NPASS Compound

Natural Product: NPC63027

Natural Product ID	NPC63027
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CLWOXNLVWMXBRD-QGZVFWFLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

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 46 48 0 0 0 0 0 0 0 0999 V2000 0.2935 -3.5243 0.9983 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3432 -2.5651 -0.1239 N 0 0 0 0 0 4 0 0 0 0 0 0 -0.3019 -3.2998 -1.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 -2.4177 -0.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -1.1935 -1.4415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6101 -0.0299 -0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4131 1.0857 -0.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1138 2.1120 0.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0384 2.0151 1.2333 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2323 0.8915 1.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5138 -0.1533 0.3045 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3259 -1.3651 0.2286 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5073 -1.0636 -0.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1735 0.2110 -0.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1995 0.2192 0.6777 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8210 1.3872 1.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4334 2.5975 0.5336 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4161 2.6171 -0.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8032 1.4336 -0.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0469 3.7914 0.9126 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7865 3.0698 2.1046 O 0 0 0 0 0 1 0 0 0 0 0 0 2.9313 3.2183 0.4225 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0531 3.3532 -0.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6942 -4.0669 0.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0676 -4.2898 0.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3514 -3.0229 1.9668 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3059 -4.2423 -1.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3438 -2.7577 -2.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3082 -3.6210 -0.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3928 -2.2125 0.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 -3.3268 -1.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8911 -1.1761 -1.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1372 -1.1986 -2.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2528 1.1288 -1.1565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6200 0.8230 1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7753 -1.4911 1.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2506 -1.8605 -0.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1874 -0.9591 -1.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4891 -0.7402 1.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6195 1.3706 1.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1240 3.5751 -0.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9951 1.4385 -1.5100 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0162 3.9936 0.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9212 2.7633 -0.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8121 3.0684 -1.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3839 4.4138 -0.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 9 21 1 0 8 22 1 0 22 23 1 0 12 2 1 0 19 14 1 0 11 6 1 0 1 24 1 0 1 25 1 0 1 26 1 0 3 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 7 34 1 0 10 35 1 0 12 36 1 1 13 37 1 0 13 38 1 0 15 39 1 0 16 40 1 0 18 41 1 0 19 42 1 0 20 43 1 0 23 44 1 0 23 45 1 0 23 46 1 0 M CHG 2 2 1 21 -1 M END

Standard InCHIKey	CLWOXNLVWMXBRD-QGZVFWFLSA-N
Standard InCHI	InChI=1S/C19H23NO3/c1-20(2)9-8-14-11-19(23-3)18(22)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17H,8-10H2,1-3H3,(H-,21,22)/t17-/m1/s1
SMILES	C[N+]1(C)CCc2cc(c(cc2[C@H]1Cc1ccc(cc1)O)[O-])OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	313.17	Volume:	333.059 ? Van der Waals volume.
Dense:	0.94	LogP:	0.284 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.38 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	17.0
TPSA:	52.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.885	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.631	Fsp³:	0.368
MCE-18:	61.385 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.773	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.281 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.032 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.039	Promiscuous compounds:	0.12

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.382	MDCK Permeability:	-4.709
Pgp-inhibitor:	0.002	Pgp-substrate:	0.999
PAMPA:	0.339 ? 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):	0.594
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.417
Plasma Protein Binding (PPB):	34.765%	Volume Distribution (VD):	-0.236
Fu:	60.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.903
OATP1B3 inhibitor:	0.766	BCRP inhibitor:	0.249
BSEP inhibitor:	0.127

ADMET: Metabolism

CYP1A2-inhibitor:	0.997	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.353	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.293
CYP2B6-substrate:	0.315	CYP2C8-inhibitor:	0.0
HLM stability:	0.425 ? 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):

3.119

Half-life (T1/2):

2.754

ADMET: Toxicity

hERG Blockers:	0.219	hERG Blockers (10um):	0.292
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.141	Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.981	Skin Sensitization:	0.687
Carcinogencity:	0.307	Eye Corrosion:	0.065
Eye Irritation:	0.984	Respiratory Toxicity:	0.957
Drug-induced Neurotoxicity:	0.82	Ototoxicity:	0.179
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.068
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.327
BCF:	1.938 ? 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:	4.465 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.349 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.449 ? 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
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479314]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650079]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	stems	n.a.	n.a.	PMID[1517737]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15577228]
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[15969497]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441070]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[18175990]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085682]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672802]
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27057812]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO6698	Euphorbia pithyusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28671832]
NPO25118	Centaurea benedicta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39771277]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[9987830]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2568	Posidonia oceanica	Species	Posidoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3482	Alpinia flabellata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12018	Alternaria bataticola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10905	Baccharis truncata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18026	Bipolaris sacchari	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7009	Callyspongia spinosissima	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25118	Centaurea benedicta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27148	Chuquiraga erinacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11592	Cuphea hyssopifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5998	Echinoclathria subhispida	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13617	Eria rigida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17166	Euphorbia palustris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6698	Euphorbia pithyusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4282	Fouquieria diguetii	Species	Fouquieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2680	Holothuria squamifera	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15992	Hypogymnia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14194	Mamestra brassicae	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11246	Ononis viscosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8721	Parectatosoma mocquerysi	Species	Anisacanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15514	Pedicularis rex	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO273	Phyllobates bicolor	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2043	Pseudocyphellaria coronata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9538	Pterocarpus erinaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10048	Pyrus bourgaeana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14329	Sigillina signifera	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17358	Sorbus torminalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2070	Thioalkalivibrio versutus	Species	Ectothiorhodospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14455	Triunia erythrocarpa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3482	Alpinia flabellata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17166	Euphorbia palustris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14194	Mamestra brassicae	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8721	Parectatosoma mocquerysi	Species	Anisacanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6698	Euphorbia pithyusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15514	Pedicularis rex	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25118	Centaurea benedicta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14329	Sigillina signifera	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12018	Alternaria bataticola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11592	Cuphea hyssopifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4282	Fouquieria diguetii	Species	Fouquieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2680	Holothuria squamifera	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10905	Baccharis truncata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10532	Pinus edulis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5998	Echinoclathria subhispida	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2568	Posidonia oceanica	Species	Posidoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9133	Lathyrus latifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13617	Eria rigida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2043	Pseudocyphellaria coronata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9538	Pterocarpus erinaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15992	Hypogymnia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17358	Sorbus torminalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10048	Pyrus bourgaeana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27148	Chuquiraga erinacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO273	Phyllobates bicolor	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11246	Ononis viscosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14455	Triunia erythrocarpa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18026	Bipolaris sacchari	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17166	Euphorbia palustris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3482	Alpinia flabellata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7009	Callyspongia spinosissima	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2070	Thioalkalivibrio versutus	Species	Ectothiorhodospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13018	Thelephora aurantiotincta	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13465	Salvia broussonetii	Species	Lamiaceae	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 NPC63027 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	27920
0.1-0.2	18675
0.2-0.3	3093
0.3-0.4	153
0.4-0.5	12
0.5-0.6	4
0.6-0.7	1
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	Natural Product ID
0.7037	Intermediate Similarity	NPC484288
0.614	Remote Similarity	NPC606321
0.5965	Remote Similarity	NPC476151
0.5849	Remote Similarity	NPC484286
0.5574	Remote Similarity	NPC600791
0.5333	Remote Similarity	NPC216252

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC63027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5193
0.1-0.2	3814
0.2-0.3	135
0.3-0.4	6
0.4-0.5	0
0.5-0.6	2
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
0.5143	Remote Similarity	NPD8252	Phase 4
0.507	Remote Similarity	NPD8251	Approved

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