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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:15:27 UTC
HMDB IDHMDB0001264
Secondary Accession Numbers
  • HMDB01264
Metabolite Identification
Common NameDehydroascorbic acid
DescriptionDehydroascorbic 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 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 acid's 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.
Structure
Data?1592928040
Synonyms
ValueSource
Dehydro-L-ascorbic acidChEBI
Dehydroascorbic acidChEBI
DHAAChEBI
L-DehydroascorbateChEBI
L-threo-2,3-Hexodiulosonic acid, gamma-lactoneChEBI
L-threo-hexo-2,3-diulosono-1,4-LactoneChEBI
Oxidized ascorbic acidChEBI
Oxidized vitamin CChEBI
Dehydro-L-ascorbateGenerator
DehydroascorbateGenerator
L-threo-2,3-Hexodiulosonate, g-lactoneGenerator
L-threo-2,3-Hexodiulosonate, gamma-lactoneGenerator
L-threo-2,3-Hexodiulosonate, γ-lactoneGenerator
L-threo-2,3-Hexodiulosonic acid, g-lactoneGenerator
L-threo-2,3-Hexodiulosonic acid, γ-lactoneGenerator
Oxidized ascorbateGenerator
Acid, dehydroascorbicMeSH
L-Dehydro-ascorbateHMDB
L-Dehydroascorbic acidHMDB
L-threo-Dehydroascorbic acidHMDB
Chemical FormulaC6H6O6
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional NameDHAA
CAS Registry Number490-83-5
SMILES
[H][C@@]1(OC(=O)C(=O)C1=O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
InChI KeySBJKKFFYIZUCET-JLAZNSOCSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • 3-furanone
  • Gamma butyrolactone
  • Tetrahydrofuran
  • 1,2-diol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility190 g/LALOGPS
logP-1.2ALOGPS
logP-0.67ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.55 m³·mol⁻¹ChemAxon
Polarizability14.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05fr-1910000000-637a588dd38c4cc58ae5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fs-1910000000-194039de8a412e640d7fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fs-1900000000-af0738c9bda7200b8742Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08iu-9200000000-bbb79c0fcf383789f477Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-4900000000-25a652482451303b3ca4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-1900000000-c546ba0f061c1d25a934Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0mbc-2900000000-254c596333e32143329fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-9700000000-a77d2c857a58b59513ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-c9ba5aa4017d618b9908Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-52e4a1b574cf41140928Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-e89ff5aa246bed40fed2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Blood
  • Brain
  • Erythrocyte
  • Intestine
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.32 +/- 0.78 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.36 +/- 0.11 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified12.636 +/- 5.744 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.72-7.47 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.1 (5.8-7.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08830
Phenol Explorer Compound IDNot Available
FooDB IDFDB011907
KNApSAcK IDC00007380
Chemspider ID389547
KEGG Compound IDC05422
BioCyc IDL-DEHYDRO-ASCORBATE
BiGG IDNot Available
Wikipedia LinkDehydroascorbic acid
METLIN ID342
PubChem Compound440667
PDB IDNot Available
ChEBI ID27956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceUtsumi, Isamu; Harada, Kiyoshi; Miura, Hiroshi. Dehydroascorbic acid. Jpn. Tokkyo Koho (1972), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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:12893026 ]
  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:15326362 ]
  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:15139458 ]
  4. Toivola DM, Isomaa B: Effects of dehydroabietic acid on the erythrocyte membrane. Chem Biol Interact. 1991;79(1):65-78. [PubMed:2060038 ]
  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:1897478 ]
  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:15247557 ]
  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:9586809 ]
  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:8549805 ]
  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 (1978). 1986 May-Jun;58(3):81-3. [PubMed:3727042 ]
  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:10383010 ]
  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:1962589 ]
  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:9719486 ]
  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:2394726 ]
  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:3450633 ]
  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:8904295 ]
  16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:
PAM
Uniprot ID:
P19021
Molecular weight:
108402.425
Reactions
Peptidylglycine + Ascorbic acid + Oxygen → peptidyl(2-hydroxyglycine) + Dehydroascorbic acid + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
Reactions
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
Glutathione + Dehydroascorbic acid → Oxidized glutathione + Ascorbic aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase activity. Has high dehydroascorbate reductase activity and may contribute to the recycling of ascorbic acid. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA).
Gene Name:
GSTO2
Uniprot ID:
Q9H4Y5
Molecular weight:
24399.09
Reactions
Glutathione + Dehydroascorbic acid → Oxidized glutathione + Ascorbic aciddetails