NPASS Compound

Natural Product: NPC476074

Natural Product ID	NPC476074
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Symplocososide H
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-[(2E)-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]-4-acetyloxy-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	symplocososide H
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524699
PubChem CID	44566491
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 188195 0 0 0 0 0 0 0 0999 V2000 6.7560 -4.7829 -0.6677 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7261 -3.9599 0.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6927 -3.3137 -0.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6697 -2.5090 0.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9776 -2.4749 -1.7477 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0369 -2.7546 -2.9723 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2267 -1.3658 -1.4235 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5348 -0.5217 -2.2783 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1082 0.8697 -2.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3183 1.7952 -3.1762 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8431 1.6062 -3.2067 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4621 0.8066 -1.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0369 -0.5427 -1.9357 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8261 -1.0841 -0.5501 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6847 -0.5879 0.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5816 0.1526 -0.4504 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0158 0.7254 -1.7386 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1761 1.1857 -2.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7153 1.1222 -2.3651 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3341 -0.1199 -1.6008 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2692 -0.5835 -0.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7235 -0.6673 0.8483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7486 -0.9556 0.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4981 0.0099 0.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1549 -0.2072 -1.3584 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9418 0.7329 -2.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9568 1.5650 -1.4849 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8304 0.6485 -0.6026 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9538 0.0627 0.4443 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -1.2667 0.9046 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0482 1.0068 1.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8910 1.2489 -0.0330 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1529 1.0111 -0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9643 0.1372 0.4785 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0451 0.7802 1.8280 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4657 2.2574 1.6808 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6479 2.8976 0.6232 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7537 2.2604 -0.6122 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9027 4.3279 0.5177 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0826 4.7904 -0.6755 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9611 5.1978 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0 0 0 0 0 0 0 0 -8.9588 -2.1723 0.5857 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3434 -4.3676 1.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3455 -4.1677 2.2926 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9703 -4.5910 -0.5106 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5357 -1.9990 -0.5774 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0569 -1.2077 -2.9014 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5488 -1.6226 -1.8402 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5839 -2.0684 -0.8640 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3391 1.4555 0.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2854 -1.5638 1.1317 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0349 -0.7506 0.1377 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 -1.5166 -2.9378 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7123 -1.1035 -4.2521 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6787 3.2354 -2.7619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8145 1.6973 -4.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5173 1.3753 -1.0806 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8560 1.5455 -0.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6840 1.2072 -1.6081 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3001 2.0679 0.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6019 2.1817 0.7831 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6487 1.8088 -0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0393 2.7355 2.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8128 1.7660 2.9315 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0461 1.2543 2.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2722 0.0053 1.9606 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6170 -0.3075 1.3551 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3207 -1.1149 2.0771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8791 -5.0744 -0.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3025 -5.6863 -1.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4436 -4.2114 -1.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2605 -4.6262 0.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1660 -3.1678 0.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2528 -4.1168 -1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3454 -3.2560 0.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3233 -1.8461 -0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1772 -1.9885 0.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6826 -0.9153 -3.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1013 0.7100 -2.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3668 2.6015 -3.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4791 1.2004 -4.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9632 1.3897 -1.1350 H 0 0 0 0 0 0 0 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0.0442 0.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3192 -1.4948 -2.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7491 -2.5572 -2.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0837 -1.5745 -4.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5851 3.2969 -1.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7586 3.3949 -3.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0578 3.9593 -3.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3860 2.5147 -5.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6013 0.6949 -5.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9212 1.8241 -4.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5911 2.3655 1.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6911 0.7391 -0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4978 2.4077 -1.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6370 2.1448 0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6939 3.6070 1.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1923 3.1240 2.6806 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1837 0.9378 3.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1315 2.3555 3.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8579 1.9876 2.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5624 -0.1323 0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3911 0.3626 1.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9316 -1.3462 1.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3280 -0.7689 2.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7026 -1.9274 2.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1956 -1.5793 1.0611 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 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 45 50 1 0 44 51 1 0 35 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 34 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 61 63 1 0 63 64 1 0 60 65 1 0 59 66 1 0 58 67 1 0 25 68 1 0 21 69 1 0 16 70 1 0 15 71 1 0 14 72 1 0 13 73 1 0 73 74 1 0 10 75 1 0 10 76 1 0 9 77 1 0 77 78 1 0 78 79 2 0 78 80 1 0 80 81 2 3 81 82 1 0 81 83 1 0 83 84 1 0 84 85 1 0 85 86 2 3 86 87 1 0 86 88 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 47 43 1 0 62 57 1 0 1 89 1 0 1 90 1 0 1 91 1 0 2 92 1 0 2 93 1 0 3 94 1 0 4 95 1 0 4 96 1 0 4 97 1 0 8 98 1 0 9 99 1 0 11100 1 0 11101 1 0 12102 1 0 14103 1 0 15104 1 0 18105 1 0 19106 1 0 19107 1 0 20108 1 0 22109 1 0 22110 1 0 23111 1 0 23112 1 0 24113 1 0 26114 1 0 26115 1 0 27116 1 0 27117 1 0 28118 1 0 30119 1 0 30120 1 0 30121 1 0 31122 1 0 31123 1 0 31124 1 0 33125 1 0 34126 1 0 35127 1 0 36128 1 0 37129 1 0 41130 1 0 43131 1 0 44132 1 0 45133 1 0 46134 1 0 48135 1 0 48136 1 0 49137 1 0 50138 1 0 51139 1 0 55140 1 0 55141 1 0 55142 1 0 57143 1 0 58144 1 0 59145 1 0 60146 1 0 61147 1 0 63148 1 0 63149 1 0 64150 1 0 65151 1 0 66152 1 0 67153 1 0 68154 1 0 68155 1 0 68156 1 0 69157 1 0 69158 1 0 69159 1 0 70160 1 0 70161 1 0 70162 1 0 71163 1 0 72164 1 0 73165 1 0 73166 1 0 74167 1 0 75168 1 0 75169 1 0 75170 1 0 76171 1 0 76172 1 0 76173 1 0 80174 1 0 82175 1 0 82176 1 0 82177 1 0 83178 1 0 83179 1 0 84180 1 0 84181 1 0 85182 1 0 87183 1 0 87184 1 0 87185 1 0 88186 1 0 88187 1 0 88188 1 0 M END

Standard InCHIKey	IGZKUEHSCWAURC-TVCTUJPYSA-N
Standard InCHI	InChI=1S/C64H100O24/c1-14-31(5)55(79)88-53-52(84-40(69)24-30(4)17-15-16-29(2)3)59(7,8)25-34-33-18-19-38-61(11)22-21-39(60(9,10)37(61)20-23-62(38,12)63(33,13)50(75)51(76)64(34,53)28-67)83-58-49(87-57-45(74)43(72)41(70)35(26-65)81-57)47(80-32(6)68)46(48(86-58)54(77)78)85-56-44(73)42(71)36(27-66)82-56/h16,18,24,31,34-39,41-53,56-58,65-67,70-76H,14-15,17,19-23,25-28H2,1-13H3,(H,77,78)/b30-24+/t31?,34-,35+,36-,37-,38+,39-,41+,42-,43-,44+,45+,46-,47-,48-,49+,50-,51+,52-,53-,56-,57-,58+,61-,62+,63-,64-/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)OC7C(C(C(O7)CO)O)O)OC(=O)C)OC8C(C(C(C(O8)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:	1252.66	Volume:	1239.558 ? Van der Waals volume.
Dense:	1.011	LogP:	3.716 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.238 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.083 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	Rigid Bonds:	49.0
TPSA:	373.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.029	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.303	Fsp³:	0.844
MCE-18:	185.492 ? 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:	0.204	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:	0.331 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.429	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.277	MDCK Permeability:	-5.091
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	1.0
20% Bioavailability (F20%):	0.749	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	57.986%	Volume Distribution (VD):	-0.523
Fu:	25.022% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.069	BCRP inhibitor:	0.0
BSEP inhibitor:	0.062

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.422	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.813	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:	0.0
HLM stability:	0.004 ? 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):

-0.309

Half-life (T1/2):

3.706

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.061
Human Hepatotoxicity (H-HT):	0.333	Drug-induced Liver Injury (DILI):	0.142
AMES Toxicity:	0.039	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.217	Skin Sensitization:	0.196
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.21	Ototoxicity:	1.0
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.038
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.467
BCF:	0.245 ? 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:	4.63 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.03 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.961 ? 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	=	2100.0	nM	PMID[22440015]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	2600.0	nM	PMID[24904961]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	2500.0	nM	PMID[23398362]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2700.0	nM	PMID[26115570]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	1400.0	nM	PMID[25798528]

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 NPC476074 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	21267
0.1-0.2	24601
0.2-0.3	3187
0.3-0.4	608
0.4-0.5	136
0.5-0.6	35
0.6-0.7	12
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475377
0.9459	High Similarity	NPC262796
0.9459	High Similarity	NPC45346
0.8374	Intermediate Similarity	NPC150893
0.8348	Intermediate Similarity	NPC264566
0.8051	Intermediate Similarity	NPC329923
0.8051	Intermediate Similarity	NPC475281
0.8051	Intermediate Similarity	NPC475167
0.7967	Intermediate Similarity	NPC329960
0.7642	Intermediate Similarity	NPC484833
0.7258	Intermediate Similarity	NPC134914
0.7143	Intermediate Similarity	NPC329993
0.6977	Remote Similarity	NPC173435
0.6977	Remote Similarity	NPC172374
0.6977	Remote Similarity	NPC478064
0.686	Remote Similarity	NPC329976
0.6742	Remote Similarity	NPC295408
0.6719	Remote Similarity	NPC473755
0.6515	Remote Similarity	NPC329657
0.6504	Remote Similarity	NPC477078
0.6212	Remote Similarity	NPC178264
0.6183	Remote Similarity	NPC46823
0.6136	Remote Similarity	NPC192765
0.6	Remote Similarity	NPC475513
0.5984	Remote Similarity	NPC477077
0.5952	Remote Similarity	NPC470914
0.5896	Remote Similarity	NPC301639
0.5896	Remote Similarity	NPC478065
0.5891	Remote Similarity	NPC605294
0.5846	Remote Similarity	NPC25998
0.5789	Remote Similarity	NPC478150
0.5786	Remote Similarity	NPC488309
0.5775	Remote Similarity	NPC69425
0.5725	Remote Similarity	NPC478152
0.5725	Remote Similarity	NPC478151
0.5704	Remote Similarity	NPC470912
0.5704	Remote Similarity	NPC473918
0.5691	Remote Similarity	NPC603026
0.5669	Remote Similarity	NPC470913
0.5659	Remote Similarity	NPC477075
0.5588	Remote Similarity	NPC277212
0.5588	Remote Similarity	NPC30279
0.5547	Remote Similarity	NPC71391
0.5547	Remote Similarity	NPC329828
0.554	Remote Similarity	NPC225791
0.553	Remote Similarity	NPC606553
0.5515	Remote Similarity	NPC602995
0.5429	Remote Similarity	NPC312650
0.5396	Remote Similarity	NPC478598
0.5385	Remote Similarity	NPC473586
0.5357	Remote Similarity	NPC488308
0.5319	Remote Similarity	NPC271610
0.5221	Remote Similarity	NPC609119
0.5188	Remote Similarity	NPC477076
0.5147	Remote Similarity	NPC107536
0.5147	Remote Similarity	NPC280029
0.5147	Remote Similarity	NPC9470
0.513	Remote Similarity	NPC476132
0.507	Remote Similarity	NPC470518

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6913
0.1-0.2	2183
0.2-0.3	51
0.3-0.4	3
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