MiMeDB: Showing metabocard for L-dehydroascorbate (MMDBc0054537)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:16:59 UTC

Update Date

2024-10-13 08:38:16 UTC

Metabolite ID

MMDBc0054537

Metabolite Identification

Common Name

L-dehydroascorbate

Description

Dehydroascorbic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Synonyms

Value	Source
Dehydro-L-ascorbic acid	ChEBI
Dehydroascorbic acid	ChEBI
DHAA	ChEBI
L-Dehydroascorbate	ChEBI
L-threo-2,3-Hexodiulosonic acid, gamma-lactone	ChEBI
L-threo-hexo-2,3-diulosono-1,4-Lactone	ChEBI
Oxidized ascorbic acid	ChEBI
Oxidized vitamin C	ChEBI
Dehydro-L-ascorbate	Generator
Dehydroascorbate	Generator
L-threo-2,3-Hexodiulosonate, g-lactone	Generator
L-threo-2,3-Hexodiulosonate, gamma-lactone	Generator
L-threo-2,3-Hexodiulosonate, γ-lactone	Generator
L-threo-2,3-Hexodiulosonic acid, g-lactone	Generator
L-threo-2,3-Hexodiulosonic acid, γ-lactone	Generator
Oxidized ascorbate	Generator
Acid, dehydroascorbic	MeSH
L-Dehydro-ascorbate	HMDB
L-Dehydroascorbic acid	HMDB
L-threo-Dehydroascorbic acid	HMDB

Molecular Formula

C₆H₆O₆

Average Mass

174.1082

Monoisotopic Mass

174.016437924

IUPAC Name

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

Traditional Name

DHAA

CAS Registry Number

Not Available

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

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

dehydroascorbic acid (CHEBI:27956 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	190 g/L	ALOGPS
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	14.02 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-05fr-1910000000-637a588dd38c4cc58ae5	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fs-1910000000-194039de8a412e640d7f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fs-1900000000-af0738c9bda7200b8742	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08iu-9200000000-bbb79c0fcf383789f477	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-4900000000-25a652482451303b3ca4	2020-06-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-c9ba5aa4017d618b9908	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-52e4a1b574cf41140928	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-e89ff5aa246bed40fed2	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-1900000000-c546ba0f061c1d25a934	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mbc-2900000000-254c596333e32143329f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fr-9700000000-a77d2c857a58b59513cc	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-649b7b705ac3b8d2acd6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08mi-9700000000-aede5d559ec646353d18	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-e10d14ae5b3c3444469c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05r9-1900000000-9797d9ac8e5d4a8c4536	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9500000000-0064fc20716aed5e9721	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9100000000-2305f252ccf8065c346d	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2020-06-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2020-06-23	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Brain
Erythrocyte
Intestine
Placenta
Platelet
Urine

Tissue Locations

Blood
Brain
Erythrocyte
Intestine
Placenta
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191922	Peptidyl-glycine alpha-amidating monooxygenase	Unknown	P19021	Homo sapiens
MMDBp0191923	Dopamine beta-hydroxylase	Unknown	P09172	Homo sapiens
MMDBp0192442	Glutathione S-transferase omega-1	Enzyme	P78417	Homo sapiens
MMDBp0192451	Glutathione S-transferase omega-2	Enzyme	Q9H4Y5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	12.636	5.744			uM	Adult (>18 years old)	Both	Normal	HMDB	16755268
Human Blood	Detected and Quantified	2.32	0.78			uM	Adult (>18 years old)	Both	Normal	HMDB	9094879
Human Blood	Detected and Quantified	2.36	0.11			uM	Adult (>18 years old)	Both	Normal	HMDB	9094879
Human Urine	Detected and Quantified	9.1		5.8	7.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			1.72	7.47	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Blood	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001264

DrugBank ID

DB08830

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Dehydroascorbic acid

METLIN ID

342

PubChem Compound

440667

PDB ID

Not Available

ChEBI ID

27956

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1093/ajcn/54.4.712. [PubMed:1897478 ]
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. doi: 10.1093/ajcn/54.6.1315s. [PubMed:1962589 ]
Toivola DM, Isomaa B: Effects of dehydroabietic acid on the erythrocyte membrane. Chem Biol Interact. 1991;79(1):65-78. doi: 10.1016/0009-2797(91)90053-a. [PubMed:2060038 ]
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 ]
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 ]
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 ]
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. doi: 10.1016/0014-5793(95)01413-6. [PubMed:8549805 ]
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. doi: 10.1016/0891-5849(95)02130-2. [PubMed:8904295 ]
Mendiratta S, Qu ZC, May JM: Erythrocyte ascorbate recycling: antioxidant effects in blood. Free Radic Biol Med. 1998 Mar 15;24(5):789-97. doi: 10.1016/s0891-5849(97)00351-1. [PubMed:9586809 ]
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. doi: 10.1016/s0006-2952(97)00637-0. [PubMed:9719486 ]
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. doi: 10.1093/ndt/14.6.1472. [PubMed:10383010 ]
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. doi: 10.1016/s0049-3848(03)00312-8. [PubMed:12893026 ]
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 ]
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. doi: 10.1097/00126334-200408150-00007. [PubMed:15247557 ]
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. doi: 10.1385/BTER:100:2:125. [PubMed:15326362 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for L-dehydroascorbate (MMDBc0054537)

MOL for #<Metabolite:0x00007fdb50e8a778>

3D MOL for #<Metabolite:0x00007fdb50e8a778>

3D SDF for #<Metabolite:0x00007fdb50e8a778>

3D-SDF for #<Metabolite:0x00007fdb50e8a778>

PDB for #<Metabolite:0x00007fdb50e8a778>

3D PDB for #<Metabolite:0x00007fdb50e8a778>

SMILES for #<Metabolite:0x00007fdb50e8a778>

INCHI for #<Metabolite:0x00007fdb50e8a778>

Structure for #<Metabolite:0x00007fdb50e8a778>

3D Structure for #<Metabolite:0x00007fdb50e8a778>