NPASS Compound

Natural Product: NPC273189

Natural Product ID	NPC273189
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Clethroidoside D
IUPAC Name	n.a.
Synonyms	Clethroidoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1927849
PubChem CID	56598062
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 157166 0 0 0 0 0 0 0 0999 V2000 -9.5969 -4.3974 0.3452 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6620 -2.8992 0.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2225 -2.4911 1.7707 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5707 -2.3812 -0.6436 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5710 -0.8995 -0.8243 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2515 -0.2597 -0.8018 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2204 1.1524 -0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0619 1.2773 0.4998 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3077 0.0829 0.3751 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5355 -0.2015 1.6074 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2806 0.5857 1.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5189 0.6410 0.5390 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1020 1.1337 0.6665 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9518 2.3289 1.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2900 0.0200 1.3312 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3644 -0.6765 0.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 0.2248 -0.2760 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0660 1.4032 -0.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5766 2.7329 -0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8042 1.3700 -2.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5543 1.2357 -0.7209 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2803 2.2186 -1.5822 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6501 1.6022 -1.8025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3571 1.2540 -0.5335 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9897 2.5783 -0.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4592 0.2272 -0.8580 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8069 -1.0891 -1.2218 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2606 0.6227 -2.0626 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5042 -0.2348 -2.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8468 -0.8578 -3.0450 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7132 0.5085 0.5913 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8715 -0.1364 0.2433 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1566 0.5781 0.3641 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2622 -0.3292 -0.1514 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0730 -1.7289 0.2734 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6782 -2.1885 0.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8983 -1.2716 1.1559 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9264 -2.1146 1.3149 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8228 -3.1171 0.9551 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2667 -2.7373 1.1490 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9707 -3.9685 1.7442 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4300 -4.1202 3.1518 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9291 -4.2870 2.9866 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2383 -3.2465 3.8014 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6942 -3.3996 5.1386 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5353 -4.2474 1.6853 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9604 -5.2907 3.6672 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3337 -3.9039 1.6681 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8944 -2.4394 -0.0658 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4280 -1.1807 -0.1485 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9294 -1.1701 -0.3296 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3799 -1.7931 -1.6205 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5768 -1.2120 -2.7493 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6562 -0.1482 -2.2310 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8490 -0.5230 -1.1994 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4545 -0.6916 -3.7254 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2670 -3.1849 -1.5883 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4097 0.1359 -0.2575 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4269 0.1383 0.5245 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1766 1.6895 -0.4792 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5478 2.8739 0.1995 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8061 3.3824 -0.4476 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8480 4.8314 -0.7705 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5427 5.5383 -0.8684 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7027 5.0440 0.3205 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3896 5.7825 0.2980 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5295 5.3006 1.2821 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 3.7150 0.0961 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7522 6.9037 -0.7457 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 5.0033 -2.0093 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8988 3.1388 0.4102 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4171 -0.8817 0.3089 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2438 -2.3104 0.2284 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6451 -4.7422 -0.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4635 -4.8183 -0.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6563 -4.8533 1.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4433 -2.2106 2.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7839 -3.3642 2.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9369 -1.6617 1.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3429 -2.8526 -1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6040 -2.7035 -0.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0370 -0.7051 -1.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2540 -0.3751 -0.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3300 1.9081 -1.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1276 1.2213 0.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2111 0.0110 2.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3194 -1.2915 1.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6566 -0.0487 2.5281 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4153 1.5154 2.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4017 -0.4545 0.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8793 2.3897 1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4899 2.0999 2.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3401 3.2628 1.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9676 -0.7874 1.7367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7158 0.3709 2.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8209 -1.3420 -0.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7356 -1.3512 1.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0947 -0.4571 -1.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0673 2.5577 0.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3803 3.4772 -0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 3.2375 -1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5053 0.7058 -2.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7724 2.3966 -2.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2140 0.9299 -2.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7642 0.2275 -1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7958 2.2515 -2.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3225 3.2379 -1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5143 0.7923 -2.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2340 2.3834 -2.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2353 3.4021 -0.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8355 2.8686 -0.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2368 2.6500 0.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7813 -1.0020 -1.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3511 -1.6011 -2.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7705 -1.8039 -0.3856 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5938 1.6402 -2.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6839 0.3651 -2.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -0.6579 -0.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3997 0.8844 1.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4003 -0.2142 -1.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4575 -2.3702 -0.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6165 -3.2004 0.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1397 -2.3494 -0.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6624 -3.4166 -0.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2974 -1.8951 1.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6206 -4.8350 1.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7171 -3.2366 3.7217 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6771 -5.3118 3.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5557 -2.2286 3.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1509 -3.3748 3.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8497 -4.3772 5.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1568 -5.9241 2.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7394 -4.7844 1.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2464 -0.5936 0.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4545 -1.7178 0.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4512 -1.5205 -1.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0326 -2.0355 -3.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1848 0.8318 -2.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9563 0.0793 -3.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2395 -1.2552 -3.8651 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3569 -3.5022 -1.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2658 0.2529 -0.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3076 -0.0928 1.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7562 2.6481 1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0234 2.7991 -1.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4743 5.4001 -0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0238 5.3368 -1.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2864 5.2403 1.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9299 5.6213 -0.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5719 6.8781 0.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3891 5.5412 1.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7193 7.1345 -0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0302 5.8550 -2.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9312 3.8019 1.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0470 -0.6686 1.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9346 -2.7645 -0.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6537 -2.6994 1.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 7 8 1 0 9 8 1 1 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 2 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 51 58 1 0 34 59 1 0 33 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 66 67 1 0 65 68 1 0 64 69 1 0 63 70 1 0 62 71 1 0 9 72 1 0 72 73 1 0 73 2 1 0 72 6 1 0 29 6 1 0 37 32 1 0 46 39 1 0 55 50 1 0 68 61 1 0 26 9 1 0 24 12 1 0 21 13 1 0 1 74 1 0 1 75 1 0 1 76 1 0 3 77 1 0 3 78 1 0 3 79 1 0 4 80 1 0 4 81 1 0 5 82 1 0 5 83 1 0 7 84 1 0 7 85 1 0 10 86 1 0 10 87 1 0 11 88 1 0 11 89 1 0 12 90 1 6 14 91 1 0 14 92 1 0 14 93 1 0 15 94 1 0 15 95 1 0 16 96 1 0 16 97 1 0 17 98 1 6 19 99 1 0 19100 1 0 19101 1 0 20102 1 0 20103 1 0 20104 1 0 21105 1 6 22106 1 0 22107 1 0 23108 1 0 23109 1 0 25110 1 0 25111 1 0 25112 1 0 27113 1 0 27114 1 0 27115 1 0 28116 1 0 28117 1 0 32118 1 6 33119 1 1 34120 1 6 35121 1 6 36122 1 0 36123 1 0 39124 1 6 40125 1 1 41126 1 6 42127 1 1 43128 1 1 44129 1 0 44130 1 0 45131 1 0 47132 1 0 48133 1 0 50134 1 1 51135 1 1 52136 1 6 53137 1 6 54138 1 0 54139 1 0 56140 1 0 57141 1 0 58142 1 0 59143 1 0 61144 1 1 62145 1 6 63146 1 1 64147 1 6 65148 1 1 66149 1 0 66150 1 0 67151 1 0 69152 1 0 70153 1 0 71154 1 0 72155 1 1 73156 1 0 73157 1 0 M END

Standard InCHIKey	LXYNMISGVPYMHU-LGZUVIOGSA-N
Standard InCHI	InChI=1S/C52H84O21/c1-46(2)14-15-51-22-67-52(29(51)16-46)13-9-28-48(5)11-10-31(47(3,4)27(48)8-12-49(28,6)50(52,7)17-30(51)56)71-44-40(73-43-39(64)36(61)33(58)24(18-53)68-43)35(60)26(21-66-44)70-45-41(37(62)34(59)25(19-54)69-45)72-42-38(63)32(57)23(55)20-65-42/h23-29,31-45,53-55,57-64H,8-22H2,1-7H3/t23-,24-,25-,26+,27+,28-,29-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,48+,49-,50+,51-,52+/m1/s1
SMILES	CC1(C)CC[C@@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@@H](C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC3=O)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1044.55	Volume:	1004.341 ? Van der Waals volume.
Dense:	1.04	LogP:	0.623 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.564 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	54.0
TPSA:	322.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	10.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.958	Fsp³:	0.981
MCE-18:	282.35 ? 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:	0.948	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.218	Promiscuous compounds:	0.054

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.383	MDCK Permeability:	-5.219
Pgp-inhibitor:	0.0	Pgp-substrate:	0.091
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):	0.077
20% Bioavailability (F20%):	0.086	30% Bioavailability (F30%):	0.929
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.411	MRP1:	0.013
Plasma Protein Binding (PPB):	73.736%	Volume Distribution (VD):	-0.461
Fu:	17.733% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.227	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.02	CYP3A4-substrate:	0.051
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.048 ? 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):

-0.157

Half-life (T1/2):

2.999

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.772	Drug-induced Liver Injury (DILI):	0.885
AMES Toxicity:	0.985	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.049	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.73	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.131	RPMI-8226 Immunitoxicity:	0.258
A549 Cytotoxicity:	0.789	Hek293 Cytotoxicity:	0.363
BCF:	1.187 ? 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:	3.464 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.852 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.974 ? 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
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21278	Lysimachia clethroides	Species	Primulaceae	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	5

Activity Type	# Activity
Cell line	5

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
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1980.0	nM	PMID[21928797]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	1730.0	nM	PMID[21928797]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	1360.0	nM	PMID[21928797]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2360.0	nM	PMID[21928797]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	1910.0	nM	PMID[21928797]

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 NPC273189 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	24680
0.1-0.2	21844
0.2-0.3	2357
0.3-0.4	723
0.4-0.5	196
0.5-0.6	15
0.6-0.7	29
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC184805
0.7981	Intermediate Similarity	NPC77717
0.7876	Intermediate Similarity	NPC471430
0.7788	Intermediate Similarity	NPC267637
0.75	Intermediate Similarity	NPC470622
0.7431	Intermediate Similarity	NPC138219
0.7431	Intermediate Similarity	NPC475234
0.7364	Intermediate Similarity	NPC471375
0.7297	Intermediate Similarity	NPC51579
0.7248	Intermediate Similarity	NPC87393
0.7222	Intermediate Similarity	NPC253611
0.7222	Intermediate Similarity	NPC488782
0.7091	Intermediate Similarity	NPC471373
0.7054	Intermediate Similarity	NPC473688
0.6952	Remote Similarity	NPC18724
0.6842	Remote Similarity	NPC209798
0.6838	Remote Similarity	NPC471425
0.6814	Remote Similarity	NPC475630
0.678	Remote Similarity	NPC189575
0.6762	Remote Similarity	NPC80640
0.6754	Remote Similarity	NPC471374
0.6697	Remote Similarity	NPC323231
0.6695	Remote Similarity	NPC66513
0.6637	Remote Similarity	NPC40716
0.6612	Remote Similarity	NPC106701
0.661	Remote Similarity	NPC262567
0.66	Remote Similarity	NPC80417
0.6549	Remote Similarity	NPC267238
0.6525	Remote Similarity	NPC205129
0.6423	Remote Similarity	NPC471426
0.6393	Remote Similarity	NPC231566
0.6364	Remote Similarity	NPC158051
0.6348	Remote Similarity	NPC148593
0.6311	Remote Similarity	NPC471429
0.629	Remote Similarity	NPC471427
0.6273	Remote Similarity	NPC224003
0.6261	Remote Similarity	NPC207693
0.6228	Remote Similarity	NPC119628
0.621	Remote Similarity	NPC22709
0.6207	Remote Similarity	NPC157571
0.6195	Remote Similarity	NPC171741
0.6167	Remote Similarity	NPC126753
0.6032	Remote Similarity	NPC471424
0.5938	Remote Similarity	NPC471431
0.5833	Remote Similarity	NPC609281
0.582	Remote Similarity	NPC607904
0.5763	Remote Similarity	NPC158367
0.5714	Remote Similarity	NPC470623
0.5691	Remote Similarity	NPC610461
0.5667	Remote Similarity	NPC606145
0.5573	Remote Similarity	NPC471626
0.5565	Remote Similarity	NPC610204
0.5528	Remote Similarity	NPC606553
0.5489	Remote Similarity	NPC471428
0.5433	Remote Similarity	NPC603137
0.5433	Remote Similarity	NPC609305
0.536	Remote Similarity	NPC185466
0.5126	Remote Similarity	NPC469946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7326
0.1-0.2	1790
0.2-0.3	31
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