NPASS Compound

Natural Product: NPC256133

Natural Product ID	NPC256133
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nephelioside Iv
IUPAC Name	(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6R,6aR,6bR,8aS,12aS,14aR,14bS)-8a-(hydroxymethyl)-6-methoxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms	nephelioside IV
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448391
PubChem CID	21575018
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 145152 0 0 0 0 0 0 0 0999 V2000 -4.9625 2.2893 -4.7575 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9690 1.9107 -3.8460 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4805 0.7801 -2.9655 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3670 1.2403 -2.2829 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7699 0.1992 -1.5287 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7093 0.7841 -0.8831 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4565 0.2646 -1.2460 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7087 1.3244 -1.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7937 1.2961 -1.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2496 1.0909 -0.3610 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6608 -0.2015 0.0215 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8352 -0.3054 -0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1455 -1.8041 -0.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5111 0.2098 1.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2283 -0.8380 1.2231 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7456 -1.0714 0.9004 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3687 0.3314 0.7830 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7509 0.8723 -0.4556 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4733 1.9399 -1.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8842 1.4881 -1.3307 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5230 0.7647 -0.4545 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8404 0.3396 0.7794 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3392 -0.9322 1.4108 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4690 1.3865 1.7645 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9642 1.1390 1.8190 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6902 0.9864 0.5489 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9572 0.4493 -0.6421 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2678 -0.9335 -1.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6440 -1.4457 -0.8716 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7619 -2.6118 0.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2764 -1.9853 -2.1782 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5517 -0.3060 -0.4714 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9689 0.2065 0.8361 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2220 2.3913 0.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0613 2.8216 1.1908 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9826 1.0607 2.0509 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6349 -1.6449 -0.3496 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8160 -2.9727 -0.4880 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8190 2.3242 0.3223 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7923 -0.2189 -0.4990 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0659 0.6141 -0.6075 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5790 0.3907 -2.0193 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9166 -0.9181 -2.2533 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7588 1.9387 -0.4314 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4287 2.5555 0.6149 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2461 3.5931 0.1636 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9316 4.8271 0.6792 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1117 4.8589 2.1986 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1420 3.8391 2.7431 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4494 3.0537 1.6473 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7823 2.0133 2.2771 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1448 4.5294 3.4390 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8744 6.1444 2.6412 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1951 -1.5643 -0.6631 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0264 -2.2368 0.5243 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1093 -3.2710 0.4002 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6927 -4.5007 0.2236 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6932 -5.3954 -0.5046 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5270 -5.5205 0.2620 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9389 -4.4250 -0.6340 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0037 -3.7332 0.2034 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3479 -2.7245 1.0859 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0423 -3.3017 2.3370 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0445 -3.2477 -0.5543 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3171 -5.7286 -0.9248 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1382 2.5520 -4.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8791 1.6605 -4.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1778 2.8207 -3.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1641 -0.0545 -3.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4932 -0.6147 -2.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7019 -0.5350 -2.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1049 2.3391 -1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9198 1.3014 -3.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2602 0.5581 -2.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0945 2.3556 -2.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9753 -0.8933 -0.8405 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4617 -2.1879 0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 -2.0337 -0.7566 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2487 -2.3882 -0.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3184 -0.4908 1.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0403 1.1724 1.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 0.2590 2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0494 -0.4524 2.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8738 -1.9262 1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0705 -1.6711 1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8091 0.0041 -1.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0489 1.9851 -2.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3938 2.9452 -0.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3992 1.8096 -2.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9700 -1.8625 1.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4215 -1.0000 1.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9838 -0.8602 2.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1290 1.2555 2.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3160 2.3998 1.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2431 0.3940 2.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3301 2.0896 2.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3379 1.0699 -1.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5137 -1.7116 -0.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1034 -1.0478 -2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5473 -3.5591 -0.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8243 -2.6945 0.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0551 -2.6014 0.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3625 -2.0263 -2.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9465 -1.3375 -2.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8174 -2.9890 -2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5449 -0.7292 -0.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5752 0.4397 -1.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7085 0.8189 1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7647 -0.6804 1.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8388 2.2668 -0.7400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3592 3.0802 0.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3581 3.7327 0.9482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.4030 2.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4550 2.0852 2.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9339 1.2336 2.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0880 -3.5780 0.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8154 -3.2992 -0.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7020 -3.3294 -1.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1032 2.2307 1.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7466 2.9178 0.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3029 3.0845 -0.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4409 -0.0589 0.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7913 0.2251 0.1178 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4595 1.0375 -2.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2093 -1.3734 -2.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0780 1.7958 1.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6651 5.5479 0.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9149 5.1418 0.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1472 4.5628 2.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6248 3.1425 3.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6780 3.6977 1.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1902 1.7373 3.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2368 5.4945 3.4121 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7657 6.6138 2.7179 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6139 -1.5401 1.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9055 -4.9903 1.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5052 -4.9537 -1.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1854 -6.3822 -0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -6.4680 0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7336 -3.8139 -1.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4241 -4.5267 0.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9665 -1.8443 1.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6225 -2.5914 2.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1877 -3.8027 -1.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2616 -5.7723 -1.2192 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 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 11 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 2 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 26 34 1 6 34 35 1 0 17 36 1 1 16 37 1 0 37 38 1 0 10 39 1 1 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 40 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 61 64 1 0 60 65 1 0 42 3 1 0 50 45 1 0 62 55 1 0 12 7 1 0 22 17 1 0 33 26 1 0 18 10 1 0 27 21 1 0 1 66 1 0 2 67 1 0 2 68 1 0 3 69 1 6 5 70 1 6 7 71 1 6 8 72 1 0 8 73 1 0 9 74 1 0 9 75 1 0 11 76 1 6 13 77 1 0 13 78 1 0 13 79 1 0 14 80 1 0 14 81 1 0 14 82 1 0 15 83 1 0 15 84 1 0 16 85 1 1 18 86 1 6 19 87 1 0 19 88 1 0 20 89 1 0 23 90 1 0 23 91 1 0 23 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 27 97 1 6 28 98 1 0 28 99 1 0 30100 1 0 30101 1 0 30102 1 0 31103 1 0 31104 1 0 31105 1 0 32106 1 0 32107 1 0 33108 1 0 33109 1 0 34110 1 0 34111 1 0 35112 1 0 36113 1 0 36114 1 0 36115 1 0 38116 1 0 38117 1 0 38118 1 0 39119 1 0 39120 1 0 39121 1 0 40122 1 1 41123 1 1 42124 1 6 43125 1 0 45126 1 1 47127 1 0 47128 1 0 48129 1 6 49130 1 1 50131 1 6 51132 1 0 52133 1 0 53134 1 0 55135 1 1 57136 1 1 58137 1 0 58138 1 0 59139 1 0 60140 1 6 61141 1 1 62142 1 1 63143 1 0 64144 1 0 65145 1 0 M END

Standard InCHIKey	PSMYLMVERYGQNX-VVDIZRGUSA-N
Standard InCHI	InChI=1S/C48H80O17/c1-43(2)13-15-48(22-51)16-14-46(6)23(24(48)18-43)9-10-28-45(5)12-11-30(44(3,4)29(45)17-31(59-8)47(28,46)7)63-42-39(65-41-37(58)35(56)33(54)26(19-49)61-41)38(34(55)27(20-50)62-42)64-40-36(57)32(53)25(52)21-60-40/h9,24-42,49-58H,10-22H2,1-8H3/t24-,25-,26+,27+,28+,29-,30-,31+,32-,33+,34+,35-,36+,37+,38-,39+,40-,41-,42-,45+,46+,47-,48+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)C[C@H]([C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)CO)C)OC)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	928.54	Volume:	917.109 ? Van der Waals volume.
Dense:	1.012	LogP:	1.131 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.923 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.746 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	44.0
TPSA:	266.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.108	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.449	Fsp³:	0.958
MCE-18:	170.17 ? 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:	0.868	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.239	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.024	MDCK Permeability:	-5.266
Pgp-inhibitor:	0.0	Pgp-substrate:	0.48
PAMPA:	1.0 ? 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):	0.06
20% Bioavailability (F20%):	0.899	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987	MRP1:	0.023
Plasma Protein Binding (PPB):	70.992%	Volume Distribution (VD):	-0.482
Fu:	20.076% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.047
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.026	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.907
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.039
HLM stability:	0.231 ? 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):

0.126

Half-life (T1/2):

2.658

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.704	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.956	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.302	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.998
Hematotoxicity:	0.815	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.114	RPMI-8226 Immunitoxicity:	0.205
A549 Cytotoxicity:	0.967	Hek293 Cytotoxicity:	0.748
BCF:	1.945 ? 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:	3.752 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.447 ? 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
NPO19602	Nephelium maingayi	Species	Sapindaceae	Eukaryota	bark	n.a.	n.a.	PMID[14987059]
NPO19602	Nephelium maingayi	Species	Sapindaceae	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

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell line	4

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
NPT1034	Cell line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[7807120]
NPT858	Cell line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[7807120]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[7807120]
NPT737	Cell line	HUVEC	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[7807120]

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 NPC256133 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	21418
0.1-0.2	24198
0.2-0.3	3048
0.3-0.4	792
0.4-0.5	357
0.5-0.6	34
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8191	Intermediate Similarity	NPC213674
0.71	Intermediate Similarity	NPC263756
0.6961	Remote Similarity	NPC30289
0.6389	Remote Similarity	NPC79718
0.6019	Remote Similarity	NPC117714
0.5877	Remote Similarity	NPC187290
0.5818	Remote Similarity	NPC10607
0.5688	Remote Similarity	NPC469946
0.5648	Remote Similarity	NPC109079
0.5536	Remote Similarity	NPC2370
0.5517	Remote Similarity	NPC80986
0.5439	Remote Similarity	NPC297263
0.5421	Remote Similarity	NPC1046
0.5398	Remote Similarity	NPC46665
0.5354	Remote Similarity	NPC481081
0.5351	Remote Similarity	NPC475591
0.5351	Remote Similarity	NPC236870
0.5339	Remote Similarity	NPC104137
0.5339	Remote Similarity	NPC26626
0.5339	Remote Similarity	NPC481078
0.5312	Remote Similarity	NPC302543
0.5299	Remote Similarity	NPC606145
0.5285	Remote Similarity	NPC283417
0.5285	Remote Similarity	NPC200049
0.528	Remote Similarity	NPC57484
0.5221	Remote Similarity	NPC112352
0.5217	Remote Similarity	NPC63159
0.5185	Remote Similarity	NPC90856
0.5169	Remote Similarity	NPC301449
0.5169	Remote Similarity	NPC481079
0.5169	Remote Similarity	NPC601290
0.5083	Remote Similarity	NPC31838
0.5082	Remote Similarity	NPC475287
0.5082	Remote Similarity	NPC610204
0.5081	Remote Similarity	NPC123199
0.5078	Remote Similarity	NPC470876
0.5044	Remote Similarity	NPC295371
0.5043	Remote Similarity	NPC480947
0.5041	Remote Similarity	NPC123522

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC256133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7184
0.1-0.2	1904
0.2-0.3	58
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

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