NP-MRD: Showing NP-Card for acid, dehydroascorbic (NP0152832)

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Record Information

Version

2.0

Created at

2022-09-02 09:23:24 UTC

Updated at

2022-09-02 09:23:24 UTC

NP-MRD ID

NP0152832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acid, dehydroascorbic

Description

Dehydroascorbic acid, also known as dehydroascorbate, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through the action of the enzyme dopamine beta-hydroxylase. Ascorbic acid protects the mitochondrial genome and membrane. In humans, dehydroascorbic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, Dehydroascorbic acid is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (c. Annuum) and in a lower concentration in green bell peppers, cassava, and orange bell peppers. Dehydroascorbic acid has also been detected, but not quantified in, several different foods, such as carrots, broccoli, wild leeks, cabbages, and spinachs. This could make dehydroascorbic acid a potential biomarker for the consumption of these foods. As a pharmaceutical agent, some research has suggested that administration of dehydroascorbic acid may confer protection from neuronal injury following an ischemic stroke. It may be used in a process for permanent waving of hair and in a process for sunless tanning of skin. Recycling of ascorbate via active transport of DHA into cells, followed by reduction and reuse, mitigates the inability of humans to synthesize it from glucose. acid, dehydroascorbic is found in Arabidopsis thaliana, Hyacinthoides non-scripta and Populus tremula. The actual structure shown by spectroscopic studies is the result of rapid hemiacetal formation between the 6-OH and the 3-carbonyl groups.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    5    8                                                  
CONECT    3    4    5    9                                                  
CONECT    4    3    6   10                                                  
CONECT    5    2    3   12                                                  
CONECT    6    4   11   12                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
Dehydroascorbate	ChEBI
Dehydroascorbates	ChEBI

Chemical Formula

C₆H₆O₆

Average Mass

174.1082 Da

Monoisotopic Mass

174.01644 Da

IUPAC Name

5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione

Traditional Name

dehydroascorbic acid

CAS Registry Number

Not Available

SMILES

OCC(O)C1OC(=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

InChI Key

SBJKKFFYIZUCET-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633
Hyacinthoides non-scripta	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tetrahydrofuranone (CHEBI:17242 )
a small molecule (L-DEHYDRO-ASCORBATE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-0.67	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.55 m³·mol⁻¹	ChemAxon
Polarizability	14.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011907

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dehydroascorbic acid

METLIN ID

Not Available

PubChem Compound

835

PDB ID

Not Available

ChEBI ID

17242

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for acid, dehydroascorbic (NP0152832)

MOL for NP0152832 (acid, dehydroascorbic)

3D MOL for NP0152832 (acid, dehydroascorbic)

3D SDF for NP0152832 (acid, dehydroascorbic)

3D-SDF for NP0152832 (acid, dehydroascorbic)

PDB for NP0152832 (acid, dehydroascorbic)

3D PDB for NP0152832 (acid, dehydroascorbic)

SMILES for NP0152832 (acid, dehydroascorbic)

INCHI for NP0152832 (acid, dehydroascorbic)

Structure for NP0152832 (acid, dehydroascorbic)

3D Structure for NP0152832 (acid, dehydroascorbic)