Dehydroascorbic Acid

Identification

Name
Dehydroascorbic Acid
Accession Number
DB08830
Type
Small Molecule
Groups
Experimental
Description

Dehydroascorbic acid is made from the oxidation of ascorbic acid. This reaction is reversible, but dehydroascorbic acid can instead undergo irreversible hydrolysis to 2,3-diketogulonic acid. Dehydroascorbic acid as well as ascorbic acid are both termed Vitamin C, but the latter is the main form found in humans. In the body, both dehydroascorbic acid and ascorbic acid have similar biological activity as antivirals but dehydroascorbic acid also has neuroprotective effects. Currently dehydroascorbic acid is an experimental drug with no known approved indications.

Structure
Thumb
Synonyms
  • dehydro-L-ascorbic acid
  • DHAA
  • L-dehydroascorbate
  • L-dehydroascorbic acid
  • L-threo-2,3-hexodiulosonic acid, γ-lactone
  • L-threo-hexo-2,3-diulosono-1,4-lactone
  • oxidized ascorbic acid
  • oxidized vitamin C
Categories
UNII
Y2Z3ZTP9UM
CAS number
490-83-5
Weight
Average: 174.1082
Monoisotopic: 174.016437924
Chemical Formula
C6H6O6
InChI Key
SBJKKFFYIZUCET-JLAZNSOCSA-N
InChI
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
IUPAC Name
(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
SMILES
[H][[email protected]](O)(CO)[[email protected]@]1([H])OC(=O)C(=O)C1=O

Pharmacology

Indication

There is no approved indication for dehydroascorbic acid, but it has potential therapeutic use in patients with certain viruses and ischemic stroke.

Structured Indications
Not Available
Pharmacodynamics

Dehydroascorbic acid has similar biological activity as ascorbic acid. 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 addition, unlike ascorbic acid, dehydroascorbic acid can cross the blood brain barrier and is then converted to ascorbic acid to enable retention in the brain. 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.

Mechanism of action

Even though dehydroascorbic acid and ascorbic acid have similar effects, their mechanism of action seems to be different. The exact mechanism of action is still being investigated, but some have been elucidated. 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.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Agus DB, Gambhir SS, Pardridge WM, Spielholz C, Baselga J, Vera JC, Golde DW: Vitamin C crosses the blood-brain barrier in the oxidized form through the glucose transporters. J Clin Invest. 1997 Dec 1;100(11):2842-8. [PubMed:9389750]
  2. Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, Choudhri TF, Kim LJ, Mocco J, Pinsky DJ, Fox WD, Israel RJ, Boyd TA, Golde DW, Connolly ES Jr: Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4. [PubMed:11573006]
  3. Furuya A, Uozaki M, Yamasaki H, Arakawa T, Arita M, Koyama AH: Antiviral effects of ascorbic and dehydroascorbic acids in vitro. Int J Mol Med. 2008 Oct;22(4):541-5. [PubMed:18813862]
External Links
KEGG Compound
C05422
PubChem Compound
440667
PubChem Substance
175427110
ChemSpider
389547
ChEBI
27956
HET
UU3
Wikipedia
Dehydroascorbic_acid
PDB Entries
5mye
MSDS
Download (46.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)Decomposes at 225°C (437°F)From MSDS.
water solubilitySoluble in water at 60°CFrom The Merck Index.
pKa3.90From The Merck Index.
Predicted Properties
PropertyValueSource
Water Solubility190.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.55 m3·mol-1ChemAxon
Polarizability14.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7263
Blood Brain Barrier+0.8746
Caco-2 permeable-0.7901
P-glycoprotein substrateNon-substrate0.7062
P-glycoprotein inhibitor INon-inhibitor0.8824
P-glycoprotein inhibitor IINon-inhibitor0.9492
Renal organic cation transporterNon-inhibitor0.9146
CYP450 2C9 substrateNon-substrate0.8574
CYP450 2D6 substrateNon-substrate0.8789
CYP450 3A4 substrateNon-substrate0.7245
CYP450 1A2 substrateNon-inhibitor0.9302
CYP450 2C9 inhibitorNon-inhibitor0.9737
CYP450 2D6 inhibitorNon-inhibitor0.9608
CYP450 2C19 inhibitorNon-inhibitor0.9683
CYP450 3A4 inhibitorNon-inhibitor0.9769
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9906
Ames testNon AMES toxic0.9225
CarcinogenicityNon-carcinogens0.9203
BiodegradationReady biodegradable0.9583
Rat acute toxicity1.0981 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9766
hERG inhibition (predictor II)Non-inhibitor0.956
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-05fr-1910000000-637a588dd38c4cc58ae5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fs-1910000000-194039de8a412e640d7f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fs-1900000000-af0738c9bda7200b8742
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma butyrolactones. These 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactones
Sub Class
Gamma butyrolactones
Direct Parent
Gamma butyrolactones
Alternative Parents
Furanones / Tetrahydrofurans / Secondary alcohols / Cyclic ketones / Carboxylic acid esters / 1,2-diols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides
show 1 more
Substituents
3-furanone / Gamma butyrolactone / Tetrahydrofuran / 1,2-diol / Carboxylic acid ester / Cyclic ketone / Secondary alcohol / Ketone / Carboxylic acid derivative / Oxacycle
show 9 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
dehydroascorbic acid (CHEBI:27956)

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Xenobiotic transporter activity
Specific Function
Facilitative glucose transporter. This isoform may be responsible for constitutive or basal glucose uptake. Has a very broad substrate specificity; can transport a wide range of aldoses including b...
Gene Name
SLC2A1
Uniprot ID
P11166
Uniprot Name
Solute carrier family 2, facilitated glucose transporter member 1
Molecular Weight
54083.325 Da
References
  1. Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [PubMed:14642847]
  2. Vera JC, Rivas CI, Fischbarg J, Golde DW: Mammalian facilitative hexose transporters mediate the transport of dehydroascorbic acid. Nature. 1993 Jul 1;364(6432):79-82. [PubMed:8316303]
  3. Agus DB, Gambhir SS, Pardridge WM, Spielholz C, Baselga J, Vera JC, Golde DW: Vitamin C crosses the blood-brain barrier in the oxidized form through the glucose transporters. J Clin Invest. 1997 Dec 1;100(11):2842-8. [PubMed:9389750]

Drug created on February 15, 2013 17:15 / Updated on December 01, 2017 16:10