Sinensetin (BioDeep_00000003832)

 

Secondary id: BioDeep_00000270731

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-chromen-4-one;Sinensetin

化学式: C20H20O7 (372.1209)
中文名称: 甜橙黄酮, 5,6,7,3',4'-五甲氧基黄酮
谱图信息: 最多检出来源 Viridiplantae(plant) 64.74%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1cc(c(cc1)OC)OC)OC)OC)OC
InChI: InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

描述信息

Sinensetin is a pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3 and 4 respectively. It has a role as a plant metabolite. It is functionally related to a flavone.
Sinensetin is a natural product found in Citrus tankan, Citrus keraji, and other organisms with data available.
See also: Tangerine peel (part of); Citrus aurantium fruit rind (part of).
A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3 and 4 respectively.
Sinensetin is found in citrus. Sinensetin is found in orange peel and other plant sources.
Found in orange peel and other plant sources
Sinensetin is a methylated flavonoid found in fruits that has strong anti-vascular and anti-inflammatory properties.
Sinensetin is a methylated flavonoid found in fruits that has strong anti-vascular and anti-inflammatory properties.

同义名列表

17 个代谢物同义名

2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-chromen-4-one;Sinensetin; 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-; 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one; 2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one #; 2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one; 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one; FLAVONE, 3,4,5,6,7-PENTAMETHOXY-; Flavone, 5,6,7,3,4-pentamethoxy; 5,6,7,3,4 -pentamethoxyflavone; 3,4,5,6,7-pentamethoxy flavone; 3,4,5,6,7-pentamethoxyflavone; 5,6,7,3,4-Pentamethoxyflavone; LKMNXYDUQXAUCZ-UHFFFAOYSA-N; Pedalitin permethyl ether; MEGxp0_000957; Sinensetin; Sinensetin



数据库引用编号

22 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(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)

155 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 12 ABCB1, AKT1, CASP3, CYP3A4, EGFR, MAPK14, MTOR, PIK3CA, PRKAA2, PTGS2, TP53, VEGFA
Peripheral membrane protein 3 CYP1B1, MTOR, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 6 CYP1A2, CYP1B1, CYP3A4, EGFR, MTOR, PTGS2
Nucleus 8 AKT1, CASP3, EGFR, MAPK14, MTOR, PRKAA2, TP53, VEGFA
cytosol 7 AKT1, CASP3, MAPK14, MTOR, PIK3CA, PRKAA2, TP53
dendrite 2 MTOR, PRKAA2
phagocytic vesicle 1 MTOR
centrosome 1 TP53
nucleoplasm 6 AKT1, CASP3, MAPK14, MTOR, PRKAA2, TP53
Cell membrane 4 ABCB1, AKT1, EGFR, TNF
Cytoplasmic side 1 MTOR
lamellipodium 2 AKT1, PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 1 ABCB1
Golgi apparatus membrane 1 MTOR
cell cortex 1 AKT1
cell junction 1 EGFR
cell surface 4 ABCB1, EGFR, TNF, VEGFA
glutamatergic synapse 4 AKT1, CASP3, EGFR, MAPK14
Golgi apparatus 2 PRKAA2, VEGFA
Golgi membrane 3 EGFR, INS, MTOR
lysosomal membrane 2 GAA, MTOR
neuronal cell body 3 CASP3, PRKAA2, TNF
postsynapse 1 AKT1
Lysosome 2 GAA, MTOR
endosome 1 EGFR
plasma membrane 7 ABCB1, AKT1, EGFR, GAA, IFNLR1, PIK3CA, TNF
Membrane 12 ABCB1, AKT1, CYP1B1, CYP3A4, EGFR, GAA, IFNLR1, MMP13, MTOR, PRKAA2, TP53, VEGFA
apical plasma membrane 2 ABCB1, EGFR
axon 1 PRKAA2
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 2 ABCB1, GAA
Lysosome membrane 2 GAA, MTOR
endoplasmic reticulum 3 PTGS2, TP53, VEGFA
extracellular space 6 EGFR, IL10, INS, MMP13, TNF, VEGFA
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 EGFR, PIK3CA
adherens junction 1 VEGFA
intercalated disc 1 PIK3CA
mitochondrion 3 CYP1B1, MAPK14, TP53
protein-containing complex 4 AKT1, EGFR, PTGS2, TP53
intracellular membrane-bounded organelle 4 CYP1A2, CYP1B1, CYP3A4, GAA
Microsome membrane 5 CYP1A2, CYP1B1, CYP3A4, MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 EGFR, IFNLR1
Secreted 5 GAA, IL10, INS, MMP13, VEGFA
extracellular region 7 GAA, IL10, INS, MAPK14, MMP13, TNF, VEGFA
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
nuclear membrane 1 EGFR
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 2 MMP13, VEGFA
microtubule cytoskeleton 1 AKT1
nucleolus 1 TP53
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Apical cell membrane 1 ABCB1
Membrane raft 2 EGFR, TNF
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 EGFR
spindle 1 AKT1
extracellular matrix 2 MMP13, VEGFA
intracellular vesicle 1 EGFR
Nucleus, PML body 2 MTOR, TP53
PML body 2 MTOR, TP53
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
secretory granule 1 VEGFA
nuclear speck 2 MAPK14, PRKAA2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 EGFR
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 1 TP53
phagocytic cup 1 TNF
spindle pole 1 MAPK14
site of double-strand break 1 TP53
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
endosome lumen 1 INS
tertiary granule membrane 1 GAA
cytoplasmic stress granule 1 PRKAA2
germ cell nucleus 1 TP53
replication fork 1 TP53
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
platelet alpha granule lumen 1 VEGFA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 EGFR
[Isoform 1]: Nucleus 1 TP53
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, phagosome 1 MTOR
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
autolysosome lumen 1 GAA
[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
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yanhong Sun, Xiaoyan Duan, Fenghe Wang, Huixin Tan, Jiahuan Hu, Wanting Bai, Xinbo Wang, Baolian Wang, Jinping Hu. Inhibitory effects of flavonoids on glucose transporter 1 (GLUT1): From library screening to biological evaluation to structure-activity relationship. Toxicology. 2023 Mar; ?(?):153475. doi: 10.1016/j.tox.2023.153475. [PMID: 36870413]
  • Xiaoqi Wang, Dongli Li, Yong Cao, Chi-Tang Ho, Qingrong Huang. Biotransformation and Quantification of Sinensetin and Its Metabolites in Plasma, Urine, and Feces of Rats. Journal of agricultural and food chemistry. 2021 Dec; 69(47):14143-14150. doi: 10.1021/acs.jafc.1c05024. [PMID: 34797063]
  • Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
  • Dan Liu, Xiangyu Cao, Yuchi Kong, Teng Mu, Jianli Liu. Inhibitory mechanism of sinensetin on α-glucosidase and non-enzymatic glycation: Insights from spectroscopy and molecular docking analyses. International journal of biological macromolecules. 2021 Jan; 166(?):259-267. doi: 10.1016/j.ijbiomac.2020.10.174. [PMID: 33115652]
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  • Seong Min Kim, Sang Eun Ha, Ho Jeong Lee, Shailima Rampogu, Preethi Vetrivel, Hun Hwan Kim, Venu Venkatarame Gowda Saralamma, Keun Woo Lee, Gon Sup Kim. Sinensetin Induces Autophagic Cell Death through p53-Related AMPK/mTOR Signaling in Hepatocellular Carcinoma HepG2 Cells. Nutrients. 2020 Aug; 12(8):. doi: 10.3390/nu12082462. [PMID: 32824273]
  • Xiaoqing Fan, Jie Bai, Minwan Hu, Yanxia Xu, Shengyu Zhao, Yanhong Sun, Baolian Wang, Jinping Hu, Yan Li. Drug interaction study of flavonoids toward OATP1B1 and their 3D structure activity relationship analysis for predicting hepatoprotective effects. Toxicology. 2020 05; 437(?):152445. doi: 10.1016/j.tox.2020.152445. [PMID: 32259555]
  • Jiashun Li, Xiang Jie, Xiaoli Liang, Ziyu Chen, Peifang Xie, Xiping Pan, Beixian Zhou, Jing Li. Sinensetin suppresses influenza a virus-triggered inflammation through inhibition of NF-κB and MAPKs signalings. BMC complementary medicine and therapies. 2020 May; 20(1):135. doi: 10.1186/s12906-020-02918-3. [PMID: 32370749]
  • Angela Bisio, Anna M Schito, Francesca Pedrelli, Ombeline Danton, Jakob K Reinhardt, Giulio Poli, Tiziano Tuccinardi, Thomas Bürgi, Francesco De Riccardis, Mauro Giacomini, Daniela Calzia, Isabella Panfoli, Gian Carlo Schito, Matthias Hamburger, Nunziatina De Tommasi. Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana. Journal of natural products. 2020 04; 83(4):1027-1042. doi: 10.1021/acs.jnatprod.9b01024. [PMID: 32182064]
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  • Yong-Jian Xiong, Zhao-Bin Deng, Jia-Ni Liu, Juan-Juan Qiu, Li Guo, Pan-Pan Feng, Jing-Ru Sui, Da-Peng Chen, Hui-Shu Guo. Enhancement of epithelial cell autophagy induced by sinensetin alleviates epithelial barrier dysfunction in colitis. Pharmacological research. 2019 10; 148(?):104461. doi: 10.1016/j.phrs.2019.104461. [PMID: 31542404]
  • Yin Xu, Xiaojian Lv, Guliang Yang, Jianfeng Zhan, Ming Li, Tao Long, Chi-Tang Ho, Shiming Li. Simultaneous separation of six pure polymethoxyflavones from sweet orange peel extract by high performance counter current chromatography. Food chemistry. 2019 Sep; 292(?):160-165. doi: 10.1016/j.foodchem.2019.04.031. [PMID: 31054661]
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  • Mun Fei Yam, Chu Shan Tan, Ruan Shibao. Vasorelaxant effect of sinensetin via the NO/sGC/cGMP pathway and potassium and calcium channels. Hypertension research : official journal of the Japanese Society of Hypertension. 2018 Oct; 41(10):787-797. doi: 10.1038/s41440-018-0083-8. [PMID: 30111856]
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  • Guor-Jien Wei, Jenn-Feng Sheen, Wen-Chien Lu, Lucy Sun Hwang, Chi-Tang Ho, Ching-I Lin. Identification of sinensetin metabolites in rat urine by an isotope-labeling method and ultrahigh-performance liquid chromatography-electrospray ionization mass spectrometry. Journal of agricultural and food chemistry. 2013 May; 61(21):5016-21. doi: 10.1021/jf3046768. [PMID: 23647150]
  • Seong-Il Kang, Hye-Sun Shin, Hee-Chul Ko, Se-Jae Kim. Effects of sinensetin on lipid metabolism in mature 3T3-L1 adipocytes. Phytotherapy research : PTR. 2013 Jan; 27(1):131-4. doi: 10.1002/ptr.4683. [PMID: 22438091]
  • Saem Han, Hye Min Kim, Sanghyun Lee. Simultaneous determination of polymethoxyflavones in Citrus species, Kiyomi tangor and Satsuma mandarin, by high performance liquid chromatography. Food chemistry. 2012 Sep; 134(2):1220-4. doi: 10.1016/j.foodchem.2012.02.187. [PMID: 23107751]
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  • Mirka Laavola, Riina Nieminen, Mun Fei Yam, Amirin Sadikun, Mohd Zaini Asmawi, Rusliza Basir, Jukka Welling, Heikki Vapaatalo, Riku Korhonen, Eeva Moilanen. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta medica. 2012 May; 78(8):779-86. doi: 10.1055/s-0031-1298458. [PMID: 22516932]
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  • Yang Dong, Guang Ji, Aili Cao, Jianrong Shi, Hailian Shi, Jianqun Xie, Dazheng Wu. [Effects of sinensetin on proliferation and apoptosis of human gastric cancer AGS cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Mar; 36(6):790-4. doi: . [PMID: 21710752]
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