My understanding is that, for the purposes of determining fair use, a derivative work is substantially the same thing but in a different format. Transformative work must involve significant additional creative contribution "Changing the medium of a work is a derivative use rather than a transformative one." They cite previous case law that holds repackaging a print book as an e-book as a "paradigmatic example of a derivative work." The law also offers some paradigmatic examples of transformative work, such as criticism, commentary and scholarship.
Based on all of that, I would guess that, for the purposes of copyright law, a JPEG of a painting is absolutely a derivative work and not a transformative one.
on edit: actually I also think that a JPEG of the Mona Lisa is derivative, but just noting that the value we ascribe to the Mona Lisa is something like the concept of Mana for art https://medium.com/luminasticity/art-as-a-tool-for-storing-m...