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MetaCyc Compound: 8C-glucosyl-2-hydroxynaringenin

Superclasses: an aromatic compoundan organic aromatic compounda phenylpropanoida flavonoida flavana flavanone
an organic heterocyclic compoundan organic heterobicyclic compounda benzopyrana 1-benzopyrana chromanea chromanonea flavanone
an organic heterocyclic compoundan organic heterobicyclic compounda benzopyrana 1-benzopyrana chromanea flavana flavanone
an organic heterocyclic compoundan organic heterobicyclic compounda benzopyrana 1-benzopyrana chromenea flavonoida flavana flavanone

Citations: [BrazierHicks09]

Chemical Formula: C21H21O11

Molecular Weight: 449.39 Daltons

Monoisotopic Molecular Weight: 450.11621154930003 Daltons

8C-glucosyl-2-hydroxynaringenin compound structure

SMILES: C1(C=C(O)C=CC=1C(=O)[C-]C(=O)C3(C(O)=C(C2(C(C(C(O)C(O2)CO)O)O))C(O)=CC(O)=3))

InChI: InChI=1S/C21H21O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)11(25)5-10(24)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,26-31H,7H2/q-1/t14-,17-,19+,20-,21+/m1/s1

InChIKey: InChIKey=FGASONPHQXGZIK-VJXVFPJBSA-N

Unification Links: PubChem:90657395

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -101.19852Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

C-glycosylflavone biosynthesis I :
8C-glucosyl-2-hydroxynaringenin → vitexin + H2O

Not in pathways:
a flavanone + 2-oxoglutarate + oxygen → a flavone + succinate + CO2 + H2O
a flavanone + 2-oxoglutarate + oxygen → a dihydroflavonol + succinate + CO2
a flavanone + NADPH + oxygen + H+ → a 3' hydroxy flavanone + NADP+ + H2O
a flavanone + 2 NADPH + 2 oxygen + 2 H+ → a 3',5'-dihydroxy isoflavanone + 2 NADP+ + 2 H2O

Not in pathways:
a flavonoid + NADPH + oxygen + H+ → a 3'-hydroxy-flavonoid + NADP+ + H2O

Reactions known to produce the compound:

C-glycosylflavone biosynthesis I :
naringenin dibenzoylmethane tautomer + UDP-α-D-glucose → 8C-glucosyl-2-hydroxynaringenin + UDP + H+

In Reactions of unknown directionality:

Not in pathways:
UDP-α-D-glucose + a flavanone = a flavanone-7-O-β-D-glucoside + UDP
a chalcone = a flavanone

Credits:
Created 20-Sep-2010 by Pujar A, Boyce Thompson Institute


References

BrazierHicks09: Brazier-Hicks M, Evans KM, Gershater MC, Puschmann H, Steel PG, Edwards R (2009). "The C-glycosylation of flavonoids in cereals." J Biol Chem 284(27);17926-34. PMID: 19411659

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 Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc11.