We extend some results of M. G. Krein to the class of entire functions which can be represented as ratios of discrete Cauchy transforms in the plane. As an application we obtain new versions of de Branges' Ordering Theorem for nearly invariant subspaces in a class of Hilbert spaces of entire functions. Examples illustrating sharpness of the obtained results are given. We also discuss applications to spectral theory of rank one perturbations of normal operators.