2',4',6'-Trihydroxyacetophenone (BioDeep_00000001086)

 

Secondary id: BioDeep_00000407823, BioDeep_00000863047

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2 inverted exclamation mark ,4 inverted exclamation mark ,6 inverted exclamation mark -Trihydroxyacetophenone

化学式: C8H8O4 (168.0422568)
中文名称: 2,4,6-三羟基苯乙酮 一水合物, 2,4,6-三羟基苯乙酮, 2,4,6-三羟基苯乙酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.59%

分子结构信息

SMILES: CC(=O)C1=C(C=C(C=C1O)O)O
InChI: InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3

描述信息

2,4,6-trihydroxyacetophenone is a benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides. It has a role as a MALDI matrix material and a plant metabolite. It is a methyl ketone, a benzenetriol and an aromatic ketone.
2,4,6-Trihydroxyacetophenone is a natural product found in Artemisia gypsacea, Daldinia eschscholtzii, and other organisms with data available.
A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.
2,4,6-Trihydroxyacetophenone is found in fruits. 2,4,6-Trihydroxyacetophenone is isolated from bark of Prunus domestica (plum
Phloracetophenone (2,4,6-trihydroxyacetophenone) is the aglycone part of acetophenone glycoside obtained from Curcuma comosa Roxb, with cholesterol-lowering activity. Phloracetophenone enhances cholesterol 7α-hydroxylase (CYP7A1) activity[1]. Phloracetophenone stimulats bile secretion mediated through Mrp2[2].
Phloracetophenone (2,4,6-trihydroxyacetophenone) is the aglycone part of acetophenone glycoside obtained from Curcuma comosa Roxb, with cholesterol-lowering activity. Phloracetophenone enhances cholesterol 7α-hydroxylase (CYP7A1) activity[1]. Phloracetophenone stimulats bile secretion mediated through Mrp2[2].

同义名列表

47 个代谢物同义名

2 inverted exclamation mark ,4 inverted exclamation mark ,6 inverted exclamation mark -Trihydroxyacetophenone; InChI=1/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H; 2`,4`,6`-Trihydroxyacetophenone Monohydrate; 2,4,6-TRIHYDROXYACETOPHENONE MONOHYDRATE; 2,4,6-Trihydroxyacetophenone Monohydrate; 1-(2,4,6-Trihydroxyphenyl)ethanone, 9CI; 1-[2,4,6-tris(oxidanyl)phenyl]ethanone; Ethanone, 1-(2,4,6-trihydroxyphenyl)-; Acetophenone, 2,4,6-trihydroxy- (8CI); 1-(2,4,6-Trihydroxyphenyl)ethan-1-one; 1-(2,4,6-trihydroxy-phenyl)-ethanone; 1-(2,4,6-Trihydroxyphenyl)-ethanone; 1-(2,4, 6-Trihydroxyphenyl)ethanone; 2-ACETYLPHLOROGLUCINOL MONOHYDRATE; 1-(2,4,6-trihydroxyphenyl]ethanone; 1-(2,4,6-Trihydroxyphenyl)ethanone; 1-(2,6-Trihydroxyphenyl)ethanone; Ethanone,4,6-trihydroxyphenyl)-; Acetophenone, 2,4,6-trihydroxy-; 2, 4, 6-trihydroxyacetophenone; PHLOROACETOPHENONE MONOHYDRATE; 2,4,6-trihydroxy acetophenone; 2,4,6-trihydroxy-acetophenone; 2,4,6-Trihydroxy-Acetophenone; 2,4,6-Trihydroxyacetophenone; 2,4,6-trihydroxyacetophenone; Acetophenone,4,6-trihydroxy-; 2-Acetyl-1,3,5-benzenetriol; 4-mono-hydroxy-acetophenone; 2,4,-dihydroxy-acetophenone; 2,6-Trihydroxyacetophenone; monoacetylphloroglucinol; 2-Acetylphloroglucinol; Acetylphloroglucinol; Acetophloroglucinol; phloroacetophenone; Acetophloroglucine; Phloracetophenone; Spectrum2_001989; Phloracetophene; UNII-8L7XD8830T; 5-alpha-Thenil; ACon1_001026; 8L7XD8830T; 2,4,6-THA; THAP; 83X



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

12 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

  • Anh Tran, Liting Wan, Zhenbo Xu, Janette M Haro, Bing Li, Jace W Jones. Lithium Hydroxide Hydrolysis Combined with MALDI TOF Mass Spectrometry for Rapid Sphingolipid Detection. Journal of the American Society for Mass Spectrometry. 2021 Jan; 32(1):289-300. doi: 10.1021/jasms.0c00322. [PMID: 33124427]
  • Hee Jo Yoo, Se-Jung Hwang, Jeong-Hun Lee, Wang-Seob Shim, Yun-Woong Choi, Sang Min Cho, Eun Kyoung Chung, Jun-Bom Park, Kyung-Tae Lee. Development and Validation of an LC-MS/MS Assay to Quantitate 2',4',6'-Trihydroxyacetophenone in Rat and Dog Plasma and its Application to a Pharmacokinetic Study. Molecules (Basel, Switzerland). 2020 Sep; 25(19):. doi: 10.3390/molecules25194373. [PMID: 32977631]
  • Zhangpei Zhu, Jiajia Shen, Dawei Wang, Chong Chen, Yangfan Xu, Huimin Guo, Dian Kang, Naoki Hamada, Jing Dong, Guangji Wang, Yan Liang. An auxiliary matrix for routine analysis of small molecules and biological macromolecules using matrix-assisted laser desorption ionization mass spectrometry. Analytical and bioanalytical chemistry. 2019 Feb; 411(5):1041-1052. doi: 10.1007/s00216-018-1532-6. [PMID: 30613842]
  • Naser Jafari, Seyed Jalal Zargar, Mohammad-Reza Delnavazi, Narguess Yassa. Cell Cycle Arrest and Apoptosis Induction of Phloroacetophenone Glycosides and Caffeoylquinic Acid Derivatives in Gastric Adenocarcinoma (AGS) Cells. Anti-cancer agents in medicinal chemistry. 2018; 18(4):610-616. doi: 10.2174/1871520618666171219121449. [PMID: 29256356]
  • Alexander L Eaton, Seema Dalal, M Belen Cassera, Shuqi Zhao, David G I Kingston. Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds. Journal of natural products. 2016 06; 79(6):1679-83. doi: 10.1021/acs.jnatprod.6b00347. [PMID: 27228055]
  • Laetitia Bonifait, Annie Marquis, Salvatore Genovese, Francesco Epifano, Daniel Grenier. Synthesis and antimicrobial activity of geranyloxy- and farnesyloxy-acetophenone derivatives against oral pathogens. Fitoterapia. 2012 Sep; 83(6):996-9. doi: 10.1016/j.fitote.2012.06.003. [PMID: 22698715]
  • Aurélien Thomas, Jade Laveaux Charbonneau, Erik Fournaise, Pierre Chaurand. Sublimation of new matrix candidates for high spatial resolution imaging mass spectrometry of lipids: enhanced information in both positive and negative polarities after 1,5-diaminonapthalene deposition. Analytical chemistry. 2012 Feb; 84(4):2048-54. doi: 10.1021/ac2033547. [PMID: 22243482]
  • Mi-Yeon Cho, Su-Young Park, Sumin Park, Yong Rok Lee, Gi-Dong Han, Jung-Ae Kim. Geranyl derivative of phloroacetophenone induces cancer cell-specific apoptosis through Bax-mediated mitochondrial pathway in MCF-7 human breast cancer cells. Biological & pharmaceutical bulletin. 2012; 35(1):98-104. doi: 10.1248/bpb.35.98. [PMID: 22223344]
  • Eduardo Antonio Ferreira, Eliana Fortes Gris, Jussara Matos Rebello, João Francisco Correia, Luis Flávio de Oliveira, Danilo Wilhelm Filho, Rozangela Curi Pedrosa. The 2',4',6'-trihydroxyacetophenone isolated from Myrcia multiflora has antiobesity and mixed hypolipidemic effects with the reduction of lipid intestinal absorption. Planta medica. 2011 Sep; 77(14):1569-74. doi: 10.1055/s-0030-1270956. [PMID: 21472649]
  • Teresa A Kidarsa, Neal C Goebel, T Mark Zabriskie, Joyce E Loper. Phloroglucinol mediates cross-talk between the pyoluteorin and 2,4-diacetylphloroglucinol biosynthetic pathways in Pseudomonas fluorescens Pf-5. Molecular microbiology. 2011 Jul; 81(2):395-414. doi: 10.1111/j.1365-2958.2011.07697.x. [PMID: 21564338]
  • Alexandre L A Bentes, Rosivaldo S Borges, Waldinei R Monteiro, Luiz G M de Macedo, Cláudio N Alves. Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species. Molecules (Basel, Switzerland). 2011 Feb; 16(2):1749-60. doi: 10.3390/molecules16021749. [PMID: 21339710]
  • Gerald Stübiger, Omar Belgacem. Analysis of lipids using 2,4,6-trihydroxyacetophenone as a matrix for MALDI mass spectrometry. Analytical chemistry. 2007 Apr; 79(8):3206-13. doi: 10.1021/ac062236c. [PMID: 17367115]
  • Jainuch Kanchanapoo, Mrinalini C Rao, Samaisukh Sophasan, Apichart Suksamrarn, Pawinee Piyachaturawat. Inhibitory effects of choleretic hydroxyacetophenones on ileal bile acid transport in rats. Life sciences. 2006 Feb; 78(14):1630-6. doi: 10.1016/j.lfs.2005.07.032. [PMID: 16253286]
  • Juree Charoenteeraboon, Kasem Nithipatikom, William B Campbell, Pawinee Piyachaturawat, Prapon Wilairat, Pornpimol Rongnoparut. Induction of human cholesterol 7alpha-hydroxylase in HepG2 cells by 2,4,6-trihydroxyacetophenone. European journal of pharmacology. 2005 May; 515(1-3):43-6. doi: 10.1016/j.ejphar.2005.03.039. [PMID: 15896733]
  • Alexander Schouten, Grardy van den Berg, Véonique Edel-Hermann, Christian Steinberg, Nadine Gautheron, Claude Alabouvette, C H de Vos, Philippe Lemanceau, Jos M Raaijmakers. Defense responses of Fusarium oxysporum to 2,4-diacetylphloroglucinol, a broad-spectrum antibiotic produced by Pseudomonas fluorescens. Molecular plant-microbe interactions : MPMI. 2004 Nov; 17(11):1201-11. doi: 10.1094/mpmi.2004.17.11.1201. [PMID: 15559985]
  • Christopher A Gray, Perry T Kaye, Aloysius T Nchinda. Chromone studies. Part 13. Synthesis and electron-impact mass spectrometric studies of 5-hydroxy-2-isopropyl-7-methoxychromone, a constituent of the medicinal plant Baeckea frutescens, and side-chain analogues. Journal of natural products. 2003 Aug; 66(8):1144-6. doi: 10.1021/np030097d. [PMID: 12932146]
  • Pawinee Piyachaturawat, Pornpikul Srivoraphan, Aporn Chuncharunee, Prayad Komaratat, Apichart Suksamrarn. Cholesterol lowering effects of a choleretic phloracetophenone in hypercholesterolemic hamsters. European journal of pharmacology. 2002 Mar; 439(1-3):141-7. doi: 10.1016/s0014-2999(02)01453-x. [PMID: 11937104]
  • Pawinee Piyachaturawat, Chatsuda Tubtim, Aporn Chuncharunee, Prayad Komaratat, Apichart Suksamrarn. Evaluation of the acute and subacute toxicity of a choleretic phloracetophenone in experimental animals. Toxicology letters. 2002 Mar; 129(1-2):123-32. doi: 10.1016/s0378-4274(02)00006-1. [PMID: 11879983]
  • S S Saleh, B R Glick. Involvement of gacS and rpoS in enhancement of the plant growth-promoting capabilities of Enterobacter cloacae CAL2 and UW4. Canadian journal of microbiology. 2001 Aug; 47(8):698-705. doi: 10.1139/w01-072. [PMID: 11575495]
  • P Piyachaturawat, N Chai-ngam, A Chuncharunee, P Komaratat, A Suksamrarn. Choleretic activity of phloracetophenone in rats: structure-function studies using acetophenone analogues. European journal of pharmacology. 2000 Jan; 387(2):221-7. doi: 10.1016/s0014-2999(99)00743-8. [PMID: 10650163]