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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:48 UTC
Update Date2022-03-07 02:53:54 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. Based on a literature review a significant number of articles have been published on Domoic acid.
Structure
Data?1563862484
Synonyms
ValueSource
DomoateGenerator
2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic acid, 9ciHMDB
4-[(4Z)-6-Carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylateHMDB
Domoic acid, sodium saltHMDB
2 alpha-Carboxy-4 beta-(5-carboxy-1-methyl-1,3 beta-hexadienyl)-3-pyrrolidineacetic acidHMDB
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
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
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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility515.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.73331661259
DarkChem[M-H]-169.66331661259
DeepCCS[M+H]+171.06630932474
DeepCCS[M-H]-168.70830932474
DeepCCS[M-2H]-201.59430932474
DeepCCS[M+Na]+177.15930932474
AllCCS[M+H]+173.532859911
AllCCS[M+H-H2O]+170.432859911
AllCCS[M+NH4]+176.432859911
AllCCS[M+Na]+177.232859911
AllCCS[M-H]-173.732859911
AllCCS[M+Na-2H]-174.132859911
AllCCS[M+HCOO]-174.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Domoic acidCC(\C=C/C=C(\C)C1CNC(C1CC(O)=O)C(O)=O)C(O)=O4549.2Standard polar33892256
Domoic acidCC(\C=C/C=C(\C)C1CNC(C1CC(O)=O)C(O)=O)C(O)=O2353.3Standard non polar33892256
Domoic acidCC(\C=C/C=C(\C)C1CNC(C1CC(O)=O)C(O)=O)C(O)=O2569.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Domoic acid,1TMS,isomer #1C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O)C1CC(=O)O[Si](C)(C)C2696.5Semi standard non polar33892256
Domoic acid,1TMS,isomer #2C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O[Si](C)(C)C)C1CC(=O)O2682.0Semi standard non polar33892256
Domoic acid,1TMS,isomer #3C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CNC(C(=O)O)C1CC(=O)O2715.7Semi standard non polar33892256
Domoic acid,1TMS,isomer #4C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C)C(C(=O)O)C1CC(=O)O2695.3Semi standard non polar33892256
Domoic acid,2TMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CNC(C(=O)O)C1CC(=O)O[Si](C)(C)C2710.3Semi standard non polar33892256
Domoic acid,2TMS,isomer #2C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C2663.2Semi standard non polar33892256
Domoic acid,2TMS,isomer #3C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C)C(C(=O)O)C1CC(=O)O[Si](C)(C)C2702.1Semi standard non polar33892256
Domoic acid,2TMS,isomer #4C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CNC(C(=O)O[Si](C)(C)C)C1CC(=O)O2693.4Semi standard non polar33892256
Domoic acid,2TMS,isomer #5C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O2721.9Semi standard non polar33892256
Domoic acid,2TMS,isomer #6C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CN([Si](C)(C)C)C(C(=O)O)C1CC(=O)O2743.8Semi standard non polar33892256
Domoic acid,3TMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CNC(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C2672.4Semi standard non polar33892256
Domoic acid,3TMS,isomer #2C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CN([Si](C)(C)C)C(C(=O)O)C1CC(=O)O[Si](C)(C)C2696.4Semi standard non polar33892256
Domoic acid,3TMS,isomer #3C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C2675.7Semi standard non polar33892256
Domoic acid,3TMS,isomer #4C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O2730.4Semi standard non polar33892256
Domoic acid,4TMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C2682.1Semi standard non polar33892256
Domoic acid,4TMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C)C1CN([Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C1CC(=O)O[Si](C)(C)C2713.1Standard non polar33892256
Domoic acid,1TBDMS,isomer #1C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O)C1CC(=O)O[Si](C)(C)C(C)(C)C2968.2Semi standard non polar33892256
Domoic acid,1TBDMS,isomer #2C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O2948.1Semi standard non polar33892256
Domoic acid,1TBDMS,isomer #3C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CNC(C(=O)O)C1CC(=O)O2993.3Semi standard non polar33892256
Domoic acid,1TBDMS,isomer #4C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O)C1CC(=O)O2951.5Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CNC(C(=O)O)C1CC(=O)O[Si](C)(C)C(C)(C)C3186.6Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #2C/C(=C\C=C/C(C)C(=O)O)C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C3143.5Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #3C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O)C1CC(=O)O[Si](C)(C)C(C)(C)C3167.5Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #4C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O3159.4Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #5C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O3179.1Semi standard non polar33892256
Domoic acid,2TBDMS,isomer #6C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O)C1CC(=O)O3206.1Semi standard non polar33892256
Domoic acid,3TBDMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C3351.9Semi standard non polar33892256
Domoic acid,3TBDMS,isomer #2C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O)C1CC(=O)O[Si](C)(C)C(C)(C)C3392.2Semi standard non polar33892256
Domoic acid,3TBDMS,isomer #3C/C(=C\C=C/C(C)C(=O)O)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C3353.9Semi standard non polar33892256
Domoic acid,3TBDMS,isomer #4C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O3393.6Semi standard non polar33892256
Domoic acid,4TBDMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C3533.1Semi standard non polar33892256
Domoic acid,4TBDMS,isomer #1C/C(=C\C=C/C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1CN([Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)O[Si](C)(C)C(C)(C)C3488.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Domoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1190000000-0f032ae6ba67e85569d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Domoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-03dr-7022930000-d481676ec3cd8f81e0f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Domoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 10V, Positive-QTOFsplash10-02td-0091000000-5c1af032e2a414093d322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 20V, Positive-QTOFsplash10-00xv-0290000000-3132996b9c637bd2d17c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 40V, Positive-QTOFsplash10-00fu-2950000000-da1336086e7683eca3752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 10V, Negative-QTOFsplash10-03xr-0095000000-a9ef2070f6c85aca77f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 20V, Negative-QTOFsplash10-0300-0091000000-a75b1fa12139c14df40a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 40V, Negative-QTOFsplash10-00di-8090000000-2a54baf57b36bcd8bc7b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 10V, Positive-QTOFsplash10-03di-0397000000-b7d0fe55c6c974e1f0c92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 20V, Positive-QTOFsplash10-014i-0490000000-13675d00d78272887b6f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 40V, Positive-QTOFsplash10-0kdl-8960000000-ec13c78f91642fefe9f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 10V, Negative-QTOFsplash10-03di-0049000000-c759361a83dda185d4032021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 20V, Negative-QTOFsplash10-0aba-4090000000-178917029ca95263d8ae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Domoic acid 40V, Negative-QTOFsplash10-0006-9420000000-8ba7cd4addebc77d8fbc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB017959
KNApSAcK IDC00034487
Chemspider ID32772177
KEGG Compound IDC13732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDomoic acid
METLIN IDNot Available
PubChem Compound54601877
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839381
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.. .