I ran a test scenario in Command.
A single Kh-22NA (NATO AS-4 Kitchen B Mod 3) was launched from a Tu-22M3 (NATO Backfire C) at near maximum range.
The target was an industrial plant in Dnipro, Ukraine.
A single Ukrainian S-300V1 (NATO SA-12) SAM battery was set up near the target.
The S-300V1 began engagement (with 2x 9M83 missiles) when the Kh-22NA was at about 16 nm from the target, and descending below about 28,000 feet.
The Kh-22NA was intercepted with 1x 9M83 SAM at about 9.7 nm from the target, while moving at 1499 kt and at 17,330 feet.
I thought the scenario was interesting given the recent tragic Kh-22 strike in Dnipro and the widespread claims (by Ukraine and others) that Ukraine has no capability to defend against Kh-22.
I didn't think that sounded technically correct, given that Ukraine does possess the S-300V1 and it was designed to defend against such weapons as Lance, Pershing and SRAM.
The Kh-22 is certainly a challenging target, but the S-300V1 is at least technically capable of defending against it. (On "paper" or in a sim like this, of course. Caveats apply.)
Still interested in what you might find in HCE.