NPASS Compound

Natural Product: NPC278272

Natural Product ID	NPC278272
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Acacioside B
IUPAC Name	(3S,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3-[(E)-3-phenylprop-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Acacioside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446226
PubChem CID	15540912
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 160168 0 0 0 0 0 0 0 0999 V2000 -4.4762 -3.4076 3.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2474 -3.6016 2.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 -3.3012 1.0568 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0848 -2.6864 0.2529 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6966 -3.8637 -0.5326 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8954 -3.3524 -1.3241 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5811 -1.9603 -1.8433 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3742 -0.8923 -1.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7198 -1.2375 -1.0708 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4910 -0.2844 -0.4119 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6229 0.1680 -1.2563 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6776 -0.9335 -1.4429 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7757 -1.8181 -0.2460 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2362 -1.0462 0.9430 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8891 -0.9026 0.7753 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9725 -2.9413 -0.4614 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2969 -1.6948 -2.5512 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3248 1.2242 -0.7177 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5002 2.3190 -1.5100 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.9377 2.7921 -1.5598 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.4333 3.2015 -0.1897 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.4752 4.0437 0.5882 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.0908 3.4480 0.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7918 3.3819 -0.8883 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4469 5.3638 0.1375 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8111 2.0695 0.5497 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9914 3.9067 -2.3839 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2431 -1.7127 -1.8901 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5489 -1.6976 -0.7252 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2909 -0.4282 -0.2336 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9946 -0.1083 -0.0652 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5330 0.7987 -1.2257 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 0.9128 -1.2016 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5407 1.3985 0.1072 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3869 2.8840 0.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0916 0.6832 1.2430 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4553 1.1751 2.5523 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9058 0.7182 2.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6957 1.0148 1.3960 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3944 2.3555 1.6182 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9958 0.9382 0.0967 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8306 1.5588 -0.9628 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1978 0.9745 -0.8840 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6762 0.2688 0.1347 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0646 -0.2283 0.0291 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1805 -1.5527 -0.7036 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6325 -1.5764 -1.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8657 -0.5098 -2.2487 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8731 -2.9126 -1.9209 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5659 -1.4627 -0.0743 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9906 -1.2160 1.2682 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7938 -0.2743 1.3270 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9628 -0.5901 2.5418 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7265 0.2135 2.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8376 -0.0154 1.3596 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3607 -1.4230 1.4368 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7560 -1.9585 2.7003 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3997 1.0629 1.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1439 1.6990 2.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2649 1.6589 0.6340 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5130 -0.4371 -0.3849 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8765 -0.6845 -0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2420 -1.8777 -0.3705 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8242 0.3818 -0.8460 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0994 0.0539 -0.9568 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1684 0.9776 -1.2631 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4781 0.5471 -1.3496 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5259 1.3943 -1.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 16.2860 2.7341 -1.8596 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9829 3.1692 -1.7746 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9213 2.3141 -1.4803 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5885 0.5456 1.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3363 1.7857 1.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9414 -0.4547 2.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3034 -4.2299 -2.3134 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0598 -4.9109 0.2958 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1456 -4.1981 2.9231 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2159 -4.2305 2.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9728 -2.4503 2.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -3.4437 4.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9182 -2.3328 0.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9804 -4.2588 -1.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7251 -3.2466 -0.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9526 -1.9553 -2.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9361 -0.5251 -0.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3570 0.0023 -1.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8596 0.5973 -0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2643 0.3787 -2.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6457 -0.4676 -1.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8409 -2.0970 -0.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3820 -1.7224 1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8093 -0.1200 1.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9934 -3.5296 0.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5389 -2.2518 -2.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0782 2.2449 -2.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6357 2.0397 -1.9375 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3631 3.7841 -0.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8144 4.0486 1.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3280 4.0782 0.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0792 2.4661 0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1486 5.3830 -0.7861 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4384 1.5081 0.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4485 3.6598 -3.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4983 -2.0961 -0.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3921 -1.0480 -0.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9057 0.4115 -2.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9293 1.8186 -1.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3532 -0.1034 -1.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2550 1.5752 -2.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1016 3.3364 -0.5997 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4606 3.3940 1.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6223 3.1347 -0.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2648 -0.3913 1.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0493 0.7004 3.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4012 2.2523 2.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4313 1.1472 3.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8566 -0.3895 2.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8398 3.1830 1.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4031 2.3711 1.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4259 2.6166 2.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9204 -0.1567 -0.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4474 1.4091 -1.9892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9834 2.6539 -0.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8834 1.1357 -1.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6513 0.4956 -0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1152 -2.4356 -0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4686 -1.6282 -1.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5978 -0.8649 -3.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3049 0.4247 -1.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9235 -0.2871 -2.8288 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8893 -3.7513 -1.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9081 -2.8715 -2.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1926 -3.0830 -2.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1940 -2.4018 -0.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6345 -2.1826 1.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7963 -0.8651 1.9458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5895 -0.2856 3.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9382 1.2629 2.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1148 -0.1705 3.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2935 -1.5875 1.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9346 -2.1058 0.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4502 -1.8492 2.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5565 -2.1211 3.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3981 2.6617 0.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5379 1.4013 -0.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3944 -1.0046 -0.8076 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7470 -0.5050 -1.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5590 1.0357 -1.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0996 3.4339 -2.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7557 4.2314 -1.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9371 2.7507 -1.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6572 2.3451 0.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7685 2.4056 2.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2935 1.5370 2.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3575 -1.3683 2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0312 -0.7503 2.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8999 -0.0158 3.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7287 -3.7196 -3.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9175 -5.7531 -0.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4296 -4.6464 2.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 12 17 1 0 11 18 1 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 22 25 1 0 21 26 1 0 20 27 1 0 7 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 1 39 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 47 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 6 53 57 1 0 52 58 1 1 58 59 2 0 58 60 1 0 50 61 1 0 61 62 1 0 62 63 2 0 62 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 67 68 1 0 68 69 2 0 69 70 1 0 70 71 2 0 36 72 1 0 72 73 1 0 72 74 1 0 6 75 1 0 5 76 1 0 2 77 1 0 29 4 1 0 72 31 1 0 15 10 1 0 24 19 1 0 41 34 1 0 55 44 1 0 71 66 1 0 55 39 1 0 52 45 1 0 1 78 1 0 1 79 1 0 1 80 1 0 4 81 1 1 5 82 1 6 6 83 1 1 7 84 1 6 8 85 1 0 8 86 1 0 10 87 1 1 11 88 1 6 12 89 1 6 13 90 1 1 14 91 1 0 14 92 1 0 16 93 1 0 17 94 1 0 19 95 1 6 20 96 1 6 21 97 1 6 22 98 1 1 23 99 1 0 23100 1 0 25101 1 0 26102 1 0 27103 1 0 29104 1 6 31105 1 6 32106 1 0 32107 1 0 33108 1 0 33109 1 0 35110 1 0 35111 1 0 35112 1 0 36113 1 6 37114 1 0 37115 1 0 38116 1 0 38117 1 0 40118 1 0 40119 1 0 40120 1 0 41121 1 6 42122 1 0 42123 1 0 43124 1 0 45125 1 6 46126 1 0 46127 1 0 48128 1 0 48129 1 0 48130 1 0 49131 1 0 49132 1 0 49133 1 0 50134 1 1 51135 1 0 51136 1 0 53137 1 1 54138 1 0 54139 1 0 56140 1 0 56141 1 0 56142 1 0 57143 1 0 60144 1 0 64145 1 0 65146 1 0 67147 1 0 68148 1 0 69149 1 0 70150 1 0 71151 1 0 73152 1 0 73153 1 0 73154 1 0 74155 1 0 74156 1 0 74157 1 0 75158 1 0 76159 1 0 77160 1 0 M END

Standard InCHIKey	ACXXXCPCILHADS-KNCTVXNWSA-N
Standard InCHI	InChI=1S/C57H83NO19/c1-28(59)58-41-45(67)44(66)34(27-73-50-47(43(65)33(61)26-72-50)77-49-46(68)42(64)32(60)25-71-49)74-48(41)76-38-19-20-54(6)35(53(38,4)5)18-21-55(7)36(54)16-15-30-31-22-52(2,3)39(75-40(63)17-14-29-12-10-9-11-13-29)24-57(31,51(69)70)37(62)23-56(30,55)8/h9-15,17,31-39,41-50,60-62,64-68H,16,18-27H2,1-8H3,(H,58,59)(H,69,70)/b17-14+/t31-,32+,33-,34+,35-,36+,37+,38-,39-,41+,42-,43-,44+,45+,46+,47+,48-,49-,50-,54-,55+,56+,57+/m0/s1
SMILES	CC(=N[C@@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)[C@H](C[C@@]4([C@@H](C[C@@]32C)O)C(=O)O)OC(=O)/C=C/c2ccccc2)C1(C)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1085.56	Volume:	1074.339 ? Van der Waals volume.
Dense:	1.01	LogP:	1.893 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.717 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.734 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	54.0
TPSA:	313.41 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.839	Fsp³:	0.772
MCE-18:	254.822 ? 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:	0.969	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.114 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.031 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.024	Promiscuous compounds:	0.023

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.943	MDCK Permeability:	-5.306
Pgp-inhibitor:	0.003	Pgp-substrate:	0.011
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):	0.047
20% Bioavailability (F20%):	0.392	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.01
Plasma Protein Binding (PPB):	72.891%	Volume Distribution (VD):	-0.582
Fu:	21.834% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.109

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-0.076

Half-life (T1/2):

3.237

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.992	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.894	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.025	Skin Sensitization:	1.0
Carcinogencity:	0.045	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.994
Hematotoxicity:	0.494	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.978	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.31	Hek293 Cytotoxicity:	0.353
BCF:	0.431 ? 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:	3.883 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.072 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.987 ? 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
NPO32561	acacia tenuifolia	Species	Fabaceae	Eukaryota	n.a.	suriname rainforest	n.a.	PMID[11858750]

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
IC12	4
IC50	1

Activity Type	# Activity
Cell line	1
Organism	4

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	=	13.5	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	280.0	ug ml-1	PMID[22316191]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	220.0	ug ml-1	PMID[21761866]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	150.0	ug ml-1	DOI[10.6019/CHEMBL1201861]

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 NPC278272 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	16264
0.1-0.2	29339
0.2-0.3	3388
0.3-0.4	678
0.4-0.5	148
0.5-0.6	23
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120667
0.7541	Intermediate Similarity	NPC200788
0.6875	Remote Similarity	NPC243680
0.6774	Remote Similarity	NPC145899
0.672	Remote Similarity	NPC75318
0.6693	Remote Similarity	NPC280941
0.6693	Remote Similarity	NPC235772
0.6667	Remote Similarity	NPC488211
0.6642	Remote Similarity	NPC488212
0.6562	Remote Similarity	NPC210729
0.6562	Remote Similarity	NPC82931
0.6405	Remote Similarity	NPC482013
0.626	Remote Similarity	NPC475119
0.626	Remote Similarity	NPC288205
0.626	Remote Similarity	NPC51465
0.6172	Remote Similarity	NPC488515
0.6015	Remote Similarity	NPC172365
0.5969	Remote Similarity	NPC73829
0.5894	Remote Similarity	NPC40085
0.5817	Remote Similarity	NPC264270
0.5782	Remote Similarity	NPC488210
0.5735	Remote Similarity	NPC473824
0.5734	Remote Similarity	NPC111466
0.5714	Remote Similarity	NPC291903
0.5639	Remote Similarity	NPC37134
0.5462	Remote Similarity	NPC80843
0.5455	Remote Similarity	NPC104400
0.5455	Remote Similarity	NPC10320
0.5448	Remote Similarity	NPC119794
0.5385	Remote Similarity	NPC488516
0.5338	Remote Similarity	NPC232237
0.5323	Remote Similarity	NPC242611
0.5276	Remote Similarity	NPC488618
0.5244	Remote Similarity	NPC488619
0.5234	Remote Similarity	NPC76999
0.5172	Remote Similarity	NPC476113
0.5109	Remote Similarity	NPC484832
0.5089	Remote Similarity	NPC488620
0.5071	Remote Similarity	NPC475486
0.5038	Remote Similarity	NPC488214

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC278272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3993
0.1-0.2	5085
0.2-0.3	69
0.3-0.4	3
0.4-0.5	0
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