Helichysetin (BioDeep_00000017590)

 

Secondary id: BioDeep_00000266799

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-

化学式: C16H14O5 (286.0841)
中文名称: 4,2,4-三羟基-6-甲氧基查耳酮, 蜡菊亭, 4,2',4'-三羟基-6'-甲氧基查耳酮
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 62.5%

分子结构信息

SMILES: C1(O)=CC(OC)=C(C(=O)/C=C/C2C=CC(O)=CC=2)C(O)=C1
InChI: InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

描述信息

Helichrysetin, also known as 2,​4,​4-​trihydroxy-​6-​methoxychalcone, belongs to the class of organic compounds known as 2-hydroxychalcones. These are organic compounds containing a chalcone skeleton that carries a hydroxyl group at the 2-position. Thus, helichrysetin is considered to be a flavonoid lipid molecule. Helichrysetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. BioTransformer predicts that helichysetin is a product of 2-O-methylisoliquiritigenin metabolism via a hydroxylation-of-benzene-ortho-to-edg reaction catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223).
Helichrysetin is a member of chalcones.
Helichrysetin is a natural product found in Alpinia blepharocalyx, Alpinia hainanensis, and other organisms with data available.
Helichrysetin, isolated from the flowers of Helichrysum odoratissimum, is an ID2 (inhibitor of DNA binding 2) inhibitor, and suppresses DCIS (ductal carcinoma in situ) formation. Helichrysetin possess strong inhibitory effects on cell growth and is capable of inducing apoptosis in A549 cells[1][2].
Helichrysetin, isolated from the flowers of Helichrysum odoratissimum, is an ID2 (inhibitor of DNA binding 2) inhibitor, and suppresses DCIS (ductal carcinoma in situ) formation. Helichrysetin possess strong inhibitory effects on cell growth and is capable of inducing apoptosis in A549 cells[1][2].

同义名列表

17 个代谢物同义名

2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-; (E)-1-(2,4-dihydroxy-6-methoxy-phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; (2E)-1-(2,4-DIHYDROXY-6-METHOXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE; (E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-; 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; 1-(2,4-Dihydroxy-6-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propenone; 4,2’,4’-Trihydroxy-6’-methoxychalcone; 2’,4’,4-Trihydroxy-6’-methoxychalcone; 2,4,4-Trihydroxy-6-methoxychalcone; 4,2,4-Trihydroxy-6-methoxychalcone; UNII-MJ0KMG7AW4; Helichrysetin; helichysetin; MJ0KMG7AW4; 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one



数据库引用编号

15 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)

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


文献列表

  • Ping Wang, Jin-Mei Jin, Xiao-Hui Liang, Ming-Zhu Yu, Chun Yang, Fei Huang, Hui Wu, Bei-Bei Zhang, Xiao-Yan Fei, Zheng-Tao Wang, Ren Xu, Hai-Lian Shi, Xiao-Jun Wu. Helichrysetin inhibits gastric cancer growth by targeting c-Myc/PDHK1 axis-mediated energy metabolism reprogramming. Acta pharmacologica Sinica. 2022 Jun; 43(6):1581-1593. doi: 10.1038/s41401-021-00750-0. [PMID: 34462561]
  • Zhiying Wang, Xiaohui Liang, Aizhen Xiong, Lili Ding, Wei Li, Li Yang, Xiaojun Wu, Hailian Shi, Yue Zhou, Zhengtao Wang. Helichrysetin and TNF‑α synergistically promote apoptosis by inhibiting overactivation of the NF‑κB and EGFR signaling pathways in HeLa and T98G cells. International journal of molecular medicine. 2021 04; 47(4):. doi: 10.3892/ijmm.2021.4882. [PMID: 33576459]
  • Wuttichai Jaidee, Raymond J Andersen, Miguel A G Chavez, Yan A Wang, Brian O Patrick, Stephen G Pyne, Chatchai Muanprasat, Suparerk Borwornpinyo, Surat Laphookhieo. Amides and Flavonoids from the Fruit and Leaf Extracts of Melodorum siamensis. Journal of natural products. 2019 02; 82(2):283-292. doi: 10.1021/acs.jnatprod.8b00696. [PMID: 30694059]
  • Chia-Wei Phan, Vikineswary Sabaratnam, Wai-Kuan Yong, Sri Nurestri Abd Malek. The role of chalcones: helichrysetin, xanthohumol, and flavokawin-C in promoting neurite outgrowth in PC12 Adh cells. Natural product research. 2018 May; 32(10):1229-1233. doi: 10.1080/14786419.2017.1331226. [PMID: 28539058]
  • Sarot Cheenpracha, Chatchanok Karalai, Chanita Ponglimanont, Sanan Subhadhirasakul, Supinya Tewtrakul. Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata. Bioorganic & medicinal chemistry. 2006 Mar; 14(6):1710-4. doi: 10.1016/j.bmc.2005.10.019. [PMID: 16263298]
  • M S Ali, Y Tezuka, S Awale, A H Banskota, S Kadota. Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. Journal of natural products. 2001 Mar; 64(3):289-93. doi: 10.1021/np000496y. [PMID: 11277741]
  • M Morimoto, S Kumeda, K Komai. Insect antifeedant flavonoids from Gnaphalium affine D. Don. Journal of agricultural and food chemistry. 2000 May; 48(5):1888-91. doi: 10.1021/jf990282q. [PMID: 10820110]
  • L Van Puyvelde, N De Kimpe, J Costa, V Munyjabo, S Nyirankuliza, E Hakizamungu, N Schamp. Isolation of flavonoids and a chalcone from Helichrysum odoratissimum and synthesis of helichrysetin. Journal of natural products. 1989 May; 52(3):629-33. doi: 10.1021/np50063a025. [PMID: 2778452]