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Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
Improving online chemistry one structure at a time
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Improving online chemistry one structure at a time

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RSC|ChemSpider is one of the world’s largest online resources for chemistry related data and services. Developed with the intention of delivering access to structure-based chemistry data via the …

RSC|ChemSpider is one of the world’s largest online resources for chemistry related data and services. Developed with the intention of delivering access to structure-based chemistry data via the internet the ChemSpider platform hosts over 26 million unique chemical compounds aggregated from over 400 data sources and provides an environment for the community to both annotate and curate these existing data as well as deposit new data to the system. The search system delivers flexible querying capabilities together with links to external sites for publication and patent data. ChemSpider has spawned a number of projects include ChemSpider SyntheticPages for hosting openly peer-reviewed chemical synthesis articles. This presentation will review the present capabilities of the ChemSpider system providing direct examples of how to use the system to source high quality data of value to pharmaceutical companies. We will discuss some of the challenges associated with validating data quality, examine how ChemSpider is a part of the semantic web for chemistry and investigate approaches to using ChemSpider integrated to analytical instrumentation.

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  • 1. Improving Online Chemistry – One Structure at a Time Antony Williams AstraZeneca, February 10 th 2012
  • 2. We Have …Too Much Data!!!
  • 3. It is so difficult to navigate… What’s the structure? Are they in our file? What’s similar? What’s the target? Pharmacology data? Known Pathways? Working On Now? Connections to disease? Expressed in right cell type? Competitors? IP?
  • 4. Pharma Information..and the web… Literature Patents News Pipeline SAR CSRs Safety In vivo Etc
  • 5. The World of Online Chemistry
    • Property databases
    • Compound aggregators
    • Screening assay results
    • Scientific publications
    • Encyclopedic articles (Wikipedia)
    • Metabolic pathway databases
    • ADME/Tox data – eTOX for example
    • Blogs/Wikis and Open Notebook Science
    • Contributing Open Source code to projects
  • 6. PubChem
  • 7. ChEMBL
  • 8. Collaborative Knowledge Management
  • 9. e-Science and Primary Data
    • How much data generated in a lab, that COULD go public, is lost forever?
  • 10. e-Science and Primary Data
    • How much data generated in a lab, that COULD go public, is lost forever?
    • Public Domain reference databases of value?
      • Syntheses
      • Properties
      • Spectra
      • CIFs
      • Images
  • 11. e-Science and Primary Data
    • How much data generated in a lab, that COULD go public, is lost forever?
    • Public Domain reference databases of value?
      • Syntheses
      • Properties
      • Spectra
      • CIFs
      • Images
    • Much of chemistry is chemical structure-based – where and how could we host these data?
  • 12. RSC’s ChemSpider
  • 13. We Want to Answer Questions
    • Questions a chemist might ask…
      • What is the melting point of n-heptanol?
      • What is the chemical structure of Xanax?
      • Chemically, what is phenolphthalein?
      • What are the stereocenters of cholesterol?
      • Where can I find publications about xylene?
      • What are the different trade names for Ketoconazole?
      • What is the NMR spectrum of Aspirin?
      • What are the safety handling issues for Thymol Blue?
  • 14. Available Information…
    • Linked to vendors, safety data, toxicity, metabolism
  • 15. Available Information….
  • 16. Crowdsourced “Annotations”
    • Users can add
      • Descriptions/Syntheses/Commentaries
      • Links to PubMed articles
      • Links to articles via DOIs
      • Add spectral data
      • Add Crystallographic Information Files
      • Add photos
      • Add MP3 files
      • Add Videos
  • 17.  
  • 18. Spectra
  • 19. Data on the Web
  • 20.  
  • 21. Chemistry Data online is messy
    • We have inherited errors
    • All public compound databases, including ours, have errors
    • “ Incorrect” structures – assertions, timelines etc
    • “ Incorrect” names associated with structures
    • Properties
    • Links
    • Publications
    • ENORMOUS CHALLENGE
  • 22. What could create change?
    • Harvard Business Review (2010)
    • “ One change would make a substantial difference [ to drug R&D ] : the creation of agreed-upon standards for digitally representing drug assets. ”
    • Consider drug structures ONLY…
  • 23. The Structure of Vitamin K?
  • 24. MeSH
    • A lipid cofactor that is required for normal blood clotting. Several forms of vitamin K have been identified: VITAMIN K 1 (phytomenadione) derived from plants , VITAMIN K 2 (menaquinone) from bacteria, and synthetic naphthoquinone provitamins, VITAMIN K 3 (menadione). Vitamin K 3 provitamins, after being alkylated in vivo, exhibit the antifibrinolytic activity of vitamin K. Green leafy vegetables, liver, cheese, butter, and egg yolk are good sources of vitamin K
  • 25. The Structure of Vitamin K1?
  • 26. What is the Structure of Vitamin K1?
  • 27. CAS’s Common Chemistry
  • 28. Wikipedia
  • 29.  
  • 30.  
  • 31. ChEBI – Manual Curation
  • 32.  
  • 33.  
  • 34.  
  • 35.
    • “ 2-methyl-3-(3,7,11,15-tetramethyl hexadec-2-enyl)naphthalene-1,4-dione”
    • Variants of systematic names on PubChem
    • 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethyl
    • 2-methyl-3-[(E,7S,11R)-3,7,11,15-tetramethyl
    • 2-methyl-3-[(E,7R,11S)-3,7,11,15-tetramethyl
    • 2-methyl-3-[(E,7S,11S)-3,7,11,15-tetramethyl
    • 2-methyl-3-[(E,11S)-3,7,11,15-tetramethyl
    • 2-methyl-3-[(E)-3,7,11,15-tetramethyl
    • 2-methyl-3-(3,7,11,15-tetramethyl
    • 2-methyl-3-[(E)-3,7,11,15-tetramethyl
  • 36. What’s Methane?
  • 37. What’s Methane?
  • 38. What ELSE is Methane???
  • 39.  
  • 40. EPA’s DailyMed
  • 41. EPA’s DailyMed
  • 42. EPA’s DailyMed
  • 43. With Great Fanfare…
  • 44. NPC Browser http://tripod.nih.gov/npc/
  • 45. NPC Browser http://tripod.nih.gov/npc/
  • 46.  
  • 47. Openness and Quality Issues Williams and Ekins, DDT, 16: 747-750 (2011) Science Translational Medicine 2011
  • 48. Content is King and Quality Costs
    • Curated Chemistry “content” is expensive to create
      • Patent searching
      • Structures and properties
      • Drug databases
      • Literature databases
    • Chemical Abstracts Service (CAS), the “Gold Standard” in Chemistry related information
      • 104 years of content
      • >50 million substances
      • Proprietary platform
  • 49. The EXPERTS must get it right?!
  • 50. Wikipedia, C&E News, PubChem
    • C&E News (from ACS)
  • 51. Feedback from Steve Ritter
    • “ Although CAS and C&EN are both part of the ACS Publications Division, we at C&EN still have to pay for our SciFinder access, strangely enough.”
    • “ It would be nice to have an authoritative web-based source of standard, well-drawn structures for chemists to go to so they can freely cut and paste structures into their papers, PowerPoint presentations, and anything else they might need. Maybe Wikipedia will be that source one day .”
  • 52. Public Domain Databases
    • Our databases are a mess…
    • Non-curated databases are proliferating errors
    • We source and deposit data between databases
    • Original sources of errors hard to determine
    • Curation is time-consuming and challenging
  • 53. Stop Whining – Fix it
  • 54. Crowdsourced Curation
    • Crowd-sourced curation: identify/tag errors, edit names, synonyms, identify records to deprecate
  • 55. Search “Vitamin H”
  • 56. “ Curate” Identifiers
  • 57. “ Curate” Identifiers
  • 58. “ Curate” Identifiers
  • 59. Standards : Structure Standardization
  • 60. Standards : Structure Standardization
  • 61. Standards : Structure Standardization
  • 62. What needs to happen?
    • Standards
      • Standardization of structures
        • ChEBI/PubChem sharing
        • InChI adoption
  • 63. The InChI Identifier
  • 64. Multiple Layers
  • 65. InChIStrings Hash to InChIKeys
  • 66. Vancomycin – Search the Internet
  • 67. Vancomycin Search Molecular SKELETON Search Full Molecule
  • 68. Full Skeleton Search: 104 Hits
  • 69. Full Molecule Search: 4 Hits
  • 70. Crowdsourcing Works
    • >130 people have deposited data and participated in data curation
    • Different level curators check each other
    • More curators and depositors are encouraged!
  • 71. What needs to happen?
    • Standards
      • Standardization of structures
        • ChEBI/PubChem sharing
        • InChI adoption
    • Collaboration
      • Stop reinventing the wheel
      • Share data, share efforts and speed the process
  • 72. Antony Williams vs Identifiers Passport ID Dad, Tony, others SSN Green Card License 5 email addresses ChemSpiderman (blog, Twitter account, Facebook, Friendfeed) OpenID … .
  • 73. Aspirin names and synonyms
    • Text searches depend on correct association
    • 335 suggested identifiers for Aspirin just on PubChem!
    • Disambiguation dictionaries are necessary, not just for authors!
  • 74.  
  • 75. The Final Search Strategy
  • 76. All Those Names, One Structure
  • 77. Curated Dictionaries Matter
  • 78. Success Depends on Dictionaries
  • 79. Validated Name-Structure Dictionaries
    • Chemical name dictionaries are used for:
        • Text-mining (publications, patents)
          • Used to index PubMed and link to Google Patents
        • Linking to other databases – think Biology!
          • When structures are not available drug names link
        • Searching the web
          • Names link to structures link to InChIs
  • 80. I want to know about “Vincristine” If all algorithms work then everything on the page is correct by default except the name-structure relationship!
  • 81. Vincristine: Identifiers and Properties
  • 82. Vincristine: Patents Linked by Name
  • 83. Vincristine: Articles Linked by Name
  • 84. ChemSpider Everywhere: What do computers want?
    • Web services
  • 85. Mass Spec Analysis
  • 86. ChemSpider Interface
  • 87.  
  • 88. Tinuvin 328
  • 89. Position sorted by references
  • 90. Position 1 only
  • 91. Web Services
  • 92. Web Services Open Up Collaboration
    • Agilent, Bruker, Waters and Thermo all use our web-based services for compound lookup
    • Many academic sites integrating directly – metabonomics, name lookup, semantic markup
    • Mobile app integration
    • Commercial structure drawing packages
  • 93. ChemSpider Everywhere : Embed
  • 94. ChemSpider Everywhere: Spectral Game
  • 95. ChemSpider Everywhere Crowdsourced Curation of Spectra
  • 96. ChemSpider Everywhere : ChemMobi
  • 97. Structure Database Lookup
  • 98. ChemSpider Resources for Chemistry
  • 99. It is so difficult to navigate… What’s the structure? Are they in our file? What’s similar? What’s the target? Pharmacology data? Known Pathways? Working On Now? Connections to disease? Expressed in right cell type? Competitors? IP?
  • 100.
    • Open PHACTS Project
    • Develop a set of robust standards…
    • Implement the standards in a semantic integration hub
    • Deliver services to support drug discovery programs in pharma and public domain
    • 22 partners, 8 pharmaceutical companies, 3 biotechs
    • 36 months project
    Guiding principle is open access, open usage, open source - Key to standards adoption -
  • 101.  
  • 102. The Future Commercial Software Pre-competitive Data Open Science Open Data Publishers Educators Open Databases Chemical Vendors Small organic molecules Undefined materials Organometallics Nanomaterials Polymers Minerals Particle bound Links to Biologicals Internet Data
  • 103. The Future of Chemistry on the Web?
    • Public compound databases federate & build a linked environment of validated data!
    • Data validation needs are not ignored
    • Publishers layer on information to make publications discoverable
    • Public-Private databases can be linked
    • Open Data proliferate
    • The “ Semantic Web ” in action
  • 104. Acknowledgments
    • The ChemSpider team
    • Our data providers, depositors, collaborators and curators
    • Software providers – OpenEye, ChemDoodle, ACD/Labs, GGA Software, Open Source (Jmol, JSpecView, OpenBabel)
  • 105. Thank you Email: williamsa@rsc.org Twitter: ChemConnector Blog: www.chemspider.com/blog Personal Blog: www.chemconnector.com SLIDES: www.slideshare.net/AntonyWilliams

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