NPASS Compound

Natural Product: NPC85154

Natural Product ID	NPC85154
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asterlingulatoside
IUPAC Name	[(2S,3R,4S,5S)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	asterlingulatoside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446062
PubChem CID	44566669
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 174183 0 0 0 0 0 0 0 0999 V2000 -11.3282 4.3924 -2.0834 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4924 4.0495 -1.4005 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4374 2.5772 -1.0518 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.3690 2.2418 -0.2547 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2373 0.8345 -0.3059 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9488 0.4690 0.0596 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2348 -0.0888 -0.9825 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1837 0.9313 -1.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2798 1.1502 -0.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5572 -0.1177 0.1929 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0753 -1.2359 -0.6810 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5596 -1.3791 -0.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1404 -2.0449 0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8719 -2.2983 -1.8986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3297 -2.5015 -0.4238 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8830 -2.2683 -0.8746 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2613 -1.1518 -0.1121 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1172 0.0823 -0.2140 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4803 1.2773 0.4116 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0520 1.0958 0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2612 0.1451 0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9276 -0.7579 -0.7776 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2018 0.0078 -2.0528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1347 -1.9635 -1.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6823 -1.7138 -1.3286 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0441 -0.7718 -0.3864 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8654 0.0159 0.5416 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1920 1.3064 0.9562 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1797 2.2279 -0.1466 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 2.9754 0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 3.3009 -0.3709 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3729 1.4833 -1.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9272 0.1045 -1.2082 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9157 -1.5968 0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2977 -2.6821 -0.0193 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3344 -1.1821 1.6780 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2212 -1.9164 2.4785 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4081 -2.4737 3.5256 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2128 -1.5531 4.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4992 -1.3849 5.3543 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6903 -1.6582 4.4194 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2979 -1.0655 3.0873 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3572 -0.9572 2.2117 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5695 0.3482 1.7758 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4132 0.3855 0.4086 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3455 -0.3611 -0.2673 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9933 -0.5544 -1.7234 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7064 0.1844 -0.0561 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9887 0.8312 1.2496 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8819 0.9318 2.2270 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6964 2.2681 2.6531 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4450 2.1478 0.9773 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6081 -0.8926 -0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4211 -0.6968 -1.3499 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2649 -1.7075 -2.2924 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3429 -2.5849 -2.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6025 -1.8965 -2.7921 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7615 -0.5555 -2.0651 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8649 -0.5947 -0.8579 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9251 0.6057 -0.1389 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0784 -0.4337 -1.6153 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6855 0.6996 -2.1360 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7696 0.3231 -2.9602 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5635 -0.5933 -2.2781 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0712 -0.0570 -0.9766 C 0 0 2 0 0 0 0 0 0 0 0 0 14.0347 0.6054 -0.1246 C 0 0 1 0 0 0 0 0 0 0 0 0 13.1917 1.5317 -0.9799 C 0 0 1 0 0 0 0 0 0 0 0 0 13.9567 2.5594 -1.5278 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1715 -0.3712 0.3732 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0747 0.8823 -1.2546 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4619 -1.6800 -4.1595 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7856 -1.0268 4.9930 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5088 -0.0707 5.8121 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3879 -1.3676 -2.6557 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0003 -1.5918 1.2915 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7910 -0.3260 1.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3234 0.2527 0.5400 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.6542 0.7008 -0.0277 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.6943 2.1803 -0.3423 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.7592 2.4283 -1.2180 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7125 0.4450 0.8321 O 0 0 0 0 0 0 0 0 0 0 0 0 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0 0 0 0 0 0 0 0 0 0 0 0 9.4662 -3.0206 -1.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1109 -3.3919 -3.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4489 -2.5719 -2.5820 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4908 0.2637 -2.7303 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1280 -1.4279 -0.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5551 0.4669 0.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0244 1.2893 -2.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4384 -0.8154 -2.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9707 -1.5279 -2.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4900 -0.9095 -0.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5581 1.1574 0.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3138 1.9201 -0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6490 3.4205 -1.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1138 -0.3021 1.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2521 1.3519 -0.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3361 -1.3778 -4.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5572 -1.6493 4.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3186 -0.0047 6.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8134 -2.0317 -3.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7263 -2.3841 1.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0197 -2.1548 1.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8867 -0.7981 2.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7795 0.1087 1.9658 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 -1.3877 1.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0607 0.1615 2.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2489 0.5317 1.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8686 0.1129 -0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8494 2.7758 0.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0293 1.5725 -1.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3696 0.5870 1.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3915 -1.5784 1.3388 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 12 14 1 0 11 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 6 22 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 29 32 1 0 32 33 1 0 26 34 1 1 34 35 2 0 34 36 1 0 36 37 1 0 37 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 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 66 69 1 0 65 70 1 0 57 71 1 0 41 72 1 0 40 73 1 0 25 74 1 0 17 75 1 1 10 76 1 1 5 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 78 81 1 0 77 82 1 0 79 3 1 0 12 7 1 0 22 17 1 0 33 26 1 0 42 37 1 0 50 44 1 0 59 54 1 0 67 62 1 0 18 10 1 0 27 21 1 0 1 83 1 0 2 84 1 0 2 85 1 0 3 86 1 6 5 87 1 6 7 88 1 6 8 89 1 0 8 90 1 0 9 91 1 0 9 92 1 0 11 93 1 6 13 94 1 0 13 95 1 0 13 96 1 0 14 97 1 0 14 98 1 0 14 99 1 0 15100 1 0 15101 1 0 16102 1 0 16103 1 0 18104 1 6 19105 1 0 19106 1 0 20107 1 0 23108 1 0 23109 1 0 23110 1 0 24111 1 0 24112 1 0 25113 1 1 27114 1 1 28115 1 0 28116 1 0 30117 1 0 30118 1 0 30119 1 0 31120 1 0 31121 1 0 31122 1 0 32123 1 0 32124 1 0 33125 1 0 33126 1 0 37127 1 6 39128 1 0 39129 1 0 40130 1 1 41131 1 6 42132 1 1 44133 1 1 46134 1 1 47135 1 0 47136 1 0 47137 1 0 48138 1 6 49139 1 1 50140 1 1 51141 1 0 52142 1 0 54143 1 6 56144 1 0 56145 1 0 57146 1 6 58147 1 6 59148 1 1 60149 1 0 62150 1 6 64151 1 0 64152 1 0 65153 1 1 66154 1 1 67155 1 1 68156 1 0 69157 1 0 70158 1 0 71159 1 0 72160 1 0 73161 1 0 74162 1 0 75163 1 0 75164 1 0 75165 1 0 76166 1 0 76167 1 0 76168 1 0 77169 1 1 78170 1 6 79171 1 1 80172 1 0 81173 1 0 82174 1 0 M END

Standard InCHIKey	ZXFNMDBLCLWZIE-YZHLYORDSA-N
Standard InCHI	InChI=1S/C57H92O25/c1-23-43(79-47-42(71)44(28(61)22-74-47)80-46-39(68)34(63)26(59)20-73-46)38(67)41(70)48(76-23)81-45-35(64)27(60)21-75-50(45)82-51(72)57-16-15-52(2,3)17-25(57)24-9-10-31-54(6)13-12-33(78-49-40(69)37(66)36(65)29(19-58)77-49)53(4,5)30(54)11-14-55(31,7)56(24,8)18-32(57)62/h9,23,25-50,58-71H,10-22H2,1-8H3/t23-,25-,26+,27-,28+,29+,30-,31+,32+,33-,34-,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45+,46-,47-,48-,49-,50-,54-,55+,56+,57+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1176.59	Volume:	1123.346 ? Van der Waals volume.
Dense:	1.047	LogP:	0.983 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.806 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.588 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	57.0
TPSA:	392.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.179	Fsp³:	0.947
MCE-18:	216.432 ? 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:	0.722	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.244	Promiscuous compounds:	0.104

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.558	MDCK Permeability:	-5.028
Pgp-inhibitor:	0.0	Pgp-substrate:	0.969
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):	0.42
20% Bioavailability (F20%):	0.257	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	60.563%	Volume Distribution (VD):	-0.386
Fu:	24.752% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.036
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.015
HLM stability:	0.12 ? 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):

-0.526

Half-life (T1/2):

3.801

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.763	Drug-induced Liver Injury (DILI):	0.946
AMES Toxicity:	0.959	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.513	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.06	RPMI-8226 Immunitoxicity:	0.366
A549 Cytotoxicity:	0.888	Hek293 Cytotoxicity:	0.355
BCF:	1.069 ? 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:	3.48 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.999 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.896 ? 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
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249983]
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26359	Aster lingulatus	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
IC50	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6100.0	nM	PMID[19128055]

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 NPC85154 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	23834
0.1-0.2	22101
0.2-0.3	2653
0.3-0.4	699
0.4-0.5	304
0.5-0.6	120
0.6-0.7	47
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9135	High Similarity	NPC104137
0.9135	High Similarity	NPC26626
0.8919	High Similarity	NPC13998
0.8421	Intermediate Similarity	NPC286457
0.8167	Intermediate Similarity	NPC102505
0.8167	Intermediate Similarity	NPC488514
0.8115	Intermediate Similarity	NPC33012
0.8033	Intermediate Similarity	NPC8524
0.7983	Intermediate Similarity	NPC309223
0.7833	Intermediate Similarity	NPC144644
0.7833	Intermediate Similarity	NPC37860
0.7833	Intermediate Similarity	NPC170407
0.7797	Intermediate Similarity	NPC473452
0.7778	Intermediate Similarity	NPC164389
0.7699	Intermediate Similarity	NPC815
0.7623	Intermediate Similarity	NPC70809
0.7581	Intermediate Similarity	NPC68767
0.7581	Intermediate Similarity	NPC293031
0.7438	Intermediate Similarity	NPC470876
0.7417	Intermediate Similarity	NPC237191
0.7264	Intermediate Similarity	NPC1046
0.7244	Intermediate Similarity	NPC489209
0.7203	Intermediate Similarity	NPC123522
0.719	Intermediate Similarity	NPC4749
0.7143	Intermediate Similarity	NPC220160
0.7122	Intermediate Similarity	NPC23020
0.7025	Intermediate Similarity	NPC283417
0.7025	Intermediate Similarity	NPC200049
0.7016	Intermediate Similarity	NPC475514
0.7008	Intermediate Similarity	NPC224381
0.7008	Intermediate Similarity	NPC142151
0.7008	Intermediate Similarity	NPC267694
0.6992	Remote Similarity	NPC473386
0.6978	Remote Similarity	NPC485563
0.6977	Remote Similarity	NPC110385
0.6977	Remote Similarity	NPC153673
0.6972	Remote Similarity	NPC472270
0.6972	Remote Similarity	NPC112492
0.6917	Remote Similarity	NPC489208
0.6855	Remote Similarity	NPC21691
0.6855	Remote Similarity	NPC57484
0.6846	Remote Similarity	NPC51099
0.6842	Remote Similarity	NPC488526
0.6829	Remote Similarity	NPC471577
0.6818	Remote Similarity	NPC275225
0.6807	Remote Similarity	NPC11242
0.6719	Remote Similarity	NPC302543
0.6692	Remote Similarity	NPC480421
0.6614	Remote Similarity	NPC471580
0.6613	Remote Similarity	NPC480423
0.6609	Remote Similarity	NPC117714
0.6594	Remote Similarity	NPC472268
0.6522	Remote Similarity	NPC297950
0.65	Remote Similarity	NPC475394
0.646	Remote Similarity	NPC475516
0.6446	Remote Similarity	NPC481078
0.6418	Remote Similarity	NPC480422
0.6408	Remote Similarity	NPC475584
0.6408	Remote Similarity	NPC475152
0.6387	Remote Similarity	NPC64715
0.6299	Remote Similarity	NPC488560
0.6293	Remote Similarity	NPC263756
0.629	Remote Similarity	NPC475287
0.6259	Remote Similarity	NPC472269
0.622	Remote Similarity	NPC475160
0.622	Remote Similarity	NPC473714
0.6186	Remote Similarity	NPC30289
0.6142	Remote Similarity	NPC123199
0.6136	Remote Similarity	NPC481081
0.6134	Remote Similarity	NPC232237
0.6107	Remote Similarity	NPC41061
0.6107	Remote Similarity	NPC227551
0.6017	Remote Similarity	NPC469946
0.6016	Remote Similarity	NPC481079
0.6015	Remote Similarity	NPC236638
0.6015	Remote Similarity	NPC294453
0.6015	Remote Similarity	NPC305981
0.6	Remote Similarity	NPC482010
0.6	Remote Similarity	NPC481080
0.5984	Remote Similarity	NPC79643
0.597	Remote Similarity	NPC261506
0.597	Remote Similarity	NPC4328
0.5966	Remote Similarity	NPC112352
0.5954	Remote Similarity	NPC476068
0.595	Remote Similarity	NPC63159
0.5949	Remote Similarity	NPC476113
0.592	Remote Similarity	NPC207738
0.5903	Remote Similarity	NPC329893
0.5891	Remote Similarity	NPC135904
0.5887	Remote Similarity	NPC475368
0.5882	Remote Similarity	NPC76497
0.5882	Remote Similarity	NPC213674
0.5847	Remote Similarity	NPC173583
0.584	Remote Similarity	NPC69811
0.5839	Remote Similarity	NPC250247
0.5789	Remote Similarity	NPC265841
0.5786	Remote Similarity	NPC485562
0.5782	Remote Similarity	NPC475892
0.5772	Remote Similarity	NPC297263
0.5759	Remote Similarity	NPC475527
0.5733	Remote Similarity	NPC311178
0.5733	Remote Similarity	NPC478559
0.5733	Remote Similarity	NPC478560
0.5724	Remote Similarity	NPC484831
0.5724	Remote Similarity	NPC484830
0.5714	Remote Similarity	NPC480420
0.5691	Remote Similarity	NPC105800
0.5677	Remote Similarity	NPC322904
0.5669	Remote Similarity	NPC31838
0.5669	Remote Similarity	NPC187290
0.5659	Remote Similarity	NPC60557
0.5659	Remote Similarity	NPC67857
0.5649	Remote Similarity	NPC480419
0.5645	Remote Similarity	NPC475504
0.5635	Remote Similarity	NPC301449
0.5635	Remote Similarity	NPC601290
0.5633	Remote Similarity	NPC488204
0.5625	Remote Similarity	NPC475177
0.561	Remote Similarity	NPC305267
0.561	Remote Similarity	NPC46665
0.5592	Remote Similarity	NPC222951
0.5591	Remote Similarity	NPC295823
0.5591	Remote Similarity	NPC174720
0.5591	Remote Similarity	NPC475467
0.559	Remote Similarity	NPC488513
0.5583	Remote Similarity	NPC58448
0.5581	Remote Similarity	NPC185466
0.5574	Remote Similarity	NPC223301
0.5574	Remote Similarity	NPC171544
0.557	Remote Similarity	NPC233223
0.557	Remote Similarity	NPC183816
0.557	Remote Similarity	NPC43589
0.5556	Remote Similarity	NPC104372
0.5556	Remote Similarity	NPC488308
0.5547	Remote Similarity	NPC202828
0.5547	Remote Similarity	NPC119592
0.5538	Remote Similarity	NPC610204
0.553	Remote Similarity	NPC475209
0.5515	Remote Similarity	NPC271610
0.5515	Remote Similarity	NPC312650
0.5507	Remote Similarity	NPC33068
0.5507	Remote Similarity	NPC298034
0.5507	Remote Similarity	NPC71065
0.5503	Remote Similarity	NPC484829
0.55	Remote Similarity	NPC235405
0.55	Remote Similarity	NPC488201
0.5489	Remote Similarity	NPC471550
0.5476	Remote Similarity	NPC302887
0.5474	Remote Similarity	NPC293330
0.5474	Remote Similarity	NPC43550
0.5462	Remote Similarity	NPC475208
0.5462	Remote Similarity	NPC48499
0.5455	Remote Similarity	NPC475444
0.5455	Remote Similarity	NPC249848
0.5455	Remote Similarity	NPC473679
0.5455	Remote Similarity	NPC107966
0.5455	Remote Similarity	NPC488619
0.5443	Remote Similarity	NPC324933
0.5441	Remote Similarity	NPC110633
0.5441	Remote Similarity	NPC480418
0.544	Remote Similarity	NPC235438
0.543	Remote Similarity	NPC300655
0.543	Remote Similarity	NPC13989
0.543	Remote Similarity	NPC196874
0.5426	Remote Similarity	NPC475486
0.5424	Remote Similarity	NPC90856
0.542	Remote Similarity	NPC300419
0.5414	Remote Similarity	NPC251263
0.5414	Remote Similarity	NPC603137
0.5403	Remote Similarity	NPC30735
0.54	Remote Similarity	NPC329878
0.5385	Remote Similarity	NPC210729
0.5385	Remote Similarity	NPC82931
0.5366	Remote Similarity	NPC80843
0.536	Remote Similarity	NPC44716
0.536	Remote Similarity	NPC2370
0.536	Remote Similarity	NPC480475
0.5352	Remote Similarity	NPC478825
0.5349	Remote Similarity	NPC160452
0.5344	Remote Similarity	NPC288205
0.5344	Remote Similarity	NPC51465
0.5338	Remote Similarity	NPC284449
0.5333	Remote Similarity	NPC484546
0.5319	Remote Similarity	NPC488309
0.5312	Remote Similarity	NPC319719
0.5299	Remote Similarity	NPC128925
0.5294	Remote Similarity	NPC214484
0.529	Remote Similarity	NPC484942
0.529	Remote Similarity	NPC488618
0.5285	Remote Similarity	NPC295371
0.5285	Remote Similarity	NPC39211
0.528	Remote Similarity	NPC265699
0.528	Remote Similarity	NPC475599
0.5276	Remote Similarity	NPC222580
0.5276	Remote Similarity	NPC488517
0.5271	Remote Similarity	NPC324875
0.5271	Remote Similarity	NPC292677
0.5259	Remote Similarity	NPC475140
0.5259	Remote Similarity	NPC602995

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7685
0.1-0.2	1413
0.2-0.3	48
0.3-0.4	4
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