NPASS Compound

Natural Product: NPC477076

Natural Product ID	NPC477076
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)-7,8,10-trihydroxy-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)-7,8,10-trihydroxy-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	44583928
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 138144 0 0 0 0 0 0 0 0999 V2000 7.5993 3.2305 -0.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0005 2.9097 -1.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5465 1.7731 -0.7641 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0108 1.5496 -1.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8432 0.6936 -0.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4373 -0.3576 0.2561 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5163 0.6927 0.2138 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8439 -0.3533 0.8776 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4344 0.0358 2.2660 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5229 -0.8617 2.9771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4642 -1.5159 2.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6960 -1.7324 0.7451 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8746 -1.1214 0.0603 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4442 -0.3478 -1.1888 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3205 0.5935 -1.0240 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0779 -0.0233 -0.3922 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5092 -1.3891 -0.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8576 -2.3986 -0.6085 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6548 -2.3058 -1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9524 -1.0753 -0.9370 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8252 0.0757 -1.2613 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0677 1.3364 -0.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3662 1.3452 -1.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0243 0.2322 -0.7486 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5045 -1.0437 -1.2748 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1561 -2.1836 -0.5336 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3563 -1.9705 0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0875 -0.6691 0.2469 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5074 0.3775 -0.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2101 0.5209 -1.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7009 1.7250 0.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4123 -0.9249 -0.0463 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2673 -0.8070 0.9741 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4024 0.1138 0.7956 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8849 0.5742 2.2073 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1583 -0.7077 2.9557 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0660 -1.7240 2.8517 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7278 -2.0360 1.5288 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4277 -2.9316 3.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4137 -4.0678 3.1084 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7928 -2.7927 4.9447 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3676 -0.3751 4.2814 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0857 1.2287 1.9915 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2681 1.1257 -0.0801 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3459 1.2360 -0.9729 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8645 0.9215 -2.3625 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0975 0.8728 -3.2526 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0627 1.9757 -3.0204 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0098 2.6387 -1.6872 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8307 2.5382 -1.0065 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2032 2.2759 -0.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0078 2.9313 -4.0481 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7035 -0.3681 -3.0393 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2973 -0.3555 -2.3864 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7851 -1.2915 -2.7361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2269 0.1554 -2.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8683 0.8670 0.7984 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7880 1.7193 -0.3397 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5661 0.2838 -1.6731 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7051 -2.2506 -0.6288 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3021 -3.0654 0.2977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3233 -1.9450 3.7374 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8398 -0.1063 4.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5866 0.1998 3.0821 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2190 2.9689 0.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5335 4.3692 -0.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9003 2.9578 -1.7138 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6650 3.6203 -1.6541 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5608 2.3239 -0.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3039 0.5133 -0.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1696 1.7027 -2.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7101 -1.0678 1.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0246 1.0601 2.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4767 -1.0137 2.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2528 -2.5088 2.7142 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8827 -2.8546 0.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1368 -1.0768 -1.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0371 0.9714 -2.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1657 -3.4572 -0.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9344 -2.1548 -2.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0235 -3.2004 -1.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9712 -1.1843 0.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5338 2.2510 -1.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 1.3165 0.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4537 1.3779 -2.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7705 2.3336 -1.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6470 0.2864 0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3664 -2.6718 0.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4423 -3.0129 -1.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0846 -2.1895 1.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1186 -2.8102 0.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1040 -0.3172 1.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6124 1.1137 -2.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 -0.4245 -2.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0949 1.1633 -1.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7915 2.0416 0.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4918 1.6233 0.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0238 2.5134 -0.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6468 -0.4092 1.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3230 -0.4836 0.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1697 1.2436 2.6532 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1275 -1.1183 2.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1649 -1.2731 3.3684 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4905 -3.4087 5.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2033 -0.7666 4.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7864 0.8424 2.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1346 0.4795 -0.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1763 1.6889 -2.7498 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7552 0.9534 -4.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1045 1.5402 -3.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1540 3.7522 -1.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5854 1.2730 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0229 3.0456 -0.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8619 2.3480 0.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4931 3.7225 -3.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3123 -0.3461 -2.2752 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0644 -0.9952 -2.2554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9382 -0.4131 -3.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 -2.0318 -3.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7519 -1.8755 -2.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3361 1.2209 -2.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4028 -0.1673 -3.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0800 -0.4395 -3.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8474 1.0652 1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0836 0.6481 1.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6985 1.8756 0.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6828 2.5608 -0.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5109 0.5456 -2.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0188 -2.8637 -1.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4196 -1.7086 -1.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4155 -3.9650 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7487 -2.6499 2.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1179 -1.4376 4.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6706 -2.4766 4.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0953 0.6291 3.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5793 0.4587 4.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2622 -0.7751 4.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2405 -0.5032 2.8845 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 13 60 1 6 60 61 1 0 10 62 1 0 10 63 1 0 9 64 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 65 1 0 1 66 1 0 1 67 1 0 2 68 1 0 4 69 1 0 4 70 1 0 4 71 1 0 8 72 1 1 9 73 1 6 11 74 1 0 11 75 1 0 12 76 1 1 14 77 1 6 15 78 1 6 18 79 1 0 19 80 1 0 19 81 1 0 20 82 1 1 22 83 1 0 22 84 1 0 23 85 1 0 23 86 1 0 24 87 1 1 26 88 1 0 26 89 1 0 27 90 1 0 27 91 1 0 28 92 1 1 30 93 1 0 30 94 1 0 30 95 1 0 31 96 1 0 31 97 1 0 31 98 1 0 33 99 1 1 34100 1 6 35101 1 1 36102 1 6 37103 1 1 41104 1 0 42105 1 0 43106 1 0 45107 1 1 46108 1 6 47109 1 6 48110 1 1 49111 1 6 51112 1 0 51113 1 0 51114 1 0 52115 1 0 53116 1 0 54117 1 0 55118 1 0 55119 1 0 55120 1 0 56121 1 0 56122 1 0 56123 1 0 57124 1 0 57125 1 0 57126 1 0 58127 1 0 59128 1 0 60129 1 0 60130 1 0 61131 1 0 62132 1 0 62133 1 0 62134 1 0 63135 1 0 63136 1 0 63137 1 0 64138 1 0 M END

Standard InCHIKey	XXVNQOOHCDAFKO-YTINUVENSA-N
Standard InCHI	InChI=1S/C47H74O17/c1-11-20(2)39(59)64-37-36(56)42(4,5)18-23-22-12-13-25-44(8)16-15-26(43(6,7)24(44)14-17-45(25,9)46(22,10)34(54)35(55)47(23,37)19-48)61-41-33(30(52)29(51)32(62-41)38(57)58)63-40-31(53)28(50)27(49)21(3)60-40/h11-12,21,23-37,40-41,48-56H,13-19H2,1-10H3,(H,57,58)/b20-11-/t21-,23+,24+,25-,26+,27-,28+,29+,30+,31+,32+,33-,34+,35-,36+,37+,40-,41-,44+,45-,46+,47+/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)O)CO)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	910.49	Volume:	900.461 ? Van der Waals volume.
Dense:	1.011	LogP:	2.682 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.919 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.538 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	41.0
TPSA:	282.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.432	Fsp³:	0.872
MCE-18:	163.591 ? 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:	0.763	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.2	Promiscuous compounds:	0.24

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.957	MDCK Permeability:	-5.269
Pgp-inhibitor:	0.0	Pgp-substrate:	0.968
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):	0.886
20% Bioavailability (F20%):	0.801	30% Bioavailability (F30%):	0.921
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.958
Plasma Protein Binding (PPB):	70.814%	Volume Distribution (VD):	-0.444
Fu:	18.272% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.765	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.045
HLM stability:	0.039 ? 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):

-0.02

Half-life (T1/2):

4.165

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.273	Drug-induced Liver Injury (DILI):	0.732
AMES Toxicity:	0.365	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.084	Skin Sensitization:	0.973
Carcinogencity:	0.055	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.05
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.271	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.62	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.04	Hek293 Cytotoxicity:	0.06
BCF:	0.462 ? 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:	3.363 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.043 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.954 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	roots	Balkesir-Edremit, Turkey	2003-AUG	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31311207]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	1
Others	1

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	40	ug/ml	PMID[16872157]
NPT2	Others	Unspecified	n.a.	IC50	=	40	ug/ml	PMID[16872157]

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC477076 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	21920
0.1-0.2	23818
0.2-0.3	3149
0.3-0.4	568
0.4-0.5	296
0.5-0.6	78
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC477079
0.8515	High Similarity	NPC477077
0.7885	Intermediate Similarity	NPC477075
0.781	Intermediate Similarity	NPC477078
0.7193	Intermediate Similarity	NPC277212
0.7193	Intermediate Similarity	NPC30279
0.7043	Intermediate Similarity	NPC46823
0.6752	Remote Similarity	NPC473918
0.6695	Remote Similarity	NPC71391
0.6555	Remote Similarity	NPC329923
0.6555	Remote Similarity	NPC475281
0.6555	Remote Similarity	NPC192765
0.65	Remote Similarity	NPC178264
0.6491	Remote Similarity	NPC329976
0.6435	Remote Similarity	NPC605294
0.629	Remote Similarity	NPC329657
0.626	Remote Similarity	NPC225791
0.621	Remote Similarity	NPC484059
0.621	Remote Similarity	NPC484060
0.6098	Remote Similarity	NPC470518
0.6098	Remote Similarity	NPC484061
0.6098	Remote Similarity	NPC484062
0.6087	Remote Similarity	NPC470914
0.6053	Remote Similarity	NPC470913
0.6	Remote Similarity	NPC478600
0.6	Remote Similarity	NPC478599
0.5827	Remote Similarity	NPC484833
0.5804	Remote Similarity	NPC603026
0.5794	Remote Similarity	NPC265841
0.5758	Remote Similarity	NPC88349
0.5739	Remote Similarity	NPC251768
0.5726	Remote Similarity	NPC64715
0.5714	Remote Similarity	NPC478598
0.568	Remote Similarity	NPC47995
0.5664	Remote Similarity	NPC472949
0.5656	Remote Similarity	NPC609119
0.5641	Remote Similarity	NPC131469
0.5635	Remote Similarity	NPC82380
0.5635	Remote Similarity	NPC244296
0.5625	Remote Similarity	NPC271610
0.56	Remote Similarity	NPC269484
0.56	Remote Similarity	NPC97918
0.5593	Remote Similarity	NPC95437
0.5583	Remote Similarity	NPC187618
0.5574	Remote Similarity	NPC25998
0.5546	Remote Similarity	NPC114692
0.55	Remote Similarity	NPC218954
0.5492	Remote Similarity	NPC470915
0.5476	Remote Similarity	NPC264566
0.5476	Remote Similarity	NPC602995
0.5455	Remote Similarity	NPC120116
0.5417	Remote Similarity	NPC236657
0.5414	Remote Similarity	NPC484063
0.5414	Remote Similarity	NPC484064
0.541	Remote Similarity	NPC609281
0.5403	Remote Similarity	NPC313110
0.5385	Remote Similarity	NPC258617
0.5379	Remote Similarity	NPC11577
0.5379	Remote Similarity	NPC141600
0.5372	Remote Similarity	NPC301449
0.5372	Remote Similarity	NPC601290
0.5366	Remote Similarity	NPC477197
0.5366	Remote Similarity	NPC606553
0.5351	Remote Similarity	NPC309780
0.5323	Remote Similarity	NPC472267
0.5323	Remote Similarity	NPC115656
0.5323	Remote Similarity	NPC478152
0.5323	Remote Similarity	NPC478151
0.5308	Remote Similarity	NPC476774
0.5294	Remote Similarity	NPC482722
0.5294	Remote Similarity	NPC471963
0.5271	Remote Similarity	NPC329828
0.5267	Remote Similarity	NPC262796
0.5267	Remote Similarity	NPC45346
0.5246	Remote Similarity	NPC482735
0.5227	Remote Similarity	NPC476779
0.52	Remote Similarity	NPC107536
0.52	Remote Similarity	NPC280029
0.52	Remote Similarity	NPC9470
0.5197	Remote Similarity	NPC470911
0.5191	Remote Similarity	NPC488308
0.5191	Remote Similarity	NPC476780
0.5188	Remote Similarity	NPC475377
0.5188	Remote Similarity	NPC476074
0.5169	Remote Similarity	NPC478066
0.5164	Remote Similarity	NPC482740
0.5156	Remote Similarity	NPC478150
0.5152	Remote Similarity	NPC312650
0.5111	Remote Similarity	NPC476775
0.5086	Remote Similarity	NPC25605
0.5086	Remote Similarity	NPC56713
0.5081	Remote Similarity	NPC477193
0.5077	Remote Similarity	NPC252289
0.5077	Remote Similarity	NPC305793
0.5075	Remote Similarity	NPC476777
0.5043	Remote Similarity	NPC482748
0.5042	Remote Similarity	NPC192791
0.5041	Remote Similarity	NPC118440
0.5039	Remote Similarity	NPC482736
0.5039	Remote Similarity	NPC252657
0.5039	Remote Similarity	NPC88311
0.5039	Remote Similarity	NPC482738
0.5039	Remote Similarity	NPC610461
0.5038	Remote Similarity	NPC478597

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6901
0.1-0.2	2202
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