Table 3.
Case (i): screening based on SMILES central chain and Case (ii): screening based on SMILES central N-atom neighbors (N3 atom of the pyrimidine) for chain length and atomic neighboring in longest SMILES molecular chain (LoSMoC) in upper entry and the Branching SMILES (BraS) in down entry for various versions (V’s) of SMILES based screening criteria along the molecules of Table 1, respectively. The correlation factors are given for full dependency of parameters of Table 1, i.e., A = A (χ, η, π, ω, logP), and for statistical error tolerance of 0.0001, unless otherwise indicated for the best correlation’s combination such that the Topliss-Costello rule [152] for ratio molecule-to-descriptors ≥ 4 to be generally respected (at least for χ & η as the main QSAR descriptors); the marked correlation corresponds with selected criteria and implicitly with the working molecular pool of Table 1 for each SMILES configuration (LoSMoC and BraS) and screening case (i and ii) further considered (see text).
| Index | Criteria | CASE (i) | Case (ii) | ||
|---|---|---|---|---|---|
| Molecules | RQSAR | Molecules | RQSAR | ||
| V1 LoSMoC | Between 15–16 atoms LoSMoC | 1–4, 6–11, 28 | 0.90371960 (a) | 1–9, 28 | 0.92402295 (c) |
| V1 BraS | Main chain and secondary branch with maximum 14 atoms | 2–11, 13, 14, 16, 17, 22, 28 | 0.53158997 | 2, 3, 5–9, 13, 14, 16, 17, 22, 28, 29 | 0.70384894 |
| V2 LoSMoC | Between 18–21 atoms LoSMoC | 13–17, 19, 21, 22, 24, 26, 31, 32 | 0.75180080 | 15–18, 21–23, 27, 29, 31, 32 | 0. 95150144 (b) |
| V2 BraS | Main chain and secondary branch with minimum 14 atoms | 7, 11, 12, 15–17, 19, 22, 24–26, 28, 30–32 | 0.95109419 | 7, 15–17, 20, 21, 22, 27, 28, 29, 30–32 | 0.87354213 |
| V3 LoSMoC | At least one triple bond in the main chain LoSMoC | 1–7, 9–11, 13, 14, 28, 30 | 0.56411064 | 1–4, 6, 7, 9, 13, 15, 28, 30 | 0.49202776 |
| V3 BraS | Secondary and tertiary branches with maximum 14 atoms | 2–10, 13, 14, 28 | 0.62469181 | 1–7, 9, 13, 14, 28 | 0.75756597 |
| V4 LoSMoC | More than three branches in the main chain LoSMoC | 2–4, 6–11, 19, 21, 22, 24–26, 28, 30–32 | 0.43357261 | 2–4, 6, 7, 9, 15,20–23, 27–32 | 0.61510478 |
| V4 BraS | Secondary and tertiary branches with minimum 14 atoms | 11, 15–17, 19, 21–25, 31, 32 | 0.64694148 | 15–17, 20–23, 27, 29, 31, 32 | 0.94183439 |
| V5 LoSMoC | More than four branches in the main chain LoSMoC | 7–9, 11, 19, 21, 24–26, 28, 30–32 | 0.47454364 | 7, 8, 20, 23, 27–32 | 0.71500251 (d) |
| V5 BraS | Minimum 3 tertiary branches | 6, 11, 15–17, 19, 22–26, 31, 32 | 0.94899619 | 6, 15–17, 20–23, 27, 29, 31, 32 | 0.64718879 |
| V6 LoSMoC | Ramifications of LoSMoC main chain containing groups formed only carbon and hydrogen atoms (except common = O, C = O) | 2–4, 6–10, 19, 28, 30, 31 | 0.71050966 (b) | 2–4, 6, 7, 9, 15, 20,27–31 | 0.64508095 |
| V6 BraS | Minimum 1 quaternary branching | 1, 2, 4, 6–8, 10,13–15, 19, 21–25, 28, 30–32 | 0.48549586 | 1, 2, 4, 6–8,13, 14, 20–23, 27–29, 30–32 | 0.63906586 |
| V7 LoSMoC | Ramifications of LoSMoC main chain containing groups consisting of a single atom or –CH3 groups (except common = O, C = O) | 2–7, 9, 10, 19, 22,24–26, 28, 30–32 | 0.57636501 | 2–4, 6, 7, 9, 20–22,27– 32 | 0.61600596 (e) |
| V7 BraS | One of the secondary branches with minimum one triple bond | 1–7, 9–11, 13–15, 28 | 0.63904635 | 1–7, 9, 13–15, 28 | 0.73556023 (d) |
| V8 LoSMoC | At least one branch for the last 6 points main chain LoSMoC | 2–4, 6–11, 19, 23–25, 28, 30, 32 | 0. 51837657 | 2–4, 6, 7, 9, 20, 21, 27–32 | 0.69314160 (d) |
| V8 BraS | The secondary branch linked with C2 of pyrimidinic nucleus with minimum 2 heteroatoms | 1– 6, 8–11, 13– 15 | 0.58368204 | 1–6, 8, 9, 13–15 | 0.57765388 (f) |
| V9 LoSMoC | LoSMoC main chain contains after N3 atom of the pyrimidine nucleus (central main chain LoSMoC) a group –CH2– | 1–7, 9–11, 13–15, 19, 21, 24–26, 28, 30–32 | 0.37650771 | 1–8, 13–15, 20, 21, 27–32 | 0.63047473 |
| V9 BraS | The secondary branch linked with N3 of pyrimidinic nucleus contains only C and H atoms | 1– 8, 10, 11, 13–17, 25, 26, 28, 30–32 | 0.63881109 | 1–8, 13–17, 20, 21, 27–29, 30–32 | 0.72514327 |
| V10 BraS | The secondary branch linked with N3 of pyrimidinic nucleus contains 4 Carbon atoms | 2– 4, 6 8– 10, 13, 14, 16, 19, 22, 24, 26 | 0.61480396 | 2–6, 8, 9, 13, 14, 16, 17, 22 | 0.53480139 |
| V11 BraS | The secondary branch linked with N3 of pyrimidinic nucleus contains 5–6 Carbon atoms | 7, 12, 15, 18, 21, 23, 25, 28, 30–32 | 0.66627959 | 7, 15, 18, 20, 21, 23, 28, 29, 30–32 | 0.59914507 |
| V12 BraS | The tertiary branching are formed by maximum 3 atoms of C and H | 2, 4–10, 13, 16, 19, 21–25, 28, 30–32 | 0.38470862 | 2, 4, 6–9, 13, 16–18, 20, 21, 28–32 | 0.61909773 |
| V13 BraS | The tertiary branches are formed only by C and H atoms | 2– 10, 13, 14, 16, 17, 19, 28, 30, 31 | 0.56415743 | 2–9, 13–16, 20, 27–31 | 0.64691170 |
| V14 BraS | Quaternary branching are contains only one C atom or CH3 group | 1, 2, 5–7, 21–25, 28, 30–32 | 0.57731047 | 2, 5, 6, 20–23, 27, 28, 30–32 | 0.72850903 |
| V15 BraS | A single quaternary branching with maximum 2 atoms (C/O) and H | 1, 2, 5– 7, 19, 21, 22, 28, 30, 31 | 0.93051865 | 1, 2, 5, 6, 20–22, 27, 28, 30, 31 | 0.90565106 |
(a) A = A(χ, η, ω, logP); (b) within statistical error tolerance 0.00002; (c) within statistical error tolerance 1E−25; (d) within statistical error tolerance 0.00004; (e) within statistical error tolerance 0.00008; (f) within statistical error tolerance 0.00003;