NPASS Compound

Natural Product: NPC256283

Natural Product ID	NPC256283
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-Dihydroxy-2-(3-Hydroxy-4-Methoxyphenyl)-6-Methoxychromen-4-One
IUPAC Name	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6-methoxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL74838
PubChem CID	5469524
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-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 38 40 0 0 0 0 0 0 0 0999 V2000 -7.0944 0.2926 -0.0083 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0670 1.0400 0.5955 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7154 0.6820 0.4670 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3318 -0.4231 -0.2600 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9964 -0.7769 -0.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9864 -0.0476 0.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3983 1.0691 0.9353 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7219 1.4245 1.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0700 2.5352 1.7985 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5729 -0.3820 0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0988 -1.4607 -0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2428 -1.7683 -0.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 -2.7497 -1.3385 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1189 -0.9318 -0.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6056 0.1358 0.6422 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4732 0.9864 1.3031 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8300 0.7456 1.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3568 -0.3273 0.5634 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4782 -1.1664 -0.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9109 -2.2708 -0.8127 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7034 -0.6091 0.4868 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5789 -0.1333 -0.4914 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7308 1.5980 1.9207 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2985 0.3840 0.6990 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7887 0.1100 -1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2628 -0.6909 0.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0044 0.9281 0.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1135 -1.0039 -0.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7270 -1.6528 -0.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5991 1.6514 1.4057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4175 3.1765 2.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7777 -2.1224 -1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0965 1.8493 1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9175 -2.3309 -1.8142 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9794 0.2354 -1.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2608 -0.9429 -0.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2347 0.6884 -0.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2680 2.2586 1.3632 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 6 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 18 21 1 0 21 22 1 0 17 23 1 0 15 24 1 0 8 3 1 0 24 10 1 0 19 14 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 9 31 1 0 11 32 1 0 16 33 1 0 20 34 1 0 22 35 1 0 22 36 1 0 22 37 1 0 23 38 1 0 M END

Standard InCHIKey	VCWFILUULGOFCD-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C17H14O7/c1-22-12-4-3-8(5-9(12)18)13-6-10(19)15-14(24-13)7-11(20)17(23-2)16(15)21/h3-7,18,20-21H,1-2H3
SMILES	COc1ccc(cc1O)c1cc(=O)c2c(cc(c(c2O)OC)O)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	330.07	Volume:	317.359 ? Van der Waals volume.
Dense:	1.04	LogP:	2.374 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.049 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	18.0
TPSA:	109.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.677	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.475	Fsp³:	0.118
MCE-18:	19.0 ? 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:	0.689	Fluc inhibitor:	0.802 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.71 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.465	Promiscuous compounds:	0.853

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.098	MDCK Permeability:	-4.785
Pgp-inhibitor:	0.196	Pgp-substrate:	0.4
PAMPA:	0.09 ? 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):	0.028
20% Bioavailability (F20%):	0.303	30% Bioavailability (F30%):	0.767
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.808
Plasma Protein Binding (PPB):	97.342%	Volume Distribution (VD):	-0.577
Fu:	3.005% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.962
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.932
BSEP inhibitor:	0.263

ADMET: Metabolism

CYP1A2-inhibitor:	0.91	CYP1A2-substrate:	0.47
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.996	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.708 ? 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):

2.649

Half-life (T1/2):

1.512

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.478
Human Hepatotoxicity (H-HT):	0.397	Drug-induced Liver Injury (DILI):	0.637
AMES Toxicity:	0.564	Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.689	Skin Sensitization:	0.753
Carcinogencity:	0.669	Eye Corrosion:	0.519
Eye Irritation:	0.995	Respiratory Toxicity:	0.815
Drug-induced Neurotoxicity:	0.072	Ototoxicity:	0.119
Hematotoxicity:	0.138	Drug-induced Nephrotoxicity:	0.081
Genotoxicity:	0.749	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.34	Hek293 Cytotoxicity:	0.528
BCF:	0.726 ? 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:	3.438 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.402 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.849 ? 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
NPO17829	Ibervillea sonorae	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2007-967117]
NPO20756	Aspergillus unilateralis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15602607]
NPO21969	Veronicastrum virginicum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20399	Turbinellus floccosus	Species	Gomphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21518	Senecio tricephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17829	Ibervillea sonorae	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11698	Drosera spatulata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9599	Delphinium hybr	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20756	Aspergillus unilateralis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19601	Albizia amara	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3676	Fusarium sambucinum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21518	Senecio tricephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19601	Albizia amara	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11698	Drosera spatulata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20756	Aspergillus unilateralis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9599	Delphinium hybr	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3676	Fusarium sambucinum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20399	Turbinellus floccosus	Species	Gomphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21969	Veronicastrum virginicum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17829	Ibervillea sonorae	Species	Cucurbitaceae	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	60

Activity Type	# Activity
Cell line	60

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
NPT517	Cell line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	6000.0	nM	PMID[9632366]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	405.51	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	6683.44	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	13803.84	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	17741.89	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	14962.36	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	6266.14	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	1253.14	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	7638.36	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	3411.93	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	2685.34	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	1303.17	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	679.2	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	4897.79	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	9036.49	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	3191.54	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2691.53	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	6902.4	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	9549.93	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	5260.17	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	32809.53	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	5508.08	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	13551.89	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	68233.87	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	3133.29	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	3184.2	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	1972.42	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	11561.12	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	3404.08	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	2454.71	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	50466.13	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	3507.52	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	19275.25	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	3926.45	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	6123.5	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	6397.35	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	3647.54	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	3483.37	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	1896.71	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	9246.98	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	10739.89	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	10046.16	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	3793.15	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	6280.58	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	3303.7	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	5942.92	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	4036.45	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	13931.57	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	2831.39	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	582.1	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	4623.81	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	4954.5	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	3076.1	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	8016.78	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	3698.28	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	15958.79	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	34994.52	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	9397.23	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	22542.39	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	20606.3	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 NPC256283 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	28349
0.1-0.2	18076
0.2-0.3	2511
0.3-0.4	623
0.4-0.5	213
0.5-0.6	51
0.6-0.7	11
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8039	Intermediate Similarity	NPC156222
0.7885	Intermediate Similarity	NPC100887
0.7593	Intermediate Similarity	NPC255350
0.75	Intermediate Similarity	NPC293183
0.7455	Intermediate Similarity	NPC160951
0.7455	Intermediate Similarity	NPC52005
0.7358	Intermediate Similarity	NPC241498
0.7358	Intermediate Similarity	NPC284552
0.7273	Intermediate Similarity	NPC83508
0.7091	Intermediate Similarity	NPC9609
0.6964	Remote Similarity	NPC146165
0.6964	Remote Similarity	NPC212678
0.6885	Remote Similarity	NPC470402
0.6842	Remote Similarity	NPC223579
0.6552	Remote Similarity	NPC287101
0.6552	Remote Similarity	NPC196439
0.6552	Remote Similarity	NPC607642
0.6552	Remote Similarity	NPC608258
0.6508	Remote Similarity	NPC213622
0.6207	Remote Similarity	NPC50715
0.6034	Remote Similarity	NPC601901
0.5862	Remote Similarity	NPC203891
0.5862	Remote Similarity	NPC44079
0.5763	Remote Similarity	NPC184136
0.5763	Remote Similarity	NPC231772
0.5763	Remote Similarity	NPC145379
0.5667	Remote Similarity	NPC25270
0.5593	Remote Similarity	NPC98661
0.5574	Remote Similarity	NPC115798
0.5574	Remote Similarity	NPC69394
0.5574	Remote Similarity	NPC82325
0.5574	Remote Similarity	NPC54394
0.5574	Remote Similarity	NPC209487
0.5574	Remote Similarity	NPC29841
0.55	Remote Similarity	NPC57030
0.55	Remote Similarity	NPC163524
0.5484	Remote Similarity	NPC93376
0.5484	Remote Similarity	NPC12200
0.5484	Remote Similarity	NPC606638
0.5424	Remote Similarity	NPC26227
0.541	Remote Similarity	NPC162313
0.5397	Remote Similarity	NPC183950
0.5397	Remote Similarity	NPC47781
0.5333	Remote Similarity	NPC274327
0.5333	Remote Similarity	NPC266960
0.5333	Remote Similarity	NPC239128
0.5333	Remote Similarity	NPC29353
0.5333	Remote Similarity	NPC609062
0.5323	Remote Similarity	NPC204854
0.5323	Remote Similarity	NPC200740
0.5263	Remote Similarity	NPC605067
0.5246	Remote Similarity	NPC62536
0.5246	Remote Similarity	NPC120163
0.5246	Remote Similarity	NPC120464
0.5246	Remote Similarity	NPC276409
0.5238	Remote Similarity	NPC25495
0.5238	Remote Similarity	NPC189179
0.5238	Remote Similarity	NPC75215
0.5238	Remote Similarity	NPC283600
0.52	Remote Similarity	NPC475942
0.5167	Remote Similarity	NPC472438
0.5167	Remote Similarity	NPC75279
0.5161	Remote Similarity	NPC108406
0.5161	Remote Similarity	NPC312924
0.5161	Remote Similarity	NPC603662
0.5082	Remote Similarity	NPC275722
0.5082	Remote Similarity	NPC600177
0.5079	Remote Similarity	NPC300943
0.5079	Remote Similarity	NPC183597
0.5079	Remote Similarity	NPC270620
0.5079	Remote Similarity	NPC55205
0.5065	Remote Similarity	NPC22832

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC256283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5108
0.1-0.2	3952
0.2-0.3	82
0.3-0.4	5
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7593	Intermediate Similarity	NPD2801	Pre-clinical

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