CHEBI:34727 - domoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name domoic acid
ChEBI ID CHEBI:34727
Definition An L-proline derivative produced by the diatomic algal genus of Pseudo-nitzschia and other related species that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is an analogue of kainic acid and is the neurotoxin associated with amnesic shellfish poisoning (ASP).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C15H21NO6
Net Charge 0
Average Mass 311.33030
Monoisotopic Mass 311.137
InChI InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1
InChIKey VZFRNCSOCOPNDB-AOKDLOFSSA-N
SMILES C[C@H](\C=C\C=C(\C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O)C(O)=O
Metabolite of Species Details
Pseudo-nitzschia (NCBI:41953) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): neurotoxin
A poison that interferes with the functions of the nervous system.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
hapten
Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
Application(s): neuromuscular agent
A drug used for its actions on skeletal muscle.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing domoic acid (CHEBI:34727) has role hapten (CHEBI:59174)
domoic acid (CHEBI:34727) has role marine metabolite (CHEBI:76507)
domoic acid (CHEBI:34727) has role neuromuscular agent (CHEBI:51372)
domoic acid (CHEBI:34727) has role neurotoxin (CHEBI:50910)
domoic acid (CHEBI:34727) is a L-proline derivative (CHEBI:84186)
domoic acid (CHEBI:34727) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
domoic acid (CHEBI:34727) is a pyrrolidinecarboxylic acid (CHEBI:46767)
domoic acid (CHEBI:34727) is a tricarboxylic acid (CHEBI:27093)
IUPAC Name
(3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline
Synonym Source
L-domoic acid ChemIDplus
Database Links Databases
C13732 KEGG COMPOUND
Domoic_acid Wikipedia
DOQ PDBeChem
HMDB0033939 HMDB
View more database links
Registry Numbers Types Sources
14277-97-5 CAS Registry Number KEGG COMPOUND
14277-97-5 CAS Registry Number ChemIDplus
5126272 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10223629 PubMed citation Europe PMC
18728725 PubMed citation Europe PMC
20120452 PubMed citation Europe PMC
22406515 PubMed citation Europe PMC
24511141 PubMed citation Europe PMC
24564603 PubMed citation Europe PMC
24638960 PubMed citation Europe PMC
24663110 PubMed citation Europe PMC
28817087 PubMed citation Europe PMC
Last Modified
23 August 2017