NPASS Compound

Structure

NPC481920 OpenBabel06302215562D 22 23 0 0 1 0 0 0 0 0999 V2000 2.2321 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2321 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -8.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -8.5000 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 1 0 0 0 0 12 21 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 21 1 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.18
Volume:	337.79
LogP:	4.511
LogD:	3.723
LogS:	-3.902
# Rotatable Bonds:	7
TPSA:	31.39
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.813
Synthetic Accessibility Score:	3.369
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.545
MDCK Permeability:	1.0808817933138926e-05
Pgp-inhibitor:	0.752
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	71.16870880126953%
Volume Distribution (VD):	3.738
Pgp-substrate:	25.790163040161133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.623
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	5.831
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.953
Human Hepatotoxicity (H-HT):	0.766
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.488
Skin Sensitization:	0.882
Carcinogencity:	0.039
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC481920

Natural Product ID:	NPC481920
*Common Name:**	QKICWELGRMTQCR-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QKICWELGRMTQCR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;21-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2(H3,1,2,3,4)
SMILES:	CCN(CC)CCCC(C)Nc1ccnc2cc(ccc12)Cl.OP(=O)(O)O.OP(=O)(O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	64927
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000053] Aminoquinolines and derivatives [CHEMONTID:0004537] 4-aminoquinolines

*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
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000047]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO6049	Teclea trichocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141852]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309308]
NPO40107	Dobinea delavayi	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233487]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6049	Teclea trichocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25903	Swinglea glutinosa	Species	Rutaceae	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	4
ED50	3
GI50	24
IC50	115
Others	87

Activity Type	# Activity
Cell Line	32
CELL-LINE	2
Individual Protein	8
NON-MOLECULAR	7
Organism	161
Others	21
SINGLE PROTEIN	1
SMALL MOLECULE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	43.9	uM	PMID[11000047]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	100.0	uM	PMID[11575960]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	22520.0	nM	PMID[18691894]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	28580.0	nM	PMID[18691894]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	38440.0	nM	PMID[18691894]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	600.0	nM	PMID[14640524]
NPT2249	Individual Protein	Histidine-rich protein	Plasmodium falciparum	Activity	=	1.69	n.a.	PMID[18538567]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	31.83	nM	PMID[18538567]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	6.8	%	PMID[18538567]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Inhibition	=	20.4	%	PMID[18538567]
NPT2249	Individual Protein	Histidine-rich protein	Plasmodium falciparum	Ratio IC50	=	1.63	n.a.	PMID[18819813]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	28580.0	nM	PMID[19945197]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	6530.0	nM	PMID[19945197]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	6830.0	nM	PMID[19945197]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	2810.0	nM	PMID[19945197]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	GI50	=	9140.0	nM	PMID[19945197]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	22520.0	nM	PMID[19945197]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	8330.0	nM	PMID[19945197]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	12590.0	nM	PMID[19945197]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	6080.0	nM	PMID[19945197]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	18820.0	nM	PMID[19945197]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	38440.0	nM	PMID[19945197]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	7540.0	nM	PMID[19945197]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5510.0	nM	PMID[19945197]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	11780.0	nM	PMID[19945197]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	7710.0	nM	PMID[19945197]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	112500.0	nM	PMID[19957999]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	37680.0	nM	PMID[23815186]
NPT1217	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum	Inhibition	=	7.0	%	PMID[23815186]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	2.0	ug.mL-1	PMID[24139941]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	30000.0	nM	PMID[24354322]
NPT1217	Individual Protein	Botulinum neurotoxin type A	Clostridium botulinum	Inhibition	=	6.51	%	PMID[24742203]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	500000.0	nM	PMID[26774925]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	28580.0	nM	PMID[29232580]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	22520.0	nM	PMID[29232580]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	38440.0	nM	PMID[29232580]
NPT397	Cell Line	NCI-H460	Homo sapiens	TGI	=	8.67	%	PMID[33069436]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	180.0	nM	PMID[11543688]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23.0	nM	PMID[11543688]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.3	%	PMID[11543688]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	93.8	%	PMID[11543688]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	72.0	nM	PMID[8676344]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	47.0	nM	PMID[8676344]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	104.5	nM	PMID[8676344]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	160.0	ug.mL-1	PMID[11844667]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	47.0	nM	PMID[9191972]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	110.0	nM	PMID[9191972]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.16	ug.mL-1	PMID[12773043]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	50.0	nM	PMID[15456263]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	70.0	nM	PMID[15456263]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	91.0	nM	PMID[15456263]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	10.0	nM	PMID[15456263]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	246.0	nM	PMID[15801861]
NPT16971	CELL-LINE	MAC15A	Mus musculus	Ratio	=	74.2	n.a.	PMID[15801861]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	13360.0	nM	PMID[15801861]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	180.0	nM	PMID[15801861]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8.1	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	26.4	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7.5	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	33.2	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6.1	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	16.1	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5.9	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	15.8	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	35.1	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC60	=	125.0	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	33.2	nM	PMID[17220424]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	128.7	nM	PMID[17220424]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.21	ug.mL-1	PMID[3298551]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	228.0	nM	PMID[11000047]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	51.0	nM	PMID[11000047]
NPT27	Others	Unspecified		Ratio	=	190.37	n.a.	PMID[11000047]
NPT27	Others	Unspecified		Ratio	=	943.75	n.a.	PMID[11000047]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.16	ug.mL-1	PMID[11520217]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	70.0	nM	PMID[11575960]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	60.0	nM	PMID[11575960]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	450.0	nM	PMID[11575960]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	420.0	nM	PMID[11575960]
NPT2	Others	Unspecified		Ratio	>	1000.0	n.a.	PMID[11575960]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	48.0	nM	PMID[18290629]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	31.0	nM	PMID[18396855]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	300.0	nM	PMID[18396855]
NPT27	Others	Unspecified		GI50	=	76130.0	nM	PMID[18691894]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9.1	nM	PMID[19284751]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	28.0	nM	PMID[12141852]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	630.0	nM	PMID[12141852]
NPT2	Others	Unspecified		Ratio IC50	=	20.0	n.a.	PMID[12141852]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[12141852]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	310.0	nM	PMID[9748386]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	310.0	nM	PMID[12762815]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	16.5	nM	PMID[18538567]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	293.5	nM	PMID[18538567]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.7	nM	PMID[18538567]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	48.5	nM	PMID[18538567]
NPT27	Others	Unspecified		IC50	>	40000.0	nM	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	99.2	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	14.7	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	9.7	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	>	99.9	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	30.0	day	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	99.9	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	22.3	day	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	9.3	day	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	99.8	%	PMID[18538567]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	15.7	day	PMID[18538567]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	200.0	nM	PMID[11141105]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	0.16	ug.mL-1	PMID[10075773]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.01	ug.mL-1	PMID[10217724]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.148	ug.mL-1	PMID[10217724]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	890.0	nM	PMID[19084293]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	76130.0	nM	PMID[19945197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	20000.0	nM	PMID[19945197]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	150.2	nM	PMID[19957999]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Ratio IC50	=	0.43	n.a.	PMID[19957999]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	29.6	nM	PMID[19957999]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	Ratio IC50	=	0.05	n.a.	PMID[19957999]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	21.0	nM	PMID[19926176]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	3153.95	n.a.	PMID[19926176]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	177.0	nM	PMID[19926176]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	374.19	n.a.	PMID[19926176]
NPT2	Others	Unspecified		IC50	=	1890000.0	nM	PMID[19926176]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[19926176]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	0.0	%	PMID[20034790]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	100.0	%	PMID[20034790]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Inhibition	=	98.1	%	PMID[20034790]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Inhibition	=	32.7	%	PMID[20034790]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Inhibition	=	1.31	%	PMID[20034790]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Inhibition	=	2.96	%	PMID[20034790]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	24.0	nM	PMID[20570512]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	38.0	nM	PMID[20570512]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	1.07	%	PMID[20570512]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	96.82	%	PMID[20570512]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.02063	ug.mL-1	PMID[20576433]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC80	=	36.11	ng/ml	PMID[20576433]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.2064	ug.mL-1	PMID[20576433]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Ratio IC50	=	0.1	n.a.	PMID[20576433]
NPT2	Others	Unspecified		IC50	=	1.3	ug.mL-1	PMID[20719524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	125.89	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1995.26	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	316.23	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10000.0	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1584.89	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	62.0	nM	PMID[18411319]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30.0	nM	PMID[20547797]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[22192590]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	602.3	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	307.38	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	510.46	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	249.84	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	475.66	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	226.21	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	19.23	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14.22	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	942.5	nM	PMID[23815186]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	634.3	nM	PMID[23815186]
NPT27	Others	Unspecified		Activity	=	17.2	%	PMID[23871905]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.02	ug.mL-1	PMID[23871905]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	68.4	%	PMID[23871905]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	84.34	%	PMID[23571415]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	99.18	%	PMID[23571415]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	>	2.0	ug.mL-1	PMID[24139941]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0966	ug.mL-1	PMID[24139941]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Ratio IC50	=	9.5	n.a.	PMID[24139941]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	0.0082	ug.mL-1	PMID[24139941]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	140.0	nM	PMID[24354322]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	21.8	nM	PMID[24354322]
NPT2	Others	Unspecified		Ratio IC50	=	22.0	n.a.	PMID[24602791]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	300.0	nM	PMID[24602791]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	13.8	nM	PMID[24602791]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	330.0	nM	PMID[24813729]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	110.0	nM	PMID[24813729]
NPT27	Others	Unspecified		IC50	>	140000.0	nM	PMID[24813729]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5.0	nM	PMID[25801154]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	6.0	nM	PMID[25801154]
NPT20576	SMALL MOLECULE	Heme	n.a.	IC50	=	6.0	equiv	PMID[25801154]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	0.034	ug.mL-1	PMID[25766631]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	66.0	nM	PMID[25766631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[25768697]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[25768697]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	192.0	nM	PMID[25768697]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	23.7	/uL	PMID[25835356]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	498.0	/uL	PMID[25835356]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	42607.0	/uL	PMID[25835356]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	0.0	%	PMID[25835356]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	180.0	nM	PMID[26638044]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1200.0	nM	PMID[26774925]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	IC50	=	11.0	nM	PMID[26774925]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	45454.54	n.a.	PMID[26774925]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	416.66	n.a.	PMID[26774925]
NPT2	Others	Unspecified		Ratio IC50	=	109.0	n.a.	PMID[26774925]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5.4	nM	PMID[28159413]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	125.85	n.a.	PMID[28159413]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8.3	nM	PMID[29185748]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	226.4	nM	PMID[29185748]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	150.3	nM	PMID[29185748]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Ratio IC50	=	27.3	n.a.	PMID[29185748]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Ratio IC50	=	21.9	n.a.	PMID[29185748]
NPT2	Others	Unspecified		IC50	=	26100.0	nM	PMID[29185748]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	18.9	ug.mL-1	PMID[28329730]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	50.0	nM	PMID[28282127]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8.8	nM	PMID[29216562]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	560.0	nM	PMID[29216562]
NPT24746	CELL-LINE	184B5	Homo sapiens	IC50	=	76130.0	nM	PMID[29232580]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Inhibition	=	88.5	%	PMID[29754074]
NPT35	Others	n.a.		Activity	=	95.8	%	PMID[29754074]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	5.84	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	193.0	nM	PMID[30530172]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	100.0	%	PMID[30530172]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	16.0	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	150.0	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	75.7	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	97.0	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	19.6	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	316.0	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	131.0	nM	PMID[30715882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	217.0	nM	PMID[30715882]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	24.58	%	DOI[10.6019/CHEMBL4495564]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.08	%	DOI[10.6019/CHEMBL4495565]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	Inhibition	=	97.9	%	PMID[32233487]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	188.0	nM	PMID[33479627]

☑ 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 NPC481920 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	1636
0.1-0.2	14774
0.2-0.3	17511
0.3-0.4	3846
0.4-0.5	2351
0.5-0.6	1614
0.6-0.7	718
0.7-0.8	241
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	2

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 NPC481920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1022
0.2-0.3	997
0.3-0.4	2051
0.4-0.5	2136
0.5-0.6	1780
0.6-0.7	618
0.7-0.8	127
0.8-0.85	7
0.85-0.9	4
0.9-0.95	3
0.95-1	4

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