PSB-SB-487

PSB-SB-487
Identifiers
	IUPAC name 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one;
CAS Number	1399049-81-0;
PubChem CID	70678101;
ChemSpider	28667155;
ChEMBL	ChEMBL2181542;
CompTox Dashboard (EPA)	DTXSID401045358 ;
Chemical and physical data
Formula	C26H32O4
Molar mass	408.538 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1;
	InChI InChI=1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3; Key:YNWOMOUVWNKICO-UHFFFAOYSA-N;

PSB-SB-487 is an experimental drug which is used as a pharmacological research tool. It is a coumarin derivative which is an antagonist at the former orphan receptor GPR55. Unlike older GPR55 antagonists such as O-1918, PSB-SB-487 has good selectivity over the related receptor GPR18, with an IC₅₀ of 113nM at GPR55 vs 12500nM at GPR18.^[1] However it has poorer selectivity over other related receptors, acting as a weak antagonist at CB₁ with a Ki of 1170nM, and a partial agonist at CB₂ with a Ki of 292nM.^[2]

References

^ Rempel V, Volz N, Gläser F, Nieger M, Bräse S, Müller CE (June 2013). "Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold". Journal of Medicinal Chemistry. 56 (11): 4798–810. doi:10.1021/jm4005175. PMID 23679955.
^ Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, et al. (September 2012). "7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists". Journal of Medicinal Chemistry. 55 (18): 7967–77. doi:10.1021/jm3008213. PMID 22916707.

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[1] Rempel V, Volz N, Gläser F, Nieger M, Bräse S, Müller CE (June 2013). "Antagonists for the orphan G-protein-coupled receptor GPR55 based on a coumarin scaffold". Journal of Medicinal Chemistry. 56 (11): 4798–810. doi:10.1021/jm4005175. PMID 23679955.

[pmid22916707-2] Rempel V, Volz N, Hinz S, Karcz T, Meliciani I, Nieger M, et al. (September 2012). "7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists". Journal of Medicinal Chemistry. 55 (18): 7967–77. doi:10.1021/jm3008213. PMID 22916707.

[1]

[2]

Identifiers

IUPAC name 7-(1,1-Dimethyloctyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2-one
CAS Number	1399049-81-0
PubChem CID	70678101
ChemSpider	28667155
ChEMBL	ChEMBL2181542
CompTox Dashboard (EPA)	DTXSID401045358
Chemical and physical data
Formula	C₂₆H₃₂O₄
Molar mass	408.538 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC1=C(CC2=CC3=C(C=C(C(C)(C)CCCCCCC)C=C3O)OC2=O)C=CC=C1
InChI InChI=1S/C26H32O4/c1-4-5-6-7-10-13-26(2,3)20-16-23(28)21-15-19(25(29)30-24(21)17-20)14-18-11-8-9-12-22(18)27/h8-9,11-12,15-17,27-28H,4-7,10,13-14H2,1-3H3 Key:YNWOMOUVWNKICO-UHFFFAOYSA-N

PSB-SB-487

See also

References