Hi Patrick,
I don't know Avogadro in detail, but as it is based on OpenBabel I can
imagine it uses an algorithm to guess bond orders from bond distances,
angles, etc., whereas the RDKit does not. In fact, if I convert a
benzene ring from SMILES to SDF through PDB format (which does not
contain any bond information once CONECT records are removed), I still
get correct bond orders; this does not happen with RDKit (which is
expected):
echo 'c1ccccc1' | babel --gen3d -i smi -o pdb | grep -v CONECT | babel
-i pdb -o sdf
yields
OpenBabel11021718533D
12 12 0 0 0 0 0 0 0 0999 V2000
-0.7600 1.1690 -0.0010 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6330 1.2450 -0.0010 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3950 0.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7640 -1.1680 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6290 -1.2430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3910 -0.0750 -0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3540 2.0790 0.0010 H 0 0 0 0 0 0 0 0 0 0 0 0
1.1240 2.2140 -0.0030 H 0 0 0 0 0 0 0 0 0 0 0 0
2.4800 0.1350 -0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
1.3580 -2.0780 0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.1200 -2.2130 -0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.4760 -0.1340 -0.0030 H 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0 0
1 7 1 0 0 0 0
2 3 2 0 0 0 0
3 9 1 0 0 0 0
3 4 1 0 0 0 0
4 10 1 0 0 0 0
5 11 1 0 0 0 0
5 4 2 0 0 0 0
6 1 2 0 0 0 0
6 5 1 0 0 0 0
8 2 1 0 0 0 0
12 6 1 0 0 0 0
M END
whereas:
mol = Chem.AddHs(Chem.MolFromSmiles('c1ccccc1'))
rdDistGeom.EmbedMolecule(mol)
molFromPDB = Chem.MolFromPDBBlock(re.sub('CONECT.*\n', '',
Chem.MolToPDBBlock(mol), flags=re.MULTILINE), removeHs = False)
print (Chem.MolToMolBlock(molFromPDB))
yields
RDKit 3D
12 12 0 0 0 0 0 0 0 0999 V2000
-0.0060 -1.3620 0.0590 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2180 -0.7080 0.0690 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2090 0.6740 -0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0030 1.3620 0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2210 0.7090 0.0760 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1960 -0.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0250 -2.4100 -0.2260 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.1060 -1.1760 0.4870 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.0910 1.1950 -0.3790 H 0 0 0 0 0 0 0 0 0 0 0 0
0.0420 2.4080 -0.2780 H 0 0 0 0 0 0 0 0 0 0 0 0
2.1030 1.1830 0.5000 H 0 0 0 0 0 0 0 0 0 0 0 0
2.0960 -1.1980 -0.3330 H 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 3 1 0
5 4 1 0
6 5 1 0
6 1 1 0
7 1 1 0
8 2 1 0
9 3 1 0
10 4 1 0
11 5 1 0
12 6 1 0
M END
Note that the RDKit gets the correct bond orders if the PDB file
contains CONECT records with duplicate (or triplicate) entries for the
relevant atom indices, which is the widely accepted (though non
official) way to encode bond orders in PDB files.
Cheers,
p.
On 11/02/17 18:45, Patrick Avery wrote:
Yes, that is probably correct. I am loading a pdb file for the initial
conformer, so bond orders are not specified.
But I find it strange, still, that when I use MMFF94 in Avogadro to
optimize it, it results in a planar shape even though all the bonds
are still single.
On Thu, Nov 2, 2017 at 2:38 PM, Paolo Tosco <paolo.to...@unito.it
<mailto:paolo.to...@unito.it>> wrote:
Dear Patrick,
my guess is that you loaded the caffeine coordinates from PDB, or
anyway from a format where bond orders were not specified. All
atoms appear to be sp3-hybridized, which results in the wrong
geometry being generated.
Hope that helps,
Paolo
On 11/02/17 18:20, Patrick Avery wrote:
Hey there RDKitters,
I have been generating conformers in RDKit, optimizing them using
MMFF94, and sorting them by their energies. For some tests, I
have been using caffeine. But I seem to have some strange
results, and I wonder if anyone knows why.
I have attached two images of an MMFF94 optimized caffeine
conformer. In them, the oxygen in the top right corner is the
primary strange thing I see (although it doesn't seem to be very
planar either, which may be somewhat strange).
Note that the oxygen is sticking out of the plane of the
molecule. This is the lowest energy conformer generated and
optimized by RDKit (and other conformers low in energy are
similar to it - with the oxygen sticking out).
If I take that exact molecule and MMFF94 optimize it in Avogadro,
all the atoms move to be in the same plane (including the oxygen
that was sticking out). So the problem goes away if I MMFF94
optimize it with Avogadro.
So the question is: why are RDKit and Avogadro giving different
results for the MMFF94 optimization? And why does RDKit's MMFF94
push the oxygen out of the plane so much?
In RDKit, I am using the C++ function
RDKit::MMFF::MMFFOptimizeMoleculeConfs().
My parameters are the mol (with all the conformers in it), an
empty result vector, 1 thread, 1000 maximum optimization
iterations, "MMFF94" for the mmffVariant, 100.0 for the nonbonded
threshold, and true for ignoreInterfragInteractions.
Let me know if anyone knows why.
Thanks,
Patrick
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