NPASS Compound

Natural Product: NPC22956

Natural Product ID	NPC22956
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Calendulagycoside B
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500221
PubChem CID	44566499
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 143150 0 0 0 0 0 0 0 0999 V2000 -2.2169 -3.1634 3.3425 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9705 -4.2322 2.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0712 -3.7268 1.9681 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6171 -3.0343 0.8581 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5767 -2.1157 0.4859 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3955 -1.5411 -0.7499 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 -0.1589 -0.7372 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0766 0.3082 -1.4639 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3780 1.2931 -2.4240 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2805 0.9402 -3.3618 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3720 0.0325 -2.8614 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5645 0.3557 -1.3965 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7155 1.7151 -1.2548 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8442 2.0843 -0.5641 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7304 2.8492 -1.3272 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0060 2.7856 -0.7930 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8612 3.7783 -1.5517 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1748 3.7908 -1.0849 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1066 3.0260 0.6543 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8501 3.0403 1.4368 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5764 2.9027 0.6782 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5960 2.3311 1.4797 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7353 4.2323 2.1954 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8143 4.2241 0.9165 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8825 -1.2891 -2.8939 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8957 2.0652 -4.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7565 1.7462 -4.9838 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6405 3.3913 -3.9141 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0446 0.8217 -0.6953 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8367 0.1872 -1.0414 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0018 1.2753 -1.6678 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4665 1.0559 -1.6226 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9521 0.7126 -0.2051 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2343 -0.5195 0.2010 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2711 -0.4698 0.1527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6813 -1.9569 0.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 0.0139 1.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7272 -1.1165 1.4930 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1811 -1.1404 1.6815 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0331 -0.2368 0.8614 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3971 0.2824 -0.3950 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2206 1.2693 -1.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6518 1.1984 -0.7706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1999 0.1998 -0.0714 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3310 -0.9305 0.4012 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0343 -1.8944 -0.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9783 -1.7097 1.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4216 -2.0104 1.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2228 -0.7690 1.0203 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6378 0.2984 0.1814 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4322 0.4048 -1.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7826 0.9885 -0.7547 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6249 1.2333 -1.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6720 2.2863 0.0010 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4526 -0.0110 0.1726 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5869 -1.1954 0.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5311 -0.2783 2.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1914 0.8225 2.8525 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2603 -1.1672 3.2145 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4917 0.9025 1.7680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7573 1.9015 0.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9523 -2.7866 0.4519 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8139 -4.3021 0.3643 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0108 -4.8221 1.5455 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8970 -5.1284 2.5985 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2262 -4.6578 -0.8426 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6979 -2.4952 1.5805 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7023 -2.3022 3.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3149 -4.9759 2.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4415 -4.7110 3.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6501 -2.9821 2.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5866 -1.3010 1.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 0.2298 0.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6614 -0.5157 -2.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7316 0.3434 -4.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3098 0.1203 -3.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3972 -0.1658 -0.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3744 1.1336 -0.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3996 1.7656 -1.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4017 4.7805 -1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8057 3.5366 -2.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4942 2.8724 -0.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7767 2.2262 1.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8355 2.2301 2.2269 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2796 3.9422 0.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1404 2.9854 2.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4471 4.9617 1.5848 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3227 5.0151 0.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5892 -1.5099 -3.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3825 4.0857 -3.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0089 -0.5795 -1.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3007 2.2922 -1.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2957 1.3341 -2.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7064 0.2041 -2.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9685 1.9562 -1.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5102 -1.2817 -0.5949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9655 -2.3598 1.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1446 -2.5521 -0.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5402 -2.0523 -0.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9169 0.3549 1.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2934 0.7730 1.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0329 -0.8246 2.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2991 -2.1393 1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2480 -0.5152 2.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3973 -1.0018 2.7836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -2.1951 1.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2968 -0.6322 -1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1716 1.0491 -2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8870 2.3296 -1.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2643 2.0416 -1.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0817 -2.4409 -0.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0646 -1.3881 -1.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8183 -2.6787 -0.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9634 -1.2119 2.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4939 -2.7309 1.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8236 -2.5677 2.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5432 -2.6725 0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8253 1.2816 0.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9440 1.1046 -1.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5855 -0.5538 -1.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2676 2.1238 -2.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6754 0.3198 -2.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6554 1.4549 -1.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7547 2.8503 -0.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5226 2.9626 -0.3088 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8522 2.1426 1.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7794 0.4514 1.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3603 -0.3693 -0.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4849 -1.9064 -0.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0793 -1.7612 1.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2248 -1.0880 4.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8998 0.9139 2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4787 1.8757 1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5467 0.7475 2.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7460 2.3153 0.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4524 2.6983 0.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9033 1.7615 1.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5293 -2.4892 -0.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8409 -4.7060 0.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4743 -5.7633 1.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8089 -5.2701 2.2709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7416 -5.4225 -1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3777 -1.8368 1.3567 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 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 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 19 24 1 0 11 25 1 0 10 26 1 0 26 27 2 0 26 28 1 0 8 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 1 0 35 36 1 0 35 37 1 0 34 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 1 6 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 52 55 1 0 55 56 1 0 49 57 1 1 57 58 2 0 57 59 1 0 40 60 1 1 33 61 1 1 5 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 62 67 1 0 64 3 1 0 12 7 1 0 21 14 1 0 35 30 1 0 45 40 1 0 56 49 1 0 41 33 1 0 50 44 1 0 1 68 1 0 2 69 1 0 2 70 1 0 3 71 1 1 5 72 1 1 7 73 1 1 8 74 1 6 10 75 1 6 11 76 1 6 12 77 1 1 14 78 1 1 16 79 1 1 17 80 1 0 17 81 1 0 18 82 1 0 19 83 1 1 20 84 1 1 21 85 1 6 22 86 1 0 23 87 1 0 24 88 1 0 25 89 1 0 28 90 1 0 30 91 1 6 31 92 1 0 31 93 1 0 32 94 1 0 32 95 1 0 34 96 1 6 36 97 1 0 36 98 1 0 36 99 1 0 37100 1 0 37101 1 0 37102 1 0 38103 1 0 38104 1 0 39105 1 0 39106 1 0 41107 1 6 42108 1 0 42109 1 0 43110 1 0 46111 1 0 46112 1 0 46113 1 0 47114 1 0 47115 1 0 48116 1 0 48117 1 0 50118 1 1 51119 1 0 51120 1 0 53121 1 0 53122 1 0 53123 1 0 54124 1 0 54125 1 0 54126 1 0 55127 1 0 55128 1 0 56129 1 0 56130 1 0 59131 1 0 60132 1 0 60133 1 0 60134 1 0 61135 1 0 61136 1 0 61137 1 0 62138 1 6 63139 1 6 64140 1 6 65141 1 0 66142 1 0 67143 1 0 M END

Standard InCHIKey	YDZWHGJRWMQCDP-NKILCQAGSA-N
Standard InCHI	InChI=1S/C48H76O19/c1-43(2)14-16-48(42(60)61)17-15-46(6)21(22(48)18-43)8-9-26-45(5)12-11-27(44(3,4)25(45)10-13-47(26,46)7)64-41-37(67-40-33(56)31(54)29(52)24(20-50)63-40)35(34(57)36(66-41)38(58)59)65-39-32(55)30(53)28(51)23(19-49)62-39/h8,22-37,39-41,49-57H,9-20H2,1-7H3,(H,58,59)(H,60,61)/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31-,32+,33+,34-,35-,36-,37+,39-,40-,41+,45-,46+,47+,48-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)O)C(=O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	956.5	Volume:	929.417 ? Van der Waals volume.
Dense:	1.029	LogP:	1.192 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.081 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.325 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	46.0
TPSA:	312.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.107	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.293	Fsp³:	0.917
MCE-18:	176.696 ? 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:	0.877	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.25	Promiscuous compounds:	0.141

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.269	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
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):	0.916
20% Bioavailability (F20%):	0.553	30% Bioavailability (F30%):	0.897
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.982
Plasma Protein Binding (PPB):	74.463%	Volume Distribution (VD):	-0.559
Fu:	17.605% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.934	BCRP inhibitor:	0.0
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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.009
HLM stability:	0.005 ? 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):

-0.015

Half-life (T1/2):

3.055

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.863	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.889	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.232	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.861	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.791	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.462	Hek293 Cytotoxicity:	0.07
BCF:	0.504 ? 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:	3.346 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.834 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.842 ? 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
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	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
Activity	8
IC50	1
GI50	46
ID50	1

Activity Type	# Activity
Cell line	48
Organism	1
Others	5
Non-molecular	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	DOI[10.6019/CHEMBL1201861]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[25368960]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	>	100000.0	nM	PMID[24950030]
NPT111	Cell line	K562	Homo sapiens	GI50	=	81100.0	nM	DrugMatrix in vitro pharmacology data
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	=	86300.0	nM	PMID[24950030]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	=	50900.0	nM	PMID[24950030]
NPT81	Cell line	A549	Homo sapiens	GI50	>	100000.0	nM	PMID[25062006]
NPT394	Cell line	EKVX	Homo sapiens	GI50	>	100000.0	nM	PMID[25014747]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	>	100000.0	nM	PMID[25062006]
NPT372	Cell line	HOP-92	Homo sapiens	GI50	>	100000.0	nM	DrugMatrix in vitro pharmacology data
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	>	100000.0	nM	PMID[25059503]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	=	20200.0	nM	PMID[25059503]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	=	26000.0	nM	PMID[20801553]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	>	100000.0	nM	PMID[23871903]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	=	38400.0	nM	PMID[20801553]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	>	100000.0	nM	PMID[23747804]
NPT139	Cell line	HT-29	Homo sapiens	GI50	=	40900.0	nM	PMID[20801553]
NPT386	Cell line	KM12	Homo sapiens	GI50	>	100000.0	nM	PMID[20801553]
NPT323	Cell line	SW-620	Homo sapiens	GI50	>	100000.0	nM	PMID[18725443]
NPT395	Cell line	SF-268	Homo sapiens	GI50	>	100000.0	nM	PMID[18725443]
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	31000.0	nM	PMID[26005918]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	>	100000.0	nM	PMID[18327912]
NPT380	Cell line	U-251	Homo sapiens	GI50	=	32300.0	nM	PMID[12193037]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	=	79900.0	nM	PMID[24387625]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	>	100000.0	nM	PMID[21051535]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	>	100000.0	nM	PMID[24216090]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	>	100000.0	nM	PMID[19456120]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	=	23000.0	nM	PMID[25760525]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	>	100000.0	nM	PMID[23977995]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	>	100000.0	nM	PMID[23977995]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	>	100000.0	nM	PMID[26965857]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	>	100000.0	nM	PMID[26965857]
NPT401	Cell line	786-0	Homo sapiens	GI50	>	100000.0	nM	PMID[26965857]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	>	100000.0	nM	PMID[25710081]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	>	100000.0	nM	PMID[25710081]
NPT368	Cell line	SN12C	Homo sapiens	GI50	=	84000.0	nM	PMID[23977995]
NPT384	Cell line	TK-10	Homo sapiens	GI50	>	100000.0	nM	PMID[23977995]
NPT371	Cell line	UO-31	Homo sapiens	GI50	=	63500.0	nM	PMID[21970540]
NPT306	Cell line	PC-3	Homo sapiens	GI50	=	20600.0	nM	PMID[17253868]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	53500.0	nM	PMID[21970540]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	>	100000.0	nM	PMID[21970540]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	45000.0	nM	PMID[21288727]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	>	100000.0	nM	PMID[15165136]
NPT457	Cell line	BT-549	Homo sapiens	GI50	>	100000.0	nM	PMID[17253868]
NPT396	Cell line	T47D	Homo sapiens	GI50	>	100000.0	nM	PMID[21970540]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	=	94600.0	nM	PMID[21970540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	>	100000.0	nM	PMID[17190444]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	97400.0	nM	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Activity	=	5.1	%	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Activity	=	40.3	%	PMID[10411485]
NPT2	Others	Unspecified	n.a.	Activity	=	69.2	%	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	IC50	=	470.0	molar ratio	PMID[24689881]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[18644958]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.05	mg	PMID[3783593]

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 NPC22956 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	23331
0.1-0.2	22295
0.2-0.3	2892
0.3-0.4	744
0.4-0.5	384
0.5-0.6	124
0.6-0.7	52
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC109079
0.8172	Intermediate Similarity	NPC472949
0.814	Intermediate Similarity	NPC606107
0.7959	Intermediate Similarity	NPC79718
0.7872	Intermediate Similarity	NPC127056
0.7826	Intermediate Similarity	NPC164194
0.7573	Intermediate Similarity	NPC480939
0.7416	Intermediate Similarity	NPC204407
0.7404	Intermediate Similarity	NPC62725
0.7396	Intermediate Similarity	NPC25605
0.73	Intermediate Similarity	NPC44716
0.7228	Intermediate Similarity	NPC475591
0.7228	Intermediate Similarity	NPC236870
0.7216	Intermediate Similarity	NPC59804
0.72	Intermediate Similarity	NPC114304
0.7174	Intermediate Similarity	NPC286347
0.7143	Intermediate Similarity	NPC114441
0.7115	Intermediate Similarity	NPC324875
0.7115	Intermediate Similarity	NPC292677
0.7071	Intermediate Similarity	NPC488561
0.7048	Intermediate Similarity	NPC488564
0.7041	Intermediate Similarity	NPC56713
0.703	Intermediate Similarity	NPC605226
0.699	Remote Similarity	NPC257468
0.6923	Remote Similarity	NPC302887
0.6909	Remote Similarity	NPC251263
0.69	Remote Similarity	NPC603026
0.6822	Remote Similarity	NPC187290
0.6809	Remote Similarity	NPC31839
0.6796	Remote Similarity	NPC180550
0.6796	Remote Similarity	NPC35405
0.6774	Remote Similarity	NPC283849
0.6768	Remote Similarity	NPC12288
0.6762	Remote Similarity	NPC119794
0.6735	Remote Similarity	NPC270667
0.6733	Remote Similarity	NPC6377
0.6733	Remote Similarity	NPC208381
0.6729	Remote Similarity	NPC160452
0.6701	Remote Similarity	NPC191410
0.6667	Remote Similarity	NPC80843
0.6636	Remote Similarity	NPC23275
0.6607	Remote Similarity	NPC219180
0.66	Remote Similarity	NPC136877
0.6542	Remote Similarity	NPC276093
0.6535	Remote Similarity	NPC174679
0.6535	Remote Similarity	NPC279554
0.6514	Remote Similarity	NPC469947
0.6514	Remote Similarity	NPC480948
0.6491	Remote Similarity	NPC54636
0.6476	Remote Similarity	NPC104400
0.6476	Remote Similarity	NPC10320
0.646	Remote Similarity	NPC166422
0.6415	Remote Similarity	NPC139044
0.6396	Remote Similarity	NPC25998
0.6372	Remote Similarity	NPC133818
0.6348	Remote Similarity	NPC47995
0.6339	Remote Similarity	NPC609119
0.63	Remote Similarity	NPC475472
0.6286	Remote Similarity	NPC469945
0.6263	Remote Similarity	NPC294112
0.625	Remote Similarity	NPC28198
0.625	Remote Similarity	NPC476123
0.6216	Remote Similarity	NPC329976
0.6204	Remote Similarity	NPC481082
0.6204	Remote Similarity	NPC164419
0.6182	Remote Similarity	NPC323359
0.6161	Remote Similarity	NPC605294
0.6121	Remote Similarity	NPC283417
0.6121	Remote Similarity	NPC200049
0.6121	Remote Similarity	NPC602995
0.6083	Remote Similarity	NPC161717
0.6071	Remote Similarity	NPC475486
0.6055	Remote Similarity	NPC73829
0.6017	Remote Similarity	NPC181066
0.6017	Remote Similarity	NPC329828
0.5966	Remote Similarity	NPC484061
0.5966	Remote Similarity	NPC484062
0.5965	Remote Similarity	NPC288205
0.5965	Remote Similarity	NPC51465
0.5948	Remote Similarity	NPC323341
0.5932	Remote Similarity	NPC473918
0.5918	Remote Similarity	NPC57362
0.5917	Remote Similarity	NPC265841
0.5917	Remote Similarity	NPC488308
0.59	Remote Similarity	NPC100383
0.5888	Remote Similarity	NPC263756
0.5888	Remote Similarity	NPC213674
0.5877	Remote Similarity	NPC280941
0.5877	Remote Similarity	NPC235772
0.5872	Remote Similarity	NPC251768
0.5868	Remote Similarity	NPC312650
0.5854	Remote Similarity	NPC302543
0.5841	Remote Similarity	NPC488209
0.5833	Remote Similarity	NPC192791
0.5825	Remote Similarity	NPC480938
0.582	Remote Similarity	NPC471385
0.582	Remote Similarity	NPC484059
0.582	Remote Similarity	NPC484060
0.5818	Remote Similarity	NPC471383
0.5798	Remote Similarity	NPC277212
0.5798	Remote Similarity	NPC30279
0.576	Remote Similarity	NPC484063
0.576	Remote Similarity	NPC484064
0.576	Remote Similarity	NPC488309
0.575	Remote Similarity	NPC71391
0.5743	Remote Similarity	NPC242611
0.5738	Remote Similarity	NPC271610
0.5738	Remote Similarity	NPC225791
0.5727	Remote Similarity	NPC159309
0.5727	Remote Similarity	NPC86222
0.5714	Remote Similarity	NPC120840
0.5667	Remote Similarity	NPC46823
0.5648	Remote Similarity	NPC488516
0.5648	Remote Similarity	NPC157868
0.5631	Remote Similarity	NPC475633
0.5631	Remote Similarity	NPC284807
0.5631	Remote Similarity	NPC473538
0.562	Remote Similarity	NPC192765
0.5619	Remote Similarity	NPC76999
0.5614	Remote Similarity	NPC301449
0.5614	Remote Similarity	NPC601290
0.5575	Remote Similarity	NPC64715
0.5575	Remote Similarity	NPC488515
0.5574	Remote Similarity	NPC178264
0.5556	Remote Similarity	NPC470475
0.5546	Remote Similarity	NPC284449
0.5526	Remote Similarity	NPC281148
0.5526	Remote Similarity	NPC114484
0.5524	Remote Similarity	NPC473481
0.5495	Remote Similarity	NPC117714
0.5495	Remote Similarity	NPC30289
0.5487	Remote Similarity	NPC470478
0.5446	Remote Similarity	NPC40775
0.5446	Remote Similarity	NPC10607
0.5446	Remote Similarity	NPC46665
0.5446	Remote Similarity	NPC2370
0.5424	Remote Similarity	NPC476992
0.5417	Remote Similarity	NPC471384
0.5385	Remote Similarity	NPC480946
0.5385	Remote Similarity	NPC130577
0.5385	Remote Similarity	NPC142415
0.5385	Remote Similarity	NPC102683
0.5372	Remote Similarity	NPC470476
0.5345	Remote Similarity	NPC291903
0.5339	Remote Similarity	NPC480936
0.5326	Remote Similarity	NPC270768
0.5326	Remote Similarity	NPC59263
0.5326	Remote Similarity	NPC210106
0.5321	Remote Similarity	NPC309780
0.5321	Remote Similarity	NPC108748
0.5317	Remote Similarity	NPC476779
0.5299	Remote Similarity	NPC187618
0.5294	Remote Similarity	NPC475119
0.528	Remote Similarity	NPC476774
0.528	Remote Similarity	NPC476780
0.5276	Remote Similarity	NPC110700
0.5276	Remote Similarity	NPC111466
0.5268	Remote Similarity	NPC75417
0.5263	Remote Similarity	NPC118440
0.5238	Remote Similarity	NPC258617
0.5234	Remote Similarity	NPC475611
0.5225	Remote Similarity	NPC473884
0.5221	Remote Similarity	NPC480947
0.5214	Remote Similarity	NPC75318
0.521	Remote Similarity	NPC11242
0.5207	Remote Similarity	NPC478155
0.5207	Remote Similarity	NPC478154
0.52	Remote Similarity	NPC21691
0.5189	Remote Similarity	NPC480937
0.5182	Remote Similarity	NPC235405
0.5179	Remote Similarity	NPC161674
0.5175	Remote Similarity	NPC473383
0.5169	Remote Similarity	NPC80986
0.5161	Remote Similarity	NPC275809
0.5156	Remote Similarity	NPC476777
0.5135	Remote Similarity	NPC249848
0.5135	Remote Similarity	NPC107966
0.5133	Remote Similarity	NPC112352
0.5128	Remote Similarity	NPC114692
0.5124	Remote Similarity	NPC473824
0.512	Remote Similarity	NPC4749
0.512	Remote Similarity	NPC488211
0.5106	Remote Similarity	NPC231063
0.5106	Remote Similarity	NPC282395
0.5106	Remote Similarity	NPC158141
0.5106	Remote Similarity	NPC110308
0.5086	Remote Similarity	NPC131469
0.5081	Remote Similarity	NPC470218
0.5081	Remote Similarity	NPC264566
0.5077	Remote Similarity	NPC476775
0.5074	Remote Similarity	NPC475368
0.5053	Remote Similarity	NPC298554
0.5052	Remote Similarity	NPC296164
0.5049	Remote Similarity	NPC274507
0.5043	Remote Similarity	NPC95437
0.5042	Remote Similarity	NPC480474
0.5041	Remote Similarity	NPC478152
0.5041	Remote Similarity	NPC478151
0.5036	Remote Similarity	NPC40085

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6942
0.1-0.2	2137
0.2-0.3	62
0.3-0.4	7
0.4-0.5	2
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