Wednesday, February 27, 2008

Proton Prediction

A nice article on proton prediction can be found in the latest issue of Spectroscopy Europe

A few more links summarizing where this new development has been already integrated, can be found on

Saturday, February 9, 2008

InChIKey Resolver

Tony Williams ('Chemspiderman') posted an interesting article on his weblog at

dealing with the 'translation' of an InChIKey back to a structural diagram via a 'lookup-service'.

I like Tony's idea of an Inchikey-resolver and I would like to support it. The only questions/remarks I have, deals with the efficiency of such a process in our world of 'parallel systems'.

A few facts first:

At the moment approx. 33 millions of organics are known. Chemspider holds approx. 21M, PUBCHEM-Compounds approx. 18M structures, which represents 2/3 of known chemistry. I know that within CHEMSPIDER structure correction is an ongoing process as it is e.g. within my own CSEARCH-project. NMRshiftdb has been severly improved over the last months, etc.

Now all these systems exchange structures ..... 'A' gets 10,000 structures from 'B', 'A' does some corrections and gives its structures to 'C'. 'B' doesnt know A's corrections and gives also its structures to 'C'. Now 'C' has 2 "versions" of the same structure - in principle you can ignore that for an Inchikey-resolver, but the situation is much more complicated, because CHEMSPIDER, PUBCHEM, etc. have dozens of contributors.

I have definitely understanding of data-curation and I know that data-curation is sometimes a work like 'Sherlock Holmes' has done, because experimental parts of publications (and especially NMR-assignments) tends to be cryptic. We have a lot of systems in parallel, everybody doing his/her job seriously, spends a lot of time on data-curation. What we need is not 10, 20, maybe 100 structure repositories - each of it is incomplete (see above). What we really need is ONE SINGLE STRUCTURE REPOSITORY ( we live on only ONE PLANET ! ) - now I also put my kevlar vest on and put 300 feet landmines around my house - we have it, its CAS ! Sorry to say so, but this is the most complete one. When you are interested in a specific structure and you dont find it in Chemspider, emolecules, Pubchem, etc. - what does this answer tell you. It simply tells you, it is not stored - it DOES NOT TELL you, that IT DOES NOT EXIST ! I am quite sure I will be (hopefully only virtually) beaten by the community for this statement, but please keep in mind the relationship between 'new things' (algorithm, data, new procedures, etc.) and 'data-curation' when hosting a large database. The 'curation-effort' doesnt linearly increase with the size of the database - its at least a quadratic relationship.

What we need is ONE, CENTRALIZED place for structures and 'retrieval functionality' (including this inchikey-resolver), which covers the COMPLETE KNOWN CHEMISTRY and NOT hundreds of incomplete and severly overlapping installations. Let me know, when I can put off my kevlar vest ;-))

An example in order to convince that this (highly desirable) curation-process leads to a lot of confusion:

Globostellatic acid F: was drawn with C-O-O-H (hydroperoxide) instead of a carboxyl group in NMRSHIFTDB -> the data went to PUBCHEM ( CID: 15938977 / original NMRSHIFTDB-number was 22047)

Within NMRShiftDB this entry has been corrected: NMRSHIFTDB-number 20093989 and went again to PUBCHEM: CID=11526176

Do a search on PUBCHEM for the name 'globostellatic' - you end up with 2 'globostellatic acid F' structures, one is correct, the other is a hydroperoxide instead of an acid. Its simply applied error-propagation ...... like in school, when you put your eyes into your neighbors work. When you copy it perfectly, you are consistent, but your examination might also be completely wrong, when your neighbor failes. In chemistry we have a more technical term - its called 'citation'.

Tuesday, February 5, 2008

Spectral Searching on PUBCHEM-Structures

About 2 years ago, a spectral search system based on 16M PUBCHEM structures (approx. 5M unique) has been built and made available on . It went online during May 2006.

Some background information:
  • C-NMR spectra have been calculated using CSEARCH-NN-technology
  • Spectral search technique is based on SAHO as implemented into CSEARCH
  • The main intention of this system is to get some feeling about the compound class for an unknown. It must be clearly stated, that a database of 5M unqiue structures is definitely too small to cover known organic chemistry (approx. 33M at 02/2007). When taking into account the possible structures for a given molecular formula, 5M structures represent a neglictable part of possible organic chemistry !

In the meantime there were massive updates on PUBCHEM - this was the reason for rerunning the predictions and implementing another (much faster) search technique - the principle is still based on Wolfgang Bremsers SAHO-technique - the speed has been increased to allow searching of 1 billion (10**9) of CNMR-spectra within less than 3 seconds on a single CPU. At the moment the system is only partly installed and allows searching of 405,704,611 spectral patterns (usually in 1.2-1.6 seconds).

Key features:

  • PREDICTED CNMR-spectra for approx. 23M unique structures downloaded from PUBCHEM using CSEARCH-NN-technology
  • Structures deposited from CHEMSPIDER are already included
  • Intention is again to give some flavour of possible compound classes for an unknown

A detailed description of the search-technique will be given soon - stay tuned !

Another nice feature of this system: Whenever an experimental set of NMR-data is available within CSEARCH / SPECINFO / NMRPRedict / NMRShiftDB / CHEMGATE - this information is automatically included into the final resulting table of structures !

Feel free to test it ! The URL is

Your feedback is highly appreciated - use the comment section !