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

2022-08-27 01:44:36 UTC

MiMeDB 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 SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

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

Proteins

#<MetaboliteProteinLink:0x000055b76e202080>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

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

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

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

External Links

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:0x000055b76e072350>

3D MOL for #<Metabolite:0x000055b76e072350>

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3D Structure for #<Metabolite:0x000055b76e072350>