Considering the worth of developing non-steroidal compounds for better management of estrogen linked pathologies including contraception, the present work was envisaged to seek rational possibilities in this area through precision based cheminformatics & pharmacological approaches. In foremost portion of the project, bioactive molecules were theoretically modeled through in silico approaches for deducing pharmacophores. The generated models showed importance of different biophore features for estrogenic activity. In the experimental section, a plant named tape-vine with documented ethno-therapeutic uses was evaluated for its contraceptive and estrogenic properties, judging the upcoming possibility of herbal resources to play significant role in healthcare. The sample was found to possess post-coital pregnancy interceptive activity through restriction of implantation & involvement of uterotrophic & hormonal effects. This specimen also demonstrated favorable effects on lipid and carbohydrate profiles suggesting its safe nature. Phytochemicals abundant in this plant specimen were also classified for estrogenic activities through models developed in theoretical section of this study.