NPASS Compound

Natural Product: NPC477078

Natural Product ID	NPC477078
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,12aS,14aR,14bR)-10-acetyloxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(3-methylbut-2-enoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,12aS,14aR,14bR)-10-acetyloxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(3-methylbut-2-enoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583930
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 143149 0 0 0 0 0 0 0 0999 V2000 9.4541 2.2358 2.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0555 1.6552 1.4765 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1723 2.7277 0.4320 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1298 2.6711 -0.6357 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9313 1.9375 -0.1278 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2383 0.5886 0.4801 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4747 0.4884 1.0607 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0326 -0.4415 -0.4192 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9775 -1.3002 -0.0595 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6734 -2.6084 0.3214 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6965 -3.7175 0.0190 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5456 -3.7106 -1.5070 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4668 -2.4653 -2.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0075 -1.4611 -1.1901 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7448 -1.7093 -0.7290 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8084 -0.7074 -1.0499 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9548 -1.1089 -2.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4927 -0.9777 -2.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9881 -1.2875 -0.6559 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6587 -0.2338 0.1678 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1561 -0.2333 0.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5111 1.2695 0.3779 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7161 -0.8744 1.4432 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0368 -0.0958 1.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4046 0.3870 1.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2147 -0.7359 0.5465 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4725 -1.0064 -0.7148 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2361 -2.0844 -1.4555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5026 -1.4100 -1.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1413 -0.5788 -1.0520 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5934 -0.2686 0.2820 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6691 -0.9661 1.1652 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0524 -0.4300 0.8937 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4941 -0.2976 -0.5050 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4338 -0.0182 -1.5239 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2789 1.3650 -2.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4024 2.3054 -1.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2937 2.0988 -0.6336 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6582 0.6331 -0.5847 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6408 0.3787 0.3944 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9489 0.0474 0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1858 -0.0072 -1.1998 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9927 -0.2209 1.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7778 -0.1762 2.3036 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9005 -0.4639 3.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4535 0.1487 2.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5288 2.7701 -0.9251 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0098 3.7677 -0.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3713 4.0985 0.8979 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2929 4.4899 -0.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7680 3.7017 -1.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2627 2.4862 -3.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0932 -1.6752 -0.8855 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1483 -2.0112 -0.0723 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3652 0.6535 1.7239 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4512 -0.7173 2.5154 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7476 1.1626 0.7069 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1772 -1.8829 1.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3897 -2.6882 -0.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5457 -4.6863 -1.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5820 -5.8610 -1.4341 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5499 -4.4501 -2.8430 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1692 -4.9539 0.4662 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0519 -2.5825 1.6538 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2311 2.7734 0.7508 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7005 3.9376 -1.0388 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4349 2.6796 -0.2019 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1900 3.3087 2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5331 1.7033 3.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1423 2.1973 3.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1204 1.3936 1.7558 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1248 3.7474 0.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5611 2.1653 -1.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2169 1.7542 -0.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4680 0.4526 1.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5146 -0.9599 0.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5430 -2.7277 -0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7177 -3.4894 0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5449 -4.1321 -1.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0639 -0.4860 -1.7558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4782 0.1027 -1.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1698 -2.1263 -2.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2112 -0.4674 -3.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9998 -1.5770 -2.8417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1744 0.0771 -2.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3714 0.7209 -0.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8466 1.8721 -0.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5455 1.4594 0.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2970 1.5852 1.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5288 -0.2318 1.9001 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2103 -1.8441 1.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9735 -0.9426 2.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9991 -0.9535 2.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5050 0.7494 2.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2139 1.1950 0.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 0.6972 2.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5890 -0.0708 -1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7059 -2.5343 -2.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4365 -2.9339 -0.7350 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8822 -1.6695 -2.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6959 -2.0216 0.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6997 -1.2268 1.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7519 -0.5946 -2.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1413 1.4048 -3.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2934 1.8200 -1.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8437 2.4952 0.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1546 0.4541 -1.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9798 -0.4643 0.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0920 -1.5574 3.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5964 -0.1955 4.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8234 0.0937 2.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6752 -0.5844 2.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4676 0.1049 3.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1703 1.1922 2.5831 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0797 5.4077 -0.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8980 3.8118 -1.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8281 4.6610 0.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3849 4.1272 -2.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5052 4.3985 -1.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9230 3.6249 -0.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4473 1.5139 -3.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7388 3.1694 -3.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1962 3.0290 -2.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2857 -2.4322 -0.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3817 -1.6372 -1.9579 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7591 -2.6045 -0.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2813 0.3961 2.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6739 -1.5701 2.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6859 1.1342 1.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7274 1.6007 0.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0125 1.8772 0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2624 -1.4563 2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8982 -2.6980 1.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2032 -2.4172 1.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9355 -2.8410 0.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1524 -3.0841 -1.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5376 -3.3873 -0.5119 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8066 -5.1101 -3.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1568 -4.9604 0.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9716 -2.9778 1.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7072 3.4056 0.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5561 3.9804 -2.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6993 1.7299 -0.3597 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 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 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 21 23 1 0 20 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 2 0 30 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 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 3 44 45 1 0 44 46 1 0 38 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 37 51 1 0 37 52 1 0 34 53 1 6 53 54 1 0 33 55 1 0 32 56 1 0 31 57 1 1 26 58 1 1 19 59 1 1 12 60 1 0 60 61 2 0 60 62 1 0 11 63 1 0 10 64 1 0 5 65 1 0 4 66 1 0 3 67 1 0 7 2 1 0 14 9 1 0 21 16 1 0 27 19 1 0 31 26 1 0 35 30 1 0 39 34 1 0 1 68 1 0 1 69 1 0 1 70 1 0 2 71 1 1 3 72 1 1 4 73 1 6 5 74 1 6 6 75 1 1 9 76 1 1 10 77 1 6 11 78 1 1 12 79 1 6 14 80 1 6 16 81 1 6 17 82 1 0 17 83 1 0 18 84 1 0 18 85 1 0 20 86 1 6 22 87 1 0 22 88 1 0 22 89 1 0 23 90 1 0 23 91 1 0 23 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 27 97 1 6 28 98 1 0 28 99 1 0 29100 1 0 32101 1 1 33102 1 1 35103 1 6 36104 1 0 36105 1 0 38106 1 0 39107 1 6 43108 1 0 45109 1 0 45110 1 0 45111 1 0 46112 1 0 46113 1 0 46114 1 0 50115 1 0 50116 1 0 50117 1 0 51118 1 0 51119 1 0 51120 1 0 52121 1 0 52122 1 0 52123 1 0 53124 1 0 53125 1 0 54126 1 0 55127 1 0 56128 1 0 57129 1 0 57130 1 0 57131 1 0 58132 1 0 58133 1 0 58134 1 0 59135 1 0 59136 1 0 59137 1 0 62138 1 0 63139 1 0 64140 1 0 65141 1 0 66142 1 0 67143 1 0 M END

Standard InCHIKey	NPOLGGWOGACJQL-UVXZLXGCSA-N
Standard InCHI	InChI=1S/C49H76O18/c1-21(2)18-29(52)65-40-39(63-23(4)51)44(5,6)19-25-24-12-13-27-46(9)16-15-28(45(7,8)26(46)14-17-47(27,10)48(24,11)37(58)38(59)49(25,40)20-50)64-43-36(33(56)32(55)35(66-43)41(60)61)67-42-34(57)31(54)30(53)22(3)62-42/h12,18,22,25-28,30-40,42-43,50,53-59H,13-17,19-20H2,1-11H3,(H,60,61)/t22-,25+,26+,27-,28+,30-,31+,32+,33+,34+,35+,36-,37+,38-,39?,40+,42-,43-,46+,47-,48+,49+/m1/s1
SMILES	C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5([C@H]([C@H]([C@@]7([C@H]6CC(C([C@@H]7OC(=O)C=C(C)C)OC(=O)C)(C)C)CO)O)O)C)C)C)C(=O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	952.5	Volume:	941.206 ? Van der Waals volume.
Dense:	1.012	LogP:	2.764 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.973 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.145 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	42.0
TPSA:	288.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.069	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.467	Fsp³:	0.857
MCE-18:	164.879 ? 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:	0.84	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.141	Promiscuous compounds:	0.25

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.94	MDCK Permeability:	-5.198
Pgp-inhibitor:	0.0	Pgp-substrate:	0.506
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):	0.128
20% Bioavailability (F20%):	0.892	30% Bioavailability (F30%):	0.911
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.987
Plasma Protein Binding (PPB):	75.675%	Volume Distribution (VD):	-0.549
Fu:	15.386% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.729	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.17
HLM stability:	0.095 ? 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):

0.18

Half-life (T1/2):

3.501

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.011
Human Hepatotoxicity (H-HT):	0.435	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.842	Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.053	Skin Sensitization:	1.0
Carcinogencity:	0.139	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.082
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.987
Hematotoxicity:	0.907	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.977	RPMI-8226 Immunitoxicity:	0.215
A549 Cytotoxicity:	0.841	Hek293 Cytotoxicity:	0.444
BCF:	0.413 ? 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:	3.42 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.25 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.263 ? 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
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	roots	Balkesir-Edremit, Turkey	2003-AUG	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31311207]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12661	Eryngium campestre	Species	Apiaceae	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
Cell line	1
Others	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
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	40	ug/ml	PMID[16872157]
NPT2	Others	Unspecified	n.a.	IC50	=	40	ug/ml	PMID[16872157]

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 NPC477078 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	21481
0.1-0.2	23980
0.2-0.3	3383
0.3-0.4	615
0.4-0.5	288
0.5-0.6	71
0.6-0.7	22
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.899	High Similarity	NPC477077
0.87	High Similarity	NPC477075
0.8	Intermediate Similarity	NPC329923
0.8	Intermediate Similarity	NPC475281
0.781	Intermediate Similarity	NPC477076
0.7281	Intermediate Similarity	NPC46823
0.7203	Intermediate Similarity	NPC329657
0.7	Intermediate Similarity	NPC477079
0.6864	Remote Similarity	NPC178264
0.678	Remote Similarity	NPC192765
0.6726	Remote Similarity	NPC329976
0.6694	Remote Similarity	NPC484833
0.6612	Remote Similarity	NPC262796
0.6612	Remote Similarity	NPC45346
0.6555	Remote Similarity	NPC277212
0.6555	Remote Similarity	NPC30279
0.6504	Remote Similarity	NPC475377
0.6504	Remote Similarity	NPC476074
0.6356	Remote Similarity	NPC478600
0.6356	Remote Similarity	NPC478599
0.6341	Remote Similarity	NPC225791
0.6316	Remote Similarity	NPC470914
0.6311	Remote Similarity	NPC470518
0.6283	Remote Similarity	NPC470913
0.6239	Remote Similarity	NPC606553
0.6148	Remote Similarity	NPC470912
0.6148	Remote Similarity	NPC473918
0.6107	Remote Similarity	NPC150893
0.6098	Remote Similarity	NPC71391
0.6048	Remote Similarity	NPC478598
0.5968	Remote Similarity	NPC475167
0.5952	Remote Similarity	NPC312650
0.5935	Remote Similarity	NPC264566
0.592	Remote Similarity	NPC134914
0.5873	Remote Similarity	NPC488308
0.584	Remote Similarity	NPC82380
0.584	Remote Similarity	NPC244296
0.5827	Remote Similarity	NPC271610
0.5827	Remote Similarity	NPC329993
0.5725	Remote Similarity	NPC329960
0.5702	Remote Similarity	NPC477197
0.5702	Remote Similarity	NPC605294
0.5692	Remote Similarity	NPC173435
0.5692	Remote Similarity	NPC172374
0.5692	Remote Similarity	NPC478064
0.569	Remote Similarity	NPC251768
0.568	Remote Similarity	NPC602995
0.5678	Remote Similarity	NPC64715
0.5656	Remote Similarity	NPC25998
0.5614	Remote Similarity	NPC472949
0.5606	Remote Similarity	NPC295408
0.5606	Remote Similarity	NPC488309
0.5547	Remote Similarity	NPC473755
0.5547	Remote Similarity	NPC484061
0.5547	Remote Similarity	NPC484062
0.5538	Remote Similarity	NPC484059
0.5538	Remote Similarity	NPC484060
0.5528	Remote Similarity	NPC478152
0.5528	Remote Similarity	NPC478151
0.5478	Remote Similarity	NPC603026
0.5462	Remote Similarity	NPC475513
0.5462	Remote Similarity	NPC131469
0.5455	Remote Similarity	NPC218954
0.5417	Remote Similarity	NPC95437
0.541	Remote Similarity	NPC187618
0.541	Remote Similarity	NPC120116
0.5403	Remote Similarity	NPC107536
0.5403	Remote Similarity	NPC280029
0.5403	Remote Similarity	NPC9470
0.5385	Remote Similarity	NPC476780
0.5379	Remote Similarity	NPC110700
0.5373	Remote Similarity	NPC484063
0.5373	Remote Similarity	NPC484064
0.5372	Remote Similarity	NPC114692
0.5372	Remote Similarity	NPC236657
0.5366	Remote Similarity	NPC609281
0.5354	Remote Similarity	NPC478150
0.5349	Remote Similarity	NPC301639
0.5349	Remote Similarity	NPC329828
0.5349	Remote Similarity	NPC478065
0.5344	Remote Similarity	NPC258617
0.5328	Remote Similarity	NPC301449
0.5328	Remote Similarity	NPC482735
0.5328	Remote Similarity	NPC601290
0.5304	Remote Similarity	NPC309780
0.5285	Remote Similarity	NPC477193
0.5263	Remote Similarity	NPC476777
0.5238	Remote Similarity	NPC313110
0.5231	Remote Similarity	NPC478597
0.5152	Remote Similarity	NPC265841
0.5145	Remote Similarity	NPC69425
0.5124	Remote Similarity	NPC482722
0.5124	Remote Similarity	NPC471963
0.5122	Remote Similarity	NPC482740
0.5116	Remote Similarity	NPC482736
0.5116	Remote Similarity	NPC482738
0.5043	Remote Similarity	NPC25605
0.5043	Remote Similarity	NPC56713
0.5039	Remote Similarity	NPC482739
0.5038	Remote Similarity	NPC478596
0.5038	Remote Similarity	NPC47995

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6723
0.1-0.2	2376
0.2-0.3	47
0.3-0.4	3
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data