You have to do some calculations. 376.22 says the maximum fill is 20% of the area. The total are is 64 square inches and the 20% is 12.8 square inches. Now you have to look to Chaper 9, Table 5. Here you will find that the area of a single 500kcmil THW is 0.7901 square inches. That would permit the installation of 16 conductors of that size. Derating is not required until you have more than 30 current carrying conductors for this application.
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