NPASS Compound

Natural Product: NPC475486

Natural Product ID	NPC475486
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Glucopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Alpha-L-Arabinopyranosyl]Echinocystic Acid
IUPAC Name	(4aR,5R,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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-5-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	CHEMBL506550
PubChem CID	21603412
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 140147 0 0 0 0 0 0 0 0999 V2000 5.4598 1.3527 4.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6614 0.7510 2.9164 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9841 1.2073 2.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1751 0.6494 1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9992 1.0787 0.1816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6666 0.7712 0.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5913 1.1747 2.1415 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4044 -0.5551 0.6279 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3872 -0.8638 -0.2295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8785 -1.6993 -1.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1253 -3.0027 -1.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 -3.6649 -0.2344 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4061 -2.8223 0.7812 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1845 -1.5084 0.4035 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0838 -1.3776 -0.4372 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0551 -0.5871 0.0936 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1343 -1.5022 0.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4283 -0.8285 0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3880 0.6536 0.4766 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6238 1.0683 -0.7529 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2267 0.5578 -0.8249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6882 1.7566 -0.5528 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1446 0.0864 -2.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4064 0.5950 -1.9251 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7623 1.1993 -2.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5039 1.4531 -0.7608 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7278 1.3376 0.4695 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3974 1.1002 1.7582 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7621 0.6074 1.5159 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4314 0.4118 0.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8090 0.7089 -0.8979 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7650 -0.6356 -1.5894 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7129 -1.6729 -1.0491 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0617 -1.1361 -0.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7968 -0.1834 0.4881 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9451 0.6861 0.8129 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0577 -0.2707 1.2271 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1686 -1.5400 0.5113 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9292 -2.2388 0.0248 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8568 -0.5683 2.7249 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3571 0.4985 1.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9142 -0.7530 -1.7323 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5117 -1.1312 -2.9001 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0804 -0.0531 -1.7608 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2182 -2.4188 -0.0050 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6717 1.5739 -1.8213 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9171 2.9613 -0.8334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 1.1500 1.7489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0487 -2.8410 -2.3872 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2527 -2.0090 -1.2178 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 2.4549 -0.0757 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3227 1.1814 0.4113 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2136 0.2001 -0.0216 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4131 0.3401 -1.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5503 -0.5057 -1.9939 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7638 -0.4182 -1.1306 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3226 -0.5729 0.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4299 0.4452 0.5991 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5455 -0.5651 1.2083 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1616 -0.7154 2.5369 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5063 0.7189 -1.3478 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8781 -0.1165 -3.2862 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2703 -0.1110 -2.1946 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9711 2.5965 2.2935 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1590 2.4112 4.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3920 1.3383 4.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6196 0.8199 4.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6795 -0.3605 3.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7641 0.8415 3.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1664 -0.4445 1.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0063 0.5801 -0.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 1.4457 0.2588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0174 0.1017 -0.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8135 -1.1865 -2.3670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8305 -3.6902 -2.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 -4.2124 0.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9943 -4.4018 -0.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9560 -0.9342 1.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4469 -0.2459 1.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8208 -2.2429 1.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2232 -2.1060 -0.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3069 -1.3255 0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6045 -1.0452 1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6658 2.2001 -0.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2741 1.6577 0.3639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4367 1.9039 -1.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1324 2.7115 -0.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4338 -0.7750 -2.5577 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2165 -0.2526 -2.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1927 0.9363 -2.9553 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4842 -0.5104 -1.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8346 0.7994 -2.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6128 2.1570 -2.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3373 0.5573 -2.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3473 2.4422 0.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5278 2.0459 2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8232 0.4437 2.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3718 0.3418 2.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0660 -0.5212 -2.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7605 -1.0846 -1.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9525 -2.4124 -1.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8071 -0.8683 1.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7010 1.2766 1.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2777 1.3996 0.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9615 -1.5827 -0.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6105 -2.2871 1.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3622 -2.7103 0.8577 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2073 -2.9268 -0.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2946 0.2649 3.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3328 -1.5331 2.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8605 -0.6997 3.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1723 1.5972 1.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9893 0.3622 2.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9584 0.1948 0.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3738 0.6335 -2.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7472 -3.2109 -0.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0759 2.3832 -2.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9608 1.0150 -2.7637 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4899 2.0821 -1.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3408 3.5389 -0.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5704 3.4407 -1.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9494 3.1132 -0.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3537 1.8184 2.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8086 1.8056 1.4982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4304 0.3403 2.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5080 -3.6632 -2.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4439 -2.9108 -1.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2253 2.8833 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9023 -0.8239 0.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5374 1.4074 -1.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2133 -1.5732 -2.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4363 -1.2901 -1.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8402 -1.5800 0.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0626 0.4106 1.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2003 -1.4047 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1778 -0.6579 2.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0327 1.2945 -1.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4373 -0.8048 -3.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2422 -1.1036 -2.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5460 3.0381 2.9617 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 34 42 1 0 42 43 2 0 42 44 1 0 33 45 1 0 31 46 1 0 26 47 1 0 19 48 1 0 11 49 1 0 10 50 1 0 5 51 1 0 4 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 56 61 1 0 55 62 1 0 54 63 1 0 3 64 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 58 53 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 0 3 69 1 0 4 70 1 0 5 71 1 0 6 72 1 0 9 73 1 0 10 74 1 0 11 75 1 0 12 76 1 0 12 77 1 0 14 78 1 0 16 79 1 0 17 80 1 0 17 81 1 0 18 82 1 0 18 83 1 0 20 84 1 0 22 85 1 0 22 86 1 0 22 87 1 0 23 88 1 0 23 89 1 0 23 90 1 0 24 91 1 0 24 92 1 0 25 93 1 0 25 94 1 0 27 95 1 0 28 96 1 0 28 97 1 0 29 98 1 0 32 99 1 0 32100 1 0 33101 1 0 35102 1 0 36103 1 0 36104 1 0 38105 1 0 38106 1 0 39107 1 0 39108 1 0 40109 1 0 40110 1 0 40111 1 0 41112 1 0 41113 1 0 41114 1 0 44115 1 0 45116 1 0 46117 1 0 46118 1 0 46119 1 0 47120 1 0 47121 1 0 47122 1 0 48123 1 0 48124 1 0 48125 1 0 49126 1 0 50127 1 0 51128 1 0 53129 1 0 54130 1 0 55131 1 0 56132 1 0 57133 1 0 59134 1 0 59135 1 0 60136 1 0 61137 1 0 62138 1 0 63139 1 0 64140 1 0 M END

Standard InCHIKey	YCIBWFKSAZNJMF-WYTBTIRESA-N
Standard InCHI	InChI=1S/C47H76O17/c1-21-30(51)36(63-38-34(55)33(54)32(53)25(19-48)61-38)35(56)39(60-21)64-37-31(52)24(49)20-59-40(37)62-29-12-13-44(6)26(43(29,4)5)11-14-45(7)27(44)10-9-22-23-17-42(2,3)15-16-47(23,41(57)58)28(50)18-46(22,45)8/h9,21,23-40,48-56H,10-20H2,1-8H3,(H,57,58)/t21-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+,33-,34+,35+,36+,37+,38-,39-,40-,44-,45+,46+,47+/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CC(C7(C6CC(CC7)(C)C)C(=O)O)O)C)C)C)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	912.51	Volume:	897.177 ? Van der Waals volume.
Dense:	1.017	LogP:	1.397 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.6 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	45.0
TPSA:	274.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.122	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.301	Fsp³:	0.936
MCE-18:	174.462 ? 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:	0.083	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.305 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.175	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.433	MDCK Permeability:	-5.027
Pgp-inhibitor:	0.0	Pgp-substrate:	0.744
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):	0.988
20% Bioavailability (F20%):	0.109	30% Bioavailability (F30%):	0.93
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	1.0
Plasma Protein Binding (PPB):	50.584%	Volume Distribution (VD):	-0.457
Fu:	31.596% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.101	BCRP inhibitor:	0.0
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.733	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.047	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):

-0.044

Half-life (T1/2):

3.575

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.083
Human Hepatotoxicity (H-HT):	0.366	Drug-induced Liver Injury (DILI):	0.157
AMES Toxicity:	0.134	Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.277	Skin Sensitization:	0.005
Carcinogencity:	0.011	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.149	Ototoxicity:	1.0
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.018
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.013	Hek293 Cytotoxicity:	0.474
BCF:	0.849 ? 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:	4.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.334 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.461 ? 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
NPO33015	trevesia palmata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757708]

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	1

Activity Type	# Activity
Cell line	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
NPT1886	Cell line	J774	Mus musculus	IC50	=	190.0	nM	PMID[17417907]

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 NPC475486 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	23838
0.1-0.2	21753
0.2-0.3	2848
0.3-0.4	832
0.4-0.5	382
0.5-0.6	133
0.6-0.7	43
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC80843
0.8614	High Similarity	NPC324875
0.8614	High Similarity	NPC292677
0.7982	Intermediate Similarity	NPC219180
0.7982	Intermediate Similarity	NPC251263
0.7981	Intermediate Similarity	NPC276093
0.7778	Intermediate Similarity	NPC288205
0.7778	Intermediate Similarity	NPC51465
0.7624	Intermediate Similarity	NPC127056
0.7619	Intermediate Similarity	NPC481082
0.7619	Intermediate Similarity	NPC164419
0.75	Intermediate Similarity	NPC166422
0.75	Intermediate Similarity	NPC31839
0.7411	Intermediate Similarity	NPC133818
0.7383	Intermediate Similarity	NPC488515
0.7184	Intermediate Similarity	NPC56713
0.7069	Intermediate Similarity	NPC54636
0.7059	Intermediate Similarity	NPC161717
0.7019	Intermediate Similarity	NPC59804
0.7009	Intermediate Similarity	NPC114304
0.6957	Remote Similarity	NPC323341
0.69	Remote Similarity	NPC242611
0.6887	Remote Similarity	NPC488516
0.6842	Remote Similarity	NPC475119
0.6818	Remote Similarity	NPC257468
0.6698	Remote Similarity	NPC174679
0.6698	Remote Similarity	NPC279554
0.6667	Remote Similarity	NPC471384
0.6638	Remote Similarity	NPC473824
0.6637	Remote Similarity	NPC291903
0.6571	Remote Similarity	NPC164194
0.6542	Remote Similarity	NPC25605
0.6522	Remote Similarity	NPC481078
0.6504	Remote Similarity	NPC471385
0.6496	Remote Similarity	NPC475287
0.6486	Remote Similarity	NPC180550
0.6486	Remote Similarity	NPC35405
0.6441	Remote Similarity	NPC79643
0.6422	Remote Similarity	NPC488561
0.6372	Remote Similarity	NPC275668
0.6372	Remote Similarity	NPC475504
0.6348	Remote Similarity	NPC75318
0.633	Remote Similarity	NPC480424
0.6316	Remote Similarity	NPC79718
0.6293	Remote Similarity	NPC488564
0.6283	Remote Similarity	NPC139044
0.6275	Remote Similarity	NPC606107
0.6273	Remote Similarity	NPC472949
0.6262	Remote Similarity	NPC270667
0.6262	Remote Similarity	NPC76999
0.6198	Remote Similarity	NPC123199
0.6195	Remote Similarity	NPC104400
0.6195	Remote Similarity	NPC10320
0.6182	Remote Similarity	NPC109079
0.6129	Remote Similarity	NPC21691
0.6121	Remote Similarity	NPC37134
0.6071	Remote Similarity	NPC22956
0.6068	Remote Similarity	NPC323359
0.6047	Remote Similarity	NPC220160
0.6032	Remote Similarity	NPC41061
0.6032	Remote Similarity	NPC227551
0.6018	Remote Similarity	NPC112352
0.6	Remote Similarity	NPC12288
0.5938	Remote Similarity	NPC305981
0.592	Remote Similarity	NPC4749
0.5917	Remote Similarity	NPC480939
0.5917	Remote Similarity	NPC62725
0.5913	Remote Similarity	NPC164389
0.5891	Remote Similarity	NPC261506
0.5891	Remote Similarity	NPC4328
0.5862	Remote Similarity	NPC258885
0.5862	Remote Similarity	NPC91838
0.582	Remote Similarity	NPC200788
0.5772	Remote Similarity	NPC151543
0.5769	Remote Similarity	NPC302543
0.5763	Remote Similarity	NPC119794
0.576	Remote Similarity	NPC283417
0.576	Remote Similarity	NPC200049
0.5752	Remote Similarity	NPC114441
0.575	Remote Similarity	NPC488209
0.5739	Remote Similarity	NPC469945
0.5738	Remote Similarity	NPC476992
0.5726	Remote Similarity	NPC471383
0.5714	Remote Similarity	NPC204407
0.566	Remote Similarity	NPC283849
0.5656	Remote Similarity	NPC280941
0.5656	Remote Similarity	NPC235772
0.5635	Remote Similarity	NPC475140
0.56	Remote Similarity	NPC243680
0.5593	Remote Similarity	NPC63159
0.5588	Remote Similarity	NPC601365
0.5575	Remote Similarity	NPC136877
0.5573	Remote Similarity	NPC236638
0.5573	Remote Similarity	NPC294453
0.5565	Remote Similarity	NPC6377
0.5565	Remote Similarity	NPC208381
0.5556	Remote Similarity	NPC160415
0.5537	Remote Similarity	NPC23275
0.5536	Remote Similarity	NPC211798
0.55	Remote Similarity	NPC302887
0.5496	Remote Similarity	NPC293330
0.5492	Remote Similarity	NPC187618
0.5492	Remote Similarity	NPC160452
0.5462	Remote Similarity	NPC265841
0.5462	Remote Similarity	NPC488308
0.5462	Remote Similarity	NPC110633
0.5455	Remote Similarity	NPC145899
0.5455	Remote Similarity	NPC481081
0.5455	Remote Similarity	NPC111466
0.5426	Remote Similarity	NPC85154
0.5426	Remote Similarity	NPC488211
0.542	Remote Similarity	NPC312650
0.5414	Remote Similarity	NPC298034
0.5414	Remote Similarity	NPC71065
0.5407	Remote Similarity	NPC250247
0.5391	Remote Similarity	NPC475296
0.5379	Remote Similarity	NPC43550
0.5378	Remote Similarity	NPC44716
0.5378	Remote Similarity	NPC480475
0.5372	Remote Similarity	NPC64715
0.5333	Remote Similarity	NPC488309
0.5323	Remote Similarity	NPC104137
0.5323	Remote Similarity	NPC26626
0.5312	Remote Similarity	NPC135904
0.5303	Remote Similarity	NPC271610
0.5294	Remote Similarity	NPC124296
0.5294	Remote Similarity	NPC117714
0.5294	Remote Similarity	NPC30289
0.5289	Remote Similarity	NPC73829
0.5289	Remote Similarity	NPC123796
0.5285	Remote Similarity	NPC301449
0.5285	Remote Similarity	NPC601290
0.528	Remote Similarity	NPC11242
0.5259	Remote Similarity	NPC474589
0.525	Remote Similarity	NPC251768
0.5246	Remote Similarity	NPC471435
0.5246	Remote Similarity	NPC471434
0.5246	Remote Similarity	NPC484832
0.5242	Remote Similarity	NPC480473
0.5242	Remote Similarity	NPC480474
0.5229	Remote Similarity	NPC28198
0.5229	Remote Similarity	NPC476123
0.5227	Remote Similarity	NPC286457
0.5224	Remote Similarity	NPC136768
0.5221	Remote Similarity	NPC191410
0.5221	Remote Similarity	NPC488212
0.521	Remote Similarity	NPC192791
0.5208	Remote Similarity	NPC40085
0.5203	Remote Similarity	NPC114484
0.5197	Remote Similarity	NPC313110
0.5191	Remote Similarity	NPC481080
0.5161	Remote Similarity	NPC218954
0.5159	Remote Similarity	NPC480936
0.5154	Remote Similarity	NPC191827
0.5152	Remote Similarity	NPC57484
0.5149	Remote Similarity	NPC228784
0.5149	Remote Similarity	NPC324341
0.5149	Remote Similarity	NPC601810
0.5133	Remote Similarity	NPC475633
0.513	Remote Similarity	NPC1046
0.5126	Remote Similarity	NPC263756
0.5126	Remote Similarity	NPC213674
0.5126	Remote Similarity	NPC469946
0.5124	Remote Similarity	NPC159309
0.5124	Remote Similarity	NPC86222
0.5116	Remote Similarity	NPC284449
0.5111	Remote Similarity	NPC202828
0.5111	Remote Similarity	NPC119592
0.5108	Remote Similarity	NPC489209
0.5083	Remote Similarity	NPC223301
0.5083	Remote Similarity	NPC171544
0.5082	Remote Similarity	NPC475591
0.5082	Remote Similarity	NPC236870
0.5081	Remote Similarity	NPC104372
0.5079	Remote Similarity	NPC469947
0.5079	Remote Similarity	NPC207738
0.5079	Remote Similarity	NPC480948
0.5079	Remote Similarity	NPC187290
0.5078	Remote Similarity	NPC60557
0.5078	Remote Similarity	NPC67857
0.5078	Remote Similarity	NPC610204
0.5076	Remote Similarity	NPC71391
0.5071	Remote Similarity	NPC120667
0.5071	Remote Similarity	NPC278272
0.5043	Remote Similarity	NPC203354
0.5043	Remote Similarity	NPC475472
0.5041	Remote Similarity	NPC605226
0.504	Remote Similarity	NPC481079
0.5039	Remote Similarity	NPC123522
0.5039	Remote Similarity	NPC75287
0.5038	Remote Similarity	NPC484061
0.5038	Remote Similarity	NPC484062
0.5037	Remote Similarity	NPC484059
0.5037	Remote Similarity	NPC484060
0.5035	Remote Similarity	NPC33012
0.5034	Remote Similarity	NPC264270

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6920
0.1-0.2	2166
0.2-0.3	60
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