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CHEBI:34727 - domoic acid

ChEBI IDCHEBI:34727
ChEBI Namedomoic acid
Stars
DefinitionAn L-proline derivative 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 produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP).
Last Modified3 August 2021
DownloadsMolfile
FormulaC15H21NO6
Net Charge0
Average Mass311.334
Monoisotopic Mass311.13689
SMILESC/C(=C/C=C/[C@@H](C)C(=O)O)[C@H]1CN[C@H](C(=O)O)[C@H]1CC(=O)O
InChIInChI=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
InChIKeyVZFRNCSOCOPNDB-AOKDLOFSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Pseudo-nitzschia (ncbitaxon:41953) - PubMed (28817087)
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
neurotoxin  A poison that interferes with the functions of the nervous system.
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.
algal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
Application:
neuromuscular agent  A drug used for its actions on skeletal muscle.
ChEBI Ontology
Outgoing Relation(s)
domoic acid (CHEBI:34727) has role algal metabolite (CHEBI:84735)
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)
domoic acid (CHEBI:34727) is conjugate acid of domoate(2−) (CHEBI:167470)
Incoming Relation(s)
domoate(2−) (CHEBI:167470) is conjugate base of domoic acid (CHEBI:34727)
IUPAC Name 
(3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline
Synonym  Source
L-domoic acidChemIDplus
Manual XrefsDatabases
C00034487KNApSAcK
C13732KEGG COMPOUND
DB02852DrugBank
Domoic_acidWikipedia
DOQPDBeChem
FDB012146FooDB
HMDB0033939HMDB
Registry NumbersSources
Reaxys:5126272Reaxys
CAS:14277-97-5ChemIDplus
CAS:14277-97-5KEGG COMPOUND
Citations