Sphaeranthus Amaranthoide, commonly known as "Sivakaranthai" in Tamil. The pharmacological evaluation of this plant extract shows antibiotic, anti-inflammatory and analgesic activities, also exhibit anti-bacterial activity against Gram-positive as well as Gram-negative bacteria. This plant extract is also used by herbal practitioners towards the treatment of specific cancer. The present research has been carried out to identify the potential leads towards the treatment of cancer. As the first attempt, we identified two major compounds, Decahydro-6-(iminomethyl)-4a-methylnaphthalen-2-ol and its isomer with MW:195Da using LCMS technique from the Sivakaranthai-whole plant collected during Panguni-uthiram, a full moon day. This identification activity has been presented and published as a poster at 62 nd American Society for Mass Spectrometry (ASMS) conference on Mass Spectrometry and Allied Topics held during June 15 -19, 2014 at Baltimore, Maryland, USA. Subsequently, the identification of phytochemicals has been carried out for the Sivakaranthai whole plant collected during the other normal day and three major compounds with MW: 516Da, MW: 360Da and 374Da are identified. Further, this study has been extended to Sivakaranthai-kulithailam and the molecular masses of the four major phytoconstituents identified are MW: 390Da, MW: 254Da two isomers and MW: 315Da, reported in this research article. Induced fit docking study has been carried out for all the four identified compounds and it was found that the compound with molecular mass 516Da binds better than that of co-crystal and all other three compounds with the breast cancer target -phosphoglycerate dehydrogenase (PHGDH) (PDB ID: 5NZP).