Note: the most recent version of this tutorial can be found here and a short overview slide show here.
ChemmineOB provides an R interface to a subset of cheminformatics functionalities implemented by the OpelBabel C++ project [@18328109; @21982300]. OpenBabel is an open source cheminformatics toolbox that includes utilities for structure format interconversions, descriptor calculations, compound similarity searching and more.
ChemineOB aims to make a subset of these utilities available from within R. For non-developers,
ChemineOB is primarily intended to be used from
ChemmineR (Cao et al. 2008; Backman, Cao, and Girke 2011; Wang et al. 2013) as an add-on package rather than used directly.
To use the
ChemmineOB package on Linux or Mac, OpenBabel 2.3.0 or greater needs to be installed on a system. On Linux systems, the OpenBabel header files are also required in order to compile
ChemmineOB. The windows distribution will include its own version of OpenBabel. The OpenBabel site (http://openbabel.org/wiki/Get_Open_Babel) provides excellent instructions for installing the OpenBabel software on Mac or Linux systems. The
ChemmineOB packages can be installed from within R with the
biocLite install script.
source("http://bioconductor.org/biocLite.R") biocLite(c("ChemmineR", "ChemmineOB")) library("ChemmineR") library("ChemmineOB")
If the installation fails on Linux, you may need to manually set the locations of the open babel libraries and header files. This is best done through configure flags. For example, at the command prompt do:
$ R CMD INSTALL --configure-args='--with-openbabel-include=... --with-openbabel-lib=...' <ChemmineOB package file>
where the ‘…’ are replaced by the relevant paths. See the README file for more details.
Detailed instructions for using
ChemmineOB are provided in the vignette of the
ChemmineR package instead of this document. The main reason for consolidating the documentation in one central document rather than distributing it across several vignettes is that it helps minimizing duplications and inconsistencies. It also is the more suitable format for providing a task-oriented description of functionalities for users. To obtain an overview of the OpenBabel utilities supported by
ChemmineOB, we recommend consulting the OpenBabel Functions section of the
ChemmineR vignette. To open the
ChemmineR vignette from R, one can use the following command.
ChemmineOB now includes wrapper functions for all of OpenBabel, as genereted by SWIG. We still maintain our own set of functions to provide better integration with R in general and
If you are familiar with the Open Babel API, using the SWIG wrapper should be similar, once you know a few conventions used. You can look at the R code in this package to see examples of these.
OBConversion *x = new OBConversion(...)
in R you would have:
x = OBConversion(...)
stringpfunction. The char* pointer can be accessed with the
castslot. The value can be retrieved from the
valueslot. For example:
result = stringp() OBDescriptor_GetStringValue(... , result$cast()) stringValue = result$value()
There are still many special cases however. The SWIG documentation can help, as well as browsing the generated R code in R/ChemmineOB.R.
R version 3.2.3 (2015-12-10) Platform: x86_64-pc-linux-gnu (64-bit) Running under: Ubuntu 14.04.3 LTS
locale:  LC_CTYPE=en_US.UTF-8 LC_NUMERIC=C LC_TIME=en_US.UTF-8
 LC_COLLATE=C LC_MONETARY=en_US.UTF-8 LC_MESSAGES=en_US.UTF-8
 LC_PAPER=en_US.UTF-8 LC_NAME=C LC_ADDRESS=C
 LC_TELEPHONE=C LC_MEASUREMENT=en_US.UTF-8 LC_IDENTIFICATION=C
attached base packages:  stats graphics grDevices utils datasets methods base
other attached packages:  ChemmineOB_1.8.2 BiocStyle_1.8.0
loaded via a namespace (and not attached):  zlibbioc_1.16.0 magrittr_1.5 formatR_1.2.1 htmltools_0.3 tools_3.2.3
 yaml_2.1.13 codetools_0.2-14 stringi_1.0-1 rmarkdown_0.9.2 knitr_1.11
 stringr_1.0.0 digest_0.6.8 evaluate_0.8
This software was developed with funding from the National Science Foundation: ABI-0957099, 2010-0520325 and IGERT-0504249.
Backman, T W, Y Cao, and T Girke. 2011. “ChemMine tools: an online service for analyzing and clustering small molecules.” Nucleic Acids Res 39 (Web Server issue): 486–91. doi:10.1093/nar/gkr320.
Cao, Y, A Charisi, L C Cheng, T Jiang, and T Girke. 2008. “ChemmineR: a compound mining framework for R.” Bioinformatics 24 (15): 1733–34. doi:10.1093/bioinformatics/btn307.
Wang, Y, T W Backman, K Horan, and T Girke. 2013. “fmcsR: Mismatch Tolerant Maximum Common Substructure Searching in R.” Bioinformatics, Aug. doi:10.1093/bioinformatics/btt475.