NPASS Compound

Natural Product: NPC163183

Natural Product ID	NPC163183
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Perennisoside Ii
IUPAC Name	[(2S,3R,4S,5R,6R)-6-(acetyloxymethyl)-5-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-9-(acetyloxymethyl)-10,11-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	perennisoside II
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503955
PubChem CID	24879273
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 155162 0 0 0 0 0 0 0 0999 V2000 -0.4815 1.6542 -3.5891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 2.2372 -2.2070 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9493 3.6742 -2.1467 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1106 3.7637 -1.1549 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1649 2.7953 -1.7136 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5771 1.4113 -1.5587 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2133 1.4750 -1.2858 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2172 0.6459 -0.6030 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8148 -0.4848 -1.0990 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2998 -0.5285 -0.8101 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8435 -1.6529 -1.6813 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1565 -2.9125 -1.1310 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7022 -4.1475 -1.8200 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0926 -4.1615 -1.6982 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8015 -5.2100 -2.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1888 -6.1401 -2.8735 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2763 -5.3435 -2.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7929 -2.8255 -1.2229 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2847 -1.7768 -0.5062 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9035 -1.8464 -0.3307 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1745 -1.7828 0.8023 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7769 -1.6149 1.8664 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3114 -1.9144 0.7299 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6958 -3.3998 0.8129 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1816 -4.0210 2.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4201 -3.2508 3.3206 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6116 -3.8855 4.0327 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7440 -3.4907 4.3048 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6939 -1.7930 3.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0327 -1.2703 1.8433 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4713 -1.1068 1.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4669 -1.2518 2.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9166 -1.0847 2.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1365 -0.2532 0.9308 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3741 0.6260 0.9271 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3946 1.7094 1.9270 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5027 -0.3374 1.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2003 -0.7944 -0.0170 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8980 0.3833 -0.5724 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9059 1.5092 -0.9128 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4116 2.7276 -0.2408 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0066 1.6283 -2.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3189 2.5339 -3.1293 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3357 3.8863 -3.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1662 4.5461 -2.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4005 4.6229 -4.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5426 1.0631 -0.5182 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4220 1.9776 -0.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1352 1.1328 -0.8859 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9156 0.4151 0.4173 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3581 1.4087 1.3779 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 -0.7330 0.1585 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6109 -1.8429 -0.5705 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7360 -0.3131 -0.6101 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7187 -1.4001 -0.6259 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8384 0.8128 0.3776 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2082 -1.6839 0.4423 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1944 -1.7838 -1.4492 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9917 0.6245 -0.9135 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6361 0.9124 0.2836 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3303 2.2422 0.8737 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5661 2.7751 1.6154 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1494 1.6231 2.3951 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5112 0.5256 1.4296 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9818 0.2259 1.4502 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3260 -0.0471 2.7915 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0306 0.8155 0.1420 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2863 2.1115 3.0608 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5256 3.2061 0.7101 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2893 2.2392 1.7977 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3103 3.1577 -3.0518 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5748 5.0755 -1.2073 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0851 4.5400 -1.7996 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1911 0.7472 -3.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 1.4293 -4.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0456 2.3567 -4.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5687 2.2403 -1.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3043 3.9731 -3.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7774 3.4497 -0.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0761 2.9491 -1.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6965 0.9002 -2.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6670 -0.5369 -2.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3980 -0.9461 0.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5878 -1.4859 -2.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4539 -3.0022 -0.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3629 -4.2178 -2.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3020 -5.0293 -1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5423 -5.8818 -1.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7481 -4.3369 -2.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6530 -5.8981 -3.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7191 -1.7875 0.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3081 -3.9583 -0.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7766 -3.4560 0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -4.1539 1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5865 -5.0555 2.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2893 -4.8973 4.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9172 -3.2796 4.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4497 -3.9803 3.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9624 -2.5259 4.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5626 -4.3215 4.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6606 -3.7218 3.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3847 -1.3712 3.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2834 -1.2826 3.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6541 -0.1756 1.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1640 -1.5251 3.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3470 -0.6715 3.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3451 -2.1233 2.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4192 -1.0093 0.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3406 2.7460 1.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3583 1.6985 2.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6256 1.6692 2.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1940 -1.2295 1.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2969 0.1636 1.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5917 -1.3941 -0.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4975 0.0789 -1.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7131 3.5841 -0.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3299 3.0678 -0.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7974 2.5081 0.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8494 0.5947 -2.8769 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1233 1.7796 -2.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4061 4.1264 -4.1851 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3375 5.6753 -3.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8240 4.6211 -5.2022 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3433 0.1242 -1.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2869 2.8231 -0.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4725 2.4055 -1.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 1.8949 -0.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0938 0.5194 -1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8807 2.3977 1.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3292 1.1400 2.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2879 1.6743 1.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1414 -2.5481 0.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8990 -2.5217 -1.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2553 -1.4646 -1.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2339 0.6043 -0.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0273 -0.1116 -1.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9654 -2.2785 -1.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1826 -0.9744 -1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5090 0.0682 0.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8001 -2.2479 1.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7481 -1.3770 -2.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3807 0.1222 1.0310 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0745 3.0168 0.1202 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2527 3.6100 2.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3722 1.2994 3.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9924 -0.4068 1.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6132 1.0343 1.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1911 -0.7201 0.9039 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8536 -0.8870 3.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0768 2.1184 4.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7827 4.1316 0.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4409 2.9720 2.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2653 3.3566 -3.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4490 5.0788 -1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3225 5.4131 -1.5756 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 2 0 15 17 1 0 12 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 23 21 1 1 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 1 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 1 40 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 40 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 1 50 52 1 0 52 53 1 6 52 54 1 0 54 55 1 0 39 56 1 0 38 57 1 0 11 58 1 0 10 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 62 69 1 0 61 70 1 0 5 71 1 0 4 72 1 0 3 73 1 0 7 2 1 0 19 9 1 0 55 23 1 0 67 60 1 0 30 23 1 0 52 31 1 0 50 34 1 0 47 35 1 0 1 74 1 0 1 75 1 0 1 76 1 0 2 77 1 1 3 78 1 6 4 79 1 1 5 80 1 1 6 81 1 6 9 82 1 6 10 83 1 1 11 84 1 6 12 85 1 1 13 86 1 0 13 87 1 0 17 88 1 0 17 89 1 0 17 90 1 0 19 91 1 1 24 92 1 0 24 93 1 0 25 94 1 0 25 95 1 0 27 96 1 0 27 97 1 0 27 98 1 0 28 99 1 0 28100 1 0 28101 1 0 29102 1 0 29103 1 0 30104 1 1 32105 1 0 33106 1 0 33107 1 0 34108 1 6 36109 1 0 36110 1 0 36111 1 0 37112 1 0 37113 1 0 38114 1 6 39115 1 6 41116 1 0 41117 1 0 41118 1 0 42119 1 0 42120 1 0 46121 1 0 46122 1 0 46123 1 0 47124 1 6 48125 1 0 48126 1 0 49127 1 0 49128 1 0 51129 1 0 51130 1 0 51131 1 0 53132 1 0 53133 1 0 53134 1 0 54135 1 0 54136 1 0 55137 1 0 55138 1 0 56139 1 0 57140 1 0 58141 1 0 60142 1 1 61143 1 6 62144 1 1 63145 1 1 64146 1 1 65147 1 0 65148 1 0 66149 1 0 68150 1 0 69151 1 0 70152 1 0 71153 1 0 72154 1 0 73155 1 0 M END

Standard InCHIKey	IXKGHYXQFAQYES-UAJXJGMFSA-N
Standard InCHI	InChI=1S/C52H82O21/c1-23-33(57)36(60)38(62)43(68-23)72-41-40(71-44-39(63)37(61)34(58)29(20-53)69-44)35(59)30(21-66-24(2)54)70-45(41)73-46(65)52-16-14-47(4,5)18-27(52)26-10-11-32-48(6)19-28(56)42(64)49(7,22-67-25(3)55)31(48)12-13-51(32,9)50(26,8)15-17-52/h10,23,27-45,53,56-64H,11-22H2,1-9H3/t23-,27-,28-,29+,30+,31+,32+,33-,34-,35+,36+,37-,38+,39+,40-,41+,42-,43-,44-,45-,48-,49-,50+,51+,52-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](COC(=O)C)O[C@H]1OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@@](C)(COC(=O)C)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O)O)O)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

Molecular Weight:	1042.53	Volume:	1013.545 ? Van der Waals volume.
Dense:	1.029	LogP:	1.227 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.064 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.147 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	47.0
TPSA:	327.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.618	Fsp³:	0.904
MCE-18:	178.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.901	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.157	Promiscuous compounds:	0.257

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.262	MDCK Permeability:	-5.123
Pgp-inhibitor:	0.0	Pgp-substrate:	0.767
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):	0.498
20% Bioavailability (F20%):	0.981	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.478
Plasma Protein Binding (PPB):	71.235%	Volume Distribution (VD):	-0.435
Fu:	19.474% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.0
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.78
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.931 ? 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):

0.044

Half-life (T1/2):

2.273

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.458	Drug-induced Liver Injury (DILI):	0.585
AMES Toxicity:	0.966	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.164	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.903	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	0.159	RPMI-8226 Immunitoxicity:	0.173
A549 Cytotoxicity:	0.966	Hek293 Cytotoxicity:	0.296
BCF:	0.491 ? 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:	3.693 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.862 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.899 ? 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
NPO5225	Bellis perennis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[18363378]
NPO5225	Bellis perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5225	Bellis perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5225	Bellis perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5225	Bellis perennis	Species	Asteraceae	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	9

Activity Type	# Activity
Organism	9

Molecular-level activity

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

In vitro activity

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	204.6	mg/dl	PMID[21339031]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	147.0	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	87.0	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	232.5	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	180.4	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	104.6	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	179.4	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	155.6	mg/dl	PMID[19035792]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	80.6	mg/dl	PMID[19035792]

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 NPC163183 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	22913
0.1-0.2	22715
0.2-0.3	3201
0.3-0.4	666
0.4-0.5	233
0.5-0.6	122
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96641
0.6396	Remote Similarity	NPC46665
0.6033	Remote Similarity	NPC475899
0.5983	Remote Similarity	NPC481079
0.5965	Remote Similarity	NPC10607
0.5935	Remote Similarity	NPC100639
0.5932	Remote Similarity	NPC80986
0.5929	Remote Similarity	NPC112352
0.581	Remote Similarity	NPC68419
0.581	Remote Similarity	NPC604133
0.5776	Remote Similarity	NPC475591
0.5776	Remote Similarity	NPC236870
0.5739	Remote Similarity	NPC104071
0.5728	Remote Similarity	NPC167383
0.5726	Remote Similarity	NPC135904
0.5714	Remote Similarity	NPC199457
0.569	Remote Similarity	NPC102439
0.5676	Remote Similarity	NPC48499
0.5669	Remote Similarity	NPC57484
0.5664	Remote Similarity	NPC150400
0.562	Remote Similarity	NPC187290
0.5619	Remote Similarity	NPC237503
0.5615	Remote Similarity	NPC477463
0.5591	Remote Similarity	NPC487505
0.5586	Remote Similarity	NPC29069
0.5575	Remote Similarity	NPC235405
0.5556	Remote Similarity	NPC473459
0.5538	Remote Similarity	NPC293330
0.5538	Remote Similarity	NPC65105
0.5538	Remote Similarity	NPC43550
0.5526	Remote Similarity	NPC249848
0.5526	Remote Similarity	NPC107966
0.5508	Remote Similarity	NPC63159
0.5508	Remote Similarity	NPC235438
0.5496	Remote Similarity	NPC305981
0.5496	Remote Similarity	NPC481081
0.5484	Remote Similarity	NPC60557
0.5484	Remote Similarity	NPC76972
0.5484	Remote Similarity	NPC469782
0.5484	Remote Similarity	NPC67857
0.5484	Remote Similarity	NPC204414
0.5476	Remote Similarity	NPC155410
0.5462	Remote Similarity	NPC258617
0.5462	Remote Similarity	NPC609763
0.5455	Remote Similarity	NPC261506
0.5455	Remote Similarity	NPC298034
0.5455	Remote Similarity	NPC71065
0.5455	Remote Similarity	NPC4328
0.544	Remote Similarity	NPC79643
0.5433	Remote Similarity	NPC475160
0.5433	Remote Similarity	NPC473714
0.5426	Remote Similarity	NPC476068
0.541	Remote Similarity	NPC295823
0.541	Remote Similarity	NPC174720
0.541	Remote Similarity	NPC241909
0.541	Remote Similarity	NPC475467
0.5377	Remote Similarity	NPC605954
0.5372	Remote Similarity	NPC114484
0.5357	Remote Similarity	NPC214484
0.5345	Remote Similarity	NPC295371
0.5345	Remote Similarity	NPC39211
0.5344	Remote Similarity	NPC41061
0.5344	Remote Similarity	NPC227551
0.5333	Remote Similarity	NPC250247
0.5333	Remote Similarity	NPC222580
0.5333	Remote Similarity	NPC475504
0.5327	Remote Similarity	NPC116794
0.5323	Remote Similarity	NPC75287
0.5317	Remote Similarity	NPC192600
0.5315	Remote Similarity	NPC209894
0.5304	Remote Similarity	NPC475516
0.5299	Remote Similarity	NPC161674
0.5299	Remote Similarity	NPC213674
0.5294	Remote Similarity	NPC480417
0.529	Remote Similarity	NPC477464
0.5285	Remote Similarity	NPC481030
0.5263	Remote Similarity	NPC475208
0.525	Remote Similarity	NPC68175
0.5242	Remote Similarity	NPC481078
0.5238	Remote Similarity	NPC475287
0.5238	Remote Similarity	NPC300419
0.5234	Remote Similarity	NPC123199
0.5231	Remote Similarity	NPC481080
0.5229	Remote Similarity	NPC310014
0.5229	Remote Similarity	NPC269315
0.5227	Remote Similarity	NPC484942
0.521	Remote Similarity	NPC30735
0.521	Remote Similarity	NPC309714
0.5182	Remote Similarity	NPC271138
0.5177	Remote Similarity	NPC475368
0.5169	Remote Similarity	NPC473343
0.5169	Remote Similarity	NPC76497
0.5169	Remote Similarity	NPC469946
0.5167	Remote Similarity	NPC251768
0.5167	Remote Similarity	NPC164389
0.5164	Remote Similarity	NPC134835
0.5149	Remote Similarity	NPC135849
0.5149	Remote Similarity	NPC202828
0.5149	Remote Similarity	NPC119592
0.5149	Remote Similarity	NPC236638
0.5149	Remote Similarity	NPC294453
0.5138	Remote Similarity	NPC306746
0.5126	Remote Similarity	NPC192791
0.5126	Remote Similarity	NPC223301
0.5126	Remote Similarity	NPC171544
0.5122	Remote Similarity	NPC281148
0.5122	Remote Similarity	NPC73318
0.5122	Remote Similarity	NPC104372
0.512	Remote Similarity	NPC36831
0.5116	Remote Similarity	NPC480419
0.5091	Remote Similarity	NPC7870
0.5091	Remote Similarity	NPC75747
0.5085	Remote Similarity	NPC473884
0.5085	Remote Similarity	NPC157868
0.5083	Remote Similarity	NPC30289
0.5082	Remote Similarity	NPC297263
0.5045	Remote Similarity	NPC102914
0.5045	Remote Similarity	NPC110139
0.5045	Remote Similarity	NPC108709
0.5043	Remote Similarity	NPC139894
0.5042	Remote Similarity	NPC263756
0.5041	Remote Similarity	NPC159309
0.5041	Remote Similarity	NPC86222
0.5038	Remote Similarity	NPC488560
0.5036	Remote Similarity	NPC224381

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7571
0.1-0.2	1525
0.2-0.3	51
0.3-0.4	3
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