Quisqualic Acid

HCID 40539CAS 52809-07-1
Substructure searchFind similar structures

Basic information

Standard SMILES
N[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
189.03857032

Overview

Quisqualic acid is a non-proteinogenic alpha-amino acid.

Names & identifiers

Preferred name
Quisqualic Acid
IUPAC
(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
English name
Quisqualic acid
Molecular formula
C5H7N3O5
Molecular weight
189.13

Names & synonyms

QUISQUALIC ACID52809-07-1DTXSID208969278OC22C1B991,2,4-Oxadiazolidine-2-propanoic acid, alpha-amino-3,5-dioxo-, (S)-(2S)-2-azaniumyl-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoateRefChem:389258DTXCID601326364QuisqualateL-Quisqualic acid(+)-Quisqualic acid(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Show more names
(+)-QuisqualicAci()-QUISQUALIC ACIDL(+)-QUISQUALIC ACIDQuisqualic acid (7CI)QUISQUALIC ACID USP/EP/BP
Quisqualinic acid[3H]quisqualate(S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acidL-quisqualic-acid1mm7MFCD00069337C5H7N3O5CHEMBL168279

Database identifiers

CAS
52809-07-1
PubChem CID
40539
DTXSID
DTXSID20896927
ChEMBL
CHEMBL168279、CHEMBL279956
ChEBI
CHEBI:8734
UNII
8OC22C1B99
EC Number
637-070-2
Nikkaji
J9.726H

Properties

Computed structural properties

XLogP
-3.9
Topological polar surface area
122 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
13

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

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

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (41.2%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

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

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs that bind to and activate excitatory amino acid receptors.
Applications · 5 items

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.

Suppliers50 total

湖北万得化工有限公司15377098680 15377098680 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: Quisqualic acid is a non-proteinogenic alpha-amino acid.

Related reactions

2 records
New reaction record

Linked notes

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