Pawhuskin A

Pawhuskin A is a naturally occurring prenylated stilbene isolated from Dalea purpurea which acts as a competitive silent antagonist of the κ-, μ-, and δ-opioid receptors (K_e = 203 nM, 570 nM, and 2900 nM, respectively).^[2][3][4] The compound was named after Pawhuska, Oklahoma, a place near where the samples of Dalea purpurea that led to its discovery were taken from.^[4] Other isolates of the plant with affinity for opioid receptors include Pawhuskin B and Pawhuskin C, though these compounds produce comparatively weak opioid receptor displacement (4.2–11.4 μM) relative to Pawhuskin A.^[2][3] Dalea purpurea was used in traditional Native American medicine to treat various ailments, and pawhuskin A and related isolates may be some of the constituents of the plant which underlay this use.^[3]

Pawhuskin A

Names
Preferred IUPAC name 4-[(E)-2-{2-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl}ethen-1-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol
Identifiers
CAS Number	656235-31-3 N[[1]]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL513748
ChemSpider	8541870
PubChem CID	10366422
CompTox Dashboard (EPA)	DTXSID001032044
InChI InChI=1S/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+ Key: LZRXMBPDNILKDO-ZVBRSKEYSA-N InChI=1/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+ Key: LZRXMBPDNILKDO-ZVBRSKEYBQ
SMILES CC(=CCC/C(=C/CC1=C(C=C(C=C1O)O)/C=C/C2=C(C(=C(C=C2)O)O)CC=C(C)C)/C)C
Properties
Chemical formula	C29H36O4
Molar mass	448.603 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• Amentoflavone
• Catechin
• Hyperoside
• Salvinorin A