NPASS Compound

Natural Product: NPC258236

Natural Product ID	NPC258236
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IFJZNZBKGRGNSP-HOCDIANWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53385591
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 40 41 0 0 0 0 0 0 0 0999 V2000 -2.1050 -2.2323 2.7206 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4187 -1.0676 3.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6439 0.0682 2.2327 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5278 0.0716 1.1951 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2096 -1.1174 0.9269 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9959 -2.2547 1.6855 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7964 1.2148 0.3614 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8570 2.0112 -0.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2554 3.1575 -0.9292 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3391 3.9102 -1.3391 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5816 3.3745 -1.2480 O 0 0 0 0 0 1 0 0 0 0 0 0 -0.5408 1.8056 0.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3424 1.0647 -0.6125 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7174 1.6974 -0.5563 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7005 0.8425 -1.3311 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5732 -0.5664 -0.7998 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1381 -0.9775 -1.1244 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9662 -2.4726 -1.0247 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2415 -2.9494 0.2507 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3213 -0.2763 -0.2787 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4945 -1.4532 -1.3174 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9925 1.3275 -1.2511 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5844 2.8869 -1.3181 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9488 -3.1407 3.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7062 -1.0261 3.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0842 0.9586 2.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9208 -1.1176 0.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5515 -3.1538 1.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8475 1.4479 0.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0171 1.1645 -1.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0694 1.9380 0.4423 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3105 0.8031 -2.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6623 -0.4739 0.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8933 -0.7039 -2.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6412 -2.9299 -1.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0648 -2.7073 -1.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0262 -2.4279 0.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1540 -0.9738 -1.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3054 1.6272 -2.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2777 2.6504 -2.2426 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 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 8 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 18 19 1 0 17 20 1 0 16 21 1 0 15 22 1 0 14 23 1 0 6 1 1 0 20 13 1 0 1 24 1 0 2 25 1 0 3 26 1 0 5 27 1 0 6 28 1 0 7 29 1 0 13 30 1 6 14 31 1 1 15 32 1 6 16 33 1 1 17 34 1 6 18 35 1 0 18 36 1 0 19 37 1 0 21 38 1 0 22 39 1 0 23 40 1 0 M CHG 1 11 -1 M END

Standard InCHIKey	IFJZNZBKGRGNSP-HOCDIANWSA-N
Standard InCHI	InChI=1S/C15H18O8/c16-7-10-11(17)12(18)13(19)15(23-10)22-9(14(20)21)6-8-4-2-1-3-5-8/h1-6,10-13,15-19H,7H2,(H,20,21)/p-1/b9-6-/t10-,11-,12+,13-,15-/m1/s1
SMILES	c1ccc(cc1)/C=C(/C(=O)[O-])O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	326.1	Volume:	308.023 ? Van der Waals volume.
Dense:	1.059	LogP:	0.03 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.887 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.292 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	14.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.341	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.633	Fsp³:	0.4
MCE-18:	48.667 ? 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:	0.322	Fluc inhibitor:	0.664 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.06 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.113 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.355	Promiscuous compounds:	0.155

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.1	MDCK Permeability:	-5.19
Pgp-inhibitor:	0.0	Pgp-substrate:	0.02
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):	0.836
20% Bioavailability (F20%):	0.458	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.226
Plasma Protein Binding (PPB):	69.931%	Volume Distribution (VD):	-0.684
Fu:	32.625% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.043
HLM stability:	0.004 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.96

Half-life (T1/2):

2.414

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.818
AMES Toxicity:	0.783	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.038	Skin Sensitization:	0.998
Carcinogencity:	0.098	Eye Corrosion:	0.002
Eye Irritation:	0.703	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.038	Ototoxicity:	0.89
Hematotoxicity:	0.337	Drug-induced Nephrotoxicity:	0.831
Genotoxicity:	0.366	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.112	Hek293 Cytotoxicity:	0.055
BCF:	0.256 ? 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:	2.743 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.963 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.184 ? 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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO27025	Erylus trisphaerus	Species	Geodiidae	Eukaryota	n.a.	Dominican	n.a.	PMID[12713417]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	New Caledonia	n.a.	PMID[15652581]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499326]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[16989517]
NPO27576	Lysiana subfalcata	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18222087]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955887]
NPO19202	Phaeolus schweinitzii	Species	Hymenochaetaceae	Eukaryota	fruits	Tibetan Plateau	n.a.	PMID[23869482]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2878063]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7130988]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	bark	n.a.	n.a.	PMID[7623034]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27215	Gracilaria textorii	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27274	Amsinckia tessellata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27696	Anolis lineatopus	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27761	Aspalathus linearis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27076	Aspergillus mutabilis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27237	Aucuba chinensis	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27419	Aurelia aurita	Species	Ulmaridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25349	Bistorta vivipara	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29217	Brickellia vernicosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27290	Carica dodecaphylla	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14449	Cedronella canariensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27470	Centaurea huber-morathii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27312	Citrus tangerina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27345	Crocus minimus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27376	Curculigo pilosa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27732	Cynometra lujae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27138	Entada rheedei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27025	Erylus trisphaerus	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27788	Eupatorium areolare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22520	Felimida luteorosea	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19173	Gleditsia caspica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27597	Haplophyllum ramosissimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27712	Helichrysum mixtum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15795	Humata pectinata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6917	Kali turgidum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27576	Lysiana subfalcata	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29241	Macaranga peltata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15868	Nostoc spongiaeforme	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27440	Osteospermum muricatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9698	Parablechnum minus	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27612	Peperomia vulcanica	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19202	Phaeolus schweinitzii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18100	Physalis edulis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27675	Platycarya strobilacea	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26912	Premna tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27525	Saussurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27815	Sia ferox	Species	Stenopelmatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27394	Sideritis euboea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27495	Sisyrinchium californicum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27640	Sorbus tianschanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27840	Stephania elegans	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26882	Swertia swertopsis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27453	Trichoderma koningi	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27050	Tsuga chinensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27800	Usnea undulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27254	Utricularia australis	Species	Lentibulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27099	Virgilia divaricata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27675	Platycarya strobilacea	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27376	Curculigo pilosa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27640	Sorbus tianschanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27237	Aucuba chinensis	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27612	Peperomia vulcanica	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27376	Curculigo pilosa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27840	Stephania elegans	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27675	Platycarya strobilacea	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9698	Parablechnum minus	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27640	Sorbus tianschanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30034	Onobrychis vicllfolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27675	Platycarya strobilacea	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27640	Sorbus tianschanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27761	Aspalathus linearis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2046	Cathormion altissimum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27495	Sisyrinchium californicum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7608	Phelline lucida	Species	Phellinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13192	Chara ceratophylla	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27215	Gracilaria textorii	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16013	Inga velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29217	Brickellia vernicosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27312	Citrus tangerina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27612	Peperomia vulcanica	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12035	Rhododendron ungerni	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20585	Urochloa decumbens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16306	Curcuma caesia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13683	Cosmos diversifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15795	Humata pectinata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9698	Parablechnum minus	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27470	Centaurea huber-morathii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27138	Entada rheedei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22520	Felimida luteorosea	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9342	Solenopsis punctaticeps	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27237	Aucuba chinensis	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27254	Utricularia australis	Species	Lentibulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO206	Ormosia nobilis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6917	Kali turgidum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18100	Physalis edulis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27675	Platycarya strobilacea	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11046	Ocimum pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27099	Virgilia divaricata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27376	Curculigo pilosa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27050	Tsuga chinensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19202	Phaeolus schweinitzii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27440	Osteospermum muricatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19173	Gleditsia caspica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27597	Haplophyllum ramosissimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27788	Eupatorium areolare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27525	Saussurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25349	Bistorta vivipara	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27732	Cynometra lujae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14449	Cedronella canariensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27345	Crocus minimus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15868	Nostoc spongiaeforme	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29241	Macaranga peltata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27025	Erylus trisphaerus	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27815	Sia ferox	Species	Stenopelmatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12207	Lagochilus leiacanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27640	Sorbus tianschanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27696	Anolis lineatopus	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10928	Xenia obscuronata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3059	Erythrina pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27274	Amsinckia tessellata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27394	Sideritis euboea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27290	Carica dodecaphylla	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27419	Aurelia aurita	Species	Ulmaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO875	Cryptocarya oblata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12557	Strychnos tricalysioides	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27076	Aspergillus mutabilis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26912	Premna tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27576	Lysiana subfalcata	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1398	Trichodesma incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27840	Stephania elegans	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27712	Helichrysum mixtum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27800	Usnea undulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26882	Swertia swertopsis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27453	Trichoderma koningi	Species	Hypocreaceae	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 NPC258236 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	22444
0.1-0.2	23901
0.2-0.3	3018
0.3-0.4	459
0.4-0.5	33
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC601241
0.8	Intermediate Similarity	NPC606576
0.5455	Remote Similarity	NPC306255
0.5094	Remote Similarity	NPC152384

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4396
0.1-0.2	4572
0.2-0.3	162
0.3-0.4	17
0.4-0.5	3
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