NPASS Compound

Natural Product: NPC109588

Natural Product ID	NPC109588
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,12Ar,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-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-11-Oxo-3,4,5,6,6A,7,8,8A,10,12,13,14B-Dodecahydro-1H-Picene-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,12aR,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-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-11-oxo-3,4,5,6,6a,7,8,8a,10,12,13,14b-dodecahydro-1H-picene-2,4a-dicarboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL402231
PubChem CID	24770164
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 143150 0 0 0 0 0 0 0 0999 V2000 13.7524 -1.8923 -2.1875 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4158 -0.5705 -1.9228 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5266 -0.5569 -0.7015 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3828 -1.3081 -0.9605 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5570 -1.2600 0.1900 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3373 -1.7182 -0.1975 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3065 -0.8016 -0.1128 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2357 -1.1693 0.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1108 -1.5927 0.1978 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4423 -0.5514 -0.4545 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4266 0.3365 -1.1678 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7382 -0.3809 -1.4070 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5537 0.5463 -2.0975 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9680 0.7694 -2.4047 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8062 0.1886 0.5280 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4519 0.2369 0.4129 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7711 -0.5238 1.5441 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5184 -1.0456 2.3447 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3012 -0.5899 1.6141 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6073 0.7219 1.3136 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3572 1.4355 0.2579 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8249 1.6087 0.4235 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2634 2.3214 1.6659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3635 2.3988 -0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1060 1.8483 -1.9616 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6528 2.7269 -0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6771 2.3306 -0.7663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5063 1.4354 0.0813 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7127 0.3090 0.6597 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5270 -0.6371 1.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9847 -0.5346 1.1824 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5304 0.1110 0.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5880 0.7807 -0.7642 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9318 -0.2984 -1.6324 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2897 1.7096 -1.6647 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4881 1.0989 -2.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4680 0.4453 -1.4073 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9692 0.1563 -0.0142 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7497 -0.9852 0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7053 -2.2658 -0.1396 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7998 -3.2781 0.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2998 -2.0542 -1.5786 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0095 -0.8136 -2.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0455 -2.9310 -0.1958 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0205 -2.3820 0.3610 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2447 -4.1337 -0.8429 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5419 -4.7365 -0.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6690 1.3641 -1.3297 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6463 2.4884 -1.9023 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8249 1.0512 -0.6571 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9463 1.9128 -0.5841 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1526 2.2976 0.7213 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2431 1.7308 1.3369 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9758 1.6543 2.8245 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8473 0.8777 3.0770 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5037 0.3143 0.8653 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7852 0.2467 -0.6012 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1536 1.3997 -1.2994 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0787 2.4371 -1.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3532 -0.9837 -1.1036 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6675 -0.1263 1.5276 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1533 2.3078 1.1310 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4358 1.4357 2.6094 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1785 -2.2223 1.1708 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6594 -2.4522 0.8366 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3021 -1.1629 0.4475 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3138 -0.3329 1.5691 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7819 -3.4349 -0.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1798 -1.6743 2.4666 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2623 -2.1836 -3.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9447 -0.0671 -2.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3511 -0.0315 -1.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2752 0.4802 -0.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5888 -0.2170 0.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8085 0.1305 0.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9377 -0.3083 1.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6624 -1.9577 1.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7613 -0.9971 -1.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6429 1.2268 -0.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5177 -1.1956 -2.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6368 1.3147 -1.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3534 1.6079 -2.7076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -0.3005 -0.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0330 -0.9561 2.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9738 -1.4129 0.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2498 0.7928 -0.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3506 2.5885 1.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7732 3.3307 1.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2545 1.7301 2.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1615 3.5014 -0.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4895 2.3721 -0.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9474 2.5173 -2.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2328 3.1374 -1.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5755 3.4535 0.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2454 3.3070 -0.8625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5427 2.0050 -1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3274 -0.2863 -0.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2612 -1.7156 1.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3962 -0.5317 2.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6363 -1.0237 1.8807 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8577 -1.2724 -1.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9805 0.0510 -2.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5640 -0.5314 -2.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5820 2.6892 -1.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5801 1.9514 -2.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2364 0.3912 -3.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9782 1.9527 -2.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3304 1.0517 0.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8415 -0.6502 0.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5577 -1.0064 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7477 -3.1638 0.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8557 -3.0631 1.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1734 -4.3156 0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -2.0447 -1.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6796 -2.9146 -2.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8576 -0.7251 -3.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0928 -0.9466 -1.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2533 -4.0847 -1.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9694 -4.8399 0.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4975 -5.7184 -1.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6361 2.8447 -1.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1846 2.3410 1.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7747 2.6641 3.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8562 1.2517 3.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0967 1.4133 3.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6771 -0.3094 1.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8939 0.2968 -0.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8476 1.1673 -2.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8010 2.1007 -2.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5494 -1.0669 -2.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4585 -0.1181 0.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3952 3.0281 1.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6450 1.7797 1.9396 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8471 3.0044 0.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6886 2.4999 2.5948 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1101 1.0036 3.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5771 1.3452 3.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7136 -3.2291 1.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1136 -2.8736 1.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3586 -1.3954 0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6551 0.5843 1.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6787 -4.3360 0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8061 -0.7508 2.4791 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 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 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 31 32 2 0 32 33 1 0 33 34 1 6 33 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 40 42 1 0 42 43 1 0 40 44 1 0 44 45 2 0 44 46 1 0 46 47 1 0 37 48 1 1 48 49 2 0 48 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 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 28 62 1 1 20 63 1 1 5 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 65 68 1 0 64 69 1 0 66 3 1 0 12 7 1 0 22 16 1 0 33 28 1 0 43 37 1 0 58 51 1 0 29 20 1 0 38 32 1 0 1 70 1 0 2 71 1 0 2 72 1 0 3 73 1 1 5 74 1 1 7 75 1 1 8 76 1 0 8 77 1 0 10 78 1 6 11 79 1 1 12 80 1 6 13 81 1 0 14 82 1 0 16 83 1 6 19 84 1 0 19 85 1 0 21 86 1 6 23 87 1 0 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 25 92 1 0 26 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 29 97 1 6 30 98 1 0 30 99 1 0 31100 1 0 34101 1 0 34102 1 0 34103 1 0 35104 1 0 35105 1 0 36106 1 0 36107 1 0 38108 1 1 39109 1 0 39110 1 0 41111 1 0 41112 1 0 41113 1 0 42114 1 0 42115 1 0 43116 1 0 43117 1 0 47118 1 0 47119 1 0 47120 1 0 51121 1 6 53122 1 1 54123 1 0 54124 1 0 55125 1 0 56126 1 6 57127 1 1 58128 1 6 59129 1 0 60130 1 0 61131 1 0 62132 1 0 62133 1 0 62134 1 0 63135 1 0 63136 1 0 63137 1 0 64138 1 1 65139 1 1 66140 1 6 67141 1 0 68142 1 0 69143 1 0 M END

Standard InCHIKey	ODARBAYTGJLCBX-WOSKTBFYSA-N
Standard InCHI	InChI=1S/C48H74O21/c1-43(41(61)63-6)11-13-48(42(62)69-40-36(60)33(57)30(54)25(18-50)66-40)14-12-46(4)21(22(48)15-43)7-8-28-44(2)16-23(52)37(45(3,20-51)27(44)9-10-47(28,46)5)68-38-34(58)31(55)26(19-64-38)67-39-35(59)32(56)29(53)24(17-49)65-39/h7,22,24-40,49-51,53-60H,8-20H2,1-6H3/t22-,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]2C(=O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=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

Molecular Weight:	986.47	Volume:	944.361 ? Van der Waals volume.
Dense:	1.045	LogP:	-0.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.72 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.962 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	47.0
TPSA:	338.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.597	Fsp³:	0.896
MCE-18:	175.824 ? 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:	0.777	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.171

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.609	MDCK Permeability:	-5.127
Pgp-inhibitor:	0.0	Pgp-substrate:	0.036
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):	0.374
20% Bioavailability (F20%):	0.169	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039	MRP1:	0.146
Plasma Protein Binding (PPB):	67.907%	Volume Distribution (VD):	-0.34
Fu:	26.73% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.052
BSEP inhibitor:	0.043

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:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.755
HLM stability:	0.0 ? 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):

0.137

Half-life (T1/2):

3.031

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.919	Drug-induced Liver Injury (DILI):	0.896
AMES Toxicity:	0.965	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.341	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.716	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.778	RPMI-8226 Immunitoxicity:	0.156
A549 Cytotoxicity:	0.798	Hek293 Cytotoxicity:	0.178
BCF:	0.506 ? 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:	3.32 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.905 ? 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
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	=	120.0	%	PMID[25990761]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	115.0	%	PMID[21377877]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	98.0	%	DrugMatrix in vitro pharmacology data

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	Activity	>	101.0	uM	PMID[22264149]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	101000.0	nM	Open TG-GATES in vivo data: Hematology
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	>	101000.0	nM	PMID[23301767]
NPT1374	Cell line	WI-38	Homo sapiens	IC50	>	101000.0	nM	PMID[25136754]

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 NPC109588 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	19713
0.1-0.2	25164
0.2-0.3	3883
0.3-0.4	804
0.4-0.5	178
0.5-0.6	98
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.828	Intermediate Similarity	NPC473373
0.8105	Intermediate Similarity	NPC473343
0.7059	Intermediate Similarity	NPC309714
0.703	Intermediate Similarity	NPC471547
0.699	Remote Similarity	NPC473401
0.69	Remote Similarity	NPC139894
0.6893	Remote Similarity	NPC471548
0.6768	Remote Similarity	NPC29069
0.6602	Remote Similarity	NPC295371
0.6535	Remote Similarity	NPC48499
0.602	Remote Similarity	NPC237503
0.6	Remote Similarity	NPC63159
0.5909	Remote Similarity	NPC102439
0.5909	Remote Similarity	NPC473459
0.5909	Remote Similarity	NPC473383
0.59	Remote Similarity	NPC68419
0.5888	Remote Similarity	NPC150400
0.5882	Remote Similarity	NPC100639
0.5877	Remote Similarity	NPC241909
0.5865	Remote Similarity	NPC214484
0.5818	Remote Similarity	NPC104071
0.5816	Remote Similarity	NPC167383
0.575	Remote Similarity	NPC471550
0.5714	Remote Similarity	NPC90856
0.5678	Remote Similarity	NPC76972
0.5678	Remote Similarity	NPC469782
0.5678	Remote Similarity	NPC204414
0.5676	Remote Similarity	NPC30735
0.5635	Remote Similarity	NPC298034
0.5635	Remote Similarity	NPC71065
0.563	Remote Similarity	NPC192600
0.56	Remote Similarity	NPC65105
0.5596	Remote Similarity	NPC249848
0.5596	Remote Similarity	NPC107966
0.5586	Remote Similarity	NPC223301
0.5586	Remote Similarity	NPC171544
0.5577	Remote Similarity	NPC256798
0.5575	Remote Similarity	NPC148417
0.5545	Remote Similarity	NPC39211
0.5537	Remote Similarity	NPC155410
0.5537	Remote Similarity	NPC135904
0.5528	Remote Similarity	NPC481080
0.5526	Remote Similarity	NPC297263
0.5526	Remote Similarity	NPC609763
0.55	Remote Similarity	NPC79643
0.5492	Remote Similarity	NPC475160
0.5492	Remote Similarity	NPC470218
0.5492	Remote Similarity	NPC473714
0.547	Remote Similarity	NPC295823
0.547	Remote Similarity	NPC174720
0.547	Remote Similarity	NPC475467
0.5405	Remote Similarity	NPC473884
0.5392	Remote Similarity	NPC116794
0.5391	Remote Similarity	NPC222580
0.5385	Remote Similarity	NPC481079
0.5377	Remote Similarity	NPC209894
0.5364	Remote Similarity	NPC235405
0.5364	Remote Similarity	NPC475516
0.5357	Remote Similarity	NPC469946
0.5351	Remote Similarity	NPC10607
0.534	Remote Similarity	NPC306746
0.534	Remote Similarity	NPC199457
0.5321	Remote Similarity	NPC179434
0.5312	Remote Similarity	NPC481081
0.531	Remote Similarity	NPC112352
0.5304	Remote Similarity	NPC235438
0.53	Remote Similarity	NPC191763
0.5299	Remote Similarity	NPC104372
0.5289	Remote Similarity	NPC60557
0.5289	Remote Similarity	NPC67857
0.5288	Remote Similarity	NPC137917
0.5285	Remote Similarity	NPC123199
0.5278	Remote Similarity	NPC189884
0.5278	Remote Similarity	NPC138334
0.5276	Remote Similarity	NPC41061
0.5276	Remote Similarity	NPC227551
0.5276	Remote Similarity	NPC258617
0.5273	Remote Similarity	NPC136877
0.5271	Remote Similarity	NPC261506
0.5271	Remote Similarity	NPC4328
0.5259	Remote Similarity	NPC475504
0.5238	Remote Similarity	NPC476068
0.5234	Remote Similarity	NPC293330
0.5234	Remote Similarity	NPC43550
0.5217	Remote Similarity	NPC251768
0.5217	Remote Similarity	NPC101744
0.5217	Remote Similarity	NPC11551
0.5217	Remote Similarity	NPC480475
0.5194	Remote Similarity	NPC202828
0.5194	Remote Similarity	NPC119592
0.5194	Remote Similarity	NPC305981
0.5192	Remote Similarity	NPC37739
0.5189	Remote Similarity	NPC220984
0.5167	Remote Similarity	NPC31838
0.5146	Remote Similarity	NPC605954
0.514	Remote Similarity	NPC128925
0.5094	Remote Similarity	NPC271138
0.5094	Remote Similarity	NPC102914
0.5094	Remote Similarity	NPC110139
0.5094	Remote Similarity	NPC108709
0.5086	Remote Similarity	NPC40775
0.5086	Remote Similarity	NPC46665
0.5085	Remote Similarity	NPC134835
0.5083	Remote Similarity	NPC80986
0.5083	Remote Similarity	NPC480474
0.5079	Remote Similarity	NPC488560
0.5043	Remote Similarity	NPC192791
0.5043	Remote Similarity	NPC473405
0.5042	Remote Similarity	NPC73318
0.5038	Remote Similarity	NPC250247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC109588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6906
0.1-0.2	2190
0.2-0.3	49
0.3-0.4	5
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