NPASS Compound

Structure

NPC473803 OpenBabel07101719252D 46 53 0 0 1 0 0 0 0 0999 V2000 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 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 -4.3301 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 0.6691 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 -4.6665 -4.0827 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 -3.4641 -1.0000 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 2 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 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3902 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0593 2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -3.9781 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 22 2 0 0 0 0 5 46 1 0 0 0 0 6 13 2 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 7 20 2 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 39 1 0 0 0 0 11 40 1 0 0 0 0 12 41 1 0 0 0 0 12 42 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 10 1 6 0 0 0 16 24 1 0 0 0 0 16 28 1 0 0 0 0 17 18 2 0 0 0 0 17 41 1 0 0 0 0 18 42 1 0 0 0 0 19 25 2 0 0 0 0 19 37 1 0 0 0 0 20 25 1 0 0 0 0 20 38 1 0 0 0 0 21 11 1 6 0 0 0 21 29 1 0 0 0 0 21 43 1 0 0 0 0 22 46 1 0 0 0 0 23 13 1 1 0 0 0 23 24 1 0 0 0 0 24 30 1 1 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 26 34 1 6 0 0 0 27 32 1 0 0 0 0 27 35 1 1 0 0 0 28 44 1 6 0 0 0 29 45 1 1 0 0 0 30 36 2 0 0 0 0 30 39 1 0 0 0 0 31 22 1 1 0 0 0 31 40 1 0 0 0 0 31 45 1 0 0 0 0 32 43 1 0 0 0 0 32 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.16
Volume:	602.63
LogP:	2.421
LogD:	2.456
LogS:	-4.014
# Rotatable Bonds:	6
TPSA:	160.83
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	5.002
Fsp3:	0.469
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.694
MDCK Permeability:	4.730122600449249e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	97.32493591308594%
Volume Distribution (VD):	0.44
Pgp-substrate:	1.2101109027862549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.329
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	1.896
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.947
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.299
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC473803

Natural Product ID:	NPC473803
*Common Name:**	Teniposide
IUPAC Name:	(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Synonyms:	Teniposide; VM-26; Vumon
Standard InCHIKey:	NRUKOCRGYNPUPR-QBPJDGROSA-N
Standard InCHI:	InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
SMILES:	COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452231
PubChem CID:	452548
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones [CHEMONTID:0000047] Podophyllotoxins

*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
NPO3003	Linum flavum	Species	Linaceae	Eukaryota	root	n.a.	n.a.	PMID[1602298]
NPO3003	Linum flavum	Species	Linaceae	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
ED50	3
IC50	23
LD50	1
Others	92

Activity Type	# Activity
Cell Line	21
CELL-LINE	4
Individual Protein	8
NON-MOLECULAR	8
Organism	9
Others	39
PHENOTYPE	26
Protein Family	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Log CR	=	1.56	n.a.	PMID[502372]
NPT3950	Cell Line	GLC4 cell line		IC50	=	480.0	nM	PMID[502373]
NPT3950	Cell Line	GLC4 cell line		IC50	=	2800.0	nM	PMID[502373]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	REC	>	1000.0	n.a.	PMID[502374]
NPT1986	Cell Line	RPMI 8402	Homo sapiens	IC50	=	220.0	nM	PMID[502374]
NPT1986	Cell Line	RPMI 8402	Homo sapiens	IC50	=	280.0	nM	PMID[502374]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	REC	>	1000.0	n.a.	PMID[502375]
NPT1986	Cell Line	RPMI 8402	Homo sapiens	IC50	=	220.0	nM	PMID[502375]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[502377]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	125.0	nM	PMID[502391]
NPT6398	Cell Line	22RV1	Homo sapiens	IC50	=	82.0	nM	PMID[502391]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	IC50	>	133000.0	nM	PMID[502392]
NPT1249	Individual Protein	Canalicular multispecific organic anion transporter 2	Homo sapiens	IC50	=	20600.0	nM	PMID[502392]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	34900.0	nM	PMID[502392]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4300.0	nM	PMID[502394]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8200.0	nM	PMID[502394]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	12200.0	nM	PMID[502394]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11100.0	nM	PMID[502394]
NPT1059	Cell Line	HMEC	Homo sapiens	IC50	=	12400.0	nM	PMID[502394]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	14900.0	nM	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	>	20.0	%	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	86.0	%	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	71.0	%	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	ED50	=	40.46	mg.kg-1	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	259.15	mm3	PMID[502394]
NPT65	Cell Line	HepG2	Homo sapiens	TGI	=	48.0	%	PMID[502394]
NPT35	Others	n.a.		LogP	=	2.8	n.a.	PMID[502371]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Pc	=	0.0000002	cm s-1	PMID[502371]
NPT35	Others	n.a.		LogD	=	1.22	n.a.	PMID[502372]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	REC	>	100.0	n.a.	PMID[502374]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	280.0	nM	PMID[502375]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	DSB	=	346.0	n.a.	PMID[502376]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.06	ug ml-1	PMID[502377]
NPT605	Organism	Homo sapiens	Homo sapiens	CL	=	0.19	mL.min-1.kg-1	PMID[502380]
NPT605	Organism	Homo sapiens	Homo sapiens	CL_renal	=	0.02	mL.min-1.kg-1	PMID[502380]
NPT35	Others	n.a.		LogP	=	1.5	n.a.	PMID[502381]
NPT27	Others	Unspecified		MRT	=	37.0	hr	PMID[502382]
NPT27	Others	Unspecified		CL	=	0.19	mL.min-1.kg-1	PMID[502382]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Fu	=	0.0044	n.a.	PMID[502382]
NPT27	Others	Unspecified		Vdss	=	0.41	L.kg-1	PMID[502382]
NPT27	Others	Unspecified		T1/2	=	16.0	hr	PMID[502382]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	Composite Activity - Active	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	Composite Activity - Marginal	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	Alkaline Phosphatase Increase - Index Value	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	Alkaline Phosphatase Increase - Number of Reports	<	4.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	SGOT Increase - Index Value	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	SGOT Increase - Number of Reports	<	4.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	SGPT Increase - Index Value	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	SGPT Increase - Number of Reports	<	4.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	LDH Increase - Index Value	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	LDH Increase - Number of Reports	<	4.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	GGT Increase - Index Value	=	0.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	GGT Increase - Number of Reports	<	4.0	n.a.	PMID[502384]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_bilirubinemia	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholecystitis	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholelithiasis	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cirrhosis	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_elevated liver function tests	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic failure	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic necrosis	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatitis	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatomegaly	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_jaundice	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver disease	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver fatty	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver function tests abnormal	=	0.0	n.a.	PMID[502385]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_Combined Scores	=	0.0	n.a.	PMID[502385]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	32.58	%	PMID[502388]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	25.44	%	PMID[502388]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	4.0	n.a.	PMID[502389]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	23.8	%	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (acute)	=	0.0	n.a.	PMID[502389]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (acute)	=	0.0	%	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (cytolytic)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (choleostasis)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (severe hepatitis)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (chronic liver disease)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (cirrhosis)	=	0.0	n.a.	PMID[502389]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (granulomatous hepatitis)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (association with vascular disease)	=	1.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (steatosis)	=	0.0	n.a.	PMID[502389]
NPT2	Others	Unspecified		Hepatotoxicity (malignant tumour)	=	0.0	n.a.	PMID[502389]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (benign tumour)	=	0.0	n.a.	PMID[502389]
NPT27	Others	Unspecified		Ratio	=	117.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	2.1	n.a.	PMID[502390]
NPT27	Others	Unspecified		Papp	=	4.4	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Papp	=	2.0	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	9.8	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	54.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	21.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	70.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	50.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	8.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	84.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Papp	=	8.8	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Papp	=	0.9	ucm/s	PMID[502390]
NPT605	Organism	Homo sapiens	Homo sapiens	Fabs	=	0.0	%	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	6.9	n.a.	PMID[502390]
NPT27	Others	Unspecified		Papp	=	9.6	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Papp	=	1.4	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	5.4	n.a.	PMID[502390]
NPT27	Others	Unspecified		Papp	=	8.2	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Papp	=	1.5	ucm/s	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	78.0	n.a.	PMID[502390]
NPT27	Others	Unspecified		Ratio	=	53.0	n.a.	PMID[502390]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	>	133000.0	nM	PMID[502392]
NPT605	Organism	Homo sapiens	Homo sapiens	DILI_severity_class	=	3.0	n.a.	PMID[502393]
NPT21742	CELL-LINE	L02	Homo sapiens	IC50	=	11500.0	nM	PMID[502394]
NPT2	Others	Unspecified		IC50	=	22300.0	nM	PMID[502394]
NPT21742	CELL-LINE	L02	Homo sapiens	Activity	=	84.0	%	PMID[502394]
NPT21742	CELL-LINE	L02	Homo sapiens	Activity	=	88.0	%	PMID[502394]
NPT27	Others	Unspecified		LD50	=	46.12	mg.kg-1	PMID[502394]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC50	=	62700.0	nM	PMID[502394]
NPT21742	CELL-LINE	L02	Homo sapiens	Activity	=	98.3	%	PMID[502394]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	15.66	%	PMID[502395]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.46	%	PMID[502396]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[502397]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[502397]

☑ 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 NPC473803 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	404
0.1-0.2	1721
0.2-0.3	3733
0.3-0.4	8586
0.4-0.5	10218
0.5-0.6	7758
0.6-0.7	8305
0.7-0.8	1944
0.8-0.85	22
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8729	High Similarity	NPC179240
0.8722	High Similarity	NPC185498
0.8564	High Similarity	NPC306475
0.8556	High Similarity	NPC116759
0.8556	High Similarity	NPC14294
0.8444	Intermediate Similarity	NPC100465
0.8444	Intermediate Similarity	NPC152424
0.8389	Intermediate Similarity	NPC268718
0.8389	Intermediate Similarity	NPC91634
0.8389	Intermediate Similarity	NPC150943
0.8343	Intermediate Similarity	NPC288149
0.8306	Intermediate Similarity	NPC222531
0.8287	Intermediate Similarity	NPC96593
0.8242	Intermediate Similarity	NPC115624
0.8222	Intermediate Similarity	NPC32373
0.8222	Intermediate Similarity	NPC237946
0.8177	Intermediate Similarity	NPC207584
0.8177	Intermediate Similarity	NPC181168
0.8177	Intermediate Similarity	NPC163527
0.8177	Intermediate Similarity	NPC19947
0.8177	Intermediate Similarity	NPC115281
0.8111	Intermediate Similarity	NPC103197
0.8111	Intermediate Similarity	NPC30009
0.8087	Intermediate Similarity	NPC119910
0.8056	Intermediate Similarity	NPC178574
0.8056	Intermediate Similarity	NPC65591
0.8056	Intermediate Similarity	NPC245948
0.8031	Intermediate Similarity	NPC114120
0.8031	Intermediate Similarity	NPC167045
0.7969	Intermediate Similarity	NPC275690
0.7969	Intermediate Similarity	NPC161609
0.7949	Intermediate Similarity	NPC313063
0.7949	Intermediate Similarity	NPC286301
0.7944	Intermediate Similarity	NPC210642
0.7944	Intermediate Similarity	NPC13985
0.7929	Intermediate Similarity	NPC476358
0.7917	Intermediate Similarity	NPC35266
0.7912	Intermediate Similarity	NPC136757
0.7884	Intermediate Similarity	NPC117911
0.7872	Intermediate Similarity	NPC59516
0.7865	Intermediate Similarity	NPC469397
0.7861	Intermediate Similarity	NPC25889
0.7857	Intermediate Similarity	NPC299706
0.7857	Intermediate Similarity	NPC245615
0.7857	Intermediate Similarity	NPC115466
0.7857	Intermediate Similarity	NPC61604
0.7835	Intermediate Similarity	NPC188217
0.7835	Intermediate Similarity	NPC53680
0.7835	Intermediate Similarity	NPC208797
0.7833	Intermediate Similarity	NPC216223
0.7833	Intermediate Similarity	NPC145569
0.7833	Intermediate Similarity	NPC174512
0.7833	Intermediate Similarity	NPC262455
0.7833	Intermediate Similarity	NPC474965
0.7833	Intermediate Similarity	NPC668
0.7833	Intermediate Similarity	NPC293757
0.7833	Intermediate Similarity	NPC477695
0.7833	Intermediate Similarity	NPC177476
0.7826	Intermediate Similarity	NPC478055
0.7814	Intermediate Similarity	NPC273578
0.7812	Intermediate Similarity	NPC475244
0.7812	Intermediate Similarity	NPC193377
0.7802	Intermediate Similarity	NPC56184
0.7802	Intermediate Similarity	NPC477699
0.7801	Intermediate Similarity	NPC312006
0.7801	Intermediate Similarity	NPC129930
0.7801	Intermediate Similarity	NPC471920
0.7801	Intermediate Similarity	NPC292712
0.7801	Intermediate Similarity	NPC471922
0.7801	Intermediate Similarity	NPC114550
0.7801	Intermediate Similarity	NPC474075
0.7801	Intermediate Similarity	NPC471921
0.7801	Intermediate Similarity	NPC20114
0.779	Intermediate Similarity	NPC182368
0.779	Intermediate Similarity	NPC469706
0.779	Intermediate Similarity	NPC9933
0.779	Intermediate Similarity	NPC260781
0.779	Intermediate Similarity	NPC149505
0.779	Intermediate Similarity	NPC214326
0.779	Intermediate Similarity	NPC185955
0.779	Intermediate Similarity	NPC469707
0.779	Intermediate Similarity	NPC145979
0.779	Intermediate Similarity	NPC225815
0.779	Intermediate Similarity	NPC218041
0.779	Intermediate Similarity	NPC24425
0.7778	Intermediate Similarity	NPC174734
0.7778	Intermediate Similarity	NPC474042
0.7772	Intermediate Similarity	NPC67629
0.7772	Intermediate Similarity	NPC79736
0.7772	Intermediate Similarity	NPC472723
0.7772	Intermediate Similarity	NPC38699
0.7772	Intermediate Similarity	NPC238834
0.7772	Intermediate Similarity	NPC196771
0.7772	Intermediate Similarity	NPC186316
0.776	Intermediate Similarity	NPC184624
0.776	Intermediate Similarity	NPC316539
0.7754	Intermediate Similarity	NPC109061
0.7747	Intermediate Similarity	NPC164082
0.7747	Intermediate Similarity	NPC477700
0.7742	Intermediate Similarity	NPC173726
0.7742	Intermediate Similarity	NPC241600
0.7737	Intermediate Similarity	NPC311912
0.7732	Intermediate Similarity	NPC267549
0.7732	Intermediate Similarity	NPC80360
0.7732	Intermediate Similarity	NPC260300
0.773	Intermediate Similarity	NPC163635
0.773	Intermediate Similarity	NPC11411
0.7722	Intermediate Similarity	NPC101755
0.7722	Intermediate Similarity	NPC304687
0.7722	Intermediate Similarity	NPC65574
0.7722	Intermediate Similarity	NPC80230
0.7722	Intermediate Similarity	NPC104024
0.772	Intermediate Similarity	NPC473630
0.772	Intermediate Similarity	NPC469354
0.7708	Intermediate Similarity	NPC469777
0.7708	Intermediate Similarity	NPC473697
0.7708	Intermediate Similarity	NPC295941
0.7708	Intermediate Similarity	NPC135334
0.7708	Intermediate Similarity	NPC469775
0.7708	Intermediate Similarity	NPC469778
0.7708	Intermediate Similarity	NPC100925
0.7708	Intermediate Similarity	NPC469772
0.7708	Intermediate Similarity	NPC32723
0.7708	Intermediate Similarity	NPC469773
0.7708	Intermediate Similarity	NPC469776
0.7708	Intermediate Similarity	NPC469774
0.7705	Intermediate Similarity	NPC476434
0.7705	Intermediate Similarity	NPC478268
0.7696	Intermediate Similarity	NPC197708
0.7696	Intermediate Similarity	NPC88557
0.7696	Intermediate Similarity	NPC658
0.7692	Intermediate Similarity	NPC229882
0.7692	Intermediate Similarity	NPC158635
0.7692	Intermediate Similarity	NPC195114
0.768	Intermediate Similarity	NPC297574
0.7672	Intermediate Similarity	NPC121290
0.7668	Intermediate Similarity	NPC105137
0.7667	Intermediate Similarity	NPC3982
0.7667	Intermediate Similarity	NPC212890
0.7663	Intermediate Similarity	NPC473236
0.7663	Intermediate Similarity	NPC474606
0.766	Intermediate Similarity	NPC124747
0.766	Intermediate Similarity	NPC139540
0.766	Intermediate Similarity	NPC149873
0.766	Intermediate Similarity	NPC7191
0.766	Intermediate Similarity	NPC177100
0.766	Intermediate Similarity	NPC155754
0.765	Intermediate Similarity	NPC264302
0.765	Intermediate Similarity	NPC32079
0.7647	Intermediate Similarity	NPC215400
0.7647	Intermediate Similarity	NPC7543
0.7647	Intermediate Similarity	NPC230531
0.7647	Intermediate Similarity	NPC98083
0.7647	Intermediate Similarity	NPC478269
0.7647	Intermediate Similarity	NPC94220
0.7647	Intermediate Similarity	NPC24339
0.7647	Intermediate Similarity	NPC166456
0.7644	Intermediate Similarity	NPC167231
0.7644	Intermediate Similarity	NPC475453
0.7644	Intermediate Similarity	NPC473531
0.7644	Intermediate Similarity	NPC215802
0.7644	Intermediate Similarity	NPC79322
0.7638	Intermediate Similarity	NPC7839
0.7638	Intermediate Similarity	NPC142291
0.7637	Intermediate Similarity	NPC55158
0.7637	Intermediate Similarity	NPC51328
0.7637	Intermediate Similarity	NPC125570
0.7637	Intermediate Similarity	NPC477698
0.7637	Intermediate Similarity	NPC286235
0.7634	Intermediate Similarity	NPC165483
0.7634	Intermediate Similarity	NPC228357
0.7629	Intermediate Similarity	NPC469438
0.7619	Intermediate Similarity	NPC198796
0.7619	Intermediate Similarity	NPC22130
0.7619	Intermediate Similarity	NPC246024
0.7619	Intermediate Similarity	NPC116838
0.7617	Intermediate Similarity	NPC5786
0.7617	Intermediate Similarity	NPC102851
0.7614	Intermediate Similarity	NPC473776
0.7614	Intermediate Similarity	NPC473205
0.7611	Intermediate Similarity	NPC286245
0.7611	Intermediate Similarity	NPC272619
0.7611	Intermediate Similarity	NPC477702
0.7609	Intermediate Similarity	NPC471154
0.7609	Intermediate Similarity	NPC472611
0.7609	Intermediate Similarity	NPC472612
0.7609	Intermediate Similarity	NPC302610
0.7609	Intermediate Similarity	NPC289967
0.7609	Intermediate Similarity	NPC21902
0.7606	Intermediate Similarity	NPC100936
0.7606	Intermediate Similarity	NPC1253
0.7606	Intermediate Similarity	NPC470637
0.7602	Intermediate Similarity	NPC80956
0.7602	Intermediate Similarity	NPC93685
0.7602	Intermediate Similarity	NPC108191
0.7592	Intermediate Similarity	NPC471923
0.7592	Intermediate Similarity	NPC83049
0.7592	Intermediate Similarity	NPC9309
0.7592	Intermediate Similarity	NPC118162
0.7592	Intermediate Similarity	NPC320471

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 NPC473803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	814
0.2-0.3	1910
0.3-0.4	2930
0.4-0.5	2040
0.5-0.6	839
0.6-0.7	233
0.7-0.8	24
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7680	Approved
0.8722	High Similarity	NPD7228	Approved
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8235	Intermediate Similarity	NPD7240	Approved
0.8222	Intermediate Similarity	NPD4966	Approved
0.8222	Intermediate Similarity	NPD4965	Approved
0.8222	Intermediate Similarity	NPD4967	Phase 2
0.8056	Intermediate Similarity	NPD37	Approved
0.7889	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7229	Phase 3
0.7385	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD7054	Approved
0.7296	Intermediate Similarity	NPD7472	Approved
0.7249	Intermediate Similarity	NPD8455	Phase 2
0.7236	Intermediate Similarity	NPD8313	Approved
0.7236	Intermediate Similarity	NPD8312	Approved
0.7194	Intermediate Similarity	NPD3818	Discontinued
0.7186	Intermediate Similarity	NPD7808	Phase 3
0.7173	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7685	Pre-registration
0.7136	Intermediate Similarity	NPD7251	Discontinued
0.7136	Intermediate Similarity	NPD6559	Discontinued
0.71	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6166	Phase 2
0.7085	Intermediate Similarity	NPD6797	Phase 2
0.7085	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6232	Discontinued
0.7073	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7266	Discontinued
0.6985	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8151	Discontinued
0.6943	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6674	Discontinued
0.6919	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1653	Approved
0.6891	Remote Similarity	NPD1465	Phase 2
0.6853	Remote Similarity	NPD8127	Discontinued
0.6835	Remote Similarity	NPD8152	Approved
0.6835	Remote Similarity	NPD8153	Approved
0.6804	Remote Similarity	NPD7827	Phase 1
0.6786	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3027	Phase 3
0.6758	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7783	Phase 2
0.6753	Remote Similarity	NPD1934	Approved
0.6749	Remote Similarity	NPD5953	Discontinued
0.6738	Remote Similarity	NPD1652	Phase 2
0.6734	Remote Similarity	NPD3787	Discontinued
0.6733	Remote Similarity	NPD7286	Phase 2
0.6718	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD5494	Approved
0.6684	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6842	Approved
0.6683	Remote Similarity	NPD6843	Phase 3
0.6683	Remote Similarity	NPD6959	Discontinued
0.6683	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD2862	Discontinued
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7819	Suspended
0.6633	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7440	Discontinued
0.6614	Remote Similarity	NPD8166	Discontinued
0.6601	Remote Similarity	NPD3751	Discontinued
0.6599	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7696	Phase 3
0.659	Remote Similarity	NPD7698	Approved
0.659	Remote Similarity	NPD7697	Approved
0.6579	Remote Similarity	NPD6190	Approved
0.6566	Remote Similarity	NPD3882	Suspended
0.6564	Remote Similarity	NPD4380	Phase 2
0.6561	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7874	Approved
0.656	Remote Similarity	NPD8319	Approved
0.656	Remote Similarity	NPD8320	Phase 1
0.656	Remote Similarity	NPD7871	Phase 2
0.656	Remote Similarity	NPD7870	Phase 2
0.6559	Remote Similarity	NPD7097	Phase 1
0.6559	Remote Similarity	NPD5886	Approved
0.6559	Remote Similarity	NPD41	Approved
0.6548	Remote Similarity	NPD2801	Approved
0.6545	Remote Similarity	NPD7701	Phase 2
0.6544	Remote Similarity	NPD6823	Phase 2
0.6533	Remote Similarity	NPD6971	Discontinued
0.6533	Remote Similarity	NPD7075	Discontinued
0.6528	Remote Similarity	NPD6776	Approved
0.6528	Remote Similarity	NPD6778	Approved
0.6528	Remote Similarity	NPD6779	Approved
0.6528	Remote Similarity	NPD6782	Approved
0.6528	Remote Similarity	NPD6780	Approved
0.6528	Remote Similarity	NPD6781	Approved
0.6528	Remote Similarity	NPD6777	Approved
0.6515	Remote Similarity	NPD3817	Phase 2
0.6502	Remote Similarity	NPD8462	Phase 1
0.6495	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2531	Phase 2
0.6482	Remote Similarity	NPD7768	Phase 2
0.648	Remote Similarity	NPD7028	Phase 2
0.6477	Remote Similarity	NPD2532	Approved
0.6477	Remote Similarity	NPD2534	Approved
0.6477	Remote Similarity	NPD2533	Approved
0.6476	Remote Similarity	NPD8150	Discontinued
0.6476	Remote Similarity	NPD8434	Phase 2
0.6467	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7801	Approved
0.645	Remote Similarity	NPD3749	Approved
0.6449	Remote Similarity	NPD2746	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2745	Approved
0.6448	Remote Similarity	NPD4908	Phase 1
0.6448	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7700	Phase 2
0.6435	Remote Similarity	NPD7699	Phase 2
0.6432	Remote Similarity	NPD7296	Approved
0.6429	Remote Similarity	NPD7458	Discontinued
0.6429	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7137	Phase 2
0.6398	Remote Similarity	NPD3620	Phase 2
0.6398	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5006	Approved
0.6393	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5005	Approved
0.6382	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6597	Approved
0.6377	Remote Similarity	NPD6598	Approved
0.6372	Remote Similarity	NPD7930	Approved
0.6368	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6355	Discontinued
0.6364	Remote Similarity	NPD7411	Suspended
0.6356	Remote Similarity	NPD6723	Discontinued
0.6354	Remote Similarity	NPD4110	Phase 3
0.6354	Remote Similarity	NPD3750	Approved
0.6354	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5402	Approved
0.6348	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3705	Approved
0.6318	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6100	Approved
0.6316	Remote Similarity	NPD6099	Approved
0.6316	Remote Similarity	NPD2438	Suspended
0.631	Remote Similarity	NPD4060	Phase 1
0.6306	Remote Similarity	NPD7999	Approved
0.6296	Remote Similarity	NPD6534	Approved
0.6296	Remote Similarity	NPD6535	Approved
0.6293	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6798	Discontinued
0.6286	Remote Similarity	NPD7549	Discontinued
0.6284	Remote Similarity	NPD4420	Approved
0.6283	Remote Similarity	NPD5763	Approved
0.6283	Remote Similarity	NPD3540	Phase 1
0.6283	Remote Similarity	NPD5762	Approved
0.6277	Remote Similarity	NPD230	Phase 1
0.6277	Remote Similarity	NPD4340	Discontinued
0.6276	Remote Similarity	NPD6273	Approved
0.6273	Remote Similarity	NPD2493	Approved
0.6273	Remote Similarity	NPD2494	Approved
0.6269	Remote Similarity	NPD4628	Phase 3
0.6261	Remote Similarity	NPD4583	Approved
0.6261	Remote Similarity	NPD4582	Approved
0.6257	Remote Similarity	NPD4404	Approved
0.6257	Remote Similarity	NPD6233	Phase 2
0.6257	Remote Similarity	NPD6663	Approved
0.6256	Remote Similarity	NPD1511	Approved
0.625	Remote Similarity	NPD970	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6801	Discontinued
0.6239	Remote Similarity	NPD7223	Discontinued
0.6239	Remote Similarity	NPD7224	Discontinued
0.6238	Remote Similarity	NPD6765	Approved
0.6238	Remote Similarity	NPD6764	Approved
0.623	Remote Similarity	NPD3539	Phase 1
0.6226	Remote Similarity	NPD8054	Approved
0.6226	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8053	Approved
0.6224	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD5929	Approved
0.6216	Remote Similarity	NPD4004	Approved
0.6216	Remote Similarity	NPD4002	Approved
0.6215	Remote Similarity	NPD7906	Approved
0.6207	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3764	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