NPASS Compound

Natural Product: NPC292677

Natural Product ID	NPC292677
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Glucopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Alpha-L-Arabinopyranosyl]Olean-12-Ene-28Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL475806
PubChem CID	11722070
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 11.4926 -0.4167 -3.3682 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6394 -0.8432 -2.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9586 0.3867 -1.7577 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0953 0.0021 -0.7397 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2311 1.0773 -0.4733 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7157 0.9699 0.8215 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3392 0.7326 0.7694 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9791 -0.5877 1.3719 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4558 -0.6081 2.6936 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4821 -0.7846 1.3356 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0249 -1.3753 0.1628 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6858 -2.6882 0.2995 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3382 -3.0090 -0.1882 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2268 -4.4412 -0.3775 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7890 -4.6890 -1.6331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0342 -3.8356 -1.8305 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6712 -3.5932 -0.4614 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7796 -4.8242 0.1532 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8932 -4.5634 -2.6537 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3474 -2.6498 0.7246 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2338 -2.0689 0.0789 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8780 -3.0621 0.2737 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2264 -2.5107 0.0192 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4551 -1.2087 0.8167 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4196 -0.1963 0.4391 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0054 -0.6887 0.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 -0.4540 1.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7732 0.2173 -0.4583 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 1.0732 1.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9896 1.6717 0.7254 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1127 0.6791 0.8283 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7675 -0.6658 0.2692 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8936 -1.6080 0.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2017 -0.9816 0.4754 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4880 0.2927 0.3708 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3029 1.1625 -0.0090 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0622 0.9332 -1.4761 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5762 2.5976 0.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9162 3.0369 -0.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0882 2.2228 0.1583 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8043 0.8446 0.6462 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9859 -0.0403 0.3719 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4703 -0.0982 -1.0229 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9978 0.0662 -1.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1995 -1.4172 -1.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9200 1.0707 -1.8329 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1054 2.2854 -0.9613 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7090 3.0074 1.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8859 3.3728 1.1872 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9870 3.3170 2.4263 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5906 0.6735 2.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4987 -1.5916 2.2461 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7681 0.2764 1.8034 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0906 1.4927 1.2222 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5643 1.8378 1.4501 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8387 3.0343 0.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2349 2.6195 1.6993 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8569 2.4176 -0.7038 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3582 2.4305 -0.5029 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0347 1.2560 -1.1233 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0572 1.5751 -1.9830 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6633 2.5660 0.8693 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5427 2.9736 -1.9296 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0785 -0.2982 -4.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2054 -1.3822 -1.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8741 -1.4785 -2.8552 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3949 0.8948 -2.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3993 0.9561 -1.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0201 0.7030 -0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5201 -1.4049 0.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9741 -0.0057 3.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3343 -1.6239 2.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7876 -3.0534 1.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1391 -2.6371 -1.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0802 -4.4650 -2.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0544 -5.7546 -1.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7914 -2.9096 -2.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6171 -3.0740 -0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6865 -5.1920 0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8851 -4.2111 -3.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4807 -2.0757 -1.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7506 -3.5950 1.2410 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7141 -3.8784 -0.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3448 -2.3192 -1.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9968 -3.2180 0.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6062 0.0141 -0.6580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0399 0.5707 1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4591 -1.1444 2.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1302 -0.4636 2.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2541 1.1525 -0.6674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7799 0.4371 -0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8367 -0.3092 -1.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6227 0.9913 2.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8840 1.8098 0.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1885 2.5269 1.4044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8656 2.0994 -0.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5001 -0.4630 -0.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9290 -2.1350 -0.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7981 -2.4543 0.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0168 -1.6802 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6729 1.6641 -2.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0193 1.1776 -1.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3736 -0.0644 -1.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8231 3.1761 -0.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4456 2.9626 1.2389 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0230 4.1107 0.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8500 3.1315 -1.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8241 0.9245 1.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9148 -1.0523 0.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8274 0.4328 0.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3308 0.5915 -1.9634 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3162 0.6920 -0.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5125 -0.8977 -0.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8995 -1.4768 -2.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5107 -2.2105 -1.0063 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1843 -1.5194 -2.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5534 1.2030 -2.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8774 0.8622 -2.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1231 2.3192 -0.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9503 3.1938 -1.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1663 4.2049 2.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5252 1.2829 2.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8238 -0.2953 2.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8567 1.1838 2.9364 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4085 -2.1948 2.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6603 -2.2807 2.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4939 -0.7736 2.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9486 1.4112 0.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7590 1.8734 2.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1237 3.7163 1.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7916 3.5721 1.5159 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3062 2.6727 1.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 2.5941 2.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4558 3.1195 0.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7277 3.3585 -0.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4484 0.6344 -0.2799 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9454 1.2841 -1.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4037 1.9926 1.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0466 3.8222 -1.8244 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 8 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 16 19 1 0 13 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 26 28 1 0 25 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 2 0 35 36 1 0 36 37 1 6 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 43 46 1 0 46 47 1 0 40 48 1 1 48 49 2 0 48 50 1 0 31 51 1 1 24 52 1 1 10 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 5 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 58 63 1 0 60 3 1 0 55 7 1 0 17 12 1 0 26 21 1 0 36 31 1 0 47 40 1 0 32 24 1 0 41 35 1 0 1 64 1 0 2 65 1 0 2 66 1 0 3 67 1 6 5 68 1 6 7 69 1 6 8 70 1 6 9 71 1 0 10 72 1 1 12 73 1 1 13 74 1 6 15 75 1 0 15 76 1 0 16 77 1 6 17 78 1 6 18 79 1 0 19 80 1 0 21 81 1 6 22 82 1 0 22 83 1 0 23 84 1 0 23 85 1 0 25 86 1 6 27 87 1 0 27 88 1 0 27 89 1 0 28 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 0 30 96 1 0 32 97 1 6 33 98 1 0 33 99 1 0 34100 1 0 37101 1 0 37102 1 0 37103 1 0 38104 1 0 38105 1 0 39106 1 0 39107 1 0 41108 1 1 42109 1 0 42110 1 0 44111 1 0 44112 1 0 44113 1 0 45114 1 0 45115 1 0 45116 1 0 46117 1 0 46118 1 0 47119 1 0 47120 1 0 50121 1 0 51122 1 0 51123 1 0 51124 1 0 52125 1 0 52126 1 0 52127 1 0 54128 1 6 55129 1 1 56130 1 0 57131 1 0 57132 1 0 57133 1 0 58134 1 1 59135 1 6 60136 1 1 61137 1 0 62138 1 0 63139 1 0 M END

Standard InCHIKey	OHJWWOZXCKEOGK-YDOLDEOXSA-N
Standard InCHI	InChI=1S/C47H76O16/c1-22-30(50)36(62-38-34(54)33(53)32(52)26(20-48)60-38)35(55)39(59-22)63-37-31(51)25(49)21-58-40(37)61-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57)/t22-,24-,25-,26+,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+,37+,38-,39-,40-,44-,45+,46+,47-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@H](O[C@H]3[C@@H](OC[C@@H]([C@@H]3O)O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]3([C@@H]4CC=C4[C@@]3(C)CC[C@@]3([C@H]4CC(C)(C)CC3)C(=O)O)C)C)O[C@H]([C@@H]2O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	896.51	Volume:	888.387 ? Van der Waals volume.
Dense:	1.009	LogP:	2.089 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.638 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.812 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.181	Fsp³:	0.936
MCE-18:	171.692 ? 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:	0.93	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.204	Promiscuous compounds:	0.145

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.114	MDCK Permeability:	-5.178
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
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):	0.236
20% Bioavailability (F20%):	0.134	30% Bioavailability (F30%):	0.955
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069	MRP1:	0.032
Plasma Protein Binding (PPB):	76.401%	Volume Distribution (VD):	-0.473
Fu:	15.693% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.259
HLM stability:	0.001 ? 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):

-0.032

Half-life (T1/2):

3.646

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.792	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.779	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.178	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.657	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.254	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.604	Hek293 Cytotoxicity:	0.403
BCF:	1.543 ? 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:	3.962 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.573 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.752 ? 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
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO33015	trevesia palmata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757708]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30520	Patrinia scabiosaefolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30520	Patrinia scabiosaefolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30520	Patrinia scabiosaefolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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
IC50	4

Activity Type	# Activity
Cell line	4

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[10514313]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	12100.0	nM	PMID[23639650]
NPT81	Cell line	A549	Homo sapiens	IC50	=	16700.0	nM	PMID[23639650]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6100.0	nM	PMID[23639650]

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 NPC292677 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	23521
0.1-0.2	22007
0.2-0.3	2884
0.3-0.4	802
0.4-0.5	427
0.5-0.6	120
0.6-0.7	40
0.7-0.8	0
0.8-0.85	6
0.85-0.9	6
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324875
0.9271	High Similarity	NPC276093
0.9208	High Similarity	NPC219180
0.9208	High Similarity	NPC251263
0.8925	High Similarity	NPC127056
0.8866	High Similarity	NPC481082
0.8866	High Similarity	NPC164419
0.8654	High Similarity	NPC166422
0.8614	High Similarity	NPC475486
0.8558	High Similarity	NPC133818
0.8421	Intermediate Similarity	NPC56713
0.8229	Intermediate Similarity	NPC59804
0.8182	Intermediate Similarity	NPC114304
0.8148	Intermediate Similarity	NPC54636
0.8108	Intermediate Similarity	NPC161717
0.8037	Intermediate Similarity	NPC323341
0.7941	Intermediate Similarity	NPC257468
0.7857	Intermediate Similarity	NPC174679
0.7857	Intermediate Similarity	NPC279554
0.7732	Intermediate Similarity	NPC164194
0.7677	Intermediate Similarity	NPC25605
0.7624	Intermediate Similarity	NPC80843
0.7573	Intermediate Similarity	NPC180550
0.7573	Intermediate Similarity	NPC35405
0.7525	Intermediate Similarity	NPC488561
0.7478	Intermediate Similarity	NPC471385
0.7447	Intermediate Similarity	NPC606107
0.7387	Intermediate Similarity	NPC471384
0.7374	Intermediate Similarity	NPC270667
0.7358	Intermediate Similarity	NPC79718
0.7353	Intermediate Similarity	NPC472949
0.7333	Intermediate Similarity	NPC139044
0.7315	Intermediate Similarity	NPC488564
0.7255	Intermediate Similarity	NPC109079
0.7238	Intermediate Similarity	NPC104400
0.7238	Intermediate Similarity	NPC10320
0.7115	Intermediate Similarity	NPC22956
0.7064	Intermediate Similarity	NPC323359
0.7059	Intermediate Similarity	NPC12288
0.6804	Remote Similarity	NPC204407
0.6789	Remote Similarity	NPC275668
0.6789	Remote Similarity	NPC475504
0.6786	Remote Similarity	NPC481078
0.6762	Remote Similarity	NPC114441
0.6754	Remote Similarity	NPC475287
0.6735	Remote Similarity	NPC283849
0.6729	Remote Similarity	NPC469945
0.6727	Remote Similarity	NPC119794
0.6726	Remote Similarity	NPC62725
0.6697	Remote Similarity	NPC471383
0.6696	Remote Similarity	NPC79643
0.6667	Remote Similarity	NPC288205
0.6667	Remote Similarity	NPC51465
0.6667	Remote Similarity	NPC476992
0.6579	Remote Similarity	NPC280941
0.6579	Remote Similarity	NPC235772
0.6571	Remote Similarity	NPC136877
0.6542	Remote Similarity	NPC6377
0.6542	Remote Similarity	NPC208381
0.6441	Remote Similarity	NPC123199
0.6283	Remote Similarity	NPC488515
0.6275	Remote Similarity	NPC31839
0.6273	Remote Similarity	NPC112352
0.6261	Remote Similarity	NPC488209
0.626	Remote Similarity	NPC41061
0.626	Remote Similarity	NPC227551
0.625	Remote Similarity	NPC258885
0.625	Remote Similarity	NPC91838
0.6238	Remote Similarity	NPC28198
0.6238	Remote Similarity	NPC476123
0.6195	Remote Similarity	NPC73829
0.619	Remote Similarity	NPC191410
0.616	Remote Similarity	NPC305981
0.616	Remote Similarity	NPC111466
0.6148	Remote Similarity	NPC488211
0.6111	Remote Similarity	NPC261506
0.6111	Remote Similarity	NPC4328
0.6055	Remote Similarity	NPC475296
0.6017	Remote Similarity	NPC480939
0.5968	Remote Similarity	NPC21691
0.5966	Remote Similarity	NPC475119
0.5962	Remote Similarity	NPC286347
0.5952	Remote Similarity	NPC293330
0.5905	Remote Similarity	NPC100383
0.5891	Remote Similarity	NPC220160
0.5891	Remote Similarity	NPC488212
0.5847	Remote Similarity	NPC187618
0.5839	Remote Similarity	NPC40085
0.5833	Remote Similarity	NPC475472
0.5826	Remote Similarity	NPC63159
0.5804	Remote Similarity	NPC488516
0.5789	Remote Similarity	NPC160415
0.5785	Remote Similarity	NPC473824
0.5781	Remote Similarity	NPC236638
0.5781	Remote Similarity	NPC294453
0.578	Remote Similarity	NPC211798
0.5766	Remote Similarity	NPC474589
0.5763	Remote Similarity	NPC291903
0.576	Remote Similarity	NPC4749
0.5755	Remote Similarity	NPC242611
0.5739	Remote Similarity	NPC164389
0.5738	Remote Similarity	NPC151543
0.5736	Remote Similarity	NPC298034
0.5736	Remote Similarity	NPC71065
0.5669	Remote Similarity	NPC110633
0.5659	Remote Similarity	NPC481081
0.5648	Remote Similarity	NPC284807
0.5643	Remote Similarity	NPC264270
0.5615	Remote Similarity	NPC302543
0.5606	Remote Similarity	NPC250247
0.5603	Remote Similarity	NPC480475
0.56	Remote Similarity	NPC283417
0.56	Remote Similarity	NPC200049
0.56	Remote Similarity	NPC475140
0.5583	Remote Similarity	NPC480474
0.5581	Remote Similarity	NPC43550
0.5567	Remote Similarity	NPC120840
0.5528	Remote Similarity	NPC313110
0.552	Remote Similarity	NPC135904
0.55	Remote Similarity	NPC301449
0.55	Remote Similarity	NPC601290
0.5478	Remote Similarity	NPC263756
0.5478	Remote Similarity	NPC213674
0.5472	Remote Similarity	NPC57362
0.547	Remote Similarity	NPC251768
0.5462	Remote Similarity	NPC302887
0.5455	Remote Similarity	NPC480473
0.5431	Remote Similarity	NPC192791
0.5426	Remote Similarity	NPC265841
0.5426	Remote Similarity	NPC488308
0.542	Remote Similarity	NPC136768
0.542	Remote Similarity	NPC202828
0.542	Remote Similarity	NPC119592
0.5417	Remote Similarity	NPC114484
0.5391	Remote Similarity	NPC481080
0.5385	Remote Similarity	NPC124296
0.5385	Remote Similarity	NPC312650
0.5372	Remote Similarity	NPC218954
0.5372	Remote Similarity	NPC75318
0.5364	Remote Similarity	NPC475633
0.5364	Remote Similarity	NPC473538
0.5354	Remote Similarity	NPC191827
0.5351	Remote Similarity	NPC108748
0.5349	Remote Similarity	NPC57484
0.5345	Remote Similarity	NPC469946
0.5339	Remote Similarity	NPC159309
0.5339	Remote Similarity	NPC473383
0.5339	Remote Similarity	NPC86222
0.5333	Remote Similarity	NPC484832
0.5328	Remote Similarity	NPC160452
0.5304	Remote Similarity	NPC480424
0.5299	Remote Similarity	NPC223301
0.5299	Remote Similarity	NPC488309
0.5299	Remote Similarity	NPC171544
0.5294	Remote Similarity	NPC475591
0.5294	Remote Similarity	NPC236870
0.5289	Remote Similarity	NPC37134
0.5285	Remote Similarity	NPC187290
0.528	Remote Similarity	NPC60557
0.528	Remote Similarity	NPC67857
0.5271	Remote Similarity	NPC85154
0.5271	Remote Similarity	NPC71391
0.5268	Remote Similarity	NPC473481
0.5267	Remote Similarity	NPC271610
0.5254	Remote Similarity	NPC204392
0.525	Remote Similarity	NPC123796
0.5246	Remote Similarity	NPC481079
0.5246	Remote Similarity	NPC23275
0.5242	Remote Similarity	NPC480936
0.5231	Remote Similarity	NPC484061
0.5231	Remote Similarity	NPC484062
0.5227	Remote Similarity	NPC65105
0.5225	Remote Similarity	NPC294112
0.5221	Remote Similarity	NPC76999
0.5217	Remote Similarity	NPC475516
0.521	Remote Similarity	NPC44716
0.521	Remote Similarity	NPC173859
0.521	Remote Similarity	NPC148603
0.521	Remote Similarity	NPC46665
0.5207	Remote Similarity	NPC64715
0.5197	Remote Similarity	NPC470911
0.5164	Remote Similarity	NPC104372
0.5161	Remote Similarity	NPC469947
0.5161	Remote Similarity	NPC104137
0.5161	Remote Similarity	NPC26626
0.5161	Remote Similarity	NPC480948
0.5159	Remote Similarity	NPC610204
0.5154	Remote Similarity	NPC192765
0.5128	Remote Similarity	NPC470512
0.5126	Remote Similarity	NPC117714
0.5126	Remote Similarity	NPC30289
0.5124	Remote Similarity	NPC297263
0.512	Remote Similarity	NPC11242
0.512	Remote Similarity	NPC75287
0.512	Remote Similarity	NPC470915
0.5116	Remote Similarity	NPC470218
0.5116	Remote Similarity	NPC471550
0.5115	Remote Similarity	NPC178264
0.5082	Remote Similarity	NPC471435

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC292677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6882
0.1-0.2	2206
0.2-0.3	53
0.3-0.4	8
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