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CHEBI:3875 - coprine

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
mycotoxin  Poisonous substance produced by fungi.
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.
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
(2S)-2,5-diamino-5-oxopentanoic acidIUPAC
N5-(1-hydroxycyclopropyl)-L-glutamineChemIDplus
L-coprineHMDB
Manual XrefsDatabases
C00001349KNApSAcK
C08271KEGG COMPOUND
HMDB0034266HMDB
Registry NumbersSources
Reaxys:2053887Reaxys
CAS:58919-61-2ChemIDplus
CAS:58919-61-2KEGG COMPOUND
Citations