column file_name format a50;
column tablespace_name format a15;
column highwater format 9999999999;
set pagesize 9999

select a.tablespace_name
,a.file_name
,(b.maximum+c.blocks-1)*d.db_block_size highwater
from dba_data_files a
,(select file_id,max(block_id) maximum
from dba_extents
group by file_id) b
,dba_extents c
,(select value db_block_size
from v$parameter
where name='db_block_size') d
where a.file_id = b.file_id
and c.file_id = b.file_id
and c.block_id = b.maximum
order by a.tablespace_name,a.file_name
/

The query gives the high water mark for each of the file beyond which they cannot be reduced by size.