L-Dehydroascorbic acid (Compound)

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ID	590
Name	L-Dehydroascorbic acid
Synonyms	Ascorbic acid, oxidized; DHAA; Dehydroascorbic acid
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000590 (L-Dehydroascorbic acid) 3D Structure for EE000590 (L-Dehydroascorbic acid) 440667 -OEChem-10191917433D 18 18 0 1 0 0 0 0 0999 V2000 0.1500 -1.0901 0.6019 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3618 0.1778 -1.3676 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8906 -0.2865 -0.3236 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8243 2.3470 0.2264 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9139 0.5794 -0.5451 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0678 -2.1593 -0.1743 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3545 0.2687 0.8074 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6264 0.4553 0.0095 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7558 1.1422 0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7310 -0.4886 0.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8451 0.2344 -0.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4074 -1.1804 0.0870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4947 0.4177 1.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9674 1.4956 0.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4416 -1.5365 0.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9924 -0.3177 1.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1950 0.2984 -1.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1709 0.6369 -0.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 12 1 0 0 0 0 2 8 1 0 0 0 0 2 17 1 0 0 0 0 3 10 1 0 0 0 0 3 18 1 0 0 0 0 4 9 2 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 440667 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 3 2 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 14 1 -0.43 10 0.28 11 0.57 12 0.72 17 0.4 18 0.4 2 -0.68 3 -0.68 4 -0.57 5 -0.57 6 -0.57 7 0.34 8 0.28 9 0.51 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 2.4 > <PUBCHEM_PHARMACOPHORE_FEATURES> 9 1 11 anion 1 2 acceptor 1 2 donor 1 3 acceptor 1 3 donor 1 4 acceptor 1 5 acceptor 1 6 acceptor 5 1 7 9 11 12 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 12 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 2 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 2 > <PUBCHEM_CONFORMER_ID> 0006B95B00000001 > <PUBCHEM_MMFF94_ENERGY> 22.7558 > <PUBCHEM_FEATURE_SELFOVERLAP> 45.686 > <PUBCHEM_SHAPE_FINGERPRINT> 11031198 65 18334867146385986973 12423570 1 10703089781968676096 12897270 3 18335421309126457833 16945 1 18339648931108442385 20201158 50 18334579052996736859 20645477 70 18410569553510664535 23235685 24 18336825402533853136 23552423 10 18118129073720003970 2748010 2 18266737982940323156 29004967 10 18411418392970337928 5084963 1 17530678839988239121 528886 8 18340485668163198072 > <PUBCHEM_SHAPE_MULTIPOLES> 211.74 4.25 1.7 0.85 3.16 0.08 0.11 -0.83 0.7 -1.26 -0.11 0.22 0.03 0.06 > <PUBCHEM_SHAPE_SELFOVERLAP> 437.883 > <PUBCHEM_SHAPE_VOLUME> 119.8 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Oxidized form of ascorbic acid.
Classification	Compounds > Chemical entities > Organic compounds > Organoheterocyclic compounds > Lactones > Gamma butyrolactones
CAS number	490-83-5
PubChem ID	440667
ChEBI ID	27956
FooDB ID	FDB021459
HMDB ID	HMDB0001264

Chemical data

MolDBi data

IUPAC Name	(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional IUPAC Name	DHAA
Formula	C6H6O6
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
InChI Key	SBJKKFFYIZUCET-JLAZNSOCSA-N
Molecular weight	174.1082
Exact mass	174.016437924
SMILES	[H][C@](O)(CO)[C@@]1([H])OC(=O)C(=O)C1=O

ClassyFire 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	Furanones Tetrahydrofurans Secondary alcohols Cyclic ketones Carboxylic acid esters 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives

Publications with L-Dehydroascorbic acid

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of L-Dehydroascorbic acid in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of L-Dehydroascorbic acid with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of L-Dehydroascorbic acid with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of L-Dehydroascorbic acid exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of L-Dehydroascorbic acid exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication