The first trnasition is obviously an irregular one. The duct is expanding on the horizontal dimension and at the same time contracting on the vertical dimension. Area- or velocity-wise this may be considered as an unsymmetrical expanding transition fitting. This system might have to be installed that way due to physical constraints or for other practical considerations, it loss is definitely not easy or impossible to estimate!
The designer should strive to design and arrange duct fittings according to some fitting standards or database so the system loss can be estimated. These are ASHRAE Duct Fitting Database (2009), ASHRAE Fundamentals Handbooks, SMACNA HVAC Systems Duct Design or other technical handbooks or texts.
Notice too the AR (Aspect Ratio) of the transitioned piece is 42:4 or 10.5:1. This is considered bad design. The designer should strive to achieve an AR of ? 3:1. In addition to increased surface area, insulation and weight of metal, friction rate and operating cost increase as AR increases.