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 compounda phenol

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


Unification Links: PubChem:45479589

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 14.021197Inferred 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

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


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."

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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 19.5 on Sun Nov 29, 2015, BIOCYC14B.