Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: monodehydroascorbate radical

Synonyms: monodehydroascorbic acid, semidehydroascorbic acid, semidehydroascorbate, ascorbyl radical

Superclasses: a radical

Summary:
L-ascorbate is oxidized in cells to dehydroascorbate via the radical monodehydroascorbate radical. Dehydroascorbate can be recycled back to ascorbate by the ascorbate glutathione cycle, or it can be further broken down in vivo by irreversible reactions.

Chemical Formula: C6H7O6

Molecular Weight: 175.12 Daltons

Monoisotopic Molecular Weight: 175.02426295729998 Daltons

SMILES: C(O)C(O)C1(C(O)=C(O)C(=O)O1)

InChI: InChI=1S/C6H7O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10H,1H2/t2-,5?/m0/s1

InChIKey: InChIKey=LHFJOBMTAJJOTB-SZSCBOSDSA-N

Unification Links: ChEBI:16504 , KEGG:C01041 , PubChem:54746216

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -155.11217 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

ascorbate glutathione cycle :
2 monodehydroascorbate radical → L-ascorbate + L-dehydro-ascorbate + H+
2 monodehydroascorbate radical + NADPH + H+ → 2 L-ascorbate + NADP+ + 2 H+

ascorbate recycling (cytosolic) :
2 monodehydroascorbate radical → L-ascorbate + L-dehydro-ascorbate + H+
2 monodehydroascorbate radical + NADPH + H+ → 2 L-ascorbate + NADP+ + 2 H+
2 monodehydroascorbate radical + NADH → 2 L-ascorbate + NAD+ + H+

Reactions known to produce the compound:

ascorbate glutathione cycle :
2 L-ascorbate + hydrogen peroxide + 2 H+ → 2 monodehydroascorbate radical + 2 H2O

ascorbate recycling (cytosolic) :
L-ascorbate + an oxidized electron acceptor + 2 H+monodehydroascorbate radical + a reduced electron acceptor

Not in pathways:
4 L-ascorbate + oxygen + 4 H+ → 4 monodehydroascorbate radical + 2 H2O
L-ascorbate[in] + Fe3+[out]monodehydroascorbate radical[in] + Fe2+[out]

In Reactions of unknown directionality:

Not in pathways:
a ferricytochrome b5 + L-ascorbate = a ferrocytochrome b5 + monodehydroascorbate radical

In Redox half-reactions:
monodehydroascorbate radical[in] + e- → L-ascorbate[in]

Credits:
Revised 19-Aug-2009 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, biocyc11.