Structural modifications affect the Km values of UGT1A9-mediated 3-O-glucuronidation. A, Km values were decreased in the presence of 1, substitutions of -OH at positions of C3′ or C4′; 2, -OMe groups at C3′, C4′, C5, or C6; or 3, -Me group at C6. B, Km values were increased by >1-fold with the additions of 2′-OH or 6-OH. The compound numbers are labeled above the abbreviated chemical names.