NPASS Compound

Natural Product: NPC477079

Natural Product ID	NPC477079
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,10R,12aS,14aR,14bR)-8-acetyloxy-7,10-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-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,10R,12aS,14aR,14bR)-8-acetyloxy-7,10-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-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	44583932
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 11.7995 0.8548 -1.6344 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2797 2.1070 -1.0617 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0833 2.1867 -0.5325 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5715 3.4785 0.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1904 1.0595 -0.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5427 -0.0485 -0.9231 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9052 1.0992 0.0854 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0526 0.0029 0.1425 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8569 -0.5518 1.5435 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3035 -1.9465 1.3303 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7797 -2.1977 -0.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9843 -1.0847 -0.6694 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7200 0.1912 -0.5743 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9976 1.4065 -0.1021 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5191 1.3996 -0.1955 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8183 0.1292 0.1924 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5586 -1.0734 -0.2813 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8718 -2.2006 -0.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4375 -2.3267 -0.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6587 -1.0750 0.0027 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4785 0.0511 -0.5583 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7524 1.3509 -0.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6835 1.2465 -0.9287 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3889 0.1679 -0.1910 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7480 -1.1395 -0.5208 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4424 -2.1670 0.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9012 -2.2276 0.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6384 -0.9250 0.1108 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8691 0.2551 -0.3070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2738 1.3931 0.6659 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2754 0.8038 -1.6586 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7040 -1.1296 -0.7657 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9425 -1.1863 -0.1200 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8478 -0.1639 -0.7283 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1911 -0.6079 -2.1421 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0382 -1.8390 -2.0097 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7131 -2.5822 -0.7212 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4001 -2.4953 -0.3456 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0334 -4.0029 -0.9756 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1872 -4.3148 -1.3321 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0758 -4.9771 -0.8236 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3815 -1.4410 -2.0355 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0086 -0.9805 -2.7717 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0248 0.0511 -0.0144 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1487 1.3767 0.3206 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1409 1.5307 1.8271 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3862 0.8925 2.3819 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5792 1.5512 1.7407 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4544 1.4052 0.2465 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2798 1.9704 -0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6134 2.1439 -0.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7630 0.9248 2.1289 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3867 1.0302 3.7652 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0970 2.8852 2.1358 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9022 -1.5855 -1.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8218 -0.2450 -2.0002 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6589 -0.0511 1.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9164 2.4306 0.5263 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5299 1.9238 1.0872 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1961 3.0845 1.2975 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3285 3.7480 0.2648 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7044 3.5047 2.6171 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2190 0.4410 -2.0318 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0117 1.5598 -2.0291 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5184 -2.8806 1.4945 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3168 -2.3290 2.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1337 -0.5669 2.1210 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8285 1.0185 -2.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1435 0.5270 -2.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8445 0.0383 -0.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8898 3.0207 -1.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4361 4.1374 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0776 3.1982 0.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8990 3.9919 -0.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6353 -0.8338 -0.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1300 -0.0152 2.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5977 -2.4793 -0.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1889 -3.1497 0.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9032 -1.4436 -1.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3098 2.2217 -0.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2045 1.6061 -1.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3547 -3.1019 -0.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4000 -2.8547 0.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9783 -3.0931 -0.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4897 -0.8024 1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1935 2.1730 -1.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6631 1.5845 0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5585 1.0732 -2.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1436 2.2322 -0.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1367 0.3334 0.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1421 -1.9472 1.4333 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9953 -3.1403 0.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1017 -2.8605 -0.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3164 -2.8788 0.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1234 -0.8153 1.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 1.4179 0.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7578 1.2469 1.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9307 2.3304 0.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4988 1.4585 -2.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4773 0.0211 -2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1633 1.4661 -1.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8780 -1.0275 0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3001 0.7870 -0.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6767 0.2128 -2.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8126 -2.5230 -2.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3867 -2.2315 0.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2964 -5.9589 -0.6674 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9568 -2.0249 -1.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0800 -0.7402 -3.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2694 1.9256 -0.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2690 1.0209 2.2357 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3709 -0.1812 2.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5841 2.6338 2.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5604 0.3405 -0.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6775 3.2011 -0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6224 2.0493 -1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5658 1.6596 -0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5620 0.0101 2.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9053 0.2415 4.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7434 2.9749 3.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4102 -2.5493 -2.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6828 -0.8367 -2.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9981 -1.8176 -2.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3311 0.4663 -2.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9285 -0.1482 -2.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6225 -1.3102 -2.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6018 0.3692 2.1304 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7612 0.4404 2.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7280 -1.1218 1.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1192 3.3134 0.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5216 4.2360 2.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1085 2.6501 3.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8363 3.9544 3.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6949 -0.4672 -2.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2978 0.6080 -2.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8521 2.0746 -2.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4098 -3.7691 0.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6118 -3.1818 2.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4458 -2.3658 1.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8219 -2.9446 3.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9717 -1.4159 2.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4893 -2.9050 1.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0018 -0.6261 3.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 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 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 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 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 28 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 37 39 1 0 39 40 2 0 39 41 1 0 36 42 1 0 35 43 1 0 34 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 49 51 1 0 48 52 1 0 47 53 1 0 46 54 1 0 25 55 1 6 21 56 1 6 16 57 1 1 15 58 1 0 14 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 13 63 1 6 63 64 1 0 10 65 1 0 10 66 1 0 9 67 1 0 13 8 1 0 17 12 1 0 21 16 1 0 25 20 1 0 29 24 1 0 38 33 1 0 50 45 1 0 1 68 1 0 1 69 1 0 1 70 1 0 2 71 1 0 4 72 1 0 4 73 1 0 4 74 1 0 8 75 1 6 9 76 1 1 11 77 1 0 11 78 1 0 12 79 1 6 14 80 1 6 15 81 1 6 18 82 1 0 19 83 1 0 19 84 1 0 20 85 1 1 22 86 1 0 22 87 1 0 23 88 1 0 23 89 1 0 24 90 1 1 26 91 1 0 26 92 1 0 27 93 1 0 27 94 1 0 28 95 1 1 30 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 31101 1 0 33102 1 1 34103 1 6 35104 1 6 36105 1 6 37106 1 1 41107 1 0 42108 1 0 43109 1 0 45110 1 6 46111 1 1 47112 1 1 48113 1 6 49114 1 1 51115 1 0 51116 1 0 51117 1 0 52118 1 0 53119 1 0 54120 1 0 55121 1 0 55122 1 0 55123 1 0 56124 1 0 56125 1 0 56126 1 0 57127 1 0 57128 1 0 57129 1 0 58130 1 0 62131 1 0 62132 1 0 62133 1 0 63134 1 0 63135 1 0 64136 1 0 65137 1 0 65138 1 0 65139 1 0 66140 1 0 66141 1 0 66142 1 0 67143 1 0 M END

Standard InCHIKey	DQGDOZDSFKEKHQ-KYQADXOSSA-N
Standard InCHI	InChI=1S/C49H76O18/c1-12-21(2)41(61)67-38-36(57)44(5,6)19-25-24-13-14-27-46(9)17-16-28(45(7,8)26(46)15-18-47(27,10)48(24,11)37(58)39(63-23(4)51)49(25,38)20-50)64-43-35(32(55)31(54)34(65-43)40(59)60)66-42-33(56)30(53)29(52)22(3)62-42/h12-13,22,25-39,42-43,50,52-58H,14-20H2,1-11H3,(H,59,60)/b21-12-/t22-,25+,26+,27-,28+,29-,30+,31+,32+,33+,34+,35-,36+,37+,38+,39-,42-,43-,46+,47-,48+,49-/m1/s1
SMILES	C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H]([C@@H]([C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)C)O)O)O)C)C)C)O)OC(=O)C)CO)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	952.5	Volume:	941.206 ? Van der Waals volume.
Dense:	1.012	LogP:	2.517 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.786 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.572 ? 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:	6.523	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:	0.874	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.195	Promiscuous compounds:	0.275

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.9	MDCK Permeability:	-5.275
Pgp-inhibitor:	0.0	Pgp-substrate:	0.936
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):	0.846
20% Bioavailability (F20%):	0.911	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.981
Plasma Protein Binding (PPB):	68.564%	Volume Distribution (VD):	-0.502
Fu:	19.745% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.848	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.489
HLM stability:	0.259 ? 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):

0.004

Half-life (T1/2):

3.773

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.012
Human Hepatotoxicity (H-HT):	0.358	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.39	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	0.99
Carcinogencity:	0.06	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.987
Hematotoxicity:	0.4	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.785	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.076	Hek293 Cytotoxicity:	0.077
BCF:	0.35 ? 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:	3.461 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.408 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.232 ? 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	>	100	ug/ml	PMID[16872157]
NPT2	Others	Unspecified	n.a.	IC50	>	100	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 NPC477079 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	21815
0.1-0.2	23687
0.2-0.3	3359
0.3-0.4	579
0.4-0.5	329
0.5-0.6	74
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC477076
0.7642	Intermediate Similarity	NPC477077
0.7064	Intermediate Similarity	NPC477075
0.7	Intermediate Similarity	NPC477078
0.6471	Remote Similarity	NPC277212
0.6471	Remote Similarity	NPC30279
0.6364	Remote Similarity	NPC484061
0.6364	Remote Similarity	NPC484062
0.6198	Remote Similarity	NPC46823
0.6066	Remote Similarity	NPC473918
0.6017	Remote Similarity	NPC605294
0.6016	Remote Similarity	NPC71391
0.5968	Remote Similarity	NPC470518
0.5877	Remote Similarity	NPC251768
0.5862	Remote Similarity	NPC64715
0.584	Remote Similarity	NPC178264
0.5827	Remote Similarity	NPC484059
0.5827	Remote Similarity	NPC484060
0.576	Remote Similarity	NPC329923
0.576	Remote Similarity	NPC475281
0.576	Remote Similarity	NPC192765
0.5726	Remote Similarity	NPC269484
0.5726	Remote Similarity	NPC97918
0.5667	Remote Similarity	NPC329976
0.5664	Remote Similarity	NPC472949
0.5641	Remote Similarity	NPC131469
0.5625	Remote Similarity	NPC225791
0.5593	Remote Similarity	NPC95437
0.5583	Remote Similarity	NPC187618
0.5556	Remote Similarity	NPC47995
0.5546	Remote Similarity	NPC114692
0.5538	Remote Similarity	NPC329657
0.5528	Remote Similarity	NPC609119
0.5512	Remote Similarity	NPC82380
0.5512	Remote Similarity	NPC244296
0.5504	Remote Similarity	NPC258617
0.55	Remote Similarity	NPC301449
0.55	Remote Similarity	NPC218954
0.55	Remote Similarity	NPC601290
0.5496	Remote Similarity	NPC11577
0.5496	Remote Similarity	NPC141600
0.5455	Remote Similarity	NPC120116
0.5426	Remote Similarity	NPC265841
0.5417	Remote Similarity	NPC236657
0.541	Remote Similarity	NPC477194
0.5403	Remote Similarity	NPC313110
0.5391	Remote Similarity	NPC603026
0.5385	Remote Similarity	NPC271610
0.5372	Remote Similarity	NPC482735
0.5366	Remote Similarity	NPC470915
0.5351	Remote Similarity	NPC309780
0.5323	Remote Similarity	NPC472267
0.5323	Remote Similarity	NPC115656
0.5294	Remote Similarity	NPC482722
0.5294	Remote Similarity	NPC471963
0.5289	Remote Similarity	NPC470914
0.525	Remote Similarity	NPC470913
0.5238	Remote Similarity	NPC478600
0.5238	Remote Similarity	NPC478599
0.5234	Remote Similarity	NPC602995
0.52	Remote Similarity	NPC25998
0.5194	Remote Similarity	NPC252289
0.5194	Remote Similarity	NPC305793
0.5191	Remote Similarity	NPC476774
0.5169	Remote Similarity	NPC192791
0.5164	Remote Similarity	NPC482740
0.5159	Remote Similarity	NPC610461
0.5156	Remote Similarity	NPC482736
0.5156	Remote Similarity	NPC482738
0.5124	Remote Similarity	NPC611191
0.5113	Remote Similarity	NPC484833
0.5111	Remote Similarity	NPC476775
0.5086	Remote Similarity	NPC25605
0.5086	Remote Similarity	NPC56713
0.5079	Remote Similarity	NPC107536
0.5079	Remote Similarity	NPC280029
0.5079	Remote Similarity	NPC9470
0.5078	Remote Similarity	NPC482739
0.5078	Remote Similarity	NPC470911
0.5074	Remote Similarity	NPC484063
0.5074	Remote Similarity	NPC484064
0.5048	Remote Similarity	NPC480920
0.5043	Remote Similarity	NPC482748
0.5041	Remote Similarity	NPC118440
0.5039	Remote Similarity	NPC252657
0.5039	Remote Similarity	NPC88311

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6860
0.1-0.2	2243
0.2-0.3	44
0.3-0.4	2
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