NPASS Compound

Natural Product: NPC160415

Natural Product ID	NPC160415
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Latifoloside A
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505407
PubChem CID	44566331
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 -8.8619 -0.1687 5.4608 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3499 -0.6238 4.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6340 0.4765 3.4998 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1335 -0.0135 2.2960 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3768 0.8507 1.2419 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7484 0.3406 0.0858 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 1.0939 -0.6166 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5891 2.2433 -0.1369 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1334 0.5807 -1.8502 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2380 0.3554 -2.8623 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9587 -0.9377 -2.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0177 -2.0963 -2.8377 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5596 -1.6612 -2.6903 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4900 -0.7251 -1.5221 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0949 -0.5798 -0.9908 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6851 -1.5142 -0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3336 -1.5479 0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4494 -0.6024 -0.2476 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1073 0.7170 -0.3374 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2129 0.5623 -1.4015 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0191 1.8182 -1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2296 1.6497 -2.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6049 0.2476 -2.7221 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8926 1.0332 0.9455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2598 1.8923 -0.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2070 1.7150 -0.4762 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7233 0.3371 -0.6441 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9931 -0.6188 0.2183 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0991 -0.3046 1.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4889 -2.0042 -0.0250 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7978 -2.1530 -0.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8042 -1.0525 -0.4910 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2163 0.3109 -0.5990 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7926 1.2080 0.4562 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7034 0.9277 -1.9240 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4067 -1.2901 0.7350 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7200 -1.6708 0.6845 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7954 -2.9903 1.1695 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1057 -3.4354 1.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9423 -2.6270 2.1927 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0426 -1.5456 2.7527 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5569 -0.7448 1.5273 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6548 -0.2436 0.8326 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6948 1.1322 0.9482 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5804 1.7890 -0.2644 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5573 1.4599 -1.1838 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7479 2.6940 -2.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8900 1.1648 -0.5588 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0400 1.9232 0.7262 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9688 1.4903 1.6892 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7188 2.5496 2.5627 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9585 3.3020 0.5364 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0451 -0.1960 -0.2835 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9399 -2.1202 3.3404 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4344 -3.3691 3.2424 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7909 -2.9431 -2.4670 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2032 -1.0832 -3.9068 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2272 -2.8574 -4.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8795 0.9068 1.0681 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4197 1.7149 2.2150 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4691 1.7072 3.3658 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6819 2.8702 3.4289 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7086 1.3574 2.5648 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2318 1.4770 -0.1583 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8279 -0.3805 5.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6700 -1.4666 4.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1751 -1.0234 3.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7424 0.7502 4.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9983 1.8748 1.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0017 1.1738 -2.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8997 0.5100 -3.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4322 -0.9698 -1.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7290 -0.9918 -3.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1967 -2.8231 -2.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1495 -1.2039 -0.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3606 -2.3441 0.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0006 -2.6040 0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4652 -1.3180 1.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3944 -1.0228 -1.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3243 2.2114 -0.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4233 2.6301 -1.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9911 1.5798 -3.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8040 2.6208 -2.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1582 0.7111 -3.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5567 0.5760 -2.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5815 -0.8587 -2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9189 0.6714 0.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 0.7011 1.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9574 2.1592 1.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4471 2.2185 -1.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5680 2.7850 -0.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5098 2.1066 0.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7581 2.3642 -1.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4438 0.0464 -1.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0854 -0.7424 2.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3473 -0.8913 2.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1261 0.7520 1.9324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5635 -2.5838 0.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7020 -2.5930 -0.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2438 -3.1384 -0.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5932 -2.3051 -1.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5916 -1.2242 -1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7735 0.8276 1.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 2.2709 0.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9034 1.2544 0.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8046 2.0295 -1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6870 0.4825 -2.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9675 0.6433 -2.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0775 -1.6705 -0.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0786 -4.4763 1.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5451 -3.4766 0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7227 -2.1096 1.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5318 -0.8829 3.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0091 0.1059 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8405 1.5111 1.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2372 0.6350 -1.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7649 2.7192 -2.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6462 3.5865 -1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9472 2.7758 -2.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7211 1.4704 -1.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0381 1.6606 1.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3636 0.6266 2.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4797 2.2095 3.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0973 3.7121 1.4431 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0118 -0.3209 -0.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0948 -1.7136 2.9892 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9774 -4.1476 2.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2523 -3.5914 -1.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7405 -2.8203 -2.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8261 -3.5119 -3.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6091 -1.6979 -4.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2138 -2.6569 -4.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4559 -2.5175 -4.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1022 -3.9498 -3.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2710 -0.1166 1.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4587 2.7794 1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1026 1.7560 4.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2748 3.5941 3.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3625 1.7203 1.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1497 1.1539 -0.3713 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 2 0 9 7 1 1 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 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 6 19 24 1 1 19 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 32 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 41 54 1 0 40 55 1 0 13 56 1 0 13 57 1 6 12 58 1 0 5 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 59 64 1 0 61 3 1 0 22 9 1 0 33 27 1 0 42 37 1 0 50 44 1 0 14 9 1 0 20 15 1 0 28 18 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 1 5 69 1 1 10 70 1 0 10 71 1 0 11 72 1 0 11 73 1 0 12 74 1 1 14 75 1 1 16 76 1 0 17 77 1 0 17 78 1 0 18 79 1 6 21 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 0 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 25 91 1 0 26 92 1 0 26 93 1 0 27 94 1 6 29 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 0 31101 1 0 32102 1 6 34103 1 0 34104 1 0 34105 1 0 35106 1 0 35107 1 0 35108 1 0 37109 1 6 39110 1 0 39111 1 0 40112 1 6 41113 1 1 42114 1 1 44115 1 1 46116 1 6 47117 1 0 47118 1 0 47119 1 0 48120 1 6 49121 1 1 50122 1 1 51123 1 0 52124 1 0 53125 1 0 54126 1 0 55127 1 0 56128 1 0 56129 1 0 56130 1 0 57131 1 0 58132 1 0 58133 1 0 58134 1 0 59135 1 6 60136 1 6 61137 1 1 62138 1 0 63139 1 0 64140 1 0 M END

Standard InCHIKey	WZIPJKRPXMPATM-YNLCWPSQSA-N
Standard InCHI	InChI=1S/C47H76O17/c1-21-11-16-47(41(57)64-39-35(56)33(54)31(52)25(19-48)61-39)18-17-44(6)23(37(47)46(21,8)58)9-10-27-43(5)14-13-28(42(3,4)26(43)12-15-45(27,44)7)62-40-36(30(51)24(49)20-59-40)63-38-34(55)32(53)29(50)22(2)60-38/h9,21-22,24-40,48-56,58H,10-20H2,1-8H3/t21-,22+,24+,25-,26+,27-,28+,29+,30+,31-,32-,33+,34-,35-,36-,37-,38+,39+,40+,43+,44-,45-,46-,47+/m1/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)O)(C)O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	912.51	Volume:	897.177 ? Van der Waals volume.
Dense:	1.017	LogP:	2.162 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.743 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.886 ? 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:	0.096	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.338	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:	0.772	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.169	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.344	MDCK Permeability:	-5.036
Pgp-inhibitor:	0.0	Pgp-substrate:	0.034
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):	0.732
20% Bioavailability (F20%):	0.707	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.002
Plasma Protein Binding (PPB):	63.358%	Volume Distribution (VD):	-0.337
Fu:	25.326% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.139
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:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.728
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):

0.111

Half-life (T1/2):

4.241

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.669	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.893	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.101	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.579	Drug-induced Nephrotoxicity:	0.989
Genotoxicity:	0.506	RPMI-8226 Immunitoxicity:	0.259
A549 Cytotoxicity:	0.835	Hek293 Cytotoxicity:	0.574
BCF:	1.808 ? 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:	4.144 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.715 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.91 ? 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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16252920]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	72.8	%	PMID[10479318]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC160415 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	22436
0.1-0.2	22930
0.2-0.3	3096
0.3-0.4	785
0.4-0.5	391
0.5-0.6	131
0.6-0.7	57
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC68175
0.8211	Intermediate Similarity	NPC112352
0.802	Intermediate Similarity	NPC36831
0.7935	Intermediate Similarity	NPC204458
0.7347	Intermediate Similarity	NPC58448
0.7255	Intermediate Similarity	NPC63159
0.7188	Intermediate Similarity	NPC189884
0.7188	Intermediate Similarity	NPC138334
0.7157	Intermediate Similarity	NPC480475
0.7091	Intermediate Similarity	NPC135904
0.7009	Intermediate Similarity	NPC481078
0.6909	Remote Similarity	NPC79643
0.6907	Remote Similarity	NPC47063
0.6863	Remote Similarity	NPC161674
0.6827	Remote Similarity	NPC46665
0.6818	Remote Similarity	NPC60557
0.6818	Remote Similarity	NPC67857
0.6818	Remote Similarity	NPC268184
0.6796	Remote Similarity	NPC75417
0.6774	Remote Similarity	NPC46388
0.6699	Remote Similarity	NPC469946
0.6637	Remote Similarity	NPC123199
0.6632	Remote Similarity	NPC37739
0.661	Remote Similarity	NPC305981
0.6555	Remote Similarity	NPC261506
0.6555	Remote Similarity	NPC4328
0.6549	Remote Similarity	NPC165204
0.6514	Remote Similarity	NPC481079
0.6509	Remote Similarity	NPC164389
0.6455	Remote Similarity	NPC480473
0.6455	Remote Similarity	NPC480474
0.6441	Remote Similarity	NPC41061
0.6441	Remote Similarity	NPC227551
0.641	Remote Similarity	NPC57484
0.6392	Remote Similarity	NPC310014
0.6392	Remote Similarity	NPC269315
0.6389	Remote Similarity	NPC297263
0.6372	Remote Similarity	NPC475287
0.6364	Remote Similarity	NPC128925
0.6356	Remote Similarity	NPC110633
0.6327	Remote Similarity	NPC271138
0.6239	Remote Similarity	NPC222580
0.6239	Remote Similarity	NPC475504
0.6228	Remote Similarity	NPC76972
0.6228	Remote Similarity	NPC469782
0.6228	Remote Similarity	NPC204414
0.6216	Remote Similarity	NPC301449
0.6216	Remote Similarity	NPC601290
0.6214	Remote Similarity	NPC48499
0.6204	Remote Similarity	NPC251768
0.6198	Remote Similarity	NPC236638
0.6198	Remote Similarity	NPC294453
0.6176	Remote Similarity	NPC90856
0.6168	Remote Similarity	NPC192791
0.6154	Remote Similarity	NPC471550
0.6147	Remote Similarity	NPC148417
0.6117	Remote Similarity	NPC78046
0.6116	Remote Similarity	NPC293330
0.6106	Remote Similarity	NPC31838
0.6066	Remote Similarity	NPC136768
0.6038	Remote Similarity	NPC127056
0.6019	Remote Similarity	NPC214484
0.6016	Remote Similarity	NPC298034
0.6016	Remote Similarity	NPC71065
0.6	Remote Similarity	NPC475591
0.6	Remote Similarity	NPC236870
0.6	Remote Similarity	NPC250247
0.6	Remote Similarity	NPC21691
0.5984	Remote Similarity	NPC43550
0.5965	Remote Similarity	NPC187290
0.5943	Remote Similarity	NPC56713
0.5943	Remote Similarity	NPC475516
0.5909	Remote Similarity	NPC10607
0.5902	Remote Similarity	NPC258617
0.5877	Remote Similarity	NPC295823
0.5877	Remote Similarity	NPC174720
0.5877	Remote Similarity	NPC475467
0.5849	Remote Similarity	NPC18233
0.5841	Remote Similarity	NPC114484
0.5833	Remote Similarity	NPC39211
0.5818	Remote Similarity	NPC309714
0.5806	Remote Similarity	NPC481081
0.5794	Remote Similarity	NPC235405
0.5794	Remote Similarity	NPC220160
0.5789	Remote Similarity	NPC324875
0.5789	Remote Similarity	NPC292677
0.578	Remote Similarity	NPC80843
0.575	Remote Similarity	NPC283417
0.575	Remote Similarity	NPC200049
0.5741	Remote Similarity	NPC249848
0.5741	Remote Similarity	NPC107966
0.5739	Remote Similarity	NPC187618
0.5739	Remote Similarity	NPC80986
0.5728	Remote Similarity	NPC256798
0.5727	Remote Similarity	NPC223301
0.5727	Remote Similarity	NPC171544
0.568	Remote Similarity	NPC202828
0.568	Remote Similarity	NPC119592
0.5676	Remote Similarity	NPC30735
0.5636	Remote Similarity	NPC263756
0.5625	Remote Similarity	NPC173859
0.5625	Remote Similarity	NPC148603
0.562	Remote Similarity	NPC475160
0.562	Remote Similarity	NPC100639
0.562	Remote Similarity	NPC470218
0.562	Remote Similarity	NPC473714
0.5575	Remote Similarity	NPC235438
0.5565	Remote Similarity	NPC104372
0.5565	Remote Similarity	NPC286457
0.5556	Remote Similarity	NPC104137
0.5556	Remote Similarity	NPC475486
0.5556	Remote Similarity	NPC26626
0.5545	Remote Similarity	NPC295371
0.5545	Remote Similarity	NPC157868
0.5528	Remote Similarity	NPC4749
0.5528	Remote Similarity	NPC481080
0.5526	Remote Similarity	NPC257468
0.5514	Remote Similarity	NPC1046
0.5508	Remote Similarity	NPC470915
0.5505	Remote Similarity	NPC174679
0.5505	Remote Similarity	NPC279554
0.5505	Remote Similarity	NPC59804
0.5495	Remote Similarity	NPC213674
0.5487	Remote Similarity	NPC40775
0.5487	Remote Similarity	NPC159309
0.5487	Remote Similarity	NPC86222
0.5484	Remote Similarity	NPC476068
0.5478	Remote Similarity	NPC486563
0.5476	Remote Similarity	NPC65105
0.5447	Remote Similarity	NPC488560
0.5424	Remote Similarity	NPC207738
0.5417	Remote Similarity	NPC313110
0.541	Remote Similarity	NPC219180
0.541	Remote Similarity	NPC251263
0.5391	Remote Similarity	NPC123796
0.5385	Remote Similarity	NPC486564
0.5379	Remote Similarity	NPC480422
0.5372	Remote Similarity	NPC123522
0.5364	Remote Similarity	NPC25605
0.5364	Remote Similarity	NPC108748
0.5349	Remote Similarity	NPC70809
0.5347	Remote Similarity	NPC167383
0.5345	Remote Similarity	NPC64715
0.5339	Remote Similarity	NPC241909
0.5327	Remote Similarity	NPC161434
0.5321	Remote Similarity	NPC179434
0.5315	Remote Similarity	NPC473373
0.5308	Remote Similarity	NPC224381
0.53	Remote Similarity	NPC191763
0.5299	Remote Similarity	NPC281148
0.5299	Remote Similarity	NPC276093
0.5285	Remote Similarity	NPC155410
0.528	Remote Similarity	NPC488211
0.5278	Remote Similarity	NPC269095
0.5276	Remote Similarity	NPC470876
0.5271	Remote Similarity	NPC302543
0.527	Remote Similarity	NPC469778
0.5268	Remote Similarity	NPC470512
0.5254	Remote Similarity	NPC218954
0.5243	Remote Similarity	NPC237503
0.5205	Remote Similarity	NPC469776
0.5203	Remote Similarity	NPC32723
0.5203	Remote Similarity	NPC475899
0.5203	Remote Similarity	NPC470911
0.5179	Remote Similarity	NPC603546
0.5168	Remote Similarity	NPC481323
0.5166	Remote Similarity	NPC481324
0.5164	Remote Similarity	NPC473824
0.5159	Remote Similarity	NPC85154
0.513	Remote Similarity	NPC117714
0.513	Remote Similarity	NPC295941
0.5118	Remote Similarity	NPC484061
0.5118	Remote Similarity	NPC484062
0.5099	Remote Similarity	NPC135334
0.5094	Remote Similarity	NPC110139
0.5094	Remote Similarity	NPC108709
0.5093	Remote Similarity	NPC209894
0.5091	Remote Similarity	NPC164194
0.5091	Remote Similarity	NPC29069
0.5089	Remote Similarity	NPC139894
0.5086	Remote Similarity	NPC488526
0.5086	Remote Similarity	NPC101744
0.5083	Remote Similarity	NPC470477
0.5082	Remote Similarity	NPC475119
0.5082	Remote Similarity	NPC185466
0.5082	Remote Similarity	NPC288205
0.5082	Remote Similarity	NPC51465
0.5081	Remote Similarity	NPC471384
0.5078	Remote Similarity	NPC265841
0.5078	Remote Similarity	NPC473452
0.5045	Remote Similarity	NPC235841
0.5045	Remote Similarity	NPC297208
0.5044	Remote Similarity	NPC150400
0.5043	Remote Similarity	NPC139044
0.5043	Remote Similarity	NPC162574
0.5042	Remote Similarity	NPC78034
0.5041	Remote Similarity	NPC610204
0.504	Remote Similarity	NPC166422
0.5035	Remote Similarity	NPC220838

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC160415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7433
0.1-0.2	1657
0.2-0.3	54
0.3-0.4	6
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