Where are these drain plugs located?
At the risk of stating the obvious (your post doesn't suggest that you're sure about this)....
The main oil supply is in a housing that surrounds the crankcase with the filler tube and cap at the front. The drain plug for it should be located near where the oil filter goes in. If no oil drains out when you remove that plug, either you have no oil in the tank, or there's some serious blockage in there.
The only "rear" plug I can think of would be the transmission drain plug.
Do you have a manual for this bike?
As you stated, the oiling system is similar to other Enfields, with one difference. You have a feed pump that pulls oil from the tank, through the filter, and into the big end of the connecting rod. Also splashing some onto the cylinder wall. After sucking excess oil from the crankcase, the return pump on your engine pumps most of it up to the valve rockers, and from there, into the cam tunnel and timing chest, from there draining back into the oil tank. .
The twin cylinder engines use the feed pump for supplying all oil to the engine, and the return pump is only there to return it to the tank. The twins also have a screw that plugs a small hole in the crankcase, but I'd hesitate to call that a "drain plug".
The illustrations I have available of your engine don't show that little screw, so I'm making the assumption that the rear plug you're talking about is the transmission plug.
If your engine does have a screw into the crankcase, and you're seeing oil come out this hole, then perhaps your "return pump" isn't working.
Determining if the pumps are working on a big twin is easy; you just remove the oil filler cap and look into the hole to see spurts of oil coming out the return pipe into the tank.
There's a similar pipe on the 250 single, but it only returns oil from the pressure relief valve, so I can't say how much oil you'd see coming out that, or even if it's visible in the filler neck like it is in the twins.