NPASS Compound

Structure

NPC481841 OpenBabel06302215142D 28 30 0 0 1 0 0 0 0 0999 V2000 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 3 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 -0.8660 -1.5000 0.0000 N 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 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 -3.4641 0.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 3 6 1 0 0 0 0 4 5 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 11 12 2 3 0 0 0 12 25 1 0 0 0 0 12 13 1 0 0 0 0 13 18 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	399.21
Volume:	419.231
LogP:	5.334
LogD:	4.05
LogS:	-5.842
# Rotatable Bonds:	8
TPSA:	40.62
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	3.231
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	7.572222330054501e-06
Pgp-inhibitor:	0.998
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.753
30% Bioavailability (F30%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.794
Plasma Protein Binding (PPB):	94.70718383789062%
Volume Distribution (VD):	3.299
Pgp-substrate:	5.464272975921631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.887
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.458
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	4.051
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.837
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.905
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC481841

Natural Product ID:	NPC481841
*Common Name:**	GPKJTRJOBQGKQK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPKJTRJOBQGKQK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
SMILES:	CCN(CC)CCCC(C)N=c1c2ccc(cc2[nH]c2ccc(cc12)OC)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines

*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
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520233]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932145]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568764]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	pericarp	n.a.	n.a.	PMID[16038565]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18166016]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20232858]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	Database[Article]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	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	35
ED50	3
IC50	53
Kd	2
Ki	3
LD50	5
Others	44

Activity Type	# Activity
Cell Line	39
CELL-LINE	3
Individual Protein	30
NON-MOLECULAR	17
Organism	33
Others	16
Protein Complex	1
Protein Family	4
SINGLE PROTEIN	1
SMALL MOLECULE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	55000.0	nM	PMID[8289202]
NPT4316	Individual Protein	Phospholipase A2 group 1B	Rattus norvegicus	IC50	=	100000.0	nM	DOI[10.1016/S0960-894X(01)81260-9]
NPT183	Individual Protein	Arachidonate 5-lipoxygenase	Rattus norvegicus	IC50	=	130000.0	nM	DOI[10.1016/S0960-894X(01)81260-9]
NPT1557	Individual Protein	Glutathione reductase	Homo sapiens	IC50	>	1000000.0	nM	PMID[11551771]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	Inhibition	=	48.9	%	PMID[7629818]
NPT2852	Individual Protein	Prion protein	Homo sapiens	EC50	=	300.0	nM	PMID[12904059]
NPT4592	Cell Line	CHO-AA8	Cricetulus griseus	IC50	=	1700.0	nM	PMID[2319563]
NPT2945	Individual Protein	Phospholipase A2 group 1B	Sus scrofa	IC50	=	100000.0	nM	DOI[10.1016/S0960-894X(01)81022-2]
NPT183	Individual Protein	Arachidonate 5-lipoxygenase	Rattus norvegicus	IC50	=	130000.0	nM	DOI[10.1016/S0960-894X(01)81022-2]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	14.9	%	PMID[2066998]
NPT4062	Individual Protein	Phospholipase A2 group IIA	Rattus norvegicus	IC50	=	320000000.0	nM	PMID[8978846]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	76000000.0	nM	PMID[8978846]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	Inhibition	=	82.0	%	PMID[15177454]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	Inhibition	=	50.0	%	PMID[15177454]
NPT3035	Cell Line	ScN2a	Mus musculus	EC50	=	500.0	nM	PMID[16860557]
NPT3035	Cell Line	ScN2a	Mus musculus	LD50	=	9.6	uM	PMID[16860557]
NPT71	Cell Line	HEK293	Homo sapiens	LD50	=	7.6	uM	PMID[16860557]
NPT65	Cell Line	HepG2	Homo sapiens	LD50	=	7.9	uM	PMID[16860557]
NPT3035	Cell Line	ScN2a	Mus musculus	EC50	=	300.0	nM	PMID[17064077]
NPT3035	Cell Line	ScN2a	Mus musculus	Activity	=	500.0	nM	PMID[17064077]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	57.0	%	PMID[17064070]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	25000000.0	RLU/mg	PMID[17064070]
NPT3035	Cell Line	ScN2a	Mus musculus	EC50	=	800.0	nM	PMID[17201410]
NPT3035	Cell Line	ScN2a	Mus musculus	LD50	=	7.8	uM	PMID[17201410]
NPT2249	Individual Protein	Histidine-rich protein	Plasmodium falciparum	IC50	=	292000.0	nM	PMID[17088494]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Inhibition	=	72.0	%	PMID[17911242]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	18.4	%	PMID[11520233]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	8.7	%	PMID[11520233]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	IC50	=	2160000.0	nM	PMID[8984162]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	85.5	%	PMID[8984162]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	IC50	=	2150000.0	nM	PMID[9392883]
NPT3035	Cell Line	ScN2a	Mus musculus	Activity	=	2.5	uM	PMID[18556207]
NPT1229	Cell Line	Huh-7	Homo sapiens	CC50	=	19610.0	nM	PMID[18579783]
NPT984	Cell Line	Hepatocyte		TC50	>	1.16	10'4nM	PMID[18212104]
NPT2742	Individual Protein	Aldehyde oxidase	Homo sapiens	IC50	=	3300.0	nM	PMID[20853847]
NPT2933	Individual Protein	Aldehyde oxidase	Oryctolagus cuniculus	IC50	=	10000.0	nM	PMID[20853847]
NPT4069	Individual Protein	Riboflavin-binding protein	Gallus gallus	Ki	=	6700.0	nM	PMID[21686082]
NPT4069	Individual Protein	Riboflavin-binding protein	Gallus gallus	Kd	=	264.0	nM	PMID[21686082]
NPT616	Cell Line	MDCK	Canis lupus familiaris	Ratio	=	1.2	n.a.	PMID[21531054]
NPT616	Cell Line	MDCK	Canis lupus familiaris	Ratio	=	5.1	n.a.	PMID[21531054]
NPT2689	Individual Protein	Indoleamine 2,3-dioxygenase 2	Mus musculus	Inhibition	>=	55.0	%	PMID[23122865]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	=	9780.0	nM	PMID[24354316]
NPT804	Cell Line	HT-22	Mus musculus	EC50	=	9090.0	nM	PMID[24602904]
NPT2719	Individual Protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	IC50	=	5200.0	nM	PMID[22761000]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	10440.0	nM	PMID[27992217]
NPT65	Cell Line	HepG2	Homo sapiens	EC90	=	18.23	uM	PMID[27992217]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	10440.0	nM	PMID[28740614]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	3960.0	nM	PMID[29232580]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3250.0	nM	PMID[29232580]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4190.0	nM	PMID[29232580]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	3960.0	nM	PMID[28586716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3250.0	nM	PMID[28586716]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4190.0	nM	PMID[28586716]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	14710.0	nM	DOI[10.1101/2020.03.20.999730]
NPT1045	Cell Line	U2OS	Homo sapiens	LD50	=	2.5	uM	PMID[29211480]
NPT1045	Cell Line	U2OS	Homo sapiens	EC	=	0.2	uM	PMID[29211480]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7500.0	nM	PMID[30684866]
NPT2846	Cell Line	BHK-21	Cricetulus griseus	CC50	=	18590.0	nM	PMID[31549836]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	7653700.0	nM	PMID[30655955]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	5000.0	nM	PMID[30583248]
NPT4473	Cell Line	WIL2-NS	Homo sapiens	CC50	=	4800.0	nM	PMID[33479683]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	=	7600.0	nM	PMID[33479683]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	31200.0	nM	PMID[12361395]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	28800.0	nM	PMID[12361395]
NPT1774	Protein Family	Sodium channel alpha subunits; brain (Types I, II, III)	Homo sapiens	IC50	=	3300.0	nM	PMID[2579237]
NPT1774	Protein Family	Sodium channel alpha subunits; brain (Types I, II, III)	Homo sapiens	Inhibition	=	73.3	%	PMID[2579237]
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	Ki	=	19000.0	nM	PMID[10639286]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED30	=	5.8	uM kg-1	DOI[10.1016/S0960-894X(01)81260-9]
NPT4866	Protein Family	Prostaglandin G/H synthase (cyclooxygenase)	Ovis aries	IC50	=	130000.0	nM	DOI[10.1016/S0960-894X(01)81260-9]
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	IC50	=	133000.0	nM	PMID[11551771]
NPT2	Others	Unspecified		Ratio	=	11.5	n.a.	PMID[2319563]
NPT32	Organism	Mus musculus	Mus musculus	ED50	>	100.0	ug ear-1	DOI[10.1016/S0960-894X(01)81022-2]
NPT4747	Protein Family	Cyclooxygenase	Bos taurus	IC50	=	32600.0	nM	DOI[10.1016/S0960-894X(01)81022-2]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	92.0	%	PMID[7035667]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	80.0	%	PMID[7035667]
NPT2	Others	Unspecified		Inhibition	=	93.0	%	PMID[15177454]
NPT2	Others	Unspecified		Inhibition	=	80.0	%	PMID[15177454]
NPT2	Others	Unspecified		Inhibition	=	75.0	%	PMID[15177454]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	5.0	nM	PMID[15686903]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	8.0	nM	PMID[15686903]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	32.0	nM	PMID[15686903]
NPT2	Others	Unspecified		IC50	=	73000.0	nM	PMID[15225721]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	11.0	nM	PMID[17371810]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	33.0	nM	PMID[17371810]
NPT2	Others	Unspecified		IC50	=	13700.0	nM	PMID[15568764]
NPT2	Others	Unspecified		IC50	=	23300.0	nM	PMID[15568764]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	230.0	nM	PMID[18556207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.8	uM	PMID[18556207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	590.0	nM	PMID[18556207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	460.0	nM	PMID[18556207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.0	uM	PMID[18556207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1880.0	nM	PMID[18556207]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	43.0	nM	PMID[18395298]
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	Ki	=	19000.0	nM	PMID[19414258]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	420.0	nM	PMID[19842664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	300.0	nM	PMID[19842664]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	8.13	nM	PMID[18579783]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	14.22	nM	PMID[18579783]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	41000.0	nM	PMID[20185316]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	936.0	nM	PMID[17417631]
NPT1188	Organism	Plasmodium yoelii yoelii	Plasmodium yoelii yoelii	IC50	=	30000.0	nM	PMID[18212104]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[21277202]
NPT914	Individual Protein	Acetylcholinesterase	Bos taurus	Inhibition	=	49.0	%	PMID[21459491]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	4500.0	nM	PMID[21459491]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	IC50	=	165.7	nM	PMID[22096101]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	EC50	=	14400.0	nM	PMID[8862725]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	230.0	nM	PMID[21531054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.8	uM	PMID[21531054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	590.0	nM	PMID[21531054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1880.0	nM	PMID[21531054]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	43.0	nM	DOI[10.1007/s00044-007-9025-8]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	13.0	nM	DOI[10.1007/s00044-007-9025-8]
NPT20576	SMALL MOLECULE	Heme	n.a.	IC50	=	41000.0	nM	DOI[10.1007/s00044-007-9025-8]
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[24900645]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	400.0	nM	PMID[24900645]
NPT27	Others	Unspecified		CC50	=	3920.0	nM	PMID[24354316]
NPT5839	Protein Complex	Bacterial DNA-directed RNA polymerase	Bacteria	IC50	=	20000.0	nM	PMID[184284]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2120.0	nM	PMID[27788467]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	11900.0	nM	PMID[27788467]
NPT2	Others	Unspecified		EC50	=	4230.0	nM	PMID[27992217]
NPT2	Others	Unspecified		EC90	=	9.94	uM	PMID[27992217]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	101100.0	nM	PMID[22961681]
NPT2	Others	Unspecified		EC50	=	4230.0	nM	PMID[28740614]
NPT24746	CELL-LINE	184B5	Homo sapiens	IC50	=	4960.0	nM	PMID[29232580]
NPT24746	CELL-LINE	184B5	Homo sapiens	IC50	=	4960.0	nM	PMID[28586716]
NPT2	Others	Unspecified		CC50	=	2.34	nM	PMID[28835807]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	50000.0	nM	DOI[10.1101/2020.03.20.999730]
NPT22368	ORGANISM	Zika virus	Zika virus	EC50	=	2270.0	nM	PMID[31549836]
NPT2	Others	Unspecified		EC50	=	2974100.0	nM	PMID[30655955]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	29.0	nM	PMID[30852885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18.0	nM	PMID[30852885]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23.0	nM	PMID[30852885]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	5300.0	nM	PMID[31128447]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-4.1	%	DOI[10.6019/CHEMBL4495564]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.24	%	DOI[10.6019/CHEMBL4495565]
NPT24749	ORGANISM	Ebolavirus	Ebolavirus	IC50	=	1050.0	nM	PMID[32832035]
NPT2	Others	Unspecified		Kd	=	7550.0	nM	PMID[32832035]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	50.0	%	PMID[33486051]
NPT2	Others	Unspecified		IC50	=	16990.0	nM	PMID[32738977]
NPT28129	CELL-LINE	UV4	Cricetulus griseus	IC50	=	140.0	nM	PMID[2319563]

☑ 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 NPC481841 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	605
0.1-0.2	5734
0.2-0.3	11700
0.3-0.4	11444
0.4-0.5	8306
0.5-0.6	3339
0.6-0.7	1370
0.7-0.8	190
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID

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 NPC481841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	744
0.2-0.3	882
0.3-0.4	1156
0.4-0.5	2623
0.5-0.6	2483
0.6-0.7	834
0.7-0.8	124
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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