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
DrugInteractionDrug group
AcetyldigitoxinDomoic Acid may increase the arrhythmogenic activities of Acetyldigitoxin.Approved
AcetyldigoxinDomoic Acid may increase the arrhythmogenic activities of Acetyldigoxin.Experimental
AmikacinAmikacin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational, Vet Approved
ApramycinApramycin may increase the respiratory depressant activities of Domoic Acid.Experimental, Vet Approved
ArbekacinArbekacin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational
AzosemideAzosemide may decrease the neuromuscular blocking activities of Domoic Acid.Investigational
BekanamycinBekanamycin may increase the respiratory depressant activities of Domoic Acid.Experimental
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
Botulinum Toxin Type BDomoic Acid may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved, Investigational
BumetanideBumetanide may decrease the neuromuscular blocking activities of Domoic Acid.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Domoic Acid.Approved
ChlortetracyclineChlortetracycline may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational, Vet Approved
ChlorthalidoneChlorthalidone may decrease the neuromuscular blocking activities of Domoic Acid.Approved
ClindamycinClindamycin may increase the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
ColistimethateColistimethate may increase the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational, Vet Approved
CymarinDomoic Acid may increase the arrhythmogenic activities of Cymarin.Experimental
DemeclocyclineDemeclocycline may increase the neuromuscular blocking activities of Domoic Acid.Approved
DeslanosideDomoic Acid may increase the arrhythmogenic activities of Deslanoside.Approved
DibekacinDibekacin may increase the respiratory depressant activities of Domoic Acid.Experimental
DigitoxinDomoic Acid may increase the arrhythmogenic activities of Digitoxin.Approved, Investigational
DigoxinDomoic Acid may increase the arrhythmogenic activities of Digoxin.Approved
Digoxin Immune Fab (Ovine)Domoic Acid may increase the arrhythmogenic activities of Digoxin Immune Fab (Ovine).Approved
DihydrostreptomycinDihydrostreptomycin may increase the respiratory depressant activities of Domoic Acid.Investigational, Vet Approved
DoxycyclineDoxycycline may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational, Vet Approved
Etacrynic acidEtacrynic acid may decrease the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
FramycetinFramycetin may increase the respiratory depressant activities of Domoic Acid.Approved
FurosemideFurosemide may decrease the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
GeneticinGeneticin may increase the respiratory depressant activities of Domoic Acid.Experimental
GentamicinGentamicin may increase the respiratory depressant activities of Domoic Acid.Approved, Vet Approved
GENTAMICIN C1AGENTAMICIN C1A may increase the respiratory depressant activities of Domoic Acid.Experimental
GitoformateDomoic Acid may increase the arrhythmogenic activities of Gitoformate.Experimental
HydroflumethiazideHydroflumethiazide may decrease the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
Hygromycin BHygromycin B may increase the respiratory depressant activities of Domoic Acid.Vet Approved
IsepamicinIsepamicin may increase the respiratory depressant activities of Domoic Acid.Experimental
KanamycinKanamycin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational, Vet Approved
Lanatoside CDomoic Acid may increase the arrhythmogenic activities of Lanatoside C.Experimental
LincomycinLincomycin may increase the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
LithiumLithium may increase the neuromuscular blocking activities of Domoic Acid.Approved
Magnesium hydroxideMagnesium hydroxide may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
Magnesium oxideMagnesium oxide may increase the neuromuscular blocking activities of Domoic Acid.Approved
Magnesium salicylateMagnesium salicylate may increase the neuromuscular blocking activities of Domoic Acid.Approved
Magnesium sulfateMagnesium sulfate may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational, Vet Approved
MethyclothiazideMethyclothiazide may decrease the neuromuscular blocking activities of Domoic Acid.Approved
MetildigoxinDomoic Acid may increase the arrhythmogenic activities of Metildigoxin.Experimental
MicronomicinMicronomicin may increase the respiratory depressant activities of Domoic Acid.Experimental
MinocyclineMinocycline may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
NeamineNeamine may increase the respiratory depressant activities of Domoic Acid.Experimental
NeomycinNeomycin may increase the respiratory depressant activities of Domoic Acid.Approved, Vet Approved
NetilmicinNetilmicin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational
OleandrinDomoic Acid may increase the arrhythmogenic activities of Oleandrin.Experimental, Investigational
OuabainDomoic Acid may increase the arrhythmogenic activities of Ouabain.Approved
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational, Vet Approved
ParomomycinParomomycin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational
PeruvosideDomoic Acid may increase the arrhythmogenic activities of Peruvoside.Experimental
PiretanidePiretanide may decrease the neuromuscular blocking activities of Domoic Acid.Approved
PirlimycinPirlimycin may increase the neuromuscular blocking activities of Domoic Acid.Vet Approved
PlazomicinPlazomicin may increase the respiratory depressant activities of Domoic Acid.Investigational
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
ProcainamideProcainamide may increase the neuromuscular blocking activities of Domoic Acid.Approved
ProscillaridinDomoic Acid may increase the arrhythmogenic activities of Proscillaridin.Experimental
PuromycinPuromycin may increase the respiratory depressant activities of Domoic Acid.Experimental
QuinethazoneQuinethazone may decrease the neuromuscular blocking activities of Domoic Acid.Approved
QuinidineQuinidine may increase the neuromuscular blocking activities of Domoic Acid.Approved, Investigational
QuinineQuinine may increase the neuromuscular blocking activities of Domoic Acid.Approved
RibostamycinRibostamycin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational
SisomicinSisomicin may increase the respiratory depressant activities of Domoic Acid.Investigational
StreptomycinStreptomycin may increase the respiratory depressant activities of Domoic Acid.Approved, Vet Approved
TetracyclineTetracycline may increase the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
TobramycinTobramycin may increase the respiratory depressant activities of Domoic Acid.Approved, Investigational
TorasemideTorasemide may decrease the neuromuscular blocking activities of Domoic Acid.Approved
TrichlormethiazideTrichlormethiazide may decrease the neuromuscular blocking activities of Domoic Acid.Approved, Vet Approved
VancomycinVancomycin may increase the neuromuscular blocking activities of Domoic Acid.Approved
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 June 02, 2018 07:08