BIOVIA Direct

Technical Note T47-2023

September 2023

Clarification on the ENHANCEDSTEREOSMI global property introduced with BIOVIA Direct 2023

Program

BIOVIA Direct 2023 and later

Operating System

All operating systems supported by BIOVIA Direct 2023 and later

Background

BIOVIA Direct 2023 introduced the new global property ENHANCEDSTEREOSMI. According to the documentation, the SMILES operator and the MDLAUX.SMILES function return SMILES strings with enhanced stereochemistry extensions when the property is set. The new property is switched OFF by default. This description is incomplete.

Solution

When the new global property ENHANCEDSTEREOSMI was introduced with BIOVIA Direct 2023 (DIR-4176), the Product Release Document stated only that this property applies to the SMILES operator and the MDLAUX.SMILES function. In fact, this property impacts all BIOVIA Direct operators and functions that handle SMILES strings, in particular those that read SMILES strings, like the operators mol() or similar(), and functions like mdlaux.iupacname() or mdlaux.smilestomolfile(). For details on which operators and functions handle SMILES strings please consult the BIOVIA Direct Reference Guide and the BIOVIA Direct Administration Guide.

In BIOVIA Direct 2023, the new global property ENHANCEDSTEREOSMI is switched OFF by default. For operators that create SMILES strings this means that they return NULL when the input molecule contains enhanced stereochemistry. However, operators and functions that read SMILES strings ignore the SMILES enhanced stereochemistry extensions when the ENHANCEDSTEREOSMI global property is switched OFF. This resembles the behavior of BIOVIA Direct 2022 SP1 and earlier where the functionality to handle SMILES enhanced stereochemistry extensions was not yet available.

You can switch ON the global property by using the mdlaux.setproperty() procedure. Login to the Oracle account that owns the BIOVIA Direct version, e.g. C$DIRECT2023, and run the following command:

execute mdlauxop.setproperty('ENHANCEDSTEREOSMI');

For details on the mdlauxop.setproperty() procedure please consult the BIOVIA Direct Administration Guide.

As an additional note, BIOVIA Direct 2024 will introduce the eponymous ENHANCEDSTEREOSMI flag, which allows to set the behavior of the property on the Oracle session level.

How to contact BIOVIA Support

If you have any questions, please contact BIOVIA Support.