The portrait was one of a several of Madonna painted by Howson
An oil painting depicting Madonna in the nude with her ex-husband Guy Ritchie will go under the hammer in Scotland this week.
Acclaimed Scottish artist Peter Howson has produced several portraits of the pop icon in a state of undress.
Madonna & Guy was painted in 2005. The couple parted last year.
McTear's auction house in Glasgow said it expected the work, sold by a private collector, to fetch up to £22,000 when it goes on sale on Saturday.
In it the singer is reclining and film director Ritchie has a hand on her thigh.
Brian Clements from the auctioneers said: "There is no doubt that the recent split of Madonna and Guy has generated increased interest in the painting.
"The painting created a huge amount of controversy when it was unveiled a few years ago and I think it's safe to say it is one of a kind."
What began in 2000 as a fairytale wedding at Skibo Castle in the Scottish Highlands came to an end in November when the couple were granted a "quickie" divorce.
They share custody of their two boys, Rocco and adopted son David Banda.
The McTear's Scottish Contemporary Art Auction features a host of other works by former official war artist Howson.
Controversial nude portraits of Madonna painted by the Scottish artist were exhibited at a small gallery in Ayrshire in 2002.
Howson was offered substantial sums to open the collection in New York, Paris, Los Angeles or Italy.
But he rejected the approaches in favour of the Maclaurin Art Gallery in Ayr.