C371 Chemical Informatics I
SMILES Exercise 2: SMILES as input in the real world

Updated: 25 September 2004

Draw the Isatin molecule below:

Perform both an exact search and a substructure search for the substance. HINT: the search options for the structure searches are below the drawing window. You may have to scroll down to find them.

How many did answers did you find in each case?

Substructure:
Exact:

One of the answers found in the substructure search should be Isatin. Look at that answer. Is it exactly like the molecule you drew for the search? Did you find it when you did an exact search? If not, why do you think it was missed?

Note that the Fisher record provides both an IR spectrum for the Isatin entry. Look at the IR spectrum. Note that you can zoom in on parts of the spectrum, and that you can get the actual values for the peaks by moving your mouse over the spectrum.
What is the value of the highest peak?

Click on the 3D Model option. When the molecule appears, hold down the left mouse, and move it around all three axes.
Try the "View molecule using a plugin" option. Download the file to your computer, use Wordpad to open it, and obtain a printout to hand in with your answers. What kind of file is this?

2. Change the file type of the file to .mol, using the procedure that was sent to you on Oncourse mail.

Now try to open the file. Did it open and display a 2-D structure? If so, obtain a printout. What program opened it?

Now use the ViewerLite program that should be on your computer. (Get it from the IU Chemistry SciFinder Scholar download site if not.) Open the file.

Try all of the options under the Tools menu of ViewerLite. Obtain a printout of the molecule from ViewLite.

3. Use the site at Molinspiration, but use the SMILES INPUT option for the following molecule:

Acetaminophen

Do a Pharmacophore similarity search on the SMILES string and see what you get. Print out the first page of your results. [If your SMILES search does not work, input the structure, do the pharmacophore similarity search, and get a printout of that page.]