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Human Metabolome Database Version 2.5

 

Showing metabocard for Dehydroascorbic acid (HMDB01264)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:37
Accession Number HMDB01264
Secondary Accession Numbers Not Available
Common Name Dehydroascorbic acid
Description Dehydroascorbic acid is the oxidized form of vitamin C. Reduced Vitamin C concentrations in the brain exceed those in blood by 10 fold. Dehydroascorbic acid readily enters the brain and is retained in the brain tissue in the form of ascorbic acid (ascorbic acid is not able to cross the blood-brain barrier). Therefore, transport of dehydroascorbic acid by the Glucose Transporter 1 (GLUT1, Glucose transporters are integral membrane glycoproteins involved in transporting glucose into most cells. GLUT1 is a major glucose transporter in the mammalian blood-brain barrier. It is present at high levels in primate erythrocytes and brain endothelial cells.) is a mechanism by which the brain acquires vitamin C. (OMIM 138140)
Synonyms
  1. 1-Dehydroascorbate
  2. 1-Dehydroascorbic acid
  3. DHAA
  4. Dehydro-L-ascorbate
  5. Dehydro-L-ascorbic acid
  6. Dehydroascorbate
  7. L-Dehydroascorbate
  8. L-Dehydroascorbic acid
  9. L-Threo-hexo-2,3-diulosono-1,4-lactone
  10. L-threo-2,3-Hexodiulosonic acid gamma-lactone
  11. Oxidized ascorbate
  12. Oxidized ascorbic acid
  13. Oxidized vitamin C
Chemical IUPAC Name 5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
Chemical Formula C6H6O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Monosaccharides
Family
  • Mammalian Metabolite
Species
  • ketone
  • primary alcohol
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid ester
  • lactone
  • heterocyclic compound
Biofunction
  • Component of Tyrosine metabolism
Application
—
Source
  • Endogenous
Average Molecular Weight 174.108
Monoisotopic Molecular Weight 174.016434
Isomeric SMILES OC[C@@H](O)[C@H]1OC(=O)C(=O)C1=O
Canonical SMILES OCC(O)C1OC(=O)C(=O)C1=O
KEGG Compound ID C00425 Link Image
BioCyc ID L-DEHYDRO-ASCORBATE Link Image
BiGG ID 34945 Link Image
Wikipedia Link Dehydroascorbic acid Link Image
NuGOwiki Link HMDB01264 Link Image
Metagene Link HMDB01264 Link Image
METLIN ID 342 Link Image
PubChem Compound 10280 Link Image
PubChem Substance 8157415 Link Image
ChEBI ID 17242 Link Image
CAS Registry Number 490-83-5
InChI Identifier InChI=1/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1
Synthesis Reference Utsumi, Isamu; Harada, Kiyoshi; Miura, Hiroshi. Dehydroascorbic acid. Jpn. Tokkyo Koho (1972), 2 pp.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 190.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.17 [Predicted by ALOGPS]; -1.9 [Predicted by PubChem via XLOGP]; -1.80 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location
  • Blood
Tissue Location
Tissue References
Blood —
Brain —
Erythrocyte —
Intestine —
Placenta —
Platelet —
Concentrations (Normal)
Biofluid Blood
Value 2.32 +/- 0.78 uM
Age Adult:>18 yrs old
Sex Both
Patient information Smoker
Comments Not Available
References
  • Lykkesfeldt J, Loft S, Nielsen JB, Poulsen HE: Ascorbic acid and dehydroascorbic acid as biomarkers of oxidative stress caused by smoking. Am J Clin Nutr. 1997 Apr;65(4):959-63. [PubMed Link Image]
Biofluid Blood
Value 2.36 +/- 0.11 uM
Age Adult:>18 yrs old
Sex Both
Patient information Non-smoker
Comments Not Available
References
  • Lykkesfeldt J, Loft S, Nielsen JB, Poulsen HE: Ascorbic acid and dehydroascorbic acid as biomarkers of oxidative stress caused by smoking. Am J Clin Nutr. 1997 Apr;65(4):959-63. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Catecholamine Biosynthesis SMP00012 Link Image map00350 Link Image
General References
  1. Raghavan SA, Sharma P, Dikshit M: Role of ascorbic acid in the modulation of inhibition of platelet aggregation by polymorphonuclear leukocytes. Thromb Res. 2003 May 1;110(2-3):117-26. [PubMed Link Image]
  2. Kuo SM, Tan D, Boyer JC: Cellular vitamin C accumulation in the presence of copper. Biol Trace Elem Res. 2004 Aug;100(2):125-36. [PubMed Link Image]
  3. Bakaev VV, Duntau AP: Ascorbic acid in blood serum of patients with pulmonary tuberculosis and pneumonia. Int J Tuberc Lung Dis. 2004 Feb;8(2):263-6. [PubMed Link Image]
  4. Toivola DM, Isomaa B: Effects of dehydroabietic acid on the erythrocyte membrane. Chem Biol Interact. 1991;79(1):65-78. [PubMed Link Image]
  5. Dhariwal KR, Hartzell WO, Levine M: Ascorbic acid and dehydroascorbic acid measurements in human plasma and serum. Am J Clin Nutr. 1991 Oct;54(4):712-6. [PubMed Link Image]
  6. Trepanier LA, Yoder AR, Bajad S, Beckwith MD, Bellehumeur JL, Graziano FM: Plasma ascorbate deficiency is associated with impaired reduction of sulfamethoxazole-nitroso in HIV infection. J Acquir Immune Defic Syndr. 2004 Aug 15;36(5):1041-50. [PubMed Link Image]
  7. Mendiratta S, Qu ZC, May JM: Erythrocyte ascorbate recycling: antioxidant effects in blood. Free Radic Biol Med. 1998 Mar 15;24(5):789-97. [PubMed Link Image]
  8. Padilla CA, Spyrou G, Holmgren A: High-level expression of fully active human glutaredoxin (thioltransferase) in E. coli and characterization of Cys7 to Ser mutant protein. FEBS Lett. 1996 Jan 2;378(1):69-73. [PubMed Link Image]
  9. Shugalei IuS, Degtiar VV, Butvin IN, Grivenko GP: [Effect of alcohol intoxication on ascorbic and dehydroascorbic acid levels in rat tissue. and human blood] Ukr Biokhim Zh. 1986 May-Jun;58(3):81-3. [PubMed Link Image]
  10. Bakaev VV, Efremov AV, Tityaev II: Low levels of dehydroascorbic acid in uraemic serum and the partial correction of dehydroascorbic acid deficiency by haemodialysis. Nephrol Dial Transplant. 1999 Jun;14(6):1472-4. [PubMed Link Image]
  11. Margolis SA, Ziegler RG, Helzlsouer KJ: Ascorbic and dehydroascorbic acid measurement in human serum and plasma. Am J Clin Nutr. 1991 Dec;54(6 Suppl):1315S-1318S. [PubMed Link Image]
  12. Davis JL Jr, Mendiratta S, May JM: Similarities in the metabolism of alloxan and dehydroascorbate in human erythrocytes. Biochem Pharmacol. 1998 Apr 15;55(8):1301-7. [PubMed Link Image]
  13. Wells WW, Xu DP, Yang YF, Rocque PA: Mammalian thioltransferase (glutaredoxin) and protein disulfide isomerase have dehydroascorbate reductase activity. J Biol Chem. 1990 Sep 15;265(26):15361-4. [PubMed Link Image]
  14. Dubey SS, Palodhi GR, Jain AK: Ascorbic acid, dehydroascorbic acid and glutathione in liver disease. Indian J Physiol Pharmacol. 1987 Oct-Dec;31(4):279-83. [PubMed Link Image]
  15. May JM, Qu ZC, Whitesell RR, Cobb CE: Ascorbate recycling in human erythrocytes: role of GSH in reducing dehydroascorbate. Free Radic Biol Med. 1996;20(4):543-51. [PubMed Link Image]
  16. Wikipedia Link Image