Scopolin (BioDeep_00000000343)

 

Secondary id: BioDeep_00000228171

natural product PANOMIX_OTCML-2023


代谢物信息卡片


6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

化学式: C16H18O9 (354.0951)
中文名称: 大麦草碱7-O-葡萄糖苷, 东莨菪苷, 东莨菪甙
谱图信息: 最多检出来源 Viridiplantae(plant) 18.76%

分子结构信息

SMILES: c1(c(cc2c(c1)ccc(=O)o2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)OC
InChI: InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1

描述信息

Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a monosaccharide derivative, a member of coumarins and a beta-D-glucoside. It is functionally related to a scopoletin.
Scopolin is a natural product found in Artemisia ordosica, Astragalus onobrychis, and other organisms with data available.
See also: Chamaemelum nobile flower (part of).
A member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.
Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].
Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].
Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

同义名列表

27 个代谢物同义名

6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one; 2H-1-Benzopyran-2-one, 7-(.beta.-D-glucopyranosyloxy)-6-methoxy-; 2H-1-Benzopyran-2-one, 7-(beta-D-glucopyranosyloxy)-6-methoxy-; 7-(beta-D-glucopyranosoyloxy)-6-methoxy-2H-1-benzopyran-2-one; 6-methoxy-2-oxo-2H-chromen-7-yl beta-D-glucopyranoside; 6-METHOXY-7-(.BETA.-D-GLUCOPYRANOSYLOXY)COUMARIN; 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXYCOUMARIN; 7-(beta-D-GLUCOPYRANOSYLOXY)-6-METHOXYCOUMARIN; 6-METHOXY-7-(beta-D-GLUCOPYRANOSYLOXY)COUMARIN; 7beta-D-Glucopyranosyloxy-6-methoxycumarin; 6-METHOXYCOUMARIN 7-O-.BETA.-D-GLUCOSIDE; SCOPOLETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE; 6-METHOXYCOUMARIN 7-O-beta-D-GLUCOSIDE; SCOPOLETIN 7-O-beta-D-GLUCOPYRANOSIDE; 7-O-.BETA.-GLUCOPYRANOSYLSCOPOLETIN; 7-O-beta-GLUCOPYRANOSYLSCOPOLETIN; Scopoletin 7-O-Glucoside; Scopoletin 7-glucoside; scopoletin glucoside; UNII-1Y49270PY8; SCOPOLIN [MI]; Scopoloside; 1Y49270PY8; Murrayin; Scopolin; SCHEMBL14296928; Scopolin



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

220 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(217)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

284 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 9 ADIG, AGO1, ANG, FABP4, GPI, PGK2, PPARG, SIRT1, VEGFA
Peripheral membrane protein 1 ACHE
Endoplasmic reticulum membrane 1 HSP90B1
Nucleus 11 ACHE, ADIG, AGO1, ANG, CEBPA, FABP4, HSP90B1, PGK2, PPARG, SIRT1, VEGFA
cytosol 10 AGO1, ANG, FABP4, GPI, HSP90B1, LEP, PGK2, PPARG, SIRT1, SLC2A4
trans-Golgi network 1 SLC2A4
nucleoplasm 4 AGO1, CEBPA, PPARG, SIRT1
RNA polymerase II transcription regulator complex 2 CEBPA, PPARG
Cell membrane 3 ACHE, SLC2A4, TNF
Multi-pass membrane protein 1 SLC2A4
Synapse 1 ACHE
cell surface 4 ACHE, ADIPOQ, TNF, VEGFA
Golgi apparatus 2 ACHE, VEGFA
Golgi membrane 1 INS
growth cone 1 ANG
mitochondrial inner membrane 1 GPD2
neuromuscular junction 1 ACHE
neuronal cell body 2 ANG, TNF
sarcolemma 1 SLC2A4
smooth endoplasmic reticulum 1 HSP90B1
Presynapse 1 SLC2A4
plasma membrane 3 ACHE, SLC2A4, TNF
Membrane 7 ACHE, ADIG, GPD2, GPI, HSP90B1, SLC2A4, VEGFA
extracellular exosome 5 FABP4, GPI, HSP90B1, PGK2, SLC2A4
endoplasmic reticulum 3 ADIPOQ, HSP90B1, VEGFA
extracellular space 9 ACHE, ADIPOQ, ANG, GPI, IL6, INS, LEP, TNF, VEGFA
perinuclear region of cytoplasm 4 ACHE, HSP90B1, PPARG, SLC2A4
adherens junction 1 VEGFA
mitochondrion 2 GPD2, SIRT1
protein-containing complex 1 HSP90B1
intracellular membrane-bounded organelle 2 CEBPA, PPARG
chromatin silencing complex 1 SIRT1
Secreted 9 ACHE, ADIG, ADIPOQ, ANG, GPI, IL6, INS, LEP, VEGFA
extracellular region 11 ACHE, ADIG, ADIPOQ, ANG, GPI, HSP90B1, IL6, INS, LEP, TNF, VEGFA
Single-pass membrane protein 1 ADIG
Extracellular side 1 ACHE
transcription regulator complex 1 CEBPA
ciliary membrane 1 GPI
external side of plasma membrane 2 SLC2A4, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
multivesicular body 1 SLC2A4
actin cytoskeleton 1 ANG
T-tubule 1 SLC2A4
nucleolus 3 ANG, CEBPA, SIRT1
midbody 1 HSP90B1
Cytoplasm, P-body 1 AGO1
P-body 1 AGO1
clathrin-coated pit 1 SLC2A4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 SLC2A4
heterochromatin 1 SIRT1
Membrane raft 2 SLC2A4, TNF
focal adhesion 1 HSP90B1
extracellular matrix 1 VEGFA
basement membrane 2 ACHE, ANG
collagen trimer 1 ADIPOQ
sarcoplasmic reticulum 1 SLC2A4
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
collagen-containing extracellular matrix 2 ADIPOQ, HSP90B1
secretory granule 1 VEGFA
nuclear inner membrane 1 SIRT1
receptor complex 1 PPARG
chromatin 3 CEBPA, PPARG, SIRT1
phagocytic cup 1 TNF
Chromosome 1 ANG
cytoplasmic ribonucleoprotein granule 1 AGO1
Nucleus, nucleolus 1 ANG
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
Endomembrane system 1 SLC2A4
endosome lumen 1 INS
Lipid droplet 2 ADIG, FABP4
Cytoplasmic vesicle membrane 1 SLC2A4
Melanosome 1 HSP90B1
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
euchromatin 1 SIRT1
side of membrane 1 ACHE
sperm plasma membrane 1 HSP90B1
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
ficolin-1-rich granule lumen 1 GPI
secretory granule lumen 2 GPI, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 HSP90B1, IL6, INS
platelet alpha granule lumen 1 VEGFA
endocytic vesicle 1 ANG
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
vesicle membrane 1 SLC2A4
Sarcoplasmic reticulum lumen 1 HSP90B1
synaptic cleft 1 ACHE
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
RISC complex 1 AGO1
RISC-loading complex 1 AGO1
sperm fibrous sheath 1 PGK2
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
angiogenin-PRI complex 1 ANG
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 HSP90B1
insulin-responsive compartment 1 SLC2A4
[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
C/EBP complex 1 CEBPA
CHOP-C/EBP complex 1 CEBPA
[Isoform H]: Cell membrane 1 ACHE
[Isoform 4]: Nucleus, nucleolus 1 CEBPA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1
glycerol-3-phosphate dehydrogenase (FAD) complex 1 GPD2


文献列表

  • Kunpeng Yu, Cheng Peng, Yanling Lin, Lijun Li, Hui Ni, Qingbiao Li. [Expression of β-glucosidase An-bgl3 from Aspergillus niger for conversion of scopolin]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2023 Mar; 39(3):1232-1246. doi: 10.13345/j.cjb.220709. [PMID: 36994584]
  • Chen Wang, Qin Zhou, Song-Tao Wu. Scopolin obtained from Smilax china L. against hepatocellular carcinoma by inhibiting glycolysis: A network pharmacology and experimental study. Journal of ethnopharmacology. 2022 Oct; 296(?):115469. doi: 10.1016/j.jep.2022.115469. [PMID: 35718053]
  • QianQian Zhuang, Shaopeng Chen, ZhiXin Jua, Yue Yao. Joint transcriptomic and metabolomic analysis reveals the mechanism of low-temperature tolerance in Hosta ventricosa. PloS one. 2021; 16(11):e0259455. doi: 10.1371/journal.pone.0259455. [PMID: 34731224]
  • Eunkuk Park, Chang Gun Lee, Jeonghyun Kim, Eunguk Lim, Subin Yeo, Seon-Yong Jeong. Scopolin Prevents Adipocyte Differentiation in 3T3-L1 Preadipocytes and Weight Gain in an Ovariectomy-Induced Obese Mouse Model. International journal of molecular sciences. 2020 Nov; 21(22):. doi: 10.3390/ijms21228699. [PMID: 33218042]
  • Zhiyong Chen, Mengmeng Wang, Yuanyuan Yang, Xiaomin Cui, Jing Hu, Ye Li, Feng Zhao. Promotion of a quality standard for Porana sinensis Hemsl. based on the efficacy-oriented Effect-Constituent Index. Biomedical chromatography : BMC. 2020 Feb; 34(2):e4726. doi: 10.1002/bmc.4726. [PMID: 31654585]
  • Bo Li, Min Lu, Zixuan Chu, Shanshan Lei, Peilu Sun, Shan Xiong, Suhong Chen. Evaluation of pharmacokinetics, bioavailability and urinary excretion of scopolin and its metabolite scopoletin in Sprague Dawley rats by liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC. 2019 Dec; 33(12):e4678. doi: 10.1002/bmc.4678. [PMID: 31412148]
  • Tie Liu, Xin-Ge Li, Ji-Ye Wang, De-Long Liu, Yong-Ju Wei. Time-resolved fluorescence and chemometrics-assisted excitation-emission fluorescence for qualitative and quantitative analysis of scopoletin and scopolin in Erycibe obtusifolia Benth. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Aug; 219(?):96-103. doi: 10.1016/j.saa.2019.04.019. [PMID: 31030053]
  • Stefanie Döll, Markus Kuhlmann, Twan Rutten, Michael F Mette, Sarah Scharfenberg, Antonios Petridis, Dorothee-Carina Berreth, Hans-Peter Mock. Accumulation of the coumarin scopolin under abiotic stress conditions is mediated by the Arabidopsis thaliana THO/TREX complex. The Plant journal : for cell and molecular biology. 2018 02; 93(3):431-444. doi: 10.1111/tpj.13797. [PMID: 29222952]
  • Ahyoung Yoo, Vikram P Narayan, Eun Young Hong, Wan Kyunn Whang, Taesun Park. Scopolin ameliorates high-fat diet induced hepatic steatosis in mice: potential involvement of SIRT1-mediated signaling cascades in the liver. Scientific reports. 2017 05; 7(1):2251. doi: 10.1038/s41598-017-02416-6. [PMID: 28533555]
  • Peng Du, Mingdao Lei, Yu Liu, Shilin Yang. Simultaneous Determination and Pharmacokinetic Study of Six Components in Rat Plasma by HPLC-MS/MS after Oral Administration of Acanthopanax sessiliflorus Fruit Extract. International journal of molecular sciences. 2016 Dec; 18(1):. doi: 10.3390/ijms18010045. [PMID: 28036026]
  • Jai Malik, Maninder Karan, Karan Vasisht. Attenuating effect of bioactive coumarins from Convolvulus pluricaulis on scopolamine-induced amnesia in mice. Natural product research. 2016; 30(5):578-82. doi: 10.1080/14786419.2015.1025398. [PMID: 25828605]
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