NPASS Compound

Structure

CID180006 OpenBabel06191715552D 22 23 0 0 0 0 0 0 0 0999 V2000 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -6.0622 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 16 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	327.983
LogP:	5.18
LogD:	4.217
LogS:	-5.75
# Rotatable Bonds:	6
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	2.498
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.732
MDCK Permeability:	1.9790806618402712e-05
Pgp-inhibitor:	0.704
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.312
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.11608123779297%
Volume Distribution (VD):	0.699
Pgp-substrate:	3.836439609527588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.858
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.475
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	11.498
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.832
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.9
Carcinogencity:	0.142
Eye Corrosion:	0.005
Eye Irritation:	0.921
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC180006

Natural Product ID:	NPC180006
*Common Name:**	Auraptene
IUPAC Name:	7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
Synonyms:	7-Geranyloxycoumarin; Auraptene
Standard InCHIKey:	RSDDHGSKLOSQFK-RVDMUPIBSA-N
Standard InCHI:	InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
SMILES:	CC(=CCC/C(=C/COc1ccc2ccc(=O)oc2c1)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL307341
PubChem CID:	1550607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17666859]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25522543]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO30202	Rutaceae	Genus	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[27771936]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29975532]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31471	Poncirus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9366	Rosa transmorrisonensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24248.1	Lactarius deliciosus var. deterrimus	Varieties	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27785	Atalantia buxifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1117	Hypholoma capnoides	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8528	Citrus junos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2629	Cystoseira caespitosa	Species	Sargassaceae	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
IC50	24
Ki	1
MIC	9
Others	32
Potency	40

Activity Type	# Activity
Cell Line	17
CELL-LINE	2
Individual Protein	49
NON-MOLECULAR	6
Organism	18
Others	11
PROTEIN COMPLEX	100
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	500000.0	nM	PMID[489147]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	47000.0	nM	PMID[489147]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[489150]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[489150]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[489151]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	70794.6	nM	PMID[489152]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	10000.0	nM	PMID[489150]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[489152]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PMID[489151]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[489150]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	35481.3	nM	PMID[489150]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	31622.8	nM	PMID[489152]
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	22387.2	nM	PMID[489151]
NPT501	Individual Protein	Alpha-galactosidase A	Homo sapiens	Potency	=	14125.4	nM	PMID[489152]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[489150]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[489152]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[489151]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[489152]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[489151]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	55.36	ug.mL-1	PMID[489153]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	82000.0	nM	PMID[489154]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	65000.0	nM	PMID[489154]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	87000.0	nM	PMID[489154]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	66000.0	nM	PMID[489154]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[489151]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[489151]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[489151]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	37933.0	nM	PMID[489151]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[489150]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.895	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.005	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.017	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.26	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.084	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	5.897	n.a.	PMID[489157]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	11.67	n.a.	PMID[489157]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[489151]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[489151]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[489151]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-3.79	%	PMID[489159]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[489151]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[489151]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[489151]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[489151]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	7000.0	nM	PMID[489164]
NPT4046	Individual Protein	Melatonin receptor 1A	Homo sapiens	Ki	=	1900.0	nM	PMID[489166]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	80000.0	nM	PMID[489166]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	24000.0	nM	PMID[489166]
NPT83	Cell Line	MCF7	Homo sapiens	Efficacy	=	90.0	%	PMID[489166]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Efficacy	=	67.0	%	PMID[489166]
NPT457	Cell Line	BT-549	Homo sapiens	Efficacy	=	86.0	%	PMID[489166]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	3.0	%	PMID[489166]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	-36.0	%	PMID[489166]
NPT457	Cell Line	BT-549	Homo sapiens	Inhibition	=	7.0	%	PMID[489166]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.4	mg m-1	PMID[489145]
NPT32	Organism	Mus musculus	Mus musculus	Reduction	=	51.0	%	PMID[489145]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	50.0	ug.mL-1	PMID[489146]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[489152]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[489150]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[489151]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	31622.8	nM	PMID[489151]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[489152]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	82000.0	nM	PMID[489154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	58000.0	nM	PMID[489154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	90.0	%	PMID[489154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	58.0	%	PMID[489154]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7375.3	nM	PMID[489151]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[489151]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	345100.0	nM	PMID[489156]
NPT2	Others	Unspecified		IC50	=	6300.0	nM	PMID[489158]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	23900.0	nM	PMID[489158]
NPT2	Others	Unspecified		Potency	n.a.	44668.4	nM	PMID[489151]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	1.5	%	PMID[489159]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	log(1/MIC)	=	2.16	n.a.	PMID[489160]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	>=	2048.0	ug.mL-1	PMID[489160]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>=	2048.0	ug.mL-1	PMID[489160]
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[489161]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	18800.0	nM	PMID[489161]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	10200.0	nM	PMID[489161]
NPT893	Individual Protein	Monoamine oxidase B	Mus musculus	IC50	=	0.0006	nM	PMID[489162]
NPT892	Individual Protein	Monoamine oxidase A	Mus musculus	IC50	=	0.0346	nM	PMID[489162]
NPT2	Others	Unspecified		IC50	=	0.0017	nM	PMID[489162]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[489151]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[489150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	21000.0	nM	PMID[489163]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	>	100000.0	nM	PMID[489163]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.0	n.a.	PMID[489164]
NPT2	Others	Unspecified		IC50	=	7000.0	nM	PMID[489164]
NPT2	Others	Unspecified		IC50	=	57000000.0	nM	PMID[489166]
NPT2	Others	Unspecified		Efficacy	=	57.0	%	PMID[489166]
NPT2	Others	Unspecified		Inhibition	=	5.0	%	PMID[489166]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	39.1	%	PMID[489167]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	68.4	%	PMID[489167]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	2.2	n.a.	PMID[489167]
NPT22410	CELL-LINE	Melan-a	Mus musculus	FC	=	1.3	n.a.	PMID[489168]
NPT22410	CELL-LINE	Melan-a	Mus musculus	FC	=	2.0	n.a.	PMID[489168]
NPT893	Individual Protein	Monoamine oxidase B	Mus musculus	IC50	=	600.0	nM	PMID[489171]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[489172]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[489172]

☑ 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 NPC180006 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	384
0.1-0.2	1785
0.2-0.3	5091
0.3-0.4	11111
0.4-0.5	6702
0.5-0.6	4555
0.6-0.7	6115
0.7-0.8	5043
0.8-0.85	1307
0.85-0.9	450
0.9-0.95	123
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235190
0.9825	High Similarity	NPC163200
0.9823	High Similarity	NPC281356
0.9735	High Similarity	NPC265547
0.9649	High Similarity	NPC298796
0.9573	High Similarity	NPC109675
0.9573	High Similarity	NPC273772
0.9561	High Similarity	NPC96705
0.9561	High Similarity	NPC152306
0.9558	High Similarity	NPC128633
0.9492	High Similarity	NPC201667
0.9492	High Similarity	NPC73413
0.9492	High Similarity	NPC27671
0.9487	High Similarity	NPC248429
0.9487	High Similarity	NPC96286
0.9417	High Similarity	NPC121740
0.9417	High Similarity	NPC258567
0.9417	High Similarity	NPC224774
0.9407	High Similarity	NPC472518
0.9339	High Similarity	NPC469453
0.9339	High Similarity	NPC472519
0.925	High Similarity	NPC471827
0.925	High Similarity	NPC471828
0.9244	High Similarity	NPC315807
0.9237	High Similarity	NPC144418
0.9187	High Similarity	NPC19242
0.9187	High Similarity	NPC113098
0.9174	High Similarity	NPC188327
0.9174	High Similarity	NPC234109
0.9174	High Similarity	NPC101894
0.9167	High Similarity	NPC291899
0.916	High Similarity	NPC13007
0.916	High Similarity	NPC257188
0.9113	High Similarity	NPC272650
0.9113	High Similarity	NPC29734
0.9113	High Similarity	NPC267336
0.9106	High Similarity	NPC168710
0.9098	High Similarity	NPC243688
0.9083	High Similarity	NPC290605
0.9083	High Similarity	NPC50720
0.9083	High Similarity	NPC154176
0.9083	High Similarity	NPC173350
0.9076	High Similarity	NPC52247
0.9068	High Similarity	NPC247553
0.904	High Similarity	NPC14248
0.9032	High Similarity	NPC80170
0.9024	High Similarity	NPC157212
0.9024	High Similarity	NPC185066
0.9024	High Similarity	NPC199204
0.9016	High Similarity	NPC471826
0.9008	High Similarity	NPC111347
0.9	High Similarity	NPC150214
0.8992	High Similarity	NPC319378
0.8992	High Similarity	NPC302107
0.8968	High Similarity	NPC2363
0.8968	High Similarity	NPC296624
0.8968	High Similarity	NPC318400
0.8968	High Similarity	NPC7526
0.8968	High Similarity	NPC167111
0.8968	High Similarity	NPC471910
0.8968	High Similarity	NPC31849
0.8968	High Similarity	NPC133956
0.8968	High Similarity	NPC469449
0.8968	High Similarity	NPC207002
0.8968	High Similarity	NPC36437
0.8968	High Similarity	NPC241341
0.8968	High Similarity	NPC222036
0.8968	High Similarity	NPC233018
0.8952	High Similarity	NPC474289
0.8938	High Similarity	NPC149545
0.8934	High Similarity	NPC93219
0.8934	High Similarity	NPC244495
0.8917	High Similarity	NPC187868
0.8898	High Similarity	NPC198381
0.8898	High Similarity	NPC267412
0.8898	High Similarity	NPC84894
0.8898	High Similarity	NPC195343
0.8898	High Similarity	NPC55149
0.8898	High Similarity	NPC319859
0.8898	High Similarity	NPC47163
0.8898	High Similarity	NPC74655
0.8898	High Similarity	NPC100986
0.8898	High Similarity	NPC18804
0.8898	High Similarity	NPC307412
0.8898	High Similarity	NPC166672
0.8898	High Similarity	NPC260265
0.8898	High Similarity	NPC287182
0.8898	High Similarity	NPC164269
0.8898	High Similarity	NPC127888
0.8889	High Similarity	NPC137669
0.886	High Similarity	NPC106141
0.8828	High Similarity	NPC471909
0.8828	High Similarity	NPC86892
0.8828	High Similarity	NPC471625
0.8828	High Similarity	NPC469675
0.8828	High Similarity	NPC472424
0.8828	High Similarity	NPC281241
0.878	High Similarity	NPC232692
0.878	High Similarity	NPC202594
0.877	High Similarity	NPC143725
0.8761	High Similarity	NPC157473
0.8761	High Similarity	NPC151530
0.876	High Similarity	NPC283331
0.876	High Similarity	NPC149320
0.876	High Similarity	NPC128529
0.876	High Similarity	NPC160727
0.876	High Similarity	NPC471630
0.876	High Similarity	NPC55615
0.876	High Similarity	NPC26954
0.876	High Similarity	NPC177281
0.876	High Similarity	NPC38099
0.876	High Similarity	NPC283019
0.876	High Similarity	NPC476455
0.875	High Similarity	NPC326600
0.875	High Similarity	NPC213173
0.875	High Similarity	NPC180716
0.875	High Similarity	NPC50896
0.875	High Similarity	NPC224475
0.875	High Similarity	NPC204353
0.875	High Similarity	NPC62366
0.874	High Similarity	NPC194277
0.874	High Similarity	NPC175159
0.874	High Similarity	NPC19157
0.874	High Similarity	NPC469956
0.874	High Similarity	NPC319969
0.873	High Similarity	NPC244799
0.873	High Similarity	NPC240722
0.873	High Similarity	NPC32463
0.872	High Similarity	NPC139595
0.872	High Similarity	NPC60704
0.872	High Similarity	NPC293642
0.871	High Similarity	NPC127604
0.8692	High Similarity	NPC471069
0.8692	High Similarity	NPC155963
0.8692	High Similarity	NPC131198
0.8692	High Similarity	NPC306365
0.8692	High Similarity	NPC471068
0.8692	High Similarity	NPC14697
0.8684	High Similarity	NPC291837
0.8682	High Similarity	NPC472525
0.8682	High Similarity	NPC229128
0.8673	High Similarity	NPC176971
0.8672	High Similarity	NPC163557
0.8672	High Similarity	NPC54503
0.8672	High Similarity	NPC55147
0.8672	High Similarity	NPC469955
0.8672	High Similarity	NPC469952
0.8661	High Similarity	NPC472517
0.8651	High Similarity	NPC123127
0.8651	High Similarity	NPC27239
0.864	High Similarity	NPC194841
0.864	High Similarity	NPC289316
0.8629	High Similarity	NPC168259
0.8626	High Similarity	NPC164148
0.8626	High Similarity	NPC307883
0.8626	High Similarity	NPC471070
0.8626	High Similarity	NPC279573
0.8626	High Similarity	NPC211110
0.8626	High Similarity	NPC151946
0.8626	High Similarity	NPC471071
0.8626	High Similarity	NPC43500
0.8626	High Similarity	NPC471072
0.8605	High Similarity	NPC309953
0.8605	High Similarity	NPC98179
0.8605	High Similarity	NPC253574
0.8595	High Similarity	NPC193193
0.8595	High Similarity	NPC31314
0.8595	High Similarity	NPC473290
0.8595	High Similarity	NPC471504
0.8584	High Similarity	NPC128730
0.8584	High Similarity	NPC139891
0.8571	High Similarity	NPC33717
0.8571	High Similarity	NPC474651
0.8571	High Similarity	NPC474623
0.8561	High Similarity	NPC312881
0.856	High Similarity	NPC163248
0.855	High Similarity	NPC232246
0.855	High Similarity	NPC153818
0.8538	High Similarity	NPC66705
0.8538	High Similarity	NPC33986
0.8538	High Similarity	NPC61499
0.8537	High Similarity	NPC288238
0.8534	High Similarity	NPC231251
0.8534	High Similarity	NPC25067
0.8534	High Similarity	NPC88868
0.8527	High Similarity	NPC472524
0.8516	High Similarity	NPC250727
0.8512	High Similarity	NPC59561
0.8512	High Similarity	NPC172253
0.8509	High Similarity	NPC326447
0.85	High Similarity	NPC471498
0.85	High Similarity	NPC471503
0.8496	Intermediate Similarity	NPC300611
0.8496	Intermediate Similarity	NPC152771
0.8496	Intermediate Similarity	NPC155552
0.8496	Intermediate Similarity	NPC287286
0.8496	Intermediate Similarity	NPC472523
0.8496	Intermediate Similarity	NPC195357
0.8496	Intermediate Similarity	NPC138149
0.8485	Intermediate Similarity	NPC253616

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 NPC180006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	983
0.2-0.3	1691
0.3-0.4	2685
0.4-0.5	1806
0.5-0.6	1130
0.6-0.7	351
0.7-0.8	108
0.8-0.85	31
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9076	High Similarity	NPD422	Phase 1
0.8584	High Similarity	NPD9697	Approved
0.8571	High Similarity	NPD1008	Clinical (unspecified phase)
0.8509	High Similarity	NPD3134	Approved
0.8438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5124	Phase 1
0.8295	Intermediate Similarity	NPD1296	Phase 2
0.8279	Intermediate Similarity	NPD1548	Phase 1
0.8276	Intermediate Similarity	NPD1358	Approved
0.8222	Intermediate Similarity	NPD1652	Phase 2
0.8134	Intermediate Similarity	NPD2796	Approved
0.8083	Intermediate Similarity	NPD5535	Approved
0.806	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD6832	Phase 2
0.7986	Intermediate Similarity	NPD6799	Approved
0.7969	Intermediate Similarity	NPD3225	Approved
0.792	Intermediate Similarity	NPD5691	Approved
0.7907	Intermediate Similarity	NPD2797	Approved
0.7874	Intermediate Similarity	NPD1610	Phase 2
0.7869	Intermediate Similarity	NPD1241	Discontinued
0.7863	Intermediate Similarity	NPD4908	Phase 1
0.7826	Intermediate Similarity	NPD1243	Approved
0.7795	Intermediate Similarity	NPD3496	Discontinued
0.7786	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3750	Approved
0.7769	Intermediate Similarity	NPD3266	Approved
0.7769	Intermediate Similarity	NPD3267	Approved
0.7762	Intermediate Similarity	NPD1653	Approved
0.7744	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1551	Phase 2
0.7717	Intermediate Similarity	NPD1778	Approved
0.771	Intermediate Similarity	NPD1019	Discontinued
0.7692	Intermediate Similarity	NPD920	Approved
0.7676	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD9717	Approved
0.7655	Intermediate Similarity	NPD6599	Discontinued
0.7612	Intermediate Similarity	NPD3268	Approved
0.7603	Intermediate Similarity	NPD7411	Suspended
0.7603	Intermediate Similarity	NPD2684	Approved
0.7586	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4626	Approved
0.7574	Intermediate Similarity	NPD4340	Discontinued
0.7574	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5403	Approved
0.7552	Intermediate Similarity	NPD5401	Approved
0.7551	Intermediate Similarity	NPD6801	Discontinued
0.7521	Intermediate Similarity	NPD290	Approved
0.7518	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD5585	Approved
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4749	Approved
0.7462	Intermediate Similarity	NPD1091	Approved
0.745	Intermediate Similarity	NPD3817	Phase 2
0.7431	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD9545	Approved
0.7422	Intermediate Similarity	NPD1894	Discontinued
0.741	Intermediate Similarity	NPD7033	Discontinued
0.741	Intermediate Similarity	NPD1510	Phase 2
0.74	Intermediate Similarity	NPD7768	Phase 2
0.7391	Intermediate Similarity	NPD1607	Approved
0.7388	Intermediate Similarity	NPD3018	Phase 2
0.7379	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7843	Approved
0.7353	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6798	Discontinued
0.7351	Intermediate Similarity	NPD7075	Discontinued
0.7319	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD17	Approved
0.7303	Intermediate Similarity	NPD919	Approved
0.7286	Intermediate Similarity	NPD4308	Phase 3
0.7279	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD2981	Phase 2
0.726	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7248	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1613	Approved
0.7246	Intermediate Similarity	NPD4060	Phase 1
0.7241	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD821	Approved
0.7219	Intermediate Similarity	NPD5402	Approved
0.7218	Intermediate Similarity	NPD2983	Phase 2
0.7218	Intermediate Similarity	NPD4359	Approved
0.7218	Intermediate Similarity	NPD2982	Phase 2
0.7214	Intermediate Similarity	NPD2200	Suspended
0.7209	Intermediate Similarity	NPD5536	Phase 2
0.7206	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1611	Approved
0.7194	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7157	Approved
0.7188	Intermediate Similarity	NPD2557	Approved
0.7185	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6233	Phase 2
0.7172	Intermediate Similarity	NPD6666	Approved
0.7172	Intermediate Similarity	NPD6667	Approved
0.7171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8651	Approved
0.7163	Intermediate Similarity	NPD2799	Discontinued
0.7154	Intermediate Similarity	NPD968	Approved
0.7153	Intermediate Similarity	NPD7466	Approved
0.7153	Intermediate Similarity	NPD3027	Phase 3
0.7153	Intermediate Similarity	NPD5163	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7132	Intermediate Similarity	NPD2237	Approved
0.7132	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2861	Phase 2
0.7132	Intermediate Similarity	NPD9493	Approved
0.7132	Intermediate Similarity	NPD3596	Phase 2
0.7124	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7212	Phase 2
0.7123	Intermediate Similarity	NPD7213	Phase 3
0.7122	Intermediate Similarity	NPD4140	Approved
0.7121	Intermediate Similarity	NPD3847	Discontinued
0.712	Intermediate Similarity	NPD5451	Approved
0.7113	Intermediate Similarity	NPD2935	Discontinued
0.7105	Intermediate Similarity	NPD4288	Approved
0.7101	Intermediate Similarity	NPD411	Approved
0.7101	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1048	Approved
0.7095	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7447	Phase 1
0.7071	Intermediate Similarity	NPD447	Suspended
0.7071	Intermediate Similarity	NPD230	Phase 1
0.707	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4380	Phase 2
0.7059	Intermediate Similarity	NPD3882	Suspended
0.7054	Intermediate Similarity	NPD6671	Approved
0.705	Intermediate Similarity	NPD4062	Phase 3
0.7044	Intermediate Similarity	NPD5844	Phase 1
0.7039	Intermediate Similarity	NPD2801	Approved
0.7039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5746	Approved
0.7027	Intermediate Similarity	NPD2186	Approved
0.7023	Intermediate Similarity	NPD6580	Approved
0.7023	Intermediate Similarity	NPD6581	Approved
0.7018	Intermediate Similarity	NPD1282	Approved
0.7015	Intermediate Similarity	NPD3972	Approved
0.7014	Intermediate Similarity	NPD2424	Discontinued
0.7013	Intermediate Similarity	NPD3749	Approved
0.7013	Intermediate Similarity	NPD6971	Discontinued
0.7007	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD3140	Approved
0.7	Intermediate Similarity	NPD3142	Approved
0.6993	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD4476	Approved
0.6993	Remote Similarity	NPD4477	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6978	Remote Similarity	NPD2313	Discontinued
0.6975	Remote Similarity	NPD7549	Discontinued
0.6974	Remote Similarity	NPD1934	Approved
0.6972	Remote Similarity	NPD7097	Phase 1
0.697	Remote Similarity	NPD3443	Approved
0.697	Remote Similarity	NPD3049	Approved
0.697	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3445	Approved
0.697	Remote Similarity	NPD3444	Approved
0.6966	Remote Similarity	NPD2654	Approved
0.6962	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2534	Approved
0.6959	Remote Similarity	NPD2533	Approved
0.6959	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD2614	Approved
0.695	Remote Similarity	NPD4618	Approved
0.695	Remote Similarity	NPD4622	Approved
0.6944	Remote Similarity	NPD6004	Phase 3
0.6944	Remote Similarity	NPD6005	Phase 3
0.6944	Remote Similarity	NPD5762	Approved
0.6944	Remote Similarity	NPD5763	Approved
0.6944	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6002	Phase 3
0.694	Remote Similarity	NPD3705	Approved
0.694	Remote Similarity	NPD1535	Discovery
0.6939	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3690	Phase 2
0.6934	Remote Similarity	NPD2798	Approved
0.6934	Remote Similarity	NPD3691	Phase 2
0.6929	Remote Similarity	NPD5745	Approved
0.6929	Remote Similarity	NPD8032	Phase 2
0.6923	Remote Similarity	NPD5494	Approved
0.6917	Remote Similarity	NPD2556	Approved
0.6917	Remote Similarity	NPD6516	Phase 2
0.6917	Remote Similarity	NPD2554	Approved
0.6917	Remote Similarity	NPD5846	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