NPASS Compound

Natural Product: NPC470716

Natural Product ID	NPC470716
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Allivictoside E
IUPAC Name	[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-3-yl]oxyoxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	Allivictoside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206201
PubChem CID	71463099
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 111117 0 0 0 0 0 0 0 0999 V2000 10.3966 -2.5874 2.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6716 -2.1299 2.7067 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0126 -0.9218 2.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0616 -0.1830 1.5358 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7430 -0.6807 1.4698 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3521 -1.8690 1.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0646 -2.4370 1.9686 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9250 -2.2023 1.4630 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3869 -1.1933 0.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9002 -0.2126 0.1755 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9893 -1.3018 0.2325 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3990 -0.3288 -0.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0215 -0.9444 -1.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8348 -1.8622 -1.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2471 -1.7636 -0.5396 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9260 -0.3859 -0.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1788 0.2591 0.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3566 0.0338 1.4590 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0038 -0.4303 0.7530 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 -0.7212 0.5142 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2617 0.2081 0.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5340 -0.1866 0.0183 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8651 -1.4462 0.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -1.7461 -0.1887 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5939 -3.0915 -0.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6497 -4.0556 0.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3171 -3.7608 0.3639 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9509 -2.4295 0.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6459 -2.0874 0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2175 -2.9410 0.8111 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3570 -4.6984 0.6372 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9279 -3.3649 -0.4004 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5293 -4.6165 -0.3836 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7371 -4.6663 0.5413 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2413 -6.0754 0.5679 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2976 -6.7600 -0.7549 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3997 -6.2092 -1.8126 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0273 -4.8989 -1.6604 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1753 -7.1110 -2.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5856 -8.4391 -2.1874 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6290 -6.8507 -1.2266 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5543 -6.0477 1.0937 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2586 -4.3442 1.8186 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9783 1.6332 0.1863 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1319 2.2637 0.6733 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3608 3.6042 0.5381 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5818 4.4113 -0.1373 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6999 3.8282 -0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9016 2.4572 -0.4810 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3330 5.7470 -0.2550 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0887 6.7030 -0.9412 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9361 7.4001 0.1417 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5846 8.6387 -0.3588 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1205 9.0436 -1.7264 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6626 8.7779 -1.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2122 7.5552 -1.5590 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2004 9.8236 -1.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1719 11.1187 -1.5571 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3362 10.4305 -1.8486 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2546 9.7076 0.5017 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1418 7.6398 1.2526 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2437 -3.3061 -1.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1656 -4.1729 -1.9296 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1325 -1.6400 -2.3886 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3361 -0.4766 2.2507 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1626 -3.5298 3.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4798 -2.6860 3.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2939 0.7752 1.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0666 -0.0362 0.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9832 -3.4365 2.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1279 -3.0152 1.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1147 0.4589 -0.7836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7767 -0.1769 -2.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0421 -1.6392 -2.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4150 -0.0387 -1.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1130 1.3521 -0.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6120 0.3272 2.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9511 -0.9942 -0.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9157 -5.0955 0.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5965 -5.6878 0.4659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8269 -5.3757 -0.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5212 -3.9726 0.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5906 -6.6280 1.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9655 -7.8264 -0.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9634 -6.2625 -2.7873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6135 -6.8213 -2.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4704 -7.0238 -1.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2053 -9.0126 -1.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7678 -6.2616 -1.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7124 -5.2106 1.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7775 -3.6446 2.2753 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8673 1.7074 1.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2480 4.1070 0.9262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4394 4.4200 -1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7901 2.0022 -0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7917 6.2270 -1.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7487 6.6788 0.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6896 8.5180 -0.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7650 8.5642 -2.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4951 8.8725 -3.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2748 9.6415 -1.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0490 9.6745 -0.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4275 11.4402 -2.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8585 10.7888 -1.0725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9954 9.9573 1.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6315 7.5470 2.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9343 -3.6371 -1.1596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8360 -3.4713 -2.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0369 -4.4523 -0.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5098 -1.3193 -3.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5161 0.4894 2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 2 0 9 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 2 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 27 31 1 0 25 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 1 0 36 41 1 0 35 42 1 0 34 43 1 0 21 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 47 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 55 57 1 0 57 58 1 0 54 59 1 0 53 60 1 0 52 61 1 0 14 62 1 0 62 63 1 0 13 64 1 0 3 65 1 0 6 1 1 0 17 12 1 0 29 20 1 0 28 23 1 0 38 33 1 0 49 44 1 0 56 51 1 0 1 66 1 0 2 67 1 0 4 68 1 0 5 69 1 0 7 70 1 0 8 71 1 0 12 72 1 0 13 73 1 0 14 74 1 0 16 75 1 0 17 76 1 0 18 77 1 0 24 78 1 0 26 79 1 0 31 80 1 0 33 81 1 0 34 82 1 0 35 83 1 0 36 84 1 0 37 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 41 89 1 0 42 90 1 0 43 91 1 0 45 92 1 0 46 93 1 0 48 94 1 0 49 95 1 0 51 96 1 0 52 97 1 0 53 98 1 0 54 99 1 0 55100 1 0 57101 1 0 57102 1 0 58103 1 0 59104 1 0 60105 1 0 61106 1 0 62107 1 0 62108 1 0 63109 1 0 64110 1 0 65111 1 0 M END

Standard InCHIKey	AZARVOKJABCVQG-BQYMUXTISA-N
Standard InCHI	InChI=1S/C42H46O23/c43-13-23-28(49)32(53)34(55)40(61-23)58-19-8-4-17(5-9-19)37-39(31(52)27-21(47)11-20(12-22(27)60-37)59-41-35(56)33(54)29(50)24(14-44)62-41)65-42-36(57)38(30(51)25(15-45)63-42)64-26(48)10-3-16-1-6-18(46)7-2-16/h1-12,23-25,28-30,32-36,38,40-47,49-51,53-57H,13-15H2/b10-3+/t23-,24-,25-,28-,29-,30-,32+,33+,34-,35-,36-,38+,40-,41-,42+/m1/s1
SMILES	C1=CC(=CC=C1C=CC(=O)OC2C(C(OC(C2O)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC=C(C=C6)OC7C(C(C(C(O7)CO)O)O)O)CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.24	Volume:	842.994 ? Van der Waals volume.
Dense:	1.089	LogP:	-0.713 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.237 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.412 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	374.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.638	Fsp³:	0.429
MCE-18:	168.0 ? 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:	0.352	Fluc inhibitor:	0.355 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.718 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.672 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.594	Promiscuous compounds:	0.489

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.872	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.0	Pgp-substrate:	0.965
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%):	0.975	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.914
Plasma Protein Binding (PPB):	77.371%	Volume Distribution (VD):	-0.107
Fu:	23.387% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.951	BCRP inhibitor:	0.146
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.331	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:	0.891
HLM stability:	0.0 ? 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):

0.869

Half-life (T1/2):

4.675

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.238
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.876
AMES Toxicity:	0.776	Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.163	Skin Sensitization:	0.255
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	1.0
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.069
Genotoxicity:	0.271	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.106	Hek293 Cytotoxicity:	0.97
BCF:	0.467 ? 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:	3.157 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.331 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.024 ? 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
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]

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	1
IC50	1

Activity Type	# Activity
Cell line	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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	103.8	%	PMID[17140705]
NPT34	Cell line	BV-2	Mus musculus	IC50	=	49480.0	nM	PMID[1375626]

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 NPC470716 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	18509
0.1-0.2	27166
0.2-0.3	3066
0.3-0.4	670
0.4-0.5	306
0.5-0.6	115
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC470715
0.7822	Intermediate Similarity	NPC164704
0.72	Intermediate Similarity	NPC205824
0.7196	Intermediate Similarity	NPC295625
0.7156	Intermediate Similarity	NPC470720
0.71	Intermediate Similarity	NPC210961
0.7064	Intermediate Similarity	NPC470717
0.7033	Intermediate Similarity	NPC289667
0.6981	Remote Similarity	NPC470712
0.6774	Remote Similarity	NPC297987
0.6607	Remote Similarity	NPC470719
0.6429	Remote Similarity	NPC116458
0.6429	Remote Similarity	NPC246943
0.6408	Remote Similarity	NPC64425
0.625	Remote Similarity	NPC136042
0.625	Remote Similarity	NPC470718
0.6228	Remote Similarity	NPC470713
0.6198	Remote Similarity	NPC223860
0.6078	Remote Similarity	NPC251417
0.6	Remote Similarity	NPC96605
0.6	Remote Similarity	NPC280642
0.5981	Remote Similarity	NPC606657
0.5941	Remote Similarity	NPC605784
0.5918	Remote Similarity	NPC64305
0.5859	Remote Similarity	NPC84362
0.5833	Remote Similarity	NPC104883
0.5833	Remote Similarity	NPC488679
0.5816	Remote Similarity	NPC249281
0.5798	Remote Similarity	NPC241781
0.5727	Remote Similarity	NPC85751
0.5727	Remote Similarity	NPC19240
0.5702	Remote Similarity	NPC473278
0.5688	Remote Similarity	NPC35119
0.5644	Remote Similarity	NPC472459
0.5636	Remote Similarity	NPC270675
0.5636	Remote Similarity	NPC195685
0.5603	Remote Similarity	NPC277532
0.5593	Remote Similarity	NPC474093
0.5593	Remote Similarity	NPC104910
0.5586	Remote Similarity	NPC80068
0.5577	Remote Similarity	NPC276377
0.5545	Remote Similarity	NPC46420
0.5545	Remote Similarity	NPC24043
0.5545	Remote Similarity	NPC32641
0.5545	Remote Similarity	NPC256188
0.5517	Remote Similarity	NPC25523
0.55	Remote Similarity	NPC39360
0.55	Remote Similarity	NPC77672
0.55	Remote Similarity	NPC133671
0.55	Remote Similarity	NPC135391
0.55	Remote Similarity	NPC29763
0.55	Remote Similarity	NPC78263
0.55	Remote Similarity	NPC210003
0.55	Remote Similarity	NPC250069
0.5487	Remote Similarity	NPC223426
0.5481	Remote Similarity	NPC220169
0.5463	Remote Similarity	NPC150164
0.5455	Remote Similarity	NPC488078
0.5446	Remote Similarity	NPC95090
0.5446	Remote Similarity	NPC27408
0.5437	Remote Similarity	NPC611303
0.5431	Remote Similarity	NPC477895
0.5398	Remote Similarity	NPC36138
0.5385	Remote Similarity	NPC22832
0.5372	Remote Similarity	NPC471030
0.5351	Remote Similarity	NPC483767
0.5351	Remote Similarity	NPC483769
0.5351	Remote Similarity	NPC484301
0.5351	Remote Similarity	NPC472994
0.5351	Remote Similarity	NPC483768
0.5351	Remote Similarity	NPC483766
0.5349	Remote Similarity	NPC249560
0.5328	Remote Similarity	NPC488079
0.5304	Remote Similarity	NPC214621
0.5304	Remote Similarity	NPC34267
0.5304	Remote Similarity	NPC14187
0.5294	Remote Similarity	NPC323593
0.5294	Remote Similarity	NPC203500
0.5294	Remote Similarity	NPC189142
0.5294	Remote Similarity	NPC77660
0.5288	Remote Similarity	NPC60735
0.5288	Remote Similarity	NPC26230
0.5288	Remote Similarity	NPC285197
0.5273	Remote Similarity	NPC186816
0.5268	Remote Similarity	NPC139060
0.5268	Remote Similarity	NPC72016
0.5254	Remote Similarity	NPC217520
0.5243	Remote Similarity	NPC488080
0.5243	Remote Similarity	NPC169977
0.5238	Remote Similarity	NPC243930
0.5238	Remote Similarity	NPC120099
0.5221	Remote Similarity	NPC101399
0.5221	Remote Similarity	NPC221288
0.5221	Remote Similarity	NPC217822
0.5221	Remote Similarity	NPC11847
0.5221	Remote Similarity	NPC198938
0.5221	Remote Similarity	NPC194836
0.5221	Remote Similarity	NPC91493
0.5221	Remote Similarity	NPC605081
0.5196	Remote Similarity	NPC261866
0.5188	Remote Similarity	NPC475179
0.5179	Remote Similarity	NPC476619
0.5179	Remote Similarity	NPC477628
0.5175	Remote Similarity	NPC188815
0.5169	Remote Similarity	NPC472993
0.5146	Remote Similarity	NPC145038
0.5146	Remote Similarity	NPC8573
0.5146	Remote Similarity	NPC56077
0.5146	Remote Similarity	NPC197896
0.5146	Remote Similarity	NPC281131
0.5146	Remote Similarity	NPC313163
0.5146	Remote Similarity	NPC253662
0.5146	Remote Similarity	NPC179950
0.5146	Remote Similarity	NPC277205
0.5146	Remote Similarity	NPC37919
0.5146	Remote Similarity	NPC88789
0.5146	Remote Similarity	NPC491374
0.5143	Remote Similarity	NPC488071
0.5128	Remote Similarity	NPC121703
0.5126	Remote Similarity	NPC480441
0.5122	Remote Similarity	NPC156785
0.5096	Remote Similarity	NPC271692
0.5094	Remote Similarity	NPC21666
0.5094	Remote Similarity	NPC486578
0.5094	Remote Similarity	NPC601144
0.5089	Remote Similarity	NPC470125
0.5089	Remote Similarity	NPC240306
0.5088	Remote Similarity	NPC5319
0.5086	Remote Similarity	NPC218161
0.5047	Remote Similarity	NPC311830
0.5043	Remote Similarity	NPC76831
0.5043	Remote Similarity	NPC81042
0.5043	Remote Similarity	NPC477629
0.5042	Remote Similarity	NPC480796
0.504	Remote Similarity	NPC138990
0.5036	Remote Similarity	NPC33083

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4959
0.1-0.2	4135
0.2-0.3	46
0.3-0.4	4
0.4-0.5	5
0.5-0.6	1
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
0.5088	Remote Similarity	NPD7804	Clinical (unspecified phase)

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