Navigation

name Structure Reference Source Properties Activities Metabolism

5-(Aminomethyl)-3(2H)-isoxazolone 

AlkaPlorer ID: AK007601

Synonym: Pantherine, Agarin, Muscimol, Pyroibotenic acid, β-Toxin

IUPAC Name: 5-(aminomethyl)-1,2-oxazol-3-one

Structure

SMILES: NCC1=CC(=O)NO1

copy

InChI: InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)

copy

InChIKey: ZJQHPWUVQPJPQT-UHFFFAOYSA-N

copy

Source

Species Genus Family Order Class Phylum Kingdom Domain
Amanita muscaria Amanita Amanitaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota

Properties Information

Molecule Weight: 114.10399999999998

TPSA？: 72.02000000000001

MolLogP？: -0.5734000000000001

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Felis catus Felis catus Activity nan None 10.1021/jm00187a022
Felis catus Felis catus Relative potency nan None 10.1021/jm00149a012
Homo sapiens Cerebroside-sulfatase Potency 2393.4 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Potency 39810.7 nM None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 44668.4 nM None
Homo sapiens GABA-A receptor; agonist GABA site EC50 27000.0 nM 10.1021/ml300476v
Homo sapiens GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 537.03 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 537.03 nM 10.1021/jm301473k
Homo sapiens GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 540.0 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 540.0 nM 10.1021/jm301473k
Homo sapiens GABA A receptor alpha-2/beta-2/gamma-2 EC50 407.38 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA A receptor alpha-2/beta-2/gamma-2 EC50 407.38 nM 10.1021/jm301473k
Homo sapiens GABA A receptor alpha-2/beta-2/gamma-2 EC50 410.0 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA A receptor alpha-2/beta-2/gamma-2 EC50 410.0 nM 10.1021/jm301473k
Homo sapiens GABA A receptor alpha-2/beta-2/gamma-2 Rmax 99.0 % 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA A receptor alpha-3/beta-2/gamma-2 EC50 210.0 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA A receptor alpha-3/beta-2/gamma-2 EC50 210.0 nM 10.1021/jm301473k
Homo sapiens GABA A receptor alpha-3/beta-2/gamma-2 EC50 213.8 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA A receptor alpha-3/beta-2/gamma-2 EC50 213.8 nM 10.1021/jm301473k
Homo sapiens GABA A receptor alpha-3/beta-2/gamma-2 Rmax 97.0 % 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA-A receptor; anion channel IC50 2.0 nM 10.1021/jm00100a015
Homo sapiens GABA-A receptor; anion channel IC50 16.0 nM 10.1021/jm058018d
Homo sapiens GABA-A receptor; anion channel IC50 135.0 nM 10.1021/jm00100a015
Homo sapiens GABA-A receptor; anion channel Ki 6.0 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA-A receptor; anion channel Ki 11.0 nM 10.1021/jm00180a029
Homo sapiens GABA receptor rho-1 subunit EC50 691.83 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA receptor rho-1 subunit EC50 691.83 nM 10.1021/jm301473k
Homo sapiens GABA receptor rho-1 subunit EC50 700.0 nM 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA receptor rho-1 subunit EC50 700.0 nM 10.1021/jm301473k
Homo sapiens GABA receptor rho-1 subunit EC50 1400.0 nM 10.1021/jm7015842
Homo sapiens GABA receptor rho-1 subunit EC50 2300.0 nM 10.1021/ml300476v
Homo sapiens GABA receptor rho-1 subunit Kd 2300.0 nM 10.1021/jm9904349
Homo sapiens GABA receptor rho-1 subunit Rmax 98.0 % 10.1016/j.ejmech.2014.07.039
Homo sapiens GABA receptor rho-2 subunit Kd 1400.0 nM 10.1021/jm9904349
Homo sapiens Histone deacetylase 6 Inhibition -20.29 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -5.04 % 10.6019/CHEMBL4808148
Homo sapiens Lysine-specific demethylase 4D-like Potency 22387.2 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 31622.8 nM None
Mus musculus Mus musculus Activity nan None 10.1021/jm00187a022
Mus musculus Mus musculus ED50 0.25 mg.kg-1 10.1021/jm00180a029
Mus musculus Mus musculus ED50 0.7 mg.kg-1 10.1021/jm00122a025
Mus musculus Mus musculus ED50 1.34 mg.kg-1 10.1021/jm00187a022
Mus musculus Mus musculus ED50 1.5 mg.kg-1 10.1021/jm00122a025
Mus musculus Mus musculus ED50 2.0 mg.kg-1 10.1021/jm00180a029
Mus musculus Mus musculus ID50 0.76 mg.kg-1 10.1021/jm00146a024
Mus musculus Mus musculus LD50 4.2 mg.kg-1 10.1021/jm00122a025
Mus musculus Mus musculus LD50 17.0 mg.kg-1 10.1021/jm00180a029
Rattus norvegicus GABA-A receptor; anion channel Displacement 86.0 % 10.1021/jm00139a005
Rattus norvegicus GABA-A receptor; anion channel IC50 3.0 nM 10.1021/jm00146a024
Rattus norvegicus GABA-A receptor; anion channel IC50 3.2 nM 10.1021/jm00184a017
Rattus norvegicus GABA-A receptor; anion channel IC50 5.0 nM 10.1021/jm00149a012
Rattus norvegicus GABA-A receptor; anion channel IC50 6.0 nM 10.1021/jm000371q
Rattus norvegicus GABA-A receptor; anion channel IC50 6.0 nM 10.1021/jm00149a012
Rattus norvegicus GABA-A receptor; anion channel IC50 6.0 nM 10.1021/jm020027o
Rattus norvegicus GABA-A receptor; anion channel IC50 10.0 nM 10.1021/jm00387a031
Rattus norvegicus GABA-A receptor; anion channel Inhibition 0.004 % 10.1021/jm50001a020
Rattus norvegicus GABA-A receptor; anion channel Inhibition nan % 10.1021/jm50001a020
Rattus norvegicus GABA-A receptor; anion channel Ki 4.0 nM 10.1021/jm00180a029
Rattus norvegicus GABA-A receptor; anion channel Relative affinity 6.3 None 10.1021/jm00184a017
Rattus norvegicus GABA receptor alpha-2 subunit Control 124.0 % 10.1021/jm00122a025
Rattus norvegicus GABA receptor gamma-1 subunit IC50 6.0 nM 10.1021/jm00149a012
Rattus norvegicus GABA transporter IC50 320000.0 nM 10.1021/jm00149a012
Rattus norvegicus Gamma-amino-N-butyrate transaminase Inhibition nan % 10.1021/jm50001a020
Rattus norvegicus Glutamate decarboxylase 67 kDa isoform Inhibition nan % 10.1021/jm50001a020
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 28183.8 nM None
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm00187a022
Rattus norvegicus Rattus norvegicus Decrease of spontaneous firing rate 1e-06 M 10.1021/jm00146a024
Rattus norvegicus Rattus norvegicus ED70 16.0 mg kg-1 10.1021/jm00187a022
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 25.84 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 27.42 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -3.29 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.17 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.09 % 10.6019/CHEMBL4495565
Sus scrofa D-amino-acid oxidase IC50 100000.0 nM 10.1021/jm800200u
Trypanosoma brucei 6-phospho-1-fructokinase Potency 756.9 nM None
None ADMET Binding energy 11.9 kCal mol-1 10.1021/jm00378a021
None ADMET LD50 3.2 mg.kg-1 10.1021/jm00122a025
None No relevant target pKa 4.78 None 10.1021/jm00187a022
None Unchecked Activity 90.0 % 10.1021/np50094a001
None Unchecked Activity nan None 10.1021/jm300353r
None Unchecked Activity nan None 10.1039/C5MD00442J
None Unchecked EC50 53.7 nM 10.1016/j.ejmech.2014.07.039
None Unchecked EC50 53.7 nM 10.1021/jm301473k
None Unchecked EC50 54.0 nM 10.1016/j.ejmech.2014.07.039
None Unchecked EC50 54.0 nM 10.1021/jm301473k
None Unchecked EC50 620.0 nM 10.1021/jm070447j
None Unchecked EC50 630.96 nM 10.1021/jm070447j
None Unchecked EC50 1698.24 nM 10.1039/C5MD00442J
None Unchecked EC50 2000.0 nM 10.1021/ml300476v
None Unchecked EC50 2040.0 nM 10.1039/C5MD00442J
None Unchecked EC50 2200.0 nM 10.1021/jm070447j
None Unchecked EC50 24000.0 nM 10.1021/jm070447j
None Unchecked EC50 25118.86 nM 10.1021/jm070447j
None Unchecked EC50 501187233627271.44 nM 10.1021/jm070447j
None Unchecked Kd 15.2 nM 10.1016/j.bmc.2013.06.063
None Unchecked Ki 2.6 nM 10.1021/np50094a001
None Unchecked Ki 7.0 nM 10.1021/jm301473k
None Unchecked Rmax 114.0 % 10.1016/j.ejmech.2014.07.039
None Unchecked RUmax 96.0 % 10.1021/jm070447j
None Unchecked RUmax 101.0 % 10.1021/jm070447j
None Unchecked RUmax 104.0 % 10.1021/jm070447j

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT020205 N[C@H](C(=O)O)c1cc(O)no1>>NCc1cc(O)no1 RXN-21515