Genkwanin (BioDeep_00000017257)

 

Secondary id: BioDeep_00000000181, BioDeep_00000270248

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-

化学式: C16H12O5 (284.0684702)
中文名称: 芫花素, 4',5-二羟基-7-甲氧基黄酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.11%

分子结构信息

SMILES: C1(OC)=CC2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1
InChI: InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

描述信息

Genkwanin is a monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated. It has a role as a metabolite. It is a dihydroxyflavone and a monomethoxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a genkwanin(1-).
Genkwanin is a natural product found in Odontites viscosus, Eupatorium capillifolium, and other organisms with data available.
A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated.
Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.
Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

同义名列表

40 个代谢物同义名

4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-; 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-; 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one #; 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromen-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one; 4,5-Dihydroxy-7-methoxyflavone, AldrichCPR; n-2,4-dimethylphenyl-n-methylformamidine; 4',5-DIHYDROXY-7-METHOXYFLAVONE; Flavone, 4,5-dihydroxy-7-methoxy-; 4,5-dihydroxy-7-methoxy flavone; 5,4-dihydroxy-7-methoxy-flavone; Genkwanin, analytical standard; 4,5-Dihydroxy-7-methoxyflavone; 5,4-dihydroxy-7-methoxyflavone; 4,5-dihydroxy-7-methoxyflavone; JPMYFOBNRRGFNO-UHFFFAOYSA-N; Genkwanin, >=98\\% (HPLC); Apigenin 7-methyl ether; 7O-methyl-apigenin; 7-O-Methylapigenin; 7-Methoxyapigenin; Spectrum4_001667; 7-Methylapigenin; Spectrum3_001401; Spectrum5_000573; Spectrum2_001355; UNII-5K3I5D6B2B; DivK1c_006931; KBio2_003378; KBio2_000810; KBio2_005946; KBio3_002262; KBio1_001875; Puddumetin; gengkwanin; 5K3I5D6B2B; Henquanin; Gonkwanin; Genkwanin



数据库引用编号

18 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

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)

282 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。



文献列表

  • Álvaro Pérez-Valero, Suhui Ye, Patricia Magadán-Corpas, Claudio J Villar, Felipe Lombó. Metabolic engineering in Streptomyces albidoflavus for the biosynthesis of the methylated flavonoids sakuranetin, acacetin, and genkwanin. Microbial cell factories. 2023 Nov; 22(1):234. doi: 10.1186/s12934-023-02247-3. [PMID: 37964284]
  • Naoual El Menyiy, Sara Aboulaghras, Saad Bakrim, Rania Moubachir, Doaue Taha, Asaad Khalid, Ashraf N Abdalla, Alanood S Algarni, Andi Hermansyah, Long Chiau Ming, Marius Emil Rusu, Abdelhakim Bouyahya. Genkwanin: An emerging natural compound with multifaceted pharmacological effects. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Jul; 165(?):115159. doi: 10.1016/j.biopha.2023.115159. [PMID: 37481929]
  • Lei Xu, Gejin Lu, Baihe Zhan, Lijuan Wei, Xuming Deng, Qiaoling Zhang, Xue Shen, Jianfeng Wang, Haihua Feng. Uncovering the efficacy and mechanisms of Genkwa flos and bioactive ingredient genkwanin against L. monocytogenes infection. Journal of ethnopharmacology. 2022 Oct; 297(?):115571. doi: 10.1016/j.jep.2022.115571. [PMID: 35870686]
  • Zhengshi Chen, Yongheng He, Fan Hu, Mei Li, Yanru Yao. Genkwanin Alleviates Mitochondrial Dysfunction and Oxidative Stress in a Murine Model of Experimental Colitis: The Participation of Sirt1. Annals of clinical and laboratory science. 2022 Mar; 52(2):301-313. doi: . [PMID: 35414509]
  • Peng Zeng, Meng Fang, Han Zhao, Jing Guo. A network pharmacology approach to uncover the key ingredients in Ginkgo Folium and their anti-Alzheimer's disease mechanisms. Aging. 2021 07; 13(14):18993-19012. doi: 10.18632/aging.203348. [PMID: 34315132]
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  • Hua-Feng Yin, Chun-Ming Yin, Ting Ouyang, Shu-Ding Sun, Wei-Guo Chen, Xiao-Lin Yang, Xin He, Chun-Feng Zhang. Self-Nanoemulsifying Drug Delivery System of Genkwanin: A Novel Approach for Anti-Colitis-Associated Colorectal Cancer. Drug design, development and therapy. 2021; 15(?):557-576. doi: 10.2147/dddt.s292417. [PMID: 33603345]
  • Hui Ao, Yijing Li, Haowen Li, Yian Wang, Meihua Han, Yifei Guo, Rongxing Shi, Feng Yue, Xiangtao Wang. Preparation of hydroxy genkwanin nanosuspensions and their enhanced antitumor efficacy against breast cancer. Drug delivery. 2020 Dec; 27(1):816-824. doi: 10.1080/10717544.2020.1770372. [PMID: 32489130]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Yarigui Bao, Yue-Wen Sun, Jun Ji, Lu Gan, Chun-Feng Zhang, Chong-Zhi Wang, Chun-Su Yuan. Genkwanin ameliorates adjuvant-induced arthritis in rats through inhibiting JAK/STAT and NF-κB signaling pathways. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Oct; 63(?):153036. doi: 10.1016/j.phymed.2019.153036. [PMID: 31401534]
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  • Seung Cheol Baek, Mi Hyeon Park, Hyung Won Ryu, Jae Pil Lee, Myung-Gyun Kang, Daeui Park, Chul Min Park, Sei-Ryang Oh, Hoon Kim. Rhamnocitrin isolated from Prunus padus var. seoulensis: A potent and selective reversible inhibitor of human monoamine oxidase A. Bioorganic chemistry. 2019 03; 83(?):317-325. doi: 10.1016/j.bioorg.2018.10.051. [PMID: 30396116]
  • Yi Tao, Dandan Su, Weidong Li, Baochang Cai. Pharmacokinetic comparisons of six components from raw and vinegar-processed Daphne genkwa aqueous extracts following oral administration in rats by employing UHPLC-MS/MS approaches. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Mar; 1079(?):34-40. doi: 10.1016/j.jchromb.2018.02.005. [PMID: 29428673]
  • Yijing Li, Jingyi Hong, Haowen Li, Xiaoyu Qi, Yifei Guo, Meihua Han, Xiangtao Wang. Genkwanin nanosuspensions: a novel and potential antitumor drug in breast carcinoma therapy. Drug delivery. 2017 Nov; 24(1):1491-1500. doi: 10.1080/10717544.2017.1384519. [PMID: 28961040]
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  • Xue Wang, Zi-Jing Song, Xin He, Run-Qi Zhang, Chun-Feng Zhang, Fei Li, Chong-Zhi Wang, Chun-Su Yuan. Antitumor and immunomodulatory activity of genkwanin on colorectal cancer in the APC(Min/+) mice. International immunopharmacology. 2015 Dec; 29(2):701-707. doi: 10.1016/j.intimp.2015.09.006. [PMID: 26388189]
  • Lan Wei, Xiaobo Wang, Shanxue Mu, Lixin Sun, Zhiguo Yu. Ultra high performance liquid chromatography with electrospray ionization tandem mass spectrometry coupled with hierarchical cluster analysis to evaluate Wikstroemia indica (L.) C. A. Mey. from different geographical regions. Journal of separation science. 2015 Jun; 38(12):2093-100. doi: 10.1002/jssc.201401398. [PMID: 25866087]
  • Lin Li, Fang-zhou Yin, Tu-lin Lu, Hong-yue Guan, Bao-chang Cai. [Fingerprint of Vinegar Processed Genkwa Flos Based on Improving Euclidean Distance]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1168-71. doi: . [PMID: 26762055]
  • Tao Fujiwara, Ayumi Uehara, Junichi Kitajima, Tsukasa Iwashina, Sadamu Matsumoto, Yasuyuki Watano. Genkwanin 4'-O-glucosyl-(1 --> 2)-rhamnoside from new chemotype of Asplenium normale in Japan. Natural product communications. 2014 Sep; 9(9):1289-90. doi: . [PMID: 25918794]
  • Yuan Gao, Fen Liu, Lei Fang, Runlan Cai, Chuanjie Zong, Yun Qi. Genkwanin inhibits proinflammatory mediators mainly through the regulation of miR-101/MKP-1/MAPK pathway in LPS-activated macrophages. PloS one. 2014; 9(5):e96741. doi: 10.1371/journal.pone.0096741. [PMID: 24800851]
  • Yanqing Song, Sixi Zhang, Hong Liu, Xiangqun Jin. Determination of genkwanin in rat plasma by liquid chromatography-tandem mass spectrometry: application to a bioavailability study. Journal of pharmaceutical and biomedical analysis. 2013 Oct; 84(?):129-34. doi: 10.1016/j.jpba.2013.06.006. [PMID: 23831487]
  • Catheleeya Mekjaruskul, Michael Jay, Bungorn Sripanidkulchai. Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2342-53. doi: 10.1124/dmd.112.047142. [PMID: 22961680]
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  • Chia-Wen Chang, Yan-Lii Leu, Jim-Tong Horng. Daphne Genkwa sieb. Et zucc. Water-soluble extracts act on enterovirus 71 by inhibiting viral entry. Viruses. 2012 04; 4(4):539-56. doi: 10.3390/v4040539. [PMID: 22590685]
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