Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: 8C-glucosyl-2-hydroxynaringenin

Superclasses: an aromatic compound an organic aromatic compound a phenylpropanoid a flavonoid a flavan a flavanone
an organic heterocyclic compound an organic heterobicyclic compound a benzopyran a 1-benzopyran a chromane a chromanone a flavanone
an organic heterocyclic compound an organic heterobicyclic compound a benzopyran a 1-benzopyran a chromane a flavan a flavanone
an organic heterocyclic compound an organic heterobicyclic compound a benzopyran a 1-benzopyran a chromene a flavonoid a flavan a flavanone

Citations: [BrazierHicks09]

Chemical Formula: C21H21O11

Molecular Weight: 449.39 Daltons

Monoisotopic Molecular Weight: 450.11621154930003 Daltons

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

InChI: InChI=1S/C21H22O11/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/h1-4,6,14,17,19-23,26-31H,5,7H2/p-1/t14-,17-,19+,20-,21+/m1/s1

InChIKey: InChIKey=GCEHZSFCBPUADZ-VJXVFPJBSA-M

Unification Links: PubChem:49859582

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -103.67852 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

C-glycosylflavone biosynthesis I :
8C-glucosyl-2-hydroxynaringenin + H+ → 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 + 2 NADPH + 2 oxygen + 2 H+ → a 3',5'-dihydroxy isoflavanone + 2 NADP+ + 2 H2O


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 + 2 H+

In Reactions of unknown directionality:

Not in pathways:
a flavanone + NADPH + oxygen + H+ = a 3' hydroxy flavanone + NADP+ + H2O
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 SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc14.