Tab. 1. Characteristic substructures for each module (.
Fig. 4) as determined by modular frequency x inverse chemical frequency (MF_ICF)
Orange = Hierarchic Element Counts. Grey = Rings in a canonic extended smallest set of smallest rings (ESSR) ring set. Green = Simple atom nearest neighbors. Blue = SMARTS patterns. High MF_ICF numbers indicate stronger relationships between the given module and substructure.
| FP | MF_ICF | FP | MF_ICF | FP | MF_ICF |
|---|---|---|---|---|---|
| Module 0 | Module 1 | Module 2 | |||
| O=C-O-C:C | 0.92 | C-O-C-C=C | 0.25 | O=C-C-N-C | 0.49 |
| OC1C(O)CCCC1 | 0.88 | C=C-C-O-C | 0.25 | ≥1 Fe | 0.31 |
| Oc1c(O)cccc1 | 0.87 | O=C-C=C-[#1] | 0.18 | O=C-C-N | 0.3 |
| Cc1c(O)cccc1 | 0.84 | O=C-C=C | 0.16 | ≥1 Cu | 0.26 |
| O-C:C-O-[#1] | 0.83 | O-C-C=C | 0.15 | N-C-C-N-C | 0.23 |
| O-C:C-O | 0.82 | C-C-O-C-C | 0.13 | O-C-C-N-C | 0.22 |
| O=C-C:C-O | 0.8 | O(~C)(~C) | 0.11 | N-C-C-N | 0.2 |
| O-C:C-O-C | 0.8 | ≥1 Sn | 0.11 | O-C-C-N | 0.16 |
| C-C:C-O-[#1] | 0.77 | C(-C)(-O)(=O) | 0.1 | ≥2 Na | 0.16 |
| Cc1ccc(O)cc1 | 0.75 | C(-O)(=O) | 0.09 | ≥8 O | 0.15 |
| Module 3 | Module 4 | Module 5 | |||
| Nc1c(Cl)cccc1 | 0.87 | O-C-C=O | 0.33 | S=C-N-[#1] | 0.33 |
| NC1C(Cl)CCCC1 | 0.87 | O=C-C-O | 0.33 | C-S-C:C | 0.32 |
| O=C-C-C-C-C(N)-C | 0.86 | O=C-C-C-O | 0.24 | C(~N)(:C)(:C) | 0.31 |
| C-C=N-N-C | 0.85 | O-C-C-C=O | 0.24 | Cc1ccc(N)cc1 | 0.31 |
| N-N-C:C | 0.84 | ≥1 Zr | 0.22 | N-C-C-C:C | 0.31 |
| N(~C)(~H)(~N) | 0.84 | O=C-C-O-C | 0.18 | N-C-C:C-C | 0.31 |
| C=N-N-C | 0.83 | O-C-C-O-[#1] | 0.18 | N-C-C:C | 0.3 |
| N(~H)(~N) | 0.79 | ≥1 Pb | 0.17 | CC1CCC(N)CC1 | 0.3 |
| N-N-C-C | 0.79 | O=C-C-C-C-O | 0.17 | C(-C)(-N)(=C) | 0.3 |
| ≥5 unsaturated non-aromatic carbon-only ring size 6 | 0.71 | O-C-C-O | 0.16 | N-C:C:C-C | 0.29 |
| Module 6 | Module 7 | Module 8 | |||
| O=C-C-C-C-C-C | 0.33 | Cc1ccc(S)cc1 | 0.29 | CC1CC(O)CC1 | 0.97 |
| ≥1 Sn | 0.32 | CC1CCC(S)CC1 | 0.29 | CC1C(O)CCC1 | 0.97 |
| O=C-C-C-C-C | 0.32 | N-S-C:C | 0.28 | ≥3 saturated or aromatic carbon-only ring size 6 | 0.93 |
| O-O | 0.31 | C(~C)(~H)(~P) | 0.25 | ≥2 saturated or aromatic carbon-only ring size 6 | 0.75 |
| O=C-C-C-C-C-C-C | 0.29 | Cc1ccc(C)cc1 | 0.24 | ≥2 saturated or aromatic carbon-only ring size 5 | 0.74 |
| O-C-C-C-C-C-C-C | 0.29 | C(-C)(-Cl)(=O) | 0.2 | CC1C(C)CCC1 | 0.71 |
| O=C-C-C-C | 0.29 | N-S | 0.18 | ≥1 saturated or aromatic carbon-only ring size 5 | 0.71 |
| C(-C)(-O)(=O) | 0.28 | C(-C)(-H)(=O) | 0.18 | CC1CC(C)CC1 | 0.69 |
| O-C-C-C-C-C-C | 0.27 | C-P | 0.17 | CC1CC(O)CCC1 | 0.53 |
| O-C-C-C-C-C | 0.27 | S-C:C-C | 0.14 | ≥1 saturated or aromatic carbon-only ring size 6 | 0.48 |