NPASS Compound

Natural Product: NPC329923

Natural Product ID	NPC329923
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Symplocososide R
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-[(2Z)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(2-methylbutanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	symplocososide R
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL453785
PubChem CID	16099388
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 166172 0 0 0 0 0 0 0 0999 V2000 -11.0128 -2.6730 -1.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6606 -2.3946 -0.8667 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1805 -0.9929 -1.1909 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2265 -0.0273 -0.6132 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9096 -0.6698 -0.5656 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8326 0.3089 0.2679 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6855 -1.3122 -0.7563 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5417 -0.9087 -0.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2804 -1.9705 1.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1146 -3.3133 0.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 -3.2223 -0.8905 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4683 -1.9810 -0.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2771 -0.7176 -0.9526 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4792 0.3859 -0.3202 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0682 0.0573 0.0915 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3205 -0.6978 -0.9136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1281 -1.9353 -1.3606 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4906 -2.7778 -2.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0919 -2.6015 -2.6634 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6470 -1.5733 -1.8943 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0237 -1.3652 -0.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8096 -0.6700 0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1030 -1.3749 0.6092 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7512 -1.9859 -0.5740 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1522 -1.6272 -1.8867 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7365 -0.3087 -2.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3967 0.5409 -1.3892 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4427 -0.1319 -0.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2413 -1.6299 -0.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7079 -2.1054 0.8762 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0837 -2.3904 -1.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6912 0.2782 -0.9823 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4607 0.8320 0.0105 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9142 0.5656 -0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5690 0.9040 1.2050 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2807 2.3445 1.5465 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8630 2.7747 1.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3857 2.2709 0.0081 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9760 2.6675 2.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7455 2.2689 2.2817 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3781 3.0006 3.6270 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5966 2.6614 2.8550 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9438 0.7012 1.1828 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4996 1.5345 -1.0045 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1798 1.0309 -2.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 1.5660 -3.3224 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3227 2.7644 -3.8685 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8424 3.4978 -2.6641 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8578 2.6259 -1.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5532 1.2881 -2.0448 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2671 2.8599 -2.4232 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4623 2.5051 -3.7397 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3779 4.7443 -2.9485 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4184 3.5769 -4.5410 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2292 2.0376 -3.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 -2.6355 -2.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3098 -2.7308 0.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1085 0.2561 -2.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0164 -0.3831 1.3950 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6507 1.6325 -0.9187 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 -0.4834 -2.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9245 -0.2807 -3.3439 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4192 -4.0223 0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3715 -4.1860 1.4447 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4994 -1.8422 1.7791 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4056 -1.0092 2.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2892 -0.5099 3.1575 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5237 -0.7598 3.8052 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5492 0.0084 4.8567 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8231 0.1617 5.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3791 0.7704 5.3047 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6618 2.2712 5.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5080 3.0870 5.6898 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9363 3.9367 4.8454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7766 4.7993 5.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4972 4.0364 3.4583 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8482 -2.3107 -0.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0684 -2.3313 -2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1242 -3.7900 -1.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9718 -3.1644 -1.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7121 -2.4788 0.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 3.4451 -0.4692 -3.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 1.3472 -1.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6663 1.1320 -0.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3510 0.2609 0.4775 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4024 -3.1483 1.0885 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4799 -1.3965 1.6964 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8478 -2.1359 0.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4306 -1.7533 -2.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0675 -2.7137 -1.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6541 -3.3657 -1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0517 0.5974 0.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1841 -0.4237 -0.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1031 0.2555 1.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9585 2.9667 0.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9457 3.9116 0.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0141 2.3606 4.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9396 1.9288 3.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3958 1.5315 0.9549 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0955 -0.0692 -2.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4495 0.8453 -4.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1205 2.4135 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0 0 0 0 0 -5.6239 0.3146 -2.3050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8473 0.7190 -3.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7563 -3.9684 -0.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2068 -3.5780 0.8314 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3923 -5.0990 0.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7656 -3.5137 2.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7678 -4.9708 0.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1149 -4.6522 2.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4690 -1.2823 3.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6940 -0.1024 6.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1888 1.1975 5.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5795 -0.5182 5.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4290 0.5877 4.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2310 0.4766 6.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9969 2.6002 4.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5059 2.4472 5.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0965 3.0267 6.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1307 5.8240 5.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1581 4.3228 5.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1599 4.9147 4.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8930 4.7165 2.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4639 3.0027 3.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5244 4.3962 3.4156 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 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 51 52 1 0 48 53 1 0 47 54 1 0 46 55 1 0 25 56 1 0 21 57 1 0 16 58 1 0 15 59 1 0 14 60 1 0 13 61 1 0 61 62 1 0 10 63 1 0 10 64 1 0 9 65 1 0 65 66 1 0 66 67 2 0 66 68 1 0 68 69 2 3 69 70 1 0 69 71 1 0 71 72 1 0 72 73 1 0 73 74 2 3 74 75 1 0 74 76 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 77 1 0 1 78 1 0 1 79 1 0 2 80 1 0 2 81 1 0 3 82 1 0 4 83 1 0 4 84 1 0 4 85 1 0 8 86 1 0 9 87 1 0 11 88 1 0 11 89 1 0 12 90 1 0 14 91 1 0 15 92 1 0 18 93 1 0 19 94 1 0 19 95 1 0 20 96 1 0 22 97 1 0 22 98 1 0 23 99 1 0 23100 1 0 24101 1 0 26102 1 0 26103 1 0 27104 1 0 27105 1 0 28106 1 0 30107 1 0 30108 1 0 30109 1 0 31110 1 0 31111 1 0 31112 1 0 33113 1 0 34114 1 0 35115 1 0 36116 1 0 37117 1 0 41118 1 0 42119 1 0 43120 1 0 45121 1 0 46122 1 0 47123 1 0 48124 1 0 49125 1 0 51126 1 0 51127 1 0 52128 1 0 53129 1 0 54130 1 0 55131 1 0 56132 1 0 56133 1 0 56134 1 0 57135 1 0 57136 1 0 57137 1 0 58138 1 0 58139 1 0 58140 1 0 59141 1 0 60142 1 0 61143 1 0 61144 1 0 62145 1 0 63146 1 0 63147 1 0 63148 1 0 64149 1 0 64150 1 0 64151 1 0 68152 1 0 70153 1 0 70154 1 0 70155 1 0 71156 1 0 71157 1 0 72158 1 0 72159 1 0 73160 1 0 75161 1 0 75162 1 0 75163 1 0 76164 1 0 76165 1 0 76166 1 0 M END

Standard InCHIKey	ORGUHEZYVWCXQM-PDIAMSGGSA-N
Standard InCHI	InChI=1S/C57H90O19/c1-13-29(5)49(70)76-47-46(73-36(60)23-28(4)16-14-15-27(2)3)52(6,7)24-31-30-17-18-34-54(10)21-20-35(53(8,9)33(54)19-22-55(34,11)56(30,12)44(66)45(67)57(31,47)26-59)72-51-43(40(64)39(63)42(74-51)48(68)69)75-50-41(65)38(62)37(61)32(25-58)71-50/h15,17,23,29,31-35,37-47,50-51,58-59,61-67H,13-14,16,18-22,24-26H2,1-12H3,(H,68,69)/b28-23-/t29?,31-,32+,33-,34+,35-,37+,38-,39-,40-,41+,42-,43+,44-,45+,46-,47-,50-,51+,54-,55+,56-,57-/m0/s1
SMILES	CCC(C)C(=O)OC1C(C(CC2C1(C(C(C3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C)O)O)CO)(C)C)OC(=O)C=C(C)CCC=C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1078.61	Volume:	1085.728 ? Van der Waals volume.
Dense:	0.993	LogP:	4.403 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.565 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.295 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	43.0
TPSA:	308.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.798	Fsp³:	0.842
MCE-18:	164.571 ? 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:	0.272	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.384 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.174	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.234	MDCK Permeability:	-5.106
Pgp-inhibitor:	0.0	Pgp-substrate:	0.901
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):	0.992
20% Bioavailability (F20%):	0.513	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	64.778%	Volume Distribution (VD):	-0.473
Fu:	20.929% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.065	BCRP inhibitor:	0.0
BSEP inhibitor:	0.105

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.261	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.04
HLM stability:	0.002 ? 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):

-0.177

Half-life (T1/2):

3.726

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.095
Human Hepatotoxicity (H-HT):	0.314	Drug-induced Liver Injury (DILI):	0.138
AMES Toxicity:	0.017	Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.388	Skin Sensitization:	0.137
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.201	Ototoxicity:	1.0
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.075
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.021	Hek293 Cytotoxicity:	0.338
BCF:	0.897 ? 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:	4.763 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.871 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.273 ? 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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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	5

Activity Type	# Activity
Cell line	5

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	4400.0	nM	DrugMatrix in vivo data: Biochemistry
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	4100.0	nM	PMID[24904961]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[19188388]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT179	Cell line	A2780	Homo sapiens	IC50	=	1900.0	nM	PMID[19721073]

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 NPC329923 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	21599
0.1-0.2	24052
0.2-0.3	3232
0.3-0.4	609
0.4-0.5	277
0.5-0.6	51
0.6-0.7	22
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475281
0.8051	Intermediate Similarity	NPC475377
0.8051	Intermediate Similarity	NPC329657
0.8051	Intermediate Similarity	NPC476074
0.8	Intermediate Similarity	NPC477078
0.7583	Intermediate Similarity	NPC262796
0.7583	Intermediate Similarity	NPC45346
0.7563	Intermediate Similarity	NPC134914
0.7479	Intermediate Similarity	NPC475167
0.7438	Intermediate Similarity	NPC329993
0.7368	Intermediate Similarity	NPC477077
0.7258	Intermediate Similarity	NPC173435
0.7258	Intermediate Similarity	NPC172374
0.7258	Intermediate Similarity	NPC478064
0.6983	Remote Similarity	NPC477075
0.687	Remote Similarity	NPC150893
0.6774	Remote Similarity	NPC192765
0.6723	Remote Similarity	NPC329976
0.672	Remote Similarity	NPC178264
0.6694	Remote Similarity	NPC46823
0.6613	Remote Similarity	NPC264566
0.6562	Remote Similarity	NPC484833
0.6555	Remote Similarity	NPC477076
0.6471	Remote Similarity	NPC470914
0.6364	Remote Similarity	NPC295408
0.6364	Remote Similarity	NPC488309
0.6364	Remote Similarity	NPC329960
0.6303	Remote Similarity	NPC470913
0.6231	Remote Similarity	NPC475513
0.6202	Remote Similarity	NPC470518
0.6202	Remote Similarity	NPC473755
0.6172	Remote Similarity	NPC470912
0.6129	Remote Similarity	NPC606553
0.6	Remote Similarity	NPC301639
0.6	Remote Similarity	NPC71391
0.6	Remote Similarity	NPC478065
0.5985	Remote Similarity	NPC69425
0.5923	Remote Similarity	NPC277212
0.5923	Remote Similarity	NPC30279
0.5909	Remote Similarity	NPC488308
0.5865	Remote Similarity	NPC225791
0.5865	Remote Similarity	NPC312650
0.5798	Remote Similarity	NPC472949
0.576	Remote Similarity	NPC477079
0.5758	Remote Similarity	NPC82380
0.5758	Remote Similarity	NPC244296
0.5748	Remote Similarity	NPC605294
0.5746	Remote Similarity	NPC271610
0.5738	Remote Similarity	NPC251768
0.5726	Remote Similarity	NPC64715
0.5714	Remote Similarity	NPC478598
0.5703	Remote Similarity	NPC25998
0.5649	Remote Similarity	NPC478150
0.5625	Remote Similarity	NPC473586
0.5606	Remote Similarity	NPC602995
0.5581	Remote Similarity	NPC478152
0.5581	Remote Similarity	NPC478151
0.5564	Remote Similarity	NPC473918
0.5537	Remote Similarity	NPC603026
0.5407	Remote Similarity	NPC329828
0.5391	Remote Similarity	NPC301449
0.5391	Remote Similarity	NPC601290
0.5344	Remote Similarity	NPC107536
0.5344	Remote Similarity	NPC280029
0.5344	Remote Similarity	NPC9470
0.5328	Remote Similarity	NPC476780
0.5324	Remote Similarity	NPC110700
0.5308	Remote Similarity	NPC609281
0.5263	Remote Similarity	NPC478600
0.5263	Remote Similarity	NPC478599
0.5225	Remote Similarity	NPC476132
0.5217	Remote Similarity	NPC265841
0.5214	Remote Similarity	NPC476777
0.5154	Remote Similarity	NPC482737
0.5152	Remote Similarity	NPC477197
0.5143	Remote Similarity	NPC484059
0.5143	Remote Similarity	NPC484060
0.5122	Remote Similarity	NPC309780
0.5105	Remote Similarity	NPC484063
0.5105	Remote Similarity	NPC484064
0.5079	Remote Similarity	NPC192791
0.5079	Remote Similarity	NPC478066
0.5078	Remote Similarity	NPC118440
0.5075	Remote Similarity	NPC609119
0.5071	Remote Similarity	NPC258617
0.5036	Remote Similarity	NPC484061
0.5036	Remote Similarity	NPC484062

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6982
0.1-0.2	2108
0.2-0.3	56
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