Quisqualic acid

Identification

Generic Name
Quisqualic acid
DrugBank Accession Number
DB02999
Background

Quisqualic acid is an agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 189.1262
Monoisotopic: 189.038570349
Chemical Formula
C5H7N3O5
Synonyms
  • Quisqualate

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutamate receptor 2Not AvailableHumans
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Heteroaromatic compounds / 1,2,4-oxadiazoles / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
1,2,4-oxadiazole / Amine / Amino acid / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxylic acid / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
non-proteinogenic alpha-amino acid (CHEBI:8734)
Affected organisms
Not Available

Chemical Identifiers

UNII
8OC22C1B99
CAS number
52809-07-1
InChI Key
ASNFTDCKZKHJSW-REOHCLBHSA-N
InChI
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
IUPAC Name
(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
SMILES
N[C@@H](CN1OC(=O)NC1=O)C(O)=O

References

General References
Not Available
KEGG Compound
C08296
PubChem Compound
40539
PubChem Substance
46509075
ChemSpider
37038
BindingDB
17660
ChEBI
8734
ChEMBL
CHEMBL279956
ZINC
ZINC000000897456
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
QUS
Wikipedia
Quisqualic_acid
PDB Entries
1mm6 / 1mm7 / 1p1o / 1s9t / 2al4 / 2jbk / 2or4 / 3b6t / 4f29 / 4f2o
show 14 more

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 Solubility53.6 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.7Chemaxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.46Chemaxon
pKa (Strongest Basic)8.55Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area121.96 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity36.51 m3·mol-1Chemaxon
Polarizability15.17 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8794
Blood Brain Barrier+0.6701
Caco-2 permeable-0.683
P-glycoprotein substrateNon-substrate0.5426
P-glycoprotein inhibitor INon-inhibitor0.966
P-glycoprotein inhibitor IINon-inhibitor0.9974
Renal organic cation transporterNon-inhibitor0.9551
CYP450 2C9 substrateNon-substrate0.8294
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.6195
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.6392
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9938
Ames testNon AMES toxic0.528
CarcinogenicityNon-carcinogens0.8977
BiodegradationNot ready biodegradable0.8637
Rat acute toxicity2.2084 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9632
hERG inhibition (predictor II)Non-inhibitor0.9335
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-MSsplash10-0006-9700000000-cdbb0447baea6cf0a050
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-d274e567f32b90a7fb10
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0pb9-1900000000-073fd3e062cb304aba00
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0f6x-9400000000-4e74b9e5a103d1d784ce
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-9dab1fdcb07990f940d4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000x-9000000000-34b02468030bb668a5a3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-1900000000-5ab867b5a18eb1229eb3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052b-9800000000-cfeb579c27669811b225
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-066s-9000000000-d99325633514ef6efe81
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-066u-9000000000-f7fb4e823850a13074de
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-74f6d03b633e00df7157
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-1900000000-52642d4aa31305121e49
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-62ba517caa1efa951e89
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-dc5a2a314a5ea5f1c761
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00tf-5900000000-e1c9c6c06aab4dc5c9d7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9400000000-c984c5390d47e2bfb679
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-9000000000-18a5d4b4da3797704144
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-86bc7c9743cb39cd2b42
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]-140.2792188
predicted
DarkChem Lite v0.1.0
[M-H]-140.27214
predicted
DeepCCS 1.0 (2019)
[M+H]+140.6999188
predicted
DarkChem Lite v0.1.0
[M+H]+143.19742
predicted
DeepCCS 1.0 (2019)
[M+Na]+140.4144188
predicted
DarkChem Lite v0.1.0
[M+Na]+151.90193
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ionotropic glutamate receptor activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA2
Uniprot ID
P42262
Uniprot Name
Glutamate receptor 2
Molecular Weight
98820.32 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]
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