GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

S(+)-apomorphine   Click here for help

GtoPdb Ligand ID: 8285

Synonyms: S-apomorphine | S-(+)-apomorphine
PDB Ligand
Compound class: Synthetic organic
Comment: S(+)-apomorphine a brain-penetrating activator of the activator of the nuclear erythroid 2-related-factor 2 (Nrf2)-ARE (antioxidant response element) pathway [1]. This compound is a receptor-inactive enantiomer of the clinically approved dopamine-receptor agonist apomorphine (R(-)-apomorphine).
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 43.7
Molecular weight 267.13
XLogP 2.86
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
Click here for help

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/)

✖
Canonical SMILES CN1CCc2c3C1Cc1ccc(c(c1c3ccc2)O)O
Isomeric SMILES CN1CCc2c3[C@@H]1Cc1ccc(c(c1c3ccc2)O)O
InChI InChI=1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m0/s1
InChI Key VMWNQDUVQKEIOC-ZDUSSCGKSA-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/)

For advanced searching click here to open chemical structure editor

Similar Ligands Click here for help
Br-BTHIQ
Click here for ligand page
(S)-reticuline
Click here for ligand page
isocorypalmine
Click here for ligand page
N-methyllaurotetanine
Click here for ligand page
neferine
Click here for ligand page
tetrandrine
Click here for ligand page
Targets
KCa1.1; KCa2.2; KCa2.3
SG-094
Click here for ligand page
Targets
TPC2
SG-005
Click here for ligand page
Targets
TPC2
(-)-stepholidine
Click here for ligand page
Targets
D1 receptor; D2 receptor; D5 receptor
tubocurarine
Click here for ligand page
Targets
5-HT3A; 5-HT3AB; KCa2.1; KCa2.2; KCa2.3; Organic cation transporter 2; ZAC ; nicotinic acetylcholine receptor α1 subunit; nicotinic acetylcholine receptor α10 subunit; nicotinic acetylcholine receptor α2 subunit; nicotinic acetylcholine receptor α3 subunit; nicotinic acetylcholine receptor α4 subunit; nicotinic acetylcholine receptor α7 subunit; nicotinic acetylcholine receptor α8 subunit (avian); nicotinic acetylcholine receptor α9 subunit
(-)-N-porphynorapomorphine
Click here for ligand page
Targets
D2 receptor; D3 receptor
N-propylnorapomorphine
Click here for ligand page
Targets
D1 receptor; D5 receptor
apomorphine
Click here for ligand page
Targets
α2A-adrenoceptor; α2B-adrenoceptor; α2C-adrenoceptor; 5-HT1A receptor; 5-HT2A receptor; 5-HT2B receptor; 5-HT2C receptor; D1 receptor; D2 receptor; D3 receptor; D4 receptor; D5 receptor; TRPA1