Gentisein (BioDeep_00000007853)

 

Secondary id: BioDeep_00000862061

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


1,3,7-Trihydroxy-9H-xanthen-9-one, 9CI

化学式: C13H8O5 (244.0372)
中文名称: 1,3,7-三羟基-9H-氧杂蒽-9-酮
谱图信息: 最多检出来源 Viridiplantae(plant) 89.62%

分子结构信息

SMILES: c1(cc(c2c(c1)oc1c(c2=O)cc(cc1)O)O)O
InChI: InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H

描述信息

Gentisein is a member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. It has a role as a plant metabolite. It is a member of xanthones and a polyphenol.
Gentisein is a natural product found in Hypericum scabrum, Cratoxylum formosum, and other organisms with data available.
A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7.
Gentisein is found in alcoholic beverages. Gentisein is isolated from Gentiana lutea (yellow gentian
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].

同义名列表

15 个代谢物同义名

1,3,7-Trihydroxy-9H-xanthen-9-one, 9CI; 9H-Xanthen-9-one, 1,3,7-trihydroxy-; 9H-Xanthen-9-one,1,3,7-trihydroxy-; 1,3,7-trihydroxy-9H-xanthen-9-one; Xanthen-9-one, 1,3,7-trihydroxy-; 1,3,7-Trihydroxy-xanthen-9-one; 1,3,7-trihydroxyxanthen-9-one; 1,3,7-trihydroxy-xanthone; 1,3,7-trihydroxyxanthone; UNII-0P3G42TQ63; XANTHONE DERIV; 0P3G42TQ63; Gentisein; NSC 329491; Gentisein



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(2)

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

60 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 11 AKT1, BDNF, CNR1, CNR2, EGFR, FDPS, PIK3C3, PTGS2, STAT6, TLR4, TNK1
Peripheral membrane protein 3 CYP1B1, PTGS2, TNK1
Endosome membrane 2 EGFR, TLR4
Endoplasmic reticulum membrane 4 CYP1B1, EGFR, HSP90B1, PTGS2
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 4 AKT1, EGFR, HSP90B1, STAT6
autophagosome 1 PIK3C3
cytosol 6 AKT1, FDPS, HSP90B1, NGF, PIK3C3, STAT6
dendrite 3 BDNF, CNR2, NGF
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
nucleoplasm 3 AKT1, FDPS, STAT6
RNA polymerase II transcription regulator complex 1 STAT6
Cell membrane 5 AKT1, CNR1, EGFR, OPRD1, TLR4
lamellipodium 1 AKT1
ruffle membrane 1 EGFR
Cell projection, axon 1 CNR1
Early endosome membrane 1 EGFR
Multi-pass membrane protein 2 CNR1, OPRD1
cell cortex 1 AKT1
cell junction 1 EGFR
cell surface 3 EGFR, PLG, TLR4
glutamatergic synapse 5 AKT1, CNR1, EGFR, PIK3C3, PLG
Golgi membrane 1 EGFR
growth cone 1 CNR1
lysosomal membrane 1 GAA
neuronal cell body 1 SERPINI1
postsynapse 1 AKT1
presynaptic membrane 2 CNR1, OPRD1
smooth endoplasmic reticulum 1 HSP90B1
synaptic vesicle 2 BDNF, NGF
Lysosome 1 GAA
Presynapse 1 CNR1
endosome 2 EGFR, PIK3C3
plasma membrane 9 AKT1, CNR1, CNR2, EGFR, GAA, OPRD1, PLG, TLR4, TNK1
synaptic vesicle membrane 1 OPRD1
Membrane 11 AKT1, BDNF, CYP1B1, EGFR, FDPS, GAA, HSP90B1, OPRD1, PIK3C3, TLR4, TNK1
apical plasma membrane 1 EGFR
axon 3 BDNF, CNR1, NGF
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 5 GAA, HSP90B1, LYZ, PLG, SERPINI1
Lysosome membrane 1 GAA
endoplasmic reticulum 3 CNR2, HSP90B1, PTGS2
extracellular space 6 BDNF, EGFR, LYZ, NGF, PLG, SERPINI1
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 BDNF, EGFR, HSP90B1, TLR4
Schaffer collateral - CA1 synapse 1 PLG
mitochondrion 1 CYP1B1
protein-containing complex 4 AKT1, EGFR, HSP90B1, PTGS2
intracellular membrane-bounded organelle 2 CYP1B1, GAA
Microsome membrane 2 CYP1B1, PTGS2
Single-pass type I membrane protein 2 EGFR, TLR4
Secreted 5 BDNF, GAA, NGF, PLG, SERPINI1
extracellular region 6 BDNF, GAA, HSP90B1, LYZ, NGF, PLG
Mitochondrion outer membrane 1 CNR1
mitochondrial outer membrane 1 CNR1
mitochondrial matrix 1 FDPS
Cytoplasmic vesicle lumen 1 SERPINI1
nuclear membrane 1 EGFR
external side of plasma membrane 2 PLG, TLR4
actin cytoskeleton 1 CNR1
perikaryon 2 CNR2, SERPINI1
microtubule cytoskeleton 1 AKT1
midbody 2 HSP90B1, PIK3C3
Early endosome 1 TLR4
cell-cell junction 1 AKT1
vesicle 1 AKT1
postsynaptic membrane 1 CNR2
Membrane raft 2 CNR1, EGFR
focal adhesion 2 EGFR, HSP90B1
spindle 1 AKT1
GABA-ergic synapse 2 CNR1, PIK3C3
Peroxisome 2 FDPS, PIK3C3
intracellular vesicle 1 EGFR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 2 HSP90B1, PLG
axoneme 1 PIK3C3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
Late endosome 1 PIK3C3
ruffle 1 TLR4
receptor complex 2 EGFR, TLR4
neuron projection 2 OPRD1, PTGS2
ciliary basal body 1 AKT1
chromatin 1 STAT6
phagocytic cup 1 TLR4
phagocytic vesicle membrane 1 PIK3C3
blood microparticle 1 PLG
endosome lumen 1 NGF
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
Cell projection, dendrite 1 CNR2
tertiary granule membrane 1 GAA
Melanosome 1 HSP90B1
sperm plasma membrane 1 HSP90B1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
lipopolysaccharide receptor complex 1 TLR4
secretory granule lumen 1 SERPINI1
Golgi lumen 1 NGF
endoplasmic reticulum lumen 3 BDNF, HSP90B1, PTGS2
platelet alpha granule lumen 1 PLG
axon terminus 1 OPRD1
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
azurophil granule membrane 1 GAA
azurophil granule lumen 1 LYZ
postsynaptic density membrane 1 OPRD1
presynaptic endosome 1 PIK3C3
neuronal dense core vesicle 1 OPRD1
clathrin-coated endocytic vesicle membrane 1 EGFR
Sarcoplasmic reticulum lumen 1 HSP90B1
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
ficolin-1-rich granule membrane 1 GAA
dendrite membrane 1 OPRD1
postsynaptic endosome 1 PIK3C3
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
endocytic vesicle lumen 1 HSP90B1
Autolysosome 1 PIK3C3
Cytoplasmic vesicle, secretory vesicle lumen 1 SERPINI1
endoplasmic reticulum chaperone complex 1 HSP90B1
autolysosome lumen 1 GAA
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
spine apparatus 1 OPRD1


文献列表

  • Edwin Risky Sukandar, Sutin Kaennakam, Kitiya Rassamee, Taslim Ersam, Pongpun Siripong, Santi Tip-Pyang. Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra. Journal of natural products. 2019 05; 82(5):1312-1318. doi: 10.1021/acs.jnatprod.9b00046. [PMID: 30978023]
  • Jie Liu, Cao Zhang, Huailing Wang, Lei Zhang, Zhenlei Jiang, Jianrun Zhang, Zhijun Liu, Heru Chen. Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity. European journal of medicinal chemistry. 2018 May; 151(?):158-172. doi: 10.1016/j.ejmech.2018.03.072. [PMID: 29609121]
  • Jie Liu, Jianrun Zhang, Huailing Wang, Zhijun Liu, Cao Zhang, Zhenlei Jiang, Heru Chen. Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them. European journal of medicinal chemistry. 2017 Jun; 133(?):50-61. doi: 10.1016/j.ejmech.2017.03.068. [PMID: 28376372]
  • Qiwen Wang, Chenyao Ma, Yun Ma, Xiang Li, Yong Chen, Jianwei Chen. Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells. Bioorganic & medicinal chemistry letters. 2017 02; 27(3):447-449. doi: 10.1016/j.bmcl.2016.12.045. [PMID: 28065566]
  • Ruishan Wang, Ridao Chen, Jianhua Li, Xiao Liu, Kebo Xie, Dawei Chen, Ying Peng, Jungui Dai. Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase. Journal of natural products. 2016 08; 79(8):2143-7. doi: 10.1021/acs.jnatprod.6b00417. [PMID: 27466696]
  • Mumtaz Ali, Muhammad Arfan, Manzoor Ahmad, Kuldip Singh, Itrat Anis, Habib Ahmad, Muhammad Iqbal Choudhary, Muhammad Raza Shah. Anti-inflammatory xanthones from the twigs of Hypericum oblongifolium wall. Planta medica. 2011 Dec; 77(18):2013-8. doi: 10.1055/s-0031-1280114. [PMID: 21870324]
  • Ngoc Trang Nhu Ngo, Vy Thuy Nguyen, Hoa Van Vo, Ole Vang, Fritz Duus, Thuy-Duong Huynh Ho, Hung Dinh Pham, Lien-Hoa Dieu Nguyen. Cytotoxic Coumarins from the Bark of Mammea siamensis. Chemical & pharmaceutical bulletin. 2010 Nov; 58(11):1487-91. doi: 10.1248/cpb.58.1487. [PMID: 21048341]
  • He Zhong Jiang, Xiao Fang Quan, Wei Xi Tian, Jiang Miao Hu, Peng Cheng Wang, Sheng Zhuo Huang, Zhong Quan Cheng, Wen Juan Liang, Jun Zhou, Xiao Feng Ma, You Xing Zhao. Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana. Bioorganic & medicinal chemistry letters. 2010 Oct; 20(20):6045-7. doi: 10.1016/j.bmcl.2010.08.061. [PMID: 20817450]
  • Mohammad Arfan, Mumtaz Ali, Habib Ahmad, Itrat Anis, Ajmal Khan, M Iqbal Choudhary, Muhammad Raza Shah. Urease inhibitors from Hypericum oblongifolium WALL. Journal of enzyme inhibition and medicinal chemistry. 2010 Apr; 25(2):296-9. doi: 10.3109/14756360903179385. [PMID: 20222765]
  • Hui Wang, Guan Ye, Chun-Hui Ma, Yi-Hong Tang, Ming-Song Fan, Zhi-Xiong Li, Cheng-Gang Huang. Identification and determination of four metabolites of mangiferin in rat urine. Journal of pharmaceutical and biomedical analysis. 2007 Dec; 45(5):793-8. doi: 10.1016/j.jpba.2007.07.019. [PMID: 17723287]
  • Hai-Tao Chang, Feng Niu, Jing Wen, Yong Jiang, Peng-Fei Tu. [Studies on xanthones from herbs of Polygala telephioides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Nov; 32(21):2259-61. doi: . [PMID: 18309668]
  • D Zheleva-Dimitrova, R Gevrenova, P Nedialkov, G Kitanov. Simultaneous determination of benzophenones and gentisein in Hypericum annulatum Moris by high-performance liquid chromatography. Phytochemical analysis : PCA. 2007 Jan; 18(1):1-6. doi: 10.1002/pca.940. [PMID: 17260692]
  • Georgi Momekov, Paraskev T Nedialkov, Gerassim M Kitanov, Dimitrina Zh Zheleva-Dimitrova, Tzvetomira Tzanova, Ulrich Girreser, Margarita Karaivanova. Cytoprotective effects of 5 benzophenones and a xanthone from Hypericum annulatum in models of epirubicin-induced cytotoxicity: SAR-analysis and mechanistic investigations. Medicinal chemistry (Shariqah (United Arab Emirates)). 2006 Jul; 2(4):377-84. doi: 10.2174/157340606777724103. [PMID: 16848749]
  • Mitka Mitcheva, Magdalena Kondeva, Vessela Vitcheva, Paraskev Nedialkov, Gerassim Kitanov. Effect of benzophenones from Hypericum annulatum on carbon tetrachloride-induced toxicity in freshly isolated rat hepatocytes. Redox report : communications in free radical research. 2006; 11(1):3-8. doi: 10.1179/135100006x100968. [PMID: 16571270]
  • Zhizhen Zhang, Hala N ElSohly, Melissa R Jacob, David S Pasco, Larry A Walker, Alice M Clark. Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii. Planta medica. 2002 Jan; 68(1):49-54. doi: 10.1055/s-2002-20049. [PMID: 11842327]
  • Cécile Morel, Denis Séraphin, Agnès Teyrouz, Gérald Larcher, Jean-Philippe Bouchara, Marc Litaudon, Pascal Richomme, Jean Bruneton. New and antifungal xanthones from Calophyllum caledonicum. Planta medica. 2002 Jan; 68(1):41-4. doi: 10.1055/s-2002-19867. [PMID: 11842325]