NPASS Compound

Natural Product: NPC22742

Natural Product ID	NPC22742
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Scammonin Ii
IUPAC Name	n.a.
Synonyms	Scammonin II
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506030
PubChem CID	14704606
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 143147 0 0 0 0 0 0 0 0999 V2000 5.4884 0.5022 4.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5766 1.2008 4.1380 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2064 0.2629 3.1494 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1795 -0.3104 2.1558 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5689 0.8540 1.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5117 0.3838 0.3913 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0509 1.7006 -0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0452 1.6253 -1.2798 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7884 3.0262 -1.8156 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2504 3.8899 -0.7376 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9965 5.3082 -1.1254 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0861 5.5635 -2.2527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2789 4.9969 -2.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0504 5.3922 -0.9295 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4312 4.7610 -0.9991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3474 3.3036 -1.1773 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3126 2.8623 -2.3756 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2994 2.3398 -0.1836 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 1.0065 -0.5799 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6269 0.1435 0.4824 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4240 -1.3043 -0.0707 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2923 -1.2593 -0.7732 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 -2.3717 -1.1401 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3519 -2.7440 -0.0245 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5357 -2.0349 -0.0006 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3613 -2.0896 -1.0717 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7607 -1.7138 -0.6486 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0653 -0.4005 -0.5578 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7035 -2.2440 -1.5866 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9046 -3.5863 -1.4324 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4388 -4.1892 -2.7097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5572 -4.2429 -1.1338 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4891 -3.4078 -1.7458 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9438 -3.1460 -3.0702 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5181 -4.4210 0.2222 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5273 -4.0986 0.1586 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3257 -4.7084 0.3478 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5983 -6.1384 0.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2963 -6.1657 2.0225 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3561 -4.7894 -0.9959 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3438 -3.4842 -1.7371 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1050 -3.7502 -3.0342 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6290 -5.3042 -0.7584 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5810 -1.7431 -0.6621 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1642 -0.9389 -1.5830 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3400 -1.6805 -2.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5550 0.3760 -0.9449 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2888 1.1782 -1.7979 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4987 1.6320 -1.2911 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4961 0.9849 -2.0977 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6515 0.9550 -1.2864 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7154 0.1135 -1.9412 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0762 2.3972 -1.0694 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1695 3.3206 -1.8837 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7110 3.0950 -1.4464 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4335 3.7788 -0.2895 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2989 2.9673 -3.2194 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0112 2.7136 0.2806 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5111 0.0825 1.5849 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0496 0.3664 2.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8365 0.6660 2.9706 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9192 0.3181 4.0582 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2007 0.6064 5.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0812 -0.3633 5.6254 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6191 -1.0257 4.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9155 -0.4232 5.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1384 1.2301 5.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6068 0.2942 4.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3894 1.4715 4.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2387 2.1318 3.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9496 0.8603 2.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7361 -0.5502 3.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7097 -1.0140 1.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3850 -0.7839 2.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 1.4830 2.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3209 1.5040 0.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7501 -0.1330 0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7617 2.3136 0.6760 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9587 2.2281 -0.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0893 1.1398 -0.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4818 0.9798 -2.1008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0219 2.8852 -2.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7307 3.4023 -2.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0100 3.9613 0.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3835 3.3680 -0.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0005 5.7387 -1.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6914 5.9280 -0.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5067 5.2698 -3.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9754 6.6895 -2.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2328 3.9033 -2.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8663 5.4010 -3.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1900 6.4870 -0.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5814 5.1161 0.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9407 5.0071 -0.0452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0545 5.2386 -1.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5668 0.8701 -1.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6390 0.4679 0.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.8780 0.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1139 -1.9692 -1.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8249 -2.4128 0.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0893 -1.3480 -1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0459 -2.2012 0.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6230 -3.7149 -0.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7627 -5.0169 -3.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3851 -4.7233 -2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6126 -3.4730 -3.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5302 -5.2399 -1.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -3.9407 -1.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7933 -2.1899 -3.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9143 -5.2663 0.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3133 -4.2352 1.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3871 -6.6327 0.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1198 -6.6773 0.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9330 -6.9295 1.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1817 -5.5864 -1.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4409 -3.2626 -1.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5481 -4.3759 -3.4317 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9941 -5.5976 -1.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5105 -0.6719 -2.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6906 -1.0834 -3.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9296 -2.6823 -2.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1425 -1.8976 -1.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0956 0.2348 -0.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6917 1.2853 -0.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3651 0.4718 -0.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4887 0.7373 -2.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2536 -0.4591 -1.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2780 -0.5848 -2.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0948 2.5125 -1.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4911 4.3533 -1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1171 3.5317 -2.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5929 4.7566 -0.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1687 2.5752 -3.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9174 2.6521 0.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7368 1.0879 3.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9407 0.5422 6.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7932 1.6512 5.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1174 0.0930 5.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9737 -0.4569 6.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2142 -1.3228 5.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6918 -0.8654 4.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5408 -1.6290 3.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2098 -1.6443 5.0147 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 24 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 21 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 20 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 28 6 1 0 55 49 1 0 47 19 1 0 41 23 1 0 33 26 1 0 1 66 1 0 1 67 1 0 1 68 1 0 2 69 1 0 2 70 1 0 3 71 1 0 3 72 1 0 4 73 1 0 4 74 1 0 5 75 1 0 5 76 1 0 6 77 1 1 7 78 1 0 7 79 1 0 8 80 1 0 8 81 1 0 9 82 1 0 9 83 1 0 10 84 1 0 10 85 1 0 11 86 1 0 11 87 1 0 12 88 1 0 12 89 1 0 13 90 1 0 13 91 1 0 14 92 1 0 14 93 1 0 15 94 1 0 15 95 1 0 19 96 1 6 20 97 1 1 21 98 1 1 23 99 1 6 24100 1 1 26101 1 6 27102 1 1 30103 1 1 31104 1 0 31105 1 0 31106 1 0 32107 1 6 33108 1 6 34109 1 0 35110 1 0 37111 1 1 38112 1 0 38113 1 0 39114 1 0 40115 1 6 41116 1 6 42117 1 0 43118 1 0 45119 1 6 46120 1 0 46121 1 0 46122 1 0 47123 1 1 49124 1 1 51125 1 1 52126 1 0 52127 1 0 52128 1 0 53129 1 6 54130 1 6 55131 1 6 56132 1 0 57133 1 0 58134 1 0 62135 1 6 63136 1 0 63137 1 0 64138 1 0 64139 1 0 64140 1 0 65141 1 0 65142 1 0 65143 1 0 M END

Standard InCHIKey	QHKWTUIZHFKQCZ-QXVRPKQISA-N
Standard InCHI	InChI=1S/C45H78O20/c1-7-9-15-18-26-19-16-13-11-10-12-14-17-20-28(47)61-39-36(63-42-35(54)32(51)29(48)23(4)56-42)25(6)58-45(40(39)62-41(55)22(3)8-2)65-38-34(53)31(50)27(21-46)60-44(38)64-37-33(52)30(49)24(5)57-43(37)59-26/h22-27,29-40,42-46,48-54H,7-21H2,1-6H3/t22-,23+,24+,25-,26-,27+,29+,30+,31+,32-,33-,34-,35+,36-,37+,38+,39+,40+,42-,43-,44-,45-/m0/s1
SMILES	CCCCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@H]([C@H](O[C@H]3[C@H](O[C@H]4[C@H](O1)O[C@H](C)[C@H]([C@@H]4O)O)O[C@H](CO)[C@H]([C@@H]3O)O)O[C@@H](C)[C@@H]2O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)O)OC(=O)[C@H](CC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	938.51	Volume:	914.625 ? Van der Waals volume.
Dense:	1.026	LogP:	3.107 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.746 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.008 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	44.0
TPSA:	288.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.112	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.253	Fsp³:	0.956
MCE-18:	104.591 ? 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:	0.928	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.501	Promiscuous compounds:	0.204

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.822	MDCK Permeability:	-4.975
Pgp-inhibitor:	0.0	Pgp-substrate:	0.681
PAMPA:	0.974 ? 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):	0.01
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.483
Plasma Protein Binding (PPB):	72.276%	Volume Distribution (VD):	-0.344
Fu:	19.368% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
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:	0.113
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.989 ? 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):

0.83

Half-life (T1/2):

3.507

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.095
Human Hepatotoxicity (H-HT):	0.542	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.561	Drug-induced Nephrotoxicity:	0.978
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.618
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.191
BCF:	0.604 ? 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:	3.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.952 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.878 ? 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
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	DOI[10.1016/S0040-4020(97)00607-8]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496705]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	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
ED50	4
MIC	4

Activity Type	# Activity
Cell line	3
Organism	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
NPT91	Cell line	KB	Homo sapiens	ED50	=	7.0	ug ml-1	PMID[3681902]
NPT5198	Cell line	OVCAR	Homo sapiens	ED50	>	15.0	ug ml-1	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	ED50	>	15.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	15.0	ug ml-1	PMID[10479311]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	PMID[7783142]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	512.0	ug.mL-1	PMID[22687745]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[26988802]

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 NPC22742 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	21527
0.1-0.2	23934
0.2-0.3	3885
0.3-0.4	373
0.4-0.5	19
0.5-0.6	29
0.6-0.7	52
0.7-0.8	0
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477346
0.8714	High Similarity	NPC477350
0.84	Intermediate Similarity	NPC478734
0.8333	Intermediate Similarity	NPC472204
0.8312	Intermediate Similarity	NPC146992
0.8312	Intermediate Similarity	NPC85759
0.8182	Intermediate Similarity	NPC478733
0.8158	Intermediate Similarity	NPC89843
0.8133	Intermediate Similarity	NPC477349
0.8101	Intermediate Similarity	NPC294748
0.8052	Intermediate Similarity	NPC477344
0.8025	Intermediate Similarity	NPC184915
0.7975	Intermediate Similarity	NPC297768
0.7975	Intermediate Similarity	NPC173328
0.7901	Intermediate Similarity	NPC238056
0.7831	Intermediate Similarity	NPC44782
0.7805	Intermediate Similarity	NPC224953
0.7778	Intermediate Similarity	NPC238264
0.7778	Intermediate Similarity	NPC477345
0.7654	Intermediate Similarity	NPC119583
0.7654	Intermediate Similarity	NPC186992
0.7595	Intermediate Similarity	NPC158302
0.759	Intermediate Similarity	NPC259294
0.759	Intermediate Similarity	NPC126685
0.7531	Intermediate Similarity	NPC477319
0.747	Intermediate Similarity	NPC115013
0.7439	Intermediate Similarity	NPC143421
0.7381	Intermediate Similarity	NPC183888
0.7349	Intermediate Similarity	NPC483170
0.7342	Intermediate Similarity	NPC604005
0.7342	Intermediate Similarity	NPC605014
0.7262	Intermediate Similarity	NPC169345
0.7262	Intermediate Similarity	NPC290012
0.7229	Intermediate Similarity	NPC307400
0.7229	Intermediate Similarity	NPC27289
0.716	Intermediate Similarity	NPC600446
0.716	Intermediate Similarity	NPC605013
0.7037	Intermediate Similarity	NPC477331
0.6941	Remote Similarity	NPC478726
0.6923	Remote Similarity	NPC146380
0.6897	Remote Similarity	NPC123204
0.6867	Remote Similarity	NPC109887
0.6768	Remote Similarity	NPC472352
0.675	Remote Similarity	NPC281563
0.6747	Remote Similarity	NPC477326
0.6744	Remote Similarity	NPC476087
0.6744	Remote Similarity	NPC475667
0.6705	Remote Similarity	NPC472200
0.6667	Remote Similarity	NPC478732
0.6667	Remote Similarity	NPC477317
0.6667	Remote Similarity	NPC477318
0.6591	Remote Similarity	NPC475270
0.6591	Remote Similarity	NPC475327
0.6588	Remote Similarity	NPC267592
0.6585	Remote Similarity	NPC113745
0.6585	Remote Similarity	NPC477320
0.6585	Remote Similarity	NPC477323
0.6585	Remote Similarity	NPC477325
0.6585	Remote Similarity	NPC609436
0.6538	Remote Similarity	NPC478729
0.6538	Remote Similarity	NPC606819
0.6522	Remote Similarity	NPC475241
0.6512	Remote Similarity	NPC472205
0.6512	Remote Similarity	NPC478724
0.65	Remote Similarity	NPC475425
0.6495	Remote Similarity	NPC290276
0.6421	Remote Similarity	NPC63404
0.6395	Remote Similarity	NPC478725
0.6374	Remote Similarity	NPC475164
0.6374	Remote Similarity	NPC478728
0.6341	Remote Similarity	NPC477329
0.6322	Remote Similarity	NPC478723
0.6304	Remote Similarity	NPC478727
0.6286	Remote Similarity	NPC206823
0.6264	Remote Similarity	NPC269318
0.625	Remote Similarity	NPC35338
0.625	Remote Similarity	NPC204214
0.625	Remote Similarity	NPC92283
0.6235	Remote Similarity	NPC477332
0.622	Remote Similarity	NPC477328
0.622	Remote Similarity	NPC477330
0.6207	Remote Similarity	NPC478722
0.6176	Remote Similarity	NPC600940
0.6162	Remote Similarity	NPC10883
0.6129	Remote Similarity	NPC473605
0.6129	Remote Similarity	NPC475375
0.6067	Remote Similarity	NPC478730
0.602	Remote Similarity	NPC28069
0.6	Remote Similarity	NPC10121
0.6	Remote Similarity	NPC198918
0.598	Remote Similarity	NPC600721
0.598	Remote Similarity	NPC605872
0.5977	Remote Similarity	NPC216883
0.5955	Remote Similarity	NPC476781
0.5859	Remote Similarity	NPC77651
0.5842	Remote Similarity	NPC611287
0.5816	Remote Similarity	NPC124878
0.5816	Remote Similarity	NPC231888
0.5806	Remote Similarity	NPC163409
0.5806	Remote Similarity	NPC475525
0.5806	Remote Similarity	NPC475540
0.5784	Remote Similarity	NPC610996
0.5761	Remote Similarity	NPC478731
0.5745	Remote Similarity	NPC476066
0.5625	Remote Similarity	NPC147032
0.5556	Remote Similarity	NPC471024
0.5514	Remote Similarity	NPC471026
0.5495	Remote Similarity	NPC479061
0.5435	Remote Similarity	NPC44682
0.5435	Remote Similarity	NPC479060
0.5361	Remote Similarity	NPC476783
0.5333	Remote Similarity	NPC600672
0.5258	Remote Similarity	NPC477347
0.5253	Remote Similarity	NPC477348
0.5152	Remote Similarity	NPC476782
0.514	Remote Similarity	NPC471025
0.5138	Remote Similarity	NPC610997
0.5135	Remote Similarity	NPC241265
0.5109	Remote Similarity	NPC479059

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7160
0.1-0.2	1902
0.2-0.3	83
0.3-0.4	5
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