CHEBI:34727 - domoic acid

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ChEBI Name domoic acid
ChEBI ID CHEBI:34727
Definition An 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB2359498, eMolecules:27514934, ZINC000003995581
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Formula C15H21NO6
Net Charge 0
Average Mass 311.334
Monoisotopic Mass 311.13689
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:txid41953) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
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.
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 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 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 acid ChemIDplus
Manual Xrefs Databases
C00034487 KNApSAcK
C13732 KEGG COMPOUND
DB02852 DrugBank
Domoic_acid Wikipedia
DOQ PDBeChem
FDB012146 FooDB
HMDB0033939 HMDB
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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
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Last Modified
03 August 2021