Showing metabocard for Dehydroascorbic acid (BMDB0001264)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:17 UTC
Update Date2020-06-04 19:55:18 UTC
MCDB ID BMDB0001264
Secondary Accession Numbers
  • BMDB01264
Metabolite Identification
Common NameDehydroascorbic acid
DescriptionDehydroascorbic acid, also known as 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 is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydroascorbic acid exists in all living organisms, ranging from bacteria to humans. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In cattle, dehydroascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DehydroascorbateGenerator
1-DehydroascorbateHMDB
1-Dehydroascorbic acidHMDB
Dehydro-L-ascorbateHMDB
Dehydro-L-ascorbic acidHMDB
DHAAHMDB
L-DehydroascorbateHMDB
L-Dehydroascorbic acidHMDB
L-Threo-2,3-hexodiulosonic acid gamma-lactoneHMDB
L-Threo-hexo-2,3-diulosono-1,4-lactoneHMDB
Oxidized ascorbateHMDB
Oxidized ascorbic acidHMDB
Oxidized vitamin CHMDB
Dehydroerythorbic acidHMDB
Chemical FormulaC6H6O6
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
IUPAC Name(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional Name(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
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-/m1/s1
InChI KeySBJKKFFYIZUCET-DUZGATOHSA-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 DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9200000000-0a414c4d59046ece51c12017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fki-9831000000-c4b46024e1624e983ac32017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-4900000000-25a652482451303b3ca42012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-f1d23791c8a7b59576a32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2900000000-5ebc67e43b07167f34cb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-27ae8f5e1795d4f732a82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-0900000000-ee719ada45193fc650a02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0mbc-1900000000-d54b8e72e08e6ea1f7c02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9200000000-d07ff0053ddc28ce19152017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2.24 +/- 0.172 uM details
Detected and Quantified9 +/- 1.2 uM details
HMDB IDHMDB0001264
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021459
KNApSAcK IDNot Available
Chemspider ID182283
KEGG Compound IDC00425
BioCyc IDNot Available
BiGG ID34945
Wikipedia LinkDehydroascorbic acid
METLIN ID342
PubChem Compound210328
PDB IDNot Available
ChEBI ID17242
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. Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74. [PubMed:1880195 ]