NPASS Compound

Natural Product: NPC477193

Natural Product ID	NPC477193
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside C
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-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 C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44140278
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 146152 0 0 0 0 0 0 0 0999 V2000 -10.9239 -1.5644 -2.5136 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2308 -2.6883 -1.8261 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0396 -2.5873 -1.2736 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4014 -3.7488 -0.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3278 -1.3451 -1.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8102 -0.3270 -1.8691 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0547 -1.1666 -0.7444 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3577 0.0454 -0.7847 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3456 0.6709 0.5869 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8845 2.0901 0.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5769 2.2079 -0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1734 1.1883 -1.2979 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0449 -0.0231 -1.4774 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2871 -1.3173 -1.3150 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2899 -1.3614 -0.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2950 -0.2449 -0.1787 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7694 0.7001 -1.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9327 1.1300 -2.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5015 0.7889 -2.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0502 0.5113 -0.8442 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8470 -0.6502 -0.3567 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2625 -1.0288 0.9905 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2208 -1.3159 0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8518 0.0235 0.6283 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4253 0.5001 -0.7217 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8573 1.9845 -0.6776 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3074 2.1802 -0.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0766 1.1493 0.2454 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2865 0.1405 0.9792 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0279 -1.1961 0.8876 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3635 0.4708 2.4872 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0748 0.5535 -0.5550 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3603 0.9704 -0.2167 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2572 -0.1329 0.2687 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6398 0.1651 -0.2017 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7152 0.1705 -1.7296 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5682 0.9855 -2.2223 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8490 1.6650 -1.2910 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7229 0.1837 -3.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4944 0.1770 -3.1191 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3434 -0.5752 -4.1720 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9199 0.6503 -2.1781 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6296 -0.6804 0.2318 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7117 -0.0626 0.8205 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9578 -0.5443 2.2087 C 0 0 1 0 0 0 0 0 0 0 0 0 12.2532 0.0141 2.7687 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3916 -0.2112 1.8091 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9453 0.3665 0.4606 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8571 -0.3612 0.0523 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6147 -1.5764 1.6434 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5676 -0.6236 3.9563 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9569 -0.0983 3.1037 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2569 -0.1238 1.6594 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1848 -0.0851 -1.8663 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7390 -1.8681 -1.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4018 0.3151 1.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2236 -2.3431 -1.0349 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4879 -0.1610 -2.9708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3134 -0.2315 -3.6913 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9772 2.8464 -0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7857 2.7022 1.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7487 0.8031 0.9282 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2680 0.2614 2.0934 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4309 -0.3460 2.8256 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6598 0.3964 2.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1929 -0.1079 3.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3714 -0.8438 4.4907 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5611 1.1223 1.4902 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9695 -1.8748 -2.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3746 -1.1437 -3.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0892 -0.7636 -1.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7041 -3.6805 -1.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5143 -4.0133 -1.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0606 -4.6453 -0.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1022 -3.4621 0.4139 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0361 0.7592 -1.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8159 0.1121 1.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7924 2.4657 0.4604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6548 3.2596 -0.7856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3170 1.7307 -2.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7990 -1.6652 -2.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8567 -2.3793 -0.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9493 -1.4098 0.7346 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3059 1.8282 -2.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0840 1.5483 -2.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 -0.1224 -2.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3995 1.3839 -0.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7185 -1.8975 1.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2968 -0.0871 1.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -2.1336 0.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 -1.5679 1.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2964 0.7261 1.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4951 2.5247 -1.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3348 2.3985 0.2269 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7626 2.2866 -1.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4446 3.2224 -0.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6896 1.7643 0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3428 -2.0621 1.0861 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4949 -1.3603 -0.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7950 -1.2747 1.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5346 -0.0179 3.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3402 1.5821 2.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3336 0.1306 2.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3189 1.7226 0.6322 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8975 -1.1385 -0.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9266 1.2060 0.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6086 -0.8636 -2.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0156 1.7806 -2.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8614 -1.3719 -4.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9454 0.8955 -3.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5468 1.0370 0.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9921 -1.6352 2.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1704 1.1224 2.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3112 0.2609 2.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6773 1.4386 0.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7620 0.2227 -0.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4331 -1.6970 1.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3236 -0.1404 4.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0008 0.8956 3.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5708 0.7728 1.9967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.2893 -2.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9299 0.6147 -2.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7170 -1.0065 -1.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4191 -1.8644 -2.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9004 -2.7574 -0.5579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2620 -2.0267 -1.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1748 -0.5744 1.9112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8449 1.1993 1.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5025 0.3928 1.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4411 -2.8817 -1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9967 -1.1419 -3.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1354 0.6910 -3.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1292 0.5787 -4.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8875 3.9045 -0.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8027 2.8594 -1.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9734 2.4900 -0.0831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2763 3.6872 1.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2409 1.9896 2.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 2.8620 2.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2592 0.0357 3.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5679 -0.2358 4.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0395 -1.2942 5.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9392 -1.7298 3.9358 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6074 1.1515 1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5152 0.5760 0.5249 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1739 2.1616 1.3927 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 6 21 55 1 6 16 56 1 1 14 57 1 0 13 58 1 6 58 59 1 0 10 60 1 0 10 61 1 0 9 62 1 0 62 63 1 0 63 64 2 0 63 65 1 0 65 66 2 0 66 67 1 0 65 68 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 69 1 0 1 70 1 0 1 71 1 0 2 72 1 0 4 73 1 0 4 74 1 0 4 75 1 0 8 76 1 6 9 77 1 1 11 78 1 0 11 79 1 0 12 80 1 6 14 81 1 6 15 82 1 0 15 83 1 0 18 84 1 0 19 85 1 0 19 86 1 0 20 87 1 1 22 88 1 0 22 89 1 0 23 90 1 0 23 91 1 0 24 92 1 1 26 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 28 97 1 1 30 98 1 0 30 99 1 0 30100 1 0 31101 1 0 31102 1 0 31103 1 0 33104 1 1 34105 1 1 35106 1 1 36107 1 6 37108 1 6 41109 1 0 42110 1 0 44111 1 1 45112 1 6 46113 1 1 47114 1 1 48115 1 0 48116 1 0 50117 1 0 51118 1 0 52119 1 0 53120 1 0 54121 1 0 54122 1 0 54123 1 0 55124 1 0 55125 1 0 55126 1 0 56127 1 0 56128 1 0 56129 1 0 57130 1 0 58131 1 0 58132 1 0 59133 1 0 60134 1 0 60135 1 0 60136 1 0 61137 1 0 61138 1 0 61139 1 0 66140 1 0 67141 1 0 67142 1 0 67143 1 0 68144 1 0 68145 1 0 68146 1 0 M END

Standard InCHIKey	QVFHHHDKLVZEKJ-SAWIQVRLSA-N
Standard InCHI	InChI=1S/C51H78O17/c1-12-24(3)42(61)67-39-40(68-43(62)25(4)13-2)51(23-52)27(20-46(39,5)6)26-14-15-30-48(9)18-17-32(47(7,8)29(48)16-19-49(30,10)50(26,11)21-31(51)54)64-45-36(58)37(35(57)38(66-45)41(59)60)65-44-34(56)33(55)28(53)22-63-44/h12-14,27-40,44-45,52-58H,15-23H2,1-11H3,(H,59,60)/b24-12-,25-13-/t27-,28-,29-,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,48-,49+,50+,51-/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)O)CO)(C)C)OC(=O)/C(=C\C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	962.52	Volume:	964.372 ? Van der Waals volume.
Dense:	0.998	LogP:	2.819 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.943 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.989 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	43.0
TPSA:	268.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.067	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.515	Fsp³:	0.824
MCE-18:	161.355 ? 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:	0.94	Fluc inhibitor:	0.006 ? 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:	0.179	Promiscuous compounds:	0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.9	MDCK Permeability:	-5.209
Pgp-inhibitor:	0.0	Pgp-substrate:	0.086
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):	0.004
20% Bioavailability (F20%):	0.812	30% Bioavailability (F30%):	0.825
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.987
Plasma Protein Binding (PPB):	79.012%	Volume Distribution (VD):	-0.567
Fu:	14.734% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.138	BCRP inhibitor:	0.001
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.03	CYP3A4-substrate:	0.878
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.029
HLM stability:	0.724 ? 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):

0.219

Half-life (T1/2):

2.373

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.531	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.898	Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.109	Skin Sensitization:	1.0
Carcinogencity:	0.557	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.207
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.966
Hematotoxicity:	0.816	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.955	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.946	Hek293 Cytotoxicity:	0.672
BCF:	0.339 ? 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:	3.626 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.693 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.673 ? 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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	400	nM	PMID[20560647]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	700	nM	PMID[20560647]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	1200	nM	PMID[20560647]
NPT81	Cell line	A549	Homo sapiens	IC50	=	1800	nM	PMID[20560647]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	2500	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 NPC477193 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	20646
0.1-0.2	25147
0.2-0.3	3067
0.3-0.4	632
0.4-0.5	283
0.5-0.6	48
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC477191
0.9	High Similarity	NPC477195
0.8911	High Similarity	NPC477196
0.8173	Intermediate Similarity	NPC477194
0.7658	Intermediate Similarity	NPC602995
0.757	Intermediate Similarity	NPC477192
0.7522	Intermediate Similarity	NPC478597
0.7431	Intermediate Similarity	NPC477197
0.7391	Intermediate Similarity	NPC478596
0.7328	Intermediate Similarity	NPC271610
0.7054	Intermediate Similarity	NPC25998
0.6964	Remote Similarity	NPC11242
0.6807	Remote Similarity	NPC476780
0.6667	Remote Similarity	NPC488308
0.6639	Remote Similarity	NPC329828
0.6639	Remote Similarity	NPC476777
0.6612	Remote Similarity	NPC312650
0.6518	Remote Similarity	NPC603832
0.6496	Remote Similarity	NPC478600
0.6496	Remote Similarity	NPC478599
0.6481	Remote Similarity	NPC6377
0.6481	Remote Similarity	NPC208381
0.6446	Remote Similarity	NPC470518
0.6393	Remote Similarity	NPC265841
0.6364	Remote Similarity	NPC4749
0.6349	Remote Similarity	NPC488309
0.623	Remote Similarity	NPC192765
0.6179	Remote Similarity	NPC178264
0.6179	Remote Similarity	NPC478598
0.605	Remote Similarity	NPC107536
0.605	Remote Similarity	NPC280029
0.605	Remote Similarity	NPC9470
0.5984	Remote Similarity	NPC110700
0.5968	Remote Similarity	NPC82380
0.5968	Remote Similarity	NPC244296
0.595	Remote Similarity	NPC478155
0.595	Remote Similarity	NPC478154
0.592	Remote Similarity	NPC21691
0.5906	Remote Similarity	NPC484833
0.5882	Remote Similarity	NPC329976
0.5868	Remote Similarity	NPC609119
0.5862	Remote Similarity	NPC611191
0.58	Remote Similarity	NPC473160
0.5798	Remote Similarity	NPC477077
0.5781	Remote Similarity	NPC476779
0.5748	Remote Similarity	NPC476774
0.569	Remote Similarity	NPC159309
0.569	Remote Similarity	NPC86222
0.5625	Remote Similarity	NPC603870
0.5573	Remote Similarity	NPC302543
0.5538	Remote Similarity	NPC484059
0.5538	Remote Similarity	NPC484060
0.553	Remote Similarity	NPC476775
0.5512	Remote Similarity	NPC46823
0.55	Remote Similarity	NPC114484
0.5469	Remote Similarity	NPC71391
0.5433	Remote Similarity	NPC283417
0.5433	Remote Similarity	NPC200049
0.5391	Remote Similarity	NPC114441
0.5333	Remote Similarity	NPC476778
0.531	Remote Similarity	NPC1046
0.5294	Remote Similarity	NPC476776
0.5285	Remote Similarity	NPC477078
0.5278	Remote Similarity	NPC283849
0.5273	Remote Similarity	NPC242611
0.5179	Remote Similarity	NPC480937
0.5167	Remote Similarity	NPC232237
0.5164	Remote Similarity	NPC64715
0.5124	Remote Similarity	NPC105800
0.512	Remote Similarity	NPC187290
0.5083	Remote Similarity	NPC605226
0.5081	Remote Similarity	NPC301449
0.5081	Remote Similarity	NPC477076
0.5081	Remote Similarity	NPC601290
0.5079	Remote Similarity	NPC605294
0.5041	Remote Similarity	NPC44716
0.5039	Remote Similarity	NPC284449
0.5039	Remote Similarity	NPC472267
0.5039	Remote Similarity	NPC115656
0.5038	Remote Similarity	NPC485123

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6526
0.1-0.2	2576
0.2-0.3	44
0.3-0.4	3
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
0.5575	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