NPASS Compound

Natural Product: NPC218954

Natural Product ID	NPC218954
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IBZLICPLPYSFNZ-JCGKQQEISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21634074
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 140147 0 0 0 0 0 0 0 0999 V2000 -7.9303 1.9419 -3.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5943 2.8442 -2.8385 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.0594 2.4735 -2.7976 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5960 2.8491 -1.4176 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8968 1.9513 -0.4331 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4651 1.7024 -0.8425 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9818 2.7326 -1.6176 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7209 1.5164 0.3226 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1719 0.2549 0.4449 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7684 -0.3303 1.7329 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3801 0.5670 2.8625 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9477 1.0355 2.8228 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5661 1.5093 1.5693 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6861 0.4024 0.6906 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1646 -0.6728 1.3757 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0480 -1.2449 0.7321 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3580 -2.6605 0.3119 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4103 -3.6531 0.9366 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3079 -3.3780 2.4091 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2562 -4.2260 3.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3227 -3.7960 3.7264 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2680 -5.6229 2.8216 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0837 -2.0679 2.7146 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8455 -1.2282 1.6184 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7511 -1.7030 0.9575 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6321 -0.8819 1.0469 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3565 -1.6604 1.8654 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 -1.3318 1.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2130 -1.2297 0.2390 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2002 -2.5730 -0.3499 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2981 -0.2022 -0.3726 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7841 0.4893 -1.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1779 0.2174 -2.0248 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1671 -0.2501 -1.0176 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8344 -1.5160 -1.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5813 -0.5664 0.3146 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4846 -1.2542 1.2715 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8568 -0.6980 1.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2222 0.1755 0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6356 0.6224 0.2455 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8032 2.0952 0.5439 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2833 2.3090 0.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5739 2.3614 2.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7585 3.6272 0.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1265 1.2156 0.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6606 0.7881 -1.1659 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2188 0.2602 -1.0931 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3470 -1.2636 -1.1007 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4342 0.6995 -2.2701 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0144 1.0504 -2.1012 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3372 0.7323 -0.8269 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7424 2.0083 -0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5349 -0.1526 -1.6439 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1603 -0.5693 -0.3497 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8885 0.7352 -0.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6258 -1.5980 -1.3118 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2523 -1.4347 -2.6341 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0748 -4.9071 0.8320 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2097 -2.7465 -1.0719 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1894 1.7227 2.7712 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4335 -1.6514 1.9127 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5337 0.6940 -0.3801 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9628 2.5732 -1.3184 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7284 3.2674 -3.7231 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3553 2.1389 -4.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1596 0.8996 -3.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8411 2.1264 -3.8201 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5360 3.9220 -3.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2450 1.3926 -2.9401 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3761 3.9072 -1.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8666 2.4150 0.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4106 0.7384 -1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4119 -0.3987 -0.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8759 -0.2308 1.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5281 0.0906 3.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2969 0.2078 3.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8506 1.8879 3.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1252 0.5871 -0.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8779 -0.6338 -0.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4234 -2.9211 0.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4700 -3.7982 0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2741 -3.7625 2.8587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4812 -6.2030 3.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6581 -0.2133 2.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9285 0.0032 1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1062 -1.5016 2.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2249 -2.7619 1.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0482 -0.3364 2.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3837 -2.0865 2.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4882 -3.2215 0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9327 -2.6635 -1.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1958 -3.0637 -0.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 0.6182 0.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6308 1.6189 -1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1141 0.2822 -2.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1594 -0.4663 -2.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5788 1.1774 -2.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -2.1486 -2.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6811 -1.3021 -2.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2832 -2.1373 -0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3548 0.4409 0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4677 -2.3548 1.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1653 -0.9930 2.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5800 -1.0658 1.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2452 0.0856 1.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2744 2.3019 1.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5342 2.7448 -0.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2427 3.3245 2.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1497 1.4793 2.8098 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6836 2.2985 2.4065 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9530 3.5727 -0.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9371 4.3610 0.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6682 3.9949 0.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1528 1.6574 0.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2604 0.3410 0.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6621 1.6529 -1.8694 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3877 -1.6032 -0.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6290 -1.7423 -0.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0746 -1.6104 -2.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0085 1.5624 -2.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5786 -0.0966 -3.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4406 0.5729 -2.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8889 2.1547 -2.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1865 2.8908 -0.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6674 2.0961 -0.3512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9502 2.1026 0.8595 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1563 -0.5137 -0.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6641 1.0316 -1.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9434 0.7227 -0.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4124 1.5120 -0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4132 -2.6525 -1.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7703 -1.6022 -1.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8938 -1.8046 -3.2705 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0241 -5.2379 -0.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7039 -3.5344 -1.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0276 1.6062 3.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9819 -2.1821 1.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0655 0.6033 0.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1579 2.2235 -0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7118 3.1419 -3.7001 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 0 20 21 2 0 20 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 6 34 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 42 45 1 0 45 46 1 0 46 47 1 0 47 48 1 1 47 49 1 0 49 50 1 0 50 51 1 0 51 52 1 1 46 53 1 0 31 54 1 0 54 55 1 6 54 56 1 0 56 57 1 0 18 58 1 0 17 59 1 0 11 60 1 0 10 61 1 0 5 62 1 0 4 63 1 0 3 64 1 0 7 2 1 0 14 9 1 0 24 16 1 0 54 26 1 0 36 29 1 0 51 39 1 0 51 34 1 0 47 40 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 6 3 69 1 6 4 70 1 1 5 71 1 1 6 72 1 6 9 73 1 6 10 74 1 6 11 75 1 1 12 76 1 0 12 77 1 0 14 78 1 6 16 79 1 6 17 80 1 6 18 81 1 6 19 82 1 1 22 83 1 0 24 84 1 1 26 85 1 1 27 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 30 90 1 0 30 91 1 0 30 92 1 0 31 93 1 1 32 94 1 0 32 95 1 0 33 96 1 0 33 97 1 0 35 98 1 0 35 99 1 0 35100 1 0 36101 1 1 37102 1 0 37103 1 0 38104 1 0 40105 1 1 41106 1 0 41107 1 0 43108 1 0 43109 1 0 43110 1 0 44111 1 0 44112 1 0 44113 1 0 45114 1 0 45115 1 0 46116 1 6 48117 1 0 48118 1 0 48119 1 0 49120 1 0 49121 1 0 50122 1 0 50123 1 0 52124 1 0 52125 1 0 52126 1 0 53127 1 0 55128 1 0 55129 1 0 55130 1 0 56131 1 0 56132 1 0 57133 1 0 58134 1 0 59135 1 0 60136 1 0 61137 1 0 62138 1 0 63139 1 0 64140 1 0 M END

Standard InCHIKey	IBZLICPLPYSFNZ-JCGKQQEISA-N
Standard InCHI	InChI=1S/C47H76O17/c1-21-29(51)31(53)34(56)39(60-21)63-36-30(52)24(49)19-59-40(36)64-37-33(55)32(54)35(38(57)58)62-41(37)61-28-12-13-44(5)25(45(28,6)20-48)11-14-47(8)26(44)10-9-22-23-17-42(2,3)18-27(50)43(23,4)15-16-46(22,47)7/h9,21,23-37,39-41,48-56H,10-20H2,1-8H3,(H,57,58)/t21-,23-,24+,25+,26+,27+,28-,29-,30-,31+,32-,33-,34+,35-,36+,37+,39-,40-,41+,43+,44-,45+,46+,47+/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]1[C@H]([C@@H]([C@@H](C(=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[C@H]([C@]4(C)CC[C@@]32C)O)[C@@]1(C)CO)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	912.51	Volume:	897.177 ? Van der Waals volume.
Dense:	1.017	LogP:	1.234 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.861 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.682 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	45.0
TPSA:	274.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.122	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.367	Fsp³:	0.936
MCE-18:	174.462 ? 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:	0.737	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.225	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.056	MDCK Permeability:	-5.152
Pgp-inhibitor:	0.0	Pgp-substrate:	0.722
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):	0.17
20% Bioavailability (F20%):	0.51	30% Bioavailability (F30%):	0.788
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.734
Plasma Protein Binding (PPB):	71.333%	Volume Distribution (VD):	-0.475
Fu:	17.609% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
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):

0.096

Half-life (T1/2):

3.67

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.4	Drug-induced Liver Injury (DILI):	0.845
AMES Toxicity:	0.251	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	0.997
Carcinogencity:	0.053	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.207	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.548	RPMI-8226 Immunitoxicity:	0.168
A549 Cytotoxicity:	0.132	Hek293 Cytotoxicity:	0.217
BCF:	0.778 ? 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:	3.344 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.848 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.87 ? 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
NPO19849	Melilotus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19849	Melilotus officinalis	Species	Fabaceae	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	1

Activity Type	# Activity
Cell line	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
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	0.0	%	PMID[29353722]

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 NPC218954 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	22347
0.1-0.2	23577
0.2-0.3	2704
0.3-0.4	719
0.4-0.5	350
0.5-0.6	128
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC236657
0.802	Intermediate Similarity	NPC118440
0.7981	Intermediate Similarity	NPC187618
0.785	Intermediate Similarity	NPC313110
0.7196	Intermediate Similarity	NPC95437
0.713	Intermediate Similarity	NPC114692
0.7113	Intermediate Similarity	NPC224121
0.7103	Intermediate Similarity	NPC131469
0.6847	Remote Similarity	NPC120116
0.6667	Remote Similarity	NPC174679
0.6667	Remote Similarity	NPC279554
0.6283	Remote Similarity	NPC486563
0.6147	Remote Similarity	NPC482748
0.6055	Remote Similarity	NPC56713
0.6055	Remote Similarity	NPC59804
0.6034	Remote Similarity	NPC301449
0.6034	Remote Similarity	NPC601290
0.6018	Remote Similarity	NPC251768
0.5968	Remote Similarity	NPC21691
0.5917	Remote Similarity	NPC76972
0.5917	Remote Similarity	NPC469782
0.5917	Remote Similarity	NPC204414
0.5913	Remote Similarity	NPC475504
0.5897	Remote Similarity	NPC486564
0.5862	Remote Similarity	NPC64715
0.5841	Remote Similarity	NPC112352
0.5812	Remote Similarity	NPC276093
0.5794	Remote Similarity	NPC476774
0.5794	Remote Similarity	NPC476780
0.5763	Remote Similarity	NPC477075
0.5748	Remote Similarity	NPC258617
0.5726	Remote Similarity	NPC283417
0.5726	Remote Similarity	NPC200049
0.5691	Remote Similarity	NPC284449
0.5669	Remote Similarity	NPC265841
0.5664	Remote Similarity	NPC473884
0.5664	Remote Similarity	NPC472949
0.5635	Remote Similarity	NPC4749
0.5603	Remote Similarity	NPC164389
0.5581	Remote Similarity	NPC476779
0.5575	Remote Similarity	NPC127056
0.5573	Remote Similarity	NPC476775
0.5565	Remote Similarity	NPC482739
0.5556	Remote Similarity	NPC139044
0.5556	Remote Similarity	NPC471383
0.5547	Remote Similarity	NPC473452
0.5536	Remote Similarity	NPC12288
0.5512	Remote Similarity	NPC82380
0.5512	Remote Similarity	NPC244296
0.55	Remote Similarity	NPC477076
0.55	Remote Similarity	NPC477079
0.5487	Remote Similarity	NPC309780
0.5478	Remote Similarity	NPC482717
0.5476	Remote Similarity	NPC471550
0.5462	Remote Similarity	NPC484059
0.5462	Remote Similarity	NPC484060
0.5462	Remote Similarity	NPC302887
0.5455	Remote Similarity	NPC477077
0.5455	Remote Similarity	NPC477078
0.544	Remote Similarity	NPC133818
0.5426	Remote Similarity	NPC488308
0.5424	Remote Similarity	NPC162574
0.542	Remote Similarity	NPC202828
0.542	Remote Similarity	NPC119592
0.5403	Remote Similarity	NPC60557
0.5403	Remote Similarity	NPC67857
0.5385	Remote Similarity	NPC271610
0.5385	Remote Similarity	NPC312650
0.5385	Remote Similarity	NPC117714
0.5379	Remote Similarity	NPC298034
0.5379	Remote Similarity	NPC71065
0.5379	Remote Similarity	NPC11577
0.5379	Remote Similarity	NPC141600
0.5372	Remote Similarity	NPC324875
0.5372	Remote Similarity	NPC292677
0.5349	Remote Similarity	NPC484061
0.5349	Remote Similarity	NPC484062
0.5345	Remote Similarity	NPC80843
0.5344	Remote Similarity	NPC293330
0.5303	Remote Similarity	NPC110700
0.5303	Remote Similarity	NPC476777
0.5299	Remote Similarity	NPC192791
0.5299	Remote Similarity	NPC484063
0.5299	Remote Similarity	NPC484064
0.5294	Remote Similarity	NPC482722
0.5294	Remote Similarity	NPC63159
0.5294	Remote Similarity	NPC471963
0.5289	Remote Similarity	NPC482740
0.5285	Remote Similarity	NPC187290
0.5276	Remote Similarity	NPC135904
0.5263	Remote Similarity	NPC302543
0.5254	Remote Similarity	NPC160415
0.5254	Remote Similarity	NPC30289
0.525	Remote Similarity	NPC481082
0.525	Remote Similarity	NPC164419
0.5214	Remote Similarity	NPC475171
0.521	Remote Similarity	NPC104400
0.521	Remote Similarity	NPC10320
0.521	Remote Similarity	NPC11551
0.5203	Remote Similarity	NPC160452
0.5203	Remote Similarity	NPC241909
0.5203	Remote Similarity	NPC480474
0.5197	Remote Similarity	NPC323341
0.5194	Remote Similarity	NPC47995
0.5185	Remote Similarity	NPC28198
0.5185	Remote Similarity	NPC476123
0.5185	Remote Similarity	NPC488309
0.5167	Remote Similarity	NPC475591
0.5167	Remote Similarity	NPC236870
0.5164	Remote Similarity	NPC114484
0.5161	Remote Similarity	NPC475486
0.5161	Remote Similarity	NPC481078
0.5159	Remote Similarity	NPC252657
0.5159	Remote Similarity	NPC88311
0.5156	Remote Similarity	NPC219180
0.5154	Remote Similarity	NPC71391
0.5128	Remote Similarity	NPC157868
0.5124	Remote Similarity	NPC257468
0.5122	Remote Similarity	NPC481079
0.5118	Remote Similarity	NPC79643
0.5116	Remote Similarity	NPC269484
0.5116	Remote Similarity	NPC97918
0.5115	Remote Similarity	NPC470518
0.5113	Remote Similarity	NPC161717
0.5101	Remote Similarity	NPC485563
0.5086	Remote Similarity	NPC25605
0.5083	Remote Similarity	NPC44716
0.5083	Remote Similarity	NPC488526
0.5083	Remote Similarity	NPC480475
0.5081	Remote Similarity	NPC480473
0.5079	Remote Similarity	NPC472267
0.5079	Remote Similarity	NPC107536
0.5079	Remote Similarity	NPC213952
0.5079	Remote Similarity	NPC115656
0.5079	Remote Similarity	NPC280029
0.5079	Remote Similarity	NPC9470
0.5076	Remote Similarity	NPC286457
0.5042	Remote Similarity	NPC242840
0.5039	Remote Similarity	NPC475287
0.5039	Remote Similarity	NPC251263
0.5039	Remote Similarity	NPC155410
0.5039	Remote Similarity	NPC257211
0.5038	Remote Similarity	NPC478597
0.5038	Remote Similarity	NPC488211
0.5036	Remote Similarity	NPC279915
0.5036	Remote Similarity	NPC476778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC218954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6635
0.1-0.2	2464
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