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#752 wrong aromaticity?

2.3.x
open
nobody
Library Functions (223)
5
2012-10-23
2011-09-21
Martin Gütlein
No

$obabel -:"CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2" -s"[#7]:[#6]:[#7]" -ocan
CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
1 molecule converted

this should not match according to daylight, the middle ring is not aromatic
http://www.daylight.com/daycgi/depict?434e3143434e28434331294343283d4f296e31633263636363633263283d4f295b6e485d633263316e63636332

Cheers,
Martin

Discussion

  • Noel O'Boyle

    Noel O'Boyle - 2011-09-21

    Where did the SMILES string come from?

     

  • Martin Gütlein

    Martin Gütlein - 2011-09-21

    the structure came from here: http://pubs.acs.org/doi/suppl/10.1021/ci049884m

    the acutal simles was created with cdk

     

  • Martin Gütlein

    Martin Gütlein - 2011-09-21

    this was the smiles that came from cdk (the one I added above was already the -ocan output of openbabel).
    makes no difference, though

    [H]C1=NC3=C(C([H])=C1([H]))N([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2N3C(=O)C([H])([H])N4C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])C4([H])([H])