CHEBI:3875 - coprine

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ChEBI Name coprine
ChEBI ID CHEBI:3875
Definition A 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').
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C8H14N2O4
Net Charge 0
Average Mass 202.20780
Monoisotopic Mass 202.095
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
InChIKey OEEZRBUCLFMTLD-YFKPBYRVSA-N
SMILES N[C@@H](CCC(=O)NC1(O)CC1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(2S)-2,5-diamino-5-oxopentanoic acid IUPAC
L-coprine HMDB
N5-(1-hydroxycyclopropyl)-L-glutamine ChemIDplus
Manual Xrefs Databases
C00001349 KNApSAcK
C08271 KEGG COMPOUND
HMDB0034266 HMDB
View more database links
Registry Numbers Types Sources
2053887 Reaxys Registry Number Reaxys
58919-61-2 CAS Registry Number KEGG COMPOUND
58919-61-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1241098 PubMed citation Europe PMC
1553385 PubMed citation Europe PMC
2474765 PubMed citation Europe PMC
350009 PubMed citation Europe PMC
473235 PubMed citation Europe PMC
558210 PubMed citation Europe PMC
577107 PubMed citation Europe PMC
7097272 PubMed citation Europe PMC
7159468 PubMed citation Europe PMC
Last Modified
08 January 2015