Domoic Acid

Identification

Name
Domoic Acid
Accession Number
DB02852  (EXPT01248)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (-)-domoic acid
  • L-domoic acid
External IDs
NSC-288031
Categories
UNII
M02525818H
CAS number
14277-97-5
Weight
Average: 311.3303
Monoisotopic: 311.136887409
Chemical Formula
C15H21NO6
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate receptor ionotropic, kainate 2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Domoic Acid is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Domoic Acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Domoic Acid.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Domoic Acid.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Domoic Acid is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Domoic Acid.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Domoic Acid.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Domoic Acid.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Domoic Acid.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Domoic Acid.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C13732
PubChem Compound
5282253
PubChem Substance
46505755
ChemSpider
4445428
ChEBI
34727
ChEMBL
CHEMBL1232313
HET
DOQ
Wikipedia
Domoic_acid
PDB Entries
1yae / 2pbw

Clinical Trials

Clinical Trials
Not Available

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
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
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)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:24