Np mrd loader

Record Information
Version2.0
Created at2022-04-28 19:05:04 UTC
Updated at2022-04-28 19:05:04 UTC
NP-MRD IDNP0073863
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Domoic acid
Description (-)-Domoic acid is found in Alsidium corallinum, Chondria armata, Mytilus edulis , Nitzschia pungens and Pseudo-nitzschia multistriata. (-)-Domoic acid was first documented in 1998 (PMID: 10223629).
Structure
Thumb
Synonyms
ValueSource
L-Domoic acidChEBI
L-DomoateGenerator
DomoateGenerator
2 alpha-Carboxy-4 beta-(5-carboxy-1-methyl-1,3 beta-hexadienyl)-3-pyrrolidineacetic acidMeSH
Domoic acid, sodium saltMeSH
Chemical FormulaC15H21NO6
Average Mass311.3303 Da
Monoisotopic Mass311.13689 Da
IUPAC Name(2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
Traditional Namedomoic acid
CAS Registry NumberNot Available
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
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-/t9-,10+,11-,13+/m1/s1
InChI KeyVZFRNCSOCOPNDB-AOKDLOFSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alsidium corallinum-
Chondria armata-
Mytilus edulis-
Nitzschia pungensChromalveolata
Pseudo-nitzschia multistriataLOTUS Database
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
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ChemAxon
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
Polarizability31.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02852
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012146
KNApSAcK IDC00034487
Chemspider IDNot Available
KEGG Compound IDC13732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDomoic_acid
METLIN IDNot Available
PubChem Compound5282253
PDB IDNot Available
ChEBI ID34727
Good Scents IDNot Available
References
General References
  1. Ramsey UP, Douglas DJ, Walter JA, Wright JL: Biosynthesis of domoic acid by the diatom Pseudo-nitzschia multiseries. Nat Toxins. 1998;6(3-4):137-46. [PubMed:10223629 ]
  2. Pulido OM: Domoic acid toxicologic pathology: a review. Mar Drugs. 2008 May 28;6(2):180-219. doi: 10.3390/md20080010. [PubMed:18728725 ]
  3. Kumar KP, Kumar SP, Nair GA: Risk assessment of the amnesic shellfish poison, domoic acid, on animals and humans. J Environ Biol. 2009 May;30(3):319-25. [PubMed:20120452 ]
  4. Zhang XW, Zhang ZX: Quantification of domoic acid in shellfish samples by capillary electrophoresis-based enzyme immunoassay with electrochemical detection. Toxicon. 2012 May;59(6):626-32. doi: 10.1016/j.toxicon.2012.02.011. Epub 2012 Mar 1. [PubMed:22406515 ]
  5. Funk JA, Janech MG, Dillon JC, Bissler JJ, Siroky BJ, Bell PD: Characterization of renal toxicity in mice administered the marine biotoxin domoic Acid. J Am Soc Nephrol. 2014 Jun;25(6):1187-97. doi: 10.1681/ASN.2013080836. Epub 2014 Feb 8. [PubMed:24511141 ]