NPASS Compound

Natural Product: NPC516707

Natural Product ID	NPC516707
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{R},4~{S},5~{R},6~{R})-2-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4-dihydroxy-6-[(1~{R},2~{S},4~{S},5'~{R},6~{R},7~{S},8~{R},9~{S},12~{S},13~{S},16~{S},18~{R})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
IUPAC Name	(2~{R},3~{R},4~{S},5~{R},6~{R})-2-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4-dihydroxy-6-[(1~{R},2~{S},4~{S},5'~{R},6~{R},7~{S},8~{R},9~{S},12~{S},13~{S},16~{S},18~{R})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 137145 0 0 0 0 0 0 0 0999 V2000 11.8115 -1.9157 2.8248 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9889 -2.5216 1.6864 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2705 -1.8243 0.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2015 -0.8227 0.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8221 -1.3290 0.2982 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7869 -2.5599 0.9013 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5488 -2.4523 2.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0941 -0.4511 1.1272 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8848 -1.1504 1.1716 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7478 -0.2890 1.6566 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8022 -0.3477 0.5433 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7307 0.6748 0.4814 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9929 0.8373 1.7917 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6167 0.2253 1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7591 0.7907 0.6573 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3974 -0.1637 0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3525 0.1751 -0.6035 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5951 0.6331 -0.1994 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6677 -0.1153 -0.7825 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2698 0.6729 -1.6839 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5907 0.7750 -1.7619 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0527 2.1681 -2.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4257 2.1536 -2.2771 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9491 3.3947 -2.6490 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8222 3.7718 -1.6347 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2704 5.0624 -1.8522 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0989 5.4913 -0.6537 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1982 4.6698 -0.4492 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0457 5.2313 -3.1191 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2999 4.6003 -3.0723 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2855 4.6506 -4.2864 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1285 4.5618 -5.3877 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7578 3.2656 -3.9243 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9336 2.8201 -4.9555 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2454 0.5479 -0.4158 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7136 1.4628 0.4797 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8522 -0.8419 0.0885 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5809 -1.0136 1.2639 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3637 -0.7657 0.3377 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8323 -2.0543 0.5166 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3969 -2.3313 1.7769 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0088 -2.6202 1.7844 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5611 -2.7889 3.0723 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5812 -3.9633 3.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1354 -4.1230 4.4762 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6575 -2.9339 4.1016 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0929 -3.5274 5.2533 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7754 -3.8511 3.6594 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4637 -5.1892 3.9398 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0397 -3.6623 2.1902 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3524 -3.7732 1.8238 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6949 1.1689 -1.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6878 0.6105 -1.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5247 1.0189 -0.6292 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8121 2.4941 -0.7458 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7665 0.1770 -0.5717 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4983 0.1284 -1.8859 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6768 -0.7896 -1.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6270 -0.3836 -0.6987 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2831 0.8862 -1.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5915 -1.4695 -0.3065 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9366 -1.3583 -0.9207 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2717 -2.5678 -1.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8142 -2.3455 2.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2585 -2.1131 3.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8233 -0.8043 2.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2822 -3.5884 1.6241 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4331 -2.5572 -0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2207 -1.2511 0.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3636 0.1119 0.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3018 -0.6112 -1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2983 -1.4350 2.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2856 -3.2577 2.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9928 -2.0854 1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0805 0.7216 1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3790 -0.7866 2.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2852 -1.3539 0.5915 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1530 1.6548 0.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5734 0.2514 2.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9943 1.8855 2.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1610 0.4172 2.7567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7390 -0.8727 1.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3626 1.7743 1.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9635 -0.1227 1.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0136 -1.2172 0.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5310 -0.7174 -1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1858 -0.9502 -1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9713 0.0198 -2.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5752 2.4253 -3.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7384 2.8968 -1.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1351 4.1444 -2.8053 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3906 5.7237 -1.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4530 6.5305 -0.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4811 5.4243 0.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0659 3.7374 -0.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2050 6.3235 -3.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6924 4.6594 -3.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4218 5.3101 -4.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0480 5.3481 -5.9970 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6083 2.6025 -3.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2740 3.5459 -5.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3370 0.6683 -0.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1353 1.3737 1.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1019 -1.5543 -0.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4503 -0.5393 1.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2683 -0.1876 1.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5200 -1.5406 2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9758 -1.8868 3.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1014 -4.9196 2.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2714 -3.8286 2.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1698 -5.0314 4.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0157 -1.9419 4.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8902 -3.7494 5.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6978 -3.5879 4.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 -5.7844 3.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4800 -4.4495 1.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4162 -3.8165 0.8458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2013 1.2302 -2.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5580 2.1565 -1.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5710 -0.4984 -1.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0672 1.0351 -2.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2425 2.9812 -1.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5596 3.0525 0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8817 2.7037 -0.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4483 -0.8575 -0.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8386 -0.2817 -2.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7614 1.1497 -2.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1773 -0.7830 -2.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3144 -1.8107 -1.6140 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6256 0.7383 -2.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5577 1.7058 -1.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1123 1.2168 -0.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1889 -2.4745 -0.4267 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1310 -0.4079 -1.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8427 -3.4573 -1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7372 -2.5098 -2.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3471 -2.7218 -1.8891 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 1 6 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 21 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 17 52 1 0 52 53 1 0 53 54 1 0 54 55 1 6 54 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 6 59 61 1 0 61 62 1 0 62 63 1 0 7 2 1 0 61 9 1 0 62 5 1 0 59 11 1 0 56 12 1 0 54 15 1 0 39 19 1 0 50 41 1 0 33 24 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 6 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 7 72 1 0 7 73 1 0 9 74 1 1 10 75 1 0 10 76 1 0 11 77 1 1 12 78 1 6 13 79 1 0 13 80 1 0 14 81 1 0 14 82 1 0 15 83 1 1 16 84 1 0 16 85 1 0 17 86 1 6 19 87 1 6 21 88 1 6 22 89 1 0 22 90 1 0 24 91 1 6 26 92 1 6 27 93 1 0 27 94 1 0 28 95 1 0 29 96 1 6 30 97 1 0 31 98 1 6 32 99 1 0 33100 1 1 34101 1 0 35102 1 6 36103 1 0 37104 1 6 38105 1 0 39106 1 1 41107 1 1 43108 1 1 44109 1 0 44110 1 0 45111 1 0 46112 1 1 47113 1 0 48114 1 1 49115 1 0 50116 1 6 51117 1 0 52118 1 0 52119 1 0 53120 1 0 53121 1 0 55122 1 0 55123 1 0 55124 1 0 56125 1 1 57126 1 0 57127 1 0 58128 1 0 58129 1 0 60130 1 0 60131 1 0 60132 1 0 61133 1 1 62134 1 6 63135 1 0 63136 1 0 63137 1 0 M END

Standard InCHIKey	UTXFFSIHMAHBLN-BFWUUNFQSA-N
Standard InCHI	InChI=1S/C45H74O18/c1-19-7-12-45(57-17-19)20(2)30-26(63-45)14-25-23-6-5-21-13-22(8-10-43(21,3)24(23)9-11-44(25,30)4)58-42-39(62-41-38(55)35(52)32(49)28(16-47)60-41)36(53)33(50)29(61-42)18-56-40-37(54)34(51)31(48)27(15-46)59-40/h19-42,46-55H,5-18H2,1-4H3/t19-,20+,21-,22+,23-,24+,25+,26+,27-,28-,29-,30+,31+,32+,33+,34+,35+,36+,37-,38-,39-,40-,41+,42-,43+,44+,45-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	902.49	Volume:	868.092 ? Van der Waals volume.
Dense:	1.04	LogP:	2.119 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.931 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.738 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	48.0
TPSA:	276.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.128	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.69	Fsp³:	1.0
MCE-18:	230.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.696	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.281	Promiscuous compounds:	0.036

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.202	MDCK Permeability:	-5.233
Pgp-inhibitor:	0.0	Pgp-substrate:	0.575
PAMPA:	0.998 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.44
Plasma Protein Binding (PPB):	57.595%	Volume Distribution (VD):	-0.422
Fu:	34.003% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.097	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.395	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.506 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.549

Half-life (T1/2):

2.14

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.027
Human Hepatotoxicity (H-HT):	0.761	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	1.0
Carcinogencity:	0.422	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.997
Hematotoxicity:	0.845	Drug-induced Nephrotoxicity:	0.947
Genotoxicity:	0.069	RPMI-8226 Immunitoxicity:	0.464
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.993
BCF:	1.682 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.393 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.848 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28933	Smilax medica	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252913]
NPO28933	Smilax medica	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28933	Smilax medica	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC516707 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	26111
0.1-0.2	20173
0.2-0.3	2728
0.3-0.4	572
0.4-0.5	145
0.5-0.6	70
0.6-0.7	37
0.7-0.8	1
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC211354
0.8889	High Similarity	NPC297348
0.8889	High Similarity	NPC249204
0.8889	High Similarity	NPC48339
0.8889	High Similarity	NPC141769
0.8889	High Similarity	NPC477547
0.8452	Intermediate Similarity	NPC477451
0.8315	Intermediate Similarity	NPC160426
0.7978	Intermediate Similarity	NPC107962
0.7789	Intermediate Similarity	NPC128572
0.7753	Intermediate Similarity	NPC107188
0.7692	Intermediate Similarity	NPC6295
0.75	Intermediate Similarity	NPC234352
0.7474	Intermediate Similarity	NPC475643
0.7444	Intermediate Similarity	NPC206003
0.7444	Intermediate Similarity	NPC473610
0.7386	Intermediate Similarity	NPC325828
0.7386	Intermediate Similarity	NPC177834
0.7363	Intermediate Similarity	NPC19400
0.7303	Intermediate Similarity	NPC294686
0.7263	Intermediate Similarity	NPC475351
0.6961	Remote Similarity	NPC475625
0.6957	Remote Similarity	NPC222731
0.68	Remote Similarity	NPC471464
0.6774	Remote Similarity	NPC250393
0.67	Remote Similarity	NPC92890
0.6667	Remote Similarity	NPC97700
0.6667	Remote Similarity	NPC30856
0.6633	Remote Similarity	NPC113044
0.6633	Remote Similarity	NPC283829
0.6633	Remote Similarity	NPC161676
0.6598	Remote Similarity	NPC125324
0.6593	Remote Similarity	NPC485594
0.6559	Remote Similarity	NPC291203
0.6559	Remote Similarity	NPC217205
0.6505	Remote Similarity	NPC184617
0.6471	Remote Similarity	NPC51172
0.6471	Remote Similarity	NPC49032
0.6458	Remote Similarity	NPC54619
0.6429	Remote Similarity	NPC485595
0.6421	Remote Similarity	NPC474399
0.6389	Remote Similarity	NPC132080
0.6364	Remote Similarity	NPC195297
0.6224	Remote Similarity	NPC264101
0.6214	Remote Similarity	NPC477809
0.62	Remote Similarity	NPC141433
0.6196	Remote Similarity	NPC24960
0.6186	Remote Similarity	NPC128123
0.617	Remote Similarity	NPC181845
0.6162	Remote Similarity	NPC215408
0.6147	Remote Similarity	NPC83137
0.6132	Remote Similarity	NPC475319
0.6111	Remote Similarity	NPC232037
0.6095	Remote Similarity	NPC480555
0.6095	Remote Similarity	NPC150372
0.6055	Remote Similarity	NPC470864
0.6019	Remote Similarity	NPC473601
0.6019	Remote Similarity	NPC116756
0.587	Remote Similarity	NPC277715
0.581	Remote Similarity	NPC470433
0.581	Remote Similarity	NPC46190
0.581	Remote Similarity	NPC171073
0.5804	Remote Similarity	NPC480553
0.58	Remote Similarity	NPC306131
0.58	Remote Similarity	NPC200802
0.5789	Remote Similarity	NPC470866
0.5727	Remote Similarity	NPC475333
0.5727	Remote Similarity	NPC224098
0.5727	Remote Similarity	NPC208383
0.5701	Remote Similarity	NPC300557
0.5688	Remote Similarity	NPC115165
0.5676	Remote Similarity	NPC194207
0.5676	Remote Similarity	NPC22779
0.5664	Remote Similarity	NPC233433
0.5625	Remote Similarity	NPC480554
0.5579	Remote Similarity	NPC473774
0.5579	Remote Similarity	NPC481419
0.5579	Remote Similarity	NPC481417
0.5566	Remote Similarity	NPC202898
0.5556	Remote Similarity	NPC480556
0.5547	Remote Similarity	NPC481189
0.5534	Remote Similarity	NPC485601
0.5524	Remote Similarity	NPC14704
0.5514	Remote Similarity	NPC602423
0.5495	Remote Similarity	NPC269297
0.5495	Remote Similarity	NPC222202
0.5487	Remote Similarity	NPC108072
0.5462	Remote Similarity	NPC220836
0.5433	Remote Similarity	NPC329807
0.5431	Remote Similarity	NPC232054
0.5429	Remote Similarity	NPC70204
0.5364	Remote Similarity	NPC151134
0.536	Remote Similarity	NPC481190
0.5333	Remote Similarity	NPC470432
0.5333	Remote Similarity	NPC230507
0.5333	Remote Similarity	NPC477808
0.5321	Remote Similarity	NPC248746
0.531	Remote Similarity	NPC309278
0.5304	Remote Similarity	NPC476112
0.5304	Remote Similarity	NPC307534
0.5273	Remote Similarity	NPC274200
0.5273	Remote Similarity	NPC6806
0.5267	Remote Similarity	NPC329727
0.5263	Remote Similarity	NPC144790
0.5263	Remote Similarity	NPC149400
0.5258	Remote Similarity	NPC481420
0.5258	Remote Similarity	NPC481418
0.5258	Remote Similarity	NPC481421
0.5234	Remote Similarity	NPC305423
0.5233	Remote Similarity	NPC248944
0.5233	Remote Similarity	NPC7479
0.5233	Remote Similarity	NPC257296
0.5221	Remote Similarity	NPC475550
0.521	Remote Similarity	NPC94086
0.521	Remote Similarity	NPC473817
0.5197	Remote Similarity	NPC330026
0.5196	Remote Similarity	NPC210157
0.5175	Remote Similarity	NPC473518
0.5175	Remote Similarity	NPC13193
0.5172	Remote Similarity	NPC470862
0.5135	Remote Similarity	NPC42171
0.513	Remote Similarity	NPC232611
0.5128	Remote Similarity	NPC477811
0.5124	Remote Similarity	NPC224314
0.5096	Remote Similarity	NPC121453
0.5051	Remote Similarity	NPC172838
0.5051	Remote Similarity	NPC485600
0.5043	Remote Similarity	NPC32361

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC516707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7644
0.1-0.2	1424
0.2-0.3	68
0.3-0.4	8
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7386	Intermediate Similarity	NPD8171	Phase 2
0.6263	Remote Similarity	NPD8170	Phase 2
0.5233	Remote Similarity	NPD6928	Phase 2
0.5155	Remote Similarity	NPD7991	Discontinued

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data