NPASS Compound

Natural Product: NPC133818

Natural Product ID	NPC133818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hederagenin 3-O-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Alpha-L-Arabinopyranoside
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449987
PubChem CID	44583921
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 161169 0 0 0 0 0 0 0 0999 V2000 1.7761 2.4266 2.2142 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4621 2.1911 0.8541 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8594 1.7316 1.1992 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5660 1.2804 -0.0582 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5754 0.5736 -0.9497 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4386 0.1003 -0.1102 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6894 1.2594 0.2103 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6456 -0.8723 -0.6617 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 -1.9618 0.1221 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1133 -3.2483 -0.4232 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8291 -4.3911 0.5456 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4870 -4.3543 1.1757 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2410 -3.0742 1.6820 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1114 -2.2602 0.4903 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7697 -1.2441 0.6568 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9788 -1.4307 -0.0071 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0921 -1.4627 1.0196 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6023 -0.0702 1.3408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2900 0.5574 0.1326 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9373 2.0128 0.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7590 -0.1874 -1.0534 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3757 0.3167 -2.3032 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8605 0.0652 -2.3033 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5499 0.4452 -1.0302 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0372 1.8744 -1.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7511 0.2585 0.2236 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4485 0.9206 1.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8942 0.5285 1.3620 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4995 -0.0827 0.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9316 -0.4660 0.3746 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6299 -0.5203 1.6654 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8808 0.2968 1.8189 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8142 -0.4917 2.7627 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6487 1.6157 2.5471 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6360 0.5169 0.5612 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0899 -0.2099 -0.6390 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6210 0.2160 -0.7582 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0590 -0.3646 -2.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 -0.4379 -2.1413 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7666 -0.4533 -0.9155 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3373 -1.9027 -0.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5229 1.6707 -0.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9700 2.4368 -0.0345 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1427 2.2801 -1.9378 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2668 -0.3966 -1.0847 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4194 0.8115 -1.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9928 -1.0205 -2.4661 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6777 -1.4516 -2.5803 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7918 -4.3436 1.5673 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4924 -3.2039 -0.5637 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2680 -0.4597 -1.6072 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5018 0.3048 0.3290 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8098 0.6732 0.0922 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6433 0.6143 1.3398 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9605 1.3006 1.0754 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5548 0.7024 -0.1840 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5644 0.6558 -1.3046 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1453 -0.0526 -2.4907 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1694 -0.1344 -3.4866 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4503 -0.1195 -0.8761 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7310 1.3110 -0.5309 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8268 0.4728 -0.5348 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6956 0.6499 -1.7433 C 0 0 1 0 0 0 0 0 0 0 0 0 14.1430 0.8868 -1.2953 C 0 0 2 0 0 0 0 0 0 0 0 0 14.4821 -0.2455 -0.3296 C 0 0 1 0 0 0 0 0 0 0 0 0 13.5620 -0.1068 0.8537 C 0 0 1 0 0 0 0 0 0 0 0 0 14.3496 0.2803 2.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5837 0.4181 3.2008 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6046 0.8861 0.6051 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1687 -1.4234 -1.0334 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2039 2.1083 -0.6201 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7021 -0.4531 -2.5881 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8208 0.9851 2.1440 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0141 1.1548 2.4606 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5451 2.8371 1.7574 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0599 1.5624 2.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6942 2.3519 2.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1284 3.3516 2.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4553 3.2056 0.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7907 0.9517 1.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0819 2.1411 -0.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2311 1.2506 -1.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8498 -0.3183 0.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1278 -1.7581 1.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5719 -3.4797 -1.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9559 -5.3459 -0.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2871 -4.5134 0.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4588 -5.1249 1.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3361 -2.9456 -0.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9968 -2.4230 -0.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8842 -2.1793 0.8168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6168 -1.8169 1.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7182 0.5411 1.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2192 -0.1430 2.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9813 2.5044 -0.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6469 2.5826 0.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9573 2.1736 0.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1748 -1.2406 -0.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1025 1.3423 -2.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9888 -0.3292 -3.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0779 -0.9675 -2.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2735 0.7118 -3.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2602 2.3893 -0.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9048 1.9833 -1.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2179 2.5007 -1.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8058 -0.8535 0.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0728 0.4875 2.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3853 1.9818 1.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5228 0.7577 2.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8683 -1.5719 -0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0240 -0.3711 2.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9906 -1.6005 1.8177 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7855 0.0461 2.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3969 -0.4588 3.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9963 -1.5047 2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5852 1.9096 2.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2716 2.4377 2.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9720 1.5820 3.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6719 1.5984 0.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7223 0.2156 0.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6754 0.0444 -1.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0949 -1.2840 -0.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5171 -1.3978 -2.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4702 0.1796 -2.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3688 -1.4019 -2.7142 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2631 0.3331 -2.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4208 -2.1720 0.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3673 -2.1596 -1.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0791 -2.5698 -1.1674 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8028 3.1969 -2.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4668 0.6221 -1.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0053 0.9799 0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8377 1.7048 -1.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6691 -1.8281 -2.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0431 -0.1330 -3.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3547 -1.4212 -3.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4093 -3.7270 2.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8875 -3.3083 0.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9537 -0.0157 -2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7848 1.7200 -0.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8775 -0.4681 1.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8724 2.4008 1.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7975 -0.3740 0.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1849 1.6423 -1.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4701 -1.0763 -2.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0347 0.5046 -2.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0341 0.7295 -3.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6141 -0.5829 -0.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3430 1.5426 -2.3390 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7995 0.9284 -2.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5511 -0.2051 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9926 -1.0439 1.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8207 1.2815 1.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2121 -0.4276 2.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6303 0.2903 2.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9623 -1.9706 -1.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7564 2.7709 -1.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9846 -0.1133 -3.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9453 0.0022 2.2133 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4310 0.4539 2.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1512 3.0069 2.6401 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 6 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 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 1 37 42 1 6 42 43 2 0 42 44 1 0 21 45 1 0 45 46 1 1 45 47 1 0 47 48 1 0 11 49 1 0 10 50 1 0 5 51 1 0 4 52 1 0 52 53 1 0 53 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 56 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 66 69 1 0 65 70 1 0 64 71 1 0 63 72 1 0 55 73 1 0 54 74 1 0 3 75 1 0 7 2 1 0 14 9 1 0 45 16 1 0 60 53 1 0 69 62 1 0 26 19 1 0 40 29 1 0 40 24 1 0 37 30 1 0 1 76 1 0 1 77 1 0 1 78 1 0 2 79 1 6 3 80 1 1 4 81 1 6 5 82 1 6 6 83 1 1 9 84 1 1 10 85 1 6 11 86 1 6 12 87 1 0 12 88 1 0 14 89 1 6 16 90 1 6 17 91 1 0 17 92 1 0 18 93 1 0 18 94 1 0 20 95 1 0 20 96 1 0 20 97 1 0 21 98 1 1 22 99 1 0 22100 1 0 23101 1 0 23102 1 0 25103 1 0 25104 1 0 25105 1 0 26106 1 1 27107 1 0 27108 1 0 28109 1 0 30110 1 6 31111 1 0 31112 1 0 33113 1 0 33114 1 0 33115 1 0 34116 1 0 34117 1 0 34118 1 0 35119 1 0 35120 1 0 36121 1 0 36122 1 0 38123 1 0 38124 1 0 39125 1 0 39126 1 0 41127 1 0 41128 1 0 41129 1 0 44130 1 0 46131 1 0 46132 1 0 46133 1 0 47134 1 0 47135 1 0 48136 1 0 49137 1 0 50138 1 0 51139 1 0 53140 1 6 54141 1 1 55142 1 6 56143 1 1 57144 1 6 58145 1 0 58146 1 0 59147 1 0 62148 1 1 63149 1 6 64150 1 6 65151 1 1 66152 1 1 67153 1 0 67154 1 0 68155 1 0 70156 1 0 71157 1 0 72158 1 0 73159 1 0 74160 1 0 75161 1 0 M END

Standard InCHIKey	KPDVIKCSTOVVEA-LFGXWGNTSA-N
Standard InCHI	InChI=1S/C53H86O22/c1-23-32(58)41(74-44-38(64)36(62)40(28(20-55)71-44)73-43-37(63)35(61)34(60)27(19-54)70-43)39(65)45(69-23)75-42-33(59)26(57)21-68-46(42)72-31-11-12-49(4)29(50(31,5)22-56)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,47(66)67)17-15-51(24,52)6/h8,23,25-46,54-65H,9-22H2,1-7H3,(H,66,67)/t23-,25+,26-,27+,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,40+,41+,42+,43-,44-,45-,46-,49-,50-,51+,52+,53-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)[C@]1(C)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[15473660]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730260]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24360605]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	1

Activity Type	# Activity
Cell line	1

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[20122767]

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 NPC133818 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	24230
0.1-0.2	21617
0.2-0.3	2591
0.3-0.4	909
0.4-0.5	365
0.5-0.6	77
0.6-0.7	40
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9327	High Similarity	NPC251263
0.92	High Similarity	NPC276093
0.8739	High Similarity	NPC471385
0.8558	High Similarity	NPC324875
0.8558	High Similarity	NPC292677
0.8288	Intermediate Similarity	NPC54636
0.8246	Intermediate Similarity	NPC161717
0.82	Intermediate Similarity	NPC59804
0.8108	Intermediate Similarity	NPC219180
0.8018	Intermediate Similarity	NPC323341
0.7843	Intermediate Similarity	NPC174679
0.7843	Intermediate Similarity	NPC279554
0.7596	Intermediate Similarity	NPC127056
0.7593	Intermediate Similarity	NPC481082
0.7593	Intermediate Similarity	NPC164419
0.7478	Intermediate Similarity	NPC166422
0.7411	Intermediate Similarity	NPC475486
0.7379	Intermediate Similarity	NPC270667
0.7339	Intermediate Similarity	NPC139044
0.717	Intermediate Similarity	NPC56713
0.7075	Intermediate Similarity	NPC12288
0.7	Intermediate Similarity	NPC114304
0.6923	Remote Similarity	NPC475287
0.687	Remote Similarity	NPC488564
0.6832	Remote Similarity	NPC204407
0.6814	Remote Similarity	NPC257468
0.6814	Remote Similarity	NPC475504
0.68	Remote Similarity	NPC298034
0.68	Remote Similarity	NPC71065
0.6759	Remote Similarity	NPC136877
0.6726	Remote Similarity	NPC471383
0.6638	Remote Similarity	NPC323359
0.6609	Remote Similarity	NPC79718
0.6574	Remote Similarity	NPC164194
0.6545	Remote Similarity	NPC25605
0.6518	Remote Similarity	NPC80843
0.6491	Remote Similarity	NPC180550
0.6491	Remote Similarity	NPC35405
0.6486	Remote Similarity	NPC109079
0.6457	Remote Similarity	NPC202828
0.6457	Remote Similarity	NPC119592
0.6429	Remote Similarity	NPC41061
0.6429	Remote Similarity	NPC227551
0.6429	Remote Similarity	NPC488561
0.6393	Remote Similarity	NPC471384
0.6372	Remote Similarity	NPC22956
0.6328	Remote Similarity	NPC305981
0.6303	Remote Similarity	NPC488209
0.6293	Remote Similarity	NPC91838
0.6286	Remote Similarity	NPC28198
0.6286	Remote Similarity	NPC476123
0.6286	Remote Similarity	NPC606107
0.6283	Remote Similarity	NPC472949
0.6281	Remote Similarity	NPC476992
0.6279	Remote Similarity	NPC261506
0.6279	Remote Similarity	NPC4328
0.625	Remote Similarity	NPC293330
0.625	Remote Similarity	NPC65105
0.6207	Remote Similarity	NPC104400
0.6207	Remote Similarity	NPC10320
0.6066	Remote Similarity	NPC62725
0.6061	Remote Similarity	NPC220160
0.5968	Remote Similarity	NPC76972
0.5968	Remote Similarity	NPC469782
0.5968	Remote Similarity	NPC204414
0.5954	Remote Similarity	NPC236638
0.5954	Remote Similarity	NPC294453
0.5902	Remote Similarity	NPC187618
0.5856	Remote Similarity	NPC284807
0.5854	Remote Similarity	NPC481078
0.5846	Remote Similarity	NPC110633
0.5833	Remote Similarity	NPC275668
0.5794	Remote Similarity	NPC79643
0.5785	Remote Similarity	NPC119794
0.5778	Remote Similarity	NPC250247
0.5776	Remote Similarity	NPC114441
0.5763	Remote Similarity	NPC469945
0.576	Remote Similarity	NPC288205
0.576	Remote Similarity	NPC51465
0.5758	Remote Similarity	NPC43550
0.5703	Remote Similarity	NPC135904
0.5688	Remote Similarity	NPC283849
0.568	Remote Similarity	NPC280941
0.568	Remote Similarity	NPC235772
0.5597	Remote Similarity	NPC136768
0.5593	Remote Similarity	NPC6377
0.5593	Remote Similarity	NPC208381
0.5591	Remote Similarity	NPC313110
0.5581	Remote Similarity	NPC123199
0.5573	Remote Similarity	NPC481080
0.5556	Remote Similarity	NPC40085
0.5545	Remote Similarity	NPC57362
0.5536	Remote Similarity	NPC100383
0.5489	Remote Similarity	NPC473452
0.5469	Remote Similarity	NPC60557
0.5469	Remote Similarity	NPC67857
0.544	Remote Similarity	NPC218954
0.5439	Remote Similarity	NPC473538
0.542	Remote Similarity	NPC100639
0.541	Remote Similarity	NPC473383
0.5403	Remote Similarity	NPC488515
0.538	Remote Similarity	NPC469777
0.5374	Remote Similarity	NPC264270
0.5372	Remote Similarity	NPC112352
0.5368	Remote Similarity	NPC111466
0.5366	Remote Similarity	NPC258885
0.5359	Remote Similarity	NPC469775
0.5355	Remote Similarity	NPC469774
0.5338	Remote Similarity	NPC488211
0.5323	Remote Similarity	NPC73829
0.5312	Remote Similarity	NPC480939
0.531	Remote Similarity	NPC31839
0.5299	Remote Similarity	NPC57484
0.528	Remote Similarity	NPC469772
0.5259	Remote Similarity	NPC191410
0.5255	Remote Similarity	NPC481081
0.5253	Remote Similarity	NPC100925
0.5227	Remote Similarity	NPC155410
0.5221	Remote Similarity	NPC258617
0.5215	Remote Similarity	NPC469773
0.5188	Remote Similarity	NPC471550
0.5185	Remote Similarity	NPC21691
0.5167	Remote Similarity	NPC475296
0.5156	Remote Similarity	NPC241909
0.5154	Remote Similarity	NPC475119
0.5149	Remote Similarity	NPC47995
0.5143	Remote Similarity	NPC488212
0.5108	Remote Similarity	NPC302543
0.5088	Remote Similarity	NPC177246
0.5075	Remote Similarity	NPC191827
0.5074	Remote Similarity	NPC476068
0.5043	Remote Similarity	NPC286347
0.5043	Remote Similarity	NPC475633
0.5039	Remote Similarity	NPC486563
0.5038	Remote Similarity	NPC165204
0.5036	Remote Similarity	NPC286457
0.5036	Remote Similarity	NPC476774
0.5036	Remote Similarity	NPC476780
0.5031	Remote Similarity	NPC469778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC133818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7077
0.1-0.2	2004
0.2-0.3	61
0.3-0.4	8
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