oxycodegol   Click here for help

GtoPdb Ligand ID: 10652

Synonyms: loxicodegol (deleted INN) | NKTR-181 | NKTR181
Compound class: Synthetic organic
Comment: Oxycodegol (NKTR-181; Nektar Therapeutics) is a μ-opioid receptor agonist analgesic [3]. It was designed to enter the brain slowly, so as to reduce CNS-mediated side effects and abuse potential.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 20
Topological polar surface area 106.54
Molecular weight 595.34
XLogP -0.47
No. Lipinski's rules broken 1
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Canonical SMILES COCCOCCOCCOCCOCCOCCO[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC)O
Isomeric SMILES COCCOCCOCCOCCOCCOCCO[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC)O
InChI InChI=1S/C31H49NO10/c1-32-9-8-30-27-23-4-5-24(35-3)28(27)42-29(30)25(6-7-31(30,33)26(32)22-23)41-21-20-40-19-18-39-17-16-38-15-14-37-13-12-36-11-10-34-2/h4-5,25-26,29,33H,6-22H2,1-3H3/t25-,26+,29-,30-,31+/m0/s1
Bioactivity Comments
Oxycodegol (NKTR-181) is selective for μ receptor over δ and κ receptors, although its affinity for μ receptors is lower compared to the affinities of morphine and oxycodone [3].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
μ receptor Hs Agonist Agonist 6.6 pKi - 3
pKi 6.6 (Ki 2.37x10-7 M) [3]
Description: Competitive membrane binding assay measuring displacement [3H]naloxone from human μ receptors expressed by CHO cells.
δ receptor Hs Agonist Agonist 5.4 pKi - 3
pKi 5.4 (Ki 4.15x10-6 M) [3]
Description: Competitive membrane binding assay measuring displacement [3H]DPDPE from human δ receptors expressed by CHO cells.