NPASS Compound

Natural Product: NPC473373

Natural Product ID	NPC473373
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,10S,12Ar,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-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-2,4A-Dicarboxylate
IUPAC Name	2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,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-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL403995
PubChem CID	44448281
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 8.9127 -4.8908 -0.6402 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1790 -4.3346 -0.4668 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4934 -3.3975 -1.6122 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5682 -2.3579 -1.6967 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6069 -1.5634 -0.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6775 -0.5504 -0.7039 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6090 -0.6798 0.1953 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3529 -0.8846 -0.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0499 0.2976 -1.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5536 1.2105 -0.3196 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7341 1.6310 0.4415 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5412 0.5342 1.0494 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1682 0.2427 2.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6094 2.2692 -0.4947 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5601 0.5117 0.3054 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2622 0.9785 0.0121 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6437 0.0442 -0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1749 0.1089 -1.1358 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4863 -0.0144 0.2062 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9529 1.1190 1.0461 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4293 1.3353 1.1613 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9723 0.5853 2.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6612 2.8160 1.5315 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9635 3.0637 1.8609 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2519 1.1109 2.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1113 0.5981 2.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8249 0.1651 1.2016 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9818 0.2252 -0.0293 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6189 -0.6369 -1.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9223 0.0274 -1.3446 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5605 0.8038 -0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0361 1.0732 0.8954 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6687 2.4965 1.1799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1811 0.7313 1.8526 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2665 1.7156 1.5769 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8595 1.6109 0.1940 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8662 1.4022 -0.8882 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5634 2.5251 -1.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2667 3.8120 -1.6290 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3294 4.9827 -1.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8634 4.0615 -0.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7010 2.8559 0.0227 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3956 3.9468 -2.6192 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5863 2.9891 -3.4164 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1826 5.0735 -2.6443 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2510 5.2196 -3.5681 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8595 0.4948 0.2707 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0990 0.6966 0.0721 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5347 -0.8187 0.5539 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5322 -1.8441 0.6122 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5129 -2.5704 1.7730 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4976 -3.5193 1.7896 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9937 -4.8644 2.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9700 -5.3395 1.5355 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2133 -3.7565 0.5054 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3197 -3.7569 -0.7031 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1647 -2.8052 -0.5280 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8587 -2.1236 -1.6926 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8646 -5.0118 -1.0652 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3065 -2.9173 0.2894 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4585 -1.1876 1.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6903 -1.3687 0.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9485 -1.0005 -0.2663 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8881 -1.3658 -1.3969 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9096 -2.8668 -1.5220 C 0 0 2 0 0 0 0 0 0 0 0 0 12.6552 -3.2382 -2.6205 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1524 -0.9403 -1.0459 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8607 0.4109 -0.2825 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5048 -5.2244 0.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3319 -3.8792 0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8774 -5.2201 -0.4783 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4169 -3.9773 -2.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2503 -2.1790 0.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7623 -1.5960 0.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4458 -1.7067 -1.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5289 -1.1493 0.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1793 2.0631 -0.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5333 2.4625 1.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6136 0.9528 1.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3895 0.7637 2.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3418 2.7176 0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4737 1.8997 -0.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9578 -0.9876 -0.7536 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0644 0.2126 -2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8981 -0.7393 -1.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7859 1.0268 -1.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5785 2.0540 0.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0682 0.4834 2.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8899 1.1878 3.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5924 -0.4299 2.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4604 3.4078 0.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9507 3.1831 2.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 4.0200 1.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2436 2.1835 2.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9485 0.6276 3.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1057 -0.2504 3.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8134 1.3334 2.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0187 1.2743 -0.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7736 -1.6974 -0.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0921 -0.6864 -2.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3879 -0.1091 -2.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5708 2.6737 1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0381 3.2277 0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0375 2.8401 2.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8690 0.8513 2.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5678 -0.2602 1.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0074 2.7673 1.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0814 1.4736 2.3294 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3220 0.5800 -1.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4538 2.7542 -1.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7381 2.2411 -2.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4979 5.0575 -1.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9507 4.7934 -2.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9000 5.9413 -2.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5566 4.9394 -0.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1280 4.3127 0.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4301 2.7498 -0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2704 3.0459 0.9580 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0195 5.9225 -3.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8558 5.6236 -4.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7580 4.2807 -3.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5450 -1.3978 0.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2661 -3.1955 2.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6585 -4.7627 3.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8608 -5.5573 2.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1347 -6.3006 1.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6649 -4.7952 0.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9254 -3.3717 -1.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2501 -3.3344 -0.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3619 -2.7752 -2.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6117 -4.9914 -2.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8664 -3.3437 -0.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7452 -2.0085 1.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9772 -1.0920 2.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2446 -1.4661 0.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1137 -2.0807 0.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7517 -1.7494 0.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5117 -1.4254 1.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3540 -1.2634 0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5218 -0.8821 -2.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3365 -3.2529 -0.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8421 -4.2161 -2.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6148 -0.5017 -1.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7308 0.7557 -1.1880 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 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 6 39 41 1 0 41 42 1 0 39 43 1 0 43 44 2 0 43 45 1 0 45 46 1 0 36 47 1 1 47 48 2 0 47 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 27 61 1 1 19 62 1 1 5 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 65 3 1 0 12 7 1 0 21 16 1 0 32 27 1 0 42 36 1 0 57 50 1 0 28 19 1 0 37 31 1 0 1 69 1 0 2 70 1 0 2 71 1 0 3 72 1 6 5 73 1 0 7 74 1 1 8 75 1 0 8 76 1 0 10 77 1 6 11 78 1 1 12 79 1 1 13 80 1 0 14 81 1 0 16 82 1 6 17 83 1 0 17 84 1 0 18 85 1 0 18 86 1 0 20 87 1 6 22 88 1 0 22 89 1 0 22 90 1 0 23 91 1 0 23 92 1 0 24 93 1 0 25 94 1 0 25 95 1 0 26 96 1 0 26 97 1 0 28 98 1 6 29 99 1 0 29100 1 0 30101 1 0 33102 1 0 33103 1 0 33104 1 0 34105 1 0 34106 1 0 35107 1 0 35108 1 0 37109 1 6 38110 1 0 38111 1 0 40112 1 0 40113 1 0 40114 1 0 41115 1 0 41116 1 0 42117 1 0 42118 1 0 46119 1 0 46120 1 0 46121 1 0 50122 1 6 52123 1 1 53124 1 0 53125 1 0 54126 1 0 55127 1 1 56128 1 6 57129 1 1 58130 1 0 59131 1 0 60132 1 0 61133 1 0 61134 1 0 61135 1 0 62136 1 0 62137 1 0 62138 1 0 63139 1 1 64140 1 6 65141 1 1 66142 1 0 67143 1 0 68144 1 0 M END

Standard InCHIKey	UVWCAIWHFSJANE-BVSYVCARSA-N
Standard InCHI	InChI=1S/C48H76O20/c1-43(41(60)62-6)13-15-48(42(61)68-40-37(59)34(56)31(53)25(19-50)65-40)16-14-46(4)22(23(48)17-43)7-8-28-44(2)11-10-29(45(3,21-51)27(44)9-12-47(28,46)5)67-38-35(57)32(54)26(20-63-38)66-39-36(58)33(55)30(52)24(18-49)64-39/h7,23-40,49-59H,8-21H2,1-6H3/t23-,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]2CC[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:	972.49	Volume:	938.207 ? Van der Waals volume.
Dense:	1.037	LogP:	0.45 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.322 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.582 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	46.0
TPSA:	321.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.07	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.446	Fsp³:	0.917
MCE-18:	173.935 ? 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:	0.799	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.147	Promiscuous compounds:	0.027

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.588	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.0	Pgp-substrate:	0.079
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):	0.04
20% Bioavailability (F20%):	0.145	30% Bioavailability (F30%):	0.96
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038	MRP1:	0.097
Plasma Protein Binding (PPB):	67.373%	Volume Distribution (VD):	-0.345
Fu:	27.297% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.028
BSEP inhibitor:	0.021

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.029	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.497
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):

0.107

Half-life (T1/2):

3.146

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.923	Drug-induced Liver Injury (DILI):	0.909
AMES Toxicity:	0.961	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	1.0
Carcinogencity:	0.394	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.514	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.867	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.722	Hek293 Cytotoxicity:	0.2
BCF:	0.552 ? 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:	3.425 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.107 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.032 ? 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	=	126.0	%	PMID[25136754]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	101.0	%	PMID[6481359]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	124.0	%	PMID[8699183]

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	>	103.0	uM	PMID[25066952]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	103000.0	nM	PMID[3236014]
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	>	103000.0	nM	PMID[17922550]
NPT1374	Cell line	WI-38	Homo sapiens	IC50	>	103000.0	nM	PMID[23399722]

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 NPC473373 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	19271
0.1-0.2	24901
0.2-0.3	4160
0.3-0.4	1033
0.4-0.5	296
0.5-0.6	111
0.6-0.7	63
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC473343
0.828	Intermediate Similarity	NPC109588
0.828	Intermediate Similarity	NPC309714
0.7957	Intermediate Similarity	NPC295371
0.7717	Intermediate Similarity	NPC48499
0.75	Intermediate Similarity	NPC471547
0.7368	Intermediate Similarity	NPC139894
0.7347	Intermediate Similarity	NPC471548
0.7273	Intermediate Similarity	NPC473401
0.7234	Intermediate Similarity	NPC29069
0.7019	Intermediate Similarity	NPC241909
0.6947	Remote Similarity	NPC214484
0.6863	Remote Similarity	NPC63159
0.6818	Remote Similarity	NPC100639
0.6818	Remote Similarity	NPC471550
0.6809	Remote Similarity	NPC256798
0.6771	Remote Similarity	NPC90856
0.6697	Remote Similarity	NPC192600
0.6667	Remote Similarity	NPC30735
0.6606	Remote Similarity	NPC76972
0.6606	Remote Similarity	NPC469782
0.6606	Remote Similarity	NPC204414
0.66	Remote Similarity	NPC249848
0.66	Remote Similarity	NPC107966
0.6569	Remote Similarity	NPC223301
0.6569	Remote Similarity	NPC171544
0.6538	Remote Similarity	NPC148417
0.6535	Remote Similarity	NPC473884
0.6535	Remote Similarity	NPC39211
0.6496	Remote Similarity	NPC298034
0.6496	Remote Similarity	NPC71065
0.6466	Remote Similarity	NPC65105
0.6452	Remote Similarity	NPC237503
0.6429	Remote Similarity	NPC189884
0.6429	Remote Similarity	NPC155410
0.6429	Remote Similarity	NPC138334
0.6404	Remote Similarity	NPC481080
0.64	Remote Similarity	NPC136877
0.6389	Remote Similarity	NPC295823
0.6389	Remote Similarity	NPC174720
0.6389	Remote Similarity	NPC475467
0.6372	Remote Similarity	NPC475160
0.6372	Remote Similarity	NPC473714
0.6337	Remote Similarity	NPC235405
0.6337	Remote Similarity	NPC475516
0.6321	Remote Similarity	NPC297263
0.6296	Remote Similarity	NPC481079
0.6286	Remote Similarity	NPC102439
0.6286	Remote Similarity	NPC11551
0.6286	Remote Similarity	NPC473459
0.6286	Remote Similarity	NPC473383
0.6283	Remote Similarity	NPC135904
0.6275	Remote Similarity	NPC150400
0.625	Remote Similarity	NPC79643
0.6237	Remote Similarity	NPC167383
0.6228	Remote Similarity	NPC470218
0.6226	Remote Similarity	NPC235438
0.6204	Remote Similarity	NPC104372
0.619	Remote Similarity	NPC104071
0.6168	Remote Similarity	NPC222580
0.6168	Remote Similarity	NPC475504
0.6154	Remote Similarity	NPC469946
0.6146	Remote Similarity	NPC68419
0.6132	Remote Similarity	NPC10607
0.6122	Remote Similarity	NPC128925
0.6095	Remote Similarity	NPC112352
0.6068	Remote Similarity	NPC476068
0.605	Remote Similarity	NPC293330
0.6018	Remote Similarity	NPC60557
0.6018	Remote Similarity	NPC67857
0.6	Remote Similarity	NPC202828
0.6	Remote Similarity	NPC119592
0.6	Remote Similarity	NPC481081
0.6	Remote Similarity	NPC123199
0.5981	Remote Similarity	NPC40775
0.5981	Remote Similarity	NPC251768
0.5981	Remote Similarity	NPC480475
0.5966	Remote Similarity	NPC41061
0.5966	Remote Similarity	NPC227551
0.5966	Remote Similarity	NPC258617
0.595	Remote Similarity	NPC261506
0.595	Remote Similarity	NPC4328
0.5917	Remote Similarity	NPC43550
0.5905	Remote Similarity	NPC157868
0.59	Remote Similarity	NPC209894
0.5897	Remote Similarity	NPC488560
0.5893	Remote Similarity	NPC31838
0.5882	Remote Similarity	NPC78046
0.5868	Remote Similarity	NPC305981
0.5849	Remote Similarity	NPC475171
0.5833	Remote Similarity	NPC159309
0.5833	Remote Similarity	NPC46665
0.5833	Remote Similarity	NPC86222
0.5804	Remote Similarity	NPC80986
0.5794	Remote Similarity	NPC192791
0.5794	Remote Similarity	NPC242840
0.5784	Remote Similarity	NPC204458
0.5766	Remote Similarity	NPC281148
0.5755	Remote Similarity	NPC470512
0.5727	Remote Similarity	NPC609763
0.5714	Remote Similarity	NPC301449
0.5714	Remote Similarity	NPC601290
0.5688	Remote Similarity	NPC101744
0.5684	Remote Similarity	NPC191763
0.568	Remote Similarity	NPC250247
0.5673	Remote Similarity	NPC179434
0.5664	Remote Similarity	NPC480474
0.5657	Remote Similarity	NPC137917
0.5641	Remote Similarity	NPC165204
0.5636	Remote Similarity	NPC475591
0.5636	Remote Similarity	NPC236870
0.5631	Remote Similarity	NPC269095
0.5625	Remote Similarity	NPC114484
0.5614	Remote Similarity	NPC481078
0.5614	Remote Similarity	NPC187290
0.5612	Remote Similarity	NPC116794
0.5586	Remote Similarity	NPC31193
0.5556	Remote Similarity	NPC37739
0.5556	Remote Similarity	NPC306746
0.5556	Remote Similarity	NPC199457
0.5545	Remote Similarity	NPC173859
0.5545	Remote Similarity	NPC148603
0.5534	Remote Similarity	NPC47063
0.5534	Remote Similarity	NPC195132
0.5526	Remote Similarity	NPC480473
0.5514	Remote Similarity	NPC58448
0.5495	Remote Similarity	NPC470515
0.5484	Remote Similarity	NPC236638
0.5484	Remote Similarity	NPC294453
0.5446	Remote Similarity	NPC110139
0.5446	Remote Similarity	NPC470513
0.5446	Remote Similarity	NPC108709
0.5413	Remote Similarity	NPC161674
0.5398	Remote Similarity	NPC134835
0.5397	Remote Similarity	NPC70809
0.5392	Remote Similarity	NPC220984
0.5357	Remote Similarity	NPC473405
0.5357	Remote Similarity	NPC162574
0.5354	Remote Similarity	NPC46388
0.5354	Remote Similarity	NPC605954
0.5339	Remote Similarity	NPC475287
0.5315	Remote Similarity	NPC160415
0.531	Remote Similarity	NPC470514
0.5304	Remote Similarity	NPC486564
0.53	Remote Similarity	NPC204407
0.5294	Remote Similarity	NPC271138
0.5294	Remote Similarity	NPC102914
0.5289	Remote Similarity	NPC191827
0.5288	Remote Similarity	NPC284807
0.5283	Remote Similarity	NPC1046
0.5259	Remote Similarity	NPC481030
0.5254	Remote Similarity	NPC185466
0.525	Remote Similarity	NPC475899
0.5248	Remote Similarity	NPC57362
0.5238	Remote Similarity	NPC136768
0.5234	Remote Similarity	NPC475208
0.5229	Remote Similarity	NPC173583
0.5225	Remote Similarity	NPC75417
0.5217	Remote Similarity	NPC73318
0.5196	Remote Similarity	NPC604133
0.5169	Remote Similarity	NPC75287
0.5168	Remote Similarity	NPC469777
0.5161	Remote Similarity	NPC57484
0.5139	Remote Similarity	NPC469775
0.5137	Remote Similarity	NPC469774
0.5135	Remote Similarity	NPC76497
0.5133	Remote Similarity	NPC305267
0.5128	Remote Similarity	NPC470516
0.5124	Remote Similarity	NPC470911
0.512	Remote Similarity	NPC110633
0.5096	Remote Similarity	NPC476883
0.5088	Remote Similarity	NPC68175
0.5088	Remote Similarity	NPC139044
0.5088	Remote Similarity	NPC118440
0.5079	Remote Similarity	NPC475514
0.5066	Remote Similarity	NPC469772
0.5049	Remote Similarity	NPC7870
0.5049	Remote Similarity	NPC310014
0.5049	Remote Similarity	NPC269315
0.5049	Remote Similarity	NPC75747
0.5048	Remote Similarity	NPC476884
0.5047	Remote Similarity	NPC473481
0.5047	Remote Similarity	NPC51947
0.5042	Remote Similarity	NPC470915
0.5034	Remote Similarity	NPC100925

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7061
0.1-0.2	2017
0.2-0.3	64
0.3-0.4	7
0.4-0.5	1
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