NPASS Compound

Structure

CID77000 OpenBabel06191715412D 22 25 0 0 1 0 0 0 0 0999 V2000 0.8338 2.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0133 -2.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8791 -2.4285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8478 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0125 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5064 -1.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3422 -1.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8480 -1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8341 1.4471 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1775 -0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5061 -0.4818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1778 -1.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6700 0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5055 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3414 0.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6703 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0131 -1.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 2.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2073 1.4656 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 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 1 1 6 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.14
Volume:	313.506
LogP:	5.945
LogD:	3.87
LogS:	-3.916
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.058
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	1.666021671553608e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.128
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	98.59485626220703%
Volume Distribution (VD):	1.997
Pgp-substrate:	3.677635669708252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.43
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	4.362
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.226
Skin Sensitization:	0.914
Carcinogencity:	0.682
Eye Corrosion:	0.004
Eye Irritation:	0.881
Respiratory Toxicity:	0.792

Download Data

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

Natural Product: NPC77000

Natural Product ID:	NPC77000
*Common Name:**	Cryptotanshinone
IUPAC Name:	(1R)-1,6,6-trimethyl-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:	Cryptotanshinone
Standard InCHIKey:	GVKKJJOMQCNPGB-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3/t10-/m0/s1
SMILES:	C[C@H]1COC2=C1C(=O)C(=O)c1c3CCCC(C)(C)c3ccc21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL187460
PubChem CID:	160254
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880325]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1567426]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	0tholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	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	5
ED50	3
GI50	60
IC50	32
Ki	6
Others	36
Potency	64

Activity Type	# Activity
Cell Line	72
Individual Protein	91
NON-MOLECULAR	5
Organism	13
Others	15
PROTEIN FAMILY	4
Protein-Protein Interaction	4
SINGLE PROTEIN	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.41	ug ml-1	PMID[451047]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	ED50	=	0.16	ug ml-1	PMID[451047]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	13500.0	nM	PMID[451048]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	10200.0	nM	PMID[451048]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	37400.0	nM	PMID[451049]
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	9.12	uM	PMID[451050]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	=	29.7	uM	PMID[451050]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	17.2	uM	PMID[451050]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	50118.7	nM	PMID[451053]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PMID[451053]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	17782.8	nM	PMID[451053]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PMID[451053]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	28183.8	nM	PMID[451054]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[451053]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	3981.1	nM	PMID[451053]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[451054]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	891.3	nM	PMID[451053]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	19905.4	nM	PMID[451054]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	7062.7	nM	PMID[451053]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	25118.9	nM	PMID[451053]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	3953.0	nM	PMID[451053]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	14816.0	nM	PMID[451053]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	22387.2	nM	PMID[451053]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[451053]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[451053]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[451054]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[451053]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[451053]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	16353.5	nM	PMID[451053]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	5800.0	nM	PMID[451056]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[451054]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[451053]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[451053]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[451053]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[451053]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[451054]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[451053]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	21331.3	nM	PMID[451053]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	n.a.	33380.0	nM	PMID[451053]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	1610.65	nM	PMID[451057]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	4365.16	nM	PMID[451057]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	1548.82	nM	PMID[451057]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3597.49	nM	PMID[451057]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	4698.94	nM	PMID[451057]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	40831.94	nM	PMID[451057]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	2387.81	nM	PMID[451057]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	1352.07	nM	PMID[451057]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	3349.65	nM	PMID[451057]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	305.49	nM	PMID[451057]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	381.94	nM	PMID[451057]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	3605.79	nM	PMID[451057]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	18323.14	nM	PMID[451057]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	325.84	nM	PMID[451057]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	4236.43	nM	PMID[451057]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	3681.29	nM	PMID[451057]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1995.26	nM	PMID[451057]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2786.12	nM	PMID[451057]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	16069.41	nM	PMID[451057]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	2576.32	nM	PMID[451057]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	11967.41	nM	PMID[451057]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	2517.68	nM	PMID[451057]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	8184.65	nM	PMID[451057]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	3419.79	nM	PMID[451057]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	1729.82	nM	PMID[451057]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	2009.09	nM	PMID[451057]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2192.8	nM	PMID[451057]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	1032.76	nM	PMID[451057]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	1644.37	nM	PMID[451057]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	3311.31	nM	PMID[451057]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	12189.9	nM	PMID[451057]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	2517.68	nM	PMID[451057]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	2108.63	nM	PMID[451057]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	4246.2	nM	PMID[451057]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1049.54	nM	PMID[451057]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	881.05	nM	PMID[451057]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[451054]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[451053]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	2483.13	nM	PMID[451057]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	1940.89	nM	PMID[451057]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	2964.83	nM	PMID[451057]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	1901.08	nM	PMID[451057]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	2218.2	nM	PMID[451057]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	4623.81	nM	PMID[451057]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	11614.49	nM	PMID[451057]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	4931.74	nM	PMID[451057]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	9462.37	nM	PMID[451057]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	1633.05	nM	PMID[451057]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	2032.36	nM	PMID[451057]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1415.79	nM	PMID[451057]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	5804.8	nM	PMID[451053]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	8222.43	nM	PMID[451057]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1678.8	nM	PMID[451057]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2710.19	nM	PMID[451057]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[451054]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[451053]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[451054]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	2290.87	nM	PMID[451057]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	1954.34	nM	PMID[451057]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	3419.79	nM	PMID[451057]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	4305.27	nM	PMID[451057]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	3243.4	nM	PMID[451057]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2182.73	nM	PMID[451057]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	3191.54	nM	PMID[451057]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	6295.06	nM	PMID[451057]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1148.15	nM	PMID[451057]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[451053]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[451053]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[451053]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	226700.0	nM	PMID[451058]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	800.0	nM	PMID[451058]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	Ki	=	9000.0	nM	PMID[451058]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	87600.0	nM	PMID[451058]
NPT201	Individual Protein	Papain	Carica papaya	IC50	=	89800.0	nM	PMID[451058]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	=	69600.0	nM	PMID[451058]
NPT200	Individual Protein	SARS coronavirus 3C-like proteinase	SARS coronavirus	IC50	=	10100.0	nM	PMID[451058]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	Inhibition	=	75.0	%	PMID[451059]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	3.33	%	PMID[451060]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	4600.0	nM	PMID[451061]
NPT933	Cell Line	U373 MG	Homo sapiens	FC	=	4.5	n.a.	PMID[451063]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Inhibition	=	81.0	%	PMID[451063]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[451063]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	=	6410.0	nM	PMID[451063]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	290.0	nM	PMID[451063]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	141.0	nM	PMID[451063]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	544.0	nM	PMID[451063]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[451053]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	IC50	=	23900.0	nM	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	IC50	=	45180.0	nM	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Kcat/Km	=	2.15	/mM/s	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Kcat	=	0.36	/s	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Km	=	170000.0	nM	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Vmax	=	6.96	microM/min	PMID[451064]
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	IC50	=	55700.0	nM	PMID[451064]
NPT3914	Individual Protein	Tyrosine-protein phosphatase non-receptor type 9	Homo sapiens	IC50	=	59400.0	nM	PMID[451064]
NPT1870	Individual Protein	Receptor-type tyrosine-protein phosphatase F (LAR)	Homo sapiens	IC50	=	36900.0	nM	PMID[451064]
NPT287	Individual Protein	Leukocyte common antigen	Homo sapiens	IC50	=	41400.0	nM	PMID[451064]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	33500.0	nM	PMID[451064]
NPT205	Individual Protein	Protein-tyrosine phosphatase 1C	Homo sapiens	IC50	=	39500.0	nM	PMID[451064]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	IC50	=	22500.0	nM	PMID[451064]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	25.0	%	PMID[451066]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[451053]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[451053]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[451053]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[451053]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	85.0	%	PMID[451067]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	78.0	%	PMID[451067]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1580.0	nM	PMID[451048]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1360.0	nM	PMID[451048]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[451048]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	18400.0	nM	PMID[451049]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12500.0	nM	PMID[451049]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6900.0	nM	PMID[451049]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7500.0	nM	PMID[451049]
NPT3912	Tissue	Artery	Sus scrofa	ED50	=	-7.2	ug ml-1	PMID[451051]
NPT3912	Tissue	Artery	Sus scrofa	Emax	=	64.9	%	PMID[451051]
NPT27	Others	Unspecified		EC50	=	22900.0	nM	PMID[451052]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	50.0	%	PMID[451052]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	14089.0	nM	PMID[451053]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	5172.0	nM	PMID[451053]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	12589.3	nM	PMID[451053]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PMID[451054]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PMID[451053]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	17782.8	nM	PMID[451053]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[451053]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[451054]
NPT2	Others	Unspecified		Inhibition	=	43.7	%	PMID[451055]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[451053]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[451053]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	28183.8	nM	PMID[451053]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[451053]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[451053]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[451053]
NPT917	Individual Protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	IC50	n.a.	90060.0	nM	PMID[451053]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2936.2	nM	PMID[451053]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[451053]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[451053]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[451053]
NPT2	Others	Unspecified		IC50	=	119800.0	nM	PMID[451058]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	12.06	%	PMID[451060]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	4786.3	nM	PMID[451062]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[451053]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17220.0	nM	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	2.01	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	1.89	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	2.48	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	2.64	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	1.64	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	1.84	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	1.49	n.a.	PMID[451064]
NPT2	Others	Unspecified		Ratio IC50	=	1.76	n.a.	PMID[451064]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	F	=	10.6	%	PMID[451065]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	F	=	2.1	%	PMID[451065]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[451053]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[451053]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	26679.5	nM	PMID[451053]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	6.24	%	PMID[451068]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	45.85	%	PMID[451069]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-10.15	%	PMID[451070]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.02	%	PMID[451071]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.43	%	PMID[451072]

☑ 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 NPC77000 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	306
0.1-0.2	1408
0.2-0.3	2781
0.3-0.4	8066
0.4-0.5	12373
0.5-0.6	10245
0.6-0.7	6847
0.7-0.8	627
0.8-0.85	25
0.85-0.9	8
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC238861
0.9655	High Similarity	NPC51079
0.9478	High Similarity	NPC988
0.9478	High Similarity	NPC289432
0.9397	High Similarity	NPC144547
0.9211	High Similarity	NPC135730
0.9123	High Similarity	NPC228936
0.8983	High Similarity	NPC232958
0.8947	High Similarity	NPC13784
0.8889	High Similarity	NPC310662
0.8879	High Similarity	NPC226093
0.887	High Similarity	NPC196075
0.8793	High Similarity	NPC474095
0.8707	High Similarity	NPC477411
0.8527	High Similarity	NPC212207
0.839	Intermediate Similarity	NPC326664
0.8376	Intermediate Similarity	NPC212415
0.832	Intermediate Similarity	NPC295664
0.8319	Intermediate Similarity	NPC470764
0.8264	Intermediate Similarity	NPC80605
0.8264	Intermediate Similarity	NPC323440
0.8264	Intermediate Similarity	NPC222968
0.8244	Intermediate Similarity	NPC23894
0.8235	Intermediate Similarity	NPC241851
0.8189	Intermediate Similarity	NPC51292
0.8182	Intermediate Similarity	NPC309056
0.8167	Intermediate Similarity	NPC474408
0.8154	Intermediate Similarity	NPC239134
0.8151	Intermediate Similarity	NPC143768
0.8145	Intermediate Similarity	NPC50872
0.8145	Intermediate Similarity	NPC472981
0.814	Intermediate Similarity	NPC471832
0.8136	Intermediate Similarity	NPC210089
0.8125	Intermediate Similarity	NPC115797
0.8125	Intermediate Similarity	NPC51448
0.8115	Intermediate Similarity	NPC45794
0.8115	Intermediate Similarity	NPC61651
0.811	Intermediate Similarity	NPC476599
0.8106	Intermediate Similarity	NPC474659
0.8095	Intermediate Similarity	NPC328107
0.8017	Intermediate Similarity	NPC221275
0.8015	Intermediate Similarity	NPC164295
0.8	Intermediate Similarity	NPC128368
0.8	Intermediate Similarity	NPC131684
0.7984	Intermediate Similarity	NPC204784
0.7984	Intermediate Similarity	NPC478162
0.7984	Intermediate Similarity	NPC478165
0.7983	Intermediate Similarity	NPC265513
0.7983	Intermediate Similarity	NPC137315
0.7983	Intermediate Similarity	NPC474057
0.7955	Intermediate Similarity	NPC472656
0.7955	Intermediate Similarity	NPC183103
0.7953	Intermediate Similarity	NPC85511
0.7934	Intermediate Similarity	NPC307651
0.7926	Intermediate Similarity	NPC119542
0.792	Intermediate Similarity	NPC473243
0.792	Intermediate Similarity	NPC476225
0.7917	Intermediate Similarity	NPC79496
0.7917	Intermediate Similarity	NPC471188
0.7917	Intermediate Similarity	NPC280789
0.7903	Intermediate Similarity	NPC318173
0.7899	Intermediate Similarity	NPC273837
0.7895	Intermediate Similarity	NPC203486
0.7895	Intermediate Similarity	NPC329913
0.7891	Intermediate Similarity	NPC75432
0.7881	Intermediate Similarity	NPC470391
0.7879	Intermediate Similarity	NPC472394
0.7869	Intermediate Similarity	NPC210092
0.7852	Intermediate Similarity	NPC471670
0.7851	Intermediate Similarity	NPC470253
0.7846	Intermediate Similarity	NPC428300
0.784	Intermediate Similarity	NPC202015
0.7833	Intermediate Similarity	NPC291799
0.7833	Intermediate Similarity	NPC474157
0.7829	Intermediate Similarity	NPC328997
0.7829	Intermediate Similarity	NPC470765
0.7829	Intermediate Similarity	NPC294050
0.7823	Intermediate Similarity	NPC228318
0.7815	Intermediate Similarity	NPC83628
0.7815	Intermediate Similarity	NPC265407
0.7812	Intermediate Similarity	NPC318067
0.7803	Intermediate Similarity	NPC470278
0.7797	Intermediate Similarity	NPC30594
0.7797	Intermediate Similarity	NPC37622
0.7795	Intermediate Similarity	NPC167323
0.7795	Intermediate Similarity	NPC269923
0.7787	Intermediate Similarity	NPC67377
0.7787	Intermediate Similarity	NPC196673
0.7769	Intermediate Similarity	NPC474737
0.7769	Intermediate Similarity	NPC470753
0.7769	Intermediate Similarity	NPC270699
0.7769	Intermediate Similarity	NPC473220
0.7769	Intermediate Similarity	NPC82899
0.7769	Intermediate Similarity	NPC169913
0.7761	Intermediate Similarity	NPC59459
0.7761	Intermediate Similarity	NPC126516
0.776	Intermediate Similarity	NPC254233
0.7752	Intermediate Similarity	NPC472693
0.7752	Intermediate Similarity	NPC472694
0.775	Intermediate Similarity	NPC214067
0.775	Intermediate Similarity	NPC196246
0.7746	Intermediate Similarity	NPC478163
0.7744	Intermediate Similarity	NPC279596
0.7744	Intermediate Similarity	NPC477412
0.7742	Intermediate Similarity	NPC190298
0.7731	Intermediate Similarity	NPC203732
0.7727	Intermediate Similarity	NPC147561
0.7727	Intermediate Similarity	NPC57552
0.7727	Intermediate Similarity	NPC82712
0.7724	Intermediate Similarity	NPC215419
0.7719	Intermediate Similarity	NPC239185
0.7717	Intermediate Similarity	NPC97566
0.7712	Intermediate Similarity	NPC209632
0.7712	Intermediate Similarity	NPC471186
0.771	Intermediate Similarity	NPC316553
0.7698	Intermediate Similarity	NPC476645
0.7692	Intermediate Similarity	NPC236405
0.7692	Intermediate Similarity	NPC275576
0.7692	Intermediate Similarity	NPC9180
0.7692	Intermediate Similarity	NPC100402
0.7687	Intermediate Similarity	NPC165612
0.7687	Intermediate Similarity	NPC476644
0.7686	Intermediate Similarity	NPC1082
0.7686	Intermediate Similarity	NPC167504
0.7686	Intermediate Similarity	NPC305912
0.768	Intermediate Similarity	NPC152812
0.7676	Intermediate Similarity	NPC281398
0.7674	Intermediate Similarity	NPC325740
0.7674	Intermediate Similarity	NPC472704
0.7669	Intermediate Similarity	NPC72915
0.7667	Intermediate Similarity	NPC17417
0.7667	Intermediate Similarity	NPC469636
0.7667	Intermediate Similarity	NPC10251
0.7661	Intermediate Similarity	NPC471616
0.7661	Intermediate Similarity	NPC260886
0.766	Intermediate Similarity	NPC245522
0.766	Intermediate Similarity	NPC114513
0.766	Intermediate Similarity	NPC290038
0.7652	Intermediate Similarity	NPC59502
0.7652	Intermediate Similarity	NPC134882
0.7647	Intermediate Similarity	NPC472551
0.7647	Intermediate Similarity	NPC472545
0.7642	Intermediate Similarity	NPC471721
0.7634	Intermediate Similarity	NPC177925
0.763	Intermediate Similarity	NPC470406
0.7627	Intermediate Similarity	NPC114594
0.7623	Intermediate Similarity	NPC292834
0.7609	Intermediate Similarity	NPC475400
0.7606	Intermediate Similarity	NPC478160
0.7606	Intermediate Similarity	NPC478166
0.7603	Intermediate Similarity	NPC251854
0.7603	Intermediate Similarity	NPC93084
0.7597	Intermediate Similarity	NPC472703
0.7594	Intermediate Similarity	NPC49272
0.7591	Intermediate Similarity	NPC39549
0.7591	Intermediate Similarity	NPC232996
0.7591	Intermediate Similarity	NPC307401
0.7589	Intermediate Similarity	NPC478164
0.7589	Intermediate Similarity	NPC117674
0.7586	Intermediate Similarity	NPC476042
0.7583	Intermediate Similarity	NPC56493
0.7583	Intermediate Similarity	NPC470007
0.7583	Intermediate Similarity	NPC112903
0.7581	Intermediate Similarity	NPC93181
0.7576	Intermediate Similarity	NPC72667
0.7574	Intermediate Similarity	NPC473399
0.7574	Intermediate Similarity	NPC473216
0.7569	Intermediate Similarity	NPC192069
0.7569	Intermediate Similarity	NPC95526
0.7565	Intermediate Similarity	NPC265220
0.7561	Intermediate Similarity	NPC469547
0.7561	Intermediate Similarity	NPC272524
0.7561	Intermediate Similarity	NPC93287
0.7557	Intermediate Similarity	NPC121272
0.7557	Intermediate Similarity	NPC470818
0.7556	Intermediate Similarity	NPC477406
0.7556	Intermediate Similarity	NPC477407
0.7554	Intermediate Similarity	NPC470407
0.7542	Intermediate Similarity	NPC89886
0.7542	Intermediate Similarity	NPC60679
0.7542	Intermediate Similarity	NPC301943
0.7542	Intermediate Similarity	NPC474365
0.7542	Intermediate Similarity	NPC247976
0.7541	Intermediate Similarity	NPC475002
0.7541	Intermediate Similarity	NPC95126
0.754	Intermediate Similarity	NPC268930
0.7538	Intermediate Similarity	NPC178382
0.7536	Intermediate Similarity	NPC186647
0.7536	Intermediate Similarity	NPC472395
0.7536	Intermediate Similarity	NPC471542
0.7536	Intermediate Similarity	NPC472371
0.7536	Intermediate Similarity	NPC118366
0.7535	Intermediate Similarity	NPC471451
0.7521	Intermediate Similarity	NPC474364
0.7521	Intermediate Similarity	NPC99846
0.7521	Intermediate Similarity	NPC70624
0.7521	Intermediate Similarity	NPC269023
0.7521	Intermediate Similarity	NPC109514
0.7521	Intermediate Similarity	NPC476993
0.7521	Intermediate Similarity	NPC192577

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 NPC77000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	959
0.2-0.3	1186
0.3-0.4	2765
0.4-0.5	2383
0.5-0.6	1245
0.6-0.7	301
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3412	Clinical (unspecified phase)
0.8376	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD3972	Approved
0.7727	Intermediate Similarity	NPD7008	Discontinued
0.7724	Intermediate Similarity	NPD5951	Approved
0.7719	Intermediate Similarity	NPD3495	Discontinued
0.7667	Intermediate Similarity	NPD2182	Approved
0.7519	Intermediate Similarity	NPD6287	Discontinued
0.75	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1876	Approved
0.7422	Intermediate Similarity	NPD1651	Approved
0.7419	Intermediate Similarity	NPD6858	Approved
0.7419	Intermediate Similarity	NPD7094	Approved
0.7398	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7236	Approved
0.7333	Intermediate Similarity	NPD164	Approved
0.7324	Intermediate Similarity	NPD7003	Approved
0.7288	Intermediate Similarity	NPD1238	Approved
0.7252	Intermediate Similarity	NPD1281	Approved
0.7236	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2346	Discontinued
0.7231	Intermediate Similarity	NPD2932	Approved
0.7226	Intermediate Similarity	NPD7713	Phase 3
0.7226	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD7239	Suspended
0.7197	Intermediate Similarity	NPD4878	Approved
0.7192	Intermediate Similarity	NPD6273	Approved
0.719	Intermediate Similarity	NPD5909	Discontinued
0.7177	Intermediate Similarity	NPD2067	Discontinued
0.7174	Intermediate Similarity	NPD2979	Phase 3
0.7154	Intermediate Similarity	NPD3024	Approved
0.7154	Intermediate Similarity	NPD3025	Approved
0.7132	Intermediate Similarity	NPD7055	Discontinued
0.7113	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2798	Approved
0.7109	Intermediate Similarity	NPD3317	Approved
0.7107	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1929	Approved
0.7107	Intermediate Similarity	NPD1930	Approved
0.7099	Intermediate Similarity	NPD3019	Approved
0.709	Intermediate Similarity	NPD1283	Approved
0.7087	Intermediate Similarity	NPD1241	Discontinued
0.7077	Intermediate Similarity	NPD7009	Phase 2
0.7069	Intermediate Similarity	NPD7631	Approved
0.7047	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD3023	Approved
0.7045	Intermediate Similarity	NPD3026	Approved
0.7034	Intermediate Similarity	NPD1989	Approved
0.7031	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2629	Approved
0.7023	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD2066	Phase 3
0.7	Intermediate Similarity	NPD7610	Discontinued
0.6993	Remote Similarity	NPD1471	Phase 3
0.6992	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7609	Phase 3
0.6977	Remote Similarity	NPD4198	Discontinued
0.6972	Remote Similarity	NPD2799	Discontinued
0.6966	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD2531	Phase 2
0.6923	Remote Similarity	NPD2438	Suspended
0.6911	Remote Similarity	NPD1237	Approved
0.6906	Remote Similarity	NPD2313	Discontinued
0.6906	Remote Similarity	NPD3764	Approved
0.6889	Remote Similarity	NPD5327	Phase 3
0.6875	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6663	Approved
0.6857	Remote Similarity	NPD7961	Discontinued
0.6849	Remote Similarity	NPD8166	Discontinued
0.6835	Remote Similarity	NPD6039	Approved
0.6822	Remote Similarity	NPD6010	Discontinued
0.6821	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3226	Approved
0.6818	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7741	Discontinued
0.6812	Remote Similarity	NPD5736	Approved
0.6806	Remote Similarity	NPD2796	Approved
0.6791	Remote Similarity	NPD4879	Approved
0.6788	Remote Similarity	NPD3267	Approved
0.6788	Remote Similarity	NPD3266	Approved
0.6783	Remote Similarity	NPD650	Approved
0.6781	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7057	Phase 3
0.6774	Remote Similarity	NPD7058	Phase 2
0.6767	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5585	Approved
0.6748	Remote Similarity	NPD1932	Approved
0.6741	Remote Similarity	NPD1201	Approved
0.6739	Remote Similarity	NPD2788	Approved
0.6736	Remote Similarity	NPD3748	Approved
0.6716	Remote Similarity	NPD5126	Approved
0.6716	Remote Similarity	NPD4626	Approved
0.6716	Remote Similarity	NPD5125	Phase 3
0.6716	Remote Similarity	NPD17	Approved
0.6694	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2329	Discontinued
0.669	Remote Similarity	NPD4307	Phase 2
0.669	Remote Similarity	NPD6100	Approved
0.669	Remote Similarity	NPD4140	Approved
0.669	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6645	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD2344	Approved
0.6643	Remote Similarity	NPD6832	Phase 2
0.6639	Remote Similarity	NPD1088	Approved
0.6638	Remote Similarity	NPD1087	Approved
0.6621	Remote Similarity	NPD7305	Phase 1
0.6619	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6085	Phase 2
0.6583	Remote Similarity	NPD1202	Approved
0.6583	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4476	Approved
0.6575	Remote Similarity	NPD4477	Approved
0.6573	Remote Similarity	NPD3142	Approved
0.6573	Remote Similarity	NPD3140	Approved
0.6571	Remote Similarity	NPD7084	Phase 3
0.6569	Remote Similarity	NPD1608	Approved
0.6567	Remote Similarity	NPD9545	Approved
0.6558	Remote Similarity	NPD6599	Discontinued
0.6558	Remote Similarity	NPD7028	Phase 2
0.6556	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5494	Approved
0.6541	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4618	Approved
0.6528	Remote Similarity	NPD4622	Approved
0.6522	Remote Similarity	NPD4359	Approved
0.6515	Remote Similarity	NPD4766	Approved
0.651	Remote Similarity	NPD3750	Approved
0.651	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3048	Approved
0.6508	Remote Similarity	NPD3046	Approved
0.6508	Remote Similarity	NPD3047	Approved
0.6507	Remote Similarity	NPD4308	Phase 3
0.6507	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7799	Discontinued
0.65	Remote Similarity	NPD1508	Approved
0.65	Remote Similarity	NPD4624	Approved
0.65	Remote Similarity	NPD6959	Discontinued
0.6497	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5978	Approved
0.6497	Remote Similarity	NPD5977	Approved
0.6493	Remote Similarity	NPD6065	Approved
0.6483	Remote Similarity	NPD6651	Approved
0.6483	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1607	Approved
0.6475	Remote Similarity	NPD2199	Approved
0.6475	Remote Similarity	NPD5667	Approved
0.6475	Remote Similarity	NPD2198	Approved
0.6471	Remote Similarity	NPD3672	Approved
0.6471	Remote Similarity	NPD1090	Approved
0.6471	Remote Similarity	NPD1086	Approved
0.6471	Remote Similarity	NPD1778	Approved
0.6471	Remote Similarity	NPD3673	Approved
0.6471	Remote Similarity	NPD1089	Approved
0.6467	Remote Similarity	NPD2309	Approved
0.6463	Remote Similarity	NPD2935	Discontinued
0.6458	Remote Similarity	NPD3373	Approved
0.6449	Remote Similarity	NPD6637	Approved
0.6447	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1563	Approved
0.6444	Remote Similarity	NPD3091	Approved
0.6444	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7473	Discontinued
0.6438	Remote Similarity	NPD5688	Approved
0.6438	Remote Similarity	NPD5689	Approved
0.6429	Remote Similarity	NPD6647	Phase 2
0.6423	Remote Similarity	NPD3897	Approved
0.6423	Remote Similarity	NPD3898	Approved
0.6423	Remote Similarity	NPD3896	Approved
0.6423	Remote Similarity	NPD3895	Approved
0.6418	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5735	Approved
0.6414	Remote Similarity	NPD6355	Discontinued
0.641	Remote Similarity	NPD9259	Approved
0.641	Remote Similarity	NPD9257	Approved
0.6406	Remote Similarity	NPD3134	Approved
0.6403	Remote Similarity	NPD5157	Phase 1
0.6403	Remote Similarity	NPD5159	Phase 2
0.6403	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4110	Phase 3
0.64	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1510	Phase 2
0.6393	Remote Similarity	NPD6049	Phase 2
0.6393	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2651	Approved

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