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Record Information
Creation Date2014-08-29 04:54:45 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4040
Common NameDomoic acid
ClassSmall Molecule
DescriptionIsodomoic acid F is found in mollusks. Isodomoic acid F is isolated from mussels.
Compound Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic acid, 9CI
Chemical FormulaC15H21NO6
Average Molecular Mass311.330 g/mol
Monoisotopic Mass311.137 g/mol
CAS Registry Number14277-97-5
IUPAC Name4-[(2E,4Z)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
Traditional Name4-[(2E,4Z)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
InChI IdentifierInChI=1/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+
Chemical Taxonomy
Description belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentKainoids
Alternative Parents
  • Kainoid skeleton
  • Proline or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
AppearanceWhite powder.
Experimental Properties
Melting Point213°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
Water Solubility0.76 g/LALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)11.59ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity79.03 m³·mol⁻¹ChemAxon
Polarizability31.37 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1190000000-0f032ae6ba67e85569d1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03dr-7022930000-d481676ec3cd8f81e0f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02td-0091000000-5c1af032e2a414093d32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xv-0290000000-3132996b9c637bd2d17cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-2950000000-da1336086e7683eca375View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0095000000-a9ef2070f6c85aca77f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0300-0091000000-a75b1fa12139c14df40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-8090000000-2a54baf57b36bcd8bc7bView in MoNA
Toxicity Profile
Route of ExposureIngestion
Mechanism of ToxicityDomoic acid acts as a neurotoxin. It induces excitotoxicity by an integrative action on ionotropic glutamate receptors at both sides of the synapse for which it has high affinity, preferentially the KA subtype, coupled with an effect that prevents the channel from rapid desensitization. DOM crosses the placenta and can be detected in milk, opening the possibility of a risk for fetal and neonatal exposure.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIsodomoic acid F is found in mollusks. Isodomoic acid F is isolated from mussels.
Minimum Risk LevelNot Available
Health EffectsExposure to domoic acid causes short-term memory loss, brain damage (including epilepsy), in severe cases, death. It may also cause kidney damage – even at levels considered safe for human consumption.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02852
PubChem Compound ID54601877
ChemSpider IDNot Available
UniProt IDNot Available
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDomoic_acid
Synthesis ReferenceNot Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available


General Function:
Kainate selective glutamate receptor activity
Specific Function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2 (By similarity).
Gene Name:
Uniprot ID:
Molecular Weight:
102582.475 Da
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  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]