Tetrahydrocoptisine (BioDeep_00000184276)

Main id: BioDeep_00000229954

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]tetracosa-2(10),3,8,15(23),16(20),21-hexaene

化学式: C19H17NO4 (323.1158)
中文名称: 四氢黄连碱, 四氢可的松
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(C(CCN2CC3=C4OCOC4=CC=C3CC21)=C5)=CC6=C5OCO6
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

描述信息

(±)-Stylopine (Tetrahydrocoptisine) is an alkaloid compound originally isolated from Corydalis tubers that exhibits anti-inflammatory and anti-parasitic activities[1][2].
(±)-Stylopine (Tetrahydrocoptisine) is an alkaloid compound originally isolated from Corydalis tubers that exhibits anti-inflammatory and anti-parasitic activities[1][2].

同义名列表

7 个代谢物同义名

5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]tetracosa-2(10),3,8,15(23),16(20),21-hexaene; 6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4,5-g)quinolizine; stylopine, 14C-labeled, (+,-)-isomer; stylopine, (S)-isomer; Tetrahydrocoptisine; stylopine; (±)-Stylopine



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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亚细胞结构定位 关联基因列表
Cytoplasm 8 AKR1C3, APOE, CDK16, MAPK14, PTGS2, TGFB1, TJP1, VEGFA
Peripheral membrane protein 5 ACHE, CDK16, CYP1B1, PTGS2, TJP1
Endoplasmic reticulum membrane 2 CYP1B1, PTGS2
Nucleus 10 ACHE, AKR1C3, APOE, CDK16, CSNK2A1, KDR, MAPK14, TGFB1, TJP1, VEGFA
cytosol 5 AKR1C3, CDK16, CSNK2A1, MAPK14, TJP1
dendrite 1 APOE
nucleoplasm 2 CSNK2A1, MAPK14
Cell membrane 6 ACHE, CDK16, KDR, PROKR2, TJP1, TNF
Cytoplasmic side 2 CDK16, TJP1
Multi-pass membrane protein 1 PROKR2
Synapse 1 ACHE
cell junction 2 KDR, TJP1
cell surface 4 ACHE, TGFB1, TNF, VEGFA
glutamatergic synapse 2 APOE, MAPK14
Golgi apparatus 4 ACHE, APOE, KDR, VEGFA
neuromuscular junction 1 ACHE
neuronal cell body 4 APOE, TGFB1, TGFB2, TNF
synaptic vesicle 1 CDK16
Cytoplasmic vesicle, secretory vesicle 1 CDK16
endosome 1 KDR
plasma membrane 12 ACHE, APOE, BCHE, CDK16, CSNK2A1, F2, KDR, MUC2, PROKR2, TGFB1, TJP1, TNF
Membrane 4 ACHE, APOE, CYP1B1, VEGFA
apical plasma membrane 1 TJP1
axon 2 TGFB1, TGFB2
basolateral plasma membrane 1 TJP1
caveola 1 PTGS2
extracellular exosome 3 AKR1C3, APOE, F2
endoplasmic reticulum 4 APOE, KDR, PTGS2, VEGFA
extracellular space 11 ACHE, APOE, BCHE, F2, IL17A, IL6, MUC2, TGFB1, TGFB2, TNF, VEGFA
perinuclear region of cytoplasm 1 ACHE
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 2 PTGS2, TJP1
intracellular membrane-bounded organelle 2 CSNK2A1, CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
Secreted 9 ACHE, APOE, BCHE, F2, IL17A, IL6, MUC2, TGFB1, VEGFA
extracellular region 13 ACHE, APOE, BCHE, F2, IL17A, IL6, KDR, MAPK14, MUC2, TGFB1, TGFB2, 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
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 3 APOE, TGFB1, VEGFA
chylomicron 1 APOE
high-density lipoprotein particle 1 APOE
low-density lipoprotein particle 1 APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 1 APOE
microtubule cytoskeleton 1 CDK16
Early endosome 2 APOE, KDR
apical part of cell 1 TJP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 KDR, TNF
extracellular matrix 4 APOE, MUC2, TGFB1, VEGFA
basement membrane 1 ACHE
PML body 1 CSNK2A1
collagen-containing extracellular matrix 5 APOE, F2, MUC2, TGFB1, TGFB2
secretory granule 2 TGFB1, 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
receptor complex 1 KDR
neuron projection 2 CDK16, PTGS2
cell projection 1 TJP1
phagocytic cup 1 TNF
Cell projection, podosome 1 TJP1
podosome 1 TJP1
Secreted, extracellular space 1 APOE
spindle pole 1 MAPK14
blood microparticle 4 APOE, BCHE, F2, TGFB1
Lipid-anchor, GPI-anchor 1 ACHE
sorting endosome 1 KDR
Melanosome 1 APOE
side of membrane 1 ACHE
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
Golgi lumen 3 F2, MUC2, TGFB1
endoplasmic reticulum lumen 5 APOE, BCHE, F2, IL6, PTGS2
platelet alpha granule lumen 3 TGFB1, TGFB2, VEGFA
tight junction 1 TJP1
nuclear envelope lumen 1 BCHE
clathrin-coated endocytic vesicle membrane 1 APOE
Synapse, synaptosome 1 CDK16
synaptic cleft 2 ACHE, APOE
Sin3-type complex 1 CSNK2A1
apical junction complex 1 TJP1
cyclin-dependent protein kinase holoenzyme complex 1 CDK16
discoidal high-density lipoprotein particle 1 APOE
endocytic vesicle lumen 1 APOE
[Latency-associated peptide]: Secreted, extracellular space, extracellular matrix 2 TGFB1, TGFB2
[Transforming growth factor beta-1]: Secreted 1 TGFB1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
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
[Transforming growth factor beta-2]: Secreted 1 TGFB2
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

  • 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]
  • 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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