Drawing accurate representations of chemical structures is difficult. Copying them from publications can be fraught with errors and it is common to see that structures in publications are incomplete in their definitions of stereochemistry and that groups are missing anyway. Such is the nature of the beast. I have blogged recently about an observation of a structure drawing error in C&E News and the editor was kind enough to comment. Here’s an image of a structure from a C&E News article about Micrococcin P1 from this weeks magazine. Check out the structure….can you see any issues?

micrococcin-p1_cenews Now that ChemSpider is part of the RSC we will be able to offer some of our experiences in identifying potential errors in structures before they are published. There are ways to do this so that both authors and editors alike get flagged to such issues. This is way down the road from migrating ChemSpider to RSC servers but would definitely bring value to helping to ensure quality of data in Chemistry.

Feel free to post your comments regarding any issues you see with the structure as drawn.

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8 Responses to “Micrococcin P1 and C&E News Structures”

  1. Arvin says:

    Hello Tony,

    I compared the structure to what we offer in ACD/Dictionary and the difference lies in the point of attachment of the CH=C-NH-CO-thaizole group within the large ring. I’m left wondering which is the correct structure.

  2. Stu says:

    Hmm, one of those thiazole rings looks a bit dodgy… one too many bonds to a sulfur and one too few to a nitrogen…

  3. Antony Williams says:

    Arvin – the structure in the ACD/Dictionary is WRONG. For two reasons. 1) It has NO stereochemistry and 2) The article is about the revised elucidation so your structure is an old one.

  4. Antony Williams says:

    Stu…bang on sir! Good eyes! C&E News got the new structure for Micrococcin P1 wrong. This stuff is NOT easy. In this case an basic chemical structure drawing program would have shown a positive charge on the sulfur in the ring and it should have immediately drawn attention to the issue. This one should not have been missed.

  5. Arvin says:

    Tony – It appears that ChemSpider also reports the incorrect structure for Micrococcin P1. It might be worth to check that out too. http://www.chemspider.com/Chemical-Structure.13635849.html

  6. ChemSpider Blog » Blog Archive » Micrococcin P1 Part 2 and the Advantages of Online Publishing says:

    [...] Micrococcin P1 and C&E News Structures 22 05 [...]

  7. Antony Williams says:

    Arvin, The new structure has been added to ChemSPider. The original one has been left on line with the annotation.

  8. AErin says:

    Tony, looks like the story is not finished yet :)

    Compare given here picture with new ChemSpider structure
    http://www.chemspider.com/Chemical-Structure.21486198.html

    Two differences can be found:
    1. Missed –CO-NH- fragment
    2. Opposite top double bond stereo – =CH-CH3 must be Z, not E

    But looking at the published in the paper structure I will not be so surprised if we find another reason to change stereoconfiguration(s) or constitution. Just personal feeling.

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