Brefeldin A Properties, Molecular Formula, Applications - WorldOfChemicals

Brefeldin A Properties

Brefeldin A

Brefeldin A Molecular Structure-Molecule Struture
Molecule Structure Image

Description

 

Brefeldin A is a lactone antibiotic produced by fungal organisms such as Eupenicillium brefeldianum. It inhibits transport of proteins from ER to Golgi and induces retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum. This leads to proteins accumulating inside the ER. In mammalian and yeast cells, the main target of brefeldin A appears to be a certain type of GTP-exchange factors responsible for activating a GTPase called Arf1p ; in turn, Arf1p is involved in the formation of transport vesicles by recruiting coat proteins to intracellular membranes. Brefeldin A was initially isolated as an anti-viral antibiotic but is now primarily used in biological research to study protein transport.

Chemical Properties

Appearance White to Off-White Crystalline Powder
Boiling Point 492.7 °C
CAS Number 20350-15-6
ChEBI 48080
Density 1.108 g/cm3
EINECS Number 247-104-4
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]oxacyclotridecin-​4-one
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
InChIKey KQNZDYYTLMIZCT-KQPMLPITSA-N
Melting Point 204-205°C
Molar Mass 280.36 g/mol
Molecular Formula C16H24O4
RTECS Number GY8410000
Synonyms 4H-Cyclopent[f]oxacyclotridecin-4-one,1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-,(1R,2E,6S,10E,11aS,13S,14aR)-;(1R,2E,6S,10E,11αS,13S,14αR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11α,12,13,14,14α-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one;Brefeldin A
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