And since we're on the topic, what do you do if a sample is racemic?

So it sounds like you want a Set/Get/HasChiralFlag (or perhaps
HasKnownAbsoluteStereo). If a molecule doesn't have a chiral flag, we
should call IsChiral (as Geoff has done) and use that value.

- Noel

On 6 June 2011 17:05, Dave Nunn <[email protected]> wrote:
> Thanks for your help!
> The way the flag is used in the pharmaceutical industry, the only real way
> to determine the setting is by assertion. We are not trying to track so much
> wether a given center is stereogenic,  as whether, in a given sample, the
> stereochemistry is known in an absolute or relative sense. That information
> is not knowable from first principles, only from the sample originator. So
> if the input format is mol or sdf, I would propagate the setting that is
> there. Not sure what other formats track the same concept.
> I agree it is difficult decision with other formats. Many utilities will set
> the flag ON if, for example, a SMILES string contains any '@' symbols, but
> that leads to errors in the other direction (too many flags, rather than too
> few). In previous work, I relied on conventions within the SMILES name to
> track the concept.
> Hmm -- I didn't see any api calls in the documentation.
> $obmol->SetChiral(1), $obmol->SetChiral(0), $obmol->GetChiral() to allow
> manipulation. On the last, you must distinguish whether you're asking if the
> molecule contains any stereogenic centers, or whether it's stereochemistry
> is in a known state for a given sample.
> I'm afraid I'm still just a perl hacker -- need to understand OB much better
> to even try to contribute code :-(
>
> -- David S. Nunn, PhD
> Office: 845-512-8359
> Cell:    845-480-1346
> [email protected]
> On Sun, Jun 5, 2011 at 11:43 AM, Noel O'Boyle <[email protected]> wrote:
>>
>> You're right. We just set that to zero whatever the input. Open Babel
>> does not have code to determine whether a molecule is chiral or not.
>>
>> - Noel
>>
>> On 5 June 2011 02:19, dave.nunn <[email protected]> wrote:
>> > Am I missing an option, or is OB tromping on my chiral flag?
>> > Using Open Babel 2.3.0, as the script below shows, a mol file
>> > with chiral flag set is read in, but when written out, it is gone?
>> >
>> > -- Dave Nunn
>> >
>> > #!/usr/bin/perl
>> > use strict;
>> > use Chemistry::OpenBabel;
>> > undef($/);
>> > my $molfile = <DATA>;
>> > my $obmol = new Chemistry::OpenBabel::OBMol;
>> > my $obconversion = new Chemistry::OpenBabel::OBConversion;
>> > $obconversion->SetInAndOutFormats('sdf', 'sdf');
>> > $obconversion->ReadString($obmol, $molfile);
>> > print $obconversion->WriteString($obmol);
>> > __END__
>> > (S)-2-butanol
>> >  OpenBabel06041121052D
>> >
>> >  6  5  0  0  1  0  0  0  0  0999 V2000
>> >   -1.7321    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
>> >   -1.7321    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
>> >   -2.2321   -0.8660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
>> >   -2.7321    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
>> >   -0.8660   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
>> >    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
>> >  1  2  1  0  0  0  0
>> >  2  3  1  6  0  0  0
>> >  2  4  1  0  0  0  0
>> >  2  5  1  0  0  0  0
>> >  5  6  1  0  0  0  0
>> > M  END
>> >
>
>

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