NPASS Compound

Natural Product: NPC11242

Natural Product ID	NPC11242
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside K
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	gordonoside K
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782844
PubChem CID	54587128
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 -7.0048 -2.1753 -3.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5196 -1.8580 -2.8700 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7820 -2.9435 -3.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2412 -0.5731 -3.5477 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4668 0.6393 -2.7315 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4704 0.4749 -1.2619 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8516 -0.7383 -0.6836 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1482 -1.9640 -1.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4150 -0.5859 -0.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9323 -1.5024 0.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5442 -1.5671 1.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6972 -0.6127 0.2841 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7518 -0.6162 0.6974 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0087 -0.6571 2.1576 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3080 -1.9316 0.1271 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7612 -2.0934 0.2746 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6159 -0.8748 0.0574 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9391 0.4127 -0.1143 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4866 1.3971 0.9103 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3673 1.0114 -1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4500 0.4626 -0.0452 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8722 1.7764 0.3871 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5239 1.8573 -0.2082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3837 0.7007 0.2065 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0330 1.0985 1.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5516 0.5393 -0.7649 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0177 0.1692 -2.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3475 1.8125 -0.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7900 1.6608 -0.5563 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4442 2.8506 -0.8801 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6342 -0.8112 1.0399 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8883 -1.1469 0.5356 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8927 -0.0805 0.8189 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3044 -0.5715 0.5499 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4833 -1.8227 1.4228 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4519 -2.8089 0.8500 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6874 -4.1619 1.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8486 -4.7473 2.0819 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8758 -4.8158 1.0876 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2281 -2.3315 1.2382 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7497 -2.3397 1.3603 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2573 0.3843 0.7956 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0429 0.6802 -0.3057 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9810 2.1062 -0.7542 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2810 2.5170 -1.4579 C 0 0 2 0 0 0 0 0 0 0 0 0 12.4861 2.2347 -0.5905 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0040 1.3789 0.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3461 0.2882 0.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1260 3.3850 -0.1603 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2126 3.8845 -1.6891 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9872 2.2288 -1.7543 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6166 1.0767 0.0974 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8976 0.5432 -0.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8735 0.7536 -1.4993 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1625 0.3750 0.6004 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4304 0.4152 1.2148 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8062 -0.9159 1.8271 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2106 -0.8456 2.2989 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7487 0.4889 2.6087 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8390 1.6439 2.4548 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8403 2.5171 3.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1112 3.6695 3.4944 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5299 1.3574 2.2020 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9189 0.7368 1.8507 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3157 -1.7188 3.4079 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5737 -1.9703 0.9440 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4034 -1.6385 -3.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5732 -1.8873 -2.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1313 -3.2937 -3.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3112 -3.0845 -4.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8414 -3.8636 -3.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7455 -2.6589 -3.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8881 -0.5298 -4.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1763 -0.5938 -3.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4894 1.0434 -3.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7838 1.4469 -3.1192 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3804 -0.8657 0.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0302 -2.4813 -0.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3438 -2.7650 -1.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5897 -2.3276 0.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1606 -2.6043 0.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6367 -1.3443 2.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6910 -1.0170 -0.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2067 0.3214 2.6442 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2300 -1.1383 2.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9351 -1.2593 2.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8092 -2.8076 0.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0375 -1.9378 -0.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0410 -2.5074 1.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0561 -2.9492 -0.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1936 -1.1256 -0.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1451 0.9038 1.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6972 1.9291 1.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1430 2.1748 0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6311 1.8447 -1.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3424 0.2647 -2.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3411 1.5139 -1.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1013 0.3283 -1.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7185 1.8847 1.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4350 2.6496 0.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4237 2.0129 -1.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9472 2.8134 0.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1664 2.1982 1.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3422 0.9107 2.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0255 0.6618 1.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3330 -0.8811 -2.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5020 0.8051 -2.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9514 0.3277 -2.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3140 2.2083 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9592 2.6525 -0.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9481 1.4971 0.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2654 3.4812 -0.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8024 -1.3860 -0.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8387 0.1516 1.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3229 -0.9323 -0.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1741 -1.6244 2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5498 -2.7645 -0.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3269 -5.4287 1.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1812 -2.3171 2.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7465 0.0635 -1.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8148 2.8314 0.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3235 1.9416 -2.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2172 1.6509 -1.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2738 1.9489 1.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8190 1.0875 1.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4077 4.0272 0.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8182 4.1850 -2.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2553 1.6069 -2.4922 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2212 1.8047 0.4366 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1868 0.6202 0.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1287 -1.0817 2.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8477 -1.3444 1.5086 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1268 0.4808 3.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1980 2.3379 1.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4897 1.9365 4.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9204 2.7686 3.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1648 3.9476 2.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8656 0.2144 0.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2543 -2.0325 3.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1431 -2.7531 1.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 35 41 1 0 34 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 44 51 1 0 33 52 1 0 6 53 1 1 53 54 2 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 59 64 1 0 58 65 1 0 57 66 1 0 8 2 1 0 26 9 1 0 40 32 1 0 48 43 1 0 63 56 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 67 1 0 1 68 1 0 1 69 1 0 3 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 7 77 1 1 8 78 1 0 8 79 1 0 10 80 1 0 11 81 1 0 11 82 1 0 12 83 1 6 14 84 1 0 14 85 1 0 14 86 1 0 15 87 1 0 15 88 1 0 16 89 1 0 16 90 1 0 17 91 1 6 19 92 1 0 19 93 1 0 19 94 1 0 20 95 1 0 20 96 1 0 20 97 1 0 21 98 1 6 22 99 1 0 22100 1 0 23101 1 0 23102 1 0 25103 1 0 25104 1 0 25105 1 0 27106 1 0 27107 1 0 27108 1 0 28109 1 0 28110 1 0 29111 1 1 30112 1 0 32113 1 6 33114 1 1 34115 1 6 35116 1 1 36117 1 6 39118 1 0 41119 1 0 43120 1 6 44121 1 1 45122 1 6 46123 1 6 47124 1 0 47125 1 0 49126 1 0 50127 1 0 51128 1 0 52129 1 0 56130 1 6 57131 1 1 58132 1 6 59133 1 1 60134 1 6 61135 1 0 61136 1 0 62137 1 0 64138 1 0 65139 1 0 66140 1 0 M END

Standard InCHIKey	CGHIFJOGGKUIFS-SPTOROIVSA-N
Standard InCHI	InChI=1S/C47H74O19/c1-42(2)14-15-47(41(60)66-39-32(55)30(53)29(52)23(18-48)62-39)21(16-42)20-8-9-25-44(5)12-11-27(43(3,4)24(44)10-13-45(25,6)46(20,7)17-26(47)50)63-40-34(57)35(33(56)36(65-40)37(58)59)64-38-31(54)28(51)22(49)19-61-38/h8,21-36,38-40,48-57H,9-19H2,1-7H3,(H,58,59)/t21-,22-,23+,24-,25+,26+,27-,28-,29+,30-,31+,32+,33-,34+,35-,36-,38-,39-,40+,44-,45+,46+,47+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	942.48	Volume:	912.121 ? Van der Waals volume.
Dense:	1.033	LogP:	1.17 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.497 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	46.0
TPSA:	312.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.374	Fsp³:	0.915
MCE-18:	177.778 ? 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:	0.731	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.173	Promiscuous compounds:	0.126

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.249	MDCK Permeability:	-5.038
Pgp-inhibitor:	0.0	Pgp-substrate:	0.093
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):	0.277
20% Bioavailability (F20%):	0.31	30% Bioavailability (F30%):	0.972
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.591
Plasma Protein Binding (PPB):	65.484%	Volume Distribution (VD):	-0.494
Fu:	24.267% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.023
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.098 ? 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):

0.003

Half-life (T1/2):

3.589

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.806	Drug-induced Liver Injury (DILI):	0.984
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.127	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.839	RPMI-8226 Immunitoxicity:	0.106
A549 Cytotoxicity:	0.714	Hek293 Cytotoxicity:	0.179
BCF:	0.58 ? 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:	3.376 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.892 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.933 ? 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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.4	%	PMID[21473609]

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 NPC11242 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	20888
0.1-0.2	24394
0.2-0.3	3297
0.3-0.4	697
0.4-0.5	331
0.5-0.6	152
0.6-0.7	37
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC4749
0.844	Intermediate Similarity	NPC21691
0.7913	Intermediate Similarity	NPC302543
0.7857	Intermediate Similarity	NPC1046
0.7838	Intermediate Similarity	NPC283417
0.7838	Intermediate Similarity	NPC200049
0.7692	Intermediate Similarity	NPC159309
0.7692	Intermediate Similarity	NPC86222
0.7642	Intermediate Similarity	NPC64715
0.7407	Intermediate Similarity	NPC114484
0.6964	Remote Similarity	NPC477193
0.6903	Remote Similarity	NPC187290
0.6875	Remote Similarity	NPC301449
0.6875	Remote Similarity	NPC601290
0.6807	Remote Similarity	NPC85154
0.6754	Remote Similarity	NPC104137
0.6754	Remote Similarity	NPC26626
0.6727	Remote Similarity	NPC164389
0.6667	Remote Similarity	NPC123522
0.6667	Remote Similarity	NPC157868
0.6514	Remote Similarity	NPC6377
0.6514	Remote Similarity	NPC208381
0.6466	Remote Similarity	NPC477194
0.6435	Remote Similarity	NPC477191
0.6423	Remote Similarity	NPC286457
0.6372	Remote Similarity	NPC475591
0.6372	Remote Similarity	NPC236870
0.6356	Remote Similarity	NPC477196
0.633	Remote Similarity	NPC475516
0.6283	Remote Similarity	NPC44716
0.6283	Remote Similarity	NPC251768
0.6271	Remote Similarity	NPC477195
0.625	Remote Similarity	NPC220160
0.624	Remote Similarity	NPC475514
0.6207	Remote Similarity	NPC281148
0.6186	Remote Similarity	NPC481078
0.6161	Remote Similarity	NPC469946
0.616	Remote Similarity	NPC265841
0.614	Remote Similarity	NPC40775
0.614	Remote Similarity	NPC488526
0.6136	Remote Similarity	NPC33012
0.6111	Remote Similarity	NPC90856
0.6106	Remote Similarity	NPC192791
0.6098	Remote Similarity	NPC602995
0.6071	Remote Similarity	NPC473884
0.6061	Remote Similarity	NPC8524
0.6032	Remote Similarity	NPC13998
0.5985	Remote Similarity	NPC489209
0.5984	Remote Similarity	NPC470876
0.5983	Remote Similarity	NPC302887
0.5966	Remote Similarity	NPC160452
0.5966	Remote Similarity	NPC477192
0.5965	Remote Similarity	NPC223301
0.5965	Remote Similarity	NPC242840
0.5965	Remote Similarity	NPC171544
0.5932	Remote Similarity	NPC104372
0.5913	Remote Similarity	NPC117714
0.5913	Remote Similarity	NPC30289
0.5906	Remote Similarity	NPC473452
0.5906	Remote Similarity	NPC488308
0.5897	Remote Similarity	NPC297263
0.5887	Remote Similarity	NPC123199
0.5873	Remote Similarity	NPC481080
0.5859	Remote Similarity	NPC271610
0.5859	Remote Similarity	NPC312650
0.5856	Remote Similarity	NPC475208
0.5856	Remote Similarity	NPC48499
0.5846	Remote Similarity	NPC309223
0.5841	Remote Similarity	NPC480420
0.5839	Remote Similarity	NPC489208
0.5833	Remote Similarity	NPC128925
0.5833	Remote Similarity	NPC69811
0.5826	Remote Similarity	NPC75417
0.5818	Remote Similarity	NPC204458
0.5818	Remote Similarity	NPC214484
0.5804	Remote Similarity	NPC603870
0.5789	Remote Similarity	NPC295371
0.5789	Remote Similarity	NPC39211
0.5785	Remote Similarity	NPC31838
0.5738	Remote Similarity	NPC480936
0.5734	Remote Similarity	NPC475584
0.5734	Remote Similarity	NPC475152
0.5725	Remote Similarity	NPC33068
0.5725	Remote Similarity	NPC476991
0.5724	Remote Similarity	NPC485563
0.5714	Remote Similarity	NPC603832
0.5704	Remote Similarity	NPC475394
0.5702	Remote Similarity	NPC114441
0.5672	Remote Similarity	NPC102505
0.5672	Remote Similarity	NPC488514
0.5656	Remote Similarity	NPC207738
0.5641	Remote Similarity	NPC605226
0.5639	Remote Similarity	NPC482010
0.5639	Remote Similarity	NPC488309
0.5635	Remote Similarity	NPC257211
0.5625	Remote Similarity	NPC78046
0.562	Remote Similarity	NPC481079
0.5614	Remote Similarity	NPC235405
0.561	Remote Similarity	NPC815
0.5603	Remote Similarity	NPC263756
0.5603	Remote Similarity	NPC213674
0.56	Remote Similarity	NPC79643
0.5596	Remote Similarity	NPC242611
0.5593	Remote Similarity	NPC305267
0.5591	Remote Similarity	NPC470218
0.5573	Remote Similarity	NPC476779
0.5565	Remote Similarity	NPC173583
0.5565	Remote Similarity	NPC25998
0.5565	Remote Similarity	NPC249848
0.5565	Remote Similarity	NPC107966
0.5556	Remote Similarity	NPC284449
0.5556	Remote Similarity	NPC48249
0.5556	Remote Similarity	NPC112352
0.5547	Remote Similarity	NPC25663
0.5547	Remote Similarity	NPC488560
0.5546	Remote Similarity	NPC63159
0.5546	Remote Similarity	NPC235438
0.5541	Remote Similarity	NPC23020
0.554	Remote Similarity	NPC475368
0.5536	Remote Similarity	NPC238935
0.553	Remote Similarity	NPC481081
0.552	Remote Similarity	NPC609119
0.5508	Remote Similarity	NPC30735
0.5504	Remote Similarity	NPC478597
0.5496	Remote Similarity	NPC258617
0.5495	Remote Similarity	NPC480937
0.5484	Remote Similarity	NPC477197
0.547	Remote Similarity	NPC76497
0.547	Remote Similarity	NPC475171
0.5469	Remote Similarity	NPC475160
0.5469	Remote Similarity	NPC473714
0.5462	Remote Similarity	NPC232237
0.5455	Remote Similarity	NPC484059
0.5455	Remote Similarity	NPC484060
0.5447	Remote Similarity	NPC295823
0.5447	Remote Similarity	NPC174720
0.5447	Remote Similarity	NPC475467
0.5446	Remote Similarity	NPC161434
0.5431	Remote Similarity	NPC58448
0.542	Remote Similarity	NPC478596
0.542	Remote Similarity	NPC476774
0.542	Remote Similarity	NPC476780
0.5417	Remote Similarity	NPC105800
0.5392	Remote Similarity	NPC488520
0.5385	Remote Similarity	NPC71391
0.5368	Remote Similarity	NPC250247
0.5364	Remote Similarity	NPC31839
0.5349	Remote Similarity	NPC191827
0.5333	Remote Similarity	NPC11551
0.5333	Remote Similarity	NPC180550
0.5333	Remote Similarity	NPC35405
0.5321	Remote Similarity	NPC283849
0.5317	Remote Similarity	NPC470475
0.5299	Remote Similarity	NPC110700
0.5299	Remote Similarity	NPC476777
0.5294	Remote Similarity	NPC484063
0.5294	Remote Similarity	NPC484064
0.5294	Remote Similarity	NPC142151
0.5294	Remote Similarity	NPC267694
0.5294	Remote Similarity	NPC51564
0.5288	Remote Similarity	NPC488522
0.528	Remote Similarity	NPC475486
0.5276	Remote Similarity	NPC610204
0.5271	Remote Similarity	NPC166422
0.5271	Remote Similarity	NPC470476
0.5268	Remote Similarity	NPC256798
0.5267	Remote Similarity	NPC329828
0.5263	Remote Similarity	NPC189884
0.5263	Remote Similarity	NPC41061
0.5263	Remote Similarity	NPC227551
0.5263	Remote Similarity	NPC138334
0.5259	Remote Similarity	NPC144644
0.5259	Remote Similarity	NPC37860
0.5259	Remote Similarity	NPC170407
0.5254	Remote Similarity	NPC488561
0.5254	Remote Similarity	NPC488516
0.5246	Remote Similarity	NPC31193
0.5246	Remote Similarity	NPC222580
0.5242	Remote Similarity	NPC23275
0.5231	Remote Similarity	NPC475140
0.5227	Remote Similarity	NPC470518
0.5227	Remote Similarity	NPC476068
0.5227	Remote Similarity	NPC484061
0.5227	Remote Similarity	NPC484062
0.5221	Remote Similarity	NPC70809
0.5221	Remote Similarity	NPC209894
0.5221	Remote Similarity	NPC476775
0.5217	Remote Similarity	NPC476776
0.5214	Remote Similarity	NPC485562
0.521	Remote Similarity	NPC80843
0.521	Remote Similarity	NPC22956
0.5207	Remote Similarity	NPC46665
0.5203	Remote Similarity	NPC79718
0.52	Remote Similarity	NPC480473
0.52	Remote Similarity	NPC480474
0.5197	Remote Similarity	NPC213952
0.5197	Remote Similarity	NPC185466
0.5197	Remote Similarity	NPC288205
0.5197	Remote Similarity	NPC51465

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC11242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6487
0.1-0.2	2599
0.2-0.3	60
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5614	Remote Similarity	NPD8295	Clinical (unspecified phase)

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