NPASS Compound

Natural Product: NPC473401

Natural Product ID	NPC473401
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,14Bs)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5-[(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-11-Hydroxy-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-13-Oxo-3,4,5,6,6A,7,8,8A,10,11,12,14B-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,11S,12aS,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2,4a-dicarboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL412721
PubChem CID	44448126
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 144151 0 0 0 0 0 0 0 0999 V2000 12.2069 0.6180 2.9954 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5324 0.8459 1.6704 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0488 -0.2969 0.7724 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6846 -0.3739 0.9054 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1202 -1.3253 0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7318 -1.2025 0.1060 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0812 -2.3317 0.5617 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0721 -2.8359 -0.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7622 -2.7167 0.0496 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5433 -1.3285 0.2395 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2869 -1.0135 1.5378 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3406 -2.0352 1.8522 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8331 -3.2205 2.3610 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9099 0.2191 1.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2025 -1.0707 0.3411 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6579 -0.2843 -0.6579 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6626 -0.9982 -1.5062 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2250 -2.2744 -1.7683 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3168 -1.2307 -0.9297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -0.0622 -0.0326 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6686 1.1038 -0.4734 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1177 1.0363 -0.1141 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4739 1.2410 1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7966 2.1637 -0.9055 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1921 2.0299 -0.6971 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0761 2.4550 -0.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3909 2.5707 -0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2063 1.4165 0.1234 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5652 0.2402 -0.4781 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4322 -0.9240 -0.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1117 -2.0987 -0.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7807 -0.6848 -1.0081 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3611 0.4683 -0.8157 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6663 1.5448 -0.1052 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8495 2.9407 -0.6777 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5098 1.6359 1.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8240 0.9795 1.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 1.0081 -0.1301 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7637 0.6247 -1.2847 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9497 1.3861 -2.5403 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2886 2.0471 -2.6862 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1462 3.0276 -3.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6451 2.8827 -1.5347 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4314 2.2369 -0.2314 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3224 1.0850 -3.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9886 -0.0939 -3.4010 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6517 1.4366 -3.2882 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5836 0.4480 -3.7293 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6666 -0.0803 0.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7736 -1.1081 -0.5300 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5256 0.0374 1.2391 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4995 -0.9230 1.5784 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7839 -0.4675 1.5905 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6734 -1.4867 1.7533 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6847 -1.1515 2.8625 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5485 -2.2423 2.9603 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1327 -2.8566 1.9298 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9278 -2.9324 2.8351 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2173 -1.5832 2.9104 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8590 -1.6942 3.0759 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2299 -3.4320 4.0984 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8960 -3.5102 0.7211 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9535 1.6689 1.5856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 -0.5544 1.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5469 -1.2167 -1.3643 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0215 -1.0222 -1.5483 C 0 0 2 0 0 0 0 0 0 0 0 0 12.4706 0.0877 -0.6376 C 0 0 2 0 0 0 0 0 0 0 0 0 13.8609 0.1299 -0.6583 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2325 -0.6446 -2.8837 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1998 -2.4066 -2.0039 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2737 -0.3563 3.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6236 1.0113 1.5683 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0429 1.7597 1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5990 -1.2002 1.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3914 -2.3437 0.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8051 -3.1280 0.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2482 -3.9252 -0.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1287 -2.2504 -1.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9936 -0.8529 -0.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5689 -0.9763 2.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0138 -1.5992 2.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3285 -2.9786 3.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1052 0.4317 0.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5365 -0.0614 -1.3374 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6508 -0.5205 -2.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9723 -2.1601 -2.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3106 -2.1905 -0.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6163 -1.3757 -1.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6741 1.0028 -1.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4984 1.7234 1.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8257 1.9032 1.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6146 0.3038 1.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6275 2.0333 -1.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4596 3.1616 -0.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6156 2.5632 -1.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5351 3.1270 -1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4279 2.9793 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4731 2.3621 -1.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6849 3.5502 -0.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3804 0.5030 -1.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3040 -1.5179 -1.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 3.1838 -1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8731 3.2496 -0.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5721 3.6140 0.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9833 1.0852 2.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6021 2.6679 1.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8135 -0.0689 1.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4865 1.5158 1.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1462 -0.4172 -1.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9373 0.7016 -3.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0855 2.0510 -2.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0826 2.4491 -4.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2712 3.6454 -3.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1101 3.5873 -3.8816 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0336 3.8234 -1.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7122 3.2541 -1.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9669 3.0302 0.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4568 2.1423 0.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1071 -0.3373 -4.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0178 -0.0516 -2.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3796 0.9668 -4.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4056 -1.7239 0.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3102 -1.5042 0.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1692 -1.0578 3.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2644 -0.2785 2.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4927 -1.9735 3.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9337 -3.4714 2.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2057 -3.6335 2.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6987 -1.0461 3.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4696 -2.5265 2.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0632 -4.3945 4.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1044 -4.4653 0.7723 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6197 2.5207 1.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0391 0.8434 2.2626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0612 2.1232 1.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7399 -1.3967 1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2522 0.1285 2.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0380 -1.1418 1.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0273 -0.3500 -1.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6225 -1.9214 -1.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0487 1.0716 -0.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1850 1.0801 -0.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0194 0.3075 -2.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8109 -2.1620 -2.8733 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 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 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 1 6 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 6 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 1 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 1 20 64 1 1 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 0 7 76 1 1 8 77 1 0 8 78 1 0 10 79 1 6 11 80 1 1 12 81 1 1 13 82 1 0 14 83 1 0 16 84 1 6 17 85 1 6 18 86 1 0 19 87 1 0 19 88 1 0 21 89 1 6 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 6 32101 1 0 35102 1 0 35103 1 0 35104 1 0 36105 1 0 36106 1 0 37107 1 0 37108 1 0 39109 1 6 40110 1 0 40111 1 0 42112 1 0 42113 1 0 42114 1 0 43115 1 0 43116 1 0 44117 1 0 44118 1 0 48119 1 0 48120 1 0 48121 1 0 52122 1 6 54123 1 6 55124 1 0 55125 1 0 56126 1 0 57127 1 1 58128 1 6 59129 1 1 60130 1 0 61131 1 0 62132 1 0 63133 1 0 63134 1 0 63135 1 0 64136 1 0 64137 1 0 64138 1 0 65139 1 6 66140 1 1 67141 1 6 68142 1 0 69143 1 0 70144 1 0 M END

Standard InCHIKey	DTFZRJDDQMLMNU-OPJOLPNKSA-N
Standard InCHI	InChI=1S/C48H74O22/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/h13,21,23-40,49-51,53-61H,7-12,14-19H2,1-6H3/t21-,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]1OC(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]3C(=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

Molecular Weight:	1002.47	Volume:	953.151 ? Van der Waals volume.
Dense:	1.052	LogP:	-0.936 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.44 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.617 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	47.0
TPSA:	358.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	12.0	Rings:	8.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.609	Fsp³:	0.896
MCE-18:	178.571 ? 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:	0.669	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.121 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.826	MDCK Permeability:	-5.067
Pgp-inhibitor:	0.0	Pgp-substrate:	0.526
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):	0.486
20% Bioavailability (F20%):	0.232	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.159
Plasma Protein Binding (PPB):	63.207%	Volume Distribution (VD):	-0.311
Fu:	27.826% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.006
BSEP inhibitor:	0.002

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:	0.636	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.595
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):

0.055

Half-life (T1/2):

3.33

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.962	Drug-induced Liver Injury (DILI):	0.951
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.335	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.701	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.847	RPMI-8226 Immunitoxicity:	0.196
A549 Cytotoxicity:	0.737	Hek293 Cytotoxicity:	0.15
BCF:	0.449 ? 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:	3.291 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.157 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.06 ? 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	=	155.0	%	PMID[20350943]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	135.0	%	PMID[16417306]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	119.0	%	PMID[17027268]

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	>	98.8	uM	PMID[12828470]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	97400.0	nM	PubChem BioAssay data set
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	>	98800.0	nM	PMID[17958396]
NPT1374	Cell line	WI-38	Homo sapiens	IC50	>	98800.0	nM	Open TG-GATES in vivo data: Pathology

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 NPC473401 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	20305
0.1-0.2	24686
0.2-0.3	3767
0.3-0.4	849
0.4-0.5	194
0.5-0.6	44
0.6-0.7	3
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
0.8211	Intermediate Similarity	NPC471547
0.8211	Intermediate Similarity	NPC473343
0.8041	Intermediate Similarity	NPC471548
0.7273	Intermediate Similarity	NPC473373
0.7172	Intermediate Similarity	NPC139894
0.699	Remote Similarity	NPC109588
0.6355	Remote Similarity	NPC309714
0.6	Remote Similarity	NPC473383
0.5981	Remote Similarity	NPC150400
0.5946	Remote Similarity	NPC473405
0.5926	Remote Similarity	NPC295371
0.5755	Remote Similarity	NPC29069
0.5701	Remote Similarity	NPC48499
0.5686	Remote Similarity	NPC187056
0.5686	Remote Similarity	NPC606216
0.5686	Remote Similarity	NPC607023
0.5556	Remote Similarity	NPC241909
0.5556	Remote Similarity	NPC179434
0.5447	Remote Similarity	NPC100639
0.5447	Remote Similarity	NPC471550
0.541	Remote Similarity	NPC475899
0.5391	Remote Similarity	NPC63159
0.5372	Remote Similarity	NPC76972
0.5372	Remote Similarity	NPC469782
0.5372	Remote Similarity	NPC204414
0.5349	Remote Similarity	NPC298034
0.5349	Remote Similarity	NPC71065
0.5312	Remote Similarity	NPC65105
0.5304	Remote Similarity	NPC102439
0.5273	Remote Similarity	NPC475208
0.5254	Remote Similarity	NPC247315
0.5254	Remote Similarity	NPC482728
0.5242	Remote Similarity	NPC135904
0.5217	Remote Similarity	NPC104071
0.5203	Remote Similarity	NPC192600
0.52	Remote Similarity	NPC475160
0.52	Remote Similarity	NPC473714
0.5167	Remote Similarity	NPC295823
0.5167	Remote Similarity	NPC174720
0.5167	Remote Similarity	NPC475467
0.5128	Remote Similarity	NPC148417
0.512	Remote Similarity	NPC155410
0.5118	Remote Similarity	NPC481080
0.5094	Remote Similarity	NPC68419
0.5091	Remote Similarity	NPC90856
0.5091	Remote Similarity	NPC214484
0.5085	Remote Similarity	NPC297263
0.5083	Remote Similarity	NPC481079
0.5048	Remote Similarity	NPC237503
0.5043	Remote Similarity	NPC473459
0.5038	Remote Similarity	NPC202828
0.5038	Remote Similarity	NPC119592

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7084
0.1-0.2	2004
0.2-0.3	56
0.3-0.4	6
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