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Showing metabocard for Dehydroascorbic acid (HMDB0001264)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:34 UTC
HMDB IDHMDB0001264
Secondary Accession Numbers
  • HMDB01264
Metabolite Identification
Common NameDehydroascorbic acid
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001264 (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 HMDB0001264 (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 HMDB0001264 (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>
HMDB0001264

> <DATABASE_NAME>
hmdb

> <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

$$$$
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3D-SDF for HMDB0001264 (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 HMDB0001264 (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 HMDB0001264 (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 HMDB0001264 (Dehydroascorbic acid)

[H][C@@]1(OC(=O)C(=O)C1=O)[C@@H](O)CO
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INCHI for HMDB0001264 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H6O6
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional NameDHAA
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+/m0/s1
InChI KeySBJKKFFYIZUCET-JLAZNSOCSA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Blood
  • Brain
  • Erythrocyte
  • Intestine
  • Placenta
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08830
Phenol Explorer Compound IDNot Available
FooDB IDFDB011907
KNApSAcK IDC00007380
Chemspider ID389547
KEGG Compound IDC05422
BioCyc IDL-DEHYDRO-ASCORBATE
BiGG IDNot Available
Wikipedia LinkDehydroascorbic acid
METLIN ID342
PubChem Compound440667
PDB IDNot Available
ChEBI ID27956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceUtsumi, Isamu; Harada, Kiyoshi; Miura, Hiroshi. Dehydroascorbic acid. Jpn. Tokkyo Koho (1972), 2 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Peptidyl-glycine alpha-amidating monooxygenase
General function:
Involved in monooxygenase activity
Specific function:
Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:
PAM
Uniprot ID:
P19021
Molecular weight:
108402.425
Reactions
Peptidylglycine + Ascorbic acid + Oxygen → peptidyl(2-hydroxyglycine) + Dehydroascorbic acid + Waterdetails
Enzyme Details
2. Dopamine beta-hydroxylase
General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
Reactions
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails
Enzyme Details
3. Glutathione S-transferase omega-1
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
Glutathione + Dehydroascorbic acid → Oxidized glutathione + Ascorbic aciddetails
Enzyme Details
4. Glutathione S-transferase omega-2
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase activity. Has high dehydroascorbate reductase activity and may contribute to the recycling of ascorbic acid. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA).
Gene Name:
GSTO2
Uniprot ID:
Q9H4Y5
Molecular weight:
24399.09
Reactions
Glutathione + Dehydroascorbic acid → Oxidized glutathione + Ascorbic aciddetails