BU72   Click here for help

GtoPdb Ligand ID: 9363

Synonyms: compound 10 (Husbands and Lewis, 1995) [4]
PDB Ligand
Compound class: Synthetic organic
Comment: BU72 was reported as a long-lasting μ receptor agonist [5]. Its very high affinity meant that it was not considered as a clinical candidate. Strong lipophilic binding interactions with the μ receptor confer slow receptor kinetics, and therefore long duration of action.
We revised the chemical structure in March 2021, based on data arising from analysis of the crystal structure of the BU72/μ receptor complex that was deposited to the Protein Data Bank (5C1M) [2-3]. This shows that the (β-phenyl) group of BU72 shoud be in the (R) configuration. BU72 has been used in a number of studies to model the μ receptor activation process [1,6].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 44.73
Molecular weight 428.25
XLogP 3.03
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CO[C@@]12C=C[C@@]34[C@@]5([C@@H]1N[C@@H]([C@]2(C)C3)c1ccccc1)CCN([C@@H]4Cc1c5cc(O)cc1)C
Isomeric SMILES CO[C@@]12C=C[C@@]34[C@@]5([C@@H]1N[C@@H]([C@]2(C)C3)c1ccccc1)CCN([C@@H]4Cc1c5cc(O)cc1)C
InChI InChI=1S/C28H32N2O2/c1-25-17-26-11-12-28(25,32-3)24(29-23(25)18-7-5-4-6-8-18)27(26)13-14-30(2)22(26)15-19-9-10-20(31)16-21(19)27/h4-12,16,22-24,29,31H,13-15,17H2,1-3H3/t22-,23-,24+,25+,26-,27+,28+/m1/s1
InChI Key RGJHUVJQGAAZLK-GKTFKBBASA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R,3S,3aR,5aR,6R,11bR,11cS)-3a-methoxy-3,14-dimethyl-2-phenyl-2,3,3a,6,7,11c-hexahydro-1H-6,11b-(epiminoethano)-3,5a-methanonaphtho[2,1-g]indol-10-ol
Synonyms Click here for help
compound 10 (Husbands and Lewis, 1995) [4]
Database Links Click here for help
CAS Registry No. 173265-76-4 (source: SciFinder)
GtoPdb PubChem SID 328083465
RCSB PDB Ligand VF1
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