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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:48 UTC
Update Date2018-03-12 22:03:13 UTC
HMDB IDHMDB0033939
Secondary Accession Numbers
  • HMDB33939
Metabolite Identification
Common NameDomoic acid
DescriptionDomoic acid, also known as domoate, 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. Domoic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, domoic acid is primarily located in the cytoplasm. Outside of the human body, domoic acid can be found in mollusks. This makes domoic acid a potential biomarker for the consumption of this food product. Domoic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic acid, 9ciHMDB
DomoateHMDB
Chemical FormulaC15H21NO6
Average Molecular Weight311.3303
Monoisotopic Molecular Weight311.136887409
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
CAS Registry Number14277-97-5
SMILES
CC(\C=C/C=C(\C)C1CNC(C1CC(O)=O)C(O)=O)C(O)=O
InChI Identifier
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+
InChI KeyVZFRNCSOCOPNDB-VOGDQUTBSA-N
Chemical Taxonomy
DescriptionThis compound 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
Substituents
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.76 g/LALOGPS
logP-0.23ALOGPS
logP-1.8ChemAxon
logS-2.6ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017959
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDomoic acid
METLIN IDNot Available
PubChem Compound54601877
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .