NPASS Compound

Structure

CID201731 OpenBabel06191715592D 30 33 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 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 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 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 -5.1962 -3.0000 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 -3.5000 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 -0.0000 -2.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -4.3301 -1.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 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 -3.4641 -3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 13 19 2 0 0 0 0 13 29 1 0 0 0 0 15 19 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	424.317
LogP:	6.207
LogD:	4.058
LogS:	-2.409
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	3.139
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.696
MDCK Permeability:	2.0208823116263375e-05
Pgp-inhibitor:	0.392
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.87069702148438%
Volume Distribution (VD):	0.531
Pgp-substrate:	3.1985976696014404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.608
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.516
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	3.575
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.562
Skin Sensitization:	0.499
Carcinogencity:	0.852
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.321

Download Data

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

Natural Product: NPC201731

Natural Product ID:	NPC201731
*Common Name:**	Osajin
IUPAC Name:	5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	DCTLJGWMHPGCOS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3
SMILES:	CC(=CCc1c(c2c(=O)c(coc2c2C=CC(C)(C)Oc12)c1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL238188
PubChem CID:	95168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26101	Andropogon zizanioides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26671	Hapalosiphon welwitschii	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28994	Acacia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19038	Zanha golungensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4859	Hosta kiyosumiensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25806	Streptomyces violaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26778	Lophophora lewinii	Species	Cactaceae	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	1
GI50	7
IC50	9
Ki	2
LD50	1
Others	100
Potency	75

Activity Type	# Activity
Cell Line	11
Individual Protein	65
NON-MOLECULAR	5
Organism	100
Others	17
Protein Family	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	12320.0	nM	PMID[465895]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	12130.0	nM	PMID[465895]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	11970.0	nM	PMID[465895]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	11340.0	nM	PMID[465895]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	10980.0	nM	PMID[465895]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	9650.0	nM	PMID[465895]
NPT611	Cell Line	Hepatocyte	Homo sapiens	GI50	>	500000.0	nM	PMID[465895]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	35481.3	nM	PMID[465896]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	15848.9	nM	PMID[465896]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7079.5	nM	PMID[465896]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3162.3	nM	PMID[465897]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	31622.8	nM	PMID[465896]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	22387.2	nM	PMID[465897]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[465896]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	10000.0	nM	PMID[465896]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	12589.3	nM	PMID[465897]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[465897]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[465896]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[465897]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	28183.8	nM	PMID[465897]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PMID[465896]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	15848.9	nM	PMID[465897]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PMID[465897]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	876.0	nM	PMID[465896]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	12589.3	nM	PMID[465896]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	10000.0	nM	PMID[465896]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[465897]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	15848.9	nM	PMID[465896]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[465896]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[465896]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[465896]
NPT1098	Individual Protein	Eyes absent homolog 2	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[465896]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[465896]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[465896]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[465896]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[465897]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[465896]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[465897]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4.6	nM	PMID[465896]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[465896]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[465896]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[465896]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[465896]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[465896]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[465897]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[465896]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[465896]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[465897]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[465896]
NPT1182	Cell Line	J774.A1	Mus musculus	FC	=	1.59	n.a.	PMID[465901]
NPT1182	Cell Line	J774.A1	Mus musculus	FC	=	0.95	n.a.	PMID[465901]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	3210.0	nM	PMID[465902]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	3060.0	nM	PMID[465902]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[465896]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[465896]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[465896]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[465896]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[465896]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	23600.0	nM	PMID[465904]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	29900.0	nM	PMID[465904]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	11440.0	nM	PMID[465905]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	IC50	=	6530.0	nM	PMID[465895]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	1469.0	nM	PMID[465896]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	1112.0	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PMID[465897]
NPT2	Others	Unspecified		Concentration @ Maxi	=	50.0	um	PMID[465896]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	11220.2	nM	PMID[465897]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	19952.6	nM	PMID[465896]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	25118.9	nM	PMID[465897]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[465897]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	=	16360.1	nM	PMID[465896]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	15848.9	nM	PMID[465897]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	10000.0	nM	PMID[465897]
NPT2	Others	Unspecified		EC50	=	16600.0	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[465896]
NPT2	Others	Unspecified		EC50	>	80000.0	nM	PMID[465896]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[465896]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[465896]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[465896]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[465896]
NPT2	Others	Unspecified		Potency	n.a.	891.3	nM	PMID[465896]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[465896]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LC50	=	0.26	ug.mL-1	PMID[465898]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	100.0	%	PMID[465898]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	LC50	=	0.32	ug.mL-1	PMID[465898]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	100.0	%	PMID[465898]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	LC50	=	0.28	ug.mL-1	PMID[465898]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	mortality	=	100.0	%	PMID[465898]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	LC50	=	0.29	ug.mL-1	PMID[465898]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	100.0	%	PMID[465898]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	18.0	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	2.9	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	10.0	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	15.7	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	47.8	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	45.6	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	584.8	mg	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	504.8	mg	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	331.2	hr	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	372.0	hr	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	12.2	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	33.4	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	249.6	hr	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	268.8	hr	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	LD50	=	3.54	microg/cm2	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	98.2	%	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	ED50	=	3.18	microg/cm2	PMID[465899]
NPT2747	Organism	Achaea janata	Achaea janata	AFI	=	100.0	%	PMID[465899]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	mortality	<=	7.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	54.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	71.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	44.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	50.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	85.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	43.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	156.0	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	172.8	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	151.2	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	163.2	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	170.4	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	182.4	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	153.6	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	175.2	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	103.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	76.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	104.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	75.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	102.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	109.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	71.0	mg	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	280.8	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	273.6	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	302.4	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	283.2	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	297.6	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	TIME	=	271.2	hr	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-1.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	6.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	6.3	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	1.9	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	4.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	4.7	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	1.7	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	3.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-7.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-8.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	23.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	36.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	27.5	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-1.4	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	2.6	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	17.6	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	10.8	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-2.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-3.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	17.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	7.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	10.5	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	-12.0	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	30.5	%	PMID[465900]
NPT4065	Organism	Ostrinia nubilalis	Ostrinia nubilalis	Activity	=	27.7	%	PMID[465900]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[465896]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31000.0	nM	PMID[465901]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.0	%	PMID[465901]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	1000000.0	nM	PMID[465901]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	39.0	%	PMID[465901]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	112.92	%	PMID[465903]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	88.68	%	PMID[465903]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[465897]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[465897]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[465897]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[465897]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[465896]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	3870.0	nM	PMID[465905]
NPT27	Others	Unspecified		Selectivity index	=	2.95	n.a.	PMID[465905]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[465906]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[465906]

☑ 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 NPC201731 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	394
0.1-0.2	1633
0.2-0.3	3783
0.3-0.4	10167
0.4-0.5	8428
0.5-0.6	3772
0.6-0.7	5836
0.7-0.8	4650
0.8-0.85	2066
0.85-0.9	1367
0.9-0.95	503
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97716
1.0	High Similarity	NPC237635
1.0	High Similarity	NPC104406
1.0	High Similarity	NPC24673
1.0	High Similarity	NPC79469
0.9929	High Similarity	NPC6511
0.9929	High Similarity	NPC266572
0.979	High Similarity	NPC188403
0.972	High Similarity	NPC5173
0.9718	High Similarity	NPC23728
0.9718	High Similarity	NPC110303
0.9718	High Similarity	NPC296998
0.9718	High Similarity	NPC473077
0.9716	High Similarity	NPC319752
0.9716	High Similarity	NPC311741
0.9716	High Similarity	NPC234629
0.9714	High Similarity	NPC62840
0.9714	High Similarity	NPC299080
0.9714	High Similarity	NPC59739
0.9714	High Similarity	NPC217083
0.9714	High Similarity	NPC78803
0.9714	High Similarity	NPC226636
0.9714	High Similarity	NPC11561
0.9714	High Similarity	NPC214236
0.9714	High Similarity	NPC293852
0.965	High Similarity	NPC160821
0.965	High Similarity	NPC132592
0.965	High Similarity	NPC244407
0.965	High Similarity	NPC161191
0.965	High Similarity	NPC321623
0.965	High Similarity	NPC189087
0.9648	High Similarity	NPC176229
0.9648	High Similarity	NPC475052
0.9648	High Similarity	NPC111786
0.9648	High Similarity	NPC312973
0.9648	High Similarity	NPC470647
0.9648	High Similarity	NPC301276
0.9648	High Similarity	NPC54577
0.9648	High Similarity	NPC474161
0.9648	High Similarity	NPC246948
0.9648	High Similarity	NPC88964
0.9648	High Similarity	NPC476088
0.9648	High Similarity	NPC142405
0.9648	High Similarity	NPC195621
0.9648	High Similarity	NPC267375
0.9648	High Similarity	NPC20488
0.9648	High Similarity	NPC67805
0.9648	High Similarity	NPC83357
0.9648	High Similarity	NPC214774
0.9645	High Similarity	NPC18585
0.9645	High Similarity	NPC106985
0.9645	High Similarity	NPC166138
0.9645	High Similarity	NPC219915
0.9645	High Similarity	NPC38219
0.9643	High Similarity	NPC156590
0.9643	High Similarity	NPC110969
0.9643	High Similarity	NPC205006
0.9643	High Similarity	NPC118840
0.9643	High Similarity	NPC147688
0.9643	High Similarity	NPC64908
0.9643	High Similarity	NPC103362
0.9583	High Similarity	NPC474052
0.958	High Similarity	NPC14001
0.958	High Similarity	NPC283234
0.958	High Similarity	NPC166757
0.9577	High Similarity	NPC209040
0.9574	High Similarity	NPC144499
0.9571	High Similarity	NPC159275
0.9571	High Similarity	NPC204985
0.9571	High Similarity	NPC172986
0.9571	High Similarity	NPC215311
0.9571	High Similarity	NPC172250
0.9571	High Similarity	NPC150522
0.9571	High Similarity	NPC259166
0.9571	High Similarity	NPC219917
0.9571	High Similarity	NPC48624
0.9571	High Similarity	NPC213659
0.9571	High Similarity	NPC305355
0.9571	High Similarity	NPC235239
0.9571	High Similarity	NPC144118
0.9571	High Similarity	NPC261227
0.9571	High Similarity	NPC80962
0.9571	High Similarity	NPC241100
0.9571	High Similarity	NPC326109
0.9571	High Similarity	NPC475680
0.9571	High Similarity	NPC270883
0.9524	High Similarity	NPC470681
0.9517	High Similarity	NPC471115
0.9517	High Similarity	NPC472633
0.9517	High Similarity	NPC29777
0.9517	High Similarity	NPC61258
0.9514	High Similarity	NPC168085
0.9514	High Similarity	NPC296869
0.951	High Similarity	NPC477955
0.951	High Similarity	NPC220418
0.951	High Similarity	NPC124729
0.9507	High Similarity	NPC164980
0.9507	High Similarity	NPC221432
0.9507	High Similarity	NPC91560
0.9507	High Similarity	NPC478086
0.9507	High Similarity	NPC75049
0.9507	High Similarity	NPC310130
0.9507	High Similarity	NPC149026
0.9507	High Similarity	NPC169591
0.9507	High Similarity	NPC68104
0.9507	High Similarity	NPC214166
0.9507	High Similarity	NPC175504
0.9507	High Similarity	NPC316816
0.9507	High Similarity	NPC257097
0.9507	High Similarity	NPC150408
0.9507	High Similarity	NPC39329
0.9507	High Similarity	NPC143896
0.9504	High Similarity	NPC3188
0.9504	High Similarity	NPC282300
0.9504	High Similarity	NPC52789
0.9504	High Similarity	NPC469404
0.9504	High Similarity	NPC268204
0.9504	High Similarity	NPC55832
0.9504	High Similarity	NPC26051
0.95	High Similarity	NPC96565
0.95	High Similarity	NPC301217
0.95	High Similarity	NPC220062
0.95	High Similarity	NPC303633
0.95	High Similarity	NPC283429
0.95	High Similarity	NPC217186
0.95	High Similarity	NPC295384
0.95	High Similarity	NPC18260
0.95	High Similarity	NPC473076
0.95	High Similarity	NPC55018
0.95	High Similarity	NPC53181
0.95	High Similarity	NPC216978
0.95	High Similarity	NPC23257
0.95	High Similarity	NPC78913
0.9459	High Similarity	NPC282307
0.9459	High Similarity	NPC170026
0.9456	High Similarity	NPC223701
0.9456	High Similarity	NPC7989
0.9456	High Similarity	NPC472583
0.9448	High Similarity	NPC317492
0.9448	High Similarity	NPC473016
0.9444	High Similarity	NPC180477
0.9441	High Similarity	NPC273538
0.9441	High Similarity	NPC216538
0.9441	High Similarity	NPC197252
0.9441	High Similarity	NPC257236
0.9441	High Similarity	NPC236766
0.9441	High Similarity	NPC131568
0.9441	High Similarity	NPC179970
0.9441	High Similarity	NPC278175
0.9441	High Similarity	NPC473013
0.9441	High Similarity	NPC469953
0.9441	High Similarity	NPC224714
0.9441	High Similarity	NPC131579
0.9441	High Similarity	NPC473015
0.9441	High Similarity	NPC271288
0.9437	High Similarity	NPC76338
0.9437	High Similarity	NPC306829
0.9437	High Similarity	NPC220998
0.9437	High Similarity	NPC228504
0.9437	High Similarity	NPC227579
0.9437	High Similarity	NPC78
0.9437	High Similarity	NPC166482
0.9437	High Similarity	NPC223500
0.9437	High Similarity	NPC328164
0.9437	High Similarity	NPC107572
0.9437	High Similarity	NPC177354
0.9437	High Similarity	NPC64915
0.9437	High Similarity	NPC265040
0.9437	High Similarity	NPC182852
0.9437	High Similarity	NPC10937
0.9437	High Similarity	NPC40833
0.9437	High Similarity	NPC125855
0.9437	High Similarity	NPC296917
0.9437	High Similarity	NPC1089
0.9437	High Similarity	NPC324436
0.9437	High Similarity	NPC76372
0.9437	High Similarity	NPC148757
0.9437	High Similarity	NPC66515
0.9437	High Similarity	NPC32739
0.9437	High Similarity	NPC324134
0.9437	High Similarity	NPC161506
0.9437	High Similarity	NPC194432
0.9437	High Similarity	NPC147145
0.9437	High Similarity	NPC37496
0.9437	High Similarity	NPC166934
0.9437	High Similarity	NPC167624
0.9433	High Similarity	NPC253822
0.9433	High Similarity	NPC471587
0.9433	High Similarity	NPC101366
0.9433	High Similarity	NPC69769
0.9429	High Similarity	NPC201395
0.9429	High Similarity	NPC124269
0.9429	High Similarity	NPC131130
0.9429	High Similarity	NPC17848
0.9429	High Similarity	NPC21350
0.9388	High Similarity	NPC31627
0.9388	High Similarity	NPC476238
0.9388	High Similarity	NPC285623
0.9388	High Similarity	NPC327269
0.9379	High Similarity	NPC208303

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 NPC201731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	972
0.2-0.3	1490
0.3-0.4	2588
0.4-0.5	2001
0.5-0.6	1157
0.6-0.7	390
0.7-0.8	134
0.8-0.85	43
0.85-0.9	18
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9441	High Similarity	NPD7410	Clinical (unspecified phase)
0.9441	High Similarity	NPD4378	Clinical (unspecified phase)
0.9214	High Similarity	NPD1510	Phase 2
0.9155	High Similarity	NPD1549	Phase 2
0.9149	High Similarity	NPD2796	Approved
0.9122	High Similarity	NPD4380	Phase 2
0.9085	High Similarity	NPD1552	Clinical (unspecified phase)
0.9085	High Similarity	NPD1550	Clinical (unspecified phase)
0.906	High Similarity	NPD7411	Suspended
0.9007	High Similarity	NPD8443	Clinical (unspecified phase)
0.894	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD1240	Approved
0.8889	High Similarity	NPD7075	Discontinued
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8816	High Similarity	NPD7819	Suspended
0.8803	High Similarity	NPD1607	Approved
0.8766	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD6801	Discontinued
0.8701	High Similarity	NPD7768	Phase 2
0.8671	High Similarity	NPD7852	Clinical (unspecified phase)
0.8639	High Similarity	NPD3750	Approved
0.8627	High Similarity	NPD1934	Approved
0.8591	High Similarity	NPD6799	Approved
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD7421	Clinical (unspecified phase)
0.8509	High Similarity	NPD7804	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6959	Discontinued
0.8477	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD5403	Approved
0.8408	Intermediate Similarity	NPD3749	Approved
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8367	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1243	Approved
0.8322	Intermediate Similarity	NPD2800	Approved
0.8302	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD920	Approved
0.8299	Intermediate Similarity	NPD3748	Approved
0.8289	Intermediate Similarity	NPD5401	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5953	Discontinued
0.8176	Intermediate Similarity	NPD2799	Discontinued
0.8171	Intermediate Similarity	NPD7054	Approved
0.817	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2313	Discontinued
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD7472	Approved
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD2344	Approved
0.8061	Intermediate Similarity	NPD7286	Phase 2
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD6559	Discontinued
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7973	Intermediate Similarity	NPD5124	Phase 1
0.7973	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD7033	Discontinued
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1203	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7901	Intermediate Similarity	NPD919	Approved
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7877	Intermediate Similarity	NPD6832	Phase 2
0.787	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2798	Approved
0.7857	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD2309	Approved
0.7848	Intermediate Similarity	NPD3226	Approved
0.7829	Intermediate Similarity	NPD4360	Phase 2
0.7829	Intermediate Similarity	NPD4363	Phase 3
0.7815	Intermediate Similarity	NPD4308	Phase 3
0.7805	Intermediate Similarity	NPD1247	Approved
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD3268	Approved
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.774	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3225	Approved
0.7712	Intermediate Similarity	NPD2346	Discontinued
0.7708	Intermediate Similarity	NPD9717	Approved
0.7684	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4361	Phase 2
0.7671	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD422	Phase 1
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7607	Intermediate Similarity	NPD4288	Approved
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7588	Intermediate Similarity	NPD1729	Discontinued
0.7584	Intermediate Similarity	NPD4625	Phase 3
0.7554	Intermediate Similarity	NPD7584	Approved
0.755	Intermediate Similarity	NPD4307	Phase 2
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7531	Intermediate Similarity	NPD5889	Approved
0.7531	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2654	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9545	Approved
0.7469	Intermediate Similarity	NPD6585	Discontinued
0.7466	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7003	Approved
0.744	Intermediate Similarity	NPD5710	Approved
0.744	Intermediate Similarity	NPD5711	Approved
0.7432	Intermediate Similarity	NPD3267	Approved
0.7432	Intermediate Similarity	NPD3266	Approved
0.7419	Intermediate Similarity	NPD5406	Approved
0.7419	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD5408	Approved
0.7419	Intermediate Similarity	NPD5404	Approved
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3764	Approved
0.7401	Intermediate Similarity	NPD4287	Approved
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD6844	Discontinued
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1164	Approved
0.7315	Intermediate Similarity	NPD1470	Approved
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7303	Intermediate Similarity	NPD1296	Phase 2
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6104	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7289	Intermediate Similarity	NPD2296	Approved
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD7577	Discontinued
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7177	Discontinued
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7222	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7213	Phase 3
0.7205	Intermediate Similarity	NPD7212	Phase 2
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4477	Approved
0.7197	Intermediate Similarity	NPD4476	Approved
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2354	Approved
0.7188	Intermediate Similarity	NPD3887	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7169	Intermediate Similarity	NPD6280	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