NPASS Compound

Natural Product: NPC22519

Natural Product ID	NPC22519
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Hydroxy-5,7-Dimethoxy-2-(4-Methoxyphenyl)Chromen-4-One
IUPAC Name	6-hydroxy-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms	NSC-53907
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL77695
PubChem CID	243760
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

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 42 0 0 0 0 0 0 0 0999 V2000 6.9581 -0.3152 -0.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2241 -1.0612 0.8041 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8355 -0.9246 0.7980 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1907 -0.0966 -0.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8207 0.0315 -0.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0467 -0.6666 0.8053 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6603 -1.4940 1.7016 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0558 -1.6204 1.6949 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5927 -0.5102 0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2247 -1.1788 1.6459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6127 -1.0021 1.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3505 -1.6367 2.4081 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0933 -0.1339 0.6531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2212 0.5312 -0.2078 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7623 1.3966 -1.1414 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1197 1.5960 -1.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9442 0.9280 -0.3605 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4650 0.0432 0.6023 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 -0.6341 1.4724 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7934 -1.8934 1.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3106 1.1283 -0.4387 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6229 2.4677 -2.1633 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8226 3.1817 -3.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 0.3221 -0.1098 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0145 -0.7152 -0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5868 -0.4813 -1.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0314 0.7377 0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8088 0.4560 -0.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3731 0.7093 -0.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1240 -2.0784 2.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5531 -2.2732 2.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 -1.8617 2.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0813 1.9061 -1.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7398 -1.7134 0.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0217 -2.5344 1.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0895 -2.4251 0.4274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7334 1.6947 0.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2017 2.4920 -3.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4349 3.7639 -3.7788 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1682 3.8645 -2.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 17 21 1 0 16 22 1 0 22 23 1 0 14 24 1 0 8 3 1 0 24 9 1 0 18 13 1 0 1 25 1 0 1 26 1 0 1 27 1 0 4 28 1 0 5 29 1 0 7 30 1 0 8 31 1 0 10 32 1 0 15 33 1 0 20 34 1 0 20 35 1 0 20 36 1 0 21 37 1 0 23 38 1 0 23 39 1 0 23 40 1 0 M END

Standard InCHIKey	XYHIVQHSXGOAQP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)13-8-12(19)16-14(24-13)9-15(22-2)17(20)18(16)23-3/h4-9,20H,1-3H3
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c2OC)O)OC)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	328.09	Volume:	325.865 ? Van der Waals volume.
Dense:	1.007	LogP:	2.37 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.623 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.015 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	18.0
TPSA:	78.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.792	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.231	Fsp³:	0.167
MCE-18:	18.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.265	Fluc inhibitor:	0.977 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.887 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.695 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.346	Promiscuous compounds:	0.69

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962	MDCK Permeability:	-4.672
Pgp-inhibitor:	0.953	Pgp-substrate:	0.15
PAMPA:	0.044 ? 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):	0.251
20% Bioavailability (F20%):	0.344	30% Bioavailability (F30%):	0.446
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.934
Plasma Protein Binding (PPB):	92.48%	Volume Distribution (VD):	-0.536
Fu:	5.439% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.995
BSEP inhibitor:	0.981

ADMET: Metabolism

CYP1A2-inhibitor:	0.881	CYP1A2-substrate:	0.576
CYP2C19-inhibitor:	0.014	CYP2C19-substrate:	0.24
CYP2C9-inhibitor:	0.958	CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	0.961
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.489
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.937 ? 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):

7.442

Half-life (T1/2):

1.145

ADMET: Toxicity

hERG Blockers:	0.163	hERG Blockers (10um):	0.492
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.882
AMES Toxicity:	0.552	Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.576	Skin Sensitization:	0.383
Carcinogencity:	0.813	Eye Corrosion:	0.409
Eye Irritation:	0.978	Respiratory Toxicity:	0.783
Drug-induced Neurotoxicity:	0.337	Ototoxicity:	0.149
Hematotoxicity:	0.306	Drug-induced Nephrotoxicity:	0.201
Genotoxicity:	0.334	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.443
BCF:	1.11 ? 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:	3.644 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.751 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.093 ? 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
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32933154]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33081385]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34847783]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36671383]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202742]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	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

Activity Type	# Activity
Inhibition	1
GI50	59

Activity Type	# Activity
Individual protein	1
Cell line	59

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	4.24	%	PMID[17287127]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	43000.0	nM	PMID[9632366]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	26915.35	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	47315.13	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	48528.85	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	30549.21	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	30690.22	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	20941.12	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	51999.6	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	77446.18	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	49317.38	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	96161.23	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	23442.29	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	52360.04	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	29991.63	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	34040.82	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	38106.58	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	59292.53	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	29107.17	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	63095.73	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	56623.93	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	23550.49	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	58748.94	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	28313.92	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	73790.42	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	54325.03	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	17906.06	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	58344.51	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	27797.13	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	42756.29	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	40364.54	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	36897.76	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	55335.01	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	57147.86	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	42461.96	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	21827.3	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	46989.41	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	46773.51	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	34994.52	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	91411.32	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	42657.95	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	50815.94	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	50699.07	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	23067.47	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	30760.97	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	32809.53	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	85506.67	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	42364.3	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	30831.88	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	33036.95	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	40364.54	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	36057.86	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	47424.2	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	38370.72	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	69984.2	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	35481.34	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	36643.76	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	48977.88	nM	PubChem BioAssay data set

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 NPC22519 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	29103
0.1-0.2	17394
0.2-0.3	2565
0.3-0.4	571
0.4-0.5	168
0.5-0.6	45
0.6-0.7	7
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
0.6727	Remote Similarity	NPC57030
0.6604	Remote Similarity	NPC101294
0.6481	Remote Similarity	NPC14958
0.625	Remote Similarity	NPC29353
0.614	Remote Similarity	NPC145379
0.6111	Remote Similarity	NPC604293
0.6034	Remote Similarity	NPC603827
0.5965	Remote Similarity	NPC156222
0.5862	Remote Similarity	NPC184136
0.5862	Remote Similarity	NPC231772
0.5862	Remote Similarity	NPC266597
0.5862	Remote Similarity	NPC604085
0.5833	Remote Similarity	NPC608258
0.5763	Remote Similarity	NPC603662
0.569	Remote Similarity	NPC274327
0.5593	Remote Similarity	NPC250266
0.5593	Remote Similarity	NPC610660
0.5536	Remote Similarity	NPC40818
0.5439	Remote Similarity	NPC2771
0.5439	Remote Similarity	NPC278556
0.5424	Remote Similarity	NPC488084
0.5424	Remote Similarity	NPC275722
0.5424	Remote Similarity	NPC52611
0.5424	Remote Similarity	NPC600177
0.541	Remote Similarity	NPC212678
0.5397	Remote Similarity	NPC295036
0.5357	Remote Similarity	NPC41721
0.5345	Remote Similarity	NPC129680
0.5333	Remote Similarity	NPC70853
0.5333	Remote Similarity	NPC176775
0.5333	Remote Similarity	NPC198826
0.5333	Remote Similarity	NPC604462
0.5323	Remote Similarity	NPC287101
0.5323	Remote Similarity	NPC283600
0.5323	Remote Similarity	NPC223579
0.5246	Remote Similarity	NPC604569
0.5238	Remote Similarity	NPC606105
0.5172	Remote Similarity	NPC284424
0.5172	Remote Similarity	NPC106461
0.5167	Remote Similarity	NPC125887
0.5167	Remote Similarity	NPC127447
0.5167	Remote Similarity	NPC215932
0.5167	Remote Similarity	NPC47815
0.5167	Remote Similarity	NPC194281
0.5167	Remote Similarity	NPC609062
0.5082	Remote Similarity	NPC48479
0.5082	Remote Similarity	NPC276905
0.5082	Remote Similarity	NPC234133
0.5079	Remote Similarity	NPC160951
0.5079	Remote Similarity	NPC195202
0.5077	Remote Similarity	NPC485299
0.5072	Remote Similarity	NPC280975

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5100
0.1-0.2	3924
0.2-0.3	119
0.3-0.4	5
0.4-0.5	2
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