NPASS Compound

Structure

CID36916 OpenBabel06191715362D 35 39 0 0 1 0 0 0 0 0999 V2000 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 10 26 1 0 0 0 0 11 24 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 28 1 0 0 0 0 15 21 2 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 33 1 0 0 0 0 17 32 1 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 35 1 0 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 30 2 0 0 0 0 23 25 1 0 0 0 0 23 31 1 6 0 0 0 24 34 1 0 0 0 0 25 12 1 1 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.12
Volume:	459.711
LogP:	2.015
LogD:	2.524
LogS:	-4.792
# Rotatable Bonds:	4
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	3.992
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.255
MDCK Permeability:	9.464632967137732e-06
Pgp-inhibitor:	0.44
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.366
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.65745544433594%
Volume Distribution (VD):	0.649
Pgp-substrate:	5.733587265014648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.31
CYP2D6-substrate:	0.419
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	5.144
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.341
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.183
Carcinogencity:	0.334
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.027

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC36916

Natural Product ID:	NPC36916
*Common Name:**	Silibinin
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	SEBFKMXJBCUCAI-DBMPWETRSA-N
Standard InCHI:	InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20?,23-,24?,25+/m0/s1
SMILES:	OCC1Oc2ccc(cc2OC1c1ccc(c(c1)OC)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL9509
PubChem CID:	3086637
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001844] Flavonolignans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5645	Silybum marianum	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	NP ID	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
EC50	7
IC50	44
Kd	2
Ki	9
MIC	2
Others	134
Potency	25

Activity Type	# Activity
Cell Line	78
CELL-LINE	1
Individual Protein	81
NON-MOLECULAR	15
Organism	13
Others	31
Protein Family	1
Subcellular	1
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1455	Individual Protein	P-glycoprotein 3	Mus musculus	Kd	=	6800.0	nM	PMID[567465]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	70.8	%	PMID[567468]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	96.5	%	PMID[567468]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	61.2	%	PMID[567468]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	38.1	%	PMID[567468]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	47.9	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	35.1	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	30.2	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	129.0	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	68.2	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	44.9	%	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	29900.0	nM	PMID[567469]
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	75.0	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	60.0	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	43.1	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	149.7	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	99.7	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	43.4	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	64.3	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	42.8	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	17.3	%	PMID[567470]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	82400.0	nM	PMID[567470]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	48.7	%	PMID[567471]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	42.3	%	PMID[567471]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	76.0	%	PMID[567472]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	58.9	%	PMID[567472]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	4.8	%	PMID[567473]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	7.7	%	PMID[567473]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	45.2	%	PMID[567473]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	77.0	%	PMID[567473]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	41000.0	nM	PMID[567473]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	106.0	%	PMID[567474]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	103.0	%	PMID[567474]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	66.0	%	PMID[567474]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	29.0	IU/L	PMID[567474]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	157.0	IU/L	PMID[567474]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	93.0	IU/L	PMID[567474]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat	=	5.8	/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Km	=	126000.0	nM	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat	=	13.3	/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Km	=	2800.0	nM	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat	=	4.0	/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Km	=	30000.0	nM	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat	=	6.9	/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Km	=	63000.0	nM	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat/Km	=	0.14	/uM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat/Km	=	0.13	/uM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat/Km	=	0.11	/uM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Kcat/Km	=	0.07	/uM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Activity	=	160.0	nM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Activity	=	150.0	nM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Activity	=	140.0	nM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Activity	=	120.0	nM/s	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	50.0	%	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	FC	=	80.0	n.a.	PMID[567477]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	20.0	%	PMID[567477]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	75700.0	nM	PMID[567478]
NPT4394	Individual Protein	Xanthine dehydrogenase/oxidase	Rattus norvegicus	IC50	=	80300.0	nM	PMID[567479]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	5.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	8.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	93.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	37.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	19.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	77.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	11.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	45.0	%	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	15000.0	nM	PMID[567481]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	4.8	%	PMID[567482]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	7.7	%	PMID[567482]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	45.2	%	PMID[567482]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	77.0	%	PMID[567482]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	38800.0	nM	PMID[567482]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	5.3	%	PMID[567482]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	22.0	%	PMID[567482]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	48.0	%	PMID[567482]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	50.8	%	PMID[567482]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	60.4	ug.mL-1	PMID[567482]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	800000.0	nM	PMID[567483]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[567484]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	12589.3	nM	PMID[567485]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	15848.9	nM	PMID[567484]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	15848.9	nM	PMID[567485]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	35481.3	nM	PMID[567485]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[567485]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[567484]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[567485]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Ki	=	5000.0	nM	PMID[567487]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Kinact	=	0.14	min-1	PMID[567487]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	32000.0	nM	PMID[567487]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.06	min-1	PMID[567487]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	132000.0	nM	PMID[567487]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.08	min-1	PMID[567487]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	45000.0	nM	PMID[567488]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	40.0	%	PMID[567488]
NPT134	Cell Line	SK-BR-3	Homo sapiens	Activity	=	196.3	uM	PMID[567489]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	196.4	uM	PMID[567489]
NPT134	Cell Line	SK-BR-3	Homo sapiens	Activity	=	197.0	uM	PMID[567490]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	222.8	uM	PMID[567490]
NPT883	Cell Line	Rat1	Rattus norvegicus	IC50	=	162000.0	nM	PMID[567491]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	72580.0	nM	PMID[567492]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	9990.0	nM	PMID[567492]
NPT737	Cell Line	HUVEC	Homo sapiens	MIC	=	50000000.0	nM	PMID[567492]
NPT737	Cell Line	HUVEC	Homo sapiens	MIC	=	75000.0	nM	PMID[567492]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[567485]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[567485]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	7.08	%	PMID[567496]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	5.5	%	PMID[567497]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[567485]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[567485]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[567498]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	400000.0	nM	PMID[567499]
NPT1654	Individual Protein	Urokinase-type plasminogen activator	Homo sapiens	IC50	=	21000.0	nM	PMID[567500]
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	8.3	%	PMID[567501]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[567485]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[567485]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	43030.0	nM	PMID[567505]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	43030.0	nM	PMID[567506]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	43730.0	nM	PMID[567510]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	93340.0	nM	PMID[567510]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	72650.0	nM	PMID[567510]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	38.0	%	PMID[567512]
NPT34	Cell Line	BV-2	Mus musculus	EC50	>	10000.0	nM	PMID[567512]
NPT804	Cell Line	HT-22	Mus musculus	EC50	>	10000.0	nM	PMID[567512]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Inhibition	=	10.1	%	PMID[567512]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Inhibition	=	2.0	%	PMID[567512]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KA	=	6.157	10'6L/mol	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KSV	=	0.2612	10'4L/mol	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	27.6	uM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	8400.0	nM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	8500.0	nM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	12100.0	nM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	3.7	uM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	700.0	nM	PMID[567515]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1700.0	nM	PMID[567515]
NPT2	Others	Unspecified		Delta Fmax	=	91.0	%	PMID[567465]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Relative protection	=	14.6	%	PMID[567466]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Relative protection	=	28.8	%	PMID[567466]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Relative protection	=	45.5	%	PMID[567466]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	%	PMID[567467]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	4.8	%	PMID[567467]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	7.7	%	PMID[567467]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	45.2	%	PMID[567467]
NPT2	Others	Unspecified		Activity	=	0.0	n.a.	PMID[567475]
NPT1593	Tissue	Liver	Rattus norvegicus	IC50	=	84800.0	nM	PMID[567479]
NPT1	Others	Radical scavenging activity		Activity	=	16.6	%	PMID[567480]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	38.2	%	PMID[567480]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	196500.0	nM	PMID[567480]
NPT1593	Tissue	Liver	Rattus norvegicus	IC50	=	22700.0	nM	PMID[567480]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	58100.0	nM	PMID[567483]
NPT1	Others	Radical scavenging activity		IC50	=	2100000.0	nM	PMID[567483]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	25118.9	nM	PMID[567484]
NPT2	Others	Unspecified		Potency	=	4109.5	nM	PMID[567485]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	39810.7	nM	PMID[567485]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	28183.8	nM	PMID[567484]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	18830.0	nM	PMID[567488]
NPT35	Others	n.a.		LogP	=	2.07	n.a.	PMID[567491]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	28.2	%	PMID[567493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	33.4	%	PMID[567493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.1	%	PMID[567493]
NPT27	Others	Unspecified		MTD	=	6.25	ug ml-1	PMID[567493]
NPT1	Others	Radical scavenging activity		IC50	=	284000.0	nM	PMID[567494]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[567485]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-7.94	%	PMID[567496]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	15.0	%	PMID[567497]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.1	%	PMID[567497]
NPT2	Others	Unspecified		Potency	n.a.	20596.2	nM	PMID[567485]
NPT1644	Protein Family	Trypsin	Homo sapiens	IC50	=	3700.0	nM	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	20900.0	nM	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	Ka	=	5.39	10'4/M	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	Kd	=	18600.0	nM	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	RU	=	1424.0	n.a.	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	Inhibition	=	43.0	%	PMID[567500]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	25000.0	nM	PMID[567500]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	4265.8	nM	PMID[567502]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	3270.0	nM	PMID[567502]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	54.77	%	PMID[567502]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	6165.95	nM	PMID[567502]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	3370.0	nM	PMID[567502]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	46.89	%	PMID[567502]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[567485]
NPT35	Others	n.a.		IC50	=	392200.0	nM	PMID[567503]
NPT27	Others	Unspecified		Activity	=	45.3	%	PMID[567503]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Activity	=	42.4	%	PMID[567503]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[567485]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	EC50	=	64.0	ug.mL-1	PMID[567504]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBIC	>	124.0	ug ml-1	PMID[567504]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	93340.0	nM	PMID[567505]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	72650.0	nM	PMID[567505]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	72650.0	nM	PMID[567506]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	93340.0	nM	PMID[567506]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	69200.0	nM	PMID[567507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.3	%	PMID[567507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	27.0	%	PMID[567507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	47.0	%	PMID[567507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	53.8	%	PMID[567507]
NPT35	Others	n.a.		LogP	=	-0.63	n.a.	PMID[567508]
NPT35	Others	n.a.		Activity	=	0.47	equiv	PMID[567508]
NPT2	Others	Unspecified		IC50	=	67000.0	nM	PMID[567508]
NPT35	Others	n.a.		IC50	=	553000.0	nM	PMID[567508]
NPT35	Others	n.a.		Activity	=	0.92	equiv	PMID[567508]
NPT35	Others	n.a.		Activity	=	0.92	equiv	PMID[567509]
NPT35	Others	n.a.		IC50	=	244000.0	nM	PMID[567509]
NPT35	Others	n.a.		Activity	=	0.78	equiv	PMID[567509]
NPT2	Others	Unspecified		IC50	=	77100.0	nM	PMID[567509]
NPT35	Others	n.a.		Activity	=	0.25	equiv	PMID[567509]
NPT35	Others	n.a.		IC50	=	2940.0	nM	PMID[567509]
NPT35	Others	n.a.		Activity	=	0.42	equiv	PMID[567509]
NPT2	Others	Unspecified		IC50	=	56500.0	nM	PMID[567509]
NPT20632	ORGANISM	Chikungunya virus	Chikungunya virus	IC50	=	22500.0	nM	PMID[567511]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	16.0	%	PMID[567512]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	4.8	%	PMID[567512]
NPT35	Others	n.a.		Activity	=	0.6	equiv	PMID[567512]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.1996	n.a.	PMID[567513]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	IC50	=	60000.0	nM	PMID[567514]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.33	n.a.	PMID[567514]
NPT2	Others	Unspecified		IC50	=	340000.0	nM	PMID[567516]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[567516]
NPT27323	CELL-LINE	Huh7.5.1	Homo sapiens	CC50	=	80000.0	nM	PMID[567514]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC36916 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	1697
0.2-0.3	4293
0.3-0.4	10182
0.4-0.5	7792
0.5-0.6	3657
0.6-0.7	4734
0.7-0.8	5386
0.8-0.85	2545
0.85-0.9	1607
0.9-0.95	360
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36
1.0	High Similarity	NPC58223
1.0	High Similarity	NPC7154
1.0	High Similarity	NPC125039
1.0	High Similarity	NPC72787
1.0	High Similarity	NPC7688
0.9679	High Similarity	NPC165970
0.9679	High Similarity	NPC305987
0.9679	High Similarity	NPC288131
0.9679	High Similarity	NPC158188
0.9679	High Similarity	NPC84324
0.9679	High Similarity	NPC66618
0.9679	High Similarity	NPC113163
0.9623	High Similarity	NPC14662
0.9623	High Similarity	NPC295082
0.962	High Similarity	NPC477840
0.9618	High Similarity	NPC477841
0.9615	High Similarity	NPC101731
0.956	High Similarity	NPC471213
0.9554	High Similarity	NPC471499
0.9554	High Similarity	NPC142252
0.9551	High Similarity	NPC172202
0.9551	High Similarity	NPC284127
0.9551	High Similarity	NPC476410
0.9548	High Similarity	NPC320825
0.9548	High Similarity	NPC326037
0.9548	High Similarity	NPC13858
0.9548	High Similarity	NPC250922
0.9503	High Similarity	NPC102277
0.9503	High Similarity	NPC279209
0.95	High Similarity	NPC260266
0.95	High Similarity	NPC243877
0.9494	High Similarity	NPC219927
0.9494	High Similarity	NPC476247
0.949	High Similarity	NPC470326
0.949	High Similarity	NPC287328
0.949	High Similarity	NPC282009
0.9487	High Similarity	NPC471479
0.9487	High Similarity	NPC52530
0.9487	High Similarity	NPC471515
0.9487	High Similarity	NPC183851
0.9487	High Similarity	NPC63454
0.9444	High Similarity	NPC186847
0.9444	High Similarity	NPC472454
0.9444	High Similarity	NPC257667
0.9441	High Similarity	NPC475212
0.9434	High Similarity	NPC472625
0.943	High Similarity	NPC472632
0.943	High Similarity	NPC289771
0.943	High Similarity	NPC173137
0.943	High Similarity	NPC26326
0.9427	High Similarity	NPC22192
0.9423	High Similarity	NPC471500
0.9419	High Similarity	NPC18727
0.9375	High Similarity	NPC224280
0.9375	High Similarity	NPC62261
0.9371	High Similarity	NPC474034
0.9371	High Similarity	NPC474033
0.9367	High Similarity	NPC470183
0.9367	High Similarity	NPC174953
0.9367	High Similarity	NPC263449
0.9363	High Similarity	NPC67876
0.9363	High Similarity	NPC472598
0.9363	High Similarity	NPC474055
0.9355	High Similarity	NPC61506
0.9355	High Similarity	NPC240476
0.9355	High Similarity	NPC9743
0.9355	High Similarity	NPC36835
0.9355	High Similarity	NPC302950
0.9355	High Similarity	NPC246162
0.9355	High Similarity	NPC219582
0.9355	High Similarity	NPC19721
0.9355	High Similarity	NPC260491
0.9355	High Similarity	NPC236637
0.9321	High Similarity	NPC270578
0.9321	High Similarity	NPC52382
0.9317	High Similarity	NPC5778
0.9317	High Similarity	NPC477517
0.9317	High Similarity	NPC236934
0.9308	High Similarity	NPC471211
0.9308	High Similarity	NPC474038
0.9308	High Similarity	NPC112418
0.9308	High Similarity	NPC472634
0.9308	High Similarity	NPC471212
0.9308	High Similarity	NPC471210
0.9308	High Similarity	NPC308992
0.9304	High Similarity	NPC473990
0.9304	High Similarity	NPC53545
0.9304	High Similarity	NPC117418
0.9299	High Similarity	NPC195796
0.9299	High Similarity	NPC291878
0.9299	High Similarity	NPC35038
0.9299	High Similarity	NPC278778
0.9295	High Similarity	NPC27532
0.9295	High Similarity	NPC325028
0.9295	High Similarity	NPC246328
0.9295	High Similarity	NPC256346
0.9264	High Similarity	NPC231194
0.9264	High Similarity	NPC177731
0.9264	High Similarity	NPC105095
0.9264	High Similarity	NPC79056
0.9264	High Similarity	NPC285197
0.9264	High Similarity	NPC51326
0.9264	High Similarity	NPC67105
0.9264	High Similarity	NPC476365
0.9264	High Similarity	NPC95866
0.9264	High Similarity	NPC44328
0.9259	High Similarity	NPC160156
0.9259	High Similarity	NPC92565
0.9255	High Similarity	NPC234052
0.925	High Similarity	NPC471745
0.925	High Similarity	NPC472635
0.9245	High Similarity	NPC192686
0.9245	High Similarity	NPC475784
0.9245	High Similarity	NPC118256
0.9245	High Similarity	NPC119209
0.9245	High Similarity	NPC472631
0.9245	High Similarity	NPC472630
0.9245	High Similarity	NPC471744
0.9241	High Similarity	NPC162869
0.9241	High Similarity	NPC471209
0.9241	High Similarity	NPC474208
0.9241	High Similarity	NPC156057
0.9241	High Similarity	NPC475267
0.9241	High Similarity	NPC474836
0.9241	High Similarity	NPC27337
0.9241	High Similarity	NPC48208
0.9241	High Similarity	NPC291508
0.9236	High Similarity	NPC45849
0.9236	High Similarity	NPC200761
0.9236	High Similarity	NPC470327
0.9236	High Similarity	NPC321779
0.9236	High Similarity	NPC477503
0.9231	High Similarity	NPC472912
0.9226	High Similarity	NPC338131
0.9217	High Similarity	NPC217520
0.9217	High Similarity	NPC139571
0.9212	High Similarity	NPC294629
0.9212	High Similarity	NPC16194
0.9212	High Similarity	NPC220173
0.9212	High Similarity	NPC294815
0.9212	High Similarity	NPC476472
0.9212	High Similarity	NPC473327
0.9212	High Similarity	NPC19108
0.9207	High Similarity	NPC33054
0.9207	High Similarity	NPC471725
0.9207	High Similarity	NPC155877
0.9207	High Similarity	NPC47140
0.9207	High Similarity	NPC26230
0.9207	High Similarity	NPC256760
0.9207	High Similarity	NPC203259
0.9207	High Similarity	NPC81332
0.9207	High Similarity	NPC471748
0.9207	High Similarity	NPC262580
0.9207	High Similarity	NPC134532
0.9207	High Similarity	NPC212038
0.9207	High Similarity	NPC60735
0.9207	High Similarity	NPC289396
0.9207	High Similarity	NPC176740
0.9207	High Similarity	NPC67134
0.9207	High Similarity	NPC271848
0.9202	High Similarity	NPC203050
0.9202	High Similarity	NPC326877
0.9202	High Similarity	NPC195257
0.9202	High Similarity	NPC219904
0.9202	High Similarity	NPC223747
0.9202	High Similarity	NPC177480
0.9202	High Similarity	NPC293629
0.9202	High Similarity	NPC43587
0.9202	High Similarity	NPC227508
0.9202	High Similarity	NPC229687
0.9202	High Similarity	NPC107627
0.9202	High Similarity	NPC209296
0.9202	High Similarity	NPC188079
0.9202	High Similarity	NPC120099
0.9202	High Similarity	NPC225434
0.9198	High Similarity	NPC21100
0.9198	High Similarity	NPC197285
0.9198	High Similarity	NPC115674
0.9198	High Similarity	NPC210073
0.9198	High Similarity	NPC224851
0.9193	High Similarity	NPC29830
0.9187	High Similarity	NPC134783
0.9182	High Similarity	NPC55738
0.9182	High Similarity	NPC123544
0.9182	High Similarity	NPC152904
0.9177	High Similarity	NPC201837
0.9177	High Similarity	NPC235165
0.9177	High Similarity	NPC209614
0.9177	High Similarity	NPC470328
0.9177	High Similarity	NPC208152
0.9177	High Similarity	NPC474638
0.9177	High Similarity	NPC255106
0.9177	High Similarity	NPC472626
0.9177	High Similarity	NPC78492
0.9172	High Similarity	NPC192083
0.9172	High Similarity	NPC213896
0.9172	High Similarity	NPC141212
0.9172	High Similarity	NPC58382
0.9172	High Similarity	NPC162351

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	944
0.2-0.3	1820
0.3-0.4	2607
0.4-0.5	1797
0.5-0.6	966
0.6-0.7	451
0.7-0.8	127
0.8-0.85	26
0.85-0.9	21
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6166	Phase 2
1.0	High Similarity	NPD6167	Clinical (unspecified phase)
1.0	High Similarity	NPD6168	Clinical (unspecified phase)
0.9355	High Similarity	NPD1934	Approved
0.9264	High Similarity	NPD7074	Phase 3
0.9207	High Similarity	NPD6797	Phase 2
0.9202	High Similarity	NPD7054	Approved
0.9172	High Similarity	NPD2393	Clinical (unspecified phase)
0.9152	High Similarity	NPD7251	Discontinued
0.9146	High Similarity	NPD7472	Approved
0.9096	High Similarity	NPD7808	Phase 3
0.8976	High Similarity	NPD7993	Clinical (unspecified phase)
0.8938	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD4868	Clinical (unspecified phase)
0.8931	High Similarity	NPD2801	Approved
0.8875	High Similarity	NPD3817	Phase 2
0.8869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8846	High Similarity	NPD1512	Approved
0.8795	High Similarity	NPD3818	Discontinued
0.8743	High Similarity	NPD7804	Clinical (unspecified phase)
0.8742	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD4381	Clinical (unspecified phase)
0.865	High Similarity	NPD7075	Discontinued
0.8606	High Similarity	NPD6959	Discontinued
0.8545	High Similarity	NPD5494	Approved
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8528	High Similarity	NPD8443	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8397	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8313	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5402	Approved
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD6799	Approved
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.821	Intermediate Similarity	NPD5403	Approved
0.8161	Intermediate Similarity	NPD6559	Discontinued
0.8153	Intermediate Similarity	NPD2796	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8086	Intermediate Similarity	NPD5401	Approved
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD1613	Approved
0.8065	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD1240	Approved
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7879	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3027	Phase 3
0.7861	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD1247	Approved
0.7849	Intermediate Similarity	NPD7199	Phase 2
0.7848	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD919	Approved
0.7834	Intermediate Similarity	NPD943	Approved
0.7829	Intermediate Similarity	NPD7228	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3749	Approved
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD3750	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD1653	Approved
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7390	Discontinued
0.758	Intermediate Similarity	NPD4908	Phase 1
0.7566	Intermediate Similarity	NPD6778	Approved
0.7566	Intermediate Similarity	NPD6782	Approved
0.7566	Intermediate Similarity	NPD6776	Approved
0.7566	Intermediate Similarity	NPD6777	Approved
0.7566	Intermediate Similarity	NPD6781	Approved
0.7566	Intermediate Similarity	NPD6780	Approved
0.7566	Intermediate Similarity	NPD6779	Approved
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7545	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD37	Approved
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.7455	Intermediate Similarity	NPD2800	Approved
0.7453	Intermediate Similarity	NPD447	Suspended
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.7448	Intermediate Similarity	NPD7698	Approved
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7448	Intermediate Similarity	NPD7697	Approved
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7378	Intermediate Similarity	NPD6100	Approved
0.7378	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7363	Intermediate Similarity	NPD7240	Approved
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7346	Intermediate Similarity	NPD1933	Approved
0.7337	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3748	Approved
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD6535	Approved
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7302	Intermediate Similarity	NPD6534	Approved
0.7301	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD9494	Approved
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD920	Approved
0.7245	Intermediate Similarity	NPD7584	Approved
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7874	Approved
0.7212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7186	Intermediate Similarity	NPD7801	Approved
0.716	Intermediate Similarity	NPD2309	Approved
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.7118	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7680	Approved
0.7081	Intermediate Similarity	NPD7039	Approved
0.7081	Intermediate Similarity	NPD7038	Approved
0.7077	Intermediate Similarity	NPD2493	Approved
0.7077	Intermediate Similarity	NPD2494	Approved
0.7072	Intermediate Similarity	NPD5242	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD1203	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5353	Approved
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD2163	Approved
0.7041	Intermediate Similarity	NPD1652	Phase 2
0.7033	Intermediate Similarity	NPD2403	Approved
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5124	Phase 1
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.699	Remote Similarity	NPD3450	Approved
0.699	Remote Similarity	NPD3452	Approved
0.6989	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1548	Phase 1
0.6982	Remote Similarity	NPD2424	Discontinued
0.6977	Remote Similarity	NPD7213	Phase 3
0.6977	Remote Similarity	NPD7212	Phase 2
0.6975	Remote Similarity	NPD2861	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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