Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120270
Identification
Name: dehydroascorbate (bicyclic form)
Description:Ascorbate is oxidized in cells to dehydroascorbate via the monodehydroascorbate radical. Dehydroascorbate can be recycled back to ascorbate by the ascorbate glutathone cycle, or it can be further broken down in vivo by irreversible reactions. While the structure of dehydroascorbic acid found in most text books is that of L-dehydroascorbate, it appears that the actual structure in solution is that of a bicyclic monohydrate..
Structure
Thumb
Synonyms:
  • dehydroascorbate monohydrate
Chemical Formula: C6H8O7
Average Molecular Weight: 192.125
Monoisotopic Molecular Weight: 192.02701
InChI Key: QPPOKIPSRPKDEM-VPGXFDHMSA-N
InChI:InChI=1S/C6H8O7/c7-2-1-12-6(11)3(2)13-4(8)5(6,9)10/h2-3,7,9-11H,1H2/t2-,3+,6-/m0/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:C2(=O)(O[CH]1(C(O)(OCC(O)1)C(O)(O)2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Furofurans
Sub ClassIsosorbides
Direct Parent Isosorbides
Alternative Parents
Substituents
  • Isosorbide
  • Gamma butyrolactone
  • Monosaccharide
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl hydrate
  • Oxacycle
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular Framework Aliphatic heteropolycyclic compounds
External Descriptors
  • a small molecule (CPD-13907)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass192.1232ChemAxon
logP-3.3276ChemAxon
H-bond acceptors7ChemAxon
H-bond donors4ChemAxon
Rotatable bonds0ChemAxon
PSA116.4500ChemAxon
RO5 violations0ChemAxon
RO3 violations3ChemAxon
Refractivity33.8212ChemAxon
Atoms21ChemAxon
Rings2ChemAxon
Heavy atoms13ChemAxon
Hydrogen atoms8ChemAxon
Heteroatoms7ChemAxon
N/O atoms7ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers3ChemAxon
R/S chiral centers0ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers3ChemAxon
Stereo double bonds0ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds0ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References: Not Available
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    BioCycCPD-13907