Open Babel: An open chemical toolbox

Noel M. O’Boyle, Michael Banck, Craig A. James, Chris Morley, Tim Vandermeersch, Geoffrey Hutchison · Journal of Cheminformatics · 2011 · chemistry · 10.1186/1758-2946-3-33 · record o-boyle2011-open-babel-an-open-chemical-toolbo
tag layer · index · concepts · authors · עברית
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Other fields define these differently the same word, defined another way in another discipline
SMILES 2 fields

Tags on this paper

Every tag the record carries, each linking to every other paper in the corpus that carries it. A tag appears here whether or not its words occur in the article — the spans below are only the ones a sentence in this paper licenses. Of the 19 concept tags on this paper, all 19 are grounded in a quoted sentence.
Open Babel interconversion Chemical Markup Language canonical representation canonical numbering canonicalization kekulization stereochemistry aromaticity covalent radii Tanimoto coefficient substructures structural similarity XML dialect SMILES test suite OELib OEChem file formats BOND CONNECTIVITY FROM GEOMETRY ALONE: atoms closer than the sum of their covalent radii plus 0.45 angstrom are bonded, which is what lets formats that store no bonding at all be read as molecules AROMATICITY IS WITHHELD UNLESS A KEKULE PATTERN EXISTS: the ring is only called aromatic when a well-defined valence-bond assignment can be found, so the label is earned by a construction rather than asserted from ring membership AN EXPONENTIAL SEARCH WITH A DELIBERATE GIVE-UP: kekulisation terminates at 30 levels of recursion or 15 seconds, so a large fused ring system returns no answer rather than hanging SUBSTRUCTURE SEARCH BY HASHED BIT-STRING: every linear and ring substructure of length 1 to 7 is mapped onto 1024 bits, so a query's bits must all be set in any target that contains it system-or-tool-building
Method, as described: an open-source C++ library with formats as plugins, validated by a round-trip over 18,084 structures and a nightly test suite

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claim typeclaim_typethe shape of the claim: existence, mechanism, method, critique, prediction, null
concept edgeconcept_edgesan asserted relation between two concepts, with the sentence asserting it
conceptconceptsan idea the paper works with, quoted where the paper uses it
contributioncontributionwhat the paper claims to add
controlcontrolsan experiment run to eliminate a rival explanation
limitationlimitationswhat the paper says its evidence cannot support
mechanismmechanismshow the reported effect is said to come about
methodmethodhow the paper produced its evidence
object of studyobject_of_studywhat the paper is about — the thing it investigates
phenomenonphenomenonthe effect or regularity under study
research questionresearch_questionthe question the paper sets itself
sensesensesa distinct use of a term, quoted where the paper fixes it

The paper

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Every tag on this page

claim_type 1 · concept_edges 2 · concepts 19 · contribution 1 · controls 2 · limitations 4 · mechanisms 4 · method 1 · object_of_study 1 · phenomenon 1 · research_question 1 · senses 2

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facettagfieldconf.whose words
object_of_studythe interconversion of chemical structures between file formats, and the 111 formats Open Babel implements
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object_of_studythe paper's words
research_questionhow a single toolkit can read and write the many incompatible representations of molecular data
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research_questionthe paper's words
contributionOpen Babel itself, described for the first time, with a round-trip validation taking the error rate from 8% to 0.01%
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contributionthe paper's words
claim_typemethod
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claim_typethe paper's words
phenomenonthe proliferation of incompatible chemical file formats, which a standard failed to resolve
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phenomenonthe paper's words
methodsystem-or-tool-building
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methodthe paper's words
mechanismsmechanisms
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mechanisms[0]0.95the tagger's words
mechanismsmechanisms
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mechanisms[1]0.95the tagger's words
mechanismsmechanisms
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mechanisms[2]0.95the tagger's words
mechanismsmechanisms
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mechanisms[3]0.95the tagger's words
limitationsTWO round-trip failures remain at 0.01%, and the paper names both: a kekulisation error in a polycyclic aromatic with heteroatoms, and a bridgehead-carbon stereochemistry case
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limitations[0]0.95the tagger's words
limitationsMolecules outside the pharmaceutical mainstream - radicals, organometallics, inorganics, coordinate and 3-center 2-electron bonds - are stated to be poorly supported, and not only by this toolkit
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limitations[1]0.95the tagger's words
limitationsKekulisation is exponential and is CUT OFF at 30 levels of recursion or 15 seconds, so large fused ring systems are a known non-answer
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limitations[2]0.95the tagger's words
limitationsThe standard that was meant to remove the problem did not take: CML exists and is not widely used, which is the premise the whole toolkit rests on
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limitations[3]0.95the tagger's words
controlsa round-trip over 18,084 PubChem3D structures: SDF to SMILES to canonical SMILES, compared against SDF straight to canonical SMILES
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eliminates: errors anywhere in reading SDF, reading and writing SMILES, and canonicalisation - by making two routes to the same answer disagree · outcome (stated by the tagger, no quotation): held
controls[0]0.95the tagger's words
controlsa nightly test suite of 60 programs, each with tens to hundreds of tests
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eliminates: regressions between releases · outcome (stated by the tagger, no quotation): held
controls[1]0.95the tagger's words
conceptsOpen Babel
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also in: Open Babel
concepts[0]0.95the paper's words
conceptsinterconversion
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concepts[1]0.95the paper's words
conceptsChemical Markup Language
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concepts[2]0.95the paper's words
conceptscanonical representation
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concepts[3]0.95the paper's words
conceptscanonical numbering
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concepts[4]0.95the paper's words
conceptscanonicalization
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concepts[5]0.95the paper's words
conceptskekulization
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also in: kekulization
concepts[6]0.95the paper's words
conceptsstereochemistry
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concepts[7]0.95the paper's words
conceptsaromaticity
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also in: aromaticity
concepts[8]0.95the paper's words
conceptscovalent radii
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concepts[9]0.95the paper's words
conceptsTanimoto coefficient
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concepts[10]0.95the paper's words
conceptssubstructures
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also in: substructures
concepts[11]0.95the paper's words
conceptsstructural similarity
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concepts[12]0.95the paper's words
conceptsXML dialect
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also in: XML dialect
concepts[13]0.95the paper's words
conceptsSMILES
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also in: SMILES
concepts[14]0.95the paper's words
conceptstest suite
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also in: test suite
concepts[15]0.95the paper's words
conceptsOELib
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also in: OELib
concepts[16]0.95the paper's words
conceptsOEChem
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also in: OEChem
concepts[17]0.95the paper's words
conceptsfile formats
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also in: file formats
concepts[18]0.95the paper's words
sensescanonical representation - A CHOICE, NOT A FACT ABOUT THE MOLECULE: the same structure has N! orderings that encode exactly the same information, and canonicalisation picks one so it can be used as a database key
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senses[0]0.95the tagger's words
sensesfailure - IN THIS PAPER A ROUND-TRIP DISAGREEMENT, not a wrong answer: two routes to the same canonical SMILES are compared against each other, and the second of the two residual failures is a case where BOTH strings are correct and the algorithm merely failed to choose
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senses[1]0.95the tagger's words
concept_edgesChemical Markup Language —is-a→ XML dialect
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strength of the relation: 1
concept_edges[0]the tagger's words
concept_edgesstructural similarity —operationalised-as→ Tanimoto coefficient
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strength of the relation: 1
concept_edges[2]the tagger's words

Interpretive choices

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