Quisqualate

Identification

Name
Quisqualate
Accession Number
DB02999  (EXPT02735)
Type
Small Molecule
Groups
Experimental
Description

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. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
8OC22C1B99
CAS number
Not Available
Weight
Average: 189.1262
Monoisotopic: 189.038570349
Chemical Formula
C5H7N3O5
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[[email protected]@H](CN1OC(=O)NC1=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate receptor 2Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C08296
PubChem Compound
40539
PubChem Substance
46509075
ChemSpider
37038
BindingDB
17660
ChEBI
8734
ChEMBL
CHEMBL279956
IUPHAR
1372
Guide to Pharmacology
GtP Drug Page
HET
QUS
PDB Entries
1mm6 / 1mm7 / 1p1o / 1s9t / 2al4 / 2jbk / 2or4 / 3b6t / 3fee / 4f29
show 4 more

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 Solubility53.6 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)8.56ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.96 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.51 m3·mol-1ChemAxon
Polarizability15.39 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-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
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

Taxonomy

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
L-alpha-amino acid / 1,2,4-oxadiazole / Azole / Oxadiazole / Heteroaromatic compound / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound / Azacycle
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
non-proteinogenic alpha-amino acid (CHEBI:8734)

Targets

Kind
Protein
Organism
Human
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. [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]
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 December 01, 2017 15:06