Unexpected generated molecule with double cuts MMPDB

[alicecapecchi]

Hi! I am getting an unexpected generated molecule when using double cuts. The transformation, which in this case is the linker, is attached the wrong way around (details below). I would really appreciate your help :)

Using the two following molecules to create an MMPDB c1ccc(cc1)c2ccc3c(c2)c(c(cc3NCc4cn5cc(cnc5n4)F)c6ccccc6)c7ccccc7 test1 c1ccc(cc1)c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7 test2

to then generate new molecules from the molecule to improve c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7

the following molecule is proposed Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1

while the expected generated molecule would be c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7.

Please let me know if any other information is needed to better understand my issue. Thanks a lot, Alice

[KramerChristian]

Hi Alice,

I am not sure whether I understand your issue: The 3rd and the 5th SMILES string in your question are exactly the same - if you start with c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7 and apply a double-cut transformation, why would you expect to get c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7?

Without knowing the details, I assume you the database you create indexes a double-cut transformation that replace one nitrogen heteorcycle with a single-fluorinated form of the other. The constant parts are one *F, and the large aromatic system. If you apply this transformation to yoru starting SMILES (e.g. the 3rd SMILES), you woudl expect to get exactly the fourth SMILES.

If this is not clear, please post the transformation SMILES that is applied to produce the molecule that surprises you.

Bests, Christian

[alicecapecchi]

Hi Christian,

I must have copy pasted the same molecules twice by mistake, sorry for the confusion!

the expected molecules would be Fc1cnc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cn2c1.

And I agree that the 4th smiles has the correct transformation, but it is attached the wrong way around!

Sorry again and I hope this clarifies my question!

[KramerChristian]

Hi Alice,

can you share the command you use to get the new compounds created and the full output if you run it with the --explain or --save-details option?

Thanks, Christian

[alicecapecchi]

Sure :)

mmpdb fragment example_dataset_double_cut.smi -o test_double_cut.fragments

(where example_dataset_double_cut.smi are the SMILES: c1ccc(cc1)c2ccc3c(c2)c(c(cc3NCc4cn5cc(cnc5n4)F)c6ccccc6)c7ccccc7 test1 c1ccc(cc1)c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7 test2)

mmpdb index test_double_cut.fragments -o test_double_cut.mmpdb

mmpdb transform --smiles 'c2ccc3c(c2)c(c(cc3NCc4[nH]c5c(n4)ccc(c5F)F)c6ccccc6)c7ccccc7' test_double_cut.mmpdb --explain

Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=6, variable_symmetry_class='1', variable_smiles='c1ccccc1', attachment_order='0', constant_num_heavies=29, constant_symmetry_class='1', constant_smiles='c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc12', constant_with_H_smiles='Fc1ccc2nc(CNc3cc(-c4ccccc4)cc4ccccc34)[nH]c2c1F') variable 'c1ccccc1' not found as SMILES '[:1]c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=29, variable_symmetry_class='1', variable_smiles='c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc12', attachment_order='0', constant_num_heavies=6, constant_symmetry_class='1', constant_smiles='c1ccccc1', constant_with_H_smiles='c1ccccc1') variable 'c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc12' not found as SMILES '[:1]c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=23, variable_symmetry_class='12', variable_smiles='c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1', attachment_order='01', constant_num_heavies=12, constant_symmetry_class='11', constant_smiles='c1ccccc1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:1]c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1[:2]' variable 'c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:2]c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=10, variable_symmetry_class='123', variable_smiles='c1cc()c2ccccc2c1', attachment_order='102', constant_num_heavies=25, constant_symmetry_class='122', constant_smiles='NCc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc()c2ccccc2c1' not found as SMILES '[:1]c1cc([:2])c2ccccc2c1[:3]' variable 'c1cc()c2ccccc2c1' not found as SMILES '[:1]c1cc([:3])c2ccccc2c1[:2]' variable 'c1cc()c2ccccc2c1' not found as SMILES '[:2]c1cc([:1])c2ccccc2c1[:3]' variable 'c1cc()c2ccccc2c1' not found as SMILES '[:2]c1cc([:3])c2ccccc2c1[:1]' variable 'c1cc()c2ccccc2c1' not found as SMILES '[:3]c1cc([:1])c2ccccc2c1[:2]' variable 'c1cc()c2ccccc2c1' not found as SMILES '[:3]c1cc([:2])c2ccccc2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=11, variable_symmetry_class='123', variable_smiles='Nc1cc()c()c2ccccc12', attachment_order='012', constant_num_heavies=24, constant_symmetry_class='122', constant_smiles='Cc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1.c1ccccc1', constant_with_H_smiles=None) variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:1]Nc1cc([:2])c([:3])c2ccccc12' variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:1]Nc1cc([:3])c([:2])c2ccccc12' variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:2]Nc1cc([:1])c([:3])c2ccccc12' variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:2]Nc1cc([:3])c([:1])c2ccccc12' variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:3]Nc1cc([:1])c([:2])c2ccccc12' variable 'Nc1cc()c()c2ccccc12' not found as SMILES '[:3]Nc1cc([:2])c([:1])c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=12, variable_symmetry_class='123', variable_smiles='CNc1cc()c()c2ccccc12', attachment_order='201', constant_num_heavies=23, constant_symmetry_class='112', constant_smiles='c1ccccc1.c1ccccc1.c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:1]CNc1cc([:2])c([:3])c2ccccc12' variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:1]CNc1cc([:3])c([:2])c2ccccc12' variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:2]CNc1cc([:1])c([:3])c2ccccc12' variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:2]CNc1cc([:3])c([:1])c2ccccc12' variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:3]CNc1cc([:1])c([:2])c2ccccc12' variable 'CNc1cc()c()c2ccccc12' not found as SMILES '[:3]CNc1cc([:2])c([:1])c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=22, variable_symmetry_class='123', variable_smiles='c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1', attachment_order='102', constant_num_heavies=13, constant_symmetry_class='122', constant_smiles='F.c1ccccc1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:1]c1cc(NCc2nc3ccc([:2])c(F)c3[nH]2)c2ccccc2c1[:3]' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:1]c1cc(NCc2nc3ccc([:3])c(F)c3[nH]2)c2ccccc2c1[:2]' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:2]c1cc(NCc2nc3ccc([:1])c(F)c3[nH]2)c2ccccc2c1[:3]' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:2]c1cc(NCc2nc3ccc([:3])c(F)c3[nH]2)c2ccccc2c1[:1]' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:3]c1cc(NCc2nc3ccc([:1])c(F)c3[nH]2)c2ccccc2c1[:2]' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1' not found as SMILES '[:3]c1cc(NCc2nc3ccc([:2])c(F)c3[nH]2)c2ccccc2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=22, variable_symmetry_class='123', variable_smiles='c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1', attachment_order='102', constant_num_heavies=13, constant_symmetry_class='122', constant_smiles='F.c1ccccc1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:1]c1cc(NCc2nc3ccc(F)c([:2])c3[nH]2)c2ccccc2c1[:3]' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:1]c1cc(NCc2nc3ccc(F)c([:3])c3[nH]2)c2ccccc2c1[:2]' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:2]c1cc(NCc2nc3ccc(F)c([:1])c3[nH]2)c2ccccc2c1[:3]' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:2]c1cc(NCc2nc3ccc(F)c([:3])c3[nH]2)c2ccccc2c1[:1]' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:3]c1cc(NCc2nc3ccc(F)c([:1])c3[nH]2)c2ccccc2c1[:2]' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1' not found as SMILES '[:3]c1cc(NCc2nc3ccc(F)c([:2])c3[nH]2)c2ccccc2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=16, variable_symmetry_class='12', variable_smiles='c1cc(-c2ccccc2)c()c2ccccc12', attachment_order='01', constant_num_heavies=19, constant_symmetry_class='12', constant_smiles='NCc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:1]c1cc(-c2ccccc2)c([:2])c2ccccc12' variable 'c1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:2]c1cc(-c2ccccc2)c([:1])c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=17, variable_symmetry_class='12', variable_smiles='Nc1cc(-c2ccccc2)c()c2ccccc12', attachment_order='01', constant_num_heavies=18, constant_symmetry_class='12', constant_smiles='Cc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1', constant_with_H_smiles=None) variable 'Nc1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:1]Nc1cc(-c2ccccc2)c([:2])c2ccccc12' variable 'Nc1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:2]Nc1cc(-c2ccccc2)c([:1])c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=18, variable_symmetry_class='12', variable_smiles='CNc1cc(-c2ccccc2)c()c2ccccc12', attachment_order='10', constant_num_heavies=17, constant_symmetry_class='12', constant_smiles='c1ccccc1.c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'CNc1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:1]CNc1cc(-c2ccccc2)c([:2])c2ccccc12' variable 'CNc1cc(-c2ccccc2)c()c2ccccc12' not found as SMILES '[:2]CNc1cc(-c2ccccc2)c([:1])c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=28, variable_symmetry_class='12', variable_smiles='c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1F', attachment_order='01', constant_num_heavies=7, constant_symmetry_class='12', constant_smiles='F.c1ccccc1', constant_with_H_smiles=None) variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1F' not found as SMILES '[:1]c1ccc2nc(CNc3cc(-c4ccccc4)c([:2])c4ccccc34)[nH]c2c1F' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1F' not found as SMILES '[:2]c1ccc2nc(CNc3cc(-c4ccccc4)c([:1])c4ccccc34)[nH]c2c1F' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=27, variable_symmetry_class='123', variable_smiles='c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1', attachment_order='021', constant_num_heavies=8, constant_symmetry_class='112', constant_smiles='F.F.c1ccccc1', constant_with_H_smiles=None) variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:1]c1ccc2nc(CNc3cc(-c4ccccc4)c([:2])c4ccccc34)[nH]c2c1[:3]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:1]c1ccc2nc(CNc3cc(-c4ccccc4)c([:3])c4ccccc34)[nH]c2c1[:2]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:2]c1ccc2nc(CNc3cc(-c4ccccc4)c([:1])c4ccccc34)[nH]c2c1[:3]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:2]c1ccc2nc(CNc3cc(-c4ccccc4)c([:3])c4ccccc34)[nH]c2c1[:1]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:3]c1ccc2nc(CNc3cc(-c4ccccc4)c([:1])c4ccccc34)[nH]c2c1[:2]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c()c4ccccc34)[nH]c2c1' not found as SMILES '[:3]c1ccc2nc(CNc3cc(-c4ccccc4)c([:2])c4ccccc34)[nH]c2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=28, variable_symmetry_class='12', variable_smiles='c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc12', attachment_order='10', constant_num_heavies=7, constant_symmetry_class='12', constant_smiles='F.c1ccccc1', constant_with_H_smiles=None) variable 'c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc12' not found as SMILES '[:1]c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c([:2])c3[nH]2)c2ccccc12' variable 'c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc12' not found as SMILES '[:2]c1c(-c2ccccc2)cc(NCc2nc3ccc(F)c([:1])c3[nH]2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=6, variable_symmetry_class='1', variable_smiles='c1ccccc1', attachment_order='0', constant_num_heavies=29, constant_symmetry_class='1', constant_smiles='c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1-c1ccccc1', constant_with_H_smiles='Fc1ccc2nc(CNc3ccc(-c4ccccc4)c4ccccc34)[nH]c2c1F') variable 'c1ccccc1' not found as SMILES '[:1]c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=29, variable_symmetry_class='1', variable_smiles='c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1-c1ccccc1', attachment_order='0', constant_num_heavies=6, constant_symmetry_class='1', constant_smiles='c1ccccc1', constant_with_H_smiles='c1ccccc1') variable 'c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc(NCc2nc3ccc(F)c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=16, variable_symmetry_class='12', variable_smiles='c1cc()c2ccccc2c1-c1ccccc1', attachment_order='10', constant_num_heavies=19, constant_symmetry_class='12', constant_smiles='NCc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc()c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc([:2])c2ccccc2c1-c1ccccc1' variable 'c1cc()c2ccccc2c1-c1ccccc1' not found as SMILES '[:2]c1cc([:1])c2ccccc2c1-c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=17, variable_symmetry_class='12', variable_smiles='Nc1cc()c(-c2ccccc2)c2ccccc12', attachment_order='01', constant_num_heavies=18, constant_symmetry_class='12', constant_smiles='Cc1nc2ccc(F)c(F)c2[nH]1.c1ccccc1', constant_with_H_smiles=None) variable 'Nc1cc()c(-c2ccccc2)c2ccccc12' not found as SMILES '[:1]Nc1cc([:2])c(-c2ccccc2)c2ccccc12' variable 'Nc1cc()c(-c2ccccc2)c2ccccc12' not found as SMILES '[:2]Nc1cc([:1])c(-c2ccccc2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=18, variable_symmetry_class='12', variable_smiles='CNc1cc()c(-c2ccccc2)c2ccccc12', attachment_order='10', constant_num_heavies=17, constant_symmetry_class='12', constant_smiles='c1ccccc1.c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'CNc1cc()c(-c2ccccc2)c2ccccc12' not found as SMILES '[:1]CNc1cc([:2])c(-c2ccccc2)c2ccccc12' variable 'CNc1cc()c(-c2ccccc2)c2ccccc12' not found as SMILES '[:2]CNc1cc([:1])c(-c2ccccc2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=28, variable_symmetry_class='12', variable_smiles='c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1-c1ccccc1', attachment_order='10', constant_num_heavies=7, constant_symmetry_class='12', constant_smiles='F.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc(NCc2nc3ccc([:2])c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:2]c1cc(NCc2nc3ccc([:1])c(F)c3[nH]2)c2ccccc2c1-c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=27, variable_symmetry_class='123', variable_smiles='c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1', attachment_order='201', constant_num_heavies=8, constant_symmetry_class='112', constant_smiles='F.F.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc(NCc2nc3ccc([:2])c([:3])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc(NCc2nc3ccc([:3])c([:2])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:2]c1cc(NCc2nc3ccc([:1])c([:3])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:2]c1cc(NCc2nc3ccc([:3])c([:1])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:3]c1cc(NCc2nc3ccc([:1])c([:2])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc()c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:3]c1cc(NCc2nc3ccc([:2])c([:1])c3[nH]2)c2ccccc2c1-c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=28, variable_symmetry_class='12', variable_smiles='c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1-c1ccccc1', attachment_order='10', constant_num_heavies=7, constant_symmetry_class='12', constant_smiles='F.c1ccccc1', constant_with_H_smiles=None) variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:1]c1cc(NCc2nc3ccc(F)c([:2])c3[nH]2)c2ccccc2c1-c1ccccc1' variable 'c1cc(NCc2nc3ccc(F)c()c3[nH]2)c2ccccc2c1-c1ccccc1' not found as SMILES '[:2]c1cc(NCc2nc3ccc(F)c([:1])c3[nH]2)c2ccccc2c1-c1ccccc1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=13, variable_symmetry_class='1', variable_smiles='NCc1nc2ccc(F)c(F)c2[nH]1', attachment_order='0', constant_num_heavies=22, constant_symmetry_class='1', constant_smiles='c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles='c1ccc(-c2ccc3ccccc3c2-c2ccccc2)cc1') variable 'NCc1nc2ccc(F)c(F)c2[nH]1' not found as SMILES '[:1]NCc1nc2ccc(F)c(F)c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=22, variable_symmetry_class='1', variable_smiles='c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', attachment_order='0', constant_num_heavies=13, constant_symmetry_class='1', constant_smiles='NCc1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles='NCc1nc2ccc(F)c(F)c2[nH]1') variable 'c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' not found as SMILES '[:1]c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='11', variable_smiles='N', attachment_order='01', constant_num_heavies=34, constant_symmetry_class='12', constant_smiles='Cc1nc2ccc(F)c(F)c2[nH]1.c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'N' not found as SMILES '[:1]N[:2]' variable 'N' not found as SMILES '[:2]N[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=2, variable_symmetry_class='12', variable_smiles='CN', attachment_order='10', constant_num_heavies=33, constant_symmetry_class='12', constant_smiles='c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'CN' not found as SMILES '[:1]CN[:2]' variable 'CN' not found as SMILES '[:2]CN[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=12, variable_symmetry_class='12', variable_smiles='NCc1nc2ccc()c(F)c2[nH]1', attachment_order='10', constant_num_heavies=23, constant_symmetry_class='12', constant_smiles='F.c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'NCc1nc2ccc()c(F)c2[nH]1' not found as SMILES '[:1]NCc1nc2ccc([:2])c(F)c2[nH]1' variable 'NCc1nc2ccc()c(F)c2[nH]1' not found as SMILES '[:2]NCc1nc2ccc([:1])c(F)c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=11, variable_symmetry_class='123', variable_smiles='NCc1nc2ccc()c()c2[nH]1', attachment_order='201', constant_num_heavies=24, constant_symmetry_class='112', constant_smiles='F.F.c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]NCc1nc2ccc([:2])c([:3])c2[nH]1' variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]NCc1nc2ccc([:3])c([:2])c2[nH]1' variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]NCc1nc2ccc([:1])c([:3])c2[nH]1' variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]NCc1nc2ccc([:3])c([:1])c2[nH]1' variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]NCc1nc2ccc([:1])c([:2])c2[nH]1' variable 'NCc1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]NCc1nc2ccc([:2])c([:1])c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=12, variable_symmetry_class='12', variable_smiles='NCc1nc2ccc(F)c()c2[nH]1', attachment_order='10', constant_num_heavies=23, constant_symmetry_class='12', constant_smiles='F.c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'NCc1nc2ccc(F)c()c2[nH]1' not found as SMILES '[:1]NCc1nc2ccc(F)c([:2])c2[nH]1' variable 'NCc1nc2ccc(F)c()c2[nH]1' not found as SMILES '[:2]NCc1nc2ccc(F)c([:1])c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=12, variable_symmetry_class='1', variable_smiles='Cc1nc2ccc(F)c(F)c2[nH]1', attachment_order='0', constant_num_heavies=23, constant_symmetry_class='1', constant_smiles='Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles='Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12') variable 'Cc1nc2ccc(F)c(F)c2[nH]1' not found as SMILES '[:1]Cc1nc2ccc(F)c(F)c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=23, variable_symmetry_class='1', variable_smiles='Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', attachment_order='0', constant_num_heavies=12, constant_symmetry_class='1', constant_smiles='Cc1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles='Cc1nc2ccc(F)c(F)c2[nH]1') variable 'Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' not found as SMILES '[:1]Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='11', variable_smiles='C', attachment_order='01', constant_num_heavies=34, constant_symmetry_class='12', constant_smiles='Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'C' not found as SMILES '[:1]C[:2]' variable 'C' not found as SMILES '[:2]C[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=11, variable_symmetry_class='12', variable_smiles='Cc1nc2ccc()c(F)c2[nH]1', attachment_order='10', constant_num_heavies=24, constant_symmetry_class='12', constant_smiles='F.Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'Cc1nc2ccc()c(F)c2[nH]1' not found as SMILES '[:1]Cc1nc2ccc([:2])c(F)c2[nH]1' variable 'Cc1nc2ccc()c(F)c2[nH]1' not found as SMILES '[:2]Cc1nc2ccc([:1])c(F)c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=10, variable_symmetry_class='123', variable_smiles='Cc1nc2ccc()c()c2[nH]1', attachment_order='201', constant_num_heavies=25, constant_symmetry_class='112', constant_smiles='F.F.Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]Cc1nc2ccc([:2])c([:3])c2[nH]1' variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]Cc1nc2ccc([:3])c([:2])c2[nH]1' variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]Cc1nc2ccc([:1])c([:3])c2[nH]1' variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]Cc1nc2ccc([:3])c([:1])c2[nH]1' variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]Cc1nc2ccc([:1])c([:2])c2[nH]1' variable 'Cc1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]Cc1nc2ccc([:2])c([:1])c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=11, variable_symmetry_class='12', variable_smiles='Cc1nc2ccc(F)c()c2[nH]1', attachment_order='10', constant_num_heavies=24, constant_symmetry_class='12', constant_smiles='F.Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'Cc1nc2ccc(F)c()c2[nH]1' not found as SMILES '[:1]Cc1nc2ccc(F)c([:2])c2[nH]1' variable 'Cc1nc2ccc(F)c()c2[nH]1' not found as SMILES '[:2]Cc1nc2ccc(F)c([:1])c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=11, variable_symmetry_class='1', variable_smiles='c1nc2ccc(F)c(F)c2[nH]1', attachment_order='0', constant_num_heavies=24, constant_symmetry_class='1', constant_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12') variable 'c1nc2ccc(F)c(F)c2[nH]1' not found as SMILES '[:1]c1nc2ccc(F)c(F)c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=24, variable_symmetry_class='1', variable_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', attachment_order='0', constant_num_heavies=11, constant_symmetry_class='1', constant_smiles='c1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles='Fc1ccc2nc[nH]c2c1F') variable 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' not found as SMILES '[:1]CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=10, variable_symmetry_class='12', variable_smiles='c1nc2ccc()c(F)c2[nH]1', attachment_order='01', constant_num_heavies=25, constant_symmetry_class='12', constant_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F', constant_with_H_smiles=None) variable 'c1nc2ccc()c(F)c2[nH]1' not found as SMILES '[:1]c1nc2ccc([:2])c(F)c2[nH]1' variable 'c1nc2ccc()c(F)c2[nH]1' matches SMILES '[:2]c1nc2ccc([:1])c(F)c2[nH]1' (id 2) Evaluating 1 possible rule SMILES: ['21'] Evaluate constant 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' with permutation '21' against rules using SMILES [:2]c1nc2ccc([:1])c(F)c2[nH]1 (2) Processing fragment Fragmentation(num_cuts=3, enumeration_label='N', variable_num_heavies=9, variable_symmetry_class='123', variable_smiles='c1nc2ccc()c()c2[nH]1', attachment_order='012', constant_num_heavies=26, constant_symmetry_class='122', constant_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F.F', constant_with_H_smiles=None) variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]c1nc2ccc([:2])c([:3])c2[nH]1' variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:1]c1nc2ccc([:3])c([:2])c2[nH]1' variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]c1nc2ccc([:1])c([:3])c2[nH]1' variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:2]c1nc2ccc([:3])c([:1])c2[nH]1' variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]c1nc2ccc([:1])c([:2])c2[nH]1' variable 'c1nc2ccc()c()c2[nH]1' not found as SMILES '[:3]c1nc2ccc([:2])c([:1])c2[nH]1' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=10, variable_symmetry_class='12', variable_smiles='c1nc2ccc(F)c()c2[nH]1', attachment_order='01', constant_num_heavies=25, constant_symmetry_class='12', constant_smiles='CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F', constant_with_H_smiles=None) variable 'c1nc2ccc(F)c()c2[nH]1' not found as SMILES '[:1]c1nc2ccc(F)c([:2])c2[nH]1' variable 'c1nc2ccc(F)c()c2[nH]1' matches SMILES '[:2]c1nc2ccc(F)c([:1])c2[nH]1' (id 3) Evaluating 1 possible rule SMILES: ['21'] Evaluate constant 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' with permutation '21' against rules using SMILES [:2]c1nc2ccc(F)c([:1])c2[nH]1 (3) Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='1', variable_smiles='F', attachment_order='0', constant_num_heavies=34, constant_symmetry_class='1', constant_smiles='c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1F', constant_with_H_smiles='Fc1cccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c12') variable 'F' not found as SMILES '[:1]F' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=34, variable_symmetry_class='1', variable_smiles='c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1F', attachment_order='0', constant_num_heavies=1, constant_symmetry_class='1', constant_smiles='F', constant_with_H_smiles='F') variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1F' not found as SMILES '[:1]c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1F' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=33, variable_symmetry_class='12', variable_smiles='c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1', attachment_order='01', constant_num_heavies=2, constant_symmetry_class='11', constant_smiles='F.F', constant_with_H_smiles=None) variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1' not found as SMILES '[:1]c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1[:2]' variable 'c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1' not found as SMILES '[:2]c1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='1', variable_smiles='F', attachment_order='0', constant_num_heavies=34, constant_symmetry_class='1', constant_smiles='c1c(F)ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c12', constant_with_H_smiles='Fc1ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c2c1') variable 'F' not found as SMILES '[:1]F' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=1, enumeration_label='N', variable_num_heavies=34, variable_symmetry_class='1', variable_smiles='c1c(F)ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c12', attachment_order='0', constant_num_heavies=1, constant_symmetry_class='1', constant_smiles='F', constant_with_H_smiles='F') variable 'c1c(F)ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c12' not found as SMILES '[:1]c1c(F)ccc2nc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)[nH]c12' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='11', variable_smiles='N', attachment_order='01', constant_num_heavies=34, constant_symmetry_class='12', constant_smiles='c1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.Cc1nc2ccc(F)c(F)c2[nH]1', constant_with_H_smiles=None) variable 'N' not found as SMILES '[:1]N[:2]' variable 'N' not found as SMILES '[:2]N[:1]' No matching rule SMILES found. Skipping fragment. Processing fragment Fragmentation(num_cuts=2, enumeration_label='N', variable_num_heavies=1, variable_symmetry_class='11', variable_smiles='C', attachment_order='01', constant_num_heavies=34, constant_symmetry_class='12', constant_smiles='c1nc2ccc(F)c(F)c2[nH]1.Nc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12', constant_with_H_smiles=None) variable 'C' not found as SMILES '[:1]C[:2]' variable 'C' not found as SMILES '[:2]C[:1]' No matching rule SMILES found. Skipping fragment. Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 1: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' Rule 2: 'CNc1cc(-c2ccccc2)c(-c2ccccc2)c2ccccc12.F' + '[:1]c1cnc2nc([:2])cn2c1' -> 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' == Product SMILES in database: 1 == Evaluating the 12 rule environments for 'Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1' ID SMILES 1 Fc1cn2cc(CNc3cc(-c4ccccc4)c(-c4ccccc4)c4ccccc34)cnc2n1

Thanks for your help! Alice