NPASS Compound

Natural Product: NPC204392

Natural Product ID	NPC204392
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-[(O-Alpha-L-Rhamnopyranosyl-(1->2)-O-[O-Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl)Oxy]Lup-20(29)-En-28-Oic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500097
PubChem CID	11672401
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 139146 0 0 0 0 0 0 0 0999 V2000 6.8968 2.3646 -4.0827 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5160 1.3687 -3.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6119 0.0527 -4.1586 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1202 1.5647 -2.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5673 1.0861 -2.2674 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7313 -0.0347 -1.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6833 0.3272 -0.2373 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2420 -0.8246 0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9743 -0.5365 1.3273 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8709 0.0086 0.4638 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4386 -0.9846 -0.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4318 1.1971 -0.2999 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4022 1.9807 -1.0354 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2400 2.3021 -0.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6941 0.9884 0.3702 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2651 1.0211 0.8181 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9530 2.0910 1.7947 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4203 1.2911 -0.4291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7180 0.0830 -0.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2322 -0.5540 0.0511 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4893 -0.7117 1.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2399 -0.0259 2.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4477 -2.2149 1.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9325 -0.3804 1.2405 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7288 -0.7385 2.4342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2165 -0.8030 2.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6869 0.4098 1.3377 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1514 1.3931 2.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4433 0.1140 0.1291 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5121 -0.6193 -0.3845 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5529 -0.8592 0.6919 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2061 0.4619 1.0148 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9028 0.9147 -0.2765 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7432 1.1564 -1.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 0.0036 -1.4894 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5852 2.0717 0.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9191 1.9522 -0.2927 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8431 2.1285 0.8823 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1788 1.4972 0.4665 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6398 2.2698 -0.7459 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5716 2.4700 -1.7687 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0604 3.5718 -2.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2936 3.1598 -3.2117 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3550 2.8667 -1.2720 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6653 1.5104 -1.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1087 1.5898 1.4725 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3785 1.6003 2.0603 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2447 1.4352 1.2684 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5758 -1.6808 0.1925 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7877 -2.7889 0.9832 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1691 -2.8886 1.5511 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5800 -4.3358 1.7940 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4083 -5.1856 0.5564 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6201 -4.3516 -0.4505 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2920 -5.1907 -1.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4835 -3.9143 0.1908 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5977 -5.6479 0.0383 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7796 -4.8466 2.8177 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2721 -2.2446 2.7951 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5113 0.6402 -1.1824 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0889 1.4839 0.5645 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2151 1.3519 1.8108 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3503 2.7355 0.0551 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4606 2.1932 -5.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8245 3.3334 -3.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2689 0.0857 -5.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0319 -0.7308 -3.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6166 -0.2913 -4.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0702 2.6326 -1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2148 1.9455 -1.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8122 0.6919 -3.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7476 0.0639 -0.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5298 -1.0286 -1.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2166 -1.7712 0.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0367 -0.9883 1.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1992 0.2353 2.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6399 -1.4340 1.8958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2386 -1.7733 -0.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2514 -0.4745 -1.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5265 -1.5336 -0.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9704 1.9202 0.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8590 2.9670 -1.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0170 1.5278 -1.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5927 2.9495 0.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5437 2.9187 -0.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6922 0.3165 -0.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9368 2.5351 1.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9396 1.8170 2.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 2.9610 1.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6446 2.0700 -0.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0338 1.6884 -1.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0763 0.4312 -1.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3787 -0.6908 -1.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4758 -1.5578 -0.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3607 0.0938 3.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1006 -0.6864 2.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7170 0.9220 2.1339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3999 -2.3549 2.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2789 -2.7160 1.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5005 -2.6314 1.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3214 -1.0325 0.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4443 -1.7585 2.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6096 -0.0752 3.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4330 -1.7642 1.6280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7152 -0.8560 3.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8912 2.1162 2.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3307 1.9363 2.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 0.7977 3.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0913 -1.6040 -0.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1192 -1.2535 1.6145 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9317 0.3733 1.8536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5481 0.1292 -0.6776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1039 1.6308 -2.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0611 1.8728 -0.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1091 0.9215 -0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0901 3.2165 1.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9360 0.4620 0.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0572 3.2468 -0.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4252 1.5289 -2.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2067 4.5009 -2.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3159 3.7572 -3.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2863 3.3387 -4.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2066 0.7867 -1.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8521 0.9709 1.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1523 1.2405 2.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1669 1.6233 2.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0769 -2.7465 1.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9334 -2.4350 0.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6561 -4.3119 2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7637 -6.0738 0.7795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2226 -3.4990 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5369 -5.9697 -1.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2471 -5.6829 -1.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0044 -4.4968 -2.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3349 -5.6686 0.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1991 -5.5665 2.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6882 -2.7251 3.4503 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2736 -0.3058 -1.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1184 3.5857 0.5262 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 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 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 20 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 0 33 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 32 48 1 0 31 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 54 56 1 0 53 57 1 0 52 58 1 0 51 59 1 0 12 60 1 0 7 61 1 1 61 62 2 0 61 63 1 0 60 4 1 0 60 7 1 0 27 10 1 0 35 30 1 0 44 37 1 0 56 50 1 0 27 15 1 0 24 16 1 0 1 64 1 0 1 65 1 0 3 66 1 0 3 67 1 0 3 68 1 0 4 69 1 1 5 70 1 0 5 71 1 0 6 72 1 0 6 73 1 0 8 74 1 0 8 75 1 0 9 76 1 0 9 77 1 0 11 78 1 0 11 79 1 0 11 80 1 0 12 81 1 1 13 82 1 0 13 83 1 0 14 84 1 0 14 85 1 0 15 86 1 6 17 87 1 0 17 88 1 0 17 89 1 0 18 90 1 0 18 91 1 0 19 92 1 0 19 93 1 0 20 94 1 6 22 95 1 0 22 96 1 0 22 97 1 0 23 98 1 0 23 99 1 0 23100 1 0 24101 1 6 25102 1 0 25103 1 0 26104 1 0 26105 1 0 28106 1 0 28107 1 0 28108 1 0 30109 1 6 31110 1 1 32111 1 1 33112 1 6 34113 1 0 34114 1 0 37115 1 6 38116 1 1 39117 1 6 40118 1 1 41119 1 6 42120 1 0 42121 1 0 43122 1 0 45123 1 0 46124 1 0 47125 1 0 48126 1 0 50127 1 1 51128 1 6 52129 1 1 53130 1 1 54131 1 6 55132 1 0 55133 1 0 55134 1 0 57135 1 0 58136 1 0 59137 1 0 60138 1 6 63139 1 0 M END

Standard InCHIKey	WOOPUJXMROOOPP-KSYIBZFCSA-N
Standard InCHI	InChI=1S/C47H76O16/c1-21(2)23-11-16-47(42(56)57)18-17-45(7)24(30(23)47)9-10-28-44(6)14-13-29(43(4,5)27(44)12-15-46(28,45)8)62-41-38(63-39-36(54)34(52)31(49)22(3)59-39)33(51)26(20-58-41)61-40-37(55)35(53)32(50)25(19-48)60-40/h22-41,48-55H,1,9-20H2,2-8H3,(H,56,57)/t22-,23-,24+,25+,26-,27-,28+,29-,30+,31-,32+,33-,34+,35-,36+,37+,38+,39-,40-,41-,44-,45+,46+,47-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	896.51	Volume:	888.387 ? Van der Waals volume.
Dense:	1.009	LogP:	1.767 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.431 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.95 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	45.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.219	Fsp³:	0.936
MCE-18:	170.264 ? 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:	0.951	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.211	Promiscuous compounds:	0.181

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.048	MDCK Permeability:	-5.134
Pgp-inhibitor:	0.0	Pgp-substrate:	0.101
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):	0.002
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.765
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.776
Plasma Protein Binding (PPB):	80.923%	Volume Distribution (VD):	-0.493
Fu:	13.557% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.057	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.019	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
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):

0.155

Half-life (T1/2):

2.722

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.736	Drug-induced Liver Injury (DILI):	0.958
AMES Toxicity:	0.878	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.191	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.571	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.139	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.287	Hek293 Cytotoxicity:	0.158
BCF:	0.996 ? 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:	3.442 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.864 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.145 ? 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
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[15473660]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730260]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24360605]
NPO31082	Pulsatilla koreana	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
ED50	1
IC50	4

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[20056545]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[20022253]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	50000.0	nM	PMID[22779787]
NPT81	Cell line	A549	Homo sapiens	IC50	>	200000.0	nM	PMID[12161151]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	200000.0	nM	PubChem BioAssay data set

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 NPC204392 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	22604
0.1-0.2	22520
0.2-0.3	3386
0.3-0.4	964
0.4-0.5	329
0.5-0.6	43
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC240734
0.7879	Intermediate Similarity	NPC275668
0.7255	Intermediate Similarity	NPC91838
0.7188	Intermediate Similarity	NPC51947
0.6698	Remote Similarity	NPC257468
0.6481	Remote Similarity	NPC488206
0.6458	Remote Similarity	NPC88744
0.625	Remote Similarity	NPC488205
0.6147	Remote Similarity	NPC139044
0.6117	Remote Similarity	NPC488208
0.5929	Remote Similarity	NPC323359
0.5897	Remote Similarity	NPC151543
0.5877	Remote Similarity	NPC488564
0.5847	Remote Similarity	NPC471384
0.5798	Remote Similarity	NPC166422
0.5798	Remote Similarity	NPC470622
0.5763	Remote Similarity	NPC126753
0.5702	Remote Similarity	NPC54636
0.5688	Remote Similarity	NPC488207
0.5631	Remote Similarity	NPC224414
0.5575	Remote Similarity	NPC471383
0.5526	Remote Similarity	NPC470478
0.5435	Remote Similarity	NPC4309
0.5421	Remote Similarity	NPC236753
0.5391	Remote Similarity	NPC123796
0.5364	Remote Similarity	NPC25605
0.5339	Remote Similarity	NPC184805
0.5328	Remote Similarity	NPC323341
0.5319	Remote Similarity	NPC160506
0.5315	Remote Similarity	NPC127056
0.5299	Remote Similarity	NPC267238
0.5299	Remote Similarity	NPC207693
0.5299	Remote Similarity	NPC78034
0.5285	Remote Similarity	NPC219180
0.5268	Remote Similarity	NPC224003
0.5254	Remote Similarity	NPC157571
0.5254	Remote Similarity	NPC324875
0.5254	Remote Similarity	NPC292677
0.5242	Remote Similarity	NPC475140
0.5225	Remote Similarity	NPC475296
0.5225	Remote Similarity	NPC56713
0.5214	Remote Similarity	NPC253611
0.5214	Remote Similarity	NPC488782
0.5179	Remote Similarity	NPC18724
0.5161	Remote Similarity	NPC271974
0.5161	Remote Similarity	NPC247312
0.513	Remote Similarity	NPC114304
0.5126	Remote Similarity	NPC40716
0.5098	Remote Similarity	NPC473844
0.5091	Remote Similarity	NPC164194
0.5089	Remote Similarity	NPC108748
0.5089	Remote Similarity	NPC474589
0.5088	Remote Similarity	NPC158051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6299
0.1-0.2	2766
0.2-0.3	74
0.3-0.4	8
0.4-0.5	1
0.5-0.6	2
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
0.5319	Remote Similarity	NPD8035	Phase 2
0.5234	Remote Similarity	NPD8034	Phase 2

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