NPASS Compound

Natural Product: NPC119592

Natural Product ID	NPC119592
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Huzhangoside D
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Huzhangoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1171451
PubChem CID	49799270
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 198208 0 0 0 0 0 0 0 0999 V2000 -16.9792 -3.2625 -1.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.6114 -2.1460 -2.0525 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.6732 -1.0658 -2.1804 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.8197 -0.3037 -0.9090 C 0 0 2 0 0 0 0 0 0 0 0 0 -16.6582 -0.4212 0.0035 C 0 0 2 0 0 0 0 0 0 0 0 0 -15.3648 -0.8957 -0.5633 C 0 0 1 0 0 0 0 0 0 0 0 0 -15.4292 -1.5136 -1.8009 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.3873 0.0657 -0.5009 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2441 -0.1677 0.1982 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.9526 0.7688 1.3409 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.0198 0.7547 2.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5162 1.5578 3.4534 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8133 0.2421 2.0114 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6803 0.3048 1.2278 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8887 -0.7787 0.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0122 -0.2180 -0.6929 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.1790 -1.0790 -1.7702 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7239 -0.9333 -0.5932 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5525 0.1302 1.9762 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7799 1.2828 1.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4929 1.2557 2.6049 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7664 2.5895 2.3846 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5937 2.6622 3.3306 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1679 1.2876 3.7154 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3896 0.3114 2.6012 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7152 0.2068 2.1802 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6109 0.7028 1.4839 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6476 -0.1343 0.9491 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4657 -1.2468 1.4688 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8808 0.3743 -0.2464 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0045 0.6875 -1.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8243 -0.5633 -1.4345 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0002 -1.6510 -2.0356 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5051 -1.9187 -3.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0432 -2.9458 -1.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5537 -1.1922 -2.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.6841 -0.8348 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5965 -0.3552 -1.0242 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2444 -1.1655 -1.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -0.9541 -1.9013 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2365 0.1215 -1.0663 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7054 -0.0062 -0.7165 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0285 -1.1896 0.1266 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4515 -0.1461 -2.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4048 0.9680 -2.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3570 1.0851 -1.1241 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5699 1.5312 0.0548 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1447 1.0030 1.3258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7427 3.0605 0.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2711 3.6671 -1.0405 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0903 1.3103 -0.0821 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3561 1.5339 1.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8803 1.6583 0.8699 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3714 0.4667 0.0894 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1559 -0.6557 1.0413 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0181 0.9028 -0.5070 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2170 1.8215 -1.6975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8075 1.6200 0.4942 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2445 1.6580 0.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0722 -0.0727 -0.9912 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4139 0.0989 -1.3147 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2944 -0.3191 -0.1675 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5715 -1.8045 -0.2001 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5855 -2.6045 -0.9851 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3484 -1.9617 -2.3150 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8155 -0.6573 -2.4166 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4448 -2.8344 -0.2392 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7447 -2.3139 1.1003 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5357 0.2991 -0.3120 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8732 1.1337 0.7542 C 0 0 1 0 0 0 0 0 0 0 0 0 12.1131 0.5229 1.3712 C 0 0 1 0 0 0 0 0 0 0 0 0 13.1081 0.3595 0.2392 C 0 0 1 0 0 0 0 0 0 0 0 0 13.2774 1.6662 -0.4345 C 0 0 2 0 0 0 0 0 0 0 0 0 12.3128 2.7410 -0.1119 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8746 3.7559 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0539 2.3877 0.2729 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3707 1.4370 -1.8278 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2711 -0.2450 0.6382 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4017 -1.4855 0.0183 C 0 0 1 0 0 0 0 0 0 0 0 0 15.6479 -1.5591 -0.8335 C 0 0 1 0 0 0 0 0 0 0 0 0 16.8222 -2.1803 -0.1079 C 0 0 1 0 0 0 0 0 0 0 0 0 16.6805 -1.9427 1.3591 C 0 0 1 0 0 0 0 0 0 0 0 0 15.3582 -2.3733 1.9179 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3809 -2.5230 0.9607 O 0 0 0 0 0 0 0 0 0 0 0 0 17.6638 -2.7146 2.0147 O 0 0 0 0 0 0 0 0 0 0 0 0 16.9599 -3.5086 -0.4586 O 0 0 0 0 0 0 0 0 0 0 0 0 15.3602 -2.3384 -1.9512 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5949 1.1745 2.4679 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7672 0.8597 4.9085 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5633 3.3053 2.6378 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6046 3.6654 2.6605 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.0417 -1.2677 1.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.0342 -0.6046 -0.2574 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.1481 -0.1756 -3.1527 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.9747 -3.1785 -0.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1478 -3.3776 -0.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.9906 -4.2147 -1.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5222 -2.5651 -3.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -18.6086 -1.4384 -2.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.9474 0.7857 -1.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5477 0.5808 0.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9972 -1.7339 0.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3221 -1.1827 0.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6646 1.7828 1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0802 -0.2837 2.7988 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9698 1.1894 2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5376 1.6334 3.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7152 1.2970 0.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1852 -1.7126 0.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6804 0.8016 -0.9810 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9015 -2.0093 -1.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9530 -1.0179 0.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6012 1.3879 0.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3855 2.1997 2.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7416 1.1234 3.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4125 2.6524 1.3287 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8597 3.2847 4.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0539 1.3405 3.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0385 -0.7177 2.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6393 1.1494 -2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6513 1.4362 -0.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6910 -0.2926 -2.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2414 -0.8416 -0.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5084 -0.9667 -4.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9364 -2.7278 -3.9409 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5718 -2.2259 -3.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7365 -2.9327 -0.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3674 -3.7927 -1.9236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0075 -3.2274 -0.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5494 -0.3639 -2.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9952 -2.0679 -2.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0962 -1.5977 -0.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1625 -2.1142 -2.0162 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1892 -1.9348 -1.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7421 -0.7358 -3.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2307 1.0504 -1.7257 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2999 -2.0148 0.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9833 -1.6786 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.9698 1.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0356 -1.1024 -2.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7675 -0.2135 -2.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9227 1.9236 -2.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0124 0.6784 -3.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1006 1.8760 -1.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1023 1.5754 1.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5182 1.2262 2.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4540 -0.0622 1.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2422 3.5133 0.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8219 3.3215 0.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2191 4.6222 -0.8894 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7223 2.0982 -0.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6404 2.4840 1.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.7566 1.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6853 2.6264 0.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3358 1.6687 1.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9705 -0.6076 1.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0162 -1.6492 0.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2276 -0.4857 1.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9491 2.6193 -1.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7562 2.3451 -1.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4202 1.2572 -2.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4527 2.6953 0.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7019 1.3038 1.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7781 2.1200 1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4317 2.4177 -0.6973 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6218 1.1682 -1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7910 -0.0222 0.7742 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5730 -1.9771 -0.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0664 -3.5929 -1.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2346 -1.9182 -2.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7667 -2.5536 -3.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7388 -3.2917 -0.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6296 -3.3033 1.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0269 1.1110 1.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8227 -0.5043 1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5917 -0.3329 -0.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3024 2.0479 -0.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1771 3.3387 -1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8072 3.3774 1.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2083 4.7016 0.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1109 4.0784 1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1250 1.8999 -2.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5354 -1.6983 -0.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8652 -0.5366 -1.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 17.7239 -1.5938 -0.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9136 -0.8806 1.5874 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0043 -1.5816 2.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4249 -3.3141 2.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 17.3493 -2.8739 2.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6724 -4.0591 0.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0491 -3.2508 -1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2440 0.7639 3.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0604 1.7191 5.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9272 4.1021 2.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0781 3.4775 3.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.6697 -0.7690 1.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 -19.7392 -0.3895 -0.9409 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1908 -0.0478 -2.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 14 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 25 27 1 0 27 28 1 0 28 29 2 0 30 28 1 1 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 33 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 1 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 1 47 49 1 0 49 50 1 0 47 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 1 54 56 1 0 56 57 1 6 56 58 1 0 58 59 1 0 46 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 62 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 74 76 1 0 73 77 1 0 72 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 82 85 1 0 81 86 1 0 80 87 1 0 71 88 1 0 24 89 1 0 23 90 1 0 22 91 1 0 5 92 1 0 4 93 1 0 3 94 1 0 7 2 1 0 16 9 1 0 26 21 1 0 59 30 1 0 66 61 1 0 76 70 1 0 84 79 1 0 37 30 1 0 56 38 1 0 54 41 1 0 51 42 1 0 1 95 1 0 1 96 1 0 1 97 1 0 2 98 1 6 3 99 1 6 4100 1 6 5101 1 1 6102 1 1 9103 1 1 10104 1 6 11105 1 0 11106 1 0 12107 1 0 14108 1 6 15109 1 1 16110 1 6 17111 1 0 18112 1 0 20113 1 0 20114 1 0 21115 1 1 22116 1 6 23117 1 1 24118 1 1 25119 1 1 31120 1 0 31121 1 0 32122 1 0 32123 1 0 34124 1 0 34125 1 0 34126 1 0 35127 1 0 35128 1 0 35129 1 0 36130 1 0 36131 1 0 37132 1 1 39133 1 0 40134 1 0 40135 1 0 41136 1 6 43137 1 0 43138 1 0 43139 1 0 44140 1 0 44141 1 0 45142 1 0 45143 1 0 46144 1 6 48145 1 0 48146 1 0 48147 1 0 49148 1 0 49149 1 0 50150 1 0 51151 1 6 52152 1 0 52153 1 0 53154 1 0 53155 1 0 55156 1 0 55157 1 0 55158 1 0 57159 1 0 57160 1 0 57161 1 0 58162 1 0 58163 1 0 59164 1 0 59165 1 0 61166 1 6 62167 1 1 63168 1 6 64169 1 6 65170 1 0 65171 1 0 67172 1 0 68173 1 0 70174 1 1 71175 1 1 72176 1 6 73177 1 1 74178 1 6 75179 1 0 75180 1 0 75181 1 0 77182 1 0 79183 1 6 80184 1 6 81185 1 6 82186 1 6 83187 1 0 83188 1 0 85189 1 0 86190 1 0 87191 1 0 88192 1 0 89193 1 0 90194 1 0 91195 1 0 92196 1 0 93197 1 0 94198 1 0 M END

Standard InCHIKey	PLQZZVHULIUSEV-FXDKWXKUSA-N
Standard InCHI	InChI=1S/C64H104O30/c1-25-36(69)41(74)45(78)54(86-25)91-49-31(20-65)88-52(47(80)43(49)76)85-23-32-40(73)42(75)46(79)55(89-32)94-58(82)64-17-15-59(3,4)19-28(64)27-9-10-34-60(5)13-12-35(61(6,24-66)33(60)11-14-63(34,8)62(27,7)16-18-64)90-57-51(39(72)30(68)22-84-57)93-56-48(81)50(37(70)26(2)87-56)92-53-44(77)38(71)29(67)21-83-53/h9,25-26,28-57,65-81H,10-24H2,1-8H3/t25-,26-,28-,29+,30-,31+,32+,33+,34+,35-,36-,37-,38+,39-,40+,41+,42-,43+,44+,45+,46+,47+,48+,49+,50+,51+,52+,53-,54-,55-,56-,57-,60-,61-,62+,63+,64-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O[C@H]1[C@@H]([C@@H]([C@@H](CO1)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1352.66	Volume:	1279.812 ? Van der Waals volume.
Dense:	1.057	LogP:	0.443 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.142 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.183 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	63.0
TPSA:	471.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	30.0
H-Bond Donor:	17.0	Rings:	11.0
Heavy Atoms:	30.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.694	Fsp³:	0.953
MCE-18:	238.0 ? 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:	0.724	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.35	Promiscuous compounds:	0.063

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.073	MDCK Permeability:	-4.912
Pgp-inhibitor:	0.0	Pgp-substrate:	0.981
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):	0.998
20% Bioavailability (F20%):	0.972	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	53.927%	Volume Distribution (VD):	-0.243
Fu:	20.317% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.001
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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.513
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-1.254

Half-life (T1/2):

4.777

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.522	Drug-induced Liver Injury (DILI):	0.926
AMES Toxicity:	0.956	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.679	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.038	RPMI-8226 Immunitoxicity:	0.515
A549 Cytotoxicity:	0.863	Hek293 Cytotoxicity:	0.203
BCF:	1.311 ? 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:	3.62 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.269 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.264 ? 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
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[15387651]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots and rhizomes	Shaoguan, Guangdong Province, China	2007-Dec	PMID[20540535]
NPO14101	Artemisia herba-alba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33588649]
NPO23649	Protoreaster nodosus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23939	Onychium siliculosum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8552	Clematis tibetana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16842	Gentianodes tianschanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14101	Artemisia herba-alba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8552	Clematis tibetana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23939	Onychium siliculosum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8552	Clematis tibetana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16842	Gentianodes tianschanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2463	Anemone rivularis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23939	Onychium siliculosum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27008	Trixis pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8552	Clematis tibetana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2463	Anemone rivularis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14101	Artemisia herba-alba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23649	Protoreaster nodosus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16842	Gentianodes tianschanica	Species	Gentianaceae	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	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	>	50000.0	nM	PMID[20540535]
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	IC50	>	50000.0	nM	PMID[20540535]

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 NPC119592 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	25224
0.1-0.2	21057
0.2-0.3	2389
0.3-0.4	671
0.4-0.5	287
0.5-0.6	110
0.6-0.7	34
0.7-0.8	0
0.8-0.85	9
0.85-0.9	10
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202828
0.9381	High Similarity	NPC298034
0.9381	High Similarity	NPC71065
0.9292	High Similarity	NPC236638
0.9292	High Similarity	NPC294453
0.8991	High Similarity	NPC76972
0.8991	High Similarity	NPC469782
0.8991	High Similarity	NPC204414
0.8793	High Similarity	NPC305981
0.8718	High Similarity	NPC261506
0.8718	High Similarity	NPC4328
0.8707	High Similarity	NPC65105
0.8621	High Similarity	NPC41061
0.8621	High Similarity	NPC227551
0.85	High Similarity	NPC250247
0.8455	Intermediate Similarity	NPC241909
0.8319	Intermediate Similarity	NPC60557
0.8319	Intermediate Similarity	NPC67857
0.8235	Intermediate Similarity	NPC293330
0.8103	Intermediate Similarity	NPC135904
0.8103	Intermediate Similarity	NPC123199
0.8083	Intermediate Similarity	NPC43550
0.8067	Intermediate Similarity	NPC110633
0.8051	Intermediate Similarity	NPC481080
0.7949	Intermediate Similarity	NPC155410
0.7931	Intermediate Similarity	NPC79643
0.7815	Intermediate Similarity	NPC488560
0.7807	Intermediate Similarity	NPC295823
0.7807	Intermediate Similarity	NPC174720
0.7807	Intermediate Similarity	NPC475467
0.7731	Intermediate Similarity	NPC100639
0.7681	Intermediate Similarity	NPC469775
0.768	Intermediate Similarity	NPC220160
0.7627	Intermediate Similarity	NPC192600
0.7586	Intermediate Similarity	NPC481078
0.7581	Intermediate Similarity	NPC481081
0.7542	Intermediate Similarity	NPC475287
0.7518	Intermediate Similarity	NPC469774
0.7456	Intermediate Similarity	NPC475504
0.744	Intermediate Similarity	NPC136768
0.7361	Intermediate Similarity	NPC100925
0.7295	Intermediate Similarity	NPC475160
0.7295	Intermediate Similarity	NPC473714
0.7273	Intermediate Similarity	NPC165204
0.726	Intermediate Similarity	NPC469777
0.7258	Intermediate Similarity	NPC476068
0.7183	Intermediate Similarity	NPC469776
0.713	Intermediate Similarity	NPC102439
0.7114	Intermediate Similarity	NPC469772
0.708	Intermediate Similarity	NPC295371
0.7069	Intermediate Similarity	NPC63159
0.7043	Intermediate Similarity	NPC104071
0.7034	Intermediate Similarity	NPC32723
0.702	Intermediate Similarity	NPC469773
0.7	Intermediate Similarity	NPC224381
0.6986	Remote Similarity	NPC481323
0.6986	Remote Similarity	NPC469778
0.6892	Remote Similarity	NPC135334
0.6875	Remote Similarity	NPC258617
0.685	Remote Similarity	NPC57484
0.6846	Remote Similarity	NPC481324
0.6822	Remote Similarity	NPC161717
0.681	Remote Similarity	NPC112352
0.6667	Remote Similarity	NPC70809
0.6667	Remote Similarity	NPC295941
0.6565	Remote Similarity	NPC471385
0.6557	Remote Similarity	NPC481079
0.6544	Remote Similarity	NPC480422
0.6457	Remote Similarity	NPC133818
0.6357	Remote Similarity	NPC471550
0.6288	Remote Similarity	NPC473452
0.6241	Remote Similarity	NPC475514
0.6167	Remote Similarity	NPC469946
0.6154	Remote Similarity	NPC48499
0.6107	Remote Similarity	NPC191827
0.6098	Remote Similarity	NPC148417
0.6066	Remote Similarity	NPC309714
0.6045	Remote Similarity	NPC480418
0.6043	Remote Similarity	NPC102505
0.6043	Remote Similarity	NPC488514
0.6031	Remote Similarity	NPC475209
0.6031	Remote Similarity	NPC251263
0.6031	Remote Similarity	NPC480419
0.6027	Remote Similarity	NPC472268
0.6016	Remote Similarity	NPC101744
0.6016	Remote Similarity	NPC473459
0.6016	Remote Similarity	NPC46665
0.6	Remote Similarity	NPC473373
0.6	Remote Similarity	NPC150400
0.5959	Remote Similarity	NPC297950
0.5954	Remote Similarity	NPC323341
0.5932	Remote Similarity	NPC29069
0.5929	Remote Similarity	NPC480417
0.5926	Remote Similarity	NPC13998
0.592	Remote Similarity	NPC297263
0.5909	Remote Similarity	NPC219180
0.587	Remote Similarity	NPC309223
0.5865	Remote Similarity	NPC470218
0.5833	Remote Similarity	NPC475899
0.5827	Remote Similarity	NPC276093
0.5814	Remote Similarity	NPC31838
0.5814	Remote Similarity	NPC187290
0.5809	Remote Similarity	NPC286457
0.5804	Remote Similarity	NPC477464
0.5793	Remote Similarity	NPC475368
0.5781	Remote Similarity	NPC301449
0.5781	Remote Similarity	NPC601290
0.5748	Remote Similarity	NPC134835
0.5742	Remote Similarity	NPC472269
0.5704	Remote Similarity	NPC54636
0.568	Remote Similarity	NPC160415
0.5656	Remote Similarity	NPC475516
0.5643	Remote Similarity	NPC302543
0.5635	Remote Similarity	NPC480475
0.56	Remote Similarity	NPC223301
0.56	Remote Similarity	NPC171544
0.5593	Remote Similarity	NPC256798
0.5581	Remote Similarity	NPC73318
0.5581	Remote Similarity	NPC104372
0.5556	Remote Similarity	NPC166422
0.5547	Remote Similarity	NPC481082
0.5547	Remote Similarity	NPC85154
0.5547	Remote Similarity	NPC164419
0.554	Remote Similarity	NPC470876
0.5522	Remote Similarity	NPC123522
0.552	Remote Similarity	NPC473343
0.552	Remote Similarity	NPC473734
0.5517	Remote Similarity	NPC8524
0.5512	Remote Similarity	NPC488526
0.5504	Remote Similarity	NPC486563
0.5496	Remote Similarity	NPC187618
0.5479	Remote Similarity	NPC33012
0.5462	Remote Similarity	NPC114484
0.5455	Remote Similarity	NPC90856
0.5455	Remote Similarity	NPC104137
0.5455	Remote Similarity	NPC26626
0.5455	Remote Similarity	NPC473826
0.5442	Remote Similarity	NPC480421
0.5436	Remote Similarity	NPC489208
0.5426	Remote Similarity	NPC222580
0.5426	Remote Similarity	NPC609763
0.542	Remote Similarity	NPC486564
0.542	Remote Similarity	NPC324875
0.542	Remote Similarity	NPC218954
0.542	Remote Similarity	NPC292677
0.5414	Remote Similarity	NPC75287
0.5403	Remote Similarity	NPC174679
0.5403	Remote Similarity	NPC235405
0.5403	Remote Similarity	NPC139894
0.5403	Remote Similarity	NPC279554
0.5397	Remote Similarity	NPC263756
0.5397	Remote Similarity	NPC213674
0.5396	Remote Similarity	NPC21691
0.5391	Remote Similarity	NPC10607
0.5391	Remote Similarity	NPC251768
0.5391	Remote Similarity	NPC164389
0.5385	Remote Similarity	NPC601659
0.5379	Remote Similarity	NPC80986
0.5368	Remote Similarity	NPC471384
0.536	Remote Similarity	NPC249848
0.536	Remote Similarity	NPC107966
0.5349	Remote Similarity	NPC475591
0.5349	Remote Similarity	NPC236870
0.5349	Remote Similarity	NPC235438
0.5333	Remote Similarity	NPC313110
0.5328	Remote Similarity	NPC189884
0.5328	Remote Similarity	NPC138334
0.5324	Remote Similarity	NPC4749
0.5312	Remote Similarity	NPC30735
0.5299	Remote Similarity	NPC815
0.529	Remote Similarity	NPC283417
0.529	Remote Similarity	NPC200049
0.5286	Remote Similarity	NPC473386
0.5274	Remote Similarity	NPC68767
0.5263	Remote Similarity	NPC480474
0.5253	Remote Similarity	NPC485563
0.5238	Remote Similarity	NPC173583
0.5238	Remote Similarity	NPC489209
0.5234	Remote Similarity	NPC192791
0.5231	Remote Similarity	NPC257964
0.5226	Remote Similarity	NPC45606
0.5208	Remote Similarity	NPC144644
0.5208	Remote Similarity	NPC170407
0.5197	Remote Similarity	NPC473884
0.5194	Remote Similarity	NPC230948
0.5194	Remote Similarity	NPC109588
0.5191	Remote Similarity	NPC488517
0.5185	Remote Similarity	NPC472270
0.5185	Remote Similarity	NPC112492
0.518	Remote Similarity	NPC480423
0.5169	Remote Similarity	NPC237503
0.5156	Remote Similarity	NPC161674
0.5154	Remote Similarity	NPC159309
0.5154	Remote Similarity	NPC86222
0.5149	Remote Similarity	NPC96641
0.5149	Remote Similarity	NPC480473
0.5149	Remote Similarity	NPC163183
0.5149	Remote Similarity	NPC69811
0.5143	Remote Similarity	NPC471577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC119592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7839
0.1-0.2	1258
0.2-0.3	48
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