MetaCyc Compound: L-willardiine

Synonyms: 3-(uracil-1-yl)-L-alanine

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

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

L-willardiine compound structure

SMILES: C(C([N+])C(=O)[O-])N1(C=CC(=O)NC1=O)

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


Unification Links: ChEBI:57543 , KEGG:C03584 , KNApSAcK:C00001399 , PubChem:25200769

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 :
uracil + O-acetyl-L-serine → L-willardiine + 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-willardiine, sorted by the type of inhibition, are:

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


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."

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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
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