Skip to content
L-agaritine

Structure via PubChem · Public domain (PubChem)

EntityQ2315302· pop 10· linked from 54 articles

L-agaritine

Sign in to save

Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus. It is an α-aminoacid and a derivative of phenylhydrazine.

Chemical data

Formula
C12H17N3O4
Molecular weight
267.28 g/mol
IUPAC name
(2S)-2-amino-5-[2-[4-(hydroxymethyl)phenyl]hydrazinyl]-5-oxopentanoic acid
SMILES
C1=CC(=CC=C1CO)NNC(=O)CC[C@@H](C(=O)O)N
InChIKey
SRSPQXBFDCGXIZ-JTQLQIEISA-N
XLogP
-2.8
Polar surface area
125 Ų
H-bond donors
5
H-bond acceptors
6
Formal charge
0

via PubChem

Wikidata facts

Has part
hydrogen
Mass
267.121906024
Show 4 more facts
canonical SMILES
C1=CC(=CC=C1CO)NNC(=O)CCC(C(=O)O)N
chemical formula
C₁₂H₁₇N₃O₄
isomeric SMILES
C1=CC(=CC=C1CO)NNC(=O)CC[C@@H](C(=O)O)N
found in taxon
Agaricus bisporus
Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections
Contents
  • Occurrence
  • Production
  • Potential for toxicity
  • See also
  • References

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477243563 | ImageFile = Agaritine.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Stereo structural formula of agaritine ((2S)-2-amino) | ImageFile1 = Agaritine_3d_structure.png | ImageFile1_Ref = | ImageSize1 = 244 | ImageName1 = Ball and stick model of agaritine ((2S)-2-amino) | IUPACName = 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide | SystematicName = 2-Amino-4-{N'-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid | OtherNames = β-N-[γ-glutamyl]-4-hydroxymethylphenylhydrazine N2-(γ-glutamyl)-4-hydroxymethylphenylhydrazine |Section1= |Section2= |Section7= }} Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus. It is an α-aminoacid and a derivative of phenylhydrazine.

==Occurrence== Agaritine is present as a natural mycotoxin in fresh samples of at least 24 species of the genera Agaricus, Leucoagaricus, and Macrolepiota. Mushrooms of these species are found around the world. These mushrooms grow in a wide range of habitats. Agaricus bisporus is cultivated in over 70 countries and on every continent except Antarctica. A. bisporus, also known as the portobello or common button mushroom, is of particular socio-economic importance in developed countries.

Excerpted from Wikipedia’s “L-agaritine” article, available under the CC BY-SA 4.0 licence.

Gallery (2)