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DHβE   Click here for help

GtoPdb Ligand ID: 4006

Synonyms: dihydro-β-erythroidine
PDB Ligand
Compound class: Synthetic organic
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 38.77
Molecular weight 275.15
XLogP -0.52
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC1CC=C2C3(C1)N(CC2)CCC1=C3CC(=O)OC1
Isomeric SMILES CO[C@H]1CC=C2[C@]3(C1)N(CC2)CCC1=C3CC(=O)OC1
InChI InChI=1S/C16H21NO3/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13/h2,13H,3-10H2,1H3/t13-,16-/m0/s1
InChI Key ALSKYCOJJPXPFS-BBRMVZONSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Commonly used antagonists at nicotinic acetylcholine receptor α2 subunit α2β2: DHβE (KB = 0.9 μM), tubocurarine (KB = 1.4 μM); α2β4: DHβE (KB = 3.6 μM), tubocurarine (KB = 4.2 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α3 subunit α3β2: DHβE (KB = 1.6 μM, IC50 = 2.0 μM), tubocurarine (KB = 2.4 μM); α3β4: DHβE (KB = 19 μM, IC50 = 26 μM), tubocurarine (KB = 2.2 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α4 subunit α4β2: DHβE (KB = 0.1 μM; IC50 = 0.08 - 0.9 μM), tubocurarine (KB = 3.2 μM, IC50 = 34 μM); α4β4: DHβE (KB = 0.01 μM, IC50 = 0.19 – 1.2 μM), tubocurarine (KB = 0.2 μM, IC50 = 50 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α6 subunit α6/α3β2β3 chimera: DHβE (IC50 = 1.1 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α7 subunit (α7)5: DHβE (IC50 = 8 - 20 μM); (α7)5: tubocurarine (IC50 = 3.1 μM)