NPASS Compound

Natural Product: NPC160499

Natural Product ID	NPC160499
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nepodin
IUPAC Name	1-(1,8-dihydroxy-3-methylnaphthalen-2-yl)ethanone
Synonyms	Nepodin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508681
PubChem CID	100780
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

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 28 29 0 0 0 0 0 0 0 0999 V2000 1.8375 2.4632 0.1737 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8319 1.3736 0.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4722 1.6655 0.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4685 0.7135 0.3703 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7770 0.9920 0.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7643 0.0176 0.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4206 -1.2542 0.2369 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1248 -1.5524 -0.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1313 -0.5680 -0.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1661 -0.8803 -0.3833 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1376 0.0932 -0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4979 -0.2402 -0.6805 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8561 -0.1003 -1.8776 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4941 -0.7421 0.3011 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -2.1875 -0.7823 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7823 -2.8336 -0.5136 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3479 3.4023 -0.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6911 2.2920 -0.5316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2195 2.4942 1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7253 2.6735 0.7443 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9850 2.0086 1.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7836 0.2513 0.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1587 -2.0418 0.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6059 -1.8616 0.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2484 -0.4167 1.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4862 -0.3326 0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5404 -2.4337 -1.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7829 -2.9956 -1.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 10 15 1 0 8 16 1 0 11 2 1 0 9 4 1 0 1 17 1 0 1 18 1 0 1 19 1 0 3 20 1 0 5 21 1 0 6 22 1 0 7 23 1 0 14 24 1 0 14 25 1 0 14 26 1 0 15 27 1 0 16 28 1 0 M END

Standard InCHIKey	DMLHPCALHMPJHS-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C13H12O3/c1-7-6-9-4-3-5-10(15)12(9)13(16)11(7)8(2)14/h3-6,15-16H,1-2H3
SMILES	Cc1cc2cccc(c2c(c1C(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	216.08	Volume:	226.843 ? Van der Waals volume.
Dense:	0.953	LogP:	2.736 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.863 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.501 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	12.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.72	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.25	Fsp³:	0.154
MCE-18:	13.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.279	Fluc inhibitor:	0.041 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.36 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.043 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.907	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.94	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.009	Pgp-substrate:	0.055
PAMPA:	0.604 ? 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):	0.016
20% Bioavailability (F20%):	0.279	30% Bioavailability (F30%):	0.385
50% Bioavailability (F50%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146	MRP1:	0.781
Plasma Protein Binding (PPB):	97.189%	Volume Distribution (VD):	-0.443
Fu:	2.549% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.015
BSEP inhibitor:	0.057

ADMET: Metabolism

CYP1A2-inhibitor:	0.953	CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.464	CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.923	CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.486	CYP3A4-substrate:	0.099
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.825
HLM stability:	0.979 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.205

Half-life (T1/2):

1.147

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.471
Human Hepatotoxicity (H-HT):	0.545	Drug-induced Liver Injury (DILI):	0.568
AMES Toxicity:	0.679	Rat Oral Acute Toxicity:	0.273
Maximum Recommended Daily Dose:	0.408	Skin Sensitization:	0.818
Carcinogencity:	0.465	Eye Corrosion:	0.09
Eye Irritation:	0.993	Respiratory Toxicity:	0.937
Drug-induced Neurotoxicity:	0.266	Ototoxicity:	0.284
Hematotoxicity:	0.397	Drug-induced Nephrotoxicity:	0.523
Genotoxicity:	0.439	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.384	Hek293 Cytotoxicity:	0.361
BCF:	0.827 ? 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:	3.728 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.385 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.067 ? 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
NPO5532	Staurocucumis liouvillei	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421733]
NPO4573	Mortierella alpina	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12191843]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738395]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32092043]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36866384]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37151483]
NPO62756	Rumex balcanicus	Genus	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39373260]
NPO4057	Picrolemma pseudocoffea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[6533270]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090874]
NPO4573	Mortierella alpina	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9668087]
NPO4573	Mortierella alpina	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20186	Xanthomonas campestris	Species	Xanthomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4057	Picrolemma pseudocoffea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22261	Primula rosea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21887	Artemisia hugueti	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO324	Dianella nigra	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5532	Staurocucumis liouvillei	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21718	Ligularia clivorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23235	Zanthoxylum arnottianum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21718	Ligularia clivorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23235	Zanthoxylum arnottianum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20960	Anchistea virginica	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO324	Dianella nigra	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21718	Ligularia clivorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4573	Mortierella alpina	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20960	Anchistea virginica	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5755	Bauhinia glauca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20186	Xanthomonas campestris	Species	Xanthomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6176	Ramichloridium apiculatum	Species	Dissoconiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23235	Zanthoxylum arnottianum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19239	Rumex palustris	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5532	Staurocucumis liouvillei	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO145	Chondropetalum andreaeanum	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4057	Picrolemma pseudocoffea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21514	Glandularia x hybrida	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22656	Dineutus assimilis	Species	Gyrinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22261	Primula rosea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21887	Artemisia hugueti	Species	Asteraceae	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
NPO62756	Rumex balcanicus	n.a.	Roots	54.1Â±1.9	n.a.	n.a.	mg/g	PMID[39373260]

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	2
IC50	3
ED50	3
MIC	2
Ratio IC50	1

Activity Type	# Activity
Individual protein	4
Cell line	2
Organism	3
Non-molecular	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	59.42	%	PMID[24763362]
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	IC50	=	27430.0	nM	PMID[24763362]
NPT325	Individual protein	Cyclooxygenase-2	Ovis aries	IC50	=	32280.0	nM	PMID[24763362]
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	68.24	%	PMID[24763362]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	ED50	=	31.0	ug ml-1	PMID[2778455]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	36.7	ug ml-1	PMID[2778455]
NPT3519	Organism	Blumeria graminis f. sp. hordei	Blumeria graminis f. sp. hordei	IC50	=	20.0	ug.mL-1	PMID[21992072]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	36.7	ug ml-1	PMID[2778455]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	40.3	ug.mL-1	DOI[10.1007/s00044-013-0485-8]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	84.7	ug.mL-1	DOI[10.1007/s00044-013-0485-8]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	0.84	n.a.	PMID[24763362]

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
-	Artemia	LC50	=	105.0	ppm	PMID[2778455]

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 NPC160499 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	24407
0.1-0.2	23249
0.2-0.3	2141
0.3-0.4	50
0.4-0.5	5
0.5-0.6	5
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6	Remote Similarity	NPC94076
0.5833	Remote Similarity	NPC601693
0.5556	Remote Similarity	NPC603021
0.5385	Remote Similarity	NPC600218
0.5283	Remote Similarity	NPC607399
0.5208	Remote Similarity	NPC604528

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC160499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4430
0.1-0.2	4630
0.2-0.3	90
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data