NPASS Compound

Natural Product: NPC192763

Natural Product ID	NPC192763
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quiquesetinerviuside C
IUPAC Name	[(2R,3R,4S,5S)-5-[(2R,3R,4S,5S,6R)-3-acetyloxy-4-hydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-(hydroxymethyl)oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms	quiquesetinerviuside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1224879
PubChem CID	49866358
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 113117 0 0 0 0 0 0 0 0999 V2000 5.2077 -1.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 -0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 1.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9237 3.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 3.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3677 4.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7772 5.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7007 4.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8498 3.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9988 2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4084 2.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6688 4.1813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5574 1.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9670 2.2529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1160 1.2887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8556 -0.1885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0046 -1.1527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4142 -0.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6746 0.8376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5256 1.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0842 1.3506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3447 2.8278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5632 -1.6038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8619 2.8758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0493 6.0963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0048 6.2438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0838 7.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5257 6.8723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7209 8.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7999 9.7832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4370 11.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5160 12.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1532 13.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7113 14.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6323 13.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9951 11.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1904 13.5210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8886 12.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3484 15.6050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2709 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 -3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9786 -2.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3882 -3.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6486 -4.8284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0582 -5.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2072 -4.3772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9468 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5372 -2.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0958 -1.9358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8354 -0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6168 -4.8902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1719 -0.2663 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 -2.5644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 -2.3795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6715 -2.7970 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6132 -0.1849 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6849 2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 1.4153 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3897 2.1082 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6773 2.6358 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 4.8919 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 4.8467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8679 4.7622 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4654 6.7686 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8987 5.0221 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8856 2.0061 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8139 4.3043 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2970 0.2627 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2274 3.7301 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4460 -0.7015 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7442 -2.6299 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7860 3.2790 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8219 2.5673 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8674 3.0883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6051 4.3050 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9728 -1.0908 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4497 5.5588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2790 9.1547 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2418 9.3698 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9579 11.8672 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2322 14.7781 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 10.6101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9306 13.5580 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1533 11.4000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9677 11.4371 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9065 16.0185 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0900 -5.2795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -1.3609 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4996 -5.7926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3186 -6.8186 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2768 -0.9098 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3126 -0.1981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3581 -0.7191 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5749 1.0186 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7658 -3.9261 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8470 -3.4573 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 8 11 1 0 11 12 1 0 12 13 1 0 14 13 1 1 14 15 1 0 15 16 1 0 14 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 29 34 1 0 19 35 1 0 18 36 1 0 17 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 45 50 1 0 7 51 1 0 51 52 1 0 52 53 2 0 52 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 1 0 59 64 1 0 6 65 1 0 12 5 1 0 35 14 1 0 47 42 1 0 61 56 1 0 31 26 1 0 1 66 1 0 1 67 1 0 1 68 1 0 5 69 1 1 6 70 1 6 7 71 1 1 8 72 1 6 9 73 1 0 9 74 1 0 10 75 1 0 12 76 1 1 15 77 1 0 15 78 1 0 16 79 1 0 17 80 1 6 18 81 1 1 19 82 1 6 20 83 1 0 20 84 1 0 24 85 1 0 25 86 1 0 27 87 1 0 28 88 1 0 31 89 1 0 33 90 1 0 33 91 1 0 33 92 1 0 34 93 1 0 36 94 1 0 40 95 1 0 41 96 1 0 43 97 1 0 44 98 1 0 47 99 1 0 49100 1 0 49101 1 0 49102 1 0 50103 1 0 54104 1 0 55105 1 0 57106 1 0 58107 1 0 61108 1 0 63109 1 0 63110 1 0 63111 1 0 64112 1 0 65113 1 0 M END

Standard InCHIKey	HULSANORWWCGEU-QMRYJMHISA-N
Standard InCHI	InChI=1S/C44H48O21/c1-23(47)60-41-39(55)40(62-36(52)15-9-25-6-12-28(49)31(18-25)57-3)33(20-45)61-43(41)65-44(22-46)42(63-37(53)16-10-26-7-13-29(50)32(19-26)58-4)38(54)34(64-44)21-59-35(51)14-8-24-5-11-27(48)30(17-24)56-2/h5-19,33-34,38-43,45-46,48-50,54-55H,20-22H2,1-4H3/b14-8+,15-9+,16-10+/t33-,34-,38-,39+,40-,41-,42+,43-,44+/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1O[C@@]1(CO)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O1)O)OC(=O)/C=C/c1ccc(c(c1)OC)O)OC(=O)/C=C/c1ccc(c(c1)OC)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	912.27	Volume:	869.209 ? Van der Waals volume.
Dense:	1.05	LogP:	1.546 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.863 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.293 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	Rigid Bonds:	36.0
TPSA:	302.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.053	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.383	Fsp³:	0.364
MCE-18:	128.7 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.981	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.177 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.663 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.216	Promiscuous compounds:	0.282

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097	MDCK Permeability:	-5.508
Pgp-inhibitor:	0.426	Pgp-substrate:	0.008
PAMPA:	0.69 ? 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):	0.898
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	68.457%	Volume Distribution (VD):	-0.388
Fu:	27.719% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.219
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.832 ? 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):

1.907

Half-life (T1/2):

2.832

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.371
Human Hepatotoxicity (H-HT):	0.5	Drug-induced Liver Injury (DILI):	0.891
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.446	Skin Sensitization:	1.0
Carcinogencity:	0.04	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.12	Ototoxicity:	0.808
Hematotoxicity:	0.121	Drug-induced Nephrotoxicity:	0.882
Genotoxicity:	0.417	RPMI-8226 Immunitoxicity:	0.394
A549 Cytotoxicity:	0.928	Hek293 Cytotoxicity:	0.768
BCF:	0.479 ? 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:	3.333 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.989 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.323 ? 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
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20056545]
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20825224]
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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	4
Activity	2

Activity Type	# Activity
Cell line	3
Others	1
Non-molecular	2

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	42100.0	nM	DOI[10.6019/CHEMBL1201861]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[23398362]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3600.0	nM	PMID[20825224]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	184300.0	nM	PMID[20825224]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	69100.0	nM	PMID[19506058]

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 NPC192763 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	10271
0.1-0.2	35035
0.2-0.3	3893
0.3-0.4	537
0.4-0.5	95
0.5-0.6	15
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC210611
0.8395	Intermediate Similarity	NPC216819
0.7738	Intermediate Similarity	NPC80732
0.7273	Intermediate Similarity	NPC199311
0.7093	Intermediate Similarity	NPC262182
0.7079	Intermediate Similarity	NPC287615
0.6957	Remote Similarity	NPC261122
0.6667	Remote Similarity	NPC300262
0.663	Remote Similarity	NPC85192
0.6559	Remote Similarity	NPC215095
0.6444	Remote Similarity	NPC83743
0.5889	Remote Similarity	NPC472612
0.5816	Remote Similarity	NPC201148
0.5773	Remote Similarity	NPC3460
0.567	Remote Similarity	NPC125823
0.567	Remote Similarity	NPC7145
0.567	Remote Similarity	NPC143480
0.5556	Remote Similarity	NPC472611
0.5556	Remote Similarity	NPC225307
0.5495	Remote Similarity	NPC156692
0.5484	Remote Similarity	NPC226005
0.5426	Remote Similarity	NPC90896
0.5152	Remote Similarity	NPC283839
0.5106	Remote Similarity	NPC484687
0.5104	Remote Similarity	NPC44730
0.505	Remote Similarity	NPC173343

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC192763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3574
0.1-0.2	5477
0.2-0.3	95
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