Molecules in this library possessed structural diversity at multiple levels, e.g., different core scaffolds, number of sulfate groups, and position of sulfate groups. NSGMs included five distinct chemical classes of pentasulfated monomeric flavonoid scaffolds (1–2), hexa- and octa- sulfated dimeric flavones (3–9), pentasulfated dimeric flavone-quinazolinones (10–12), undecasulfated trimeric flavones (13 and 14), and dodecasulfated hexabenzoyl inositol derivative (15). GAGs comprised of unfractionated heparin (UFH, 16), enoxaparin (17), and chondroitin sulfate A-C (19–21) in addition to the octasulfated pentasaccharide fondaparinux (18) and the octasulfated disaccharide sucrose octasulfate (22).