Brefeldin A

Brefeldin A
Names
	Preferred IUPAC name (1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f][1]oxacyclotridecin-4-one
	Other names γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone
Identifiers
CAS Number	20350-15-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48080 ;
ChEMBL	ChEMBL19980 ;
ChemSpider	4449949 ;
DrugBank	DB07348 ;
ECHA InfoCard	100.127.053
PubChem CID	5287620;
UNII	XG0D35F9K6 ;
CompTox Dashboard (EPA)	DTXSID00880041 ;
	InChI InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1 Key: KQNZDYYTLMIZCT-KQPMLPITSA-N ; InChI=1/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1 Key: KQNZDYYTLMIZCT-KQPMLPITBH;
	SMILES O=C/1O[C@H](CCC/C=C/[C@H]2[C@H]([C@H](O)/C=C\1)C[C@@H](O)C2)C;
Properties
Chemical formula	C16H24O4
Molar mass	280.36 g/mol
Appearance	White to off-white crystalline powder
Melting point	204 to 205 °C (399 to 401 °F; 477 to 478 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Brefeldin A is a lactone antiviral produced by the fungus Penicillium brefeldianum. Brefeldin A inhibits protein transport from the endoplasmic reticulum to the golgi complex indirectly by preventing association of COP-I coat to the Golgi membrane. Brefeldin A was initially isolated with hopes to become an antiviral drug but is now primarily used in research to study protein transport.