Gastrochilus calceolaris (Buch.-Ham. ex Sm.) D.Don, commonly known as the shoe-shaped belly-lip orchid, is a rare monopodial epiphytic orchid of high medicinal value. The present study provides the first integrated morpho-anatomical and metabolic profiling of this critically endangered species. Morphological and anatomical observations revealed distinct xerophytic adaptations, including a thick cuticle, well-developed velamen and prominent vascular bundles, which enable drought tolerance. Preliminary phytochemical screening of the methanolic leaf extract confirmed the presence of diverse secondary metabolites, including alkaloids, flavonoids, tannins and phenols. Gas Chromatography-Mass Spectrometry (GC-MS) identified 43 phytoconstituents, of which major compounds such as 3-Heptyn-1-ol and 3-heptyn-1-ol are known for their antioxidant, antifungal and anti-inflammatory activities. These findings highlight the pharmacological and conservation significance of G. calceolaris, providing a baseline for future bioprospecting and in vitro conservation strategies.