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MetaCyc Compound: 6-hydroxy-2-(6-oxo-1-oxaspiro[2.5]octa-4,7-dien-2-yl)-1-benzofuran-3-one

Synonyms: phenoxy radical VII

Superclasses: an aromatic compound a phenol

Summary:
This study reports several phenoxy radicals as inetrmediate compounds in intermediate reaction steps|. This compound is referred to as phenoxy radical VII [Farag09]. Due to the vacuolar location the compound is protonated to pH 5 to 6 and represents a stable and neutral intermediate [Farag14]

Chemical Formula: C15H10O5

Molecular Weight: 270.24 Daltons

Monoisotopic Molecular Weight: 270.0528234315 Daltons

6-hydroxy-2-(6-oxo-1-oxaspiro[2.5]octa-4,7-dien-2-yl)-1-benzofuran-3-one compound structure

SMILES: C4(C=C3(C(=O)[CH](C2(OC1(C=CC(=O)C=C1)2))OC3=CC(O)=4))

InChI: InChI=1S/C15H10O5/c16-8-3-5-15(6-4-8)14(20-15)13-12(18)10-2-1-9(17)7-11(10)19-13/h1-7,13-14,17H

InChIKey: InChIKey=TYTGARXNZIJWFO-UHFFFAOYSA-N

Unification Links: PubChem:45479589

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 14.021197 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

hispidol and hispidol 4'-O-β-D-glucoside biosynthesis :
6-hydroxy-2-(6-oxo-1-oxaspiro[2.5]octa-4,7-dien-2-yl)-1-benzofuran-3-one → 6-hydroxy-2-(4-hydroxy-phenoxymethylene)-benzofuran-3-one

Reactions known to produce the compound:

hispidol and hispidol 4'-O-β-D-glucoside biosynthesis :
6-hydroxy-2-(6-oxo-1-oxaspiro[2.5]octa-4,7-dien-2-yl)-1-benzofuran-3-one + H2O ← 2-[hydroperoxy(4-hydroxyphenyl)methyl]-6-hydroxy-1-benzofuran-3-one

Not in pathways:
an aryl dialkyl phosphate + H2O → a dialkyl phosphate + a phenol
a phenyl acetate + H2O → a phenol + acetate + H+
a phenol sulfate + H2O → a phenol + sulfate + H+

In Reactions of unknown directionality:

Not in pathways:
a phenol + NADP+ = an aryl aldehyde + NADPH + H+
3'-phosphoadenylyl-sulfate + a phenol = adenosine 3',5'-bisphosphate + an aryl sulfate
a phenol + NAD+ = an aryl aldehyde + NADH + H+
UDP-α-D-glucose + a phenol = UDP + an aryl β-D-glucoside + H+
a phenol + an aryl sulfate = an aryl sulfate + a phenol

Credits:
Created 08-Dec-2009 by Pujar A , Boyce Thompson Institute


References

Farag09: Farag MA, Deavours BE, de Fatima A, Naoumkina M, Dixon RA, Sumner LW (2009). "Integrated metabolite and transcript profiling identify a biosynthetic mechanism for hispidol in Medicago truncatula cell cultures." Plant Physiol 151(3);1096-113. PMID: 19571306

Farag14: Farag, MA (2014). "personal communication 2014."

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 19.0 on Wed Apr 1, 2015, BIOCYC13A.