Since its initial adoption of ChemAxon tools in 2009, GlaxoSmithKline has followed a roadmap moving from desktop tools to web-based enterprise solutions. This presentation will touch on previous milestones, provide an update on the current activities, and describe the alignment of GSK with the ChemAxon vision for the Plexus Discovery suite.

1. From Desktop to Browser
ChemAxon Plexus at GlaxoSmithKline
Brett Hiemenz GSK

2. Abstract
216 Sep 2014ChemAxon UGM Budapest
• GlaxoSmithKline began using ChemAxon tools across its
enterprise systems in late 2009. This presentation will outline
the increasing adoption and the trend from desktop to web
applications will be highlighted. Recent GSK activities in
Plexus components will be highlighted: Compound
Registration, Plexus Library Design, Instant JChem
Web/Plexus Connect.
• Desktop applications are still preferred for some analysis
activities, so a Spotfire visualization tool will be presented.

3. Agenda
1. Retrospectives on Plexus suite components
• IJC
• Compound Registration
2. Building web applications on core ChemAxon suites
• Enterprise Search enhanced with Chemistry
3. Building chemistry capabilities into remaining desktop tools
4. Alignment with Plexus roadmap – moving from desktop to web
5. Conclusions.
316 Sep 2014ChemAxon UGM Boston

4. Retrospective 1: Instant JChem Evolution
416 Sep 2014ChemAxon UGM Boston
• Initial replacement for ISISBase began 2009. Rollout 5.6 mid 2011.
– ChemAxon converted H-views to IJC projects like-for-like. 400 H-views approx half converted.
– Bespoke tools to create test-prod environments
– Slow US performance necessitated Citrix.
• Cross Pharma prioritisation of requirements. Uplift to 5.7.2.1 in 2012
• Evaluation of JChem Web Browser 2013
– GSK database architecture made performance slow.
– Joining across multiple data sources
• 2014 Uplift to version 6.2 using ChemAxon Services to replace test/prod
publication mechanism.
– Still using Citrix for US users (databases mostly in UK)

5. Retrospective 2: Small Molecule Registration
516 Sep 2014ChemAxon UGM Boston
• March 2011 collaboration with ChemAxon to create a new Registration ‘Service’
inside firewall to comply with GSK business rules using standard formats
– Delivered into production at GSK March 2012 (migrated 6 million records)
• Phase 2 collaboration with ChemAxon to deliver as part of ‘product’ mid 2013.
• Now Scientists can use a web app to ‘fix’ compounds that do not auto-register
– Target was 70% non-registrar assisted registrations. Actual is 84%
– 250+ chemists have registered compounds themselves
– Increase from 4% to 7% require some post-registration modification. Mostly handled through training
• Very few issues reported during rollout despite big process change
– Peptide conversions from eLNB CDX format does not maintain orientation and bond lengths correctly

6. Enterprise Search with Chemistry: Socrates Search
616 Sep 2014ChemAxon UGM Boston
• Using JChem Suite to add Chemistry to the GSK Enterprise Search engine
• Presented to BioIT world in 2013 (and won an innovation award)
• GSK data are crawled and the ‘chemistry’ extracted into an Oracle database with
a ChemAxon powered index
– Substructure search only
– Reaction search is possible but the business did not prioritize it
–Electronic Lab Notebook Reactions are included in the indexing.
– JChem libraries used for format conversions and image rendering

7. Not All Web: Continued Support for Desktop Analysis Tools
716 Sep 2014ChemAxon UGM Boston
• Chemistry representation in Spotfire. GSK Spotfire Structure Visualizer was not
compatible with Spotfire 6.0. necessitating a replacement
• ChemAxon Services have developed a JChem for Spotfire plug-in replacing all of
the capabilities of the GSK bespoke tool
• Key features:
– Structure renderer can replace SMILES with structures in table cells, plot labels, tooltips, and more
– Grid visualization of structures allows cherry-picking/marking, exporting, display of multiple SMILES
columns (e.g. R-groups)

8. ChemAxon Structure Visualizer for Spotfire
816 Sep 2014ChemAxon UGM Boston

9. What’s Next for Chemistry Desktop: Plexus
916 Sep 2014ChemAxon UGM Boston
• Working with ChemAxon to align with the Plexus roadmap and vision.
– Web-based tools allow for more rapid deployment, easier support, fewer desktop conflicts, and easier
migration to touch interfaces
– Web-based tools also address architectural and security problems with desktop data analysis
• Partnership with Schrödinger on LiveDesign
– LiveDesign integrates Marvin for Javascript.
– Plexus Library Design licensed for use in Markush enumeration. Development of reaction-based
enumeration is in progress.
• GSK/ChemAxon beginning collaboration on IJC Web/Plexus Connect
– Beginning October 2014 with an IJC gap analysis and addressing any key gaps
– Planning 2015 project to migrate from IJC desktop to Plexus Connect using ChemAxon Services

10. In Conclusion
1016 Sep 2014ChemAxon UGM Boston
• ChemAxon began as key vendor for GSK in 2009
• Collaborated on Registration starting in 2011
• Licensed Plexus Library Design in 2013
• Collaborating on Plexus Connect in 2014
• Planned implementation of Plexus Connect in 2015

11. Thank you for your attention
1116 Sep 2014ChemAxon UGM Boston
Questions?

12. UGM Presentations. IJC, JChem Cartridge and Web services
1216 Sep 2014ChemAxon UGM Boston
• SOA-at-GSK-Working-in-a-Mixed- Technology-Environment : Brett Hiemenz San Diego 2009
• Implementation of ChemAxon in an SOA environment : Shane Weaver : Budapest 2010
• SAR analysis in Excel using Helium and JChem Karen Worsfold – Budapest 2011
• Deploying Instant JChem on an Enterprise Scale: Brett Hiemenz - San Diego 2011
• Delivering Instant JChem to the Masses - A User Perspective : Stephen Swanson - Budapest
2012
• IJC in the wider enterprise – 18 months on : Karen Worsfold Budapest 2013

13. UGM Presentations: Compound Registration
1316 Sep 2014ChemAxon UGM Boston
• A-novel-Approach-to- Pharmaceutical-Registration :Charlie Wilkins San Diego 2011
• Going live with registration as a service : Richard Bolton/Akos Papp Budapest 2012
• Registration as a Service: the full story after half a year. Rama Bhamidipati/Akos Papp
Boston2012

14. Retrospective 2: Small Molecule registration Evolution Phase1
1416 Sep 2014ChemAxon UGM Boston
• CRISP targets registration simplification by conversion to ‘service’. GSK legal
raise concerns about hosting registration outside firewall.
• March 2011 collaboration with ChemAxon to create a new Registration ‘Service’
inside firewall to comply with GSK business rules using standard formats.
• Delivered into production at GSK March 2012 (migrated 6 million records)
• Phase 1 ChemAxon registration approx 48% automated registration. 2013
approx 48k NCE registered of these approx 21k achiral/no stereo

15. Compound Name
CCE 001
CCE 002
CCE 003
Purchased
Compounds
The purchasing chemist sends the SD File to
Registrars and they are registered as new
entities
optionally, request
assistance from the
registrar
Contract
Chemist
Chemist
Purchasing
Chemist
eLNB or
WebReg
Fully Specified compounds
Registrar
Tools
Registry
Chemist or contract coordinator
enter compounds to be registered
and is notified of undefined
attributes
Compounds that are fully
describe in regard to
stereochemistry, racemic
content are automatically
registered
Compounds with undefined
attributes are sent to a staging
area for registrar attention
Chemists purchase compound
sets and receive data files with
structure information
Registrars modify compounds
for consistency, confirm with the
chemist then register
Registrar
Business Rules
SD Files
Phase I - Laying the Groundwork
Staging
Business Rules
defined by
Standardizer and
Structure Checker
Configurations
Charlie Wilkins San Diego UGM Sept 2011

16. Other?
Compound Name
CCE 001
CCE 002
CCE 003
Purchased
Compounds
Compound Collection Enhancement send the SD
File to Registry as received and registered as
new entities
optionally, request
assistance from the
registrar
Phase II – Optimization
Contract
Chemist
Chemist
CCE
Chemist
eLNB or
WebReg
Fully Specified compounds
Registry
Tools
Compound Collection
Enhancement purchase
compounds and receive data
files with structure information
Registrar
SD FilesSD Files
Fully Specified compounds Business Rules
Staging
Compounds that are fully
describe in regard to
stereochemistry, geometric
isomerism content are
automatically registered
Compounds with undefined
attributes are sent back to
chemists
Registrars or chemists modify
compounds for consistency,
confirm with the chemist then
register
Registry
x
x
x
Charlie Wilkins San Diego UGM Sept 2011

17. Search Technology Overview
17
Autonomy
(Text Entities)
ChemAxon
(Chemical Structures)
Socrates Search
Lab Notebook
HazELNut
LeadMine
(Text Analytics)
Documentum Lotus
BioIT world 2013

18. Text Analytics
18
Universally Unique
Tag
Text
Chemical
Fingerprint
Structure
Document
Annotations
Substructure Search
Exact structure search
Aspirin
2-acetoxybenzoic acid (IUPAC)
O=C(Oc1ccccc1C(=O)O)C (SMILES)
CCI133 (GSK ID)
2-acetyloxybenzoic acid
acetylsalicylate
acetylsalicylic acid
O-acetylsalicylic acid
Embedded OLE objects (ChemDraw, ISIS Draw)
Tag
Tag
Gene
Disease
AJSHBSYTW6HSG8KJG9KA
BioIT world 2013