NPASS Compound

Natural Product: NPC477194

Natural Product ID	NPC477194
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3beta-[3-O-(alpha-L-Arabinopyranosyl)-beta-D-glucopyranuronosyloxy]-16alpha-acetoxy-28-hydroxy-21beta,22alpha-bis(angeloyloxy)oleana-12-ene
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-acetyloxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	gordonoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44140531
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 151157 0 0 0 0 0 0 0 0999 V2000 -9.3996 4.5584 0.0024 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2599 3.8369 -1.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4957 2.7827 -1.4644 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4608 2.1692 -2.8136 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7255 2.2452 -0.4014 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7683 2.7851 0.7441 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8750 1.1266 -0.4654 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1433 0.6401 0.6137 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6074 -0.7073 1.0092 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9486 -1.0503 2.3198 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4820 -1.2477 1.9947 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9108 0.0662 1.5847 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6339 0.7280 0.4400 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0837 0.3260 -0.8477 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9538 -0.6545 -0.9270 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8936 -0.6561 0.0767 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4779 0.0723 1.2749 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6711 0.7269 2.0671 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2070 0.8889 1.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2758 -0.0927 0.9431 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5573 -0.0124 -0.2683 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1444 -0.7433 -1.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5339 -0.1672 -1.6468 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2943 -0.4272 -0.4057 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7634 0.0570 0.8703 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3557 -0.8242 1.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6057 -1.4799 1.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4949 -0.9482 0.5114 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8047 -0.2374 -0.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1936 1.1602 -0.8810 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1250 -1.0417 -1.8640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4844 -0.1683 1.0893 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7121 -0.7920 1.1250 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7654 0.0038 0.4447 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9571 -0.9075 0.2100 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9251 -2.0527 1.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2590 -1.8682 2.4546 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0844 -1.1323 2.4361 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1840 -1.4092 3.5145 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8681 -0.4534 4.2392 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3891 -2.0447 3.6900 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4093 -3.2252 0.5380 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1641 -0.2131 0.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7039 -0.1005 -1.0645 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9752 1.3658 -1.3139 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7279 1.5975 -2.6023 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8414 0.2620 -3.3064 C 0 0 2 0 0 0 0 0 0 0 0 0 12.3587 -0.8409 -2.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9732 -0.7198 -1.0897 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7675 0.4211 -4.3622 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9783 2.1667 -2.3711 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8520 2.1463 -1.1668 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2945 0.4486 -0.7860 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2051 1.4430 1.3030 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7773 1.3732 -0.8159 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7158 -2.0919 0.5738 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0956 -0.2862 -1.6812 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4489 0.1646 -2.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8588 1.1819 -3.3725 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4851 -0.4612 -3.7753 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3918 2.2480 0.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7922 2.7191 1.8205 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2489 -0.1842 3.4636 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4575 -2.4612 2.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0060 -0.7589 1.0622 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7695 -1.6581 0.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1699 -2.5145 -0.3683 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2141 -1.7174 0.4050 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9108 -0.8570 1.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2340 0.1827 1.9362 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9821 -2.7482 -0.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4090 4.9699 0.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0318 5.4619 -0.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7779 3.9269 0.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8385 4.2176 -2.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8088 1.1350 -2.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9946 2.8089 -3.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3997 2.2095 -3.1344 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4190 1.3161 1.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2238 -1.4811 0.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5017 -2.0225 1.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0098 -1.5438 2.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1340 0.7110 2.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7815 1.2256 -1.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4664 -1.6782 -1.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5813 -0.5688 -1.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1410 1.2336 2.9351 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2671 0.6565 2.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0154 1.9321 1.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1084 -1.1551 1.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4129 -1.7975 -1.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3685 -0.6727 -2.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9381 -0.8804 -2.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5898 0.7837 -2.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2306 -1.5721 -0.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5971 -1.6288 2.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5448 -0.2349 2.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3802 -2.5715 1.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2958 -1.6284 2.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0662 -1.8786 0.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3023 1.8533 -0.9826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9596 1.6133 -0.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6663 1.2825 -1.9095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5483 -1.9798 -1.9137 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1912 -1.3504 -1.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8806 -0.4474 -2.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6384 -1.7883 0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0597 0.9209 1.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8113 -1.2688 -0.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0119 -2.3122 1.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9295 -2.8993 2.8026 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0891 -1.5395 4.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0321 -3.5571 -0.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0836 -0.5184 -1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6882 1.6673 -0.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1296 2.2730 -3.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8458 0.0322 -3.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8521 -1.7811 -2.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4415 -0.9775 -2.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3197 1.2217 -4.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9585 2.4834 -1.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9738 2.8606 -0.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3010 -0.3029 -1.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7708 2.2749 0.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8759 1.6363 2.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2811 1.5405 1.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1073 2.1007 -0.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1593 1.8314 -1.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4110 1.2774 -1.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 -2.1556 1.6877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8058 -2.5933 0.2661 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5204 -2.7663 0.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8413 0.2700 -4.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3562 -0.7590 -3.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0122 -1.3266 -4.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0351 2.7883 -0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3681 2.5348 0.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1732 3.6405 1.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3549 -0.2820 3.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7596 -0.6542 4.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9073 0.8427 3.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0287 -2.7899 3.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5447 -2.5335 2.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0289 -3.1267 1.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0015 -0.9093 1.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6407 0.8756 1.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6004 -0.2090 2.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9909 0.8366 2.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2788 -3.5428 -0.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5027 -2.2849 -1.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7336 -3.2139 0.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 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 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 28 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 2 0 39 41 1 0 36 42 1 0 35 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 45 52 1 0 34 53 1 0 25 54 1 1 21 55 1 6 16 56 1 1 14 57 1 0 57 58 1 0 58 59 2 0 58 60 1 0 13 61 1 1 61 62 1 0 10 63 1 0 10 64 1 0 9 65 1 0 65 66 1 0 66 67 2 0 66 68 1 0 68 69 2 0 69 70 1 0 68 71 1 0 13 8 1 0 17 12 1 0 21 16 1 0 25 20 1 0 29 24 1 0 38 33 1 0 49 44 1 0 1 72 1 0 1 73 1 0 1 74 1 0 2 75 1 0 4 76 1 0 4 77 1 0 4 78 1 0 8 79 1 1 9 80 1 6 11 81 1 0 11 82 1 0 12 83 1 1 14 84 1 6 15 85 1 0 15 86 1 0 18 87 1 0 19 88 1 0 19 89 1 0 20 90 1 1 22 91 1 0 22 92 1 0 23 93 1 0 23 94 1 0 24 95 1 1 26 96 1 0 26 97 1 0 27 98 1 0 27 99 1 0 28100 1 6 30101 1 0 30102 1 0 30103 1 0 31104 1 0 31105 1 0 31106 1 0 33107 1 6 34108 1 1 35109 1 6 36110 1 1 37111 1 1 41112 1 0 42113 1 0 44114 1 6 45115 1 1 46116 1 6 47117 1 6 48118 1 0 48119 1 0 50120 1 0 51121 1 0 52122 1 0 53123 1 0 54124 1 0 54125 1 0 54126 1 0 55127 1 0 55128 1 0 55129 1 0 56130 1 0 56131 1 0 56132 1 0 60133 1 0 60134 1 0 60135 1 0 61136 1 0 61137 1 0 62138 1 0 63139 1 0 63140 1 0 63141 1 0 64142 1 0 64143 1 0 64144 1 0 69145 1 0 70146 1 0 70147 1 0 70148 1 0 71149 1 0 71150 1 0 71151 1 0 M END

Standard InCHIKey	KYEPMMYYOBDIEI-KNUPQYEMSA-N
Standard InCHI	InChI=1S/C53H80O18/c1-13-25(3)44(63)70-41-42(71-45(64)26(4)14-2)53(24-54)29(21-48(41,6)7)28-15-16-32-50(10)19-18-33(49(8,9)31(50)17-20-51(32,11)52(28,12)22-34(53)66-27(5)55)67-47-38(60)39(37(59)40(69-47)43(61)62)68-46-36(58)35(57)30(56)23-65-46/h13-15,29-42,46-47,54,56-60H,16-24H2,1-12H3,(H,61,62)/b25-13-,26-14-/t29-,30-,31-,32+,33-,34+,35-,36+,37-,38+,39-,40-,41-,42-,46-,47+,50-,51+,52+,53-/m0/s1
SMILES	C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)C)C)OC(=O)C)CO)(C)C)OC(=O)/C(=C\C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1004.53	Volume:	1005.117 ? Van der Waals volume.
Dense:	0.999	LogP:	3.189 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.05 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.478 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	274.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.051	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.612	Fsp³:	0.811
MCE-18:	162.75 ? 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:	0.971	Fluc inhibitor:	0.005 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.175	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.839	MDCK Permeability:	-5.221
Pgp-inhibitor:	0.0	Pgp-substrate:	0.066
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):	0.001
20% Bioavailability (F20%):	0.593	30% Bioavailability (F30%):	0.647
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.999
Plasma Protein Binding (PPB):	79.215%	Volume Distribution (VD):	-0.604
Fu:	13.305% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.335	BCRP inhibitor:	0.0
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.945
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.725
HLM stability:	0.938 ? 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):

0.251

Half-life (T1/2):

2.363

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.473	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.902	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.057	Skin Sensitization:	1.0
Carcinogencity:	0.341	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.076
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.966
Hematotoxicity:	0.875	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.935	Hek293 Cytotoxicity:	0.553
BCF:	0.277 ? 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:	3.634 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.73 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.745 ? 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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT179	Cell line	A2780	Homo sapiens	IC50	>	10000	nM	PMID[20560647]

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 NPC477194 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	21098
0.1-0.2	24684
0.2-0.3	3099
0.3-0.4	625
0.4-0.5	286
0.5-0.6	43
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC477192
0.8173	Intermediate Similarity	NPC477193
0.757	Intermediate Similarity	NPC477191
0.7364	Intermediate Similarity	NPC477195
0.7297	Intermediate Similarity	NPC477196
0.6903	Remote Similarity	NPC477197
0.6466	Remote Similarity	NPC11242
0.6422	Remote Similarity	NPC6377
0.6422	Remote Similarity	NPC208381
0.6417	Remote Similarity	NPC602995
0.6179	Remote Similarity	NPC478597
0.616	Remote Similarity	NPC271610
0.608	Remote Similarity	NPC478596
0.6034	Remote Similarity	NPC603832
0.6033	Remote Similarity	NPC478600
0.6033	Remote Similarity	NPC478599
0.592	Remote Similarity	NPC4749
0.5873	Remote Similarity	NPC178264
0.5794	Remote Similarity	NPC192765
0.5776	Remote Similarity	NPC159309
0.5776	Remote Similarity	NPC86222
0.5748	Remote Similarity	NPC484061
0.5748	Remote Similarity	NPC484062
0.5748	Remote Similarity	NPC478598
0.5738	Remote Similarity	NPC25998
0.5703	Remote Similarity	NPC476780
0.5615	Remote Similarity	NPC484833
0.5583	Remote Similarity	NPC114484
0.5581	Remote Similarity	NPC265841
0.5573	Remote Similarity	NPC476777
0.5547	Remote Similarity	NPC329828
0.5546	Remote Similarity	NPC611191
0.5538	Remote Similarity	NPC312650
0.5504	Remote Similarity	NPC21691
0.5492	Remote Similarity	NPC477077
0.5462	Remote Similarity	NPC488308
0.5447	Remote Similarity	NPC329976
0.544	Remote Similarity	NPC609119
0.5426	Remote Similarity	NPC71391
0.541	Remote Similarity	NPC477079
0.5385	Remote Similarity	NPC470518
0.5345	Remote Similarity	NPC114441
0.5344	Remote Similarity	NPC476774
0.5268	Remote Similarity	NPC480937
0.5259	Remote Similarity	NPC476775
0.5231	Remote Similarity	NPC46823
0.5229	Remote Similarity	NPC283849
0.5221	Remote Similarity	NPC488309
0.52	Remote Similarity	NPC187290
0.5185	Remote Similarity	NPC302543
0.5161	Remote Similarity	NPC301449
0.5161	Remote Similarity	NPC601290
0.5159	Remote Similarity	NPC605294
0.5072	Remote Similarity	NPC476778
0.5043	Remote Similarity	NPC603870
0.5038	Remote Similarity	NPC283417
0.5038	Remote Similarity	NPC200049
0.5037	Remote Similarity	NPC476779
0.5036	Remote Similarity	NPC476776

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6641
0.1-0.2	2468
0.2-0.3	36
0.3-0.4	4
0.4-0.5	0
0.5-0.6	1
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
0.5526	Remote Similarity	NPD8295	Clinical (unspecified phase)

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