Although chirality is critical for molecular properties and functions, experimental quantification of chirality is lacking. Herein, we performed cyclic voltammetry (CV) under polarized magnetic fields to provide a unified scale to quantify and compare DNA chirality. We observed the largest electron spin polarization in DNA structures with opposite chiral senses, which is consistent with the effect of chiral-induced spin selectivity (CISS). Spin polarization is weaker among DNA topologies of the same chiral arrangement, with DNA triplexes exhibiting the strongest CISS. Within DNA duplexes, spin polarization is further reduced depending on the sequence, with fewer guanine-cytosine (GC) pairs displaying a weaker CISS likely due to localized variations in chirality. Surprisingly, spin polarization is vectorial along the DNA duplex while presenting the smallest variation when the transportation directions of electrons become opposite. The four factors, chiral sense, topology, sequence, and directionality of electron transportation, delineate hierarchical contributions to molecular chirality, with profound implications ranging from spintronics to molecular recognitions.