Structure via PubChem · Public domain (PubChem)
herkinorin
Sign in to saveHerkinorin is an opioid analgesic that is an analogue of the natural product salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds of which salvinorin A is a member.
Chemical data
- Formula
- C28H30O8
- Molecular weight
- 494.5 g/mol
- IUPAC name
- methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-benzoyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
- SMILES
- C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]1C(=O)[C@H](C[C@H]2C(=O)OC)OC(=O)C4=CC=CC=C4)C)C5=COC=C5
- InChIKey
- PYDQMXRFUVDCHC-XAGHGKQISA-N
- XLogP
- 4.2
- Polar surface area
- 109 Ų
- H-bond donors
- 0
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 494.194068
Show 3 more facts
- chemical formula
- C₂₈H₃₀O₈
- canonical SMILES
- CC12CCC3C(=O)OC(CC3(C1C(=O)C(CC2C(=O)OC)OC(=O)C4=CC=CC=C4)C)C5=COC=C5
- isomeric SMILES
- C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]1C(=O)[C@H](C[C@H]2C(=O)OC)OC(=O)C4=CC=CC=C4)C)C5=COC=C5
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Herkinorin is an opioid analgesic that is an analogue of the natural product salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds of which salvinorin A is a member.
Unlike salvinorin A, which is a selective κ-opioid receptor agonist with no significant μ-opioid receptor affinity, herkinorin is predominantly a μ-opioid receptor agonist. Compared to salvinorin A, herkinorin has 47× lower affinity for κ-opioid receptors (Ki = 90 nM vs Ki = 1.9 nM), and at least 25× higher affinity for μ-opioid receptors (Ki = 12 nM vs Ki >1000 nM), where it acts as a full agonist (IC50 = 0.5 μM, Emax = 130% vs DAMGO). Herkinorin is a semi-synthetic compound, made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, since, while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.
Excerpted from Wikipedia’s “herkinorin” article, available under the CC BY-SA 4.0 licence.