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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H21NO6
Molecular Weight 311.3303
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of DOMOIC ACID

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

InChIKey=VZFRNCSOCOPNDB-AOKDLOFSSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H21NO6
Molecular Weight 311.3303
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Domoic acid is one of the best-known marine toxins, causative of important neurotoxic alterations. In the year 1987, domoic acid was responsible for four deaths and the illness of more than 100 people after consuming blue mussels (Mytilus edulis) harvested in the Cardigan Bay of Prince Edward Island, Canada. The symptomatology comprised three kinds of signs: gastrointestinal (nausea, vomiting,), cardiovascular (unstable blood pressure and arrhythmias), and neurological signs (disorientation, confusion, hallucinations, coma, and memory impairment). After this event was discovered the domoic acid epileptic. Nearly a year after the amnesic shellfish poisoning event, an 84 years old male survivor re-experienced severe seizures and was diagnosed with temporal lobe epilepsy caused by domoic acid intoxication. This toxin has a high affinity for the glutamate receptors (GluRs) subtypes: alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and KA receptors. The binding of domoic acid to receptors provokes an increase of calcium (Ca2+) levels, causing the release of Glu to the extracellular space, and the activation of N-methyl-d-aspartate (NMDA) receptors. The histological consequences of these cellular alterations comprise astrocytosis, cytoskeletal disarrangement and, finally, cell death.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis of a series of aryl kainic acid analogs and evaluation in cells stably expressing the kainate receptor humGluR6.
1996 Sep 13
Glutathione levels modulate domoic acid induced apoptosis in mouse cerebellar granule cells.
2007 Dec
Domoic acid induces direct DNA damage and apoptosis in Caco-2 cells: recent advances.
2008 Dec
Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7.
2008 Jul 24
Transcriptional responses of xenobiotic metabolizing enzymes, HSP70 and Na+/K+ -ATPase in the liver of rabbitfish (Siganus oramin) intracoelomically injected with amnesic shellfish poisoning toxin.
2008 Jun
Muscarinic receptors prevent oxidative stress-mediated apoptosis induced by domoic acid in mouse cerebellar granule cells.
2009 Apr
DDT exposure of zebrafish embryos enhances seizure susceptibility: relationship to fetal p,p'-DDE burden and domoic acid exposure of California sea lions.
2009 Jan
Gene expression profiles in zebrafish brain after acute exposure to domoic acid at symptomatic and asymptomatic doses.
2009 Jan
Domoic acid induces a long-lasting enhancement of CA1 field responses and impairs tetanus-induced long-term potentiation in rat hippocampal slices.
2009 Sep
Zebrafish seizure model identifies p,p -DDE as the dominant contaminant of fetal California sea lions that accounts for synergistic activity with domoic acid.
2010 Apr
Low-level domoic acid protects mouse cerebellar granule neurons from acute neurotoxicity: role of glutathione.
2013 Apr
Influences of domoic Acid exposure on cardiac development and the expression of cardiovascular relative genes in zebrafish (Daniorerio) embryos.
2015 Jun
Patents

Sample Use Guides

Heart alterations in rats: 2.5 mg/kg
Route of Administration: Intraperitoneal
In mouse cerebellar granule neurons (CGNs) domoic acid (DomA) induces neuronal cell death, either by apoptosis or by necrosis, depending on its concentration, with apoptotic damage predominating in response to low concentrations (100 nM). DomA-induced apoptosis is due to selective activation of AMPA/kainate receptors, and is mediated by DomA-induced oxidative stress, leading to mitochondrial dysfunction and activation of caspase-3
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:09:56 UTC 2023
Edited
by admin
on Sat Dec 16 05:09:56 UTC 2023
Record UNII
M02525818H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOMOIC ACID
HSDB   MI  
Common Name English
L-DOMOIC ACID
Common Name English
(-)-DOMOIC ACID
Common Name English
NSC-288031
Code English
3-PYRROLIDINEACETIC ACID, 2-CARBOXY-4-((1Z,3E,5R)-5-CARBOXY-1-METHYL-1,3-HEXADIEN-1-YL)-, (2S,3S,4S)-
Common Name English
(2S-(2.ALPHA.,3.BETA.,4.BETA.(1Z,3E,5R)))-2-CARBOXY-4-(5-CARBOXY-1-METHYL-1,3-HEXADIENYL)-3-PYRROLIDINEACETIC ACID
Common Name English
DOMOIC ACID [MI]
Common Name English
DOMOIC ACID [HSDB]
Common Name English
Classification Tree Code System Code
BAD BUG BOOK DA
Code System Code Type Description
MERCK INDEX
m4736
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY Merck Index
CHEBI
34727
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
MESH
C012301
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
FDA UNII
M02525818H
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
HSDB
7242
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
CAS
14277-97-5
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
NSC
288031
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID20274180
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
WIKIPEDIA
DOMOIC ACID
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
PUBCHEM
5282253
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
DRUG BANK
DB02852
Created by admin on Sat Dec 16 05:09:56 UTC 2023 , Edited by admin on Sat Dec 16 05:09:56 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST