NPASS Compound

Natural Product: NPC51579

Natural Product ID	NPC51579
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Clethroidoside F
IUPAC Name	n.a.
Synonyms	clethroidoside F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1928000
PubChem CID	56601861
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 171180 0 0 0 0 0 0 0 0999 V2000 -5.5786 -7.9617 1.7179 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2466 -6.9873 0.7879 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6223 -5.6023 1.2955 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2546 -4.7155 0.3088 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5024 -3.3681 0.6858 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9955 -2.6119 -0.3377 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9852 -1.7099 0.0656 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7879 -1.8972 -0.8186 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0914 -1.7453 -2.1550 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5752 -0.4641 -2.4013 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8829 -0.1851 -1.6586 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5439 -0.3269 -0.1926 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4892 0.5822 0.0425 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2789 1.1015 -1.9247 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5762 1.1544 -2.4039 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4708 1.5363 -3.7581 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6204 1.2302 -4.4675 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4916 1.8535 -5.8414 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6287 1.5707 -6.6007 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8049 1.7838 -3.7152 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3234 2.7983 -2.7166 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4276 2.1326 -1.6569 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1856 1.4669 -0.7073 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1067 1.9775 0.5625 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6080 1.0625 1.4977 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8775 1.4078 2.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1474 2.8772 3.0083 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2934 3.3744 2.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4902 2.3454 1.0438 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3307 2.7828 0.0527 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4548 3.5387 2.8857 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0136 3.6538 2.8206 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4465 3.6583 -3.4176 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4547 0.7068 -3.1096 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6448 -1.2653 -0.5139 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5623 -1.9463 -0.0891 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5002 -1.9914 -1.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3776 -0.8385 -1.3397 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8207 -0.0949 -0.0850 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4613 -0.9819 1.0496 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0717 -1.4802 1.1715 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1277 -2.7425 2.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7916 -0.5444 1.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0601 -0.5884 2.3656 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5699 -0.7033 2.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0361 0.3086 1.1294 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3297 -0.0376 -0.1205 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7881 0.7192 -1.3337 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1896 0.1476 -1.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9887 0.6327 -0.4002 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5335 0.1329 0.8980 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8092 -1.3204 1.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2891 0.9226 1.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7701 1.0458 1.6263 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9071 1.6664 0.3060 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3911 0.6833 -0.7559 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2580 -0.4221 -1.0497 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5871 0.1673 -1.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5256 -1.0387 -1.7473 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4451 0.7957 -2.9086 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1768 1.0086 -0.4926 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2365 2.1413 -0.1237 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8386 3.0956 0.7008 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1370 4.3900 0.3406 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8446 4.7345 -0.8146 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7812 5.2688 1.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4350 1.4720 -0.8666 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6143 1.0900 -0.2099 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5080 0.2959 0.7539 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9539 1.6088 -0.6401 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8032 2.7004 0.0507 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7028 2.0323 -0.3862 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4764 -0.1029 1.8229 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7713 1.6210 1.7525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2368 1.2568 -0.1659 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0054 -3.2395 0.6959 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5842 -4.1569 1.7538 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0985 -5.5679 1.5965 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3385 -6.2433 2.7950 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9613 -4.1547 1.7488 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4707 -1.9721 0.9433 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5674 -8.8373 1.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1608 -6.9898 0.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7841 -7.2287 -0.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0825 -5.3901 2.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0712 -3.1645 1.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7772 -1.7568 1.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5534 -3.0061 -0.6943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8407 0.3221 -2.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8445 -0.4475 -3.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6461 -0.9490 -1.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3360 -0.0444 0.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5566 0.9992 0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9914 0.1248 -2.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6630 0.1102 -4.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3429 2.9439 -5.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5655 1.4757 -6.3088 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5400 0.6611 -6.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4625 2.2968 -4.4252 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0912 3.4299 -2.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8851 2.9503 -1.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4590 2.8668 0.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7473 0.8473 3.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0262 1.1483 3.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4703 2.9741 4.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0118 4.3228 1.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9552 1.4191 1.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7948 2.0065 -0.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0178 4.1879 2.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2146 4.5580 3.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6697 4.5996 -3.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1117 0.3014 -3.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8824 -3.0407 -0.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1504 -2.8939 -0.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0463 -2.2527 -2.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8893 -0.1437 -2.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2756 -1.2176 -1.9236 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0634 -1.9278 0.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0794 -2.4780 3.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0953 -3.2541 1.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6615 -3.4610 1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1865 -0.2002 2.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6503 -1.0813 2.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1656 0.3286 1.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7393 0.3306 2.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8097 -1.4135 3.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6650 -1.7604 1.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0010 -0.5301 3.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6151 -1.1181 -0.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 0.5729 -2.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9568 1.7952 -1.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6015 0.6373 -2.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1756 -0.9513 -1.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8474 -1.6311 1.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5866 -1.4454 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2431 -2.0149 0.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9403 1.9483 2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2358 0.4227 2.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1620 1.7854 2.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4322 1.3463 -1.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8606 -1.0124 -1.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6092 -1.1088 -0.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8446 -1.3875 -0.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9174 -1.8477 -2.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3585 -0.8075 -2.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2475 1.8598 -2.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6617 0.2750 -3.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3983 0.6269 -3.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3318 0.3184 0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0692 2.6876 -1.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9417 5.7039 1.9592 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1953 6.1533 0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5401 4.7581 1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7169 1.1151 -0.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1486 1.2782 -1.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0329 2.6869 -0.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6824 3.4029 0.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1980 3.2988 -0.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3673 -0.3886 2.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6855 1.8441 1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1716 2.5136 1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1070 1.5530 2.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0612 1.9937 -0.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6563 1.6283 0.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5707 1.4148 -1.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4106 -3.5544 -0.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2713 -3.7143 2.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6429 -6.0235 0.7418 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6224 -7.1516 2.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3750 -4.9742 1.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3090 -1.7501 0.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 21 33 1 0 20 34 1 0 8 35 1 0 35 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 41 43 1 0 40 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 6 51 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 58 60 1 0 58 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 2 0 64 66 1 0 61 67 1 0 67 68 1 0 68 69 2 0 68 70 1 0 55 71 1 1 71 72 1 0 54 73 1 0 46 74 1 1 39 75 1 1 5 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 76 81 1 0 78 3 1 0 12 7 1 0 22 15 1 0 29 24 1 0 41 36 1 0 51 46 1 0 62 55 1 0 47 39 1 0 50 72 1 1 56 50 1 0 1 82 1 0 2 83 1 0 2 84 1 0 3 85 1 1 5 86 1 1 7 87 1 1 8 88 1 6 10 89 1 0 10 90 1 0 11 91 1 6 12 92 1 1 13 93 1 0 15 94 1 6 17 95 1 6 18 96 1 0 18 97 1 0 19 98 1 0 20 99 1 6 21100 1 1 22101 1 1 24102 1 6 26103 1 0 26104 1 0 27105 1 1 28106 1 6 29107 1 1 30108 1 0 31109 1 0 32110 1 0 33111 1 0 34112 1 0 36113 1 1 37114 1 0 37115 1 0 38116 1 0 38117 1 0 40118 1 6 42119 1 0 42120 1 0 42121 1 0 43122 1 0 43123 1 0 43124 1 0 44125 1 0 44126 1 0 45127 1 0 45128 1 0 47129 1 6 48130 1 0 48131 1 0 49132 1 0 49133 1 0 52134 1 0 52135 1 0 52136 1 0 53137 1 0 53138 1 0 54139 1 1 56140 1 6 57141 1 0 57142 1 0 59143 1 0 59144 1 0 59145 1 0 60146 1 0 60147 1 0 60148 1 0 61149 1 1 62150 1 6 66151 1 0 66152 1 0 66153 1 0 70154 1 0 70155 1 0 70156 1 0 71157 1 0 71158 1 0 73159 1 0 74160 1 0 74161 1 0 74162 1 0 75163 1 0 75164 1 0 75165 1 0 76166 1 6 77167 1 1 78168 1 6 79169 1 0 80170 1 0 81171 1 0 M END

Standard InCHIKey	HHORBZPRWXKSQO-LKWZKNPLSA-N
Standard InCHI	InChI=1S/C56H90O25/c1-23(59)74-44-45(75-24(2)60)55-22-73-56(31(55)16-50(44,3)4)15-11-30-52(7)13-12-33(51(5,6)29(52)10-14-53(30,8)54(56,9)17-32(55)62)79-48-42(81-47-41(70)38(67)35(64)26(18-57)76-47)37(66)28(21-72-48)78-49-43(39(68)36(65)27(19-58)77-49)80-46-40(69)34(63)25(61)20-71-46/h25-49,57-58,61-70H,10-22H2,1-9H3/t25-,26-,27-,28+,29+,30-,31-,32-,33+,34+,35-,36-,37+,38+,39+,40-,41-,42-,43-,44+,45+,46+,47+,48+,49+,52+,53-,54+,55+,56+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4CC(C)(C)[C@H]([C@@H]2OC(=O)C)OC(=O)C)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1162.58	Volume:	1106.05 ? Van der Waals volume.
Dense:	1.051	LogP:	0.41 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.299 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.017 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	55.0
TPSA:	378.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	12.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.074	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.729	Fsp³:	0.964
MCE-18:	294.982 ? 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:	0.916	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.27	Promiscuous compounds:	0.141

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.267	MDCK Permeability:	-5.222
Pgp-inhibitor:	0.0	Pgp-substrate:	0.186
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):	0.453
20% Bioavailability (F20%):	0.405	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.013
Plasma Protein Binding (PPB):	54.62%	Volume Distribution (VD):	-0.56
Fu:	31.29% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.587
HLM stability:	0.052 ? 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):

-0.202

Half-life (T1/2):

3.146

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.927
AMES Toxicity:	0.981	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.636	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.068	RPMI-8226 Immunitoxicity:	0.234
A549 Cytotoxicity:	0.84	Hek293 Cytotoxicity:	0.317
BCF:	0.344 ? 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:	3.412 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.417 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.19 ? 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
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1248/cpb.36.2220]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO25189	Stephania epigaea	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23621840]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24547899]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12290	Euphydryas cynthia	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24398	Diospyros japonica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25125	Libocedrus plumosa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25062	Genista cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24398	Diospyros japonica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25125	Libocedrus plumosa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25156	Ruellia rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25189	Stephania epigaea	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12290	Euphydryas cynthia	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24618	Sophora moorcroftiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23640	Gynoxys nitida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18670	Adiantum malesianum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25062	Genista cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3692	Dolichopentas longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24747	Targionia hypophylla	Species	Targioniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24806	Alectra parasitica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5612	Synoicum pulmonaria	Species	Polyclinidae	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	5

Activity Type	# Activity
Cell line	5

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
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2040.0	nM	PMID[21928797]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	1260.0	nM	PMID[21928797]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	1950.0	nM	PMID[21928797]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2280.0	nM	PMID[21928797]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	2190.0	nM	PMID[21928797]

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 NPC51579 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	25977
0.1-0.2	20505
0.2-0.3	2448
0.3-0.4	678
0.4-0.5	192
0.5-0.6	14
0.6-0.7	24
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8558	High Similarity	NPC471375
0.8173	Intermediate Similarity	NPC77717
0.8113	Intermediate Similarity	NPC138219
0.8113	Intermediate Similarity	NPC475234
0.787	Intermediate Similarity	NPC471374
0.7706	Intermediate Similarity	NPC473688
0.7455	Intermediate Similarity	NPC475630
0.7407	Intermediate Similarity	NPC253611
0.7407	Intermediate Similarity	NPC488782
0.7297	Intermediate Similarity	NPC273189
0.7273	Intermediate Similarity	NPC471373
0.7273	Intermediate Similarity	NPC40716
0.7217	Intermediate Similarity	NPC262567
0.7182	Intermediate Similarity	NPC267238
0.7168	Intermediate Similarity	NPC209798
0.7143	Intermediate Similarity	NPC18724
0.713	Intermediate Similarity	NPC205129
0.7009	Intermediate Similarity	NPC471425
0.7009	Intermediate Similarity	NPC158051
0.7	Intermediate Similarity	NPC471427
0.6975	Remote Similarity	NPC231566
0.6964	Remote Similarity	NPC148593
0.6949	Remote Similarity	NPC189575
0.6916	Remote Similarity	NPC224003
0.6891	Remote Similarity	NPC471429
0.6881	Remote Similarity	NPC323231
0.6847	Remote Similarity	NPC119628
0.6777	Remote Similarity	NPC106701
0.6752	Remote Similarity	NPC126753
0.6726	Remote Similarity	NPC207693
0.6721	Remote Similarity	NPC471426
0.6667	Remote Similarity	NPC157571
0.6613	Remote Similarity	NPC471431
0.6609	Remote Similarity	NPC184805
0.6372	Remote Similarity	NPC171741
0.6348	Remote Similarity	NPC158367
0.624	Remote Similarity	NPC22709
0.6218	Remote Similarity	NPC606553
0.619	Remote Similarity	NPC471424
0.619	Remote Similarity	NPC471430
0.6154	Remote Similarity	NPC470623
0.6124	Remote Similarity	NPC471428
0.6098	Remote Similarity	NPC470622
0.6094	Remote Similarity	NPC471626
0.5968	Remote Similarity	NPC603137
0.5868	Remote Similarity	NPC609281
0.5854	Remote Similarity	NPC607904
0.5854	Remote Similarity	NPC610204
0.5854	Remote Similarity	NPC610461
0.584	Remote Similarity	NPC609305
0.5702	Remote Similarity	NPC606145
0.5583	Remote Similarity	NPC267637
0.5574	Remote Similarity	NPC87393
0.552	Remote Similarity	NPC185466
0.5238	Remote Similarity	NPC207738
0.5191	Remote Similarity	NPC66513
0.5081	Remote Similarity	NPC123796
0.5076	Remote Similarity	NPC475140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7688
0.1-0.2	1422
0.2-0.3	38
0.3-0.4	2
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