NPASS Compound

Natural Product: NPC303668

Natural Product ID	NPC303668
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BDCDNTVZSILEOY-FWYGIPPASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11968848
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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

Chemical Representations

RDKit 3D 49 52 0 0 0 0 0 0 0 0999 V2000 0.5679 2.5206 0.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5762 3.8961 0.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5179 4.4649 -0.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 3.6390 -1.1254 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4269 2.2842 -0.8915 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4811 1.6699 -0.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4944 0.2296 0.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4864 -0.5426 0.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 -1.9210 0.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2728 -2.6375 1.0229 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8470 -2.4594 0.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0001 -3.8389 0.3153 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1863 -4.4050 -0.0613 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1963 -3.5878 -0.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0511 -2.2254 -0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8545 -1.6389 -0.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6401 -0.3666 -0.2845 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4013 -4.1705 -0.9003 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 -4.6018 0.7910 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7477 -0.0395 0.9056 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8322 0.0325 -0.0035 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6131 1.2821 0.1961 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0378 0.7497 0.0548 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8490 -0.5549 0.8346 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9602 -1.5316 0.5250 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6058 -2.7639 1.0708 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6928 -1.0407 0.2611 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8737 1.5523 0.8189 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4364 2.2300 -0.8007 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4194 4.1973 -1.9573 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.8372 -0.7483 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1534 2.1028 1.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1713 4.5151 0.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1753 1.6573 -1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3235 -5.4584 -0.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8213 -1.5642 -0.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9745 -3.7336 -1.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1289 -5.1596 1.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -0.0706 -1.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4823 1.7698 1.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3479 0.6040 -0.9717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7452 -0.3356 1.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9270 -1.2251 0.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0585 -1.6679 -0.5620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8686 -3.4991 0.4421 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3838 2.0376 1.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2392 2.8403 -0.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2350 4.6172 -1.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3559 6.3102 -1.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 4 30 1 0 3 31 1 0 6 1 1 0 17 7 1 0 27 21 1 0 16 11 1 0 1 32 1 0 2 33 1 0 5 34 1 0 13 35 1 0 15 36 1 0 18 37 1 0 19 38 1 0 21 39 1 6 22 40 1 1 23 41 1 6 24 42 1 1 25 43 1 0 25 44 1 0 26 45 1 0 28 46 1 0 29 47 1 0 30 48 1 0 31 49 1 0 M END

Standard InCHIKey	BDCDNTVZSILEOY-FWYGIPPASA-N
Standard InCHI	InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	434.08	Volume:	395.851 ? Van der Waals volume.
Dense:	1.097	LogP:	0.812 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.098 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.636 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.836	Fsp³:	0.25
MCE-18:	86.32 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.675	Fluc inhibitor:	0.305 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.953 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.547 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.297	Promiscuous compounds:	0.921

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.242	MDCK Permeability:	-4.986
Pgp-inhibitor:	0.0	Pgp-substrate:	0.212
PAMPA:	0.957 ? 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):	0.078
20% Bioavailability (F20%):	0.597	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.063
Plasma Protein Binding (PPB):	85.014%	Volume Distribution (VD):	-0.02
Fu:	14.264% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.896
BSEP inhibitor:	0.078

ADMET: Metabolism

CYP1A2-inhibitor:	0.021	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.075	CYP2D6-substrate:	0.944
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.797 ? 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):

4.679

Half-life (T1/2):

2.763

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.205
Human Hepatotoxicity (H-HT):	0.54	Drug-induced Liver Injury (DILI):	0.898
AMES Toxicity:	0.745	Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.332	Skin Sensitization:	0.998
Carcinogencity:	0.221	Eye Corrosion:	0.002
Eye Irritation:	0.974	Respiratory Toxicity:	0.223
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.726
Hematotoxicity:	0.053	Drug-induced Nephrotoxicity:	0.046
Genotoxicity:	0.911	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.871	Hek293 Cytotoxicity:	0.533
BCF:	0.707 ? 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:	3.353 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.616 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.97 ? 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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO12926	Dendrospora tenella	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10217713]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21875046]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	whole plant	Taitung County, Taiwan	2009-MAY	PMID[21875046]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27715048]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12926	Dendrospora tenella	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11384	Tibouchina semidecandra	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20658	Lonicera caerulea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13415	Securigera coronilla	Species	Romaleidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10422	Penicillium thymicola	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6238	Pseudo-nitzschia multiseries	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12431	Cytospora rhizophorae	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12771	Eucalyptus alba	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13919	Agathis microstachya	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7310	Corchorus trilocularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10049	Coleophoma empetri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13091	Helianthus ciliaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13415	Securigera coronilla	Species	Romaleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12771	Eucalyptus alba	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13625	Salacia beddomei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11384	Tibouchina semidecandra	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28041	Scaevola taccada	Species	Goodeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13518	Senecio stabianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20658	Lonicera caerulea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10422	Penicillium thymicola	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12431	Cytospora rhizophorae	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13919	Agathis microstachya	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12245	Lasiosiphon burchellii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6238	Pseudo-nitzschia multiseries	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9097	Solanum hypomalacophyllum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4425	Delphinium honanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7310	Corchorus trilocularis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12926	Dendrospora tenella	Species	n.a.	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 NPC303668 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	22211
0.1-0.2	24180
0.2-0.3	2406
0.3-0.4	560
0.4-0.5	223
0.5-0.6	74
0.6-0.7	76
0.7-0.8	0
0.8-0.85	11
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67037
1.0	High Similarity	NPC255615
0.8955	High Similarity	NPC145038
0.8955	High Similarity	NPC56077
0.8955	High Similarity	NPC281131
0.8955	High Similarity	NPC253662
0.8955	High Similarity	NPC179950
0.8955	High Similarity	NPC88789
0.8955	High Similarity	NPC491374
0.8923	High Similarity	NPC288084
0.8636	High Similarity	NPC34531
0.8	Intermediate Similarity	NPC127546
0.8	Intermediate Similarity	NPC57625
0.8	Intermediate Similarity	NPC77672
0.8	Intermediate Similarity	NPC133671
0.8	Intermediate Similarity	NPC135391
0.8	Intermediate Similarity	NPC173637
0.8	Intermediate Similarity	NPC78263
0.8	Intermediate Similarity	NPC317489
0.8	Intermediate Similarity	NPC250069
0.8	Intermediate Similarity	NPC223424
0.8	Intermediate Similarity	NPC600591
0.7895	Intermediate Similarity	NPC29958
0.7792	Intermediate Similarity	NPC471748
0.7746	Intermediate Similarity	NPC19388
0.7746	Intermediate Similarity	NPC240431
0.7746	Intermediate Similarity	NPC55786
0.7568	Intermediate Similarity	NPC175107
0.7468	Intermediate Similarity	NPC156869
0.7468	Intermediate Similarity	NPC605592
0.7397	Intermediate Similarity	NPC64305
0.7333	Intermediate Similarity	NPC60735
0.7333	Intermediate Similarity	NPC26230
0.7324	Intermediate Similarity	NPC276222
0.7324	Intermediate Similarity	NPC274618
0.7324	Intermediate Similarity	NPC118284
0.7324	Intermediate Similarity	NPC608147
0.7273	Intermediate Similarity	NPC203050
0.7273	Intermediate Similarity	NPC225434
0.7237	Intermediate Similarity	NPC120099
0.72	Intermediate Similarity	NPC472459
0.7179	Intermediate Similarity	NPC254855
0.7179	Intermediate Similarity	NPC116864
0.7179	Intermediate Similarity	NPC244776
0.7179	Intermediate Similarity	NPC94610
0.7123	Intermediate Similarity	NPC111929
0.7123	Intermediate Similarity	NPC320283
0.7123	Intermediate Similarity	NPC41121
0.7067	Intermediate Similarity	NPC52550
0.7	Intermediate Similarity	NPC139320
0.6974	Remote Similarity	NPC42773
0.6974	Remote Similarity	NPC45522
0.6974	Remote Similarity	NPC325555
0.6974	Remote Similarity	NPC226304
0.6933	Remote Similarity	NPC136042
0.6914	Remote Similarity	NPC67326
0.6892	Remote Similarity	NPC135599
0.6892	Remote Similarity	NPC73855
0.6892	Remote Similarity	NPC113968
0.6892	Remote Similarity	NPC328940
0.6892	Remote Similarity	NPC277174
0.6892	Remote Similarity	NPC606877
0.6883	Remote Similarity	NPC159579
0.6867	Remote Similarity	NPC154741
0.6829	Remote Similarity	NPC203259
0.6829	Remote Similarity	NPC33054
0.6829	Remote Similarity	NPC155877
0.6829	Remote Similarity	NPC176740
0.6829	Remote Similarity	NPC471725
0.6829	Remote Similarity	NPC134532
0.6829	Remote Similarity	NPC602582
0.6795	Remote Similarity	NPC609478
0.6753	Remote Similarity	NPC599850
0.6747	Remote Similarity	NPC255157
0.6747	Remote Similarity	NPC259896
0.6667	Remote Similarity	NPC235260
0.6667	Remote Similarity	NPC182121
0.6667	Remote Similarity	NPC155763
0.6667	Remote Similarity	NPC476771
0.6615	Remote Similarity	NPC286342
0.6585	Remote Similarity	NPC476773
0.6552	Remote Similarity	NPC135831
0.6552	Remote Similarity	NPC471669
0.6543	Remote Similarity	NPC95866
0.6512	Remote Similarity	NPC37668
0.65	Remote Similarity	NPC223747
0.65	Remote Similarity	NPC605784
0.6486	Remote Similarity	NPC54802
0.6486	Remote Similarity	NPC197304
0.6484	Remote Similarity	NPC292019
0.6484	Remote Similarity	NPC202908
0.6471	Remote Similarity	NPC253521
0.6471	Remote Similarity	NPC113836
0.6456	Remote Similarity	NPC219904
0.6456	Remote Similarity	NPC488071
0.642	Remote Similarity	NPC170052
0.642	Remote Similarity	NPC135846
0.641	Remote Similarity	NPC84362
0.6375	Remote Similarity	NPC224530
0.6364	Remote Similarity	NPC254306
0.6282	Remote Similarity	NPC8573
0.6282	Remote Similarity	NPC297987
0.6282	Remote Similarity	NPC265530
0.6279	Remote Similarity	NPC296018
0.6222	Remote Similarity	NPC223426
0.6203	Remote Similarity	NPC305811
0.6203	Remote Similarity	NPC488080
0.6203	Remote Similarity	NPC169977
0.619	Remote Similarity	NPC471079
0.6154	Remote Similarity	NPC81042
0.6154	Remote Similarity	NPC476772
0.6118	Remote Similarity	NPC173582
0.6118	Remote Similarity	NPC470405
0.6118	Remote Similarity	NPC265885
0.6118	Remote Similarity	NPC181465
0.6118	Remote Similarity	NPC215710
0.6118	Remote Similarity	NPC163242
0.6118	Remote Similarity	NPC272068
0.6118	Remote Similarity	NPC473438
0.6118	Remote Similarity	NPC253788
0.6098	Remote Similarity	NPC209023
0.6049	Remote Similarity	NPC129217
0.6047	Remote Similarity	NPC304741
0.6023	Remote Similarity	NPC245452
0.6	Remote Similarity	NPC480466
0.6	Remote Similarity	NPC271692
0.5977	Remote Similarity	NPC129264
0.5977	Remote Similarity	NPC35167
0.5976	Remote Similarity	NPC85707
0.5955	Remote Similarity	NPC122467
0.5955	Remote Similarity	NPC270448
0.5955	Remote Similarity	NPC104883
0.5955	Remote Similarity	NPC488679
0.593	Remote Similarity	NPC39834
0.5926	Remote Similarity	NPC216496
0.5909	Remote Similarity	NPC61904
0.5909	Remote Similarity	NPC470125
0.5909	Remote Similarity	NPC488073
0.5909	Remote Similarity	NPC153755
0.5904	Remote Similarity	NPC116458
0.5904	Remote Similarity	NPC246943
0.5889	Remote Similarity	NPC205824
0.5851	Remote Similarity	NPC189564
0.5833	Remote Similarity	NPC476215
0.5824	Remote Similarity	NPC76831
0.5824	Remote Similarity	NPC89127
0.5802	Remote Similarity	NPC24043
0.5802	Remote Similarity	NPC27640
0.5795	Remote Similarity	NPC144097
0.5789	Remote Similarity	NPC219043
0.5783	Remote Similarity	NPC101026
0.5783	Remote Similarity	NPC259957
0.5783	Remote Similarity	NPC488077
0.5783	Remote Similarity	NPC189913
0.5783	Remote Similarity	NPC197285
0.5783	Remote Similarity	NPC601710
0.575	Remote Similarity	NPC289667
0.575	Remote Similarity	NPC143851
0.5745	Remote Similarity	NPC203145
0.5735	Remote Similarity	NPC103342
0.5732	Remote Similarity	NPC138927
0.5732	Remote Similarity	NPC21100
0.5714	Remote Similarity	NPC97119
0.57	Remote Similarity	NPC156785
0.5679	Remote Similarity	NPC282987
0.5667	Remote Similarity	NPC297503
0.5663	Remote Similarity	NPC191306
0.5663	Remote Similarity	NPC48093
0.5652	Remote Similarity	NPC476472
0.5652	Remote Similarity	NPC294815
0.5652	Remote Similarity	NPC85751
0.5652	Remote Similarity	NPC16194
0.5652	Remote Similarity	NPC19240
0.5652	Remote Similarity	NPC220173
0.5638	Remote Similarity	NPC214621
0.5638	Remote Similarity	NPC34267
0.5632	Remote Similarity	NPC609888
0.5612	Remote Similarity	NPC470718
0.5604	Remote Similarity	NPC473327
0.5595	Remote Similarity	NPC484158
0.5591	Remote Similarity	NPC292929
0.5567	Remote Similarity	NPC470712
0.5567	Remote Similarity	NPC303694
0.5556	Remote Similarity	NPC249281
0.5556	Remote Similarity	NPC104677
0.5556	Remote Similarity	NPC488074
0.5542	Remote Similarity	NPC59534
0.5532	Remote Similarity	NPC602448
0.5529	Remote Similarity	NPC206123
0.5506	Remote Similarity	NPC473862
0.5495	Remote Similarity	NPC75574
0.5488	Remote Similarity	NPC277205
0.5488	Remote Similarity	NPC37919
0.5488	Remote Similarity	NPC609879
0.5464	Remote Similarity	NPC48984
0.5455	Remote Similarity	NPC78697
0.5422	Remote Similarity	NPC46420
0.5402	Remote Similarity	NPC265115
0.5393	Remote Similarity	NPC196127
0.5385	Remote Similarity	NPC126784

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC303668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5653
0.1-0.2	3424
0.2-0.3	62
0.3-0.4	4
0.4-0.5	5
0.5-0.6	1
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	Drug ID	Developmental Stage
0.6829	Remote Similarity	NPD6797	Phase 2
0.5158	Remote Similarity	NPD7251	Phase 2

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