: 10.1093/pcp/pcx077. [PMID: 28633475]
  • A D Bozhadze, V Iu Vachnadze, M S Dzhokhadze, D T Berashvili, A Dzh Bakuridze. [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia]. Georgian medical news. 2013 Apr; ?(217):61-5. doi: . [PMID: 23676491]
  • Shuping Wang, Lei Liu, Lingling Wang, Peng Jiang, Li Xiang, Weidong Zhang, Runhui Liu. Development and validation of liquid chromatography-tandem mass spectrometry method for simultaneous determination of four tertiary alkaloids in rat plasma and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2013 Jan; 72(?):80-8. doi: 10.1016/j.jpba.2012.09.001. [PMID: 23146230]
  • Ji Eun Park, To Dao Cuong, Tran Manh Hung, IkSoo Lee, MinKyun Na, Jin Cheol Kim, SungWoo Ryoo, Jeong Hyung Lee, Jae Sue Choi, Mi Hee Woo, Byung Sun Min. Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells. Bioorganic & medicinal chemistry letters. 2011 Dec; 21(23):6960-3. doi: 10.1016/j.bmcl.2011.09.128. [PMID: 22024033]
  • Zhong-Ze Ma, Wei Xu, Niels H Jensen, Bryan L Roth, Lee-Yuan Liu-Chen, David Y W Lee. Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor. Molecules (Basel, Switzerland). 2008 Sep; 13(9):2303-12. doi: 10.3390/molecules13092303. [PMID: 18830156]
  • David K Liscombe, Peter J Facchini. Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. The Journal of biological chemistry. 2007 May; 282(20):14741-51. doi: 10.1074/jbc.m611908200. [PMID: 17389594]
  • Seon Il Jang, Byung Hee Kim, Woo-Yiel Lee, Sang Jin An, Han Gil Choi, Byung Hun Jeon, Hun-Taeg Chung, Jung-Rae Rho, Young-Jun Kim, Kyu-Yun Chai. Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells. Archives of pharmacal research. 2004 Sep; 27(9):923-9. doi: 10.1007/bf02975845. [PMID: 15473662]
  • R Suau, B Cabezudo, R Rico, F Nájera, J M López-Romero. Direct determination of alkaloid contents in Fumaria species by GC-MS. Phytochemical analysis : PCA. 2002 Nov; 13(6):363-7. doi: 10.1002/pca.669. [PMID: 12494757]
  • F J BANDELIN, W MALESH. Alkaloids of Chelidonium majus, L., leaves and stems. I. dl-Tetrahydrocoptisine. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1956 Oct; 45(10):702-4. doi: 10.1002/jps.3030451014. [PMID: 13366815]
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