HU-336

HU-336
Identifiers
	IUPAC name (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-1H-benzo[c]chromene-1,4(6H)-dione;
CAS Number	19542-59-7 ;
PubChem CID	11370880;
ChemSpider	9545797 ;
UNII	UT665EY7F2;
CompTox Dashboard (EPA)	DTXSID401029796 ;
Chemical and physical data
Formula	C21H28O3
Molar mass	328.452 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\2C=1OC([C@H]3[C@H](C=1C(=O)/C=C/2CCCCC)C/C(=C\C3)C)(C)C;
	InChI InChI=1S/C21H28O3/c1-5-6-7-8-14-12-17(22)18-15-11-13(2)9-10-16(15)21(3,4)24-20(18)19(14)23/h9,12,15-16H,5-8,10-11H2,1-4H3/t15-,16-/m1/s1 ; Key:GOZGLSHDDOJPJS-HZPDHXFCSA-N ;
	(verify)

HU-336 is a strongly antiangiogenic compound, significantly inhibiting angiogenesis at concentrations as low as 300 nM. It inhibits angiogenesis by directly inducing apoptosis of vascular endothelial cells without changing the expression of pro- and antiangiogenic cytokines and their receptors. HU-336 is highly effective against tumor xenografts in nude mice. Although it is technically the oxidized quinone of delta-8 THC, it is entirely non psychoactive.^[1]

References

^ Kogan NM, Blázquez C, Alvarez L, Gallily R, Schlesinger M, Guzmán M, Mechoulam R (July 2006). "A cannabinoid quinone inhibits angiogenesis by targeting vascular endothelial cells". Molecular Pharmacology. 70 (1): 51–9. doi:10.1124/mol.105.021089. PMID 16571653. S2CID 4830577.

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[1] Kogan NM, Blázquez C, Alvarez L, Gallily R, Schlesinger M, Guzmán M, Mechoulam R (July 2006). "A cannabinoid quinone inhibits angiogenesis by targeting vascular endothelial cells". Molecular Pharmacology. 70 (1): 51–9. doi:10.1124/mol.105.021089. PMID 16571653. S2CID 4830577.

[1]

Identifiers

IUPAC name (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-1H-benzo[c]chromene-1,4(6H)-dione
CAS Number	19542-59-7^Y
PubChem CID	11370880
ChemSpider	9545797^Y
UNII	UT665EY7F2
CompTox Dashboard (EPA)	DTXSID401029796
Chemical and physical data
Formula	C₂₁H₂₈O₃
Molar mass	328.452 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C\2C=1OC([C@H]3[C@H](C=1C(=O)/C=C/2CCCCC)C/C(=C\C3)C)(C)C
InChI InChI=1S/C21H28O3/c1-5-6-7-8-14-12-17(22)18-15-11-13(2)9-10-16(15)21(3,4)24-20(18)19(14)23/h9,12,15-16H,5-8,10-11H2,1-4H3/t15-,16-/m1/s1^Y Key:GOZGLSHDDOJPJS-HZPDHXFCSA-N^Y
(verify)

HU-336

See also

References