NPASS Compound

Natural Product: NPC469946

Natural Product ID	NPC469946
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosyl(1->2)-Beta-D-Glucopyranosyl-28-O-Beta-D-Glucopyranosyl Oleanolic Acid
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1288839
PubChem CID	52949436
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 140147 0 0 0 0 0 0 0 0999 V2000 -6.8458 1.2128 -5.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8319 1.8061 -4.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7136 1.2393 -2.8168 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4499 1.5207 -2.3028 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2326 0.8268 -1.0984 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9644 1.1607 -0.6150 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0566 0.0942 -0.7197 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0279 0.4375 -1.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1562 1.5774 -1.3595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3036 1.1744 -0.1546 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8496 -0.1120 0.3645 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3286 -0.2147 0.5455 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5915 -1.7116 0.8167 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8622 0.5049 1.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 -0.5690 1.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3116 -1.0060 0.9865 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9421 0.0641 0.1846 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0503 0.8176 -0.7303 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7666 1.9064 -1.4304 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2288 1.6644 -1.4359 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8570 0.5578 -1.1287 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0047 -0.6016 -0.7244 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3216 -1.2890 -1.8796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8173 -1.6034 -0.0103 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9669 -2.0308 -0.8712 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9221 -0.8835 -1.0506 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3647 0.4702 -1.1587 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8278 1.2819 -2.3469 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2489 1.0929 -2.7414 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3249 1.4486 -4.2386 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1342 2.1433 -2.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7974 -0.2834 -2.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7109 -1.2556 -2.3316 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9297 -1.0203 0.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9420 -2.0020 0.8523 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9086 -0.0606 0.2846 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8721 -0.1464 1.2964 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7106 0.8304 2.3062 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3327 0.2975 3.4359 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0288 1.0289 4.7045 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7315 0.3638 5.7335 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7994 0.0852 3.2055 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2032 0.4860 1.7950 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2795 -0.1510 0.7725 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7589 -1.4343 0.5228 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1649 1.8666 1.6601 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1792 -1.2575 3.3697 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 0.9680 1.1380 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.3154 0.7795 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3419 1.0129 -0.1292 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1394 2.2266 -0.5680 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7274 1.9164 -1.9315 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8564 1.1070 -1.7683 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2255 3.2666 -0.7491 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1019 -0.1242 -0.0601 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1561 -0.7044 1.2037 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4849 -0.6030 1.6090 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8653 -1.4921 2.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7584 -2.0554 3.4114 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6328 -2.6198 2.5941 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7755 -2.1459 1.1632 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8022 -2.8638 0.5616 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4136 -2.1268 3.1102 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2964 -3.1307 4.1542 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7740 0.2483 -4.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7385 2.9103 -4.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8053 1.4828 -4.6599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9069 0.1422 -2.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1853 -0.2372 -1.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6186 -0.7537 -1.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 -0.4316 -2.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6541 0.8480 -2.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8282 2.4197 -1.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5418 1.8896 -2.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6232 -0.8834 -0.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4747 -2.0677 0.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7464 -2.3415 0.4444 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 -1.9017 1.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1189 0.7704 2.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4617 1.3815 1.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6429 -0.1111 2.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5474 -1.3818 2.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8224 0.2299 2.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1472 -1.9560 0.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9742 -1.2189 1.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2473 0.1106 -1.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4793 2.0107 -2.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5994 2.9191 -1.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8448 2.5323 -1.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3444 -1.7602 -1.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8513 -2.1754 -2.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1839 -0.6353 -2.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2431 -1.2776 0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1790 -2.4896 0.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6987 -2.3731 -1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5112 -2.8518 -0.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7730 1.0509 -0.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7529 2.3686 -2.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1599 1.1067 -3.2263 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9178 0.5873 -4.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8287 2.3968 -4.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3971 1.5399 -4.4742 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7890 2.3479 -1.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1113 3.0947 -2.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1801 1.7793 -1.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6466 -0.3319 -1.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2955 -0.6356 -3.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0292 -1.2747 -3.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1348 -2.2659 -2.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6974 -1.1066 1.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8836 -0.7336 3.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9578 0.8741 4.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3379 2.0872 4.6806 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2246 -0.4212 5.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4078 0.6646 3.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2324 0.0900 1.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3837 0.4133 -0.1772 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1758 -1.9747 -0.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8689 2.0696 0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8775 -1.5194 2.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4502 0.7398 2.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7922 0.8409 1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4851 2.0301 1.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7965 2.1887 1.7237 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9881 3.2267 0.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3872 2.5272 1.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9094 1.2025 0.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8881 2.5573 0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0551 2.8465 -2.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3448 1.1287 -2.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5934 3.2289 0.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5562 -0.1180 1.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4320 -2.3492 2.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5999 -1.0406 3.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4142 -1.3182 4.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5937 -3.7120 2.6257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8126 -2.3367 0.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7459 -3.7981 0.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5712 -1.6099 3.9477 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2260 -3.3138 3.9051 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 6 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 1 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 17 48 1 1 10 49 1 1 5 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 59 64 1 0 52 3 1 0 61 56 1 0 12 7 1 0 22 17 1 0 33 26 1 0 44 37 1 0 18 10 1 0 27 21 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 6 5 69 1 6 7 70 1 6 8 71 1 0 8 72 1 0 9 73 1 0 9 74 1 0 11 75 1 6 13 76 1 0 13 77 1 0 13 78 1 0 14 79 1 0 14 80 1 0 14 81 1 0 15 82 1 0 15 83 1 0 16 84 1 0 16 85 1 0 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 1 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 37110 1 1 39111 1 1 40112 1 0 40113 1 0 41114 1 0 42115 1 1 43116 1 6 44117 1 6 45118 1 0 46119 1 0 47120 1 0 48121 1 0 48122 1 0 48123 1 0 49124 1 0 49125 1 0 49126 1 0 50127 1 1 51128 1 1 52129 1 6 53130 1 0 54131 1 0 56132 1 1 58133 1 0 58134 1 0 59135 1 1 60136 1 6 61137 1 6 62138 1 0 63139 1 0 64140 1 0 M END

Standard InCHIKey	QZLPNDOKXHEYFW-MOIUONMWSA-N
Standard InCHI	InChI=1S/C47H76O17/c1-42(2)14-16-47(41(58)64-39-36(57)33(54)31(52)25(19-48)60-39)17-15-45(6)22(23(47)18-42)8-9-28-44(5)12-11-29(43(3,4)27(44)10-13-46(28,45)7)62-40-37(34(55)32(53)26(20-49)61-40)63-38-35(56)30(51)24(50)21-59-38/h8,23-40,48-57H,9-21H2,1-7H3/t23-,24+,25+,26+,27-,28+,29-,30-,31+,32+,33-,34-,35+,36+,37+,38+,39-,40-,44-,45+,46+,47-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@H]1OC[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	912.51	Volume:	897.177 ? Van der Waals volume.
Dense:	1.017	LogP:	1.804 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.502 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.203 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	45.0
TPSA:	274.75 ? 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:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.198	Fsp³:	0.936
MCE-18:	171.692 ? 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:	0.917	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.185	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.144	MDCK Permeability:	-5.129
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
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):	0.256
20% Bioavailability (F20%):	0.409	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019	MRP1:	0.025
Plasma Protein Binding (PPB):	73.049%	Volume Distribution (VD):	-0.417
Fu:	17.288% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.246	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.142	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.612 ? 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):

-0.119

Half-life (T1/2):

3.485

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.806	Drug-induced Liver Injury (DILI):	0.904
AMES Toxicity:	0.893	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.092	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.52	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.326	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.48	Hek293 Cytotoxicity:	0.186
BCF:	1.661 ? 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:	3.757 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.3 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.474 ? 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
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951582]
NPO1994	Panax stipuleanatus	Species	Araliaceae	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
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[2342056]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	75940.0	nM	PMID[15270558]

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 NPC469946 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	22255
0.1-0.2	22881
0.2-0.3	3231
0.3-0.4	763
0.4-0.5	374
0.5-0.6	68
0.6-0.7	95
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9022	High Similarity	NPC297263
0.8557	High Similarity	NPC31838
0.8351	Intermediate Similarity	NPC301449
0.8351	Intermediate Similarity	NPC601290
0.8191	Intermediate Similarity	NPC112352
0.8182	Intermediate Similarity	NPC481078
0.8125	Intermediate Similarity	NPC63159
0.8021	Intermediate Similarity	NPC480475
0.798	Intermediate Similarity	NPC481079
0.7912	Intermediate Similarity	NPC90856
0.7857	Intermediate Similarity	NPC222580
0.7742	Intermediate Similarity	NPC48499
0.7714	Intermediate Similarity	NPC123199
0.7653	Intermediate Similarity	NPC251768
0.7647	Intermediate Similarity	NPC187290
0.7604	Intermediate Similarity	NPC295371
0.7449	Intermediate Similarity	NPC192791
0.7396	Intermediate Similarity	NPC475516
0.7358	Intermediate Similarity	NPC79643
0.734	Intermediate Similarity	NPC214484
0.7273	Intermediate Similarity	NPC57484
0.7222	Intermediate Similarity	NPC135904
0.7204	Intermediate Similarity	NPC128925
0.7158	Intermediate Similarity	NPC204458
0.7129	Intermediate Similarity	NPC46665
0.7083	Intermediate Similarity	NPC78046
0.7071	Intermediate Similarity	NPC39211
0.7059	Intermediate Similarity	NPC475591
0.7059	Intermediate Similarity	NPC236870
0.7048	Intermediate Similarity	NPC295823
0.7048	Intermediate Similarity	NPC174720
0.7048	Intermediate Similarity	NPC480473
0.7048	Intermediate Similarity	NPC475467
0.7048	Intermediate Similarity	NPC480474
0.7041	Intermediate Similarity	NPC235405
0.7	Intermediate Similarity	NPC213674
0.697	Remote Similarity	NPC249848
0.697	Remote Similarity	NPC107966
0.6961	Remote Similarity	NPC10607
0.6944	Remote Similarity	NPC60557
0.6944	Remote Similarity	NPC67857
0.6931	Remote Similarity	NPC223301
0.6931	Remote Similarity	NPC171544
0.6923	Remote Similarity	NPC250247
0.6907	Remote Similarity	NPC1046
0.69	Remote Similarity	NPC157868
0.6897	Remote Similarity	NPC70809
0.6875	Remote Similarity	NPC481080
0.687	Remote Similarity	NPC481081
0.6863	Remote Similarity	NPC30735
0.6847	Remote Similarity	NPC470218
0.6842	Remote Similarity	NPC41061
0.6842	Remote Similarity	NPC227551
0.6832	Remote Similarity	NPC263756
0.6813	Remote Similarity	NPC167383
0.6733	Remote Similarity	NPC488561
0.6731	Remote Similarity	NPC235438
0.6729	Remote Similarity	NPC80986
0.6724	Remote Similarity	NPC236638
0.6724	Remote Similarity	NPC294453
0.6724	Remote Similarity	NPC305981
0.6699	Remote Similarity	NPC160415
0.6698	Remote Similarity	NPC104372
0.6696	Remote Similarity	NPC191827
0.6667	Remote Similarity	NPC261506
0.6667	Remote Similarity	NPC237503
0.6667	Remote Similarity	NPC4328
0.6636	Remote Similarity	NPC475287
0.6635	Remote Similarity	NPC40775
0.6635	Remote Similarity	NPC159309
0.6635	Remote Similarity	NPC86222
0.6577	Remote Similarity	NPC123522
0.6566	Remote Similarity	NPC29069
0.6552	Remote Similarity	NPC470876
0.6552	Remote Similarity	NPC258617
0.6549	Remote Similarity	NPC283417
0.6549	Remote Similarity	NPC200049
0.6535	Remote Similarity	NPC139894
0.6514	Remote Similarity	NPC104137
0.6514	Remote Similarity	NPC26626
0.6509	Remote Similarity	NPC475504
0.6496	Remote Similarity	NPC43550
0.6495	Remote Similarity	NPC256798
0.6491	Remote Similarity	NPC488560
0.6486	Remote Similarity	NPC610204
0.6476	Remote Similarity	NPC164389
0.6465	Remote Similarity	NPC189884
0.6465	Remote Similarity	NPC138334
0.6449	Remote Similarity	NPC64715
0.6422	Remote Similarity	NPC241909
0.6404	Remote Similarity	NPC475160
0.6404	Remote Similarity	NPC471550
0.6404	Remote Similarity	NPC473714
0.6389	Remote Similarity	NPC281148
0.6389	Remote Similarity	NPC114484
0.6381	Remote Similarity	NPC309714
0.6381	Remote Similarity	NPC30289
0.6339	Remote Similarity	NPC76972
0.6339	Remote Similarity	NPC469782
0.6339	Remote Similarity	NPC204414
0.6293	Remote Similarity	NPC4749
0.6263	Remote Similarity	NPC209894
0.625	Remote Similarity	NPC473884
0.6226	Remote Similarity	NPC117714
0.6216	Remote Similarity	NPC207738
0.6216	Remote Similarity	NPC609281
0.6195	Remote Similarity	NPC300419
0.6182	Remote Similarity	NPC606145
0.6167	Remote Similarity	NPC202828
0.6167	Remote Similarity	NPC119592
0.6161	Remote Similarity	NPC11242
0.6154	Remote Similarity	NPC473373
0.6154	Remote Similarity	NPC150400
0.6132	Remote Similarity	NPC242840
0.6116	Remote Similarity	NPC298034
0.6116	Remote Similarity	NPC71065
0.6106	Remote Similarity	NPC185466
0.6102	Remote Similarity	NPC476068
0.6083	Remote Similarity	NPC293330
0.6078	Remote Similarity	NPC164194
0.6071	Remote Similarity	NPC36831
0.6053	Remote Similarity	NPC268184
0.6053	Remote Similarity	NPC607904
0.6053	Remote Similarity	NPC610461
0.604	Remote Similarity	NPC161434
0.6034	Remote Similarity	NPC603137
0.6019	Remote Similarity	NPC488526
0.6017	Remote Similarity	NPC85154
0.6016	Remote Similarity	NPC224381
0.6	Remote Similarity	NPC58448
0.6	Remote Similarity	NPC302887
0.5983	Remote Similarity	NPC100639
0.5982	Remote Similarity	NPC160452
0.595	Remote Similarity	NPC65105
0.5948	Remote Similarity	NPC475899
0.5948	Remote Similarity	NPC165204
0.5918	Remote Similarity	NPC199457
0.5917	Remote Similarity	NPC286457
0.5906	Remote Similarity	NPC33012
0.5902	Remote Similarity	NPC136768
0.5888	Remote Similarity	NPC161674
0.5887	Remote Similarity	NPC482010
0.5877	Remote Similarity	NPC75287
0.5877	Remote Similarity	NPC606553
0.5872	Remote Similarity	NPC305267
0.5872	Remote Similarity	NPC473459
0.5872	Remote Similarity	NPC148603
0.5865	Remote Similarity	NPC179434
0.5859	Remote Similarity	NPC68419
0.5854	Remote Similarity	NPC302543
0.5849	Remote Similarity	NPC127056
0.5833	Remote Similarity	NPC21691
0.5833	Remote Similarity	NPC469945
0.5827	Remote Similarity	NPC8524
0.5826	Remote Similarity	NPC288205
0.5826	Remote Similarity	NPC51465
0.5818	Remote Similarity	NPC68175
0.5794	Remote Similarity	NPC470512
0.5785	Remote Similarity	NPC473645
0.5785	Remote Similarity	NPC110633
0.5778	Remote Similarity	NPC220838
0.576	Remote Similarity	NPC220160
0.5758	Remote Similarity	NPC306746
0.5755	Remote Similarity	NPC25605
0.5741	Remote Similarity	NPC473343
0.5714	Remote Similarity	NPC79718
0.5703	Remote Similarity	NPC480422
0.5702	Remote Similarity	NPC481030
0.5688	Remote Similarity	NPC75417
0.5688	Remote Similarity	NPC256133
0.5676	Remote Similarity	NPC148417
0.5664	Remote Similarity	NPC469778
0.5656	Remote Similarity	NPC480418
0.5641	Remote Similarity	NPC473824
0.5636	Remote Similarity	NPC480947
0.5636	Remote Similarity	NPC104071
0.5636	Remote Similarity	NPC114304
0.563	Remote Similarity	NPC155410
0.563	Remote Similarity	NPC480419
0.563	Remote Similarity	NPC609305
0.5625	Remote Similarity	NPC470514
0.5625	Remote Similarity	NPC489209
0.5625	Remote Similarity	NPC123796
0.5614	Remote Similarity	NPC291903
0.5603	Remote Similarity	NPC470915
0.5603	Remote Similarity	NPC815
0.5596	Remote Similarity	NPC80843
0.5588	Remote Similarity	NPC45606
0.5586	Remote Similarity	NPC102439
0.5586	Remote Similarity	NPC173859
0.5583	Remote Similarity	NPC475140
0.5577	Remote Similarity	NPC47063
0.5574	Remote Similarity	NPC484061
0.5574	Remote Similarity	NPC484062
0.5565	Remote Similarity	NPC470477
0.5565	Remote Similarity	NPC69811
0.5556	Remote Similarity	NPC472268
0.5556	Remote Similarity	NPC475119
0.5545	Remote Similarity	NPC604133

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7350
0.1-0.2	1743
0.2-0.3	51
0.3-0.4	6
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