Dehydroascorbic acid (BioDeep_00000003220)

 

Secondary id: BioDeep_00000265303, BioDeep_00000405431

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs BioNovoGene_Lab2019 natural product


代谢物信息卡片


(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

化学式: C6H6O6 (174.0164)
中文名称: (L)-脱氢抗坏血酸++, 脱氢抗坏血酸
谱图信息: 最多检出来源 Homo sapiens(blood) 21.65%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Dehydroascorbic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dehydroascorbic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000003220). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C(C1C(=O)C(=O)C(=O)O1)O)O
InChI: InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2

描述信息

Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. Dehydroascorbic acid, also known as L-dehydroascorbate or DHAA, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid has similar biological activity as ascorbic acid. Currently dehydroascorbic acid is an experimental drug with no known approved indications. Dehydroascorbic acid may be a unique E. coli metabolite. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In humans, dehydroascorbic acid is involved in the metabolic disorder called tyrosinemia type I. Concerning dehydroascorbic acids antiviral effect against herpes simplex virus type 1, it is suggested that dehydroascorbic acid acts after replication of viral DNA and prevents the assembly of progeny virus particles. This is important because one study has found that after an ischemic stroke, dehydroascorbic acid has neuroprotective effects by reducing infarct volume, neurological deficits, and mortality. This reaction is reversible, but dehydroascorbic acid can instead undergo irreversible hydrolysis to 2,3-diketogulonic acid. In addition, unlike ascorbic Dehydroascorbic acid acid can cross the blood brain barrier and is then converted to ascorbic acid to enable retention in the brain. Dehydroascorbic acid is made from the oxidation of ascorbic acid. The exact mechanism of action is still being investigated, but some have been elucidated. Both compounds have been shown to have antiviral effects against herpes simplex virus type 1, influenza virus type A and poliovirus type 1 with dehydroascorbic acid having the stronger effect. In the body, both dehydroascorbic acid and ascorbic acid have similar biological activity as antivirals but dehydroascorbic acid also has neuroprotective effects. Even though dehydroascorbic acid and ascorbic acid have similar effects, their mechanism of action seems to be different.
Dehydroascorbic acid, also known as dehydroascorbate, is a member of the class of compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Dehydroascorbic acid can be found in a number of food items such as white cabbage, gram bean, mexican groundcherry, and common pea, which makes dehydroascorbic acid a potential biomarker for the consumption of these food products. Dehydroascorbic acid may be a unique E.coli metabolite. Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids .
D018977 - Micronutrients > D014815 - Vitamins
Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.
Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.

同义名列表

23 个代谢物同义名

(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione; L-threo-2,3-Hexodiulosonic acid, gamma-lactone; 5-(1,2-Dihydroxyethyl)-2,3,4(5H)-furantrione; L-threo-2,3-Hexodiulosonic acid, γ-lactone; L-threo-2,3-Hexodiulosonate, gamma-lactone; L-threo-2,3-Hexodiulosonic acid, g-lactone; L-threo-2,3-Hexodiulosonate, γ-lactone; L-threo-2,3-Hexodiulosonate, g-lactone; L-threo-hexo-2,3-diulosono-1,4-Lactone; L-threo-Dehydroascorbic acid; Dehydro-L-ascorbic acid; L-Dehydroascorbic acid; Oxidized ascorbic acid; Acid, dehydroascorbic; Dehydroascorbic acid; Dehydro-L-ascorbate; L-Dehydro-ascorbate; Oxidized vitamin C; Oxidized ascorbate; L-Dehydroascorbate; Dehydroascorbate; DHAA; Dehydroascorbate



数据库引用编号

23 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(0)

代谢反应

12 个相关的代谢反应过程信息。

Reactome(7)

BioCyc(1)

WikiPathways(2)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • Ascorbate Metabolism: Ascorbic acid + Hydrogen Ion + Hydrogen peroxide ⟶ Ascorbic acid + Dehydroascorbic acid + Water

PharmGKB(0)

53 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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 BCL2, CASP3, CAT, G6PD, HPGDS, SLC23A1, SLC23A2, SLC2A10, SLC2A2, TXN
Peripheral membrane protein 2 G6PD, HSD17B6
Endosome membrane 1 TF
Endoplasmic reticulum membrane 2 BCL2, HSP90B1
Nucleus 5 BCL2, CASP3, GLRX, HSP90B1, TXN
cytosol 12 BCL2, CASP3, CAT, G6PD, GLRX, GSR, HPGDS, HSP90B1, SLC2A1, SLC2A10, SLC2A4, TXN
trans-Golgi network 1 SLC2A4
nucleoplasm 3 CASP3, HPGDS, TXN
Cell membrane 7 SLC23A1, SLC23A2, SLC2A1, SLC2A2, SLC2A3, SLC2A4, SLC2A5
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 8 SLC23A1, SLC23A2, SLC2A1, SLC2A10, SLC2A2, SLC2A3, SLC2A4, SLC2A5
cell surface 1 TF
glutamatergic synapse 1 CASP3
Golgi membrane 2 INS, SLC2A1
neuronal cell body 1 CASP3
sarcolemma 3 SLC2A1, SLC2A4, SLC2A5
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 G6PD
Presynapse 2 SLC2A1, SLC2A4
plasma membrane 9 SLC23A1, SLC23A2, SLC2A1, SLC2A10, SLC2A2, SLC2A3, SLC2A4, SLC2A5, TF
Membrane 11 BCL2, CAT, G6PD, HSP90B1, SLC23A1, SLC23A2, SLC2A1, SLC2A10, SLC2A2, SLC2A3, SLC2A4
apical plasma membrane 6 SLC23A1, SLC23A2, SLC2A1, SLC2A2, SLC2A5, TF
basolateral plasma membrane 3 SLC23A1, SLC23A2, SLC2A1
brush border 1 SLC2A2
caveola 1 SLC2A1
extracellular exosome 12 CAT, G6PD, GLRX, GSR, HSP90B1, SLC23A1, SLC2A1, SLC2A3, SLC2A4, SLC2A5, TF, TXN
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 BCL2, HSD17B6, HSP90B1
extracellular space 2 INS, TF
perinuclear region of cytoplasm 4 HSP90B1, SLC2A10, SLC2A4, TF
intercalated disc 1 SLC2A1
mitochondrion 3 BCL2, CAT, GSR
protein-containing complex 3 BCL2, CAT, HSP90B1
intracellular membrane-bounded organelle 4 CAT, G6PD, HPGDS, HSD17B6
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Secreted 3 INS, TF, TXN
extracellular region 5 CAT, HSP90B1, INS, TF, TXN
cytoplasmic side of plasma membrane 1 G6PD
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
basal part of cell 1 TF
mitochondrial matrix 2 CAT, GSR
centriolar satellite 1 G6PD
photoreceptor inner segment 1 SLC2A1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 GSR, SLC2A4
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
perikaryon 1 SLC2A3
Z disc 1 SLC2A1
cytoplasmic vesicle 1 TF
midbody 2 HSP90B1, SLC2A1
Early endosome 1 TF
cell-cell junction 1 SLC2A2
clathrin-coated pit 2 SLC2A4, TF
recycling endosome 1 TF
vesicle 1 TF
Apical cell membrane 1 SLC2A5
Cell membrane, sarcolemma 1 SLC2A5
Cytoplasm, perinuclear region 2 SLC2A10, SLC2A4
Membrane raft 1 SLC2A4
pore complex 1 BCL2
focal adhesion 2 CAT, HSP90B1
Peroxisome 1 CAT
sarcoplasmic reticulum 1 SLC2A4
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 HSP90B1
Late endosome 1 TF
cell projection 1 SLC2A3
blood microparticle 2 SLC2A1, TF
Endomembrane system 2 SLC2A10, SLC2A4
endosome lumen 1 INS
female germ cell nucleus 1 SLC2A1
Cytoplasmic vesicle membrane 1 SLC2A4
specific granule membrane 2 SLC2A3, SLC2A5
tertiary granule membrane 1 SLC2A3
Melanosome 2 HSP90B1, SLC2A1
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
basal plasma membrane 3 SLC23A1, SLC23A2, TF
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 3 CAT, INS, TF
HFE-transferrin receptor complex 1 TF
secretory granule membrane 1 SLC2A3
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 HSP90B1, INS, TF
cortical actin cytoskeleton 1 SLC2A1
endocytic vesicle 1 TF
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
aggresome 1 SLC2A3
vesicle membrane 1 SLC2A4
clathrin-coated endocytic vesicle membrane 1 TF
Sarcoplasmic reticulum lumen 1 HSP90B1
ficolin-1-rich granule membrane 1 SLC2A3
death-inducing signaling complex 1 CASP3
female pronucleus 1 SLC2A1
vesicle coat 1 TF
endocytic vesicle lumen 1 HSP90B1
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
BAD-BCL-2 complex 1 BCL2
glucose transporter complex 1 SLC2A1
intracellular organelle 1 SLC23A1
insulin-responsive compartment 1 SLC2A4
dense body 1 TF


文献列表

  • Luciano Ferrada, María José Barahona, Matías Vera, Brent R Stockwell, Francisco Nualart. Dehydroascorbic acid sensitizes cancer cells to system xc- inhibition-induced ferroptosis by promoting lipid droplet peroxidation. Cell death & disease. 2023 09; 14(9):637. doi: 10.1038/s41419-023-06153-9. [PMID: 37752118]
  • Kirti Shila Sonkar, V Mohan Murali Achary, Sibasis Sahoo, Malireddy K Reddy, Arulandu Arockiasamy. Biochemical and structural characterization of a robust and thermostable ascorbate recycling monodehydroascorbate reductase (MDHAR) from stress adapted pearl millet. Biochemical and biophysical research communications. 2023 Jun; 662(?):135-141. doi: 10.1016/j.bbrc.2023.04.034. [PMID: 37119729]
  • Nibin Shi, Xin Yan, Adeyemi S Adeleye, Xuxiang Zhang, Dongmei Zhou, Lijuan Zhao. Effects of WS2 Nanosheets on N2-fixing Cyanobacteria: ROS overproduction, cell membrane damage, and cell metabolic reprogramming. The Science of the total environment. 2022 Nov; 849(?):157706. doi: 10.1016/j.scitotenv.2022.157706. [PMID: 35908696]
  • Si Long, Bowen Liu, Jiongjiong Gong, Ruijia Wang, Shuanghong Gao, Tianqi Zhu, Huan Guo, Tieyuan Liu, Yuefei Xu. 5-Aminolevulinic acid promotes low-light tolerance by regulating chloroplast ultrastructure, photosynthesis, and antioxidant capacity in tall fescue. Plant physiology and biochemistry : PPB. 2022 Nov; 190(?):248-261. doi: 10.1016/j.plaphy.2022.09.010. [PMID: 36152510]
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  • Yasumasa Okazaki, Yuuri Ishidzu, Fumiya Ito, Hiromasa Tanaka, Masaru Hori, Shinya Toyokuni. L-Dehydroascorbate efficiently degrades non-thermal plasma-induced hydrogen peroxide. Archives of biochemistry and biophysics. 2021 03; 700(?):108762. doi: 10.1016/j.abb.2021.108762. [PMID: 33482147]
  • Fahimeh Kalbkhani, Ali Pirnejad, Sohrab Sam, Mohammad Reza Sam. The Safe Soluble Compound Dehydroascorbic Acid Inhibits Various Upstream and Downstream Effectors of PI3K and KRAS Signaling Pathways in Undruggable PIK3CA/KRAS-Mutant Colorectal Cancer Stem-Like Cells. Nutrition and cancer. 2021; 73(11-12):2654-2664. doi: 10.1080/01635581.2020.1856387. [PMID: 33283545]
  • Katherine Forman, Fernando Martínez, Manuel Cifuentes, Marcos Fernández, Romina Bertinat, Pablo Torres, Katterine Salazar, Alejandro Godoy, Francisco Nualart. Dehydroascorbic acid, the oxidized form of vitamin C, improves renal histology and function in old mice. Journal of cellular physiology. 2020 12; 235(12):9773-9784. doi: 10.1002/jcp.29791. [PMID: 32437012]
  • Robert Root-Bernstein, Beth Churchill, Miah Turke. Glutathione and Glutathione-Like Sequences of Opioid and Aminergic Receptors Bind Ascorbic Acid, Adrenergic and Opioid Drugs Mediating Antioxidant Function: Relevance for Anesthesia and Abuse. International journal of molecular sciences. 2020 Aug; 21(17):. doi: 10.3390/ijms21176230. [PMID: 32872204]
  • Tae Yoon Kim, Hara Ku, Seung-Yop Lee. Crop Enhancement of Cucumber Plants under Heat Stress by Shungite Carbon. International journal of molecular sciences. 2020 Jul; 21(14):. doi: 10.3390/ijms21144858. [PMID: 32659984]
  • 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]
  • Daniel Maynard, Vijay Kumar, Jens Sproï, Karl-Josef Dietz. 12-Oxophytodienoic Acid Reductase 3 (OPR3) Functions as NADPH-Dependent α,β-Ketoalkene Reductase in Detoxification and Monodehydroascorbate Reductase in Redox Homeostasis. Plant & cell physiology. 2020 Mar; 61(3):584-595. doi: 10.1093/pcp/pcz226. [PMID: 31834385]
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  • Yasumasa Okazaki, Hiromasa Tanaka, Masaru Hori, Shinya Toyokuni. l-Dehydroascorbic acid recycled by thiols efficiently scavenges non-thermal plasma-induced hydroxyl radicals. Archives of biochemistry and biophysics. 2019 07; 669(?):87-95. doi: 10.1016/j.abb.2019.05.019. [PMID: 31153952]
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  • Nieves Baenas, Francisco J Salar, Raúl Domínguez-Perles, Cristina García-Viguera. New UHPLC-QqQ-MS/MS Method for the Rapid and Sensitive Analysis of Ascorbic and Dehydroascorbic Acids in Plant Foods. Molecules (Basel, Switzerland). 2019 Apr; 24(8):. doi: 10.3390/molecules24081632. [PMID: 31027237]
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