NPASS Compound

Natural Product: NPC166422

Natural Product ID	NPC166422
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl Oleanolic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2430029
PubChem CID	73346237
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 156164 0 0 0 0 0 0 0 0999 V2000 -1.3981 2.8143 3.3594 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6788 1.9927 3.3115 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7911 2.8875 2.8115 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1105 2.1478 2.8194 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8628 0.7402 2.3315 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5533 0.6951 1.5875 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4994 0.9774 2.4076 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3254 -0.5223 0.9397 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2466 -0.3593 -0.4317 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5031 -1.0559 -1.0201 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1617 -1.9657 -2.1587 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0967 -1.4874 -3.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1958 -0.6858 -2.4456 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0944 -1.0445 -1.0448 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8237 -0.7299 -0.6709 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0286 -1.8331 -0.5976 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0524 -1.7792 -1.7210 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0229 -0.6576 -1.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5252 -0.4194 -0.1806 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8252 0.8121 0.2748 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -1.6871 0.5182 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0499 -1.9978 1.7334 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4907 -1.9012 1.2870 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8379 -0.4719 0.8592 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5343 0.4112 2.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0227 -0.2685 -0.3505 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3034 0.8948 -1.1825 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6660 1.3633 -0.9619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6235 0.8683 -0.2062 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9034 1.5868 -0.2036 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9360 1.1070 -1.1725 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0107 2.1779 -1.2626 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5586 3.4377 -1.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1655 1.5638 -2.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5767 2.3831 0.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9722 1.4393 1.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4960 1.7336 1.1631 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7298 0.9628 2.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2367 -0.3770 1.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3189 -0.3653 0.5696 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6730 -1.6297 -0.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4145 3.1729 1.6270 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8765 4.0070 0.8613 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9159 3.5566 2.8509 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7702 -2.0423 0.6637 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8048 -3.5877 0.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1307 -1.5490 1.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3407 -2.0428 -2.9450 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7867 -3.3423 -2.9620 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2071 -3.4291 -2.4007 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5843 -4.8784 -2.2404 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1806 -5.7452 -3.4000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9336 -5.2738 -4.1049 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8952 -5.9378 -5.4662 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9784 -5.5225 -6.2586 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8722 -3.8906 -4.2471 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9853 -7.0393 -2.9233 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9819 -4.9599 -2.1444 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3311 -2.8064 -1.1739 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4032 -0.0850 -1.4781 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9071 0.3097 1.5333 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 2.7370 2.0015 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1783 3.1493 2.6587 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3136 4.6668 2.6849 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4079 5.1127 1.7340 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5213 4.2012 0.5484 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5329 2.7511 0.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3627 2.5633 2.2446 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6282 4.5044 -0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2140 6.4180 1.3234 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6391 5.1386 3.9515 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8396 3.9923 3.6971 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5219 3.7556 3.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0302 2.8960 2.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6528 2.1488 3.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9428 1.5908 4.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5521 3.2056 1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4931 2.1333 3.8788 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8460 0.0801 3.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6088 1.4662 0.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3215 0.7310 -0.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0295 -1.6442 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9690 -3.0126 -1.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5281 -0.8867 -3.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4999 -2.3398 -3.5245 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3060 -2.1546 -1.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6280 -2.7112 -0.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4380 -1.5945 -2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4868 -2.7694 -1.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5593 0.2548 -2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8578 -0.9170 -2.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5638 1.5465 0.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3342 1.3905 -0.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9835 0.6508 0.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6144 -2.4798 -0.2128 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7909 -1.5403 2.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9054 -3.1113 1.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4941 -2.5410 0.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1059 -2.2746 2.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1315 0.0451 2.9127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4963 0.3184 2.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6732 1.4821 1.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2565 -1.1927 -0.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6271 1.7731 -1.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1805 0.5976 -2.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9367 2.2943 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7533 2.6625 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5247 0.2275 -0.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5436 1.0092 -2.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6254 4.3040 -1.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1925 3.6256 -2.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5339 3.2899 -2.3132 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9098 2.3723 -2.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6431 0.7450 -1.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8000 1.1795 -3.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2484 3.4174 0.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6677 2.3832 0.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3723 1.7715 2.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2527 0.3986 1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9286 1.5898 2.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4340 0.7600 3.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8743 -0.9061 2.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1955 -0.9550 1.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5080 -2.4676 0.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1825 -1.7216 -1.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7586 -1.6823 -0.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5788 4.4174 3.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6541 -4.0198 0.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9772 -3.8407 1.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1126 -4.0423 0.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8080 -1.0492 2.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3417 -2.3634 2.5403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7170 -0.8591 1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1669 -4.0398 -2.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9155 -2.9855 -3.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1836 -5.3317 -1.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0414 -5.8268 -4.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0637 -5.6696 -3.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9714 -7.0339 -5.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9301 -5.7264 -5.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3561 -4.6981 -5.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2495 -7.0952 -2.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2802 -5.2650 -1.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9710 -3.3322 -0.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0330 0.3758 -2.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6203 -0.1312 2.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0436 2.8699 3.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3669 5.1184 2.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3735 5.0666 2.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6219 4.3846 -0.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7223 2.1780 0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5248 2.3036 0.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4233 4.2032 -1.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0381 6.9197 1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4500 5.6705 3.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2388 4.7010 3.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 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 6 37 42 1 1 42 43 2 0 42 44 1 0 21 45 1 0 45 46 1 0 45 47 1 0 11 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 51 58 1 0 50 59 1 0 10 60 1 0 5 61 1 0 4 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 66 69 1 0 65 70 1 0 64 71 1 0 3 72 1 0 7 2 1 0 14 9 1 0 45 16 1 0 56 49 1 0 68 63 1 0 26 19 1 0 40 29 1 0 40 24 1 0 37 30 1 0 1 73 1 0 1 74 1 0 1 75 1 0 2 76 1 1 3 77 1 6 4 78 1 1 5 79 1 1 6 80 1 6 9 81 1 1 10 82 1 1 11 83 1 1 12 84 1 0 12 85 1 0 14 86 1 6 16 87 1 6 17 88 1 0 17 89 1 0 18 90 1 0 18 91 1 0 20 92 1 0 20 93 1 0 20 94 1 0 21 95 1 6 22 96 1 0 22 97 1 0 23 98 1 0 23 99 1 0 25100 1 0 25101 1 0 25102 1 0 26103 1 6 27104 1 0 27105 1 0 28106 1 0 30107 1 6 31108 1 0 31109 1 0 33110 1 0 33111 1 0 33112 1 0 34113 1 0 34114 1 0 34115 1 0 35116 1 0 35117 1 0 36118 1 0 36119 1 0 38120 1 0 38121 1 0 39122 1 0 39123 1 0 41124 1 0 41125 1 0 41126 1 0 44127 1 0 46128 1 0 46129 1 0 46130 1 0 47131 1 0 47132 1 0 47133 1 0 49134 1 1 50135 1 6 51136 1 1 52137 1 6 53138 1 1 54139 1 0 54140 1 0 55141 1 0 57142 1 0 58143 1 0 59144 1 0 60145 1 0 61146 1 0 63147 1 1 64148 1 6 65149 1 1 66150 1 6 67151 1 0 67152 1 0 69153 1 0 70154 1 0 71155 1 0 72156 1 0 M END

Standard InCHIKey	YMUVECXYJPPWBW-ZQPXAOBSSA-N
Standard InCHI	InChI=1S/C52H84O20/c1-23-32(55)40(71-42-37(60)33(56)26(54)21-65-42)39(62)44(67-23)72-41-35(58)28(69-43-38(61)36(59)34(57)27(20-53)68-43)22-66-45(41)70-31-12-13-49(6)29(48(31,4)5)11-14-51(8)30(49)10-9-24-25-19-47(2,3)15-17-52(25,46(63)64)18-16-50(24,51)7/h9,23,25-45,53-62H,10-22H2,1-8H3,(H,63,64)/t23-,25-,26+,27+,28-,29-,30+,31-,32-,33-,34+,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,49-,50+,51+,52-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1028.56	Volume:	1001.471 ? Van der Waals volume.
Dense:	1.027	LogP:	1.474 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.214 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.259 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	51.0
TPSA:	313.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	9.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.107	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.638	Fsp³:	0.942
MCE-18:	192.653 ? 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:	0.894	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.233	Promiscuous compounds:	0.144

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.287	MDCK Permeability:	-5.232
Pgp-inhibitor:	0.0	Pgp-substrate:	0.032
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):	0.155
20% Bioavailability (F20%):	0.128	30% Bioavailability (F30%):	0.973
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.015
Plasma Protein Binding (PPB):	71.481%	Volume Distribution (VD):	-0.429
Fu:	20.021% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

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:	0.995	CYP3A4-substrate:	0.443
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.002 ? 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):

-0.389

Half-life (T1/2):

3.95

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.772	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.06	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.535	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.048	RPMI-8226 Immunitoxicity:	0.153
A549 Cytotoxicity:	0.626	Hek293 Cytotoxicity:	0.395
BCF:	1.332 ? 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:	3.81 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.449 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.533 ? 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
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23992864]
NPO32682	anemone taipaiensis	Species	Ranunculaceae	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	4
Non-molecular	1

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	7560.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	8320.0	nM	PMID[23398362]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	2370.0	nM	PMID[22061825]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	5230.0	nM	PMID[22365754]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2250.0	nM	PMID[23992864]

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 NPC166422 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	24437
0.1-0.2	21350
0.2-0.3	2690
0.3-0.4	707
0.4-0.5	455
0.5-0.6	120
0.6-0.7	48
0.7-0.8	0
0.8-0.85	4
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9327	High Similarity	NPC323341
0.8716	High Similarity	NPC54636
0.8704	High Similarity	NPC219180
0.8661	High Similarity	NPC471385
0.8654	High Similarity	NPC324875
0.8654	High Similarity	NPC292677
0.8611	High Similarity	NPC471384
0.8544	High Similarity	NPC257468
0.8365	Intermediate Similarity	NPC481082
0.8365	Intermediate Similarity	NPC164419
0.8037	Intermediate Similarity	NPC276093
0.8036	Intermediate Similarity	NPC251263
0.7925	Intermediate Similarity	NPC139044
0.789	Intermediate Similarity	NPC488564
0.7712	Intermediate Similarity	NPC161717
0.7692	Intermediate Similarity	NPC127056
0.7636	Intermediate Similarity	NPC323359
0.7619	Intermediate Similarity	NPC488561
0.757	Intermediate Similarity	NPC114304
0.75	Intermediate Similarity	NPC104400
0.75	Intermediate Similarity	NPC475486
0.75	Intermediate Similarity	NPC10320
0.7478	Intermediate Similarity	NPC133818
0.7297	Intermediate Similarity	NPC79718
0.7273	Intermediate Similarity	NPC471383
0.7264	Intermediate Similarity	NPC56713
0.7143	Intermediate Similarity	NPC164194
0.7103	Intermediate Similarity	NPC25605
0.7103	Intermediate Similarity	NPC59804
0.7027	Intermediate Similarity	NPC180550
0.7027	Intermediate Similarity	NPC35405
0.6972	Remote Similarity	NPC472949
0.6923	Remote Similarity	NPC476992
0.6863	Remote Similarity	NPC283849
0.6863	Remote Similarity	NPC606107
0.6847	Remote Similarity	NPC469945
0.6822	Remote Similarity	NPC270667
0.6789	Remote Similarity	NPC174679
0.6789	Remote Similarity	NPC279554
0.678	Remote Similarity	NPC288205
0.678	Remote Similarity	NPC51465
0.6697	Remote Similarity	NPC136877
0.6696	Remote Similarity	NPC119794
0.6695	Remote Similarity	NPC280941
0.6695	Remote Similarity	NPC235772
0.6667	Remote Similarity	NPC6377
0.6667	Remote Similarity	NPC208381
0.6607	Remote Similarity	NPC80843
0.6589	Remote Similarity	NPC250247
0.6577	Remote Similarity	NPC109079
0.6557	Remote Similarity	NPC123199
0.6552	Remote Similarity	NPC488515
0.6545	Remote Similarity	NPC12288
0.6525	Remote Similarity	NPC488209
0.6504	Remote Similarity	NPC475140
0.6471	Remote Similarity	NPC481078
0.6466	Remote Similarity	NPC73829
0.646	Remote Similarity	NPC22956
0.6406	Remote Similarity	NPC136768
0.6393	Remote Similarity	NPC79643
0.6381	Remote Similarity	NPC28198
0.6381	Remote Similarity	NPC476123
0.6311	Remote Similarity	NPC473824
0.6286	Remote Similarity	NPC204407
0.6283	Remote Similarity	NPC114441
0.6228	Remote Similarity	NPC488516
0.6202	Remote Similarity	NPC43550
0.6148	Remote Similarity	NPC62725
0.6129	Remote Similarity	NPC151543
0.6111	Remote Similarity	NPC191827
0.6098	Remote Similarity	NPC475119
0.6071	Remote Similarity	NPC40085
0.6055	Remote Similarity	NPC100383
0.6048	Remote Similarity	NPC610204
0.6033	Remote Similarity	NPC291903
0.6015	Remote Similarity	NPC488212
0.6	Remote Similarity	NPC41061
0.6	Remote Similarity	NPC227551
0.6	Remote Similarity	NPC484832
0.595	Remote Similarity	NPC37134
0.5935	Remote Similarity	NPC609281
0.592	Remote Similarity	NPC475287
0.5917	Remote Similarity	NPC275668
0.5917	Remote Similarity	NPC475504
0.5909	Remote Similarity	NPC236638
0.5909	Remote Similarity	NPC294453
0.5909	Remote Similarity	NPC305981
0.5909	Remote Similarity	NPC481081
0.5909	Remote Similarity	NPC242611
0.5902	Remote Similarity	NPC606145
0.5891	Remote Similarity	NPC481080
0.5874	Remote Similarity	NPC264270
0.5865	Remote Similarity	NPC261506
0.5865	Remote Similarity	NPC4328
0.5833	Remote Similarity	NPC293330
0.5833	Remote Similarity	NPC258885
0.5833	Remote Similarity	NPC65105
0.5818	Remote Similarity	NPC31839
0.5802	Remote Similarity	NPC110633
0.5798	Remote Similarity	NPC204392
0.5789	Remote Similarity	NPC111466
0.5778	Remote Similarity	NPC220160
0.5752	Remote Similarity	NPC191410
0.5726	Remote Similarity	NPC480424
0.5714	Remote Similarity	NPC185466
0.5669	Remote Similarity	NPC610461
0.5664	Remote Similarity	NPC284807
0.5656	Remote Similarity	NPC123796
0.5645	Remote Similarity	NPC301449
0.5645	Remote Similarity	NPC481079
0.5645	Remote Similarity	NPC75318
0.5645	Remote Similarity	NPC601290
0.5635	Remote Similarity	NPC606553
0.563	Remote Similarity	NPC302543
0.561	Remote Similarity	NPC471435
0.561	Remote Similarity	NPC471434
0.5574	Remote Similarity	NPC63159
0.5556	Remote Similarity	NPC202828
0.5556	Remote Similarity	NPC119592
0.5547	Remote Similarity	NPC607904
0.5538	Remote Similarity	NPC603137
0.5536	Remote Similarity	NPC286347
0.553	Remote Similarity	NPC4749
0.5515	Remote Similarity	NPC298034
0.5515	Remote Similarity	NPC71065
0.5512	Remote Similarity	NPC480939
0.55	Remote Similarity	NPC213674
0.55	Remote Similarity	NPC469946
0.5492	Remote Similarity	NPC473383
0.5462	Remote Similarity	NPC470911
0.5455	Remote Similarity	NPC112352
0.5447	Remote Similarity	NPC91838
0.5433	Remote Similarity	NPC207738
0.5431	Remote Similarity	NPC475472
0.5414	Remote Similarity	NPC488211
0.5391	Remote Similarity	NPC75287
0.5385	Remote Similarity	NPC211798
0.5379	Remote Similarity	NPC283417
0.5379	Remote Similarity	NPC470218
0.5379	Remote Similarity	NPC200049
0.5373	Remote Similarity	NPC21691
0.5372	Remote Similarity	NPC263756
0.5366	Remote Similarity	NPC173859
0.5366	Remote Similarity	NPC148603
0.5352	Remote Similarity	NPC33012
0.5344	Remote Similarity	NPC243680
0.5328	Remote Similarity	NPC240734
0.5317	Remote Similarity	NPC78034
0.5312	Remote Similarity	NPC187290
0.5303	Remote Similarity	NPC135904
0.5303	Remote Similarity	NPC609305
0.5289	Remote Similarity	NPC470512
0.5285	Remote Similarity	NPC309714
0.5282	Remote Similarity	NPC8524
0.528	Remote Similarity	NPC297263
0.5271	Remote Similarity	NPC11242
0.5259	Remote Similarity	NPC57484
0.5254	Remote Similarity	NPC127853
0.5252	Remote Similarity	NPC70809
0.525	Remote Similarity	NPC475296
0.5242	Remote Similarity	NPC251768
0.5234	Remote Similarity	NPC187618
0.5221	Remote Similarity	NPC265841
0.5221	Remote Similarity	NPC488308
0.5191	Remote Similarity	NPC200788
0.5182	Remote Similarity	NPC312650
0.5182	Remote Similarity	NPC258617
0.5175	Remote Similarity	NPC177246
0.5161	Remote Similarity	NPC124296
0.5161	Remote Similarity	NPC30289
0.5159	Remote Similarity	NPC609763
0.5154	Remote Similarity	NPC470915
0.5143	Remote Similarity	NPC120840
0.5128	Remote Similarity	NPC473538
0.512	Remote Similarity	NPC164389
0.512	Remote Similarity	NPC488526
0.5118	Remote Similarity	NPC64715
0.5111	Remote Similarity	NPC189575
0.5111	Remote Similarity	NPC488560
0.5108	Remote Similarity	NPC135849
0.5106	Remote Similarity	NPC488309
0.5088	Remote Similarity	NPC57362
0.5083	Remote Similarity	NPC48499
0.5081	Remote Similarity	NPC192791
0.5079	Remote Similarity	NPC105800
0.5078	Remote Similarity	NPC114484
0.5077	Remote Similarity	NPC31838
0.5076	Remote Similarity	NPC60557
0.5076	Remote Similarity	NPC67857
0.5074	Remote Similarity	NPC85154
0.5074	Remote Similarity	NPC71391
0.5072	Remote Similarity	NPC271610
0.5072	Remote Similarity	NPC470876
0.5071	Remote Similarity	NPC476991
0.5069	Remote Similarity	NPC488210
0.5042	Remote Similarity	NPC90856
0.5041	Remote Similarity	NPC295371
0.504	Remote Similarity	NPC160415
0.504	Remote Similarity	NPC117714

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7066
0.1-0.2	2033
0.2-0.3	47
0.3-0.4	3
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