Explore a selection of our essential drug information below, or:
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
Structure for Quisqualic acid (DB02999)
- Weight
- Average: 189.1262
Monoisotopic: 189.038570349 - Chemical Formula
- C5H7N3O5
- Synonyms
- Quisqualate
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AMetabotropic glutamate receptor 1 agonistHumans AGlutamate receptor ionotropic, kainate 1 inhibitorHumans AMetabotropic glutamate receptor 2 inhibitorHumans AMetabotropic glutamate receptor 3 inhibitorHumans AMetabotropic glutamate receptor 5 inhibitorHumans AGlutamate carboxypeptidase 2 inhibitorHumans UGlutamate receptor 2 Not Available Humans UGlutamate receptor ionotropic, kainate 2 Not Available Humans - 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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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
- External Links
- 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
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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
Property Value Source Water Solubility 53.6 mg/mL ALOGPS logP -2.7 ALOGPS logP -3.7 Chemaxon logS -0.55 ALOGPS pKa (Strongest Acidic) 1.46 Chemaxon pKa (Strongest Basic) 8.55 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 121.96 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 36.51 m3·mol-1 Chemaxon Polarizability 15.17 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8794 Blood Brain Barrier + 0.6701 Caco-2 permeable - 0.683 P-glycoprotein substrate Non-substrate 0.5426 P-glycoprotein inhibitor I Non-inhibitor 0.966 P-glycoprotein inhibitor II Non-inhibitor 0.9974 Renal organic cation transporter Non-inhibitor 0.9551 CYP450 2C9 substrate Non-substrate 0.8294 CYP450 2D6 substrate Non-substrate 0.8331 CYP450 3A4 substrate Non-substrate 0.6195 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.6392 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9938 Ames test Non AMES toxic 0.528 Carcinogenicity Non-carcinogens 0.8977 Biodegradation Not ready biodegradable 0.8637 Rat acute toxicity 2.2084 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9632 hERG inhibition (predictor II) Non-inhibitor 0.9335
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.2792188 predictedDarkChem Lite v0.1.0 [M-H]- 140.27214 predictedDeepCCS 1.0 (2019) [M+H]+ 140.6999188 predictedDarkChem Lite v0.1.0 [M+H]+ 143.19742 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.4144188 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.90193 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling activates a phosphatidylinositol-calcium second messenger system. May participate in the central action of glutamate in the CNS, such as long-term potentiation in the hippocampus and long-term depression in the cerebellum (PubMed:24603153, PubMed:28886343, PubMed:7476890). May function in the light response in the retina (By similarity)
- Specific Function
- Adenylate cyclase inhibiting g protein-coupled glutamate receptor activity
- Gene Name
- GRM1
- Uniprot ID
- Q13255
- Uniprot Name
- Metabotropic glutamate receptor 1
- Molecular Weight
- 132355.855 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ionotropic glutamate receptor that functions as a cation-permeable ligand-gated ion channel, gated by L-glutamate and the glutamatergic agonist kainic acid. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
- Specific Function
- Glutamate-gated calcium ion channel activity
- Gene Name
- GRIK1
- Uniprot ID
- P39086
- Uniprot Name
- Glutamate receptor ionotropic, kainate 1
- Molecular Weight
- 103979.665 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. May mediate suppression of neurotransmission or may be involved in synaptogenesis or synaptic stabilization
- Specific Function
- Calcium channel regulator activity
- Gene Name
- GRM2
- Uniprot ID
- Q14416
- Uniprot Name
- Metabotropic glutamate receptor 2
- Molecular Weight
- 95566.715 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling inhibits adenylate cyclase activity
- Specific Function
- Calcium channel regulator activity
- Gene Name
- GRM3
- Uniprot ID
- Q14832
- Uniprot Name
- Metabotropic glutamate receptor 3
- Molecular Weight
- 98878.05 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling activates a phosphatidylinositol-calcium second messenger system and generates a calcium-activated chloride current. Plays an important role in the regulation of synaptic plasticity and the modulation of the neural network activity
- Specific Function
- A2a adenosine receptor binding
- Gene Name
- GRM5
- Uniprot ID
- P41594
- Uniprot Name
- Metabotropic glutamate receptor 5
- Molecular Weight
- 132467.635 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Has both folate hydrolase and N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) activity. Has a preference for tri-alpha-glutamate peptides. In the intestine, required for the uptake of folate. In the brain, modulates excitatory neurotransmission through the hydrolysis of the neuropeptide, N-aceylaspartylglutamate (NAAG), thereby releasing glutamate. Involved in prostate tumor progression
- Specific Function
- Ac-asp-glu binding
- Gene Name
- FOLH1
- Uniprot ID
- Q04609
- Uniprot Name
- Glutamate carboxypeptidase 2
- Molecular Weight
- 84330.015 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ionotropic glutamate receptor that functions as a ligand-gated cation channel, gated by L-glutamate and glutamatergic agonists such as alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA), quisqualic acid, and kainic acid (PubMed:20614889, PubMed:31300657, PubMed:8003671). L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system and plays an important role in fast excitatory synaptic transmission (PubMed:14687553). Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse upon entry of monovalent and divalent cations such as sodium and calcium (PubMed:20614889, PubMed:8003671). The receptor then desensitizes rapidly and enters in a transient inactive state, characterized by the presence of bound agonist (By similarity). In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of L-glutamate (By similarity). Through complex formation with NSG1, GRIP1 and STX12 controls the intracellular fate of AMPAR and the endosomal sorting of the GRIA2 subunit toward recycling and membrane targeting (By similarity)
- Specific Function
- Ampa glutamate receptor activity
- Gene Name
- GRIA2
- Uniprot ID
- P42262
- Uniprot Name
- Glutamate receptor 2
- Molecular Weight
- 98820.32 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- Ionotropic glutamate receptor that functions as a cation permeable ligand-gated ion channel, gated by L-glutamate and the glutamatergic agonist kainic acid. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist (PubMed:14511640, PubMed:28180184, PubMed:34375587, PubMed:7536611, PubMed:8730589). Modulates cell surface expression of NETO2. In association with GRIK3, involved in presynaptic facilitation of glutamate release at hippocampal mossy fiber synapses (By similarity)
- Specific Function
- Extracellularly glutamate-gated ion channel activity
- Gene Name
- GRIK2
- Uniprot ID
- Q13002
- Uniprot Name
- Glutamate receptor ionotropic, kainate 2
- Molecular Weight
- 102582.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 August 26, 2024 19:22