alpha-CEHC (BioDeep_00000027716)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid

化学式: C16H22O4 (278.1518012)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.12%

分子结构信息

SMILES: CC1=C(C)C2=C(CCC(C)(CCC(O)=O)O2)C(C)=C1O
InChI: InChI=1S/C16H22O4/c1-9-10(2)15-12(11(3)14(9)19)5-7-16(4,20-15)8-6-13(17)18/h19H,5-8H2,1-4H3,(H,17,18)

描述信息

alpha-Carboxyethyl hydrochroman (alpha-CEHC) has been identified as a major water-soluble metabolite of vitamin E, which circulates in the blood and is excreted in the urine (PMID: 12420750). About one-third of the alpha-CEHC circulating in the blood is present as alpha-CEHC glucuronide (PMID: 10552913).
2,5,7,8-tetramethyl-2-(2-carboxyethyl)-6-hydroxychroman (alpha-CEHC) has been identified as a major water-soluble metabolite of vitamin E, which circulates in the blood and is excreted with the urine. (PMID 12420750) [HMDB]

同义名列表

12 个代谢物同义名

3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid; 3-(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoate; 2,5,7,8-Tetramethyl-2-(beta-carboxyethyl)-6-hydroxychroman; 6-Hydroxy-2-(2-carboxylethyl)-2,5,7,8-tetramethylchroman; 2,5,7,8-Tetramethyl-2-(β-carboxyethyl)-6-hydroxychroman; 2,5,7,8-Tetramethyl-2(2-carboxyethyl)-6-hydroxychroman; 6-Hydroxy-2-carboxylethyl-2,5,7,8-tetramethylchroman; alpha-Carboxyethyl hydrochroman; α-Carboxyethyl hydrochroman; alpha-CEHC; Α-cehc; a-CEHC



数据库引用编号

8 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

  • α-tocopherol degradation: α-tocopherol + H+ + NADPH + O2 ⟶ 13'-hydroxy-α-tocopherol + H2O + NADP+
  • α-tocopherol degradation: α-tocopherol + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 13'-hydroxy-α-tocopherol + H2O + an oxidized [NADPH-hemoprotein reductase]

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Jungeun Lim, Hyokyoung G Hong, Stephanie J Weinstein, Mary C Playdon, Amanda J Cross, Rachael Stolzenberg-Solomon, Neal D Freedman, Jiaqi Huang, Demetrius Albanes. Metabolomic Analysis of Vitamin E Supplement Use in the Prostate, Lung, Colorectal, and Ovarian Cancer Screening Trial. Nutrients. 2023 Jun; 15(13):. doi: 10.3390/nu15132836. [PMID: 37447163]
  • Jiao Luo, Fleur L Meulmeester, Leon G Martens, Nadia Ashrafi, Renée de Mutsert, Dennis O Mook-Kanamori, Frits R Rosendaal, Ko Willems van Dijk, Saskia le Cessie, Kevin Mills, Raymond Noordam, Diana van Heemst. Urinary oxidized, but not enzymatic vitamin E metabolites are inversely associated with measures of glucose homeostasis in middle-aged healthy individuals. Clinical nutrition (Edinburgh, Scotland). 2021 06; 40(6):4192-4200. doi: 10.1016/j.clnu.2021.01.039. [PMID: 33593663]
  • Matthew J Kuchan, Katherine M Ranard, Priyankar Dey, Sookyoung Jeon, Geoff Y Sasaki, Karen J Schimpf, Richard S Bruno, Martha Neuringer, John W Erdman. Infant Rhesus Macaque Brain α-Tocopherol Stereoisomer Profile Is Differentially Impacted by the Source of α-Tocopherol in Infant Formula. The Journal of nutrition. 2020 09; 150(9):2305-2313. doi: 10.1093/jn/nxaa174. [PMID: 32614402]
  • Tomono Uchida, Saki Nomura, Hiroaki Oda, Saiko Ikeda. γ-Tocopherol Is Metabolized Faster than α-Tocopherol in Young Japanese Women. Journal of nutritional science and vitaminology. 2018; 64(6):399-403. doi: 10.3177/jnsv.64.399. [PMID: 30606962]
  • Sherry M Farley, Scott W Leonard, Edwin M Labut, Hannah F Raines, David J Card, Dominic J Harrington, Debbie J Mustacich, Maret G Traber. Vitamin E decreases extra-hepatic menaquinone-4 concentrations in rats fed menadione or phylloquinone. Molecular nutrition & food research. 2012 Jun; 56(6):912-22. doi: 10.1002/mnfr.201100751. [PMID: 22707266]
  • Eri Imai, Tomiko Tsuji, Mitsue Sano, Tsutomu Fukuwatari, Katsumi Shibata. Association between 24 hour urinary α-tocopherol catabolite, 2,5,7,8-tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman (α-CEHC) and α-tocopherol intake in intervention and cross-sectional studies. Asia Pacific journal of clinical nutrition. 2011; 20(4):507-13. doi: NULL. [PMID: 22094834]
  • Tomono Uchida, Saki Nomura, Tomio Ichikawa, Chisato Abe, Saiko Ikeda. Tissue distribution of vitamin E metabolites in rats after oral administration of tocopherol or tocotrienol. Journal of nutritional science and vitaminology. 2011; 57(5):326-32. doi: 10.3177/jnsv.57.326. [PMID: 22293209]
  • Michael W Clarke, John R Burnett, Jason H Y Wu, Jonathan M Hodgson, Thomas Ledowski, Ian B Puddey, Kevin D Croft. Vitamin E supplementation and hepatic drug metabolism in humans. Journal of cardiovascular pharmacology. 2009 Dec; 54(6):491-6. doi: 10.1097/fjc.0b013e3181bfae18. [PMID: 19755916]
  • Jan Frank, Trevor W George, John K Lodge, Ana M Rodriguez-Mateos, Jeremy P E Spencer, Anne Marie Minihane, Gerald Rimbach. Daily consumption of an aqueous green tea extract supplement does not impair liver function or alter cardiovascular disease risk biomarkers in healthy men. The Journal of nutrition. 2009 Jan; 139(1):58-62. doi: 10.3945/jn.108.096412. [PMID: 19056646]
  • Yi-Jen Li, Sheng-Ching Luo, Yi-Jing Lee, Fu-Jung Lin, Chi-Cheng Cheng, Yung-Shung Wein, Yueh-Hsiung Kuo, Ching-jang Huang. Isolation and identification of alpha-CEHC sulfate in rat urine and an improved method for the determination of conjugated alpha-CEHC. Journal of agricultural and food chemistry. 2008 Dec; 56(23):11105-13. doi: 10.1021/jf802459d. [PMID: 18991451]
  • Tomono Uchida, Tomio Ichikawa, Chisato Abe, Kanae Yamashita, Saiko Ikeda. Dietary sesame seed decreases urinary excretion of alpha- and gamma-tocopherol metabolites in rats. Journal of nutritional science and vitaminology. 2007 Aug; 53(4):372-6. doi: 10.3177/jnsv.53.372. [PMID: 17934245]
  • Chisato Abe, Tomono Uchida, Moeka Ohta, Tomio Ichikawa, Kanae Yamashita, Saiko Ikeda. Cytochrome P450-dependent metabolism of vitamin E isoforms is a critical determinant of their tissue concentrations in rats. Lipids. 2007 Jul; 42(7):637-45. doi: 10.1007/s11745-007-3064-2. [PMID: 17520307]
  • Yi-Jen Li, Huey-Mei Shaw. Pregnenolone and dexamethasone, modulators of cytochrome P450-3A, not increase but reduce urinary alpha-CEHC excretion in rats. BioFactors (Oxford, England). 2007; 31(1):67-76. doi: 10.1002/biof.5520310107. [PMID: 18806310]
  • Debbie J Mustacich, Richard S Bruno, Maret G Traber. Vitamin E. Vitamins and hormones. 2007; 76(?):1-21. doi: 10.1016/s0083-6729(07)76001-6. [PMID: 17628169]
  • S Yoshikawa, T Morinobu, K Hamamura, F Hirahara, T Iwamoto, H Tamai. The effect of gamma-tocopherol administration on alpha-tocopherol levels and metabolism in humans. European journal of clinical nutrition. 2005 Aug; 59(8):900-5. doi: 10.1038/sj.ejcn.1602154. [PMID: 15928686]
  • Richard S Bruno, Rajasekhar Ramakrishnan, Thomas J Montine, Tammy M Bray, Maret G Traber. {alpha}-Tocopherol disappearance is faster in cigarette smokers and is inversely related to their ascorbic acid status. The American journal of clinical nutrition. 2005 Jan; 81(1):95-103. doi: 10.1093/ajcn/81.1.95. [PMID: 15640466]
  • Regina Brigelius-Flohé, Johannes M Roob, Beate Tiran, Sandra Wuga, Josep Ribalta, Edmond Rock, Brigitte M Winklhofer-Roob. The effect of age on vitamin E status, metabolism, and function: metabolism as assessed by labeled tocopherols. Annals of the New York Academy of Sciences. 2004 Dec; 1031(?):40-3. doi: 10.1196/annals.1331.004. [PMID: 15753132]
  • Frank J Kelly, Rosalind Lee, Ian S Mudway. Inter- and intra-individual vitamin E uptake in healthy subjects is highly repeatable across a wide supplementation dose range. Annals of the New York Academy of Sciences. 2004 Dec; 1031(?):22-39. doi: 10.1196/annals.1331.003. [PMID: 15753131]
  • Francesco Galli, Marta Piroddi, Anna Lannone, Silvia Pagliarani, Aldo Tomasi, Ardesio Floridi. A comparison between the antioxidant and peroxynitrite-scavenging functions of the vitamin E metabolites alpha- and gamma-carboxyethyl-6-hydroxychromans. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2004 Sep; 74(5):362-73. doi: 10.1024/0300-9831.74.5.362. [PMID: 15628675]
  • Yvonne M Jeanes, Wendy L Hall, Anna R Proteggente, John K Lodge. Cigarette smokers have decreased lymphocyte and platelet alpha-tocopherol levels and increased excretion of the gamma-tocopherol metabolite gamma-carboxyethyl-hydroxychroman (gamma-CEHC). Free radical research. 2004 Aug; 38(8):861-8. doi: 10.1080/10715760410001715149. [PMID: 15493460]
  • T Morinobu, S Yoshikawa, K Hamamura, H Tamai. Measurement of vitamin E metabolites by high-performance liquid chromatography during high-dose administration of alpha-tocopherol. European journal of clinical nutrition. 2003 Mar; 57(3):410-4. doi: 10.1038/sj.ejcn.1601570. [PMID: 12627176]
  • Simon A S Pope, Guillaume E Burtin, Peter T Clayton, David J Madge, David P R Muller. Synthesis and analysis of conjugates of the major vitamin E metabolite, alpha-CEHC. Free radical biology & medicine. 2002 Sep; 33(6):807-17. doi: 10.1016/s0891-5849(02)00974-7. [PMID: 12208368]
  • Alejandro Betancor-Fernandez, Helmut Sies, Wilhelm Stahl, M Cristina Polidori. In vitro antioxidant activity of 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC), a vitamin E metabolite. Free radical research. 2002 Aug; 36(8):915-21. doi: 10.1080/1071576021000005357. [PMID: 12420750]
  • Dragan Radosavac, Peter Graf, M Cristina Polidori, Helmut Sies, Wilhelm Stahl. Tocopherol metabolites 2, 5, 7, 8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC) and 2, 7, 8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman (gamma-CEHC) in human serum after a single dose of natural vitamin E. European journal of nutrition. 2002 Jun; 41(3):119-24. doi: 10.1007/s00394-002-0365-3. [PMID: 12111049]
  • Francesco Galli, Rosalind Lee, Christina Dunster, Frank J Kelly. Gas chromatography mass spectrometry analysis of carboxyethyl-hydroxychroman metabolites of alpha- and gamma-tocopherol in human plasma. Free radical biology & medicine. 2002 Feb; 32(4):333-40. doi: 10.1016/s0891-5849(01)00800-0. [PMID: 11841923]
  • J K Lodge, J Ridlington, S Leonard, H Vaule, M G Traber. Alpha- and gamma-tocotrienols are metabolized to carboxyethyl-hydroxychroman derivatives and excreted in human urine. Lipids. 2001 Jan; 36(1):43-8. doi: 10.1007/s11745-001-0666-z. [PMID: 11214728]
  • M Schuelke, A Elsner, B Finckh, A Kohlschütter, C Hübner, R Brigelius-Flohé. Urinary alpha-tocopherol metabolites in alpha-tocopherol transfer protein-deficient patients. Journal of lipid research. 2000 Oct; 41(10):1543-51. doi: 10.1016/s0022-2275(20)31986-6. [PMID: 11013295]
  • S A Pope, P T Clayton, D P Muller. A new method for the analysis of urinary vitamin E metabolites and the tentative identification of a novel group of compounds. Archives of biochemistry and biophysics. 2000 Sep; 381(1):8-15. doi: 10.1006/abbi.2000.1950. [PMID: 11019814]
  • W Stahl, P Graf, R Brigelius-Flohé, W Wechter, H Sies. Quantification of the alpha- and gamma-tocopherol metabolites 2,5,7, 8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman and 2,7, 8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman in human serum. Analytical biochemistry. 1999 Nov; 275(2):254-9. doi: 10.1006/abio.1999.4312. [PMID: 10552913]
  • M G Traber, A Elsner, R Brigelius-Flohé. Synthetic as compared with natural vitamin E is preferentially excreted as alpha-CEHC in human urine: studies using deuterated alpha-tocopheryl acetates. FEBS letters. 1998 Oct; 437(1-2):145-8. doi: 10.1016/s0014-5793(98)01210-1. [PMID: 9804189]
  • M Schultz, M Leist, A Elsner, R Brigelius-Flohé. alpha-Carboxyethyl-6-hydroxychroman as urinary metabolite of vitamin E. Methods in enzymology. 1997; 282(?):297-310. doi: 10.1016/s0076-6879(97)82116-7. [PMID: 9330297]
  • M Schultz, M Leist, M Petrzika, B Gassmann, R Brigelius-Flohé. Novel urinary metabolite of alpha-tocopherol, 2,5,7,8-tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman, as an indicator of an adequate vitamin E supply?. The American journal of clinical nutrition. 1995 12; 62(6 Suppl):1527S-1534S. doi: 10.1093/ajcn/62.6.1527s. [PMID: 7495255]
  • A Schönfeld, M Schultz, M Petrizka, B Gassmann. A novel metabolite of RRR-alpha-tocopherol in human urine. Die Nahrung. 1993; 37(5):498-500. doi: 10.1002/food.19930370514. [PMID: 8259194]