Isoscopoletin (BioDeep_00000000182)

 

Secondary id: BioDeep_00000859576

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2H-1-Benzopyran-2-one, 6-hydroxy-7-methoxy-

化学式: C10H8O4 (192.0423)
中文名称: 异莨菪亭
谱图信息: 最多检出来源 Viridiplantae(plant) 18.51%

分子结构信息

SMILES: COC1=C(C=C2C=CC(=O)OC2=C1)O
InChI: InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3

描述信息

Isoscopoletin is a hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone. It has a role as a plant metabolite. It is a hydroxycoumarin and an aromatic ether. It is functionally related to an esculetin.
Isoscopoletin is a natural product found in Clausena dunniana, Olea capensis, and other organisms with data available.
Isoscopoletin (6-Hydroxy-7-methoxycoumarin) is an active constituent in Artemisia argyi leaves. Isoscopoletin shows substantial inhibition against cell proliferation, with IC50s of 4.0 μM and 1.6 μM for human CCRF-CEM leukaemia cells and multidrug resistant subline CEM/ADR5000, respectively[1]. Isoscopoletin (6-Hydroxy-7-methoxycoumarin) possesses inhibitory activity against HBV replication[2].
Isoscopoletin (6-Hydroxy-7-methoxycoumarin) is an active constituent in Artemisia argyi leaves. Isoscopoletin shows substantial inhibition against cell proliferation, with IC50s of 4.0 μM and 1.6 μM for human CCRF-CEM leukaemia cells and multidrug resistant subline CEM/ADR5000, respectively[1]. Isoscopoletin (6-Hydroxy-7-methoxycoumarin) possesses inhibitory activity against HBV replication[2].

同义名列表

14 个代谢物同义名

2H-1-Benzopyran-2-one, 6-hydroxy-7-methoxy-; 6-Hydroxy-7-methoxy-2H-1-benzopyran-2-one; 6-hydroxy-7-methoxy-2H-chromen-2-one; 6-Hydroxy-7-methoxy-2-benzopyrone; 6-hydroxy-7-methoxy-chromen-2-one; 6-hydroxy-7-methoxychromen-2-one; 6-Hydroxy-7-Methoxycoumarin ,(S); 6-hydroxy-7-methoxycoumarin; SYTYLPHCLSSCOJ-UHFFFAOYSA-N; Esculetin, 7-methyl ether; 7-Methoxyesculetin; Isoscopoletine; Isoscopoletin; Isoscopoletin



数据库引用编号

19 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(1)

代谢反应

5 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

227 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 8 ARG1, CYP1A1, CYP2A13, ELANE, ESR1, FPR1, MARK2, NQO1
Peripheral membrane protein 2 CYP1A1, ESR1
Endoplasmic reticulum membrane 10 CYP1A1, CYP1A2, CYP2A13, UGT1A1, UGT1A10, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B17
Nucleus 4 ARG1, ESR1, NOP2, NQO1
cytosol 5 ARG1, COMT, ELANE, ESR1, NQO1
dendrite 3 COMT, MARK2, NQO1
phagocytic vesicle 1 ELANE
nucleoplasm 3 ESR1, MARK2, NOP2
Cell membrane 3 COMT, ESR1, FPR1
Cytoplasmic side 1 ESR1
Cytoplasmic granule 1 ARG1
Multi-pass membrane protein 1 FPR1
Synapse 2 COMT, NQO1
cell surface 1 ELANE
Golgi apparatus 1 ESR1
mitochondrial inner membrane 2 CYP1A1, HADHA
neuronal cell body 1 NQO1
Cytoplasm, cytosol 1 NQO1
plasma membrane 5 COMT, ESR1, FPR1, MARK2, UGT1A1
Membrane 12 COMT, ESR1, FPR1, MARK2, NQO1, UGT1A1, UGT1A10, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B17
axon 1 COMT
extracellular exosome 2 COMT, ELANE
endoplasmic reticulum 7 ARSI, UGT1A1, UGT1A10, UGT1A6, UGT1A7, UGT1A8, UGT1A9
extracellular space 2 ARG1, ELANE
perinuclear region of cytoplasm 1 UGT1A1
mitochondrion 3 CYP1A1, HADHA, MARK2
protein-containing complex 1 ESR1
intracellular membrane-bounded organelle 5 COMT, CYP1A1, CYP1A2, CYP2A13, UGT1A6
Microsome membrane 2 CYP1A1, CYP1A2
Secreted 1 ARSI
extracellular region 3 ARG1, ARSI, ELANE
Single-pass membrane protein 7 UGT1A1, UGT1A10, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B17
Extracellular side 1 COMT
transcription regulator complex 1 ESR1
nucleolus 1 NOP2
Single-pass type II membrane protein 1 COMT
Cytoplasm, perinuclear region 1 UGT1A1
Mitochondrion inner membrane 2 CYP1A1, HADHA
mitochondrial nucleoid 1 HADHA
collagen-containing extracellular matrix 1 ELANE
secretory granule 1 ELANE
lateral plasma membrane 1 MARK2
chromatin 1 ESR1
Nucleus, nucleolus 1 NOP2
actin filament 1 MARK2
Cell projection, dendrite 1 MARK2
euchromatin 1 ESR1
secretory granule membrane 1 FPR1
endoplasmic reticulum lumen 1 ARSI
transcription repressor complex 1 ELANE
specific granule lumen 2 ARG1, ELANE
azurophil granule membrane 1 FPR1
azurophil granule lumen 2 ARG1, ELANE
mitochondrial fatty acid beta-oxidation multienzyme complex 1 HADHA
[Isoform 1]: Nucleus 1 ESR1
ficolin-1-rich granule membrane 1 FPR1
Cytoplasmic vesicle, phagosome 1 ELANE
endoplasmic reticulum chaperone complex 1 UGT1A1
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
cytochrome complex 1 UGT1A1
microtubule bundle 1 MARK2


文献列表

  • Yang-Liu Xia, Jing-Jing Wang, Shi-Yang Li, Yong Liu, Frank J Gonzalez, Ping Wang, Guang-Bo Ge. Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment. Bioorganic & medicinal chemistry. 2021 01; 29(?):115851. doi: 10.1016/j.bmc.2020.115851. [PMID: 33218896]
  • Anam Fayyaz, Seddy Makwinja, Seppo Auriola, Hannu Raunio, Risto O Juvonen. Comparison of In Vitro Hepatic Scoparone 7-O-Demethylation between Humans and Experimental Animals. Planta medica. 2018 Mar; 84(5):320-328. doi: 10.1055/s-0043-119886. [PMID: 28950382]
  • Hyo Hee Yang, Kyung-Eon Oh, Yang Hee Jo, Jong Hoon Ahn, Qing Liu, Ayman Turk, Jae Young Jang, Bang Yeon Hwang, Ki Yong Lee, Mi Kyeong Lee. Characterization of tyrosinase inhibitory constituents from the aerial parts of Humulus japonicus using LC-MS/MS coupled online assay. Bioorganic & medicinal chemistry. 2018 01; 26(2):509-515. doi: 10.1016/j.bmc.2017.12.011. [PMID: 29254897]
  • Yong Zhao, Chang-An Geng, Chang-Li Sun, Yun-Bao Ma, Xiao-Yan Huang, Tuan-Wu Cao, Kang He, Hao Wang, Xue-Mei Zhang, Ji-Jun Chen. Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris. Fitoterapia. 2014 Jun; 95(?):187-93. doi: 10.1016/j.fitote.2014.03.017. [PMID: 24685503]
  • Pravin O Patil, Sanjay B Bari, Sandip D Firke, Prashant K Deshmukh, Shailesh T Donda, Dilip A Patil. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease. Bioorganic & medicinal chemistry. 2013 May; 21(9):2434-50. doi: 10.1016/j.bmc.2013.02.017. [PMID: 23517722]
  • Rohan A Davis, Daniela Vullo, Alfonso Maresca, Claudiu T Supuran, Sally-Ann Poulsen. Natural product coumarins that inhibit human carbonic anhydrases. Bioorganic & medicinal chemistry. 2013 Mar; 21(6):1539-43. doi: 10.1016/j.bmc.2012.07.021. [PMID: 22892213]
  • Lu-Qing Li, Jun Li, Yan Huang, Qiang Wu, Sheng-Ping Deng, Xiao-Jian Su, Rui-Yun Yang, Ji-Guo Huang, Zi-Zhan Chen, Shan Li. Lignans from the heartwood of Streblus asper and their inhibiting activities to hepatitis B virus. Fitoterapia. 2012 Mar; 83(2):303-9. doi: 10.1016/j.fitote.2011.11.008. [PMID: 22119765]
  • Yasser Abdelaal Selim, Nabil Hassan Ouf. Anti-inflammatory new coumarin from the Ammi majus L. Organic and medicinal chemistry letters. 2012 Jan; 2(1):1. doi: 10.1186/2191-2858-2-1. [PMID: 22373472]
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  • Lin Cheng, Xiaoyu Zhang, Min Zhang, Peng Zhang, Zhihang Song, Zhongjun Ma, Yiyu Cheng, Haibin Qu. Characterization of chemopreventive agents from the dichloromethane extract of Eurycorymbus cavaleriei by liquid chromatography-ion trap mass spectrometry. Journal of chromatography. A. 2009 Jun; 1216(24):4859-67. doi: 10.1016/j.chroma.2009.04.031. [PMID: 19439309]
  • Shu-Hong Tao, Guang-Chun Gao, Shu-Hua Qi, Qing-Xin Li, Si Zhang. [Studies on the chemical constituents of Scyphiphora hydrophyllacea (II)]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 May; 32(5):712-4. doi: . [PMID: 19771844]
  • Zhuo-Ma Dawa, Yan Zhou, Yang Bai, Suo-Lang Gesang, Ping Xie, Li-Sheng Ding. [Studies on chemical constituents of Saussurea laniceps]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 May; 33(9):1032-5. doi: . [PMID: 18652351]
  • Qiong Wang, Chao-Feng Zhang, Mian Zhang, Zheng-Tao Wang. [Study on chemical constituents in roots and rhizomes of Ligularia duciforms II]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 May; 33(9):1018-20. doi: ". [PMID: 18652347]
  • Carlos L Céspedes, J Guillermo Avila, Andrés Martínez, Blanca Serrato, José C Calderón-Mugica, Rafael Salgado-Garciglia. Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). Journal of agricultural and food chemistry. 2006 May; 54(10):3521-7. doi: 10.1021/jf053071w. [PMID: 19127719]
  • Ji Ma, Shannon H Jones, Sidney M Hecht. A coumarin from Mallotus resinosus that mediates DNA cleavage. Journal of natural products. 2004 Sep; 67(9):1614-6. doi: 10.1021/np040129c. [PMID: 15387675]
  • Bao-Ning Su, Eun Jung Park, Zakaria H Mbwambo, Bernard D Santarsiero, Andrew D Mesecar, Harry H S Fong, John M Pezzuto, A Douglas Kinghorn. New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. Journal of natural products. 2002 Sep; 65(9):1278-82. doi: 10.1021/np0202475. [PMID: 12350147]
  • A S Galabov, T Iosifova, E Vassileva, I Kostova. Antiviral activity of some hydroxycoumarin derivatives. Zeitschrift fur Naturforschung. C, Journal of biosciences. 1996 Jul; 51(7-8):558-62. doi: 10.1515/znc-1996-7-815. [PMID: 8810095]