CORAL: QSPR Models for Solubility of C60 and C70 Fullerene Derivatives

7

CORAL: QSPR models for solubility of [C60] and [C70] fullerene derivatives

Alla. P. Toropovaa, Andrey A. Toropova,*, Emilio Benfenatia, Giuseppina Ginib

Danuta Leszczynskac, Jerzy Leszczynskid

aIstituto di Ricerche Farmacologiche Mario Negri, 20156, Via La Masa 19, Milano, Italy

b Department of Electronics and Information, Politecnico di Milano, piazza Leonardo da Vinci 32, 20133 Milano, Italy

c Interdisciplinary Nanotoxicity Center, Department of Civil and Environmental Engineering, Jackson State University, 1325 Lynch St, Jackson, MS 39217-0510, USA

d Interdisciplinary Nanotoxicity Center, Department of Chemistry and Biochemistry, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS 39217, USA

Supplementary Materials

Table S1: Correlation weights for calculation of the DCW for Split A, B, and C

Table S2: Experimental and calculated using Eq. 3 values of solubility, S, [mg/mL].

Table S3: Example of DCW(1) calculation for structure #1 (Split A, Threshold=1, run 1)

Table S1

Correlation weights for calculation of the DCW for Split A, B, and C. Nt and Nv are the numbers of SMILES which contain the Sk in the training and validation sets, respectively

No. / Sk / CW(Sk) in Run 1 / CW(Sk) in Run 2 / CW(Sk) in Run 3 / Nt / Nv
Split A
Promoters of S-increase
1 / %10xxxxxxxxx / 1.1453429 / 1.3373575 / 1.3840674 / 18 / 9
2 / %11xxxxxxxxx / 1.5910738 / 1.6364813 / 1.4613070 / 18 / 9
3 / %12xxxxxxxxx / 1.2705182 / 1.2212362 / 1.7511666 / 18 / 9
4 / %13xxxxxxxxx / 0.9661997 / 1.3482267 / 1.2139939 / 18 / 9
5 / %14xxxxxxxxx / 1.3469500 / 1.0019415 / 0.7968895 / 18 / 9
6 / %15xxxxxxxxx / 1.1651473 / 1.4277443 / 1.1207158 / 18 / 9
7 / %16xxxxxxxxx / 1.2920243 / 1.5649773 / 1.6143608 / 18 / 9
8 / %17xxxxxxxxx / 1.2991579 / 1.9876282 / 0.8915078 / 18 / 9
9 / %18xxxxxxxxx / 1.4975631 / 1.5527506 / 1.1711283 / 18 / 9
10 / %19xxxxxxxxx / 1.2982315 / 1.8274074 / 0.9650326 / 18 / 9
11 / %20xxxxxxxxx / 1.6795798 / 1.0794394 / 1.0579335 / 18 / 9
12 / %21xxxxxxxxx / 1.1478151 / 1.5334526 / 0.9887004 / 18 / 9
13 / %22xxxxxxxxx / 1.5012721 / 1.5508597 / 1.8606603 / 18 / 9
14 / %23xxxxxxxxx / 1.4765208 / 0.8024699 / 1.0126546 / 18 / 9
15 / %24xxxxxxxxx / 1.8478812 / 1.5577355 / 1.2339514 / 18 / 9
16 / %25xxxxxxxxx / 1.9167691 / 1.0093546 / 1.7863080 / 18 / 9
17 / %26xxxxxxxxx / 1.7141456 / 1.2899851 / 2.0986801 / 18 / 9
18 / %27xxxxxxxxx / 1.3957506 / 1.7362215 / 1.8546270 / 18 / 9
19 / %28xxxxxxxxx / 1.4875698 / 2.0373624 / 0.8829945 / 18 / 9
20 / %29xxxxxxxxx / 1.5215529 / 1.7380535 / 2.2540003 / 18 / 9
21 / %30xxxxxxxxx / 1.7754810 / 1.0899071 / 1.4848870 / 18 / 9
22 / %31xxxxxxxxx / 1.2130746 / 1.5859851 / 2.2836964 / 18 / 9
23 / %32xxxxxxxxx / 1.6077469 / 1.2045361 / 1.2825477 / 18 / 9
24 / %33xxxxxxxxx / 0.4468354 / 0.3986409 / 0.3979644 / 16 / 8
25 / %34xxxxxxxxx / 3.7619363 / 3.3411343 / 3.3340277 / 6 / 2
26 / %35xxxxxxxxx / 0.3383474 / 1.3670600 / 0.6126509 / 5 / 2
27 / %36xxxxxxxxx / 1.1655105 / 0.8045352 / 0.8418284 / 5 / 2
28 / %37xxxxxxxxx / 0.9022305 / 0.6339174 / 1.0781661 / 5 / 2
29 / %38xxxxxxxxx / 0.5646984 / 0.4872137 / 0.4028279 / 5 / 2
30 / 1xxxxxxxxxxx / 1.9527443 / 1.5285404 / 1.6041951 / 18 / 9
31 / 2xxxxxxxxxxx / 1.1023453 / 1.3510934 / 1.3223444 / 18 / 9
32 / 3xxxxxxxxxxx / 1.7254371 / 1.1850425 / 1.5353802 / 18 / 9
33 / 4xxxxxxxxxxx / 1.6347942 / 1.0647790 / 2.2978649 / 18 / 9
34 / 5xxxxxxxxxxx / 1.3883926 / 1.3137637 / 1.6736009 / 18 / 9
35 / 6xxxxxxxxxxx / 0.9745578 / 1.3044445 / 1.2077674 / 18 / 9
36 / 7xxxxxxxxxxx / 1.7917942 / 1.0853641 / 2.0581489 / 18 / 9
37 / 8xxxxxxxxxxx / 1.3277509 / 2.0511801 / 1.4758848 / 18 / 9
38 / 9xxxxxxxxxxx / 1.6450191 / 1.5120495 / 2.0141242 / 18 / 9
39 / =xxxxxxxxxxx / 1.9043363 / 2.1763485 / 2.0327063 / 18 / 9
40 / Cxxxxxxxxxxx / 1.1735754 / 1.1276199 / 1.0579815 / 18 / 9
41 / cxxxxxxxxxxx / 0.8988809 / 1.0377557 / 0.9549886 / 18 / 9
42 / oxxxxxxxxxxx / 7.2997131 / 6.7728724 / 6.8289684 / 1 / 0
43 / sxxxxxxxxxxx / 4.8540374 / 4.1519411 / 4.4005211 / 3 / 4
Promoters of S-decrease
1 / (xxxxxxxxxxx / -0.6394074 / -0.8476021 / -0.7203954 / 18 / 9
2 / Oxxxxxxxxxxx / -0.4081089 / -0.3870552 / -0.3741362 / 16 / 8
Undefined
1 / -xxxxxxxxxxx / -0.0385801 / 0.2357046 / 0.0613300 / 1 / 0
2 / [xxxxxxxxxxx / 0.0333465 / -0.0951645 / -0.0287676 / 1 / 0
Split B
Promoters of S-increase
1 / %10xxxxxxxxx / 0.8138968 / 1.0247721 / 1.3399604 / 18 / 9
2 / %11xxxxxxxxx / 1.2605177 / 1.1474792 / 1.3734437 / 18 / 9
3 / %12xxxxxxxxx / 1.0973306 / 1.5970491 / 1.2983285 / 18 / 9
4 / %13xxxxxxxxx / 1.7543303 / 1.3874007 / 2.0727961 / 18 / 9
5 / %14xxxxxxxxx / 1.5084643 / 1.6333282 / 1.2663663 / 18 / 9
6 / %15xxxxxxxxx / 1.2346148 / 1.5546006 / 1.2479442 / 18 / 9
7 / %16xxxxxxxxx / 1.4667805 / 1.2205791 / 2.0172958 / 18 / 9
8 / %17xxxxxxxxx / 1.2347307 / 1.7382698 / 1.2605147 / 18 / 9
9 / %18xxxxxxxxx / 0.8703706 / 1.1242869 / 1.3871526 / 18 / 9
10 / %19xxxxxxxxx / 1.1744182 / 1.9725493 / 1.5842588 / 18 / 9
11 / %20xxxxxxxxx / 0.9709168 / 1.9115401 / 1.7003654 / 18 / 9
12 / %21xxxxxxxxx / 1.4673079 / 1.1788605 / 1.7912467 / 18 / 9
13 / %22xxxxxxxxx / 1.5042292 / 1.4421550 / 1.1622332 / 18 / 9
14 / %23xxxxxxxxx / 1.7360446 / 1.0738925 / 1.2042744 / 18 / 9
15 / %24xxxxxxxxx / 1.6830701 / 1.6029270 / 1.1160561 / 18 / 9
16 / %25xxxxxxxxx / 0.9899478 / 1.3524405 / 1.2605080 / 18 / 9
17 / %26xxxxxxxxx / 1.2081340 / 1.2997367 / 1.3662994 / 18 / 9
18 / %27xxxxxxxxx / 1.3032868 / 2.1099867 / 1.6545067 / 18 / 9
19 / %28xxxxxxxxx / 1.0213176 / 1.8657046 / 1.4172419 / 18 / 9
20 / %29xxxxxxxxx / 1.6911054 / 2.0597445 / 1.2341456 / 18 / 9
21 / %30xxxxxxxxx / 1.3872052 / 1.7827599 / 1.3034713 / 18 / 9
22 / %31xxxxxxxxx / 1.5009659 / 1.3672384 / 1.7249827 / 18 / 9
23 / %32xxxxxxxxx / 1.1008715 / 1.1857348 / 1.4511892 / 18 / 9
24 / %33xxxxxxxxx / 0.4048717 / 0.3992345 / 0.4016488 / 16 / 8
25 / %34xxxxxxxxx / 4.3845462 / 4.2667988 / 4.4994789 / 6 / 2
26 / %35xxxxxxxxx / 1.5203450 / 0.9873382 / 1.0882698 / 5 / 2
27 / %36xxxxxxxxx / 0.8292701 / 1.4080762 / 2.3978267 / 5 / 2
28 / %37xxxxxxxxx / 1.5950538 / 1.6092243 / 1.0531222 / 5 / 2
29 / %38xxxxxxxxx / 1.6397706 / 1.4910215 / 1.6271527 / 5 / 2
30 / 1xxxxxxxxxxx / 1.2652995 / 1.2132751 / 1.6700777 / 18 / 9
31 / 2xxxxxxxxxxx / 1.7502520 / 1.6082959 / 1.4885075 / 18 / 9
32 / 3xxxxxxxxxxx / 1.3046172 / 1.5522522 / 1.4201963 / 18 / 9
33 / 4xxxxxxxxxxx / 1.4288998 / 1.1645732 / 0.9606926 / 18 / 9
34 / 5xxxxxxxxxxx / 1.2547995 / 1.0377700 / 1.1227005 / 18 / 9
35 / 6xxxxxxxxxxx / 1.6452556 / 1.4386841 / 1.2841984 / 18 / 9
36 / 7xxxxxxxxxxx / 1.0774367 / 1.7952560 / 1.9631077 / 18 / 9
37 / 8xxxxxxxxxxx / 1.2584201 / 1.1373776 / 1.5003949 / 18 / 9
38 / 9xxxxxxxxxxx / 1.4665954 / 1.8705714 / 1.8712463 / 18 / 9
39 / =xxxxxxxxxxx / 1.9256072 / 2.1508562 / 2.2461311 / 18 / 9
40 / Cxxxxxxxxxxx / 1.1730592 / 1.3982799 / 1.3589572 / 18 / 9
41 / cxxxxxxxxxxx / 0.5540548 / 0.7959561 / 0.7240082 / 18 / 9
42 / oxxxxxxxxxxx / 6.6004613 / 6.9780117 / 7.1295117 / 1 / 0
43 / sxxxxxxxxxxx / 2.9723006 / 2.9007333 / 2.9138190 / 5 / 2
Promoters of S-decrease
1 / (xxxxxxxxxxx / -0.5826161 / -0.7208721 / -0.7499429 / 18 / 9
2 / -xxxxxxxxxxx / -0.7767223 / -0.5580612 / -0.6492215 / 1 / 0
3 / Oxxxxxxxxxxx / -0.2991354 / -0.2724978 / -0.2260985 / 16 / 8
4 / [xxxxxxxxxxx / -0.1669729 / -0.1653307 / -0.2957747 / 1 / 0
Split C
Promoters of S-increase
1 / %10xxxxxxxxx / 1.1994790 / 1.4168757 / 1.0462731 / 18 / 9
2 / %11xxxxxxxxx / 1.4265858 / 1.3095409 / 1.6346622 / 18 / 9
3 / %12xxxxxxxxx / 1.5383596 / 1.1165436 / 1.4871504 / 18 / 9
4 / %13xxxxxxxxx / 1.0124303 / 1.3956390 / 1.2628176 / 18 / 9
5 / %14xxxxxxxxx / 1.2637968 / 0.7950304 / 1.9023618 / 18 / 9
6 / %15xxxxxxxxx / 1.0107323 / 1.7865756 / 1.5265014 / 18 / 9
7 / %16xxxxxxxxx / 1.5136084 / 1.0523296 / 1.2086840 / 18 / 9
8 / %17xxxxxxxxx / 1.1523978 / 1.0741663 / 0.9914815 / 18 / 9
9 / %18xxxxxxxxx / 1.3504650 / 1.0133180 / 1.2746945 / 18 / 9
10 / %19xxxxxxxxx / 1.4517907 / 1.5720994 / 1.5158983 / 18 / 9
11 / %20xxxxxxxxx / 1.2328094 / 1.8620280 / 1.1526670 / 18 / 9
12 / %21xxxxxxxxx / 1.4420578 / 1.3738065 / 2.0205392 / 18 / 9
13 / %22xxxxxxxxx / 1.1275967 / 1.5610207 / 1.4539464 / 18 / 9
14 / %23xxxxxxxxx / 1.6718912 / 1.5619202 / 1.2632345 / 18 / 9
15 / %24xxxxxxxxx / 2.1394376 / 1.5141627 / 1.3860287 / 18 / 9
16 / %25xxxxxxxxx / 1.8479089 / 1.2496040 / 1.9547459 / 18 / 9
17 / %26xxxxxxxxx / 1.4658027 / 1.3504821 / 1.3119425 / 18 / 9
18 / %27xxxxxxxxx / 1.6046762 / 1.5583642 / 1.2703805 / 18 / 9
19 / %28xxxxxxxxx / 1.3921481 / 1.3884043 / 1.4593551 / 18 / 9
20 / %29xxxxxxxxx / 1.4654357 / 1.6376093 / 1.1606966 / 18 / 9
21 / %30xxxxxxxxx / 1.8860536 / 1.2879430 / 1.3224802 / 18 / 9
22 / %31xxxxxxxxx / 1.1577358 / 1.4900788 / 1.5104381 / 18 / 9
23 / %32xxxxxxxxx / 1.9100743 / 1.2977090 / 1.4162233 / 18 / 9
24 / %33xxxxxxxxx / 0.1012262 / 0.1537000 / 0.1041216 / 16 / 8
25 / %34xxxxxxxxx / 4.6033914 / 4.4657732 / 4.1884327 / 6 / 2
26 / %35xxxxxxxxx / 1.0517898 / 0.6463179 / 1.4288782 / 5 / 2
27 / %36xxxxxxxxx / 0.6993670 / 0.9253704 / 0.2045183 / 5 / 2
28 / %37xxxxxxxxx / 0.7387902 / 0.6969633 / 0.4270944 / 5 / 2
29 / %38xxxxxxxxx / 0.7616466 / 1.1375064 / 0.8909115 / 5 / 2
30 / 1xxxxxxxxxxx / 1.0726102 / 1.2759194 / 1.4778073 / 18 / 9
31 / 2xxxxxxxxxxx / 1.2968183 / 1.0095841 / 1.5737720 / 18 / 9
32 / 3xxxxxxxxxxx / 1.4274931 / 1.6007564 / 0.9599921 / 18 / 9
33 / 4xxxxxxxxxxx / 1.6634041 / 1.6160662 / 1.3089928 / 18 / 9
34 / 5xxxxxxxxxxx / 1.4124560 / 1.5608685 / 1.3255725 / 18 / 9
35 / 6xxxxxxxxxxx / 1.3267713 / 1.8837142 / 1.9167411 / 18 / 9
36 / 7xxxxxxxxxxx / 1.1364746 / 1.5649426 / 1.7083753 / 18 / 9
37 / 8xxxxxxxxxxx / 1.6373723 / 1.3827305 / 1.5652081 / 18 / 9
38 / 9xxxxxxxxxxx / 0.9849941 / 1.0856416 / 1.0362032 / 18 / 9
39 / =xxxxxxxxxxx / 1.7899092 / 1.8737522 / 1.6979498 / 18 / 9
40 / Cxxxxxxxxxxx / 1.1292164 / 1.2455742 / 1.1361116 / 18 / 9
41 / cxxxxxxxxxxx / 0.7029777 / 0.8085086 / 0.7241513 / 18 / 9
42 / oxxxxxxxxxxx / 7.5956986 / 7.5982892 / 7.3299079 / 1 / 0
43 / sxxxxxxxxxxx / 3.5136907 / 3.2869833 / 3.2724072 / 5 / 2
Promoters of S-decrease
1 / (xxxxxxxxxxx / -0.5026000 / -0.6047591 / -0.4975177 / 18 / 9
2 / Oxxxxxxxxxxx / -0.5470864 / -0.5090010 / -0.4480683 / 16 / 8
Undefined
1 / -xxxxxxxxxxx / 0.0 / 0.0 / 0.0 / 0 / 1
2 / [xxxxxxxxxxx / 0.0 / 0.0 / 0.0 / 0 / 1

Table S2

Experimental and calculated using Eq. 3 values of solubility, S, [mg/mL].

No. / SMILES / DCW(1) / SExpr / SCalc / SExpr-SCalc / Relative error (%)
Training set
1 / O=C(OC)CCCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 225.5672352 / 50.000 / 23.128 / 26.872 / 54
2 / O=C(OCC)CCCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 226.7408106 / 19.000 / 31.498 / -12.498 / -66
4 / O=C(OC)CCCC%31(c1ccco1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 230.4714368 / 58.000 / 58.107 / -0.107 / -0
5* / O=C(OC)CCCC%37(c1ccccc1)C%32%38C4c%36c3c2c%34C%21=C%18c2c%14c%16c3C4=C%31C%17C%10=C%30C=%29C=9c8c%22c%24c7c5c%25c%27c%20c6c%19c%13c%12c(c56)c7c8C=%11C=9C%10=C%15C(C=%11%12)=C%13C(C%14=C%15C%16%17)=C%18C%19=C%20C%21=C%28C%35=C%33C%26=C%23C(=C(C=%29C%22=C%23c%24c%25C%26=C%27%28)C%32=C%30%31)C%37%38C%33c%36c%34%35 / 226.7805714 / 80.000 / 31.782 / 48.218 / 60
7 / O=C(OCC)CCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 225.5672352 / 5.000 / 23.128 / -18.128 / -363
8 / O=C(OCCC)CCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 226.7408106 / 43.000 / 31.498 / 11.502 / 27
10 / O=C(OCCCC)CCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 227.9143860 / 30.000 / 39.869 / -9.869 / -33
11 / O=C(OCc1ccccc1)CCC%22(c2ccccc2)C%33%23C%32C=%20C=%34C=%18C%16=C6c5c%15c%14c%13c4c3c%12C%11=C9C=8C3=C(c45)C7=C6C=%34C%31=C7C=8C%30=C9C=%29C(C%10=C%21C=%17C=%25C%28=C%10C=%29C%11=C%27c%12c%13C%26=C%14C=%24C(=C%15%16)C%19=C(C=%17C(C=%20C=%18%19)C%21%22%23)C=%24C=%25C%26=C%27%28)=C%33C%30=C%31%32 / 237.3108178 / 106.000 / 106.888 / -0.888 / -1
13 / O=C(OC)CCC%37(c1ccccc1)C%32%38C4c%36c3c2c%34C%21=C%18c2c%14c%16c3C4=C%31C%17C%10=C%30C=%29C=9c8c%22c%24c7c5c%25c%27c%20c6c%19c%13c%12c(c56)c7c8C=%11C=9C%10=C%15C(C=%11%12)=C%13C(C%14=C%15C%16%17)=C%18C%19=C%20C%21=C%28C%35=C%33C%26=C%23C(=C(C=%29C%22=C%23c%24c%25C%26=C%27%28)C%32=C%30%31)C%37%38C%33c%36c%34%35 / 225.6069960 / 12.000 / 23.411 / -11.411 / -95
14 / O=C(OCC)CCC%37(c1ccccc1)C%32%38C4c%36c3c2c%34C%21=C%18c2c%14c%16c3C4=C%31C%17C%10=C%30C=%29C=9c8c%22c%24c7c5c%25c%27c%20c6c%19c%13c%12c(c56)c7c8C=%11C=9C%10=C%15C(C=%11%12)=C%13C(C%14=C%15C%16%17)=C%18C%19=C%20C%21=C%28C%35=C%33C%26=C%23C(=C(C=%29C%22=C%23c%24c%25C%26=C%27%28)C%32=C%30%31)C%37%38C%33c%36c%34%35 / 226.7805714 / 10.000 / 31.782 / -21.782 / -218
16 / O=C(OCCCC)CCC%37(c1ccccc1)C%32%38C4c%36c3c2c%34C%21=C%18c2c%14c%16c3C4=C%31C%17C%10=C%30C=%29C=9c8c%22c%24c7c5c%25c%27c%20c6c%19c%13c%12c(c56)c7c8C=%11C=9C%10=C%15C(C=%11%12)=C%13C(C%14=C%15C%16%17)=C%18C%19=C%20C%21=C%28C%35=C%33C%26=C%23C(=C(C=%29C%22=C%23c%24c%25C%26=C%27%28)C%32=C%30%31)C%37%38C%33c%36c%34%35 / 229.1277222 / 30.000 / 48.523 / -18.523 / -62
17 / O=C(OCC)CCC%31(c1cccs1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 228.0257611 / 23.000 / 40.663 / -17.663 / -77
19 / O=C(OCCCC)CCC%31(c1cccs1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 230.3729119 / 70.000 / 57.404 / 12.596 / 18
20 / O=C(OCCC)CCC%38(c1cccs1)C%36%37C%28c%11c%27c2c%26C%23=C%34c2c%12C=%10C=%35C=9c%21c8c3c%20c%19c4c3c7c6c5c4C=%18C%17=C5C%16=C%15C6=C%13c7c8C=9C=%14C=%10C(c%11%12)C%37%38C(C%13=%14)=C%15C%36=C%29C%16=C%30C%17=C%33C=%25C=%18c%19c%24c%22c%20c%21C(=C%22C%23=C(C%24=%25)C=%32c%26c%31c%27C%28=C%29C%30C%31C=%32%33)C%34=%35 / 239.9065824 / 130.000 / 125.402 / 4.598 / 4
22 / CCCCCCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 226.9315069 / 31.000 / 32.858 / -1.858 / -6
23 / CCCCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 224.5843561 / 23.000 / 16.118 / 6.882 / 30
25 / [O-]C(=O)CCC%26(CCC([O-])=O)C%32%25C%15=C%13C=%21C%12=C%23C=3C=%11c2c%10c9c1c8c7c6c4c1c2C=5C=3C=%22C%18=C(C4=5)C%17=C6C%16=C7C%27=C%29C8=C9C=%30C%14=C%10C=%11C%12=C%13C%14=C%31C%15=C%28C%32C=%20C(C%16=C%19C%17=C%18C=%24C(C%19=%20)C%25%26C=%21C=%24C=%22%23)=C%27C%28=C%29C=%30%31 / 222.8770135 / 4.000 / 3.940 / 0.060 / 2
26 / O=C(OCC)C%26(C(=O)OCCOC)C%32%25C%15=C%13C=%21C%12=C%23C=3C=%11c2c%10c9c1c8c7c6c4c1c2C=5C=3C=%22C%18=C(C4=5)C%17=C6C%16=C7C%27=C%29C8=C9C=%30C%14=C%10C=%11C%12=C%13C%14=C%31C%15=C%28C%32C=%20C(C%16=C%19C%17=C%18C=%24C(C%19=%20)C%25%26C=%21C=%24C=%22%23)=C%27C%28=C%29C=%30%31 / 223.5862542 / 11.000 / 8.999 / 2.001 / 18
Validation set
3 / O=C(OC)CCCC%31(c1cccs1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 228.0257611 / 36.000 / 40.663 / -4.663 / -13
6 / O=C(OC)CCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 224.3936598 / 10.000 / 14.757 / -4.757 / -48
9 / CC(C)OC(=O)CCC%21(c1ccccc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 225.4619958 / 22.000 / 22.377 / -0.377 / -2
12 / O=C(OC)CCC%21(c1ccc(OC)cc1)C%32%22C%31C=%19C=%33C=%17C%15=C5c4c%14c%13c%12c3c2c%11C%10=C8C=7C2=C(c34)C6=C5C=%33C%30=C6C=7C%29=C8C=%28C(C9=C%20C=%16C=%24C%27=C9C=%28C%10=C%26c%11c%12C%25=C%13C=%23C(=C%14%15)C%18=C(C=%16C(C=%19C=%17%18)C%20%21%22)C=%23C=%24C%25=C%26%27)=C%32C%29=C%30%31 / 223.8803115 / 5.000 / 11.096 / -6.096 / -122
15 / O=C(OCCC)CCC%37(c1ccccc1)C%32%38C4c%36c3c2c%34C%21=C%18c2c%14c%16c3C4=C%31C%17C%10=C%30C=%29C=9c8c%22c%24c7c5c%25c%27c%20c6c%19c%13c%12c(c56)c7c8C=%11C=9C%10=C%15C(C=%11%12)=C%13C(C%14=C%15C%16%17)=C%18C%19=C%20C%21=C%28C%35=C%33C%26=C%23C(=C(C=%29C%22=C%23c%24c%25C%26=C%27%28)C%32=C%30%31)C%37%38C%33c%36c%34%35 / 227.9541468 / 35.000 / 40.152 / -5.152 / -15
18 / O=C(OCCC)CCC%31(c1cccs1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 229.1993365 / 45.000 / 49.033 / -4.033 / -9
21 / O=C(OCCCC)CCC%38(c1cccs1)C%36%37C%28c%11c%27c2c%26C%23=C%34c2c%12C=%10C=%35C=9c%21c8c3c%20c%19c4c3c7c6c5c4C=%18C%17=C5C%16=C%15C6=C%13c7c8C=9C=%14C=%10C(c%11%12)C%37%38C(C%13=%14)=C%15C%36=C%29C%16=C%30C%17=C%33C=%25C=%18c%19c%24c%22c%20c%21C(=C%22C%23=C(C%24=%25)C=%32c%26c%31c%27C%28=C%29C%30C%31C=%32%33)C%34=%35 / 241.0801578 / 124.000 / 133.772 / -9.772 / -8
24 / CCCCCCC%31(c1cccs1)C%28%30C%26C=%20C=%32C=%19C%33=C%10c3c9c2c8c7c6c5c2c4c3C%33=C%18C=%17C4=C5C%16=C%15C6=C%14C7=C%13C=%12C8=C9C%11=C%10C=%32C%27=C%11C=%12C%25=C%13C%24=C%14C%23=C%15C%22=C%16C=%17C%21=C%18C=%19C=%20C%29C%21=C%22C(=C%23C%24=C%28C%25=C%26%27)C%29%30%31 / 229.3900328 / 25.000 / 50.394 / -25.394 / -102
27 / O=C(OCCCCCCCC)C%24C%32%25C%16=C%14C%11=C%23C=%26C%13=C%20C3=C%12C=%10c2c9c8c1c7c6c5c4c1c2C3=C4C=%19C%18=C5C%17=C6C%27=C%29C7=C8C=%30C%15=C9C=%10C(C%11=C%12%13)=C%14C%15=C%31C%16=C%28C%32C=%22C(C%17=C%21C%18=C(C=%19%20)C=%26C(C%21=%22)C%23%24%25)=C%27C%28=C%29C=%30%31 / 220.8192013 / 9.000 / -10.737 / 19.737 / 219

*) Compound #5 is an outlier