NPASS Compound

Natural Product: NPC106565

Natural Product ID	NPC106565
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LVFWZZFIRQCFMJ-DYUFTDJRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24862644
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

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 105109 0 0 0 0 0 0 0 0999 V2000 -1.8086 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -0.1163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -1.5935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7977 -0.1163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 0.8479 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 -1.2302 4.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3914 6.0903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7266 4.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3841 6.2996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8805 6.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5380 7.7524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0344 7.8570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8732 6.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2156 5.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7193 5.1606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3695 6.7181 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 2.3484 15.6050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.0707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -3.0707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3216 1.2314 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2956 -1.5877 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -0.6912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4095 1.1827 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -1.5935 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0796 -3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 -2.3403 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0692 -1.9658 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8751 0.7802 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0582 1.3609 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4744 1.7918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8190 1.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8819 4.1900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5654 3.7078 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 7.5431 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6993 8.9959 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6919 9.2052 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0544 4.0217 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0617 3.8125 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2083 5.4745 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5706 4.7745 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 5.0328 1.8972 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 0.1904 13.5210 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 0.9065 16.0185 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4704 -2.9140 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.5837 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 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 14 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 40 45 1 0 30 46 1 0 29 47 1 0 28 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 55 56 2 0 56 57 1 0 57 58 2 0 56 59 1 0 7 60 1 0 6 61 1 0 12 5 1 0 46 14 1 0 58 53 1 0 26 21 1 0 42 37 1 0 1 62 1 0 1 63 1 0 1 64 1 0 5 65 1 6 6 66 1 1 7 67 1 6 8 68 1 1 9 69 1 0 9 70 1 0 10 71 1 0 12 72 1 6 15 73 1 0 15 74 1 0 19 75 1 0 20 76 1 0 22 77 1 0 23 78 1 0 25 79 1 0 26 80 1 0 27 81 1 0 28 82 1 6 29 83 1 1 30 84 1 6 31 85 1 0 31 86 1 0 35 87 1 0 36 88 1 0 38 89 1 0 39 90 1 0 42 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 45 95 1 0 47 96 1 0 51 97 1 0 52 98 1 0 54 99 1 0 55100 1 0 57101 1 0 58102 1 0 59103 1 0 60104 1 0 61105 1 0 M END

Standard InCHIKey	LVFWZZFIRQCFMJ-DYUFTDJRSA-N
Standard InCHI	InChI=1S/C42H44O19/c1-23(44)57-39-38(53)36(51)31(20-43)58-41(39)61-42(22-56-34(49)16-8-24-3-11-27(45)12-4-24)40(59-35(50)18-9-25-5-13-28(46)14-6-25)37(52)32(60-42)21-55-33(48)17-10-26-7-15-29(47)30(19-26)54-2/h3-19,31-32,36-41,43,45-47,51-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37-,38+,39-,40+,41-,42+/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1O[C@@]1(COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O1)O)OC(=O)/C=C/c1ccc(cc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	852.25	Volume:	817.037 ? Van der Waals volume.
Dense:	1.043	LogP:	1.421 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.776 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.51 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	36.0
TPSA:	283.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.06	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.224	Fsp³:	0.333
MCE-18:	122.893 ? 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:	0.977	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.154 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.665 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.265	Promiscuous compounds:	0.196

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.177	MDCK Permeability:	-5.354
Pgp-inhibitor:	0.46	Pgp-substrate:	0.004
PAMPA:	0.972 ? 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):	0.301
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	79.391%	Volume Distribution (VD):	-0.283
Fu:	18.39% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.996
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.217
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.983
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.183 ? 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):

2.063

Half-life (T1/2):

2.77

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.4
Human Hepatotoxicity (H-HT):	0.65	Drug-induced Liver Injury (DILI):	0.9
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.656	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.13	Ototoxicity:	0.885
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.748
Genotoxicity:	0.828	RPMI-8226 Immunitoxicity:	0.183
A549 Cytotoxicity:	0.65	Hek293 Cytotoxicity:	0.913
BCF:	0.434 ? 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:	3.462 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.002 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.526 ? 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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15933032]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[18620454]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	red sea	n.a.	PMID[18656986]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[21542602]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542602]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29311	Securinega melanthesoides	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29003	Croton poilanei	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29362	Euonymus sachalinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28984	Dasymaschalon sootepense	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14557	Dictyopteris undulata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21700	Capsicum tetragonum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14557	Dictyopteris undulata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28820	Saccharum spontaneum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28984	Dasymaschalon sootepense	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29199	Lobophytum chevalieri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29379	Felicia erigeroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29188	Guatteria melosma	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29046	Tsuga mertensiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29362	Euonymus sachalinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29413	Lupinus paniculatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29311	Securinega melanthesoides	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28754	Thelephora palmata	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28666	Strychnos staudtii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29003	Croton poilanei	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28783	Dictyoloma incanescens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	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

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

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 NPC106565 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	10903
0.1-0.2	33914
0.2-0.3	4221
0.3-0.4	664
0.4-0.5	124
0.5-0.6	12
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9036	High Similarity	NPC85192
0.8929	High Similarity	NPC215095
0.7955	Intermediate Similarity	NPC3460
0.7907	Intermediate Similarity	NPC216819
0.7582	Intermediate Similarity	NPC201148
0.7444	Intermediate Similarity	NPC125823
0.7444	Intermediate Similarity	NPC7145
0.7444	Intermediate Similarity	NPC143480
0.7097	Intermediate Similarity	NPC210611
0.6897	Remote Similarity	NPC45224
0.6705	Remote Similarity	NPC28637
0.6667	Remote Similarity	NPC192763
0.6429	Remote Similarity	NPC261122
0.6364	Remote Similarity	NPC28651
0.6344	Remote Similarity	NPC262182
0.6316	Remote Similarity	NPC300262
0.6154	Remote Similarity	NPC471883
0.6042	Remote Similarity	NPC80732
0.602	Remote Similarity	NPC287615
0.602	Remote Similarity	NPC199311
0.5806	Remote Similarity	NPC484687
0.5773	Remote Similarity	NPC83743
0.5638	Remote Similarity	NPC35288
0.5591	Remote Similarity	NPC225307
0.5521	Remote Similarity	NPC471882
0.5464	Remote Similarity	NPC478887
0.5424	Remote Similarity	NPC246024
0.5361	Remote Similarity	NPC226005
0.5361	Remote Similarity	NPC476869
0.5208	Remote Similarity	NPC156692
0.5128	Remote Similarity	NPC484981
0.505	Remote Similarity	NPC476865

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4017
0.1-0.2	5056
0.2-0.3	71
0.3-0.4	6
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