NPASS Compound

Natural Product: NPC471547

Natural Product ID	NPC471547
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-O-Methyl 4A-O-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl] (2S,4Ar,6Ar,6As,6Br,8Ar,9R,10R,11S,12As,13R,14Bs)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-11,13-Dihydroxy-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-2,4A-Dicarboxylate
IUPAC Name	2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aS,13R,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11,13-dihydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL256132
PubChem CID	24770100
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 146153 0 0 0 0 0 0 0 0999 V2000 12.6347 -0.4875 2.0117 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8683 -1.1991 0.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5934 -1.2592 -0.0012 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2177 0.0558 -0.2743 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0560 0.0994 -1.0532 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5895 1.3998 -0.9614 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3279 1.4214 -0.4354 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2911 2.0855 -1.2954 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5404 3.0539 -0.5820 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8653 2.4340 0.4735 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8398 1.8119 1.4192 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2630 2.1179 0.9137 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2329 1.7316 1.7974 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7987 2.3971 2.7072 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9662 1.5691 -0.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6409 1.8600 0.1817 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9721 2.4219 -1.0155 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5079 2.0470 -2.2403 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4849 2.2282 -1.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0222 0.8501 -0.7715 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6079 0.4008 0.5422 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0157 0.6716 0.8222 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8377 -0.5939 0.5948 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1657 0.9040 2.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6530 -0.0831 3.1152 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2011 -1.0637 0.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2734 -1.2744 0.6808 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0845 -0.4039 -0.2132 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4770 0.9144 -0.5198 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2618 1.6527 -1.5336 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 3.0444 -1.4143 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7209 1.5458 -1.2745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 0.7515 -0.3886 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4582 -0.1311 0.4453 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2215 0.5352 1.7749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0737 -1.4830 0.6946 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4906 -1.6474 0.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3420 -0.3946 0.4833 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7694 0.7603 -0.2360 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3640 2.0430 0.1745 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8190 2.2248 1.5751 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0321 3.4183 2.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6116 1.1036 2.5210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6503 -0.2416 1.9241 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2695 2.6565 1.6288 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5710 3.7502 2.1400 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2850 1.8614 1.1212 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6376 2.3349 1.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6486 -0.7430 -0.2095 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1039 -0.0240 -1.1302 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3886 -1.8635 0.1456 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6135 -2.1858 -0.4882 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6622 -2.3006 0.3726 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8444 -2.5085 -0.2763 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.5362 -3.7697 0.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7623 -3.5943 1.6101 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7893 -2.5560 -1.7667 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6603 -3.4052 -2.2925 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5083 -3.4639 -1.3026 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2798 -3.5550 -1.9169 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1264 -4.6595 -2.6206 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8299 -1.2909 -2.3754 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3745 -1.1652 -1.5124 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3710 -0.0136 -1.9386 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4641 -0.3183 -2.4442 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8923 -1.7722 -2.3675 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8576 -2.0435 -1.2515 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7369 -3.4138 -0.9278 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4747 -2.1952 -3.5657 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3467 -0.2721 -3.2958 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1720 0.3661 1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2725 -2.1714 1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6098 -0.5617 0.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7978 -1.7052 0.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3125 -0.6630 -0.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9837 0.3671 -0.2334 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5604 1.3630 -1.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7965 2.5945 -2.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3496 3.2405 1.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8001 0.7337 1.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3315 3.1997 0.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6143 2.5505 2.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5756 3.3598 2.6571 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7155 2.7226 0.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0903 3.5561 -1.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2202 2.6540 -2.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1483 2.5160 -2.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0213 2.9415 -0.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9977 0.9339 1.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8906 -0.2426 0.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8140 -1.2592 1.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6220 -1.1150 -0.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6804 1.9072 2.5062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2373 1.0748 2.5589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3827 -0.4947 3.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7053 -1.7036 -0.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6114 -1.4173 1.6464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6202 -1.2936 1.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4276 -2.3464 0.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5534 1.5414 0.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0880 1.4234 -2.5803 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4370 3.3725 -0.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3557 2.1790 -1.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6624 1.5618 1.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1749 0.6074 2.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7117 -0.0425 2.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4976 -2.3052 0.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9913 -1.7015 1.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5557 -2.0772 -0.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9366 -2.4580 0.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1359 0.6191 -1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7386 2.9351 -0.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2941 2.2042 -0.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3347 3.0791 2.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7528 4.0931 2.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5337 3.9861 1.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6470 1.2515 3.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4554 1.1683 3.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6370 -0.7789 2.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9309 -0.8821 2.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6972 3.3404 1.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1171 2.3887 0.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2263 1.6507 1.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8134 -1.3756 -1.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5298 -1.6678 0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5132 -3.8120 -0.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9512 -4.6562 -0.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1930 -4.2179 2.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7467 -3.0454 -2.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2899 -2.9246 -3.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6753 -4.3557 -0.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2332 -3.0826 -2.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0863 -4.6602 -2.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4623 -0.6991 -1.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1361 -0.5872 -2.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9381 -2.1887 -1.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4835 -1.3703 -1.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1140 -1.0646 -1.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4688 0.0203 -2.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9553 0.4939 -2.8435 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2869 0.3062 -2.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9814 -2.3974 -2.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9163 -1.8659 -1.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7312 -3.5313 0.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3565 -3.1772 -3.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9343 -1.1854 -3.3919 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 11 14 1 0 10 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 1 1 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 1 41 43 1 0 43 44 1 0 41 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 38 49 1 6 49 50 2 0 49 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 57 62 1 0 28 63 1 6 20 64 1 6 5 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 66 69 1 0 65 70 1 0 67 3 1 0 12 7 1 0 22 16 1 0 34 28 1 0 44 38 1 0 59 52 1 0 29 20 1 0 39 33 1 0 1 71 1 0 2 72 1 0 2 73 1 0 3 74 1 1 5 75 1 1 7 76 1 1 8 77 1 0 8 78 1 0 10 79 1 1 11 80 1 1 12 81 1 6 13 82 1 0 14 83 1 0 16 84 1 1 17 85 1 1 18 86 1 0 19 87 1 0 19 88 1 0 21 89 1 1 23 90 1 0 23 91 1 0 23 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 26 96 1 0 26 97 1 0 27 98 1 0 27 99 1 0 29100 1 1 30101 1 6 31102 1 0 32103 1 0 35104 1 0 35105 1 0 35106 1 0 36107 1 0 36108 1 0 37109 1 0 37110 1 0 39111 1 6 40112 1 0 40113 1 0 42114 1 0 42115 1 0 42116 1 0 43117 1 0 43118 1 0 44119 1 0 44120 1 0 48121 1 0 48122 1 0 48123 1 0 52124 1 6 54125 1 6 55126 1 0 55127 1 0 56128 1 0 57129 1 6 58130 1 6 59131 1 1 60132 1 0 61133 1 0 62134 1 0 63135 1 0 63136 1 0 63137 1 0 64138 1 0 64139 1 0 64140 1 0 65141 1 6 66142 1 1 67143 1 6 68144 1 0 69145 1 0 70146 1 0 M END

Standard InCHIKey	QCEJNSUFOBLNLD-MTJZKYCXSA-N
Standard InCHI	InChI=1S/C48H76O22/c1-43(41(62)64-6)9-11-48(42(63)70-40-35(61)32(58)29(55)25(17-50)67-40)12-10-46(4)20(21(48)14-43)13-22(52)36-44(2)15-23(53)37(45(3,19-51)27(44)7-8-47(36,46)5)69-38-33(59)30(56)26(18-65-38)68-39-34(60)31(57)28(54)24(16-49)66-39/h13,21-40,49-61H,7-12,14-19H2,1-6H3/t21-,22+,23-,24+,25+,26+,27+,28+,29+,30-,31-,32-,33+,34+,35+,36+,37-,38-,39-,40-,43-,44-,45-,46+,47+,48-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3[C@H](O)C=C3[C@@]2(C)CC[C@@]2([C@H]3C[C@](C)(CC2)C(=O)OC)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

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
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	roots	n.a.	n.a.	PMID[18177012]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26595875]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	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
Activity	5
IC50	3

Activity Type	# Activity
Cell line	5
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	121.0	%	PMID[8893846]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	119.0	%	PMID[8893846]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	124.0	%	PMID[8893846]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell line	WI-38	Homo sapiens	IC50	>	100000.0	nM	PMID[16413779]
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	94000.0	nM	PMID[16413779]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[16413779]
NPT81	Cell line	A549	Homo sapiens	Activity	>	100.0	uM	PMID[17417907]

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 NPC471547 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	20299
0.1-0.2	24596
0.2-0.3	3923
0.3-0.4	821
0.4-0.5	168
0.5-0.6	33
0.6-0.7	4
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8495	Intermediate Similarity	NPC471548
0.8478	Intermediate Similarity	NPC473343
0.8211	Intermediate Similarity	NPC473401
0.75	Intermediate Similarity	NPC473373
0.7216	Intermediate Similarity	NPC139894
0.703	Intermediate Similarity	NPC109588
0.6538	Remote Similarity	NPC309714
0.6262	Remote Similarity	NPC473405
0.6168	Remote Similarity	NPC473383
0.6154	Remote Similarity	NPC150400
0.5943	Remote Similarity	NPC295371
0.5922	Remote Similarity	NPC29069
0.5865	Remote Similarity	NPC48499
0.5566	Remote Similarity	NPC179434
0.5536	Remote Similarity	NPC63159
0.5377	Remote Similarity	NPC214484
0.5328	Remote Similarity	NPC100639
0.5328	Remote Similarity	NPC471550
0.5299	Remote Similarity	NPC241909
0.5289	Remote Similarity	NPC475899
0.525	Remote Similarity	NPC76972
0.525	Remote Similarity	NPC469782
0.525	Remote Similarity	NPC204414
0.5243	Remote Similarity	NPC68419
0.5234	Remote Similarity	NPC298034
0.5234	Remote Similarity	NPC71065
0.5217	Remote Similarity	NPC297263
0.5197	Remote Similarity	NPC65105
0.5196	Remote Similarity	NPC237503
0.5175	Remote Similarity	NPC102439
0.5175	Remote Similarity	NPC473459
0.5138	Remote Similarity	NPC475208
0.5133	Remote Similarity	NPC223301
0.5133	Remote Similarity	NPC171544
0.5122	Remote Similarity	NPC135904
0.5093	Remote Similarity	NPC90856
0.5089	Remote Similarity	NPC39211
0.5088	Remote Similarity	NPC104071
0.5088	Remote Similarity	NPC30735
0.5086	Remote Similarity	NPC222580
0.5082	Remote Similarity	NPC192600
0.5082	Remote Similarity	NPC79643
0.5081	Remote Similarity	NPC470218

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7049
0.1-0.2	2035
0.2-0.3	62
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