Diketogulonic acid (BioDeep_00000005573)

 

Secondary id: BioDeep_00000014568, BioDeep_00000629080, BioDeep_00001869720

human metabolite Endogenous


代谢物信息卡片


(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoic acid

化学式: C6H8O7 (192.0270018)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.24%

分子结构信息

SMILES: C(C(C(C(=O)C(=O)C(=O)O)O)O)O
InChI: InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)

描述信息

Diketogulonic acid (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20\\% of the vitamin C by-products (oxalate being approximately 44\\% and dehydroascorbate 20\\%). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy. (PMID: 16698813, 17222174)

同义名列表

31 个代谢物同义名

(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoic acid; (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid; (4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoate; (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate; 2,3-dioxo-4R,5S,6-trihydroxy-hexanoic acid; 2,3-Dioxo-2,3-dideoxy-L-gulonic acid; L-Threo-(2,3)-hexodiulosonsaeure; L-Threo-hexo-2,3-diulosonic acid; 2,3-Dioxo-2,3-dideoxy-L-gulonate; L-Threo-2,3-hexodiulosonic acid; L-Threo-2,3-hexodiurosonic acid; Threo-2,3-hexodiulosonic acid; L-Threo-2,3-hexodiurosonate; Threo-2,3-hexodiulosonate; 2,3-diketo-L Gulonic acid; 2,3-Diketo-L-gulonic acid; 2,3-L-Diketogulonic acid; Acid, 2,3-diketogulonic; 2,3-Diketogulonic Acid; 2,3 Diketogulonic acid; 2,3-Diketo-L-gulonate; Diketo-L-gulonic acid; 2,3-Dioxo-D-gulonate; 2,3-L-Diketogulonate; diketo-gulonic acid; 2,3-Dioxo-L-gulonic; Diketogulonic acid; 2,3-Diketogulonate; Diketo-L-gulonate; Diketo-gulonate; Diketogulonate



数据库引用编号

17 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)

2 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

  • Rebecca A Dewhirst, Lorna Murray, C Logan Mackay, Ian H Sadler, Stephen C Fry. Characterisation of the non-oxidative degradation pathway of dehydroascorbic acid in slightly acidic aqueous solution. Archives of biochemistry and biophysics. 2020 03; 681(?):108240. doi: 10.1016/j.abb.2019.108240. [PMID: 31883928]
  • Rebecca A Dewhirst, Stephen C Fry. The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species. The Biochemical journal. 2018 11; 475(21):3451-3470. doi: 10.1042/bcj20180688. [PMID: 30348642]
  • Anna Kärkönen, Rebecca A Dewhirst, C Logan Mackay, Stephen C Fry. Metabolites of 2,3-diketogulonate delay peroxidase action and induce non-enzymic H2O2 generation: Potential roles in the plant cell wall. Archives of biochemistry and biophysics. 2017 04; 620(?):12-22. doi: 10.1016/j.abb.2017.03.006. [PMID: 28315301]
  • E A Elewa, M A El Tokhy, S E Fathy, A M Talaat. Predictive role of urinary neutrophil gelatinase-associated lipocalin in lupus nephritis. Lupus. 2015 Feb; 24(2):138-46. doi: 10.1177/0961203314550225. [PMID: 25199807]
  • Harriet T Parsons, Stephen C Fry. Oxidation of dehydroascorbic acid and 2,3-diketogulonate under plant apoplastic conditions. Phytochemistry. 2012 Mar; 75(?):41-9. doi: 10.1016/j.phytochem.2011.12.005. [PMID: 22226246]
  • Anna Kärkönen, Stephen C Fry. Effect of ascorbate and its oxidation products on H2O2 production in cell-suspension cultures of Picea abies and in the absence of cells. Journal of experimental botany. 2006; 57(8):1633-44. doi: 10.1093/jxb/erj197. [PMID: 16698813]
  • Hiroko Hirano, Yoshinori Tone, Haruhisa Otani, Masaki Oya, Keigo Kimura, Yasushi Saika, Ryoichi Fujii, Masatoshi Mune, Masakazu Ichinose, Susumu Yukawa. [Levels of serum ascorbate and its metabolites in hemodialysis patients]. Nihon Jinzo Gakkai shi. 2004 Jul; 46(5):426-33. doi: NULL. [PMID: 15446598]
  • V V Bakaev, A P Duntau. Ascorbic acid in blood serum of patients with pulmonary tuberculosis and pneumonia. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. 2004 Feb; 8(2):263-6. doi: . [PMID: 15139458]
  • Yoko Nishikawa, Barbara Dmochowska, Janusz Madaj, Jie Xue, Zhongwu Guo, Makoto Satake, D Venkat Reddy, Peter L Rinaldi, Vincent M Monnier. Vitamin C metabolomic mapping in experimental diabetes with 6-deoxy-6-fluoro-ascorbic acid and high resolution 19F-nuclear magnetic resonance spectroscopy. Metabolism: clinical and experimental. 2003 Jun; 52(6):760-70. doi: 10.1016/s0026-0495(03)00069-6. [PMID: 12800104]
  • N Dwivedi, M Das, S K Khanna. Role of biological antioxidants in benzanthrone toxicity. Archives of toxicology. 2001 Jun; 75(4):221-6. doi: 10.1007/s002040100222. [PMID: 11482520]
  • V V Bakaev, A V Efremov. [The excretion of ascorbic acid and its metabolites in uremia and hemodialysis]. Patologicheskaia fiziologiia i eksperimental'naia terapiia. 2000 Apr; ?(2):22-4. doi: . [PMID: 10846906]
  • I Koshiishi, Y Mamura, J Liu, T Imanari. Degradation of dehydroascorbate to 2,3-diketogulonate in blood circulation. Biochimica et biophysica acta. 1998 Sep; 1425(1):209-14. doi: 10.1016/s0304-4165(98)00073-7. [PMID: 9813330]
  • M M Rasulov, I G Kuznetsov, A G Zabozlaev, M G Voronkov. [Oxyferriscorbone: anti-ulcer effect and its possible mechanisms]. Biulleten' eksperimental'noi biologii i meditsiny. 1994 May; 117(5):490-3. doi: ". [PMID: 9296698]
  • V V Bakaev, V F Khomenko, I I Titiaev. [Vitamin K1 and C excretion by the kidneys in chronic kidney failure]. Urologiia i nefrologiia. 1993 Nov; ?(6):42-4. doi: NULL. [PMID: 8160321]
  • P Dostert, M S Benedetti, E Frigerio. Effect of L-dopa, oxyferriscorbone and ferrous iron on in vivo lipid peroxidation. Journal of neural transmission. General section. 1991; 84(1-2):119-28. doi: 10.1007/bf01249115. [PMID: 2054143]
  • M M Rasulov, I G Kuznetsov, S K Suslova, M V Velikaia, M G Voronkov. [Possible mechanisms of anti-ulcer action of silatranes]. Biulleten' eksperimental'noi biologii i meditsiny. 1990 Sep; 110(9):249-52. doi: ". [PMID: 2268706]
  • M Takagi, A Kawajiri, K Nakata, N Morita. Behavior of 3,4-endiol form of 2,3-diketo-gulono-delta-lactone formed from dehydro-L-ascorbic acid in deoxygenated and neutral solution. Journal of nutritional science and vitaminology. 1989 Feb; 35(1):61-70. doi: 10.3177/jnsv.35.61. [PMID: 2738715]
  • B M Kliachkin, S T Basargin, A N Glushkov, A A Korostelev, I A Klimov. [Mechanism of formation of blocking factors and method of antiblocking immunotherapy in malignant tumors]. Voprosy onkologii. 1985; 31(2):78-84. doi: NULL. [PMID: 3883653]
  • S G Vaĭnshteĭn, F A Zvershkhanovskiĭ. [Lipid peroxidation in patients with gastric ulcer and cancer]. Voprosy onkologii. 1984; 30(10):39-41. doi: . [PMID: 6495681]
  • K Schmidt, H Oberritter, G Bruchelt, V Hagmaier, D Hornig. Studies on the metabolic conversion of ascorbate. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1983; 53(1):77-85. doi: . [PMID: 6406384]
  • N G Pushina. [Relation between ascorbic acid metabolism and the body' supply of vitamin K]. Voprosy pitaniia. 1982 May; ?(3):36-42. doi: NULL. [PMID: 7113100]
  • J E Davies, R E Hughes, E Jones, S E Reed, J W Craig, D A Tyrrell. Metabolism of ascorbic acid (vitamin C) in subjects infected with common cold viruses. Biochemical medicine. 1979 Feb; 21(1):78-85. doi: 10.1016/0006-2944(79)90058-9. [PMID: 222262]
  • E Zvetkova, S G Koschucharoff, A I Hadjioloff. Cytochemistry of nucleoproteids and some cathionic proteins in the peripheral blood leukocytes of patients with lung cancer. Folia haematologica (Leipzig, Germany : 1928). 1979; 106(2):205-23. doi: NULL. [PMID: 91557]
  • B Nambisan, P A Kurup. Ascorbic acid metabolism in rats fed high fat cholesterol diet. Atherosclerosis. 1976 Oct; 25(1):63-9. doi: 10.1016/0021-9150(76)90048-4. [PMID: 985599]
  • B D Cox, M J Whichelow. The measurement of dehydroascorbic acid and diketogulonic acid in normal and diabetic plasma. Biochemical medicine. 1975 Feb; 12(2):183-93. doi: 10.1016/0006-2944(75)90110-6. [PMID: 1137579]
  • J P Poisson. [Metabolism of L-ascorbic, L-dehydroascorbic and 2,3-diketo-L-gulonic acids during a short duration fast in guinea pigs]. Annales de la nutrition et de l'alimentation. 1975; 29(2):117-36. doi: NULL. [PMID: 1190642]
  • . . . . doi: . [PMID: 21846329]