The fungal strain AAJ2 isolated from Sediment samples of the mangrove ecosystem of Nizampatnam, Andhra Pradesh was explored for bioactive metabolites with anti-microbial, anti-inflammatory and anti cancer potential. The fungal strain AAJ2 has shown potential biological activities in the preliminary screening of secondary metabolites, and identified as Penicillium chrysogenum AAJ2 (OQ569546) by ITS region analysis . Methanolic crude extract of AAJ2 reported anti-oxidative activity with DPPH with an IC50 value of 28.67 µg/ml and superoxide free radical scavenging activity with an IC50 value 12.41 µg/ml , 5LOX enzyme inhibition by 19.62% at 5mg/ml, 78.20 % of HRBC membrane stability and 41.10% of inhibition of MCF-7 cell lines at 120 µl. GC-MS and HPLC metabolite fingerprinting of methanolic extract of AAJ2 followed by insilico molecular docking studies of the identified bioactive compounds were checked for affinity with human proteome using Swiss target prediction and also predicted potential anti-cancer and anti-inflammatory properties. Our investigation revealed that 7-hydroxyjanthinone, Shearinines B, Citrinin, Janthinone and Tetradecane are significant compounds of P. chrysogenum AAJ2 strain, a novel marine fungus and are responsible for various pharmacological activities.