Dealing with the complex challenge of managing diverse chemistry

data online

Antony Williams, Valery Tkachenko, Alexey Pshenichnov and Ken Karapetyan

ACS San Francisco

August 2014

CAS Counter http://www.cas.org/content/counter

About Me…as a Chemist• I’ve performed a few dozen chemical

syntheses• I’ve run thousands of analytical spectra• I’ve generated thousands of NMR assignments• I’ve probably published <5% of all work • Most of it has been lost• But things can be different today….• But it still needs to be associated with me…

• If we imagine that permission exists… (i.e. forget IP, chemical and pharma companies etc…think students…)– How many syntheses are performed– How many spectra are run– How many properties are measured– How many compounds are made– How many, how much, how big??.....– Let’s go manage it all!!

Think about chemistry a mo’

Consider a shift to Openness

Times have changed…

Open Access funder mandates…

Publishers are responding

The world of Open Data is here

Open Data are everywhere

• Is Openness and Social Sharing changing the world?

• The cultural experiments in Open Data and exchange are almost daily

• Mobile platforms enhance participation

• And then what of Chemistry Data???

An Experiment - ChemSpider

• ChemSpider allowed the community to participate in linking the internet of chemistry & crowdsourcing of data

• Successful experiment in terms of building a central hub for integrated web search

• More people are “users” than “contributors”

• Yet basic feedback and game-play helps

An Experiment - CSSP

An EPSRC Call

“…the identification of the need for a UK national service for the provision of a searchable, electronic chemical database for the UK academic research community.”

National Chemical Database Service

• Manage “all” of the chemistry data associated with chemical substances – PUBLISHED and UNPUBLISHED

• Based on user selected licensing the data to be downloadable, reusable, interactive

• Build a platform that enables the scientist • Data storage, validation, standardization and

curation• Collaborative data sharing

• Provide data platform that can enable and enhance publishing of scientific papers

We set a vision…

Data Repository

• Registration of chemical compounds

• Deposition of chemical syntheses

• Addition of analytical data

• Integration to electronic notebooks

• Rewards and recognition for data sharing

• Document processing

• Hosting of data as private, embargoed or public

Development of Data Repository

• Data repository should not just be a data dump – should not be a “big disk”

• Searchable, integrated, segregated repository of data types

• Data access including private, shared embargoed and public

• Delivery of derived models from data

New Repository Architecturedoi: 10.1007/s10822-014-9784-5

New Repository Architecture

Compounds Reactions Spectra Materials Documents

CompoundsAPI

ReactionsAPI

SpectraAPI

MaterialsAPI

DocumentsAPI

CompoundsWidgets

ReactionsWidgets

SpectraWidgets

MaterialsWidgets

DocumentsWidgets

Data tier

Data access tier

User interface

components tier

Analytical Laboratory application

User interface tier

(examples) Electronic Laboratory Notebook

Paid 3rd party integrations (various platforms – SharePoint, Google, etc)

Chemical Inventory application

Input data pipeline

Deposition Gateway

Staging databases

Compounds

Reactions

Spectra

Materials

Articles / CSSP

Compounds Module

Spectra Module

Reactions Module

Materials Module

TextminingModule

1Module

Web UI for unified depositions

DropBox, Google Drive, SkyDrive, etc

LabTrove and other templated data

Documents

API, FTP, etc

Raw data Validated dataStaging

databases

All databases are sliced by data sources/data

collections and have simple

security model where each data

slice/source is private, public or

embargoed

Compounds

Reactions

Analytical data

Crystallography data

For Deposition of Data• Quality of data at source

• ensuring chemicals are correct - VALIDATION• reactions map and balance as appropriate –

VALIDATION and STANDARDIZATION• file format handling for analytical data types –

binary file formats are proprietary - STANDARDIZATION

• valid interpretation of data – VALIDATION and ANNOTATION

Input data pipeline

Deposition Gateway

Staging databases

Compounds

Reactions

Spectra

Materials

Articles / CSSP

Compounds Module

Spectra Module

Reactions Module

Materials Module

TextminingModule

1Module

Web UI for unified depositions

DropBox, Google Drive, SkyDrive, etc

LabTrove and other templated data

Documents

API, FTP, etc

Raw data Validated dataStaging

databases

All databases are sliced by data sources/data

collections and have simple

security model where each data

slice/source is private, public or

embargoed

Depositions Gateway User Interface

Deposition of Data

Validate and Standardize

CVSP Filtering

CVSP Filtering of DrugBank

ChEMBL (1.3 million records)

• 11,020 records with 4 bonds and zero charge, e.g. CHEMBL501101 or CHEMBL501973

• 271 records with hypervalent oxygen (e.g. , CHEMBL2219679), carbon (e.g. 1005895), boron, chlorine, iodine or phosphine

• 6,177 records where direction of bond makes no sense, e.g. CHEMBL12760 and CHEMBL34704

Depositions User Interface

The challenges of analytical data

• Vendors produce complex proprietary data formats and standard formats are required (JCAMP, NetCDF, AniML)• ChemSpider already hosts thousands of JCAMP spectra

• Support of “assigned spectra” in place

• Data validation approaches understood

• There are a myriad of analytical data types…

ChemSpider ID 24528095 H1 NMR

ChemSpider ID 24528095 C13 NMR

ChemSpider ID 24528095 HHCOSY

ChemSpider ID 24528095 HSQC

ChemSpider ID 24528095 HMBC

Managing Assignments?

Depositions User Interface

Depositions from ELNs

• Development work integrating chemistry into the Southampton Labtrove notebook• Stoichiometry table development• Analytical data integration

• “ChemTrove” rolled out to a small test group in January

Document deposition/processing

Experimental data checker

User Interface Approach

Compounds Reactions Spectra Materials Documents

CompoundsAPI

ReactionsAPI

SpectraAPI

MaterialsAPI

DocumentsAPI

CompoundsWidgets

ReactionsWidgets

SpectraWidgets

MaterialsWidgets

DocumentsWidgets

Data tier

Data access tier

User interface

components tier

Analytical Laboratory application

User interface tier

(examples) Electronic Laboratory Notebook

Paid 3rd party integrations (various platforms – SharePoint, Google, etc)

Chemical Inventory application

User Interface Approach

Compounds Reactions Spectra Materials Documents

CompoundsAPI

ReactionsAPI

SpectraAPI

MaterialsAPI

DocumentsAPI

CompoundsWidgets

ReactionsWidgets

SpectraWidgets

MaterialsWidgets

DocumentsWidgets

Data tier

Data access tier

User interface

components tier

Analytical Laboratory application

User interface tier

(examples) Electronic Laboratory Notebook

Paid 3rd party integrations (various platforms – SharePoint, Google, etc)

Chemical Inventory application

Display Widgets

Work in Progress

Work in Progress

User Interface Approach

Compounds Reactions Spectra Materials Documents

CompoundsAPI

ReactionsAPI

SpectraAPI

MaterialsAPI

DocumentsAPI

CompoundsWidgets

ReactionsWidgets

SpectraWidgets

MaterialsWidgets

DocumentsWidgets

Data tier

Data access tier

User interface

components tier

Analytical Laboratory application

User interface tier

(examples) Electronic Laboratory Notebook

Paid 3rd party integrations (various platforms – SharePoint, Google, etc)

Chemical Inventory application

Analytical Chemist

Characterize

Measure

Search

Store

<<include>>

<<include>>

<<include>>

Synthetic Chemist

Search(synthetic procedure)

Document(publish synthetic procedure)

Retrosynthetic analysis

A Compounds Repository Interface

A Reactions/Document Interface

The PharmaSea Website

The Open PHACTS community ecosystem

Open Source Drug Discovery India

What can drive participation?

• What can drive scientists to participate and contribute?• Ensuring provenance of their data for reuse• Mandates from funding agencies• Improved systems to ease contribution• Additional contributions to science• Improved publishing processes• Recognition for contributions

Scientists are Increasingly Quantified…

AltMetrics as Scientist Impact

AltMetrics

Detailed Usage Statistics

Rewards and Recognition

Congratulations! Your 1st CSSP article has been published. Philosopher Lao Tzu said “A journey of a thousand miles begins with a single step”. In the same way we hope that this will be the first of many submissions that you make to CSSP.

The First Step badge is awarded when a user submits (& has published) their 1st CSSP article.

http://orcid.org/0000-0002-2668-4821

AltMetrics Feeds

• For our data repository ensure contribution of data will feed out to the AltMetrics platforms

• Every data point, every data download, use and reuse will be associated with the scientist

• Data will be DOI’ed (presently under review)

• Services provided will allow for AltMetrics use

What do we have in place?• We are testing an early form of the data

repository on our data – ChemSpider and our archive of publications

• Working with collaborators to define needs

• Testing and enhancing deposition systems

• Chemical validation & standardization platform

• Analytical data handling formats

• And lots in development…

The Challenges Ahead

• Chemistry is NOT just nicely defined structures!• Materials, minerals, attached to beads,

polymers, ambiguous materials

• Domain-specific measurements• File format standards are limited in application

• Encouraging scientists to free up their data• AltMetrics, open data mandates, systems

• The data explosion continues

But it’s not easy of course

• Not everything we would like around data handling is there for sure

• Many systems, tools, platforms are already available but we don’t know about them or even if we did contributing us “more work”

• “What’s in it for me?”, “It’s my data”, “It’s too much work”, “What credit do I get?”

And yes…we know…

Thank you

Email: williamsa@rsc.orgORCID: 0000-0002-2668-4821 Twitter: @ChemConnectorPersonal Blog: www.chemconnector.com SLIDES: www.slideshare.net/AntonyWilliams