CID 6971145
Basic information
- CAS
52809-07-1- Standard SMILES
[NH3+][C@@H](Cn1oc(=O)[nH]c1=O)C(=O)[O-]- InChIKey
ASNFTDCKZKHJSW-REOHCLBHSA-N- Molecular formula
- C5H7N3O5
- Average molar mass
- 189.13 g/mol
- Monoisotopic mass
- 189.03857033
Overview
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.
Names & identifiers
- Preferred name
- CID 6971145
- IUPAC
- (2S)-2-azaniumyl-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoate
- English name
- Quisqualic acid
- Molecular formula
- C5H7N3O5
- Molecular weight
- 189.13
Names & synonyms
2jbk2or43feeQUISQUALATEQuisqualic acidL-QUISQUALIC ACID(+)-QuisqualicAciQuisqualinic acid()-QUISQUALIC ACID(+)-QUISQUALIC ACIDL(+)-QUISQUALIC ACIDQuisqualic acid (7CI)
Show more names
QUISQUALIC ACID USP/EP/BP
Database identifiers
- CAS
52809-07-1- PubChem CID
- 6971145
Properties
Computed structural properties
- XLogP
- -3.2
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 259
Physicochemical properties
- Melting point
- 185 · 185-187°C dec.
- alpha
- 20 · D20 +17.0° (c = 2.0 in 6M HCl)
- Boiling point
- 324.36 °C · 324.36°C (rough estimate)
- Density
- 1.6649 · 1.6649 (rough estimate)
- refractive index
- 1.619 · 1.6190 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 4 OH · NH4OH 1 M: 20 mg/mL, clear, colorless
- pka
- 2.12 · 2.12±0.10(Predicted)
- form
- powder
- color
- white to off-white
- Water Solubility
- Soluble in ethanol, water. Insoluble in organic solvents.
- Merck
- 13 · 13,8177
- BRN
- 1078734 · 1078734
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- InChI=1/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-/s3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P261-P280h-P301+P312a-P304+P340-P321-P501a
Chemistry & industry
Applications
DescriptionL-Quisqualic acid is a natural analog of glutamate that acts as an agonist at AMPA-selective and metabotropic glutamate receptors (EC50s = 170, 10, 40, and 29 nM at GluR-A, mGluR1, mGluR3, and mGluR5, respectively), as well as the ionotropic kainate receptor (GRIK4; Ki = 6.43 nM). L-Quisqualic acid is used to study receptor dynamics and as an excitotoxin to selectively destroy neurons in the brain or spinal cord.
UsesAn amino acid that is able to function as an agonist at multiple excitatory amino acid receptor substrates in the central nervous system. It also has high affinity for the kainate, AMPA and the metabotropic receptors. Inhibits the Ca2+/Cl-dependent glutamic acid uptake system in brain synaptic plasma membrane preparations.
UsesQuisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons.
UsesQuisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR.
General DescriptionQuisqualate/ Quisqualic acid is obtained from the fruits and seeds of Quisqualis chinensis. It is an agonist at two subsets of excitatory amino acid receptors metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores and, ionotropic receptors that directly control membrane channels. L-quisqualic acid is an agonist of the neurotransmitter L-glutamate.
Additional notes
DefinitionChEBI: Quisqualic acid is a non-proteinogenic alpha-amino acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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