(S)-AMPA

Identification

Name
(S)-AMPA
Accession Number
DB02057  (EXPT00513)
Type
Small Molecule
Groups
Experimental
Description

AMPA is a specific agonist for the AMPA receptor.

Structure
Thumb
Synonyms
  • (S)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
Categories
Not Available
UNII
9280SC28GD
CAS number
83643-88-3
Weight
Average: 186.1653
Monoisotopic: 186.064056818
Chemical Formula
C7H10N2O4
InChI Key
UUDAMDVQRQNNHZ-YFKPBYRVSA-N
InChI
InChI=1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid
SMILES
CC1=C(C[[email protected]](N)C(O)=O)C(O)=NO1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate receptor 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

Synthesis Reference

Wilfried Lubisch, Berthold Behl, Hans-Peter Hofmann, Laszlo Szabo, "Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists." U.S. Patent US6277850, issued June, 1996.

US6277850
General References
Not Available
External Links
PubChem Compound
158397
PubChem Substance
46505942
ChemSpider
139348
BindingDB
17662
ChEMBL
CHEMBL276815
HET
AMQ
Wikipedia
AMPA
PDB Entries
1ftm / 1lb8 / 1my2 / 1p1q / 1p1u / 1p1w / 3dp4 / 3fat

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 Solubility24.5 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.3ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.58 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44 m3·mol-1ChemAxon
Polarizability17.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9774
Blood Brain Barrier-0.5082
Caco-2 permeable-0.701
P-glycoprotein substrateNon-substrate0.5828
P-glycoprotein inhibitor INon-inhibitor0.9802
P-glycoprotein inhibitor IINon-inhibitor0.9972
Renal organic cation transporterNon-inhibitor0.9574
CYP450 2C9 substrateNon-substrate0.8715
CYP450 2D6 substrateNon-substrate0.8076
CYP450 3A4 substrateNon-substrate0.6301
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.5709
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.904
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9532
Ames testNon AMES toxic0.6071
CarcinogenicityNon-carcinogens0.8944
BiodegradationNot ready biodegradable0.7339
Rat acute toxicity2.4011 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9962
hERG inhibition (predictor II)Non-inhibitor0.9661
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

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
Aralkylamines / Isoxazoles / Heteroaromatic compounds / Lactams / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
L-alpha-amino acid / Aralkylamine / Azole / Isoxazole / Heteroaromatic compound / Lactam / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Glutamate receptor 2
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:52