EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:3875 - coprine

ChEBI IDCHEBI:3875
ChEBI Namecoprine
Stars
DefinitionA non-proteinogenic L-α-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').
Last Modified8 January 2015
DownloadsMolfile
FormulaC8H14N2O4
Net Charge0
Average Mass202.210
Monoisotopic Mass202.09536
SMILESN[C@@H](CCC(=O)NC1(O)CC1)C(=O)O
InChIInChI=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
InChIKeyOEEZRBUCLFMTLD-YFKPBYRVSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor  An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of aldehyde dehydrogenase (NAD+), EC 1.2.1.3.
mycotoxin  Poisonous substance produced by fungi.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
coprine (CHEBI:3875) has role EC 1.2.1.3 [aldehyde dehydrogenase (NAD+)] inhibitor (CHEBI:35487)
coprine (CHEBI:3875) has role metabolite (CHEBI:25212)
coprine (CHEBI:3875) has role mycotoxin (CHEBI:25442)
coprine (CHEBI:3875) is a L-glutamine derivative (CHEBI:24317)
coprine (CHEBI:3875) is a cyclopropanes (CHEBI:51454)
coprine (CHEBI:3875) is a dicarboxylic acid monoamide (CHEBI:35735)
coprine (CHEBI:3875) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
IUPAC Name 
N-(1-hydroxycyclopropyl)-L-glutamine
Synonyms  Source
L-coprineHMDB
N5-(1-hydroxycyclopropyl)-L-glutamineChemIDplus
(2S)-2,5-diamino-5-oxopentanoic acidIUPAC
Manual XrefsDatabases
C08271KEGG COMPOUND
HMDB0034266HMDB
C00001349KNApSAcK
Registry NumbersSources
Reaxys:2053887Reaxys
CAS:58919-61-2KEGG COMPOUND
CAS:58919-61-2ChemIDplus
Citations