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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
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MetaCyc Compound: L-isowillardiine

Synonyms: 3-(uracil-3-yl)-L-alanine, β-uracil-3-ylalanine

Superclasses: an amino acid or its derivative an amino acid a modified amino acid

Summary:
Willardiine is a non-protein amino acid naturally found in Acacia willardiana, Mimosa asperata, and pea (Pisum sativum). It exists as either a free amino acid, a γ-glutamylpeptide or a tripeptide. Isowillardiine, a willardiine isoform, is only detectable from the genus Pisum.

Chemical Formula: C7H9N3O4

Molecular Weight: 199.17 Daltons

Monoisotopic Molecular Weight: 199.05930579289998 Daltons

SMILES: C1(=CC(N(C(N1)=O)CC(C(=O)[O-])[N+])=O)

InChI: InChI=1S/C7H9N3O4/c8-4(6(12)13)3-10-5(11)1-2-9-7(10)14/h1-2,4H,3,8H2,(H,9,14)(H,12,13)/t4-/m0/s1

InChIKey: InChIKey=AZSWUZQIIMMKOZ-BYPYZUCNSA-N

Unification Links: ChemSpider:146944 , HMDB:HMDB30376 , KEGG:C08289 , PubChem:167983

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -44.369904 Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

willardiine and isowillardiine biosynthesis :
O-acetyl-L-serine + uracil → L-isowillardiine + acetate + H+

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Enzymes inhibited by L-isowillardiine, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: willardiine synthase [Ahmmad84] , isowillardiine synthase [Ahmmad84]


References

Ahmmad84: Ahmmad, Mohammad A.S., Maskall, C. Sidney, Brown, Eric G. (1984). "Partial purification and properties of willardiine and isowillardiine synthase activity from Pisum sativum." Phytochemistry, 1984, 23(2):265-270.

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 Wed Nov 26, 2014, biocyc13.