The macrocycles with the features of large cavity, optical property and CPL response to guest simultaneously are rarely reported but very attractive based on their potential application. Herein, a macrocycle (BiCDB-MC) with dynamically racemic feature, inwardly directed functional groups, a large hollow with size of 1.3 nm and fluorescent property was designed and synthesized. BiCDB-MC was found to have two equally chiral conformations and was dynamically racemic in solution based on their rapidly interconvertion via macrocycle flipping. It was interesting that BiCDB-MC exhibited a selective turn-on CPL response with glum = 0.00248 toward ursolic acid since one of the stable chiral conformations could form a more stable inclusion complex. This kind of turn-on CPL emission for dynamical-racemic macrocycle with CPL recognition for complicated natural chiral compound was described for the first time.