NPASS Compound

Natural Product: NPC477197

Natural Product ID	NPC477197
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside G
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4-methoxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-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 G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44140400
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 150156 0 0 0 0 0 0 0 0999 V2000 -10.8057 -2.3886 1.0361 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2017 -1.9234 2.3178 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0485 -1.2964 2.3705 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5306 -0.8751 3.6934 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3001 -1.0195 1.1838 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7385 -1.3729 0.0670 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0601 -0.3519 1.1995 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3319 -0.0809 0.0095 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2948 1.4071 -0.2383 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5625 1.7235 -1.4911 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9469 0.5821 -2.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3912 -0.5378 -1.3738 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9895 -0.7676 -0.0399 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1549 -0.4946 1.1577 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7571 -0.9870 1.0251 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0334 -0.5610 -0.2132 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8825 -0.5704 -1.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3329 -0.6115 -2.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8577 -0.6482 -2.8472 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0885 -0.8962 -1.5966 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8727 -1.5271 -0.5103 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0620 -1.7125 0.7469 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2945 -2.2806 0.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9972 -1.3608 -0.5076 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3113 -1.4384 -1.8201 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9855 -0.4534 -2.7709 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4560 -0.4783 -2.7611 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1461 -0.6578 -1.4573 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4709 -1.5315 -0.4602 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9522 -2.9487 -0.5776 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8649 -1.0442 0.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4187 -1.8352 1.7158 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6177 0.2556 1.3077 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9844 0.7203 2.5895 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4647 -1.1003 -1.6365 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4247 -0.1803 -1.2754 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4564 -0.6786 -0.2950 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7177 0.1516 -0.5587 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2382 -0.3448 -1.8801 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1309 -0.2819 -2.8962 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9611 0.2880 -2.4729 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9766 -1.6458 -3.4658 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8578 -2.1601 -3.5348 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0723 -2.3615 -3.9258 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4030 0.2978 -2.2929 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6561 0.0856 0.4369 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8433 1.3430 1.0319 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0087 1.2787 2.5091 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4356 2.6145 3.0487 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5169 3.2892 2.2873 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2860 3.1191 0.8067 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1144 1.7602 0.5262 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7791 2.7903 2.5878 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9326 2.3424 4.3542 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8171 0.9557 3.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0812 -0.4254 1.0261 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3795 -2.7672 -2.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5018 -2.8468 -0.8490 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5430 0.8568 -0.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0554 -0.4816 2.1432 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2058 0.7949 1.6617 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3720 -2.2671 0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0175 -2.4755 1.3104 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5213 2.8326 -1.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5895 2.3473 -2.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6674 1.8243 -0.2605 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2167 2.6759 0.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4060 3.0810 1.5782 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5933 3.1296 0.7074 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5374 2.8159 -0.1370 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1822 1.8928 -1.2675 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9767 4.0617 1.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7974 -2.8452 1.2389 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2093 -3.1804 0.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0412 -1.5280 0.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7635 -2.1196 3.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3294 -0.9420 4.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2287 0.1951 3.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6572 -1.4828 3.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9384 -0.5029 -0.8218 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8728 1.9547 0.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0836 0.9873 -2.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6579 0.2274 -2.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6390 -1.4659 -1.9939 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5940 -1.1112 2.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7519 -2.0890 1.1756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9405 -0.6221 -3.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6111 -1.3678 -3.6593 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6116 0.3612 -3.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1503 0.1505 -1.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0878 -0.7802 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6144 -2.4520 1.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3276 -3.3308 0.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8772 -2.1665 1.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8035 -0.3363 -0.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5764 -0.6282 -3.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6193 0.5626 -2.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7835 -1.2628 -3.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7968 0.4814 -3.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2600 0.3829 -1.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2885 -3.7017 -0.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9168 -3.0174 -0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2552 -3.1760 -1.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0897 0.7493 3.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4864 1.7043 2.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6802 -0.0400 3.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9633 0.7392 -0.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6732 -1.7554 -0.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3543 1.1844 -0.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5638 -1.4116 -1.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5237 0.4188 -3.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9947 -3.0276 -4.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1363 -0.3028 -2.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1403 2.1083 0.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8268 0.5448 2.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5669 3.2924 3.2264 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5301 4.3665 2.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3937 3.7215 0.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1503 3.4753 0.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2977 2.5117 1.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7195 2.9331 4.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9933 0.5260 4.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9830 0.5711 1.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3905 -3.6426 -1.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3567 -2.8390 -3.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6239 -2.9241 -3.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5268 -2.6721 -1.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6829 -3.4376 0.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9817 -3.4466 -1.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6406 0.9420 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4337 1.3924 -0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3225 1.4377 0.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3850 -0.9420 2.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 0.8648 2.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4164 -2.8113 0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9792 -2.5667 -0.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5169 -3.3044 1.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5621 3.1179 -0.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7927 3.7146 -1.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5113 2.4399 -1.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0660 2.5183 -3.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3802 1.6014 -2.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9456 3.3212 -2.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5487 3.1989 -0.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4779 2.4408 -1.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1252 1.6426 -1.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7113 0.9824 -0.9107 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3640 4.9864 1.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5739 3.5954 2.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0467 4.2367 1.8968 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 6 29 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 28 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 0 40 42 1 0 42 43 2 0 42 44 1 0 39 45 1 0 38 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 37 56 1 0 25 57 1 6 21 58 1 6 16 59 1 1 15 60 1 0 14 61 1 0 13 62 1 6 62 63 1 0 10 64 1 0 10 65 1 0 9 66 1 0 66 67 1 0 67 68 2 0 67 69 1 0 69 70 2 0 70 71 1 0 69 72 1 0 13 8 1 0 17 12 1 0 21 16 1 0 25 20 1 0 29 24 1 0 41 36 1 0 52 47 1 0 1 73 1 0 1 74 1 0 1 75 1 0 2 76 1 0 4 77 1 0 4 78 1 0 4 79 1 0 8 80 1 6 9 81 1 1 11 82 1 0 11 83 1 0 12 84 1 6 14 85 1 1 15 86 1 1 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 1 30101 1 0 30102 1 0 30103 1 0 34104 1 0 34105 1 0 34106 1 0 36107 1 1 37108 1 1 38109 1 6 39110 1 1 40111 1 6 44112 1 0 45113 1 0 47114 1 1 48115 1 6 49116 1 1 50117 1 6 51118 1 0 51119 1 0 53120 1 0 54121 1 0 55122 1 0 56123 1 0 57124 1 0 57125 1 0 57126 1 0 58127 1 0 58128 1 0 58129 1 0 59130 1 0 59131 1 0 59132 1 0 60133 1 0 61134 1 0 62135 1 0 62136 1 0 63137 1 0 64138 1 0 64139 1 0 64140 1 0 65141 1 0 65142 1 0 65143 1 0 70144 1 0 71145 1 0 71146 1 0 71147 1 0 72148 1 0 72149 1 0 72150 1 0 M END

Standard InCHIKey	VXQCKKNUNHNYPF-QAFYSKFWSA-N
Standard InCHI	InChI=1S/C52H78O20/c1-12-23(3)42(63)71-39-40(72-43(64)24(4)13-2)52(22-53)26(20-47(39,5)6)25-14-15-28-48(7)18-17-30(50(9,46(65)66-11)29(48)16-19-49(28,8)51(25,10)37(59)38(52)60)68-45-34(58)35(33(57)36(70-45)41(61)62)69-44-32(56)31(55)27(54)21-67-44/h12-14,26-40,44-45,53-60H,15-22H2,1-11H3,(H,61,62)/b23-12-,24-13-/t26-,27-,28+,29+,30-,31-,32+,33-,34+,35-,36-,37-,38+,39-,40-,44-,45+,48+,49+,50-,51-,52-/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@@H]([C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)C(=O)OC)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)O)O)CO)(C)C)OC(=O)/C(=C\C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1022.51	Volume:	1005.402 ? Van der Waals volume.
Dense:	1.017	LogP:	1.511 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.119 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.138 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	314.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.047	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.779	Fsp³:	0.808
MCE-18:	166.213 ? 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:	0.839	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.17	Promiscuous compounds:	0.217

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.973	MDCK Permeability:	-5.277
Pgp-inhibitor:	0.0	Pgp-substrate:	0.153
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%):	0.793	30% Bioavailability (F30%):	0.495
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.999
Plasma Protein Binding (PPB):	77.075%	Volume Distribution (VD):	-0.499
Fu:	17.166% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.073	BCRP inhibitor:	0.008
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.19	CYP3A4-substrate:	0.337
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.178
HLM stability:	0.867 ? 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):

0.277

Half-life (T1/2):

2.608

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.917	Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	1.0
Carcinogencity:	0.424	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.162
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.982
Hematotoxicity:	0.932	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.986	RPMI-8226 Immunitoxicity:	0.166
A549 Cytotoxicity:	0.974	Hek293 Cytotoxicity:	0.637
BCF:	0.342 ? 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:	3.461 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.387 ? 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 NPC477197 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	20020
0.1-0.2	26016
0.2-0.3	3132
0.3-0.4	529
0.4-0.5	113
0.5-0.6	32
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8381	Intermediate Similarity	NPC477196
0.7568	Intermediate Similarity	NPC478600
0.7568	Intermediate Similarity	NPC478599
0.75	Intermediate Similarity	NPC477191
0.7431	Intermediate Similarity	NPC477193
0.7297	Intermediate Similarity	NPC477195
0.7179	Intermediate Similarity	NPC478598
0.6964	Remote Similarity	NPC477192
0.6903	Remote Similarity	NPC477194
0.6667	Remote Similarity	NPC192765
0.6612	Remote Similarity	NPC178264
0.6325	Remote Similarity	NPC329976
0.632	Remote Similarity	NPC484833
0.626	Remote Similarity	NPC478597
0.6239	Remote Similarity	NPC477077
0.6032	Remote Similarity	NPC478596
0.592	Remote Similarity	NPC46823
0.584	Remote Similarity	NPC602995
0.582	Remote Similarity	NPC478152
0.582	Remote Similarity	NPC478151
0.5748	Remote Similarity	NPC71391
0.5702	Remote Similarity	NPC477078
0.5659	Remote Similarity	NPC476780
0.5652	Remote Similarity	NPC6377
0.5652	Remote Similarity	NPC208381
0.5635	Remote Similarity	NPC478150
0.5615	Remote Similarity	NPC271610
0.553	Remote Similarity	NPC476777
0.55	Remote Similarity	NPC470913
0.549	Remote Similarity	NPC475263
0.5484	Remote Similarity	NPC11242
0.5455	Remote Similarity	NPC603832
0.541	Remote Similarity	NPC470914
0.5366	Remote Similarity	NPC477076
0.5328	Remote Similarity	NPC476776
0.5317	Remote Similarity	NPC25998
0.5238	Remote Similarity	NPC605294
0.5238	Remote Similarity	NPC606553
0.5152	Remote Similarity	NPC329923
0.5152	Remote Similarity	NPC475281
0.5076	Remote Similarity	NPC277212
0.5076	Remote Similarity	NPC30279
0.5076	Remote Similarity	NPC473918
0.5075	Remote Similarity	NPC488308
0.5075	Remote Similarity	NPC485123
0.5038	Remote Similarity	NPC4749
0.5038	Remote Similarity	NPC329828
0.5037	Remote Similarity	NPC312650

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6456
0.1-0.2	2646
0.2-0.3	46
0.3-0.4	1
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