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Showing NP-Card for Dehydroascorbic acid (NP0000375)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:03 UTC
NP-MRD IDNP0000375
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydroascorbic acid
DescriptionDehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. Dehydroascorbic 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 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000375 (Dehydroascorbic acid)


  Mrv1652306232017422D          

 13 13  0  0  1  0            999 V2000
    0.0862    0.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1787   -0.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850    0.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084   -0.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563    0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006   -1.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    0.5162    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5147    0.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2443    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -0.4267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412    0.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  5  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  2  0  0  0  0
  7 10  1  1  0  0  0
  8 11  1  0  0  0  0
  1 12  1  1  0  0  0
  5 13  2  0  0  0  0
M  END
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3D MOL for NP0000375 (Dehydroascorbic acid)

HMDB0001264
     RDKit          3D
Dehydroascorbic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.6303   -1.3453   -1.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014   -0.7630   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -1.2767   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -0.1958   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8997   -0.4868    0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4700   -1.6104   -0.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.6951   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    0.4668    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.8504    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850    1.6992    1.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    0.6457   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4672    1.5178   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087    0.0686   -1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639   -0.5863    1.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -2.4451    0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    0.8016   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3584    1.5982    0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108    0.3659   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11  2  1  0
  4 13  1  6
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
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3D SDF for NP0000375 (Dehydroascorbic acid)


  Mrv1652306232017422D          

 13 13  0  0  1  0            999 V2000
    0.0862    0.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1787   -0.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850    0.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084   -0.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563    0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006   -1.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    0.5162    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5147    0.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2443    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -0.4267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412    0.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  5  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  2  0  0  0  0
  7 10  1  1  0  0  0
  8 11  1  0  0  0  0
  1 12  1  1  0  0  0
  5 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000375

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
SBJKKFFYIZUCET-JLAZNSOCSA-N

> <FORMULA>
C6H6O6

> <MOLECULAR_WEIGHT>
174.1082

> <EXACT_MASS>
174.016437924

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.017537359104114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-0.6728306333333334

> <ALOGPS_LOGS>
0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.947507235055642

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5571896779025947

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980802852202162

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
33.5458

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DHAA

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000375 (Dehydroascorbic acid)

HMDB0001264
     RDKit          3D
Dehydroascorbic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.6303   -1.3453   -1.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014   -0.7630   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -1.2767   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -0.1958   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8997   -0.4868    0.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4700   -1.6104   -0.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189    0.6951   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    0.4668    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.8504    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850    1.6992    1.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    0.6457   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4672    1.5178   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087    0.0686   -1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639   -0.5863    1.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -2.4451    0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    0.8016   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3584    1.5982    0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108    0.3659   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11  2  1  0
  4 13  1  6
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
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PDB for NP0000375 (Dehydroascorbic acid)

HEADER    PROTEIN                                 23-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-20         0                                  
HETATM    1  C   UNK     0       0.161   0.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.334  -1.265   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.092   1.094   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.882  -1.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.345   0.175   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.801  -2.511   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.494   0.964   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.827   0.194   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.567  -2.521   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.494   2.521   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.189   0.980   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       1.367  -0.796   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      -3.810   0.649   0.000  0.00  0.00           O+0
CONECT    1    2    3    7   12                                             
CONECT    2    1    4    9                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    5                                                  
CONECT    5    3    4   13                                                  
CONECT    6    4                                                            
CONECT    7    1    8   10                                                  
CONECT    8    7   11                                                       
CONECT    9    2                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    1                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000375 (Dehydroascorbic acid)

COMPND    HMDB0001264
HETATM    1  O1  UNL     1      -3.630  -1.345  -1.042  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.601  -0.763  -0.577  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.334  -1.277  -0.359  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.427  -0.196  -0.474  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.900  -0.487   0.159  1.00  0.00           C  
HETATM    6  O3  UNL     1       1.470  -1.610  -0.443  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.819   0.695  -0.175  1.00  0.00           C  
HETATM    8  O4  UNL     1       3.099   0.467   0.322  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.184   0.850   0.294  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.785   1.699   1.121  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.568   0.646  -0.163  1.00  0.00           C  
HETATM   12  O6  UNL     1      -3.467   1.518  -0.172  1.00  0.00           O  
HETATM   13  H1  UNL     1      -0.309   0.069  -1.524  1.00  0.00           H  
HETATM   14  H2  UNL     1       0.864  -0.586   1.245  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.282  -2.445   0.039  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.802   0.802  -1.268  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.358   1.598   0.262  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.711   0.366  -0.457  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5    9   13
CONECT    5    6    7   14
CONECT    6   15
CONECT    7    8   16   17
CONECT    8   18
CONECT    9   10   10   11
CONECT   11   12   12
END
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SMILES for NP0000375 (Dehydroascorbic acid)

[H][C@@]1(OC(=O)C(=O)C1=O)[C@@H](O)CO
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INCHI for NP0000375 (Dehydroascorbic acid)

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
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View in JSmol
Synonyms
ValueSource
Dehydro-L-ascorbic 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
L-Dehydroascorbic acidKegg
Dehydro-L-ascorbateGenerator
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
DehydroascorbateGenerator
Acid, dehydroascorbicHMDB
L-Dehydro-ascorbateHMDB
L-Threo-dehydroascorbic acidHMDB
Dehydroascorbic acidChEBI
Chemical FormulaC6H6O6
Average Mass174.1082 Da
Monoisotopic Mass174.01644 Da
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional NameDHAA
CAS Registry Number490-83-5
SMILES
[H][C@@](O)(CO)[C@@]1([H])OC(=O)C(=O)C1=O
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaLOTUS Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lotus corniculatusLOTUS Database
Lotus glaberLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rosa caninaLOTUS Database
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point389.25 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.702 (est)The Good Scents Company Information System
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
HMDB IDHMDB0001264
DrugBank IDDB08830
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011907
KNApSAcK IDC00053096
Chemspider ID389547
KEGG Compound IDC05422
BioCyc IDL-DEHYDRO-ASCORBATE
BiGG IDNot Available
Wikipedia LinkDehydroascorbic acid
METLIN ID342
PubChem Compound440667
PDB IDNot Available
ChEBI ID27956
Good Scents IDrw1234571
References
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 ]