Domoic Acid

Identification

Generic Name
Domoic Acid
DrugBank Accession Number
DB02852
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 311.3303
Monoisotopic: 311.136887409
Chemical Formula
C15H21NO6
Synonyms
  • (-)-domoic acid
  • L-domoic acid
External IDs
  • NSC-288031

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutamate receptor ionotropic, kainate 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Domoic Acid is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Domoic Acid.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Domoic Acid.
AgomelatineThe risk or severity of CNS depression can be increased when Domoic Acid is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Domoic Acid.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Kainoids
Alternative Parents
Proline and derivatives / L-alpha-amino acids / Tricarboxylic acids and derivatives / Pyrrolidine carboxylic acids / Amino acids / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Aliphatic heteromonocyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Kainoid skeleton
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, tricarboxylic acid, L-proline derivative, pyrrolidinecarboxylic acid (CHEBI:34727) / Kainoids (C13732)
Affected organisms
Not Available

Chemical Identifiers

UNII
M02525818H
CAS number
14277-97-5
InChI Key
VZFRNCSOCOPNDB-AOKDLOFSSA-N
InChI
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
IUPAC Name
(2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
SMILES
[H]\C(\C(\[H])=C(\C)[C@@]1([H])CN[C@]([H])(C(O)=O)[C@@]1([H])CC(O)=O)=C(\[H])[C@@]([H])(C)C(O)=O

References

General References
Not Available
KEGG Compound
C13732
PubChem Compound
5282253
PubChem Substance
46505755
ChemSpider
4445428
ChEBI
34727
ChEMBL
CHEMBL1232313
ZINC
ZINC000003995581
PDBe Ligand
DOQ
Wikipedia
Domoic_acid
PDB Entries
1yae / 2pbw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.759 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity79.03 m3·mol-1Chemaxon
Polarizability31.25 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8955
Blood Brain Barrier+0.5836
Caco-2 permeable-0.6537
P-glycoprotein substrateSubstrate0.6594
P-glycoprotein inhibitor INon-inhibitor0.914
P-glycoprotein inhibitor IINon-inhibitor0.9679
Renal organic cation transporterNon-inhibitor0.8929
CYP450 2C9 substrateNon-substrate0.8777
CYP450 2D6 substrateNon-substrate0.8096
CYP450 3A4 substrateNon-substrate0.5718
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.913
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.918
CYP450 3A4 inhibitorNon-inhibitor0.9855
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9836
Ames testNon AMES toxic0.8572
CarcinogenicityNon-carcinogens0.9473
BiodegradationNot ready biodegradable0.6119
Rat acute toxicity2.4199 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9349
hERG inhibition (predictor II)Non-inhibitor0.9385
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014i-1290000000-8226a83e6258d94ab39c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0hfy-1293000000-5e16636409be17c7e02e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0059000000-f928e7588ef217810ede
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01dl-2690000000-cad3fe5ec15d585330d6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1290000000-b8399fcb6fffc62bb9a2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-6940000000-c8e125de13fdc80093b1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-1003-3490000000-877fec9233cf995fdfd2
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.7145606
predicted
DarkChem Lite v0.1.0
[M-H]-183.2662606
predicted
DarkChem Lite v0.1.0
[M-H]-173.34625
predicted
DeepCCS 1.0 (2019)
[M+H]+195.6495606
predicted
DarkChem Lite v0.1.0
[M+H]+183.3848606
predicted
DarkChem Lite v0.1.0
[M+H]+175.74182
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.7155606
predicted
DarkChem Lite v0.1.0
[M+Na]+183.2129606
predicted
DarkChem Lite v0.1.0
[M+Na]+181.65434
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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 co...
Gene Name
GRIK2
Uniprot ID
Q13002
Uniprot Name
Glutamate receptor ionotropic, kainate 2
Molecular Weight
102582.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52