NPASS Compound

Structure

CID41178 OpenBabel06191715372D 25 29 0 0 1 0 0 0 0 0999 V2000 -7.0132 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 21 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 15 2 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.15
Volume:	342.033
LogP:	2.956
LogD:	3.056
LogS:	-2.468
# Rotatable Bonds:	2
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	2.982
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	2.9034506951575167e-05
Pgp-inhibitor:	0.132
Pgp-substrate:	0.619
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	95.43671417236328%
Volume Distribution (VD):	1.226
Pgp-substrate:	3.1314616203308105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.817
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.971
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	16.129
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.368
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.605
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.212
Carcinogencity:	0.9
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC41178

Natural Product ID:	NPC41178
*Common Name:**	Tetrahydroberberine
IUPAC Name:	n.a.
Synonyms:	Tetrahydroberberine
Standard InCHIKey:	VZTUIEROBZXUFA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3
SMILES:	COc1ccc2CC3c4cc5c(cc4CCN3Cc2c1OC)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL275097
PubChem CID:	34458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21094631]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27143	Rhizoma corydalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	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
AC50	3
EC50	3
GI50	115
IC50	9
Ki	1
Others	17
Potency	23

Activity Type	# Activity
Cell Line	122
Individual Protein	15
NUCLEIC-ACID	1
Organism	11
Others	21
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[496075]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	25.0	%	PMID[496075]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50000.0	nM	PMID[496076]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[496077]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[496077]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	27940.0	nM	PMID[496077]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	30000.0	nM	PMID[496077]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[496078]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[496078]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	25.0	%	PMID[496079]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	562.3	nM	PMID[496078]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	79983.43	nM	PMID[496080]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	60953.69	nM	PMID[496081]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[496081]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	68706.84	nM	PMID[496080]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	30831.88	nM	PMID[496080]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	76032.63	nM	PMID[496081]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496080]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[496081]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[496078]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[496078]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	12762.2	nM	PMID[496083]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11374.3	nM	PMID[496083]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	125892.5	nM	PMID[496078]
NPT219	Individual Protein	Alpha-1a adrenergic receptor	Rattus norvegicus	Ki	=	1122.02	nM	PMID[496085]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	45.0	%	PMID[496089]
NPT681	Cell Line	PC-12	Rattus norvegicus	CC50	>	150000.0	nM	PMID[496090]
NPT2	Others	Unspecified		EC50	>	60000.0	nM	PMID[496078]
NPT2	Others	Unspecified		EC50	=	3430.0	nM	PMID[496078]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PMID[496078]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1471.6	nM	PMID[496078]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[496078]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[496078]
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	8.35	nM	PMID[496082]
NPT2	Others	Unspecified		AC50	n.a.	44668.4	nM	PMID[496084]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[496078]
NPT2	Others	Unspecified		Ac50	n.a.	39.81	uM	PMID[496084]
NPT2	Others	Unspecified		Ac50	n.a.	44.67	uM	PMID[496084]
NPT2	Others	Unspecified		Ac50	n.a.	31.62	uM	PMID[496084]
NPT2	Others	Unspecified		AC50	n.a.	39810.7	nM	PMID[496084]
NPT2	Others	Unspecified		AC50	n.a.	31622.8	nM	PMID[496084]
NPT35	Others	n.a.		Activity	=	1577.0	equiv	PMID[496086]
NPT24744	NUCLEIC-ACID	DNA	Bacteria	EC50	=	93000.0	nM	PMID[496086]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	7.87	%	PMID[496087]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	-1.05	%	PMID[496087]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-13.18	%	PMID[496087]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	10.57	%	PMID[496087]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-8.62	%	PMID[496087]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	-2.26	%	PMID[496087]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	8.62	%	PMID[496087]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[496088]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[496088]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	-28.0	%	PMID[496090]
NPT35	Others	n.a.		Solubility	=	7000.0	nM	PMID[496090]
NPT2	Others	Unspecified		Potency	n.a.	6434.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	18832.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5353.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9022.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12744.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	403	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14299.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11358.8	nM	PubChem BioAssay data set

☑ 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 NPC41178 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	316
0.1-0.2	1554
0.2-0.3	8255
0.3-0.4	9757
0.4-0.5	6611
0.5-0.6	11821
0.6-0.7	3364
0.7-0.8	591
0.8-0.85	257
0.85-0.9	123
0.9-0.95	38
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216459
1.0	High Similarity	NPC138487
0.9932	High Similarity	NPC146288
0.9796	High Similarity	NPC31311
0.9796	High Similarity	NPC234392
0.9592	High Similarity	NPC233029
0.9592	High Similarity	NPC210148
0.9586	High Similarity	NPC475959
0.9539	High Similarity	NPC238530
0.9539	High Similarity	NPC276944
0.9539	High Similarity	NPC232514
0.9517	High Similarity	NPC476144
0.9517	High Similarity	NPC106295
0.9517	High Similarity	NPC16107
0.9517	High Similarity	NPC210437
0.9517	High Similarity	NPC51957
0.9452	High Similarity	NPC7467
0.9333	High Similarity	NPC93593
0.9276	High Similarity	NPC111485
0.9241	High Similarity	NPC136860
0.9241	High Similarity	NPC128019
0.9241	High Similarity	NPC476567
0.9216	High Similarity	NPC477559
0.9216	High Similarity	NPC266753
0.9216	High Similarity	NPC160298
0.9216	High Similarity	NPC306902
0.9216	High Similarity	NPC232924
0.9177	High Similarity	NPC2314
0.915	High Similarity	NPC477080
0.9103	High Similarity	NPC24264
0.9103	High Similarity	NPC474915
0.9103	High Similarity	NPC476432
0.9103	High Similarity	NPC328750
0.9103	High Similarity	NPC188163
0.9103	High Similarity	NPC213206
0.9079	High Similarity	NPC193949
0.9079	High Similarity	NPC110416
0.9079	High Similarity	NPC204828
0.9079	High Similarity	NPC184026
0.9079	High Similarity	NPC207757
0.9079	High Similarity	NPC276588
0.9079	High Similarity	NPC295691
0.9079	High Similarity	NPC39701
0.9079	High Similarity	NPC127674
0.9079	High Similarity	NPC54379
0.9079	High Similarity	NPC189266
0.9079	High Similarity	NPC278799
0.9079	High Similarity	NPC2413
0.9079	High Similarity	NPC5238
0.9079	High Similarity	NPC469817
0.9079	High Similarity	NPC249797
0.9079	High Similarity	NPC172765
0.9045	High Similarity	NPC247389
0.9038	High Similarity	NPC225774
0.9038	High Similarity	NPC302527
0.9038	High Similarity	NPC167546
0.9038	High Similarity	NPC16805
0.9034	High Similarity	NPC314682
0.8981	High Similarity	NPC219341
0.8954	High Similarity	NPC78733
0.8947	High Similarity	NPC148898
0.8924	High Similarity	NPC298979
0.8924	High Similarity	NPC210918
0.8903	High Similarity	NPC106786
0.8868	High Similarity	NPC241055
0.8867	High Similarity	NPC476151
0.8861	High Similarity	NPC86144
0.8861	High Similarity	NPC304659
0.8854	High Similarity	NPC59567
0.8841	High Similarity	NPC299990
0.8841	High Similarity	NPC73492
0.8828	High Similarity	NPC7018
0.8816	High Similarity	NPC151895
0.8816	High Similarity	NPC97221
0.8816	High Similarity	NPC220858
0.8816	High Similarity	NPC192768
0.8816	High Similarity	NPC88249
0.8797	High Similarity	NPC168409
0.8773	High Similarity	NPC118633
0.8773	High Similarity	NPC294790
0.8773	High Similarity	NPC148693
0.8758	High Similarity	NPC81733
0.8758	High Similarity	NPC149090
0.8758	High Similarity	NPC19520
0.8758	High Similarity	NPC326316
0.875	High Similarity	NPC103379
0.875	High Similarity	NPC477565
0.8734	High Similarity	NPC189470
0.8733	High Similarity	NPC185838
0.871	High Similarity	NPC76079
0.8696	High Similarity	NPC75958
0.8696	High Similarity	NPC6152
0.8684	High Similarity	NPC147390
0.8684	High Similarity	NPC476571
0.8684	High Similarity	NPC246587
0.8684	High Similarity	NPC428
0.8684	High Similarity	NPC135538
0.8684	High Similarity	NPC24233
0.8683	High Similarity	NPC477259
0.8683	High Similarity	NPC169387
0.8659	High Similarity	NPC320223
0.8659	High Similarity	NPC114364
0.8654	High Similarity	NPC247639
0.8654	High Similarity	NPC25084
0.865	High Similarity	NPC199465
0.865	High Similarity	NPC229166
0.865	High Similarity	NPC128560
0.8627	High Similarity	NPC219162
0.8627	High Similarity	NPC92541
0.8625	High Similarity	NPC13916
0.8625	High Similarity	NPC264850
0.8618	High Similarity	NPC179825
0.8618	High Similarity	NPC191376
0.8618	High Similarity	NPC321505
0.8609	High Similarity	NPC130926
0.8608	High Similarity	NPC215829
0.8608	High Similarity	NPC97072
0.8599	High Similarity	NPC476572
0.859	High Similarity	NPC99659
0.859	High Similarity	NPC80129
0.859	High Similarity	NPC325871
0.859	High Similarity	NPC187022
0.859	High Similarity	NPC244112
0.858	High Similarity	NPC281581
0.8571	High Similarity	NPC223125
0.8562	High Similarity	NPC59907
0.8562	High Similarity	NPC130941
0.8562	High Similarity	NPC37144
0.8562	High Similarity	NPC231198
0.8562	High Similarity	NPC24465
0.8554	High Similarity	NPC179704
0.8529	High Similarity	NPC473716
0.8529	High Similarity	NPC475597
0.8528	High Similarity	NPC65403
0.8519	High Similarity	NPC266176
0.8519	High Similarity	NPC82533
0.8519	High Similarity	NPC158148
0.8519	High Similarity	NPC290759
0.8516	High Similarity	NPC476568
0.8516	High Similarity	NPC476579
0.8503	High Similarity	NPC248642
0.8497	Intermediate Similarity	NPC253883
0.8497	Intermediate Similarity	NPC90844
0.8497	Intermediate Similarity	NPC95075
0.8497	Intermediate Similarity	NPC144863
0.8494	Intermediate Similarity	NPC27887
0.8494	Intermediate Similarity	NPC126284
0.8487	Intermediate Similarity	NPC145304
0.848	Intermediate Similarity	NPC24260
0.8466	Intermediate Similarity	NPC152212
0.8466	Intermediate Similarity	NPC311991
0.8462	Intermediate Similarity	NPC223124
0.8457	Intermediate Similarity	NPC57812
0.8457	Intermediate Similarity	NPC474324
0.8457	Intermediate Similarity	NPC100566
0.8452	Intermediate Similarity	NPC156576
0.8447	Intermediate Similarity	NPC247972
0.8443	Intermediate Similarity	NPC32413
0.8443	Intermediate Similarity	NPC474506
0.8438	Intermediate Similarity	NPC24954
0.8434	Intermediate Similarity	NPC23219
0.8428	Intermediate Similarity	NPC216816
0.8424	Intermediate Similarity	NPC187678
0.8418	Intermediate Similarity	NPC170503
0.8418	Intermediate Similarity	NPC203784
0.8418	Intermediate Similarity	NPC126519
0.8415	Intermediate Similarity	NPC115284
0.8415	Intermediate Similarity	NPC317439
0.8415	Intermediate Similarity	NPC225597
0.8415	Intermediate Similarity	NPC276890
0.8415	Intermediate Similarity	NPC227060
0.8415	Intermediate Similarity	NPC10908
0.8415	Intermediate Similarity	NPC317145
0.8415	Intermediate Similarity	NPC76682
0.8415	Intermediate Similarity	NPC198498
0.8415	Intermediate Similarity	NPC477640
0.8415	Intermediate Similarity	NPC470739
0.8415	Intermediate Similarity	NPC63646
0.8414	Intermediate Similarity	NPC160193
0.8408	Intermediate Similarity	NPC2295
0.8408	Intermediate Similarity	NPC477564
0.8405	Intermediate Similarity	NPC475686
0.8405	Intermediate Similarity	NPC58766
0.8405	Intermediate Similarity	NPC475845
0.8393	Intermediate Similarity	NPC275132
0.8393	Intermediate Similarity	NPC116284
0.8387	Intermediate Similarity	NPC60538
0.8387	Intermediate Similarity	NPC211296
0.8387	Intermediate Similarity	NPC207824
0.8385	Intermediate Similarity	NPC475393
0.8385	Intermediate Similarity	NPC320104
0.8383	Intermediate Similarity	NPC267408
0.8383	Intermediate Similarity	NPC258695
0.8383	Intermediate Similarity	NPC244554
0.8383	Intermediate Similarity	NPC470879
0.8382	Intermediate Similarity	NPC477258
0.8378	Intermediate Similarity	NPC11147
0.8375	Intermediate Similarity	NPC27410
0.8375	Intermediate Similarity	NPC166014
0.8373	Intermediate Similarity	NPC112575

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 NPC41178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	746
0.2-0.3	1023
0.3-0.4	1870
0.4-0.5	2665
0.5-0.6	1800
0.6-0.7	659
0.7-0.8	163
0.8-0.85	21
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD4584	Approved
0.9103	High Similarity	NPD4664	Clinical (unspecified phase)
0.859	High Similarity	NPD7298	Approved
0.8543	High Similarity	NPD5084	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD8252	Approved
0.8415	Intermediate Similarity	NPD8251	Approved
0.8415	Intermediate Similarity	NPD8099	Discontinued
0.8397	Intermediate Similarity	NPD4017	Approved
0.8387	Intermediate Similarity	NPD3641	Approved
0.8387	Intermediate Similarity	NPD3640	Phase 3
0.8387	Intermediate Similarity	NPD3639	Approved
0.8366	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD8156	Discontinued
0.8291	Intermediate Similarity	NPD4773	Phase 2
0.8291	Intermediate Similarity	NPD4772	Phase 2
0.8267	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6031	Approved
0.8153	Intermediate Similarity	NPD6030	Approved
0.811	Intermediate Similarity	NPD6107	Approved
0.8086	Intermediate Similarity	NPD6788	Approved
0.807	Intermediate Similarity	NPD8054	Approved
0.807	Intermediate Similarity	NPD8053	Approved
0.8049	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5718	Phase 2
0.7964	Intermediate Similarity	NPD4481	Phase 3
0.7962	Intermediate Similarity	NPD3124	Discontinued
0.7952	Intermediate Similarity	NPD4166	Phase 2
0.7933	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4420	Approved
0.7857	Intermediate Similarity	NPD2898	Approved
0.7844	Intermediate Similarity	NPD4010	Discontinued
0.7844	Intermediate Similarity	NPD3051	Approved
0.7834	Intermediate Similarity	NPD5241	Discontinued
0.7824	Intermediate Similarity	NPD5313	Approved
0.7824	Intermediate Similarity	NPD5312	Approved
0.7803	Intermediate Similarity	NPD7280	Phase 3
0.7803	Intermediate Similarity	NPD7281	Phase 3
0.7802	Intermediate Similarity	NPD5006	Approved
0.7802	Intermediate Similarity	NPD5005	Approved
0.7798	Intermediate Similarity	NPD2970	Approved
0.7798	Intermediate Similarity	NPD2969	Approved
0.7784	Intermediate Similarity	NPD7802	Discontinued
0.7751	Intermediate Similarity	NPD2489	Approved
0.7751	Intermediate Similarity	NPD27	Approved
0.7744	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6071	Discontinued
0.7733	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6896	Approved
0.7727	Intermediate Similarity	NPD6895	Approved
0.7711	Intermediate Similarity	NPD7831	Phase 2
0.7711	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7833	Phase 2
0.7697	Intermediate Similarity	NPD2563	Approved
0.7697	Intermediate Similarity	NPD4474	Approved
0.7697	Intermediate Similarity	NPD4475	Approved
0.7697	Intermediate Similarity	NPD2560	Approved
0.7688	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2492	Phase 1
0.7636	Intermediate Similarity	NPD2978	Approved
0.7636	Intermediate Similarity	NPD2977	Approved
0.763	Intermediate Similarity	NPD6297	Approved
0.7625	Intermediate Similarity	NPD2420	Approved
0.7625	Intermediate Similarity	NPD2421	Approved
0.7625	Intermediate Similarity	NPD7598	Phase 2
0.7619	Intermediate Similarity	NPD3815	Phase 1
0.7619	Intermediate Similarity	NPD3816	Phase 1
0.7602	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5977	Approved
0.759	Intermediate Similarity	NPD5978	Approved
0.7578	Intermediate Similarity	NPD1424	Approved
0.7547	Intermediate Similarity	NPD6748	Discontinued
0.7541	Intermediate Similarity	NPD8095	Phase 1
0.7532	Intermediate Similarity	NPD3110	Approved
0.7532	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3109	Approved
0.7531	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5604	Discontinued
0.7485	Intermediate Similarity	NPD4727	Phase 1
0.7484	Intermediate Similarity	NPD5177	Phase 3
0.7473	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6851	Approved
0.7458	Intermediate Similarity	NPD6853	Approved
0.7438	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5754	Discontinued
0.743	Intermediate Similarity	NPD7906	Approved
0.741	Intermediate Similarity	NPD7110	Phase 1
0.741	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7313	Approved
0.7401	Intermediate Similarity	NPD7312	Approved
0.7401	Intermediate Similarity	NPD7310	Approved
0.7401	Intermediate Similarity	NPD7311	Approved
0.7401	Intermediate Similarity	NPD2968	Approved
0.7401	Intermediate Similarity	NPD2971	Approved
0.7396	Intermediate Similarity	NPD4055	Discovery
0.7375	Intermediate Similarity	NPD4236	Phase 3
0.7375	Intermediate Similarity	NPD4237	Approved
0.7371	Intermediate Similarity	NPD3885	Approved
0.736	Intermediate Similarity	NPD7309	Approved
0.736	Intermediate Similarity	NPD6618	Phase 2
0.7346	Intermediate Similarity	NPD7124	Phase 2
0.7346	Intermediate Similarity	NPD3845	Phase 1
0.7333	Intermediate Similarity	NPD3349	Phase 2
0.7329	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5457	Discontinued
0.7303	Intermediate Similarity	NPD4577	Approved
0.7303	Intermediate Similarity	NPD4578	Approved
0.7283	Intermediate Similarity	NPD5582	Discontinued
0.7283	Intermediate Similarity	NPD6687	Approved
0.7283	Intermediate Similarity	NPD6688	Approved
0.7278	Intermediate Similarity	NPD4663	Approved
0.7273	Intermediate Similarity	NPD5976	Discontinued
0.7273	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4162	Approved
0.7255	Intermediate Similarity	NPD7247	Discontinued
0.7251	Intermediate Similarity	NPD7400	Phase 3
0.7247	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7291	Discontinued
0.7237	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4108	Discontinued
0.7229	Intermediate Similarity	NPD4210	Discontinued
0.7209	Intermediate Similarity	NPD5677	Discontinued
0.7207	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4098	Discontinued
0.716	Intermediate Similarity	NPD3384	Approved
0.716	Intermediate Similarity	NPD3060	Approved
0.716	Intermediate Similarity	NPD3383	Approved
0.716	Intermediate Similarity	NPD3382	Approved
0.7159	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2488	Approved
0.7158	Intermediate Similarity	NPD2490	Approved
0.7158	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD6875	Approved
0.7143	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6876	Approved
0.7143	Intermediate Similarity	NPD7905	Discontinued
0.7135	Intermediate Similarity	NPD4859	Phase 1
0.7135	Intermediate Similarity	NPD6493	Phase 3
0.7134	Intermediate Similarity	NPD2674	Phase 3
0.7133	Intermediate Similarity	NPD2668	Approved
0.7133	Intermediate Similarity	NPD2667	Approved
0.7125	Intermediate Similarity	NPD1753	Discontinued
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7121	Intermediate Similarity	NPD3763	Approved
0.712	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5772	Approved
0.7118	Intermediate Similarity	NPD5773	Approved
0.7108	Intermediate Similarity	NPD6090	Discontinued
0.7107	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2232	Approved
0.7105	Intermediate Similarity	NPD2233	Approved
0.7105	Intermediate Similarity	NPD2230	Approved
0.7104	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4005	Discontinued
0.7079	Intermediate Similarity	NPD3920	Phase 2
0.7076	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5160	Discontinued
0.7073	Intermediate Similarity	NPD3692	Discontinued
0.707	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1914	Approved
0.7063	Intermediate Similarity	NPD7119	Phase 2
0.7062	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2974	Approved
0.7059	Intermediate Similarity	NPD5720	Discontinued
0.7059	Intermediate Similarity	NPD1421	Approved
0.7059	Intermediate Similarity	NPD2973	Approved
0.7059	Intermediate Similarity	NPD2975	Approved
0.7059	Intermediate Similarity	NPD1420	Approved
0.7056	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3656	Approved
0.7037	Intermediate Similarity	NPD1375	Discontinued
0.7035	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2120	Phase 2
0.7027	Intermediate Similarity	NPD3921	Approved
0.7027	Intermediate Similarity	NPD3922	Approved
0.7027	Intermediate Similarity	NPD3924	Approved
0.7027	Intermediate Similarity	NPD3923	Approved
0.7025	Intermediate Similarity	NPD3531	Approved
0.7025	Intermediate Similarity	NPD3532	Approved
0.7025	Intermediate Similarity	NPD3530	Approved
0.7022	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4585	Approved
0.7012	Intermediate Similarity	NPD6331	Phase 2
0.7011	Intermediate Similarity	NPD6037	Discontinued
0.7	Intermediate Similarity	NPD2653	Approved
0.7	Intermediate Similarity	NPD6386	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