CCL:G: chemoinformatics / a nomenclature challenge

 Sent to CCL by: Michel Petitjean [petitjean.chiral%gmail.com]
 Hello Tobias,
 I accessed to http://sci.tech-archive.net/Archive/sci.chem/2006-06/msg00154.html
 this Sunday morning.
 The name on this web page is the one we reported on the paper:
 (3S,5S,6S,7S,9S,10S,11S,13S,14S,15S,17S,19S,21S,22S,23S,25S,2R,18R,26R,27R)
 tetradecacyclo[13.11.1.0<1,18>.0<2,7>.0<2,11>.0<3,14>.0<5,27>.0<6,25>.0<9,26>.0<10,19>.0<13,18>.0<17,22>.0<21,26>.0<23,27>]heptacosane
 The atom numbering is different from the one in my web page. Normally,
 numbering the atoms should be part of the naming algorithm.
 The R/S assignments are not the expected ones : twelve carbons should
 be flagged S, not more, according to CIP rules (can be checked
 manually).
 I also acessed this Sunday morning to
 http://darkhammer.multiply.com/journal/item/223
 The name on this web page does not contain stereo information
 (superscripting is not reproduced, can be viewed on the original web
 page):
 tetradecacyclo[13.11.1.01,18.02,7.02,11.03,14.05,27.06,25.09,26.010,19.013,18.017,22.021,26.023,27]heptacosane.
 Regarding the InChI, it is mentioned on the InChI website that stereo
 is not supported: so, I cannot emit any criticism here.
 About the importance of posting about chiralane on the CCL:
 I do not claim that it is more important than questions about some
 parameter setting in Autodock or Gaussian or else usual question on
 the CCL.
 I just claim that it may launch a debate about stereochemistry, CIP
 rules and nomenclature, that some chemoinformaticians may like (and
 why not some non chemoinformaticians, too). And there are indeed
 chemoinformaticians reading the CCL.
 No care about the fact that this molecule is not yet synthesized.
 Among the roughly 50 millions of CAS structures, there are a huge of
 virtual ones, many of them being much more sophisticated than
 [6.6]Chiralane, which is just a C27 alkane: only C,H, and single
 bonds.
 And yes the [6.6]chiralane was designed by Uncle Al.
 His name and contribution are clearly acknowledged on my web page.
 Furthermore, he gave me his permission to post the challenge in CCL.
 The data on my web page are public because they are published on a
 journal article (Al and me are coauthors).
 It has been edited by an experienced Romanian chemoinformatician and
 anonymously peer reviewed.
 So, there is no doubt that I never intended to put the credit of the
 chiralane on me only.
 I should get after two weeks the permission from Symmetrion (the
 Publisher of the paper) to post the pdf on my web page.
 Before that, I can email private copies upon request.
 Thank you very much for having replied.
 Best regards,
 Michel.
 Michel Petitjean,
 CEA/DSV/iBiTec-S/SB2SM (CNRS URA 2096),
 91191 Gif-sur-Yvette Cedex, France.
 Phone: +331 6908 4006 / Fax: +331 6908 4007
 E-mail: michel.petitjean]-[cea.fr, petitjean.chiral]-[gmail.com (preferred)
 http://petitjeanmichel.free.fr/itoweb.petitjean.graphs.html
 ---------- Forwarded message ----------
 > From: Tobias Kind tkind/aucdavis.edu <owner-chemistry]-[ccl.net>
 Date: 2009/11/21
 Subject: CCL: chemoinformatics / a nomenclature challenge
 To: "Petitjean, Michel " <petitjean.chiral]-[gmail.com>
 Sent to CCL by: "Tobias Kind" [tkind]|[ucdavis.edu]
 Hello Michel,
 actually the name was already posted back in 2006 and 2009.
 1) sci.tech-archive.net/Archive/sci.chem/2006-06/msg00154.html
 2) darkhammer.multiply.com/journal/item/223
 Marvin from ChemAxon can import and export the correct name.
 Hence it can create the name from the connection table, and it can create
 the molecule connection table from the name. I don't know if the IUPAC Name
 is correct (I guess so, maybe Daniel the author can help) but at least its
 consistent within the algorithm. Regarding the generation of all
 stereoisomers and the correct naming of those molecules, that is a
 different case I would say and unless somebody cooks that molecule also of
 lesser importance than lets say the pig flu.
 Run Marvin free with JAVA (Naming is licensed):
 http://www.chemaxon.com/marvin/examples/webstart/mview.jnlp
 [6.6]chiralane
 tetradecacyclo[13.11.1.0^{1,18}.0^{2,7}.0^{2,11}.0^{3,14}.0^{5,27}.0^{6,25}.0^{9,26}.0^{10,19}.0^{13,18}.0^{17,22}.0^{21,26}.0^{23,27}]heptacosane
 [6.6]chiralane
 InChI=1S/C27H28/c1-7-19-9-2-15-21-13-5-12-20-8(1)23(9,13)27-24(7)10(20)3-16-22-14(24)4-11(19)25(15,27)18(22)6-17(21)26(12,16)27/h7-22H,1-6H2
 [6.6]chiralane InChIKey JKJBBXWDXQSMMM-OXSFYKJQBU
 http://petitjeanmichel.free.fr/itoweb.petitjean.graphs.html#CHIR
 If I wouldn't know better I would say that looks like a typical Uncle Al
 question, well it was :-)
 Cheers
 Tobias Kind
 http://fiehnlab.ucdavis.edu/
 > Sent to CCL by: Michel Petitjean [petitjean.chiral%x%gmail.com]
 > Dear CCLers,
 >
 > Here is my challenge: assign a name to the [6.6]chiralane, C27H28.
 > The connection table is available from
 > http://petitjeanmichel.free.fr/itoweb.petitjean.graphs.html#CHIR
 > If somebody has a programme running successfully on this small molecule,
 > please tell me and send me the name:
 > until now, nomenclature assignment programmes failed !
 > Furthermore, I would be delighted to know what name is
 > generated from CAS or IUPAC rules.
 > Many thanks.
 >
 > All my best,
 >
 > Michel Petitjean,
 > CEA/DSV/iBiTec-S/SB2SM (CNRS URA 2096),
 > 91191 Gif-sur-Yvette Cedex, France.
 > Phone: +331 6908 4006 / Fax: +331 6908 4007
 > E-mail: michel.petitjean,,cea.fr, petitjean.chiral,,gmail.com (preferred)
 > http://petitjeanmichel.free.fr/itoweb.petitjean.html
 >
 >
 Dr. Tobias Kind
 UC Davis Genome Center
 Metabolomics Group
 http://genomecenter.ucdavis.edu
 Tel:+1-530-752-9922http://www.ccl.net/cgi-bin/ccl/send_ccl_messagehttp-:-//www.ccl.net/chemistry/sub_unsub.shtmlhttp-:-//www.ccl.net/spammers.txt