NPASS Compound

Natural Product: NPC471384

Natural Product ID	NPC471384
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3 Beta-O-{Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl}Siaresinolic Acid
IUPAC Name	(1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2430036
PubChem CID	72189837
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 157165 0 0 0 0 0 0 0 0999 V2000 -4.7759 0.6556 -2.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9734 1.7665 -2.1108 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8268 2.9489 -1.8263 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8407 3.2125 -0.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9332 1.8574 0.3143 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5303 1.1483 0.1336 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 1.3037 -1.1485 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6223 0.0095 0.7223 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5657 -0.9195 1.5089 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8288 -1.7533 1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5181 -3.1870 1.5573 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5155 -3.5289 2.6519 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3933 -2.8364 2.4297 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3360 -1.8935 1.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2355 -1.0646 1.7056 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2016 -1.1132 0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0273 0.2982 0.2782 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3382 0.6932 -0.1371 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1951 -0.4826 -0.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2070 -1.5279 0.4482 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1073 -1.5168 1.4268 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3323 -0.7380 2.6811 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8637 -2.9722 1.8810 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5100 -1.5604 1.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7401 -1.7330 0.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6649 -0.9855 -0.9769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5957 0.0041 -0.7915 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7677 1.1985 -1.7183 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0195 1.8351 -1.1951 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0564 1.0425 -1.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9936 -0.3730 -1.3304 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1341 -1.1914 -0.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9935 -0.6109 0.2489 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8458 0.8223 0.5743 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2979 1.6715 -0.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3074 1.9863 -1.5626 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2398 3.0449 -0.9735 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2592 2.8945 0.5211 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1967 1.4501 0.9564 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6374 4.3798 -1.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6289 2.9743 -1.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0516 0.9193 -2.0074 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0203 0.9635 1.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9382 1.5915 1.8577 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4524 0.3812 3.0262 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2065 -0.4289 -2.8697 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4084 -2.0777 -1.9746 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5230 -0.9192 -1.8977 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5988 -4.0595 1.5863 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6067 -4.9336 0.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4442 -6.3731 1.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4312 -7.2840 0.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4317 -7.0607 -1.1159 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6525 -5.6099 -1.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7359 -4.8104 -0.2446 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7619 -5.3499 -2.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6834 -4.0123 -2.7722 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1697 -7.4226 -1.6018 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0996 -8.5908 0.7215 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 -6.7273 0.8818 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8155 -1.4196 0.8148 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0958 2.0406 1.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9244 3.9823 -0.0071 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5422 5.2018 0.5842 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1156 5.3086 1.9556 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3579 6.1978 1.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9812 7.5764 1.4996 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8823 7.4780 0.4873 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9617 6.2745 -0.1841 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4845 8.3737 2.5480 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9521 6.2262 3.2034 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1594 5.9675 2.7677 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0958 2.7132 -2.3501 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3265 1.0394 -3.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0553 -0.1134 -3.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4300 0.1077 -2.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2716 2.1106 -2.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4179 3.8918 -2.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8809 3.6939 -0.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7308 1.2154 -0.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9126 1.9488 0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3094 -0.5234 2.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2631 -1.5961 2.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9801 -3.4041 0.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2954 -4.6231 2.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9240 -3.2927 3.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2768 -2.4174 0.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3595 -1.8330 -0.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3955 0.9963 1.0527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7728 0.3769 -0.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8872 1.3429 0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1693 1.3262 -1.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1517 -2.5167 -0.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7091 -1.3521 3.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3199 -0.3672 3.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9482 0.1503 2.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3022 -2.8929 2.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3181 -3.5389 1.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8058 -3.4928 2.1340 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6476 -0.6893 1.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4707 -2.4393 1.8879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5876 -1.3684 0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9274 -2.8162 0.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7951 0.4687 0.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7765 0.9611 -2.7723 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9758 1.9528 -1.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0872 2.8999 -0.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8147 -1.5454 -1.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7096 -2.1616 -0.4440 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0927 -0.7429 -0.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9505 -1.1802 1.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0122 2.6513 -0.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7798 2.4169 -2.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2358 3.2969 0.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4937 3.4948 1.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3661 1.4324 2.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9868 0.8976 0.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 4.5342 -0.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3712 5.2067 -1.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2224 4.3231 -2.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1531 3.9116 -1.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1602 2.0742 -1.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5465 3.0059 -2.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1977 0.9639 -2.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8985 0.4332 3.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6445 0.4856 -3.2690 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3181 -0.6846 -3.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9574 -1.2306 -3.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3921 -2.4005 -2.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7776 -1.8551 -2.8168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0107 -3.0179 -1.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9611 -0.3046 -2.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4311 -0.6212 -1.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5205 -1.9921 -2.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7384 -4.7645 -0.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 -6.3431 2.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4193 -7.0809 0.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2365 -7.6270 -1.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7192 -5.2225 -1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7653 -5.6393 -2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5377 -5.9970 -3.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1632 -3.9562 -3.6141 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2053 -8.3138 -2.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9390 -8.6381 1.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9570 -7.5696 0.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9530 -2.1334 0.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9639 1.6801 2.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4287 5.2453 0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4061 4.3464 2.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0473 5.7567 1.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9084 8.0602 1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8794 7.6485 0.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0639 8.2921 -0.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6399 9.3202 2.2418 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3885 6.6496 3.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 5.5510 2.5751 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7897 2.8123 -1.6630 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 37 40 1 0 37 41 1 0 36 42 1 0 34 43 1 0 43 44 2 0 43 45 1 0 31 46 1 0 26 47 1 0 19 48 1 0 11 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 53 58 1 0 52 59 1 0 51 60 1 0 10 61 1 0 5 62 1 0 4 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 67 70 1 0 66 71 1 0 65 72 1 0 3 73 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 55 50 1 0 69 64 1 0 1 74 1 0 1 75 1 0 1 76 1 0 2 77 1 0 3 78 1 0 4 79 1 0 5 80 1 0 6 81 1 0 9 82 1 0 10 83 1 0 11 84 1 0 12 85 1 0 12 86 1 0 14 87 1 0 16 88 1 0 17 89 1 0 17 90 1 0 18 91 1 0 18 92 1 0 20 93 1 0 22 94 1 0 22 95 1 0 22 96 1 0 23 97 1 0 23 98 1 0 23 99 1 0 24100 1 0 24101 1 0 25102 1 0 25103 1 0 27104 1 0 28105 1 0 28106 1 0 29107 1 0 32108 1 0 32109 1 0 33110 1 0 33111 1 0 35112 1 0 36113 1 0 38114 1 0 38115 1 0 39116 1 0 39117 1 0 40118 1 0 40119 1 0 40120 1 0 41121 1 0 41122 1 0 41123 1 0 42124 1 0 45125 1 0 46126 1 0 46127 1 0 46128 1 0 47129 1 0 47130 1 0 47131 1 0 48132 1 0 48133 1 0 48134 1 0 50135 1 0 51136 1 0 52137 1 0 53138 1 0 54139 1 0 56140 1 0 56141 1 0 57142 1 0 58143 1 0 59144 1 0 60145 1 0 61146 1 0 62147 1 0 64148 1 0 65149 1 0 66150 1 0 67151 1 0 68152 1 0 68153 1 0 70154 1 0 71155 1 0 72156 1 0 73157 1 0 M END

Standard InCHIKey	YYNGQYRUWXEJIJ-ZNTOFBKISA-N
Standard InCHI	InChI=1S/C52H84O21/c1-22-31(55)39(72-42-36(60)32(56)24(54)20-66-42)38(62)44(68-22)73-40-34(58)26(70-43-37(61)35(59)33(57)25(19-53)69-43)21-67-45(40)71-29-12-13-49(6)27(48(29,4)5)11-14-51(8)28(49)10-9-23-30-41(63)47(2,3)15-17-52(30,46(64)65)18-16-50(23,51)7/h9,22,24-45,53-63H,10-21H2,1-8H3,(H,64,65)/t22-,24+,25+,26-,27-,28+,29-,30+,31-,32-,33+,34-,35-,36+,37+,38+,39+,40+,41-,42-,43-,44-,45-,49-,50+,51+,52-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6C(C(CC7)(C)C)O)C(=O)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)O)O)O)OC9C(C(C(CO9)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1044.55	Volume:	1010.261 ? Van der Waals volume.
Dense:	1.034	LogP:	0.376 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.386 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.342 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	51.0
TPSA:	333.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	12.0	Rings:	9.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.74	Fsp³:	0.942
MCE-18:	195.446 ? 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:	0.021	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.392 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.33	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.788	MDCK Permeability:	-4.835
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	0.999
20% Bioavailability (F20%):	0.481	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	43.388%	Volume Distribution (VD):	-0.469
Fu:	30.944% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.036	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.208	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.369

Half-life (T1/2):

3.877

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.147
Human Hepatotoxicity (H-HT):	0.263	Drug-induced Liver Injury (DILI):	0.221
AMES Toxicity:	0.186	Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.328	Skin Sensitization:	0.007
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.241	Ototoxicity:	1.0
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.03
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.664
BCF:	0.559 ? 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:	4.134 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.227 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.177 ? 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
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23992864]
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	4
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	80000.0	nM	PMID[18676884]
NPT81	Cell line	A549	Homo sapiens	IC50	=	53140.0	nM	PMID[23190013]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	38640.0	nM	PMID[23665143]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	35720.0	nM	DrugMatrix in vitro pharmacology data
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	57280.0	nM	PMID[23992864]

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 NPC471384 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	24623
0.1-0.2	21101
0.2-0.3	2779
0.3-0.4	732
0.4-0.5	445
0.5-0.6	133
0.6-0.7	29
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC166422
0.8018	Intermediate Similarity	NPC323341
0.75	Intermediate Similarity	NPC54636
0.7479	Intermediate Similarity	NPC471385
0.7478	Intermediate Similarity	NPC219180
0.7387	Intermediate Similarity	NPC324875
0.7387	Intermediate Similarity	NPC292677
0.7273	Intermediate Similarity	NPC257468
0.7117	Intermediate Similarity	NPC481082
0.7117	Intermediate Similarity	NPC164419
0.6891	Remote Similarity	NPC251263
0.6842	Remote Similarity	NPC276093
0.6726	Remote Similarity	NPC139044
0.6724	Remote Similarity	NPC488564
0.672	Remote Similarity	NPC136768
0.6667	Remote Similarity	NPC475486
0.664	Remote Similarity	NPC161717
0.6557	Remote Similarity	NPC475140
0.6496	Remote Similarity	NPC323359
0.6486	Remote Similarity	NPC127056
0.6429	Remote Similarity	NPC488561
0.6404	Remote Similarity	NPC114304
0.6393	Remote Similarity	NPC133818
0.6385	Remote Similarity	NPC250247
0.6348	Remote Similarity	NPC104400
0.6348	Remote Similarity	NPC10320
0.6341	Remote Similarity	NPC123199
0.625	Remote Similarity	NPC481078
0.623	Remote Similarity	NPC473824
0.6186	Remote Similarity	NPC79718
0.6179	Remote Similarity	NPC151543
0.6179	Remote Similarity	NPC79643
0.6154	Remote Similarity	NPC471383
0.6106	Remote Similarity	NPC56713
0.6094	Remote Similarity	NPC110633
0.6016	Remote Similarity	NPC475119
0.6016	Remote Similarity	NPC288205
0.6016	Remote Similarity	NPC51465
0.6	Remote Similarity	NPC43550
0.5982	Remote Similarity	NPC164194
0.5968	Remote Similarity	NPC610204
0.5966	Remote Similarity	NPC275668
0.5965	Remote Similarity	NPC25605
0.5965	Remote Similarity	NPC59804
0.595	Remote Similarity	NPC291903
0.5932	Remote Similarity	NPC180550
0.5932	Remote Similarity	NPC35405
0.5917	Remote Similarity	NPC484832
0.5906	Remote Similarity	NPC191827
0.5887	Remote Similarity	NPC476992
0.5882	Remote Similarity	NPC258885
0.5868	Remote Similarity	NPC37134
0.5862	Remote Similarity	NPC472949
0.5854	Remote Similarity	NPC609281
0.5847	Remote Similarity	NPC204392
0.582	Remote Similarity	NPC606145
0.5812	Remote Similarity	NPC80843
0.5802	Remote Similarity	NPC41061
0.5802	Remote Similarity	NPC227551
0.5785	Remote Similarity	NPC488515
0.5775	Remote Similarity	NPC40085
0.5763	Remote Similarity	NPC469945
0.576	Remote Similarity	NPC185466
0.5714	Remote Similarity	NPC475287
0.5714	Remote Similarity	NPC236638
0.5714	Remote Similarity	NPC294453
0.5714	Remote Similarity	NPC305981
0.5714	Remote Similarity	NPC481081
0.5704	Remote Similarity	NPC488212
0.5702	Remote Similarity	NPC270667
0.5702	Remote Similarity	NPC475504
0.5702	Remote Similarity	NPC123796
0.5692	Remote Similarity	NPC481080
0.569	Remote Similarity	NPC174679
0.569	Remote Similarity	NPC279554
0.5688	Remote Similarity	NPC283849
0.5688	Remote Similarity	NPC606107
0.568	Remote Similarity	NPC280941
0.568	Remote Similarity	NPC235772
0.568	Remote Similarity	NPC606553
0.5672	Remote Similarity	NPC261506
0.5672	Remote Similarity	NPC4328
0.5656	Remote Similarity	NPC471435
0.5656	Remote Similarity	NPC471434
0.5656	Remote Similarity	NPC119794
0.5639	Remote Similarity	NPC65105
0.5625	Remote Similarity	NPC470911
0.5603	Remote Similarity	NPC136877
0.5593	Remote Similarity	NPC6377
0.5593	Remote Similarity	NPC208381
0.5591	Remote Similarity	NPC610461
0.5588	Remote Similarity	NPC220160
0.5586	Remote Similarity	NPC264270
0.5581	Remote Similarity	NPC603137
0.5537	Remote Similarity	NPC173859
0.5537	Remote Similarity	NPC148603
0.5522	Remote Similarity	NPC293330
0.552	Remote Similarity	NPC488209
0.5508	Remote Similarity	NPC109079
0.5492	Remote Similarity	NPC91838
0.5481	Remote Similarity	NPC111466
0.5476	Remote Similarity	NPC207738
0.547	Remote Similarity	NPC12288
0.5469	Remote Similarity	NPC607904
0.5462	Remote Similarity	NPC470512
0.5462	Remote Similarity	NPC488516
0.5447	Remote Similarity	NPC73829
0.5441	Remote Similarity	NPC302543
0.544	Remote Similarity	NPC301449
0.544	Remote Similarity	NPC481079
0.544	Remote Similarity	NPC601290
0.5431	Remote Similarity	NPC211798
0.5417	Remote Similarity	NPC22956
0.5372	Remote Similarity	NPC240734
0.5368	Remote Similarity	NPC202828
0.5368	Remote Similarity	NPC119592
0.5366	Remote Similarity	NPC63159
0.536	Remote Similarity	NPC78034
0.5344	Remote Similarity	NPC609305
0.5338	Remote Similarity	NPC4749
0.5328	Remote Similarity	NPC298034
0.5328	Remote Similarity	NPC71065
0.5328	Remote Similarity	NPC309714
0.5312	Remote Similarity	NPC470915
0.5289	Remote Similarity	NPC213674
0.5289	Remote Similarity	NPC469946
0.5268	Remote Similarity	NPC28198
0.5268	Remote Similarity	NPC476123
0.5267	Remote Similarity	NPC243680
0.525	Remote Similarity	NPC114441
0.5246	Remote Similarity	NPC112352
0.5221	Remote Similarity	NPC177246
0.5217	Remote Similarity	NPC128925
0.5203	Remote Similarity	NPC124296
0.5194	Remote Similarity	NPC75287
0.5194	Remote Similarity	NPC62725
0.5188	Remote Similarity	NPC283417
0.5188	Remote Similarity	NPC470218
0.5188	Remote Similarity	NPC200049
0.5185	Remote Similarity	NPC21691
0.5179	Remote Similarity	NPC204407
0.5164	Remote Similarity	NPC263756
0.5156	Remote Similarity	NPC187618
0.5147	Remote Similarity	NPC265841
0.5147	Remote Similarity	NPC488308
0.5133	Remote Similarity	NPC57362
0.513	Remote Similarity	NPC242611
0.512	Remote Similarity	NPC105800
0.512	Remote Similarity	NPC470515
0.5116	Remote Similarity	NPC187290
0.5115	Remote Similarity	NPC200788
0.5113	Remote Similarity	NPC135904
0.5111	Remote Similarity	NPC488211
0.5109	Remote Similarity	NPC271610
0.5109	Remote Similarity	NPC312650
0.5085	Remote Similarity	NPC90856
0.5081	Remote Similarity	NPC160415
0.5079	Remote Similarity	NPC470513
0.5079	Remote Similarity	NPC297263
0.5077	Remote Similarity	NPC11242
0.5074	Remote Similarity	NPC57484
0.5071	Remote Similarity	NPC70809
0.5069	Remote Similarity	NPC33012
0.5065	Remote Similarity	NPC478559
0.5065	Remote Similarity	NPC478560
0.5043	Remote Similarity	NPC31839
0.5041	Remote Similarity	NPC108748
0.504	Remote Similarity	NPC251768
0.504	Remote Similarity	NPC473383
0.5038	Remote Similarity	NPC284449
0.5037	Remote Similarity	NPC189575
0.5035	Remote Similarity	NPC488309

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7102
0.1-0.2	1994
0.2-0.3	51
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