NPASS Compound

Structure

CID160666 OpenBabel06191715532D 34 37 0 0 1 0 0 0 0 0999 V2000 4.9247 2.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5234 3.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0388 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0388 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0388 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0388 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0388 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1613 0.2607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 2.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3479 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3424 1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5388 2.2321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7491 1.0697 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1668 0.3652 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 2.8968 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9302 2.7923 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5388 0.5000 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 28 1 0 0 0 0 2 28 1 0 0 0 0 3 33 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 30 1 0 0 0 0 10 24 2 0 0 0 0 10 25 1 0 0 0 0 11 26 2 0 0 0 0 11 29 1 0 0 0 0 13 33 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 6 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 34 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 1 0 0 0 19 24 1 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 27 2 3 0 0 0 21 32 1 0 0 0 0 22 29 1 6 0 0 0 22 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	471.22
Volume:	454.679
LogP:	0.551
LogD:	0.736
LogS:	-1.523
# Rotatable Bonds:	9
TPSA:	160.88
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	3.939
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.754
MDCK Permeability:	5.135556421009824e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.861
20% Bioavailability (F20%):	0.587
30% Bioavailability (F30%):	0.503

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.491
Plasma Protein Binding (PPB):	50.3372802734375%
Volume Distribution (VD):	1.43
Pgp-substrate:	52.67213439941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.482
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	9.529
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.217
Skin Sensitization:	0.138
Carcinogencity:	0.61
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.38

Download Data

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

Natural Product: NPC160666

Natural Product ID:	NPC160666
*Common Name:**	Puromycin
IUPAC Name:	(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
Synonyms:	3123L; CL-13900; GNF-Pf-2016; P-638; Puromycin; TCMDC-123493
Standard InCHIKey:	RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Standard InCHI:	InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1
SMILES:	CN(C)c1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)N=C([C@H](Cc1ccc(cc1)OC)N)O)O
Synthetic Gene Cluster:	BGC0000878;
ChEMBL Identifier:	CHEMBL469912
PubChem CID:	439530
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0000479] Purine nucleosides [CHEMONTID:0002178] Purine 3'-deoxyribonucleosides

*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
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651537]
NPO40074	Cleistochlamys kirkii	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28001067]
NPO40120	Eremophila microtheca	Species	Scrophulariaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[28774427]
NPO40135	Flindersia pimenteliana	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29236492]
NPO40215	Streptomyces sp. CB01388	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29469575]
NPO40120	Eremophila microtheca	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29533611]
NPO40089	Corymbia torelliana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29969262]
NPO40229	Streptomyces sp. PU-14G	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30418763]
NPO40003	Acronychia pubescens	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30865443]
NPO41040	Sphaerocoryne gracilis ssp. gracilis	Strain	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32067457]
NPO40732	Amathia lamourouxi	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[33105995]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	8
ED50	1
IC50	75
Kd	4
Ki	1
MIC	8
Others	84
Potency	6

Activity Type	# Activity
Cell Line	52
CELL-LINE	1
Individual Protein	19
NON-MOLECULAR	7
Organism	63
Others	38
PROTEIN NUCLEIC-ACID COMPLEX	168
SINGLE PROTEIN	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.5	ug.mL-1	PMID[568796]
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	64.0	%	PMID[568798]
NPT4849	Cell Line	P815	Mus musculus	Inhibition	=	98.0	%	PMID[568798]
NPT4850	Cell Line	Osteoclast-like		Inhibition	=	61.0	%	PMID[568798]
NPT137	Cell Line	L1210	Mus musculus	Log CR	=	1.82	n.a.	PMID[568799]
NPT1161	Cell Line	CHO	Cricetulus griseus	Log CR	=	2.02	n.a.	PMID[568799]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	378000.0	nM	PMID[568805]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	230.0	nM	PMID[568805]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	83930.0	nM	PMID[568805]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	364000.0	nM	PMID[568805]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	220.0	nM	PMID[568805]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	26830.0	nM	PMID[568805]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	122000.0	nM	PMID[568805]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	210.0	nM	PMID[568806]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	99.0	%	PMID[568808]
NPT1229	Cell Line	Huh-7	Homo sapiens	CC50	=	6630.0	nM	PMID[568809]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	420.0	nM	PMID[568810]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	22387.2	nM	PMID[568813]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	17782.8	nM	PMID[568813]
NPT71	Cell Line	HEK293	Homo sapiens	GI	=	100.0	%	PMID[568822]
NPT2257	Cell Line	MCF-10A	Homo sapiens	GI	=	100.0	%	PMID[568822]
NPT845	Cell Line	BT-474	Homo sapiens	GI	=	100.0	%	PMID[568822]
NPT461	Cell Line	PANC-1	Homo sapiens	GI	=	100.0	%	PMID[568822]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI	=	100.0	%	PMID[568822]
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	10000.0	nM	PMID[568823]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-7.92	%	PMID[568824]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1.8	nM	PMID[568813]
NPT4852	Individual Protein	Puromycin-sensitive aminopeptidase	Homo sapiens	IC50	=	2450.0	nM	PMID[568833]
NPT1553	Individual Protein	Aminopeptidase N	Sus scrofa	IC50	>	100000.0	nM	PMID[568833]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	361.0	nM	PMID[568834]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	350.5	nM	PMID[568835]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	600.0	nM	PMID[568836]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	0.35	nM	PMID[568837]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	CC50	=	480.0	nM	PMID[568839]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	CC50	=	200.0	nM	PMID[568839]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	360.0	nM	PMID[568840]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	399.0	nM	PMID[568841]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	460.0	nM	PMID[568842]
NPT4852	Individual Protein	Puromycin-sensitive aminopeptidase	Homo sapiens	IC50	=	9700.0	nM	PMID[568843]
NPT2553	Individual Protein	Aminopeptidase N	Homo sapiens	Inhibition	=	15.7	%	PMID[568843]
NPT2553	Individual Protein	Aminopeptidase N	Homo sapiens	IC50	=	41000.0	nM	PMID[568843]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	99.0	%	PMID[568843]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	2800.0	nM	PMID[568843]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	55.0	nM	PMID[568843]
NPT112	Cell Line	MOLT-4	Homo sapiens	EC50	=	170.0	nM	PMID[568843]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	450.0	nM	PMID[568844]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	400.0	nM	PMID[568845]
NPT65	Cell Line	HepG2	Homo sapiens	pCC50	=	6.3	n.a.	PMID[568846]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	6100.0	nM	PMID[568847]
NPT2615	Cell Line	HEK-293T	Homo sapiens	CC50	=	420.0	nM	PMID[568847]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	=	830.0	nM	PMID[568847]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	460.0	nM	PMID[568848]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	300.0	nM	PMID[568849]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	300.0	nM	PMID[568849]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	=	500.1	nM	PMID[568850]
NPT71	Cell Line	HEK293	Homo sapiens	GI	=	104.9	%	PMID[568850]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	=	18000000.0	nM	PMID[568852]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	694.0	nM	PMID[568854]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	360.0	nM	PMID[568855]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	=	230.0	nM	PMID[568857]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	810.0	nM	PMID[568858]
NPT2	Others	Unspecified		Km	=	134000.0	nM	PMID[568797]
NPT2	Others	Unspecified		Vmax	=	0.99	pM min-1	PMID[568797]
NPT2	Others	Unspecified		Substrate efficiency	=	100.0	%	PMID[568797]
NPT2	Others	Unspecified		Log CR	=	1.92	n.a.	PMID[568799]
NPT35	Others	n.a.		LogD	=	0.86	n.a.	PMID[568799]
NPT19	Organism	Escherichia coli	Escherichia coli	Km	=	186000.0	nM	PMID[568800]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Km	=	255000.0	nM	PMID[568800]
NPT2	Others	Unspecified		Vmax	=	1890.0	c.p.m.	PMID[568800]
NPT2	Others	Unspecified		Vmax	=	14214.0	c.p.m.	PMID[568800]
NPT2	Others	Unspecified		Efficiency	=	100.0	%	PMID[568800]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.3	ug ml-1	PMID[568800]
NPT2	Others	Unspecified		Ratio	=	10161.0	n.a.	PMID[568800]
NPT2	Others	Unspecified		Ratio	=	55741.0	n.a.	PMID[568800]
NPT25183	SINGLE PROTEIN	Dihydrofolate reductase	Mus musculus	Log 1/C	=	6.46	n.a.	PMID[568801]
NPT25183	SINGLE PROTEIN	Dihydrofolate reductase	Mus musculus	Log 1/C	=	6.41	n.a.	PMID[568801]
NPT35	Others	n.a.		LogP	=	0.03	n.a.	PMID[568801]
NPT19	Organism	Escherichia coli	Escherichia coli	Ki	=	220000.0	nM	PMID[568802]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.312	ug.mL-1	PMID[568803]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	210.0	nM	PMID[568805]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	79300.0	nM	PMID[568805]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20200.0	nM	PMID[568806]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[568807]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	0.0	%	PMID[568808]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	100.0	%	PMID[568808]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	XC50	=	174.18	nM	PMID[568808]
NPT2	Others	Unspecified		IFI	=	8.45	%	PMID[568808]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	611.0	nM	PMID[568809]
NPT2	Others	Unspecified		IFI	=	30.77	%	PMID[568809]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	328.0	nM	PMID[568809]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	37.0	nM	PMID[568810]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	25.0	%	PMID[568811]
NPT317	Uncleic Acid	Nucleic Acid		EC50	=	100.0	nM	PMID[568811]
NPT317	Uncleic Acid	Nucleic Acid		Activity	>	1.0	uM	PMID[568811]
NPT25608	PROTEIN NUCLEIC-ACID COMPLEX	Bacterial 70S ribosome	Bacteria	IC50	=	900.0	nM	PMID[568812]
NPT2	Others	Unspecified		Potency	=	707.9	nM	PMID[568813]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Papp	=	11.5	nm/s	PMID[568818]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Papp	=	35.6	nm/s	PMID[568818]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio_Papp	=	3.1	n.a.	PMID[568818]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio_ATPase activity	=	1.21	n.a.	PMID[568818]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	% maximum response	=	1.91	%	PMID[568818]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	89.0	nM	PMID[568822]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	100.0	%	PMID[568822]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-9.98	%	PMID[568824]
NPT2759	Organism	Streptomyces acidiscabies	Streptomyces acidiscabies	IZ	=	20.0	mm	PMID[568825]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	64.0	nM	PMID[568826]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	46.0	nM	PMID[568826]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	137.0	nM	PMID[568826]
NPT2	Others	Unspecified		Potency	n.a.	1258.9	nM	PMID[568813]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[568813]
NPT25608	PROTEIN NUCLEIC-ACID COMPLEX	Bacterial 70S ribosome	Bacteria	Km	=	234000.0	nM	PMID[568827]
NPT25608	PROTEIN NUCLEIC-ACID COMPLEX	Bacterial 70S ribosome	Bacteria	Vmax	=	3.99	pmol/min	PMID[568827]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	194.0	nM	PMID[568828]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	175.0	nM	PMID[568828]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	100.0	%	PMID[568829]
NPT942	Individual Protein	Glucose transporter	Homo sapiens	Inhibition	=	3.7	%	PMID[568830]
NPT943	Individual Protein	Hexose transporter 1	Plasmodium falciparum	Inhibition	=	1.9	%	PMID[568830]
NPT944	Individual Protein	Glucose transporter	Leishmania mexicana	Inhibition	=	3.16	%	PMID[568830]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	42.0	nM	PMID[568831]
NPT2	Others	Unspecified		Kd	=	11800.0	nM	PMID[568832]
NPT2	Others	Unspecified		Kd	=	5850.0	nM	PMID[568832]
NPT2	Others	Unspecified		Kd	=	12700.0	nM	PMID[568832]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[568833]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	22.7	nM	PMID[568834]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	45.2	nM	PMID[568834]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	700.0	nM	PMID[568836]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	60.0	nM	PMID[568837]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	62.0	nM	PMID[568837]
NPT27	Others	Unspecified		Ratio IC50	=	6.0	n.a.	PMID[568837]
NPT2	Others	Unspecified		Kd	=	480000.0	nM	PMID[568838]
NPT2	Others	Unspecified		Ratio IC50	=	15.9	n.a.	PMID[568840]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	45.0	nM	PMID[568840]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23.0	nM	PMID[568840]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	61.0	nM	PMID[568841]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	62.0	nM	PMID[568841]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	53.2	nM	PMID[568842]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	43.8	nM	PMID[568842]
NPT2	Others	Unspecified		Ratio IC50	=	1.16	n.a.	PMID[568842]
NPT2	Others	Unspecified		Ratio IC50	=	9.0	n.a.	PMID[568842]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	32.0	nM	PMID[568844]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	53.0	nM	PMID[568844]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	100.0	%	PMID[568844]
NPT2	Others	Unspecified		Ratio IC50	=	8.0	n.a.	PMID[568844]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	60.0	nM	PMID[568845]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	61.0	nM	PMID[568845]
NPT1022	Organism	Cryptosporidium parvum	Cryptosporidium parvum	EC50	=	600.0	nM	PMID[568847]
NPT1022	Organism	Cryptosporidium parvum	Cryptosporidium parvum	EC50	=	550.0	nM	PMID[568847]
NPT2	Others	Unspecified		Ratio IC50	=	10.5	n.a.	PMID[568848]
NPT2	Others	Unspecified		Ratio IC50	=	9.0	n.a.	PMID[568848]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	44.0	nM	PMID[568848]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	53.0	nM	PMID[568848]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	<=	120000.0	nM	PMID[568849]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	4000.0	nM	PMID[568849]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4000.0	nM	PMID[568849]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4000.0	nM	PMID[568849]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4000.0	nM	PMID[568849]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	<=	120000.0	nM	PMID[568849]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	<=	120000.0	nM	PMID[568849]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	110.8	nM	PMID[568850]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	106.6	nM	PMID[568850]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	4.5	n.a.	PMID[568850]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	50.0	nM	PMID[568851]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	50.12	nM	PMID[568851]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	410.0	nM	PMID[568853]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	70.2	nM	PMID[568854]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	74.7	nM	PMID[568854]
NPT2	Others	Unspecified		Ratio IC50	=	9.9	n.a.	PMID[568854]
NPT2	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[568854]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23.0	nM	PMID[568855]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	45.0	nM	PMID[568855]
NPT2	Others	Unspecified		Ratio IC50	=	15.9	n.a.	PMID[568855]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	51.97	nM	PMID[568856]
NPT2	Others	Unspecified		Ratio IC50	=	8.0	n.a.	PMID[568856]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	38.0	nM	PMID[568857]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	110.0	nM	PMID[568858]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	68.0	nM	PMID[568858]
NPT2	Others	Unspecified		Ratio IC50	=	353.0	n.a.	PMID[568858]
NPT2	Others	Unspecified		Ratio IC50	=	585.0	n.a.	PMID[568858]
NPT27734	CELL-LINE	SU-DHL10	Homo sapiens	CC50	=	110.0	nM	PMID[568839]

☑ 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 NPC160666 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	473
0.1-0.2	3353
0.2-0.3	13578
0.3-0.4	11707
0.4-0.5	9073
0.5-0.6	3865
0.6-0.7	597
0.7-0.8	48
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9135	High Similarity	NPC250178
0.7917	Intermediate Similarity	NPC150447
0.7895	Intermediate Similarity	NPC21461
0.7773	Intermediate Similarity	NPC115595
0.7686	Intermediate Similarity	NPC107160
0.7613	Intermediate Similarity	NPC242923
0.7563	Intermediate Similarity	NPC477796
0.7563	Intermediate Similarity	NPC477805
0.7563	Intermediate Similarity	NPC477806
0.7563	Intermediate Similarity	NPC477795
0.7479	Intermediate Similarity	NPC472067
0.7479	Intermediate Similarity	NPC472031
0.7479	Intermediate Similarity	NPC472066
0.7469	Intermediate Similarity	NPC472068
0.7456	Intermediate Similarity	NPC308906
0.7342	Intermediate Similarity	NPC158055
0.7327	Intermediate Similarity	NPC280638
0.7297	Intermediate Similarity	NPC103388
0.729	Intermediate Similarity	NPC313514
0.7222	Intermediate Similarity	NPC35761
0.7203	Intermediate Similarity	NPC237978
0.7178	Intermediate Similarity	NPC30540
0.7155	Intermediate Similarity	NPC136924
0.7137	Intermediate Similarity	NPC469589
0.7137	Intermediate Similarity	NPC46970
0.7118	Intermediate Similarity	NPC471603
0.7112	Intermediate Similarity	NPC469594
0.7106	Intermediate Similarity	NPC130570
0.7087	Intermediate Similarity	NPC469592
0.7087	Intermediate Similarity	NPC471080
0.7069	Intermediate Similarity	NPC12100
0.7056	Intermediate Similarity	NPC50511
0.7054	Intermediate Similarity	NPC223223
0.7028	Intermediate Similarity	NPC56271
0.7017	Intermediate Similarity	NPC110151
0.7008	Intermediate Similarity	NPC471614
0.6966	Remote Similarity	NPC467439
0.6949	Remote Similarity	NPC17305
0.6927	Remote Similarity	NPC239737
0.6917	Remote Similarity	NPC314954
0.6905	Remote Similarity	NPC314882
0.6895	Remote Similarity	NPC472434
0.6883	Remote Similarity	NPC171393
0.6883	Remote Similarity	NPC295452
0.6883	Remote Similarity	NPC113369
0.6856	Remote Similarity	NPC472111
0.6842	Remote Similarity	NPC99891
0.6831	Remote Similarity	NPC328924
0.6824	Remote Similarity	NPC26679
0.6815	Remote Similarity	NPC39092
0.6814	Remote Similarity	NPC18487
0.6809	Remote Similarity	NPC288349
0.6807	Remote Similarity	NPC310118
0.6805	Remote Similarity	NPC323244
0.6805	Remote Similarity	NPC187145
0.6787	Remote Similarity	NPC472289
0.6784	Remote Similarity	NPC19872
0.6769	Remote Similarity	NPC315467
0.6762	Remote Similarity	NPC469554
0.6754	Remote Similarity	NPC232727
0.6744	Remote Similarity	NPC313897
0.6743	Remote Similarity	NPC478009
0.6737	Remote Similarity	NPC8022
0.6737	Remote Similarity	NPC470799
0.6726	Remote Similarity	NPC267928
0.6723	Remote Similarity	NPC193267
0.6723	Remote Similarity	NPC213530
0.6719	Remote Similarity	NPC51854
0.6704	Remote Similarity	NPC477633
0.6695	Remote Similarity	NPC185782
0.668	Remote Similarity	NPC9729
0.6667	Remote Similarity	NPC279401
0.6667	Remote Similarity	NPC478006
0.6667	Remote Similarity	NPC219963
0.6667	Remote Similarity	NPC472436
0.6667	Remote Similarity	NPC470500
0.6667	Remote Similarity	NPC144114
0.6667	Remote Similarity	NPC79293
0.6667	Remote Similarity	NPC161887
0.6667	Remote Similarity	NPC226202
0.6653	Remote Similarity	NPC184680
0.6653	Remote Similarity	NPC266931
0.6638	Remote Similarity	NPC176538
0.6634	Remote Similarity	NPC150853
0.6627	Remote Similarity	NPC470785
0.6623	Remote Similarity	NPC475774
0.6623	Remote Similarity	NPC223427
0.6617	Remote Similarity	NPC478011
0.6616	Remote Similarity	NPC478010
0.6615	Remote Similarity	NPC472435
0.6613	Remote Similarity	NPC295228
0.6605	Remote Similarity	NPC222174
0.6598	Remote Similarity	NPC60621
0.6596	Remote Similarity	NPC123976
0.6596	Remote Similarity	NPC5145
0.6596	Remote Similarity	NPC167860
0.6593	Remote Similarity	NPC84853
0.6592	Remote Similarity	NPC314176
0.6587	Remote Similarity	NPC316756
0.6587	Remote Similarity	NPC469975
0.6584	Remote Similarity	NPC125597
0.6581	Remote Similarity	NPC287208
0.6581	Remote Similarity	NPC475910
0.6571	Remote Similarity	NPC476997
0.6569	Remote Similarity	NPC238945
0.6569	Remote Similarity	NPC309832
0.6565	Remote Similarity	NPC121772
0.6564	Remote Similarity	NPC63109
0.6562	Remote Similarity	NPC230805
0.656	Remote Similarity	NPC470784
0.6559	Remote Similarity	NPC101543
0.6556	Remote Similarity	NPC132642
0.6553	Remote Similarity	NPC174758
0.6552	Remote Similarity	NPC245816
0.6552	Remote Similarity	NPC476138
0.6545	Remote Similarity	NPC476998
0.6545	Remote Similarity	NPC476996
0.654	Remote Similarity	NPC314056
0.654	Remote Similarity	NPC203168
0.6537	Remote Similarity	NPC54537
0.6532	Remote Similarity	NPC180504
0.6531	Remote Similarity	NPC244536
0.653	Remote Similarity	NPC477634
0.6525	Remote Similarity	NPC219664
0.6522	Remote Similarity	NPC187558
0.652	Remote Similarity	NPC28945
0.652	Remote Similarity	NPC189068
0.6516	Remote Similarity	NPC477891
0.6516	Remote Similarity	NPC98371
0.6516	Remote Similarity	NPC266551
0.6516	Remote Similarity	NPC313884
0.6512	Remote Similarity	NPC125659
0.6512	Remote Similarity	NPC168702
0.6507	Remote Similarity	NPC208751
0.6504	Remote Similarity	NPC315822
0.6504	Remote Similarity	NPC476994
0.6502	Remote Similarity	NPC62510
0.6494	Remote Similarity	NPC474183
0.6494	Remote Similarity	NPC315957
0.6493	Remote Similarity	NPC478012
0.6488	Remote Similarity	NPC219313
0.6483	Remote Similarity	NPC174672
0.6475	Remote Similarity	NPC74619
0.6471	Remote Similarity	NPC202605
0.6471	Remote Similarity	NPC21448
0.6471	Remote Similarity	NPC112206
0.6471	Remote Similarity	NPC156461
0.6471	Remote Similarity	NPC107374
0.6466	Remote Similarity	NPC141053
0.6466	Remote Similarity	NPC478013
0.6466	Remote Similarity	NPC220852
0.6463	Remote Similarity	NPC251090
0.6461	Remote Similarity	NPC473317
0.6458	Remote Similarity	NPC170114
0.6453	Remote Similarity	NPC264166
0.6453	Remote Similarity	NPC285558
0.6453	Remote Similarity	NPC475070
0.6453	Remote Similarity	NPC118832
0.6453	Remote Similarity	NPC165349
0.6453	Remote Similarity	NPC329708
0.6453	Remote Similarity	NPC47059
0.6453	Remote Similarity	NPC274291
0.6452	Remote Similarity	NPC164664
0.6447	Remote Similarity	NPC307963
0.6445	Remote Similarity	NPC471891
0.6443	Remote Similarity	NPC81175
0.6441	Remote Similarity	NPC476465
0.6441	Remote Similarity	NPC82548
0.6439	Remote Similarity	NPC164665
0.6438	Remote Similarity	NPC5802
0.6438	Remote Similarity	NPC317054
0.6437	Remote Similarity	NPC258048
0.6434	Remote Similarity	NPC280272
0.6431	Remote Similarity	NPC284141
0.6429	Remote Similarity	NPC20249
0.6426	Remote Similarity	NPC89987
0.6426	Remote Similarity	NPC472286
0.6426	Remote Similarity	NPC472287
0.6423	Remote Similarity	NPC2497
0.6423	Remote Similarity	NPC103687
0.6423	Remote Similarity	NPC132631
0.6422	Remote Similarity	NPC476688
0.6422	Remote Similarity	NPC105758
0.6422	Remote Similarity	NPC476686
0.6417	Remote Similarity	NPC470549
0.641	Remote Similarity	NPC157821
0.6408	Remote Similarity	NPC269827
0.6406	Remote Similarity	NPC278874
0.6405	Remote Similarity	NPC303658
0.6404	Remote Similarity	NPC324149
0.6402	Remote Similarity	NPC316981
0.64	Remote Similarity	NPC323752
0.6397	Remote Similarity	NPC473185
0.6397	Remote Similarity	NPC476492
0.6396	Remote Similarity	NPC473585
0.6395	Remote Similarity	NPC31930
0.6395	Remote Similarity	NPC26543
0.6395	Remote Similarity	NPC276373
0.6393	Remote Similarity	NPC208060
0.639	Remote Similarity	NPC274982

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 NPC160666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	651
0.2-0.3	857
0.3-0.4	1640
0.4-0.5	2691
0.5-0.6	2199
0.6-0.7	765
0.7-0.8	118
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD5703	Discontinued
0.8421	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3590	Clinical (unspecified phase)
0.8381	Intermediate Similarity	NPD2876	Phase 3
0.8381	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD2824	Phase 2
0.8243	Intermediate Similarity	NPD6023	Discontinued
0.8233	Intermediate Similarity	NPD2903	Clinical (unspecified phase)
0.8233	Intermediate Similarity	NPD2902	Phase 2
0.8222	Intermediate Similarity	NPD4080	Discontinued
0.8091	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5080	Phase 2
0.7873	Intermediate Similarity	NPD5079	Phase 2
0.7838	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7837	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD1273	Discontinued
0.7718	Intermediate Similarity	NPD8442	Discontinued
0.7713	Intermediate Similarity	NPD6643	Discontinued
0.7712	Intermediate Similarity	NPD6573	Phase 3
0.7712	Intermediate Similarity	NPD6572	Phase 2
0.7686	Intermediate Similarity	NPD6326	Phase 2
0.7686	Intermediate Similarity	NPD6327	Phase 1
0.7672	Intermediate Similarity	NPD4306	Phase 1
0.7665	Intermediate Similarity	NPD6036	Suspended
0.7647	Intermediate Similarity	NPD7486	Phase 1
0.7639	Intermediate Similarity	NPD3602	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7706	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4713	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4714	Approved
0.7534	Intermediate Similarity	NPD34	Approved
0.7534	Intermediate Similarity	NPD4715	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD534	Phase 2
0.7533	Intermediate Similarity	NPD537	Phase 2
0.7532	Intermediate Similarity	NPD4654	Phase 1
0.75	Intermediate Similarity	NPD5949	Phase 3
0.75	Intermediate Similarity	NPD1624	Phase 2
0.75	Intermediate Similarity	NPD6856	Discontinued
0.7489	Intermediate Similarity	NPD7051	Phase 3
0.7489	Intermediate Similarity	NPD3838	Phase 3
0.7489	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD6760	Discontinued
0.7479	Intermediate Similarity	NPD6243	Phase 3
0.7479	Intermediate Similarity	NPD6244	Phase 3
0.747	Intermediate Similarity	NPD3343	Phase 3
0.747	Intermediate Similarity	NPD7273	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5567	Approved
0.7422	Intermediate Similarity	NPD6202	Discontinued
0.7417	Intermediate Similarity	NPD7067	Approved
0.7417	Intermediate Similarity	NPD7068	Approved
0.7412	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4495	Phase 1
0.7409	Intermediate Similarity	NPD5486	Discontinued
0.7399	Intermediate Similarity	NPD4612	Discontinued
0.7397	Intermediate Similarity	NPD8250	Phase 2
0.7395	Intermediate Similarity	NPD6605	Phase 3
0.7389	Intermediate Similarity	NPD5868	Approved
0.7379	Intermediate Similarity	NPD5116	Phase 1
0.7375	Intermediate Similarity	NPD6473	Phase 1
0.7371	Intermediate Similarity	NPD3043	Approved
0.7371	Intermediate Similarity	NPD3042	Approved
0.7366	Intermediate Similarity	NPD5644	Phase 1
0.7366	Intermediate Similarity	NPD6351	Discovery
0.7357	Intermediate Similarity	NPD6528	Phase 1
0.7344	Intermediate Similarity	NPD5802	Phase 2
0.7342	Intermediate Similarity	NPD6840	Approved
0.7336	Intermediate Similarity	NPD4916	Discontinued
0.7328	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6772	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7758	Approved
0.7324	Intermediate Similarity	NPD7757	Approved
0.7321	Intermediate Similarity	NPD5529	Phase 1
0.7321	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4599	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5107	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5458	Discontinued
0.7306	Intermediate Similarity	NPD5875	Approved
0.7306	Intermediate Similarity	NPD5878	Approved
0.7301	Intermediate Similarity	NPD2540	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6186	Approved
0.7292	Intermediate Similarity	NPD5905	Phase 1
0.729	Intermediate Similarity	NPD7138	Phase 2
0.7285	Intermediate Similarity	NPD4459	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4458	Phase 2
0.7284	Intermediate Similarity	NPD1954	Phase 1
0.7277	Intermediate Similarity	NPD2453	Phase 2
0.7277	Intermediate Similarity	NPD2451	Phase 2
0.7277	Intermediate Similarity	NPD2450	Phase 2
0.7277	Intermediate Similarity	NPD2452	Phase 2
0.7276	Intermediate Similarity	NPD6743	Phase 2
0.7276	Intermediate Similarity	NPD6742	Phase 2
0.7273	Intermediate Similarity	NPD7620	Phase 2
0.7273	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6750	Phase 2
0.7243	Intermediate Similarity	NPD5044	Phase 2
0.7241	Intermediate Similarity	NPD6589	Phase 1
0.7231	Intermediate Similarity	NPD5833	Phase 1
0.7227	Intermediate Similarity	NPD5018	Phase 3
0.7222	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3938	Phase 1
0.722	Intermediate Similarity	NPD2929	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6992	Phase 2
0.7208	Intermediate Similarity	NPD5920	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6482	Phase 1
0.7195	Intermediate Similarity	NPD5665	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1287	Phase 2
0.7185	Intermediate Similarity	NPD5627	Approved
0.7185	Intermediate Similarity	NPD7705	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4673	Phase 2
0.7176	Intermediate Similarity	NPD3254	Phase 1
0.7176	Intermediate Similarity	NPD3255	Phase 1
0.7156	Intermediate Similarity	NPD7323	Phase 2
0.7155	Intermediate Similarity	NPD6500	Approved
0.7155	Intermediate Similarity	NPD6501	Approved
0.7149	Intermediate Similarity	NPD4858	Phase 2
0.7149	Intermediate Similarity	NPD7117	Phase 2
0.7143	Intermediate Similarity	NPD4996	Approved
0.7143	Intermediate Similarity	NPD4995	Approved
0.7132	Intermediate Similarity	NPD6175	Phase 3
0.7126	Intermediate Similarity	NPD6216	Approved
0.7124	Intermediate Similarity	NPD796	Phase 2
0.7121	Intermediate Similarity	NPD5509	Phase 1
0.7108	Intermediate Similarity	NPD5539	Phase 2
0.7107	Intermediate Similarity	NPD3849	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2414	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD6197	Approved
0.7106	Intermediate Similarity	NPD5045	Phase 2
0.7105	Intermediate Similarity	NPD4048	Approved
0.7102	Intermediate Similarity	NPD6774	Approved
0.7101	Intermediate Similarity	NPD6708	Discontinued
0.7101	Intermediate Similarity	NPD4925	Approved
0.7098	Intermediate Similarity	NPD4442	Phase 2
0.7095	Intermediate Similarity	NPD1259	Discontinued
0.7087	Intermediate Similarity	NPD4457	Phase 2
0.7083	Intermediate Similarity	NPD7558	Phase 2
0.708	Intermediate Similarity	NPD2060	Approved
0.7077	Intermediate Similarity	NPD6754	Phase 3
0.7076	Intermediate Similarity	NPD5829	Phase 2
0.7074	Intermediate Similarity	NPD3570	Phase 2
0.7074	Intermediate Similarity	NPD949	Phase 1
0.7074	Intermediate Similarity	NPD4131	Phase 3
0.7071	Intermediate Similarity	NPD2062	Phase 2
0.7064	Intermediate Similarity	NPD2410	Phase 2
0.7059	Intermediate Similarity	NPD8421	Discontinued
0.7056	Intermediate Similarity	NPD429	Approved
0.7054	Intermediate Similarity	NPD2757	Phase 2
0.7035	Intermediate Similarity	NPD1915	Phase 1
0.7032	Intermediate Similarity	NPD1286	Suspended
0.7028	Intermediate Similarity	NPD5008	Approved
0.702	Intermediate Similarity	NPD5051	Phase 1
0.7016	Intermediate Similarity	NPD3886	Phase 1
0.7009	Intermediate Similarity	NPD2601	Approved
0.7009	Intermediate Similarity	NPD2600	Approved
0.7009	Intermediate Similarity	NPD2599	Approved
0.7008	Intermediate Similarity	NPD6537	Approved
0.7008	Intermediate Similarity	NPD6536	Approved
0.7005	Intermediate Similarity	NPD2591	Phase 2
0.7004	Intermediate Similarity	NPD5118	Phase 2
0.7	Intermediate Similarity	NPD5139	Phase 1
0.6984	Remote Similarity	NPD8049	Phase 2
0.698	Remote Similarity	NPD6848	Phase 1
0.6979	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5876	Phase 3
0.6976	Remote Similarity	NPD5877	Phase 3
0.6976	Remote Similarity	NPD6450	Phase 2
0.6974	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1231	Phase 3
0.6951	Remote Similarity	NPD5874	Phase 3
0.6951	Remote Similarity	NPD5873	Phase 3
0.6949	Remote Similarity	NPD4187	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6381	Phase 2
0.6948	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD978	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1258	Discontinued
0.6927	Remote Similarity	NPD2646	Discontinued
0.6923	Remote Similarity	NPD2530	Phase 2
0.6917	Remote Similarity	NPD1571	Phase 2
0.691	Remote Similarity	NPD4358	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7897	Phase 3
0.6903	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.69	Remote Similarity	NPD2886	Approved
0.69	Remote Similarity	NPD2885	Approved
0.69	Remote Similarity	NPD1392	Approved
0.6894	Remote Similarity	NPD6814	Phase 3
0.6891	Remote Similarity	NPD5607	Discontinued
0.6889	Remote Similarity	NPD3814	Phase 1
0.6889	Remote Similarity	NPD4548	Discontinued
0.6888	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5007	Approved
0.688	Remote Similarity	NPD5612	Discontinued
0.6878	Remote Similarity	NPD7726	Phase 1
0.6872	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2472	Approved
0.6872	Remote Similarity	NPD2471	Approved
0.6867	Remote Similarity	NPD2894	Phase 2
0.6867	Remote Similarity	NPD7506	Discontinued
0.6866	Remote Similarity	NPD8525	Approved
0.686	Remote Similarity	NPD5052	Clinical (unspecified phase)

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