In Mr. Monk and the Three Pies we meet Adrian's brother Ambrose. When Captain Stottlemeyer comes to Ambrose's house Ambrose gives him a cup of coffee with a number 6 on the mug.
Adrian explains that the number is to represent where the mug should go in the cupboard (between 5 and 7).
Was Monk's mother also OCD, that she needed to have the mugs in a certain order, or was Adrian's and Ambrose's need for order such that she numbered the mugs so that her two sons wouldn't have to agonize about which mug went where?
Update: From the transcript
00:35:06 Why is it numbered?
00:35:07 Mother numbered ..
00:35:09 So we'd always put them back in the right order.
00:35:11 Of course she did.