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CHEBI:34727 - domoic acid

Default Structure
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:
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.
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.
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.
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