NPASS Compound

Natural Product: NPC477191

Natural Product ID	NPC477191
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,23,28-trihydroxy-21beta,22alpha-bis(angeloyloxy)oleana-12-ene
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-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
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44140277
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 147153 0 0 0 0 0 0 0 0999 V2000 -6.2297 -4.9608 -0.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2828 -4.9755 -1.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8732 -3.9236 -1.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9344 -4.1668 -2.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5686 -2.5744 -1.3789 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2426 -1.6285 -1.9043 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6467 -2.0911 -0.5091 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4163 -0.7434 -0.1625 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8688 -0.3991 1.2245 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8116 -0.1916 2.2434 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4143 -0.0757 1.7586 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3695 0.6198 0.4018 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1556 -0.1204 -0.6308 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3597 -1.1747 -1.3468 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0137 -0.7701 -1.8412 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1753 -0.0198 -0.8772 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9571 0.9017 0.0004 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4359 2.0059 0.4870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0626 2.5288 0.2550 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3074 1.4172 -0.4110 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0756 0.7912 -1.5346 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2161 -0.0403 -2.4394 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2275 -0.1205 -2.2110 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7673 0.3622 -0.9168 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1402 1.7178 -0.6802 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6538 2.3579 0.5982 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1332 2.4546 0.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8536 1.1626 0.2586 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2351 0.2787 -0.7501 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8892 0.4382 -2.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5957 -1.1455 -0.2810 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2285 -2.1299 -1.1457 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1450 1.5097 -0.1257 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0987 1.2474 0.8473 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0949 0.2083 0.4413 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5178 0.7438 0.4894 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5279 2.1384 -0.0956 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5825 3.0678 0.6189 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6233 2.4173 1.3171 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1296 4.1617 -0.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9286 4.4613 -0.3242 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0547 4.8541 -1.0079 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7870 2.7018 -0.0981 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3363 -0.0584 -0.2567 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3993 -0.5944 0.4600 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4202 -2.0827 0.5357 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8317 -2.5341 0.8488 C 0 0 2 0 0 0 0 0 0 0 0 0 12.6875 -2.1532 -0.3460 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2250 -0.8231 -0.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6118 -0.0363 0.0344 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4869 -3.1190 -1.3273 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8543 -3.9137 1.0793 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6364 -2.5028 1.6109 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0246 -0.8620 1.3291 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3475 2.6873 -1.7742 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7574 1.8322 -2.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5342 -1.1174 0.0169 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3510 -2.3880 -0.6660 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4358 0.9233 -1.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0446 0.3229 -2.8305 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8042 -1.3036 3.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1167 1.0752 3.0622 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7573 0.6992 1.2705 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0631 0.5672 1.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4458 -0.5919 2.0979 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9948 1.6781 1.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2183 1.4783 2.2174 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7236 0.1556 2.6750 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5353 3.0161 1.3307 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2524 -5.9408 0.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2496 -4.9422 -0.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2749 -4.1104 0.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5955 -5.9573 -1.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8948 -4.4580 -2.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6395 -4.9514 -3.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1381 -3.2189 -3.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2183 -0.2250 -0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4869 -1.2678 1.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8492 -1.0271 1.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8845 0.5494 2.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8665 1.5849 0.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9758 -1.4023 -2.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -1.7862 -2.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0993 -0.3634 -2.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0301 2.6662 1.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0211 3.5021 -0.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5370 2.6958 1.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2398 0.6264 0.4017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6775 -1.0721 -2.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3639 0.2741 -3.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5411 -1.1935 -2.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8471 0.3831 -3.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3482 -0.3079 -0.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2383 3.3901 0.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3552 1.7471 1.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5263 3.2268 -0.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4633 2.8150 1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9538 0.6803 1.2765 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9858 0.4576 -1.9464 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6247 1.3948 -2.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6952 -0.4371 -2.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0264 -1.3350 0.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6553 -1.2200 0.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5842 -2.7799 -0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5173 0.8048 1.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8349 -0.1504 -0.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8138 0.8545 1.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1915 2.1278 -1.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2359 3.5780 1.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7321 5.5002 -1.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2917 2.5911 0.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2770 -0.2029 1.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1336 -2.5891 -0.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1972 -1.9850 1.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7450 -2.0909 -0.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5724 -0.9936 -1.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1440 -0.2817 -1.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3348 -3.2862 -1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0449 -4.1455 2.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1688 -2.4173 2.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1346 -1.6869 0.8218 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6036 3.5115 -1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3290 3.2160 -1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2777 2.3127 -2.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3775 2.5602 -1.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0464 2.4741 -2.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4709 1.4012 -3.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4445 -0.8050 1.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2253 -2.0026 0.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6251 -1.5337 -0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9012 -3.0468 -1.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2136 1.5901 -1.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5295 1.4794 -1.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4743 0.3940 -3.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8706 -1.6129 3.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2318 -2.1796 2.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4474 -0.9453 4.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2441 1.4264 3.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9576 0.8032 3.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5393 1.8209 2.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8861 2.3610 2.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7555 -0.5999 1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7849 0.2960 3.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1927 -0.2261 3.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0090 3.5084 2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8511 2.8795 0.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4194 3.6419 1.0838 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 1 0 28 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 40 41 2 0 40 42 1 0 37 43 1 0 36 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 46 53 1 0 35 54 1 0 25 55 1 6 21 56 1 6 16 57 1 1 14 58 1 0 13 59 1 6 59 60 1 0 10 61 1 0 10 62 1 0 9 63 1 0 63 64 1 0 64 65 2 0 64 66 1 0 66 67 2 0 67 68 1 0 66 69 1 0 13 8 1 0 17 12 1 0 21 16 1 0 25 20 1 0 29 24 1 0 39 34 1 0 50 45 1 0 1 70 1 0 1 71 1 0 1 72 1 0 2 73 1 0 4 74 1 0 4 75 1 0 4 76 1 0 8 77 1 6 9 78 1 1 11 79 1 0 11 80 1 0 12 81 1 1 14 82 1 6 15 83 1 0 15 84 1 0 18 85 1 0 19 86 1 0 19 87 1 0 20 88 1 1 22 89 1 0 22 90 1 0 23 91 1 0 23 92 1 0 24 93 1 1 26 94 1 0 26 95 1 0 27 96 1 0 27 97 1 0 28 98 1 1 30 99 1 0 30100 1 0 30101 1 0 31102 1 0 31103 1 0 32104 1 0 34105 1 1 35106 1 6 36107 1 1 37108 1 6 38109 1 1 42110 1 0 43111 1 0 45112 1 1 46113 1 6 47114 1 1 48115 1 1 49116 1 0 49117 1 0 51118 1 0 52119 1 0 53120 1 0 54121 1 0 55122 1 0 55123 1 0 55124 1 0 56125 1 0 56126 1 0 56127 1 0 57128 1 0 57129 1 0 57130 1 0 58131 1 0 59132 1 0 59133 1 0 60134 1 0 61135 1 0 61136 1 0 61137 1 0 62138 1 0 62139 1 0 62140 1 0 67141 1 0 68142 1 0 68143 1 0 68144 1 0 69145 1 0 69146 1 0 69147 1 0 M END

Standard InCHIKey	WGPUVZRQQKVFDP-NFNBLRENSA-N
Standard InCHI	InChI=1S/C51H78O18/c1-11-24(3)42(62)68-39-40(69-43(63)25(4)12-2)51(23-53)27(19-46(39,5)6)26-13-14-30-47(7)17-16-32(48(8,22-52)29(47)15-18-49(30,9)50(26,10)20-31(51)55)65-45-36(59)37(35(58)38(67-45)41(60)61)66-44-34(57)33(56)28(54)21-64-44/h11-13,27-40,44-45,52-59H,14-23H2,1-10H3,(H,60,61)/b24-11-,25-12-/t27-,28-,29+,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,47-,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]([C@@]5(C)CO)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:	978.52	Volume:	973.162 ? Van der Waals volume.
Dense:	1.006	LogP:	2.098 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.432 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.413 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	43.0
TPSA:	288.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.614	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:	0.899	Fluc inhibitor:	0.004 ? 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:	0.184	Promiscuous compounds:	0.163

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.03	MDCK Permeability:	-5.201
Pgp-inhibitor:	0.0	Pgp-substrate:	0.077
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%):	0.655	30% Bioavailability (F30%):	0.322
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067	MRP1:	0.971
Plasma Protein Binding (PPB):	77.696%	Volume Distribution (VD):	-0.53
Fu:	15.839% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.002	BCRP inhibitor:	0.006
BSEP inhibitor:	0.017

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.124
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.266 ? 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):

0.188

Half-life (T1/2):

2.315

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.515	Drug-induced Liver Injury (DILI):	0.95
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.055	Skin Sensitization:	1.0
Carcinogencity:	0.579	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.145
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.972
Hematotoxicity:	0.851	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.93	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.945	Hek293 Cytotoxicity:	0.631
BCF:	0.31 ? 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:	3.557 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.625 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.527 ? 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
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	4700	nM	PMID[20560647]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	5500	nM	PMID[20560647]
NPT180	Cell line	HCT-8	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]

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 NPC477191 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	20362
0.1-0.2	25221
0.2-0.3	3341
0.3-0.4	666
0.4-0.5	191
0.5-0.6	42
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC477193
0.9091	High Similarity	NPC477195
0.9	High Similarity	NPC477196
0.8155	Intermediate Similarity	NPC477192
0.8073	Intermediate Similarity	NPC478597
0.7928	Intermediate Similarity	NPC478596
0.757	Intermediate Similarity	NPC477194
0.75	Intermediate Similarity	NPC477197
0.7304	Intermediate Similarity	NPC476780
0.7105	Intermediate Similarity	NPC602995
0.7037	Intermediate Similarity	NPC603832
0.6991	Remote Similarity	NPC478600
0.6991	Remote Similarity	NPC478599
0.6807	Remote Similarity	NPC271610
0.6694	Remote Similarity	NPC476777
0.6639	Remote Similarity	NPC478598
0.6522	Remote Similarity	NPC25998
0.6522	Remote Similarity	NPC107536
0.6522	Remote Similarity	NPC280029
0.6522	Remote Similarity	NPC9470
0.6435	Remote Similarity	NPC11242
0.6417	Remote Similarity	NPC82380
0.6417	Remote Similarity	NPC244296
0.6339	Remote Similarity	NPC611191
0.6179	Remote Similarity	NPC488308
0.6179	Remote Similarity	NPC476774
0.6148	Remote Similarity	NPC329828
0.6134	Remote Similarity	NPC478155
0.6129	Remote Similarity	NPC312650
0.6111	Remote Similarity	NPC603870
0.6032	Remote Similarity	NPC110700
0.6	Remote Similarity	NPC478154
0.5968	Remote Similarity	NPC470518
0.5946	Remote Similarity	NPC6377
0.5946	Remote Similarity	NPC208381
0.5938	Remote Similarity	NPC476775
0.592	Remote Similarity	NPC265841
0.5891	Remote Similarity	NPC488309
0.5887	Remote Similarity	NPC4749
0.5859	Remote Similarity	NPC473160
0.5827	Remote Similarity	NPC476779
0.576	Remote Similarity	NPC192765
0.5714	Remote Similarity	NPC178264
0.5469	Remote Similarity	NPC21691
0.5462	Remote Similarity	NPC484833
0.5447	Remote Similarity	NPC472267
0.5447	Remote Similarity	NPC115656
0.541	Remote Similarity	NPC329976
0.5403	Remote Similarity	NPC609119
0.5379	Remote Similarity	NPC11577
0.5379	Remote Similarity	NPC141600
0.5373	Remote Similarity	NPC476778
0.537	Remote Similarity	NPC224121
0.5333	Remote Similarity	NPC476776
0.5328	Remote Similarity	NPC477077
0.5327	Remote Similarity	NPC28198
0.5327	Remote Similarity	NPC476123
0.5312	Remote Similarity	NPC252289
0.5312	Remote Similarity	NPC305793
0.5278	Remote Similarity	NPC177246
0.521	Remote Similarity	NPC159309
0.521	Remote Similarity	NPC86222
0.5149	Remote Similarity	NPC302543
0.5116	Remote Similarity	NPC269484
0.5116	Remote Similarity	NPC97918
0.5113	Remote Similarity	NPC484059
0.5113	Remote Similarity	NPC484060
0.5079	Remote Similarity	NPC478152
0.5078	Remote Similarity	NPC284449
0.5077	Remote Similarity	NPC46823
0.5041	Remote Similarity	NPC114484
0.5039	Remote Similarity	NPC252657
0.5039	Remote Similarity	NPC88311
0.5038	Remote Similarity	NPC71391

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6435
0.1-0.2	2664
0.2-0.3	48
0.3-0.4	2
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
0.5086	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