NPASS Compound

Natural Product: NPC39211

Natural Product ID	NPC39211
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chikusetsusaponin-Iva Butyl Ester
IUPAC Name	butyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylate
Synonyms	Calenduloside F 6'-O-N Butyl Ester; Chikusetsusaponin-IVa butyl ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502145
PubChem CID	44566502
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 134140 0 0 0 0 0 0 0 0999 V2000 12.7606 2.5366 -0.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6597 1.3177 0.5859 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0667 1.7334 1.9295 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6799 2.3206 1.6744 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9288 1.3097 1.0629 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6148 1.3998 0.6751 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0204 2.4870 0.8852 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8781 0.3006 0.0346 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5537 0.6687 -0.2027 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9649 -0.3637 -0.9814 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6345 -0.4530 -0.7649 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1193 -1.5777 -0.1928 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7520 -1.3052 1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3016 -1.1312 1.5229 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5123 -0.6584 0.3006 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6666 -1.7474 -0.7264 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0381 -2.3056 -0.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1158 -3.7625 -0.3458 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3371 -2.4941 -2.3630 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9253 -1.3482 -1.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5564 -1.4211 -1.6134 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9241 -0.6049 -0.4109 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0422 -0.7390 0.7253 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3004 0.0053 1.9413 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7171 0.4281 1.9331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6504 -0.0506 1.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2413 -1.1311 0.1570 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0058 -2.4413 0.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3054 -1.3621 -0.8449 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6211 -1.6297 -0.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9975 -0.7033 0.9362 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0298 0.4160 1.0937 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4811 1.4018 2.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0903 0.8636 3.3379 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2712 1.7571 3.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1355 0.9822 4.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5929 -0.5158 3.3047 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1023 -1.4320 2.2327 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3596 -0.2213 0.5567 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3283 -0.5347 1.2647 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5820 0.5663 -0.5631 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9191 0.9474 -0.8022 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2739 0.3416 -2.0373 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6672 0.2662 -1.9920 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1319 -0.5729 -3.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5269 -0.6916 -3.1561 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2982 1.6220 -2.0334 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6636 2.5947 -1.0692 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1384 2.4075 -0.9840 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7153 3.1845 0.0810 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9899 3.8959 -1.4069 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6485 1.4921 -1.7172 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0600 0.8091 -0.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9767 0.6912 -0.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3272 -0.0692 -2.3919 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7981 0.3379 -2.4543 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5166 -0.1856 -1.2570 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6989 -1.5506 -1.2359 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9350 1.7195 -2.5489 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0842 -1.1155 -3.2864 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3676 2.2418 -1.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7621 2.8024 -0.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2359 3.3320 0.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6198 0.8056 0.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9572 0.6177 0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6650 2.5212 2.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9132 0.8359 2.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7135 3.2148 1.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2704 2.6293 2.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8591 -0.5591 0.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4412 -1.3397 -0.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0018 -2.2781 -0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0860 -2.1499 1.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3676 -0.4332 1.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8088 -1.9792 2.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1993 -0.2753 2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0562 -2.6178 -0.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5665 -4.4443 -1.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1805 -4.0293 -0.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6412 -3.7371 0.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3444 -3.0035 -2.4922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6432 -3.3281 -2.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2689 -1.5948 -2.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0820 -2.0977 -2.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2057 -0.3734 -2.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0899 -1.0064 -2.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -2.4905 -1.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0155 -1.8484 1.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1772 -0.6607 2.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3687 0.8679 2.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9893 1.1867 2.6323 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3468 -3.1292 0.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7288 -2.3240 1.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9736 -3.0323 0.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4175 -0.5690 -1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0258 -2.2924 -1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7828 -2.6622 0.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3744 -1.5476 -1.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0852 0.9593 0.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2899 2.0322 1.6044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7285 2.1679 2.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5185 1.4594 4.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0839 1.7280 3.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8193 2.7912 3.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7399 0.8072 5.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4246 0.1406 4.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5941 1.9483 4.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3116 -1.0510 4.2842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7182 -0.5677 3.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 -2.2984 2.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1058 -1.7960 2.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6302 0.5631 -0.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9157 -0.3074 -1.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8166 -0.1636 -4.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7260 -1.6158 -3.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8285 -1.4624 -2.6100 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2406 1.9823 -3.0872 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0470 2.3307 -0.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7437 2.7543 -1.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9812 3.8129 -0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7417 3.8738 -2.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8744 0.6445 -1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 1.5772 -0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9824 0.9679 -1.4978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2352 0.9820 -1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2684 0.8913 -1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2158 1.4945 0.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8420 1.0336 0.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6951 0.7922 -2.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2364 -0.1476 -3.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5488 0.2717 -1.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4680 -1.7644 -0.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7145 1.9809 -3.4591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6863 -0.7497 -4.1326 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 2 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 17 19 1 0 16 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 2 0 26 27 1 0 27 28 1 1 27 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 34 36 1 0 34 37 1 0 37 38 1 0 31 39 1 6 39 40 2 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 22 53 1 6 15 54 1 6 10 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 57 8 1 0 17 12 1 0 27 22 1 0 38 31 1 0 49 42 1 0 23 15 1 0 32 26 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 0 2 65 1 0 3 66 1 0 3 67 1 0 4 68 1 0 4 69 1 0 8 70 1 1 10 71 1 1 12 72 1 1 13 73 1 0 13 74 1 0 14 75 1 0 14 76 1 0 16 77 1 1 18 78 1 0 18 79 1 0 18 80 1 0 19 81 1 0 19 82 1 0 19 83 1 0 20 84 1 0 20 85 1 0 21 86 1 0 21 87 1 0 23 88 1 1 24 89 1 0 24 90 1 0 25 91 1 0 28 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 32 99 1 6 33100 1 0 33101 1 0 35102 1 0 35103 1 0 35104 1 0 36105 1 0 36106 1 0 36107 1 0 37108 1 0 37109 1 0 38110 1 0 38111 1 0 42112 1 1 44113 1 1 45114 1 0 45115 1 0 46116 1 0 47117 1 6 48118 1 1 49119 1 6 50120 1 0 51121 1 0 52122 1 0 53123 1 0 53124 1 0 53125 1 0 54126 1 0 54127 1 0 54128 1 0 55129 1 6 56130 1 6 57131 1 6 58132 1 0 59133 1 0 60134 1 0 M END

Standard InCHIKey	UMELIPOCPCVHGJ-GUQBEPFPSA-N
Standard InCHI	InChI=1S/C46H74O14/c1-9-10-21-56-37(54)36-33(51)32(50)35(53)39(59-36)58-29-14-15-43(6)27(42(29,4)5)13-16-45(8)28(43)12-11-24-25-22-41(2,3)17-19-46(25,20-18-44(24,45)7)40(55)60-38-34(52)31(49)30(48)26(23-47)57-38/h11,25-36,38-39,47-53H,9-10,12-23H2,1-8H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34+,35+,36-,38-,39+,43-,44+,45+,46-/m0/s1
SMILES	CCCCOC(=O)[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	850.51	Volume:	859.43 ? Van der Waals volume.
Dense:	0.99	LogP:	3.226 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.45 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.842 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	40.0
TPSA:	221.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.076	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.87	Fsp³:	0.913
MCE-18:	150.182 ? 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:	0.982	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.218	Promiscuous compounds:	0.094

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.608	MDCK Permeability:	-5.096
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.994 ? 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):	0.088
20% Bioavailability (F20%):	0.691	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.282	MRP1:	0.024
Plasma Protein Binding (PPB):	78.016%	Volume Distribution (VD):	-0.244
Fu:	17.755% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.169

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.251 ? 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):

0.365

Half-life (T1/2):

3.357

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.189
Human Hepatotoxicity (H-HT):	0.438	Drug-induced Liver Injury (DILI):	0.906
AMES Toxicity:	0.408	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	0.998
Carcinogencity:	0.131	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.964
Hematotoxicity:	0.11	Drug-induced Nephrotoxicity:	0.957
Genotoxicity:	0.061	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.148	Hek293 Cytotoxicity:	0.391
BCF:	2.502 ? 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:	4.922 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.132 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.682 ? 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
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350149]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21417387]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[21417387]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28006911]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28005.2	Panax japonicus var. major (burk.) wu et feng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8750	Lychnis githago	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6196	Aralia armata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10972	Lysimachia patungensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3067	Frullania nisquallensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10373	Senna pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8494	Pteris longipes	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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
Activity	8
IC50	3
GI50	50
ID50	1

Activity Type	# Activity
Cell line	51
Organism	1
Others	7
Non-molecular	3

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17190444]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[17190444]
NPT116	Cell line	HL-60	Homo sapiens	GI50	=	1210.0	nM	PMID[17190444]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	=	23100.0	nM	PMID[17190444]
NPT111	Cell line	K562	Homo sapiens	GI50	=	1580.0	nM	PMID[17190444]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	=	1000.0	nM	PMID[17190444]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	=	780.0	nM	PMID[17190444]
NPT81	Cell line	A549	Homo sapiens	GI50	=	1830.0	nM	PMID[17190444]
NPT394	Cell line	EKVX	Homo sapiens	GI50	=	3390.0	nM	PMID[17190444]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	=	2220.0	nM	PMID[17190444]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	=	1040.0	nM	PMID[17190444]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	=	1490.0	nM	PMID[17190444]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	=	1480.0	nM	PMID[17190444]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	=	4080.0	nM	PMID[17190444]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	2510.0	nM	PMID[17190444]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	=	1360.0	nM	PMID[17190444]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	=	890.0	nM	PMID[17190444]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	2070.0	nM	PMID[17190444]
NPT386	Cell line	KM12	Homo sapiens	GI50	=	2080.0	nM	PMID[17190444]
NPT323	Cell line	SW-620	Homo sapiens	GI50	=	1930.0	nM	PMID[17190444]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	2170.0	nM	PMID[17190444]
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	2560.0	nM	PMID[17190444]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	=	1440.0	nM	PMID[17190444]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	1060.0	nM	PMID[17190444]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	=	810.0	nM	PMID[17190444]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	=	1470.0	nM	PMID[17190444]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	=	1850.0	nM	PMID[17190444]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	=	930.0	nM	PMID[17190444]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	=	4180.0	nM	PMID[17190444]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	890.0	nM	PMID[17190444]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	=	1700.0	nM	PMID[17190444]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	=	3270.0	nM	PMID[17190444]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	=	3070.0	nM	PMID[17190444]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	=	4280.0	nM	PMID[17190444]
NPT401	Cell line	786-0	Homo sapiens	GI50	=	1560.0	nM	PMID[17190444]
NPT369	Cell line	ACHN	Homo sapiens	GI50	=	6290.0	nM	PMID[17190444]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	=	17200.0	nM	PMID[17190444]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	=	1650.0	nM	PMID[17190444]
NPT368	Cell line	SN12C	Homo sapiens	GI50	=	1390.0	nM	PMID[17190444]
NPT384	Cell line	TK-10	Homo sapiens	GI50	=	1850.0	nM	PMID[17190444]
NPT371	Cell line	UO-31	Homo sapiens	GI50	=	12700.0	nM	PMID[17190444]
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	1260.0	nM	PMID[17190444]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	1600.0	nM	PMID[17190444]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	>	50000.0	nM	PMID[17190444]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	1150.0	nM	PMID[17190444]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	=	2520.0	nM	PMID[17190444]
NPT457	Cell line	BT-549	Homo sapiens	GI50	=	1700.0	nM	PMID[17190444]
NPT396	Cell line	T47D	Homo sapiens	GI50	=	1750.0	nM	PMID[17190444]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	6730.0	nM	PMID[17190444]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	1120.0	nM	PMID[17190444]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	2600.0	nM	PMID[17190444]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	1620.0	nM	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Activity	=	10.1	%	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Activity	=	48.1	%	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Activity	=	70.0	%	PMID[17190444]
NPT2	Others	Unspecified	n.a.	IC50	=	479.0	molar ratio	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[17190444]
NPT2	Others	Unspecified	n.a.	IC50	=	3730.0	nM	PMID[21417387]
NPT2	Others	Unspecified	n.a.	IC50	=	7280.0	nM	PMID[21417387]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.07	mg	PMID[17190444]

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 NPC39211 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	19903
0.1-0.2	24956
0.2-0.3	3650
0.3-0.4	824
0.4-0.5	320
0.5-0.6	130
0.6-0.7	43
0.7-0.8	0
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8925	High Similarity	NPC104372
0.871	High Similarity	NPC222580
0.8621	High Similarity	NPC214484
0.8602	High Similarity	NPC235438
0.8351	Intermediate Similarity	NPC80986
0.8081	Intermediate Similarity	NPC31838
0.8022	Intermediate Similarity	NPC48499
0.7708	Intermediate Similarity	NPC223301
0.7708	Intermediate Similarity	NPC171544
0.766	Intermediate Similarity	NPC235405
0.766	Intermediate Similarity	NPC475516
0.7579	Intermediate Similarity	NPC249848
0.7579	Intermediate Similarity	NPC107966
0.7273	Intermediate Similarity	NPC30735
0.72	Intermediate Similarity	NPC10607
0.7172	Intermediate Similarity	NPC112352
0.7143	Intermediate Similarity	NPC157868
0.7129	Intermediate Similarity	NPC63159
0.7071	Intermediate Similarity	NPC469946
0.7059	Intermediate Similarity	NPC297263
0.7053	Intermediate Similarity	NPC90856
0.703	Intermediate Similarity	NPC40775
0.703	Intermediate Similarity	NPC159309
0.703	Intermediate Similarity	NPC46665
0.703	Intermediate Similarity	NPC86222
0.7	Intermediate Similarity	NPC192791
0.6889	Remote Similarity	NPC167383
0.6863	Remote Similarity	NPC251768
0.6804	Remote Similarity	NPC1046
0.68	Remote Similarity	NPC295371
0.6796	Remote Similarity	NPC475591
0.6796	Remote Similarity	NPC236870
0.6762	Remote Similarity	NPC281148
0.6762	Remote Similarity	NPC114484
0.6739	Remote Similarity	NPC237503
0.6698	Remote Similarity	NPC481079
0.6574	Remote Similarity	NPC187290
0.6542	Remote Similarity	NPC301449
0.6542	Remote Similarity	NPC601290
0.6535	Remote Similarity	NPC473373
0.6495	Remote Similarity	NPC209894
0.6486	Remote Similarity	NPC79643
0.6481	Remote Similarity	NPC295823
0.6481	Remote Similarity	NPC174720
0.6481	Remote Similarity	NPC475467
0.6471	Remote Similarity	NPC473884
0.6465	Remote Similarity	NPC78046
0.6465	Remote Similarity	NPC29069
0.646	Remote Similarity	NPC475160
0.646	Remote Similarity	NPC473714
0.6422	Remote Similarity	NPC481078
0.6392	Remote Similarity	NPC128925
0.6381	Remote Similarity	NPC480475
0.6372	Remote Similarity	NPC135904
0.6364	Remote Similarity	NPC204458
0.6348	Remote Similarity	NPC481080
0.6346	Remote Similarity	NPC242840
0.6316	Remote Similarity	NPC470218
0.6293	Remote Similarity	NPC476068
0.6228	Remote Similarity	NPC123199
0.6214	Remote Similarity	NPC58448
0.6214	Remote Similarity	NPC150400
0.6106	Remote Similarity	NPC60557
0.6106	Remote Similarity	NPC67857
0.6075	Remote Similarity	NPC164389
0.605	Remote Similarity	NPC41061
0.605	Remote Similarity	NPC227551
0.605	Remote Similarity	NPC258617
0.6	Remote Similarity	NPC43550
0.5983	Remote Similarity	NPC488560
0.5981	Remote Similarity	NPC309714
0.5979	Remote Similarity	NPC306746
0.5979	Remote Similarity	NPC199457
0.595	Remote Similarity	NPC305981
0.595	Remote Similarity	NPC481081
0.5943	Remote Similarity	NPC473343
0.5943	Remote Similarity	NPC76497
0.5929	Remote Similarity	NPC62725
0.5926	Remote Similarity	NPC473459
0.5918	Remote Similarity	NPC68419
0.5909	Remote Similarity	NPC64715
0.5902	Remote Similarity	NPC261506
0.5902	Remote Similarity	NPC4328
0.5893	Remote Similarity	NPC480473
0.5893	Remote Similarity	NPC241909
0.5893	Remote Similarity	NPC480474
0.5888	Remote Similarity	NPC75417
0.5872	Remote Similarity	NPC148417
0.5833	Remote Similarity	NPC160415
0.5826	Remote Similarity	NPC475287
0.581	Remote Similarity	NPC139894
0.5794	Remote Similarity	NPC263756
0.5794	Remote Similarity	NPC161674
0.5794	Remote Similarity	NPC213674
0.5789	Remote Similarity	NPC11242
0.5784	Remote Similarity	NPC480951
0.5776	Remote Similarity	NPC192600
0.5763	Remote Similarity	NPC100639
0.576	Remote Similarity	NPC250247
0.5758	Remote Similarity	NPC604133
0.5755	Remote Similarity	NPC173583
0.575	Remote Similarity	NPC57484
0.5743	Remote Similarity	NPC256798
0.5728	Remote Similarity	NPC189884
0.5728	Remote Similarity	NPC269095
0.5728	Remote Similarity	NPC138334
0.5727	Remote Similarity	NPC68175
0.5702	Remote Similarity	NPC104137
0.5702	Remote Similarity	NPC26626
0.5688	Remote Similarity	NPC104071
0.5676	Remote Similarity	NPC475504
0.5636	Remote Similarity	NPC102439
0.5636	Remote Similarity	NPC11551
0.5636	Remote Similarity	NPC2370
0.5631	Remote Similarity	NPC47063
0.5614	Remote Similarity	NPC481030
0.5565	Remote Similarity	NPC236638
0.5565	Remote Similarity	NPC294453
0.5556	Remote Similarity	NPC76972
0.5556	Remote Similarity	NPC469782
0.5556	Remote Similarity	NPC204414
0.5545	Remote Similarity	NPC109588
0.5536	Remote Similarity	NPC31193
0.5536	Remote Similarity	NPC609763
0.5528	Remote Similarity	NPC475514
0.55	Remote Similarity	NPC283417
0.55	Remote Similarity	NPC200049
0.55	Remote Similarity	NPC606107
0.5492	Remote Similarity	NPC21691
0.5484	Remote Similarity	NPC65105
0.5476	Remote Similarity	NPC70809
0.5472	Remote Similarity	NPC475208
0.5464	Remote Similarity	NPC191763
0.5462	Remote Similarity	NPC481031
0.5455	Remote Similarity	NPC46388
0.5446	Remote Similarity	NPC137917
0.5429	Remote Similarity	NPC473481
0.5417	Remote Similarity	NPC155410
0.5413	Remote Similarity	NPC470512
0.541	Remote Similarity	NPC4749
0.5405	Remote Similarity	NPC117714
0.5405	Remote Similarity	NPC30289
0.5397	Remote Similarity	NPC298034
0.5397	Remote Similarity	NPC71065
0.5392	Remote Similarity	NPC31839
0.5378	Remote Similarity	NPC123522
0.5372	Remote Similarity	NPC471550
0.536	Remote Similarity	NPC293330
0.5357	Remote Similarity	NPC180550
0.5357	Remote Similarity	NPC35405
0.5347	Remote Similarity	NPC37739
0.5345	Remote Similarity	NPC96641
0.5345	Remote Similarity	NPC163183
0.534	Remote Similarity	NPC220984
0.5333	Remote Similarity	NPC162107
0.5333	Remote Similarity	NPC46912
0.5333	Remote Similarity	NPC161434
0.53	Remote Similarity	NPC605954
0.5294	Remote Similarity	NPC310014
0.5294	Remote Similarity	NPC269315
0.5285	Remote Similarity	NPC85154
0.5248	Remote Similarity	NPC116794
0.5243	Remote Similarity	NPC271138
0.5243	Remote Similarity	NPC110139
0.5243	Remote Similarity	NPC108709
0.5229	Remote Similarity	NPC108748
0.5225	Remote Similarity	NPC475171
0.5221	Remote Similarity	NPC44716
0.5221	Remote Similarity	NPC488526
0.5221	Remote Similarity	NPC173859
0.5221	Remote Similarity	NPC305267
0.5221	Remote Similarity	NPC148603
0.5217	Remote Similarity	NPC471435
0.5217	Remote Similarity	NPC471434
0.5207	Remote Similarity	NPC475899
0.5207	Remote Similarity	NPC165204
0.52	Remote Similarity	NPC286457
0.5194	Remote Similarity	NPC220160
0.5175	Remote Similarity	NPC470515
0.5169	Remote Similarity	NPC36831
0.5167	Remote Similarity	NPC268184
0.5161	Remote Similarity	NPC301639
0.5161	Remote Similarity	NPC478065
0.5156	Remote Similarity	NPC302543
0.5146	Remote Similarity	NPC7870
0.5146	Remote Similarity	NPC75747
0.514	Remote Similarity	NPC238935
0.513	Remote Similarity	NPC470513
0.5126	Remote Similarity	NPC75287
0.5122	Remote Similarity	NPC191827
0.5109	Remote Similarity	NPC191965
0.51	Remote Similarity	NPC473844
0.5096	Remote Similarity	NPC102914
0.5089	Remote Similarity	NPC471547
0.5078	Remote Similarity	NPC202828
0.5078	Remote Similarity	NPC119592
0.5077	Remote Similarity	NPC224381
0.5046	Remote Similarity	NPC179434
0.5045	Remote Similarity	NPC480420

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7121
0.1-0.2	1961
0.2-0.3	61
0.3-0.4	7
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