L-dehydroascorbic acid (CHEBI:27956)

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ChEBI Name	L-dehydroascorbic acid

ChEBI ID	CHEBI:27956

ChEBI ASCII Name	L-dehydroascorbic acid

Definition	Dehydroascorbic acid having the L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:21280, CHEBI:21279, CHEBI:6210

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Formula

C6H6O6

Net Charge

Average Mass

174.10824

Monoisotopic Mass

174.01644

InChI

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

InChIKey

SBJKKFFYIZUCET-JLAZNSOCSA-N

SMILES

[H][C@@]1(OC(=O)C(=O)C1=O)[C@@H](O)CO

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Biological Role(s):	coenzyme A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). (via dehydroascorbic acid ) water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via vitamin C )

ChEBI Ontology
Outgoing	L-dehydroascorbic acid (CHEBI:27956) has functional parent L-ascorbic acid (CHEBI:29073) L-dehydroascorbic acid (CHEBI:27956) has role coenzyme (CHEBI:23354) L-dehydroascorbic acid (CHEBI:27956) has role mouse metabolite (CHEBI:75771) L-dehydroascorbic acid (CHEBI:27956) is a dehydroascorbic acid (CHEBI:17242) L-dehydroascorbic acid (CHEBI:27956) is a vitamin C (CHEBI:176783) L-dehydroascorbic acid (CHEBI:27956) is conjugate acid of L-dehydroascorbate (CHEBI:58539)

Incoming	L-dehydroascorbic acid hydrate (CHEBI:178008) has part L-dehydroascorbic acid (CHEBI:27956) L-dehydroascorbate (CHEBI:58539) is conjugate base of L-dehydroascorbic acid (CHEBI:27956)

IUPAC Name

(5R)-5-[(1S)-1,2-dihydroxyethyl]furan-2,3,4(5H)-trione

Synonyms	Sources
dehydro-L-ascorbic acid	ChemIDplus
dehydroascorbic acid	ChemIDplus
Dehydroascorbic acid	KEGG COMPOUND
DHAA	ChemIDplus
L-Dehydroascorbate	KEGG COMPOUND
L-Dehydroascorbate	KEGG COMPOUND
L-Dehydroascorbic acid	KEGG COMPOUND
L-threo-2,3-hexodiulosonic acid, γ-lactone	ChemIDplus
L-threo-hexo-2,3-diulosono-1,4-lactone	ChemIDplus
oxidized ascorbic acid	ChemIDplus
oxidized vitamin C	ChemIDplus

Last Modified

14 May 2024

General Comment
2010-12-14	An oxidation product of L-ascorbic acid (vitamin C) and an intermediate in its degradation. A potent glycation agent, it may also have stronger antiviral effects than vitamin C.