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Identification
NameDehydroascorbic Acid
Accession NumberDB08830
TypeSmall Molecule
GroupsExperimental
DescriptionDehydroascorbic 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
Dehydroascorbate
L-Dehydroascorbate
L-dehydroascorbic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIY2Z3ZTP9UM
CAS number490-83-5
WeightAverage: 174.1082
Monoisotopic: 174.016437924
Chemical FormulaC6H6O6
InChI KeyInChIKey=SBJKKFFYIZUCET-IDJHHGDLNA-N
InChI
InChI=1/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2?,5-/s2
IUPAC Name
(5R)-5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione
SMILES
[H]C([H])(O)C(O)[[email protected]]1OC(=O)C(=O)C1=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • 3-furanone
  • Oxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationThere is no approved indication for dehydroascorbic acid, but it has potential therapeutic use in patients with certain viruses and ischemic stroke.
PharmacodynamicsDehydroascorbic 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 actionEven 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting pointDecomposes 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
Polarizability14.12 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (46.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 both pentoses and hexoses.
Gene Name:
SLC2A1
Uniprot ID:
P11166
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 ]
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Drug created on February 15, 2013 17:15 / Updated on August 17, 2016 12:24