Our contribution to the process of 2D to 3D structure conversion was in the realization of algorithmically deterministic z-coordinate (out-of-plane) displacement, guided by the 2D stereobonds. This process mimics the thought process that chemists use to interpret the 2Dstructures. For all acyclic stereobonds leading from an atom, the connected fragment (determined by the breadth-first graph traversal) was rotated out of plane depending on the number of adjacent atoms out of the plane of drawing (Figure ). We chose ±60° for when the substituent was attached to an atom with two adjacent atoms, and ±90° for three adjacent atoms (Figure ) (see Figure ). Since no deterministic rotation of endocyclic bonds could be devised, the atoms in respective bonds are subjected to simple out-of-plane displacement of the participating atoms (Figure ). The endpoints of a wedged bond are shifted out of plane only if the wedge points towards them, whereas both atoms are displaced in bold/hash style bonds. The z-coordinate adjustments by rotations or translations allowed the displacement of the coordinates in the correct direction toward the desired minimum after a geometry optimization (Figure ). This practically eliminated the cases of unanticipated configurational inversion upon a forcefield minimization (See the Supporting Information 3.2). It proved useful in the context of axial and planar chirality interpretation into 3D representation wherein no simple designators can typically be assigned and enforced by ChemDraw™ or related packages (Figure ). We purposefully avoided the use of any stereochemical designators (e.g. R/S), so that all stereogenic elements can be encoded in the same way, regardless of designator availability.