Standalone tools provide additional SIRIUS related tasks that do not fit into the SIRIUS identification workflow. These can e.g. be configuration tasks, file conversion tasks or features that might be helpful for downstream analysis. These tool cannot be part of a toolchain and have to be executed in a separate command. Each of these tools has its own help message (sirius <TOOLNAME> -h).

Custom database tool

The custom-db tool allows you to import custom structure databases from a csv/tsv (tab separated) file with structures given in SMILES format. Optionally a database id and a name can be given.

CN1CCCC1C2=C[N+](=CC=C2)[O-]	id-01	Nicotin
CN1C=NC2=C1C(=O)N(C(=O)N2C)C	id-03	Caffein
CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3 id-05 Bicculine

You can import multiple files with compounds as SMILES into one DB. If a given structure can be found in SIRIUS’ internal structure DB then fingerprint is downloaded from there, otherwise it is computed locally on your computer which might take some time for many structures.

sirius -i <structure.tsv> cistom-db --name myDB --output /some/dir

Note, that we usually use PubChem standardized SMILES to represent the structures for our machine learning methods. PubChem standardization is not yet part of this import process. For best possible results we recommend standardizing your SMILES using the PubChem standardization before importing them, but this step is not mandatory.

Similarity tool

The similarity tool allows you to compute different similarity measures between compounds. It takes a SIRIUS project-space (or any input format SIRIUS can convert into a project such as ms, mgf or cef) as input (sirius -i <INPUT>) and calculates all against all similarity matrices for the compounds in the project-space and stores them in the given output directory given by -d.

sirius -i <project-space> similarity --cosine --ftalign --ftblast <SPECTRA_LIB> --tanimoto -d <OUTPUT>

Cosine Similarity (--cosine)

Computes the cosine similarity of the merged MS/MS between all compounds. Just the spectra are needed no additional computation have to be performed beforehand.

Fragmentation Tree alignment Similarity (--ftalign)

Computes the tree alignment score of the top ranked fragmentation tree between all compounds. To perform this computation the input project-space needs to contain the fragmentation trees from the formula/sirius subtool. So the formula subtool has to be executed beforehand. The Alignment method is described in “Identifying the Unknowns by Aligning Fragmentation Trees”

FT-Blast (--ftblast)

Computes fragmentation tree alignments between all compounds in the dataset, incorporating the given fragmentation tree library as described in “Identifying the Unknowns by Aligning Fragmentation Trees”. The input project-space needs to contain fragmentation trees computed with the formula/sirius subtool. So the formula subtool has to be executed beforehand. The given library (--ft-blast=<LIB_PATH>) can either be another SIRIUS project-space containing fragmentation trees, or a directory containing fragmentation trees in json format.

Tanimoto Similarity (--tanimoto)

Computes the tanimoto similarity of the top ranked predicted fingerprints between all compounds. The input project-space needs to contain the predicted fingerprints from the structure/fingerid subtool. So the formula and the structure subtool have to executed beforehand. Note that the fingerprints compared are probabilistic. The tanimoto computation for two probabilistic fingerprints $F$ and $F’$ of length $n$ is computed as follows:

\[\frac{ \sum_{i=1}^{n} F_i \cdot F'_i } { \sum_{i=1}^{n} 1 - (1 - F_i) \cdot (1 - F'_i) }\]
Example 1

Let’s say we want to compute --cosine, --ftalign and --tanimoto similarities. For that we need a proeject-space that contains spectra, fragmetations trees and fingerprints. So we start computing them with the following command:

sirius -i <input-data.mgf> -o <my-project> formula structure

We can now use the resulting project-space (my-project) as input for the similarity computation:

sirius -i <my-project> similarity --cosine --ftalign --tanimoto --d <output-dir>
Example 2

Let’s say we want to compute --ftblast similarities. For that we need one project-space (my-project) that contains fragmentation trees and another project-space that contains fragmentation trees for our spectral library (library-project). Assuming we use .mgf format for both, our input spectra and the library spectra, we have to execute the following commands.

Compute fragmentation trees for input data:

sirius -i <input-data.mgf> -o <my-project> sirius

Compute fragmentation trees for the library spectra:

sirius -i <library-data.mgf> -o <library-project> sirius

No we have the input we need for the --ftblast similarity computation

sirius -i <my-project> similarity --ftblast <library-project> -d <output-dir>

Mass Decomposition tool

The decomp tool provides the SIRIUS internal “Efficient mass decomposition” algorithm as standalone tool to decompose masses with given deviation, ionization, chemical alphabet and chemical filter.

MGF export tool

The mgf-export tool exports the spectra of a given input project-space as .mgf for use with other tools like GNPS. The --quant-table option allows to export an additional feature quantification table (csv), e.g. to export a SIRIUS project-space for GNPS Feature Based Molecular Networking:

sirius --input <project-space> MGF --merge-ms2 --quant-table <table.csv> --output <spectra.mgf>

Note, quantification information are only available if the source of the project-space was in mzml(mzxml).

Fragmentation tree export tool

The ftree-export tool exports the fragmentation trees of a given project-space (sirius -i <INPUT>) in various formats (--json, --dot) to a given output directory (--output <DIR>). The --all option specifies whether fragmentation trees of all formula candidates (of a compound) or only of the top formula candidate will be exported.

The following example will export the top ranked fragmentation tree of all compounds in the project space in dot format.

sirius --input <project-space> ftree-export --dot --output <output-dir>

The commandline tool Graphviz can transform .dot files into image formats (PDF, SVG, PNG etc.). After installing Graphviz you can create a .pdf files as follows:

dot -Tpdf <tree-file.dot> > <tree-file.pdf>
Foo
Fragmentation Tree exported as .dot and converted to svg.

Note: The SIRIUS GUI allows to directly export the rendered tree as vector or pixel graphics.

Project-space tool

The project-space tool Modifies a given project-space (e.g. merging, splitting, filtering, version conversion). Read project(s) with --input, apply modification and write the result via --output. If either only --input or --output is given the modifications will be made in-place.