Molecule ID: 108079

IUPAC Name: (2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid

Description: The molecule is a non-proteinogenic L-alpha-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Coprinus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect'). It has a role as an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor, a metabolite and a mycotoxin. It is a member of cyclopropanes, a dicarboxylic acid monoamide, a L-glutamine derivative and a non-proteinogenic L-alpha-amino acid.

SMILES: N[C@@H](CCC(O)=NC1(O)CC1)C(=O)O

SELFIES: [N][C@@H1][Branch1][S][C][C][C][Branch1][C][O][=N][C][Branch1][C][O][C][C][Ring1][Ring2][C][=Branch1][C][=O][O]

InChI: InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1

Molecular Properties:
- Polar Surface Area: 113.0 Ų
- LogP: -3.4