Converting Smiles To Iupac Chemical Name?

Question

[dimkal]

Does anybody know of of an open source tool which can convert chemical SMILES to IUPAC name?

So for example, if i have a chemical structure for aspirin, i can convert it to a SMILES string [O=C(Oc1ccccc1C(=O)O)C], and can generate a name like: "2-acetoxybenzoic acid"?

Answer 1

[cdsouthan]

Both PubChem and ChemSpider have all three (and more) in their record structures (name, synonyms, IUPACs SMILES and InChIs). so from their web services options you should be able to convert.

Alternatively you could uploading names to chemicalize or try the Cactus NIH Chemical Identifier Resolver

http://www.chemicalize.org/

http://cactus.nci.nih.gov/chemical/structure

But why do you want to go SMILES > IUPAC when most folk want to go the other way ?

[dimkal]

thanks for your answer. do you happen to know what they're using in the backend to generate this?

I'm making an application that while you sketch a molecule it'll give you its chemical name... also i'd like to make an educational tool that would make chemical nomenclature easy to study.

[wdiwdi]

Check out http://www.xemistry.com/edit/frame.html. A freely accessible online structure editor which includes lookup of names from PubChem (plus access to dozens of other Internet structure databases).

Answer 2

[Rm]

check chemAxon Forum : https://www.chemaxon.com/forum/ftopic7844.html

[dimkal]

thanks for the comment, i also saw this post. However I was looking for an open source solution, so I can use it in another project. I updated the question to make this clear. thanks for your answer though.

Answer 3

[wdiwdi]

If 'free-for-academic-use' is good enough for you, here is a script fragment to do this with the Cactvs Chemoinformatics Toolkit www.xemistry.com/academic):

cactvs>ens get O=C(Oc1ccccc1C(=O)O)C E_IUPAC_PREFERRED_NAME
2-acetyloxybenzoic acid

Or directly from the cpd name:

cactvs>ens get [ens create 'aspirin'] E_IUPAC_PREFERRED_NAME
2-acetyloxybenzoic acid

Internally, this uses PubChem, so it is not an ab-initio name generator which also works with compounds not in a database.

There are also other properties which retrieve the other standardized name variants of a compound stored in PubChem, as well as a way to retrieve all names from the NCI resolver.

PubChem uses OpenEye software to compute the names.

[db4]

I have installed cactvstools but can't find the executable. :)

Answer 4

[Egon Willighagen]

A very long time ago, I started a framework for the Chemistry Development Kit. It had a few naming rules, but nothing substantial. Source code for IUPAC naming is still an important component missing in the arsenal of open cheminformatics functionality :(