NPASS Compound

Natural Product: NPC171544

Natural Product ID	NPC171544
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Glucopyranosyl(1->3)-Beta-D-Glucuronopyranoside-28-O-Beta-D-Glucopyranosyl Oleanolic Acid Methyl Ester
IUPAC Name	methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1288838
PubChem CID	52945763
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 146153 0 0 0 0 0 0 0 0999 V2000 -7.7071 -3.0062 1.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6388 -2.3666 0.1131 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7542 -3.5471 -0.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3416 -1.8686 -1.0986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4537 -1.0343 -1.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8665 0.1048 -1.1779 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9375 0.8485 -2.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5885 0.2965 -2.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9277 -0.3579 -1.1283 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6342 -1.7918 -1.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7637 -0.3676 0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1651 -0.4851 1.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7284 -0.6099 1.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9872 -0.5747 0.2835 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5287 -0.4142 0.4475 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8024 0.9116 1.0383 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0349 -1.5207 1.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4975 -1.4206 1.5071 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3050 -1.1691 0.2480 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5171 -1.0932 -0.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5684 -2.5358 -1.5912 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3088 -0.3232 -2.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0939 -0.6692 -0.9084 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6897 0.4970 -1.7687 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8071 0.5765 -1.9432 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6050 0.3252 -0.7168 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0636 1.6592 -0.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1610 -0.0881 0.4224 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4750 -0.3867 0.5741 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4949 0.4210 -0.1425 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7975 -0.4016 -0.1476 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0689 -0.9774 1.1931 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9241 -1.1218 2.1199 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4481 -0.9522 3.5246 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9090 -0.1365 4.3060 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5241 -1.6876 3.9743 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0072 -1.5271 5.2904 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -0.2698 1.9500 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5987 -2.2808 1.0179 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7762 0.4919 -0.5555 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3966 0.2066 -1.7360 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2950 1.3117 -2.7719 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9912 2.5610 -2.2746 C 0 0 2 0 0 0 0 0 0 0 0 0 11.4257 2.1991 -2.0550 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5081 1.0013 -1.1384 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3015 1.4270 0.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1608 2.5121 0.6061 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7283 -0.0557 -1.5161 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0453 1.9386 -3.2850 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3547 3.1072 -1.1818 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9608 0.9309 -3.9542 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1985 0.8359 -1.4109 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2514 -0.2392 0.1210 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8873 -1.3446 0.8840 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0172 1.0500 -0.9206 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0150 2.1932 -1.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0983 0.7502 -0.1269 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1441 1.6837 0.0709 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4460 1.0012 -0.2672 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1273 0.4160 0.9524 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.4714 1.5704 1.8878 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4619 2.6564 1.6761 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2919 3.5069 2.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4701 4.1622 3.2694 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2261 2.0514 1.4208 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7792 1.9576 1.5833 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2674 -0.4115 1.6742 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3644 1.8627 -0.8618 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6843 -2.5017 0.8528 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3736 -2.8351 2.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7623 -4.0922 0.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4617 -4.4077 -0.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2511 -3.3606 -1.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0968 -3.8824 0.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3318 -1.4420 -0.8536 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5934 -2.7874 -1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1087 -0.5555 -2.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7597 -1.6535 -2.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9704 1.9234 -1.8125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4589 0.8413 -3.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6076 -0.4000 -3.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9227 1.1258 -2.6280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4439 -2.1139 -2.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7095 -1.9649 -2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8088 -2.4820 -0.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8132 -0.4863 2.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4203 0.1113 2.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5756 -1.6191 2.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0449 -1.6258 -0.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8758 1.1458 1.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3765 1.7725 0.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4028 0.9054 2.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6694 -2.5127 1.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5640 -1.3390 2.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7313 -0.5765 2.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8308 -2.3259 2.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0191 -2.0523 0.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6281 -2.7595 -1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2317 -3.2754 -0.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9875 -2.5148 -2.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8927 -0.4900 -3.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4877 0.7174 -1.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2805 -0.9122 -2.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4955 -1.5280 -1.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0927 0.3111 -2.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1451 1.4688 -1.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9962 1.6319 -2.2705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1313 -0.0540 -2.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9625 1.6700 0.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1444 1.8588 -0.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5586 2.5278 -0.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6206 -1.4665 0.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7388 1.3451 0.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6241 -1.2293 -0.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8961 -0.4061 1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4934 -2.1678 2.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8162 -0.5478 5.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4687 -2.2760 5.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0806 -1.8335 5.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4304 -2.1600 0.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9830 -0.7572 -2.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2772 1.5754 -3.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9439 3.2782 -3.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9657 3.0734 -1.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5922 0.6164 -1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2915 1.8166 0.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6008 0.5943 0.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0554 2.1460 0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0441 2.0063 -3.2135 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6506 4.0298 -0.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9860 -0.0539 -4.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7426 1.7064 -1.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3980 0.6828 0.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0756 -1.8890 1.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5764 -0.9857 1.6964 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9753 2.6216 -0.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2735 0.1816 -1.0154 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0108 -0.1318 0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4559 1.1890 2.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7603 3.3407 0.8570 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9466 2.9188 3.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5224 4.3038 2.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0895 4.2823 2.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3748 1.3473 2.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8714 0.0418 2.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1683 1.3563 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 44 49 1 0 43 50 1 0 42 51 1 0 30 52 1 0 11 53 1 0 53 54 1 0 6 55 1 1 55 56 2 0 55 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 60 67 1 0 59 68 1 0 54 2 1 0 65 58 1 0 53 6 1 0 26 9 1 0 38 29 1 0 48 41 1 0 26 14 1 0 23 15 1 0 1 69 1 0 1 70 1 0 1 71 1 0 3 72 1 0 3 73 1 0 3 74 1 0 4 75 1 0 4 76 1 0 5 77 1 0 5 78 1 0 7 79 1 0 7 80 1 0 8 81 1 0 8 82 1 0 10 83 1 0 10 84 1 0 10 85 1 0 12 86 1 0 13 87 1 0 13 88 1 0 14 89 1 6 16 90 1 0 16 91 1 0 16 92 1 0 17 93 1 0 17 94 1 0 18 95 1 0 18 96 1 0 19 97 1 6 21 98 1 0 21 99 1 0 21100 1 0 22101 1 0 22102 1 0 22103 1 0 23104 1 6 24105 1 0 24106 1 0 25107 1 0 25108 1 0 27109 1 0 27110 1 0 27111 1 0 29112 1 6 30113 1 1 31114 1 6 32115 1 1 33116 1 1 37117 1 0 37118 1 0 37119 1 0 39120 1 0 41121 1 6 42122 1 6 43123 1 6 44124 1 1 45125 1 1 46126 1 0 46127 1 0 47128 1 0 49129 1 0 50130 1 0 51131 1 0 52132 1 0 53133 1 1 54134 1 0 54135 1 0 58136 1 6 59137 1 6 60138 1 6 61139 1 1 62140 1 6 63141 1 0 63142 1 0 64143 1 0 66144 1 0 67145 1 0 68146 1 0 M END

Standard InCHIKey	FBNHNCMZFHURCE-JYXBHEQSSA-N
Standard InCHI	InChI=1S/C49H78O19/c1-44(2)15-17-49(43(61)68-41-34(57)32(55)30(53)25(21-51)64-41)18-16-47(6)22(23(49)19-44)9-10-27-46(5)13-12-28(45(3,4)26(46)11-14-48(27,47)7)65-42-36(59)37(35(58)38(67-42)39(60)62-8)66-40-33(56)31(54)29(52)24(20-50)63-40/h9,23-38,40-42,50-59H,10-21H2,1-8H3/t23-,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,40-,41-,42+,46-,47+,48+,49-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O3)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	970.51	Volume:	946.713 ? Van der Waals volume.
Dense:	1.025	LogP:	1.565 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.276 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.254 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	46.0
TPSA:	301.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.085	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.34	Fsp³:	0.918
MCE-18:	175.66 ? 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:	0.938	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.205	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.068	MDCK Permeability:	-5.139
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.996 ? 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):	0.811
20% Bioavailability (F20%):	0.616	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219	MRP1:	0.006
Plasma Protein Binding (PPB):	70.655%	Volume Distribution (VD):	-0.344
Fu:	21.969% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.005

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:	0.05
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.319 ? 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):

-0.094

Half-life (T1/2):

4.371

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.73	Drug-induced Liver Injury (DILI):	0.965
AMES Toxicity:	0.891	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.076	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.407	Drug-induced Nephrotoxicity:	0.987
Genotoxicity:	0.414	RPMI-8226 Immunitoxicity:	0.202
A549 Cytotoxicity:	0.514	Hek293 Cytotoxicity:	0.362
BCF:	1.361 ? 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:	4.064 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.877 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.912 ? 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
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951582]
NPO1994	Panax stipuleanatus	Species	Araliaceae	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	2

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	83900.0	nM	PMID[17254669]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[10579870]

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 NPC171544 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	20972
0.1-0.2	24296
0.2-0.3	3330
0.3-0.4	738
0.4-0.5	306
0.5-0.6	116
0.6-0.7	60
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223301
0.8851	High Similarity	NPC214484
0.8737	High Similarity	NPC104372
0.8065	Intermediate Similarity	NPC475516
0.7938	Intermediate Similarity	NPC10607
0.7835	Intermediate Similarity	NPC30735
0.7789	Intermediate Similarity	NPC249848
0.7789	Intermediate Similarity	NPC107966
0.7708	Intermediate Similarity	NPC39211
0.766	Intermediate Similarity	NPC48499
0.7576	Intermediate Similarity	NPC159309
0.7576	Intermediate Similarity	NPC86222
0.75	Intermediate Similarity	NPC235405
0.7426	Intermediate Similarity	NPC297263
0.7282	Intermediate Similarity	NPC114484
0.7238	Intermediate Similarity	NPC481078
0.713	Intermediate Similarity	NPC79643
0.7087	Intermediate Similarity	NPC222580
0.7071	Intermediate Similarity	NPC150400
0.7059	Intermediate Similarity	NPC180550
0.7059	Intermediate Similarity	NPC35405
0.703	Intermediate Similarity	NPC112352
0.7	Intermediate Similarity	NPC157868
0.699	Remote Similarity	NPC235438
0.6981	Remote Similarity	NPC80986
0.6964	Remote Similarity	NPC481080
0.6931	Remote Similarity	NPC469946
0.6903	Remote Similarity	NPC476068
0.6893	Remote Similarity	NPC40775
0.6893	Remote Similarity	NPC251768
0.6881	Remote Similarity	NPC475287
0.6863	Remote Similarity	NPC192791
0.6847	Remote Similarity	NPC123199
0.6827	Remote Similarity	NPC63159
0.6792	Remote Similarity	NPC281148
0.6786	Remote Similarity	NPC475160
0.6786	Remote Similarity	NPC473714
0.6762	Remote Similarity	NPC475504
0.6739	Remote Similarity	NPC167383
0.6735	Remote Similarity	NPC90856
0.6731	Remote Similarity	NPC46665
0.6667	Remote Similarity	NPC475591
0.6667	Remote Similarity	NPC236870
0.6638	Remote Similarity	NPC41061
0.6638	Remote Similarity	NPC227551
0.6606	Remote Similarity	NPC31838
0.6596	Remote Similarity	NPC237503
0.6581	Remote Similarity	NPC43550
0.6571	Remote Similarity	NPC473459
0.6569	Remote Similarity	NPC58448
0.6569	Remote Similarity	NPC473373
0.6525	Remote Similarity	NPC305981
0.6525	Remote Similarity	NPC481081
0.6505	Remote Similarity	NPC295371
0.6471	Remote Similarity	NPC261506
0.6471	Remote Similarity	NPC4328
0.6422	Remote Similarity	NPC301449
0.6422	Remote Similarity	NPC481079
0.6422	Remote Similarity	NPC601290
0.6364	Remote Similarity	NPC209894
0.6346	Remote Similarity	NPC473884
0.6337	Remote Similarity	NPC1046
0.6321	Remote Similarity	NPC309714
0.6311	Remote Similarity	NPC250247
0.6306	Remote Similarity	NPC187290
0.6293	Remote Similarity	NPC488560
0.6262	Remote Similarity	NPC480475
0.6226	Remote Similarity	NPC242840
0.6216	Remote Similarity	NPC295823
0.6216	Remote Similarity	NPC174720
0.6216	Remote Similarity	NPC475467
0.6207	Remote Similarity	NPC470218
0.6176	Remote Similarity	NPC29069
0.6147	Remote Similarity	NPC609763
0.6121	Remote Similarity	NPC135904
0.6116	Remote Similarity	NPC236638
0.6116	Remote Similarity	NPC294453
0.6111	Remote Similarity	NPC2370
0.61	Remote Similarity	NPC128925
0.6078	Remote Similarity	NPC204458
0.6033	Remote Similarity	NPC293330
0.6033	Remote Similarity	NPC65105
0.6019	Remote Similarity	NPC78046
0.5965	Remote Similarity	NPC11242
0.595	Remote Similarity	NPC475514
0.5943	Remote Similarity	NPC173583
0.5935	Remote Similarity	NPC298034
0.5935	Remote Similarity	NPC71065
0.5932	Remote Similarity	NPC471550
0.5887	Remote Similarity	NPC70809
0.5862	Remote Similarity	NPC60557
0.5862	Remote Similarity	NPC67857
0.5859	Remote Similarity	NPC306746
0.5859	Remote Similarity	NPC199457
0.5833	Remote Similarity	NPC473343
0.5826	Remote Similarity	NPC75287
0.582	Remote Similarity	NPC258617
0.5818	Remote Similarity	NPC164389
0.5804	Remote Similarity	NPC64715
0.5798	Remote Similarity	NPC191827
0.5789	Remote Similarity	NPC480473
0.5789	Remote Similarity	NPC480474
0.5785	Remote Similarity	NPC57484
0.578	Remote Similarity	NPC75417
0.5766	Remote Similarity	NPC258885
0.5727	Remote Similarity	NPC160415
0.5701	Remote Similarity	NPC139894
0.5688	Remote Similarity	NPC213674
0.568	Remote Similarity	NPC302543
0.5678	Remote Similarity	NPC192600
0.5656	Remote Similarity	NPC21691
0.5652	Remote Similarity	NPC241909
0.5652	Remote Similarity	NPC69811
0.5644	Remote Similarity	NPC68419
0.5644	Remote Similarity	NPC604133
0.5625	Remote Similarity	NPC148417
0.56	Remote Similarity	NPC202828
0.56	Remote Similarity	NPC119592
0.5591	Remote Similarity	NPC220160
0.5586	Remote Similarity	NPC109588
0.5574	Remote Similarity	NPC4749
0.5574	Remote Similarity	NPC85154
0.5556	Remote Similarity	NPC162107
0.5556	Remote Similarity	NPC46912
0.5545	Remote Similarity	NPC263756
0.5545	Remote Similarity	NPC161674
0.5537	Remote Similarity	NPC100639
0.5487	Remote Similarity	NPC68175
0.5487	Remote Similarity	NPC470515
0.5481	Remote Similarity	NPC256798
0.5472	Remote Similarity	NPC189884
0.5472	Remote Similarity	NPC138334
0.547	Remote Similarity	NPC104137
0.547	Remote Similarity	NPC26626
0.5446	Remote Similarity	NPC104071
0.5421	Remote Similarity	NPC270667
0.5398	Remote Similarity	NPC102439
0.5398	Remote Similarity	NPC11551
0.5392	Remote Similarity	NPC606107
0.5377	Remote Similarity	NPC47063
0.5354	Remote Similarity	NPC191763
0.5354	Remote Similarity	NPC136768
0.5349	Remote Similarity	NPC224381
0.5347	Remote Similarity	NPC46388
0.5333	Remote Similarity	NPC76972
0.5333	Remote Similarity	NPC469782
0.5333	Remote Similarity	NPC204414
0.5328	Remote Similarity	NPC155410
0.5327	Remote Similarity	NPC473481
0.5327	Remote Similarity	NPC269095
0.5321	Remote Similarity	NPC203354
0.531	Remote Similarity	NPC124296
0.531	Remote Similarity	NPC114304
0.5306	Remote Similarity	NPC469778
0.5304	Remote Similarity	NPC31193
0.5303	Remote Similarity	NPC480422
0.5299	Remote Similarity	NPC324875
0.5299	Remote Similarity	NPC292677
0.5289	Remote Similarity	NPC123522
0.5285	Remote Similarity	NPC283417
0.5285	Remote Similarity	NPC200049
0.5268	Remote Similarity	NPC76497
0.5263	Remote Similarity	NPC488526
0.5254	Remote Similarity	NPC481030
0.5254	Remote Similarity	NPC470477
0.5243	Remote Similarity	NPC37739
0.5241	Remote Similarity	NPC469776
0.5238	Remote Similarity	NPC32723
0.5238	Remote Similarity	NPC110633
0.5234	Remote Similarity	NPC135849
0.5229	Remote Similarity	NPC475208
0.5217	Remote Similarity	NPC162574
0.5203	Remote Similarity	NPC481323
0.5192	Remote Similarity	NPC137917
0.5179	Remote Similarity	NPC470512
0.5175	Remote Similarity	NPC30289
0.5163	Remote Similarity	NPC295941
0.5149	Remote Similarity	NPC33012
0.5143	Remote Similarity	NPC31839
0.5135	Remote Similarity	NPC108748
0.5133	Remote Similarity	NPC135334
0.5133	Remote Similarity	NPC471547
0.5133	Remote Similarity	NPC475171
0.513	Remote Similarity	NPC305267
0.5126	Remote Similarity	NPC96641
0.5126	Remote Similarity	NPC163183
0.5126	Remote Similarity	NPC470516
0.5122	Remote Similarity	NPC470911
0.5118	Remote Similarity	NPC286457
0.5109	Remote Similarity	NPC246708
0.5099	Remote Similarity	NPC481324
0.5093	Remote Similarity	NPC480951
0.5093	Remote Similarity	NPC161434
0.5083	Remote Similarity	NPC475486
0.5083	Remote Similarity	NPC36831
0.5075	Remote Similarity	NPC8524
0.5049	Remote Similarity	NPC605954
0.5048	Remote Similarity	NPC310014
0.5048	Remote Similarity	NPC269315

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC171544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7417
0.1-0.2	1670
0.2-0.3	58
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data