NPASS Compound

Natural Product: NPC55470

Natural Product ID	NPC55470
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cepharadione A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL235921
PubChem CID	94577
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

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 34 38 0 0 0 0 0 0 0 0999 V2000 -3.9220 -1.1212 0.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9305 -0.0928 0.1679 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5276 -0.3413 0.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1503 -1.6567 -0.0404 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1645 -1.9761 -0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5017 -3.3117 -0.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8386 -3.6150 -0.3342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8235 -2.6683 -0.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4684 -1.3327 -0.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1439 -0.9928 -0.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7998 0.3546 0.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5643 0.6408 0.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9453 1.9782 0.2566 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0044 2.9934 0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3137 2.6526 0.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7490 1.3460 0.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1267 1.3890 0.0317 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5325 2.6939 -0.2835 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4418 3.4757 0.2358 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3655 2.3309 0.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7202 3.5421 0.4644 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3470 1.2591 0.2995 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5732 1.5169 0.3739 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0890 -1.4436 -0.9348 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7219 -1.9734 0.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8882 -0.6971 0.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9437 -2.4346 -0.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2816 -4.0723 -0.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1214 -4.6544 -0.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8945 -2.9345 -0.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2663 -0.6256 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3556 4.0047 0.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6940 2.8683 -1.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4502 2.8977 0.3349 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 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 13 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 22 2 1 0 12 3 1 0 19 15 1 0 10 5 1 0 16 11 2 0 1 24 1 0 1 25 1 0 1 26 1 0 4 27 1 0 6 28 1 0 7 29 1 0 8 30 1 0 9 31 1 0 14 32 1 0 18 33 1 0 18 34 1 0 M END

Standard InCHIKey	RZIGKFTVXWUUCX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3
SMILES	CN1c2cc3ccccc3c3c2c(cc2c3OCO2)C(=O)C1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	305.07	Volume:	299.531 ? Van der Waals volume.
Dense:	1.018	LogP:	2.919 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.896 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.267 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	26.0
TPSA:	55.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.473	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.675	Fsp³:	0.111
MCE-18:	54.6 ? 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:	0.776	Fluc inhibitor:	0.045 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.896 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.63 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.023	Promiscuous compounds:	0.167

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889	MDCK Permeability:	-4.589
Pgp-inhibitor:	0.898	Pgp-substrate:	0.021
PAMPA:	0.582 ? 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):	0.713
20% Bioavailability (F20%):	0.335	30% Bioavailability (F30%):	0.862
50% Bioavailability (F50%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102	MRP1:	0.62
Plasma Protein Binding (PPB):	98.281%	Volume Distribution (VD):	0.328
Fu:	1.514% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.827
OATP1B3 inhibitor:	0.969	BCRP inhibitor:	0.038
BSEP inhibitor:	0.978

ADMET: Metabolism

CYP1A2-inhibitor:	0.876	CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.363	CYP2C19-substrate:	0.661
CYP2C9-inhibitor:	0.065	CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.263	CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.059
CYP2B6-substrate:	0.049	CYP2C8-inhibitor:	0.724
HLM stability:	0.223 ? 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):

4.07

Half-life (T1/2):

0.54

ADMET: Toxicity

hERG Blockers:	0.19	hERG Blockers (10um):	0.38
Human Hepatotoxicity (H-HT):	0.891	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.957	Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.731	Skin Sensitization:	0.792
Carcinogencity:	0.968	Eye Corrosion:	0.0
Eye Irritation:	0.595	Respiratory Toxicity:	0.589
Drug-induced Neurotoxicity:	0.846	Ototoxicity:	0.524
Hematotoxicity:	0.96	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.324
A549 Cytotoxicity:	0.432	Hek293 Cytotoxicity:	0.737
BCF:	1.631 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.373 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.299 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.326 ? 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
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270572]
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	At a depth between 3 and 15 m in Las Lajas (Cdiz, Spain) (3606'11'' N, 525'47'' W)	2003-SEP	PMID[20014800]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24699147]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	Buds	n.a.	n.a.	PMID[25927817]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38612781]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	amniotic fluid	n.a.	Database[Article]
NPO20581	Sargassum fulvellum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20325	Dictyodendrilla cavernosa	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18333	Sphaerophysa salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19888	Doronicum grandiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26195	Tephrosia crassifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21780	Strychnos gossweileri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20965	Oxytropis lanata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26195	Tephrosia crassifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22498	Lithocarpus haipinii	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19668.1	Euphorbia characias subsp. wulfenii	Subspecies	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20581	Sargassum fulvellum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19888	Doronicum grandiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22942	Moesziomyces antarcticus	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22629	Spongia vaginalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26195	Tephrosia crassifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20704	Conus gladiator	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20965	Oxytropis lanata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28938	Artemisia coerulescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22436	Lora quadra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20325	Dictyodendrilla cavernosa	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21468	Dilophus guineensis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18333	Sphaerophysa salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21780	Strychnos gossweileri	Species	Loganiaceae	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
GI50	65
IC50	3

Activity Type	# Activity
Cell line	65
Organism	3

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
NPT1081	Cell line	BXPC-3	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[17624787]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	6.3	ug.mL-1	PMID[17624787]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	2.9	ug.mL-1	PMID[17624787]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	2.5	ug.mL-1	PMID[17624787]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	=	17.3	ug.mL-1	PMID[17624787]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	4.3	ug.mL-1	PMID[17624787]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	37670.38	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	18836.49	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	40738.03	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	20230.19	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	38459.18	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	45603.69	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	28444.61	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	38815.04	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	27227.01	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	17864.88	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	62086.9	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	41209.75	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	43351.09	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	24099.05	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	48752.85	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	47424.2	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	22908.68	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	52480.75	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	7498.94	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	35399.73	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	28379.19	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	22594.36	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	18323.14	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	26730.06	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	20749.14	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	25118.86	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	58613.82	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	23014.42	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	46665.94	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	33728.73	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	39355.01	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	39174.19	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	49090.79	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	15559.66	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	36057.86	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	21877.62	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	69662.65	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	30831.88	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	31550.05	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	50350.06	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	26730.06	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	16943.38	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	31260.79	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	37583.74	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	38725.76	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	7227.7	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	7834.3	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	51522.86	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	31188.9	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	8953.65	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	25234.81	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	34434.99	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	40457.59	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	28707.81	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	25585.86	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	42854.85	nM	PubChem BioAssay data set
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	0.05	ug.mL-1	PMID[15270572]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	115.0	ug.mL-1	PMID[15270572]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	0.2	ug.mL-1	PMID[15270572]

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 NPC55470 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	30100
0.1-0.2	18900
0.2-0.3	816
0.3-0.4	30
0.4-0.5	9
0.5-0.6	1
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	Natural Product ID
0.7925	Intermediate Similarity	NPC308943
0.5862	Remote Similarity	NPC603063

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC55470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4687
0.1-0.2	4410
0.2-0.3	53
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