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Towards a Universal SMILES representation - A standard method to generate canonical SMILES based on the InChI.

ABSTRACT: UNLABELLED: BACKGROUND:There are two line notations of chemical structures that have established themselves in the field: the SMILES string and the InChI string. The InChI aims to provide a unique, or canonical, identifier for chemical structures, while SMILES strings are widely used for storage and interchange of chemical structures, but no standard exists to generate a canonical SMILES string. RESULTS:I describe how to use the InChI canonicalisation to derive a canonical SMILES string in a straightforward way, either incorporating the InChI normalisations (Inchified SMILES) or not (Universal SMILES). This is the first description of a method to generate canonical SMILES that takes stereochemistry into account. When tested on the 1.1 m compounds in the ChEMBL database, and a 1 m compound subset of the PubChem Substance database, no canonicalisation failures were found with Inchified SMILES. Using Universal SMILES, 99.79% of the ChEMBL database was canonicalised successfully and 99.77% of the PubChem subset. CONCLUSIONS:The InChI canonicalisation algorithm can successfully be used as the basis for a common standard for canonical SMILES. While challenges remain - such as the development of a standard aromatic model for SMILES - the ability to create the same SMILES using different toolkits will mean that for the first time it will be possible to easily compare the chemical models used by different toolkits.

SUBMITTER: O'Boyle NM

PROVIDER: S-EPMC3495655 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Towards a Universal SMILES representation - A standard method to generate canonical SMILES based on the InChI.

O'Boyle Noel M NM

Journal of cheminformatics 20120918 1

<h4>Unlabelled</h4><h4>Background</h4>There are two line notations of chemical structures that have established themselves in the field: the SMILES string and the InChI string. The InChI aims to provide a unique, or canonical, identifier for chemical structures, while SMILES strings are widely used for storage and interchange of chemical structures, but no standard exists to generate a canonical SMILES string.<h4>Results</h4>I describe how to use the InChI canonicalisation to derive a canonical ...[more]

PMID: 22989151

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Project description:BACKGROUND: There is great concern within health surveillance, on how to grapple with environmental degradation, rapid urbanization, population mobility and growth. The Internet has emerged as an efficient way to share health information, enabling users to access and understand data at their fingertips. Increasingly complex problems in the health field require increasingly sophisticated computer software, distributed computing power, and standardized data sharing. To address this need, Web-based mapping is now emerging as an important tool to enable health practitioners, policy makers, and the public to understand spatial health risks, population health trends and vulnerabilities. Today several web-based health applications generate dynamic maps; however, for people to fully interpret the maps they need data source description and the method used in the data analysis or statistical modeling. For the representation of health information through Web-mapping applications, there still lacks a standard format to accommodate all fixed (such as location) and variable (such as age, gender, health outcome, etc) indicators in the representation of health information. Furthermore, net-centric computing has not been adequately applied to support flexible health data processing and mapping online. RESULTS: The authors of this study designed a HEalth Representation XML (HERXML) schema that consists of the semantic (e.g., health activity description, the data sources description, the statistical methodology used for analysis), geometric, and cartographical representations of health data. A case study has been carried on the development of web application and services within the Canadian Geospatial Data Infrastructure (CGDI) framework for community health programs of the New Brunswick Lung Association. This study facilitated the online processing, mapping and sharing of health information, with the use of HERXML and Open Geospatial Consortium (OGC) services. It brought a new solution in better health data representation and initial exploration of the Web-based processing of health information. CONCLUSION: The designed HERXML has been proven to be an appropriate solution in supporting the Web representation of health information. It can be used by health practitioners, policy makers, and the public in disease etiology, health planning, health resource management, health promotion and health education. The utilization of Web-based processing services in this study provides a flexible way for users to select and use certain processing functions for health data processing and mapping via the Web. This research provides easy access to geospatial and health data in understanding the trends of diseases, and promotes the growth and enrichment of the CGDI in the public health sector.

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Dataset Information

Towards a Universal SMILES representation - A standard method to generate canonical SMILES based on the InChI.

Publications

Towards a Universal SMILES representation - A standard method to generate canonical SMILES based on the InChI.

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