NPASS Compound

Structure

NPC479190 OpenBabel06302216032D 36 40 0 0 1 0 0 0 0 0999 V2000 -7.8988 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 3.9945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 2.9945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8736 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0399 -1.6092 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2478 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2424 -2.6918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6491 -1.7783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9060 -1.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 -0.7957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 -0.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5097 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4052 -1.9713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4917 -2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -1.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7691 -2.1970 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.2142 -2.5591 0.0000 Cl 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 2 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 4 9 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 36 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 23 27 1 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 25 26 1 0 0 0 0 26 27 2 0 0 0 0 28 33 2 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 31 35 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.23
Volume:	568.994
LogP:	2.878
LogD:	2.425
LogS:	-3.861
# Rotatable Bonds:	8
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.738
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.431
MDCK Permeability:	4.973503382643685e-05
Pgp-inhibitor:	0.608
Pgp-substrate:	0.758
Human Intestinal Absorption (HIA):	0.54
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	78.0573501586914%
Volume Distribution (VD):	1.54
Pgp-substrate:	22.408666610717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.26
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.484
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	3.147
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.606
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.396
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC479190

Natural Product ID:	NPC479190
*Common Name:**	XMAYWYJOQHXEEK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XMAYWYJOQHXEEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
SMILES:	CC(=O)N1CCN(CC1)c1ccc(cc1)OCC1COC(Cn2ccnc2)(c2ccc(cc2Cl)Cl)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	3823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002389] Diazinanes [CHEMONTID:0000189] Piperazines [CHEMONTID:0001984] Phenylpiperazines

*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
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	Stems	n.a.	n.a.	PMID[14695805]
NPO40484	Corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479383]
NPO40484	Corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17391049]
NPO11619	Phytolacca tetramera hauman	Strain	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816139]
NPO40101	Dendrodochium sp.	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24749951]
NPO6232.59	Streptomyces griseus var. autotrophicus	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2509636]
NPO26173	Anomospermum grandifolium	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11619	Phytolacca tetramera hauman	Strain	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	61
Ki	4
MIC	66
Others	107

Activity Type	# Activity
Cell Line	5
Individual Protein	75
NON-MOLECULAR	15
Organism	119
Others	18
SINGLE PROTEIN	5
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	=	16300.0	nM	PMID[22328583]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	IC50	=	10100.0	nM	PMID[22328583]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	IC50	=	8940.0	nM	PMID[22328583]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	26000.0	nM	PMID[22328583]
NPT1463	Individual Protein	Cytochrome P450 2J2	Homo sapiens	Activity	=	5.8	%	PMID[22328583]
NPT1463	Individual Protein	Cytochrome P450 2J2	Homo sapiens	Activity	=	5.4	%	PMID[22328583]
NPT628	Individual Protein	Cytochrome P450 2C8	Homo sapiens	IC50	=	2450.0	nM	PMID[22328583]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	<	100.0	nM	PMID[22328583]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Activity	=	70.0	%	PMID[22517972]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Activity	=	80.0	%	PMID[22517972]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	49.0	nM	PMID[23355637]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	11.0	nM	PMID[23355637]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	7.0	nM	PMID[23355637]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	9.8	nM	PMID[23355637]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	180.0	nM	PMID[26204510]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	95.16	%	PMID[26631442]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	140.0	nM	PMID[26900658]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	280.0	nM	PMID[27105029]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	95.37	%	PMID[27229618]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	4.0	nM	PMID[26962886]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	1.0	nM	PMID[26962886]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	100.0	%	PMID[27050842]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	240.0	nM	PMID[27145071]
NPT6403	Individual Protein	Cytochrome P450 17A1	Rattus norvegicus	IC50	=	320.0	nM	PMID[27209562]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	34.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	53.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	70.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	82.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	90.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	94.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	37.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	57.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	74.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	85.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	92.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	95.0	%	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	9.1	nM	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	7.4	nM	PMID[27548392]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Activity	=	17.0	%	PMID[27606885]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	28.5	nM	PMID[27606885]
NPT3161	Individual Protein	Cytochrome P450 11B1	Homo sapiens	IC50	=	116.0	nM	PMID[27789139]
NPT6441	Individual Protein	Cytochrome P450 21	Homo sapiens	IC50	=	4300.0	nM	PMID[27789139]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	1600.0	nM	PMID[27789139]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	146.0	nM	PMID[27789139]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	133.0	nM	PMID[27789139]
NPT3159	Individual Protein	Cytochrome P450 17A1	Homo sapiens	IC50	=	48.0	nM	PMID[27789139]
NPT3159	Individual Protein	Cytochrome P450 17A1	Homo sapiens	IC50	=	93.0	nM	PMID[27789139]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	31.7	nM	PMID[27955926]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	15.0	nM	PMID[28337324]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	18.0	nM	PMID[28337324]
NPT613	Individual Protein	Solute carrier family 22 member 1	Homo sapiens	IC50	=	2600.0	nM	PMID[28230985]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	>	85.0	%	PMID[28400237]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	200.0	nM	PMID[28400237]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	80000.0	nM	PMID[29243920]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	40.0	nM	PMID[29251928]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	IC50	>	133000.0	nM	PMID[23956101]
NPT1249	Individual Protein	Canalicular multispecific organic anion transporter 2	Homo sapiens	IC50	>	133000.0	nM	PMID[23956101]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	69000.0	nM	PMID[23956101]
NPT6124	Individual Protein	Cytochrome P450 24A1	Homo sapiens	IC50	=	500.0	nM	PMID[28886997]
NPT6124	Individual Protein	Cytochrome P450 24A1	Homo sapiens	IC50	=	500.0	nM	PMID[28601511]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	35.9	nM	PMID[28558334]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	140.0	nM	PMID[29681486]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	22.0	nM	PMID[29779669]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	13.0	nM	PMID[29779669]
NPT492	Cell Line	Caco-2	Homo sapiens	CC50	=	28620.0	nM	DOI[10.21203/rs.3.rs-23951/v1]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	182.6	nM	PMID[31288127]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	<	40.0	%	PMID[31288127]
NPT2615	Cell Line	HEK-293T	Homo sapiens	Inhibition	<	40.0	%	PMID[31288127]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT18114	SINGLE PROTEIN	Cytochrome P450 26A1	Homo sapiens	IC50	=	12000.0	nM	PMID[16279770]
NPT27	Others	Unspecified		Activity	=	65.0	%	PMID[18583127]
NPT27	Others	Unspecified		Activity	<	5.0	%	PMID[17875991]
NPT1819	Organism	Microsporum canis	Arthroderma otae	GI	=	10.0	ug ml-1	PMID[490531]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	GI	=	0.1	ug ml-1	PMID[490531]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	GI	=	1.0	ug ml-1	PMID[490531]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	GI	=	1.0	ug ml-1	PMID[490531]
NPT186	Organism	Candida tropicalis	Candida tropicalis	GI	=	1.0	ug ml-1	PMID[490531]
NPT20	Organism	Candida albicans	Candida albicans	GI	=	10.0	ug ml-1	PMID[490531]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	GI	=	100.0	ug ml-1	PMID[490531]
NPT1155	Organism	Sporothrix schenckii	Sporothrix schenckii	GI	=	1.0	ug ml-1	PMID[490531]
NPT6267	Organism	Saprolegnia	Saprolegnia	GI	=	1.0	ug ml-1	PMID[490531]
NPT6646	Organism	Phialophora verrucosa	Phialophora verrucosa	GI	=	1.0	ug ml-1	PMID[490531]
NPT6472	Organism	Erysipelothrix rhusiopathiae	Erysipelothrix rhusiopathiae	GI	=	10.0	ug ml-1	PMID[490531]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	GI	=	100.0	ug ml-1	PMID[490531]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	GI	=	10.0	ug ml-1	PMID[490531]
NPT1819	Organism	Microsporum canis	Arthroderma otae	GI	=	1.0	ug ml-1	PMID[490531]
NPT186	Organism	Candida tropicalis	Candida tropicalis	GI	=	0.1	ug ml-1	PMID[490531]
NPT20	Organism	Candida albicans	Candida albicans	GI	=	1.0	ug ml-1	PMID[490531]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	GI	=	10.0	ug ml-1	PMID[490531]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	100.0	%	PMID[490531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	60.0	%	PMID[490531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56450.0	nM	DOI[10.6019/CHEMBL3392926]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	33120.0	nM	DOI[10.6019/CHEMBL3392926]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	270.0	nM	DOI[10.6019/CHEMBL3392926]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	50990.0	nM	DOI[10.6019/CHEMBL3392926]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	18820.0	nM	DOI[10.6019/CHEMBL3392926]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	38760.0	nM	DOI[10.6019/CHEMBL3392926]
NPT27	Others	Unspecified		Ratio	=	46.0	n.a.	PMID[21051535]
NPT27	Others	Unspecified		Ratio	=	0.3	n.a.	PMID[21051535]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	IC50	=	13000.0	nM	PMID[21030469]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	IC50	=	27000.0	nM	PMID[21030469]
NPT712	Individual Protein	Bile salt export pump	Rattus norvegicus	IC50	=	15600.0	nM	PMID[21965623]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	2900.0	nM	PMID[21965623]
NPT27	Others	Unspecified		Ratio	=	10.0	n.a.	PMID[21051535]
NPT27	Others	Unspecified		Ratio	=	-31.0	n.a.	PMID[21051535]
NPT24846	SINGLE PROTEIN	Cytochrome P450 4F2	Homo sapiens	Ki	=	740.0	nM	PMID[21045201]
NPT24846	SINGLE PROTEIN	Cytochrome P450 4F2	Homo sapiens	IC50	=	1600.0	nM	PMID[21045201]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3650	Organism	Aspergillus versicolor	Aspergillus versicolor	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3650	Organism	Aspergillus versicolor	Aspergillus versicolor	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	475.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MFC99.5	=	570.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MIC	=	380.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MFC99.5	=	380.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	38.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT20	Organism	Candida albicans	Candida albicans	MFC99.5	=	95.0	10'-2 umol/ml	DOI[10.1039/C4MD00399C]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	88.48	%	PMID[26631442]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	73.39	%	PMID[26631442]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	2.0	ug.mL-1	PMID[26562544]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	2.0	ug.mL-1	PMID[26562544]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	2.0	ug.mL-1	PMID[26562544]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	4.0	ug.mL-1	PMID[26562544]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	2.0	ug.mL-1	PMID[26562544]
NPT3700	Organism	Candida sake	Candida sake	MIC	=	4.0	ug.mL-1	PMID[26562544]
NPT2600	Organism	Fusarium solani	Fusarium solani	MIC	=	62.5	ug.mL-1	PMID[26706351]
NPT1262	Organism	Aspergillus parasiticus	Aspergillus parasiticus	MIC	=	7.81	ug.mL-1	PMID[26706351]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	31.25	ug.mL-1	PMID[26706351]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	15.62	ug.mL-1	PMID[26706351]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	15.62	ug.mL-1	PMID[26706351]
NPT3679	Organism	Candida zeylanoides	Candida zeylanoides	MIC	=	250.0	ug.mL-1	PMID[26706351]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	125.0	ug.mL-1	PMID[26706351]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	125.0	ug.mL-1	PMID[26706351]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	62.5	ug.mL-1	PMID[26706351]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	62.5	ug.mL-1	PMID[26706351]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	2.0	ug.mL-1	PMID[27100030]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	2.0	ug.mL-1	PMID[27100030]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	2.0	ug.mL-1	PMID[27100030]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	4.0	ug.mL-1	PMID[27100030]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	2.0	ug.mL-1	PMID[27100030]
NPT3700	Organism	Candida sake	Candida sake	MIC	=	4.0	ug.mL-1	PMID[27100030]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	3.125	ug.mL-1	PMID[27769618]
NPT610	Others	Molecular identity unknown		MIC	=	3.125	ug.mL-1	PMID[27769618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	29.0	mm	PMID[27448921]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	31.0	mm	PMID[27448921]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	34.0	mm	PMID[27448921]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	37.0	mm	PMID[27448921]
NPT610	Others	Molecular identity unknown		IZ	=	34.0	mm	PMID[27448921]
NPT610	Others	Molecular identity unknown		IZ	=	36.0	mm	PMID[27448921]
NPT610	Others	Molecular identity unknown		IZ	=	37.0	mm	PMID[27448921]
NPT610	Others	Molecular identity unknown		IZ	=	39.0	mm	PMID[27448921]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	6.25	ug.mL-1	PMID[27448921]
NPT610	Others	Molecular identity unknown		MIC	=	12.5	ug.mL-1	PMID[27448921]
NPT27	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[27789139]
NPT27	Others	Unspecified		Ratio IC50	=	1.4	n.a.	PMID[27789139]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	25.42	mm	PMID[27494167]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	28.35	mm	PMID[27494167]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	6.25	ug	PMID[27494167]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	12.5	ug	PMID[27494167]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	0.39	ug.mL-1	PMID[27744188]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	3400.0	nM	PMID[20829430]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	3400.0	nM	PMID[24799086]
NPT1593	Tissue	Liver	Rattus norvegicus	IC50	=	80.6	nM	PMID[24799086]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	4100.0	nM	PMID[22961681]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	0.25	ug.mL-1	PMID[28880552]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	0.25	ug.mL-1	PMID[28880552]
NPT6962	Organism	Trichophyton verrucosum	Trichophyton verrucosum	MIC	=	16.0	ug.mL-1	PMID[28880552]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	16.0	ug.mL-1	PMID[28880552]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	28.0	ug.mL-1	PMID[28539243]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	MIC	=	27.0	ug.mL-1	PMID[28539243]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC	=	24.0	ug.mL-1	PMID[28539243]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	38.0	mm	PMID[28539243]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	32.0	mm	PMID[28539243]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	22.0	mm	PMID[28539243]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	23.0	mm	PMID[28539243]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	34.0	mm	PMID[28539243]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	31.0	mm	PMID[28539243]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	25.0	mm	PMID[28539243]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	21.0	mm	PMID[28539243]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	37.0	mm	PMID[28539243]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	34.0	mm	PMID[28539243]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	28.0	mm	PMID[28539243]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	24.0	mm	PMID[28539243]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC80	=	0.5	ug.mL-1	PMID[29243920]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC80	=	2.0	ug.mL-1	PMID[29243920]
NPT6962	Organism	Trichophyton verrucosum	Trichophyton verrucosum	MIC80	=	0.0625	ug.mL-1	PMID[29243920]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC80	=	0.0625	ug.mL-1	PMID[29243920]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	3400.0	nM	PMID[23956101]
NPT2	Others	Unspecified		Ratio	=	0.381	n.a.	PMID[23956101]
NPT2	Others	Unspecified		Ratio	=	0.019	n.a.	PMID[23956101]
NPT20	Organism	Candida albicans	Candida albicans	MIC80	=	0.25	ug.mL-1	PMID[28372907]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC80	=	0.125	ug.mL-1	PMID[28372907]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC80	=	0.5	ug.mL-1	PMID[28372907]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC80	=	0.0625	ug.mL-1	PMID[28372907]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC80	=	0.0625	ug.mL-1	PMID[28372907]
NPT2	Others	Unspecified		MIC80	=	4.0	ug.mL-1	PMID[28372907]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC80	=	1.0	ug.mL-1	PMID[28372907]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC80	=	1.0	ug.mL-1	PMID[28372907]
NPT26198	SINGLE PROTEIN	25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial	Homo sapiens	IC50	=	340.0	nM	PMID[28886997]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	87.05	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	2360.0	nM	DOI[10.21203/rs.3.rs-23951/v1]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.007	ug.mL-1	PMID[31288127]
NPT2580	Organism	Candida dubliniensis	Candida dubliniensis	MIC	=	0.007	ug.mL-1	PMID[31288127]
NPT2578	Organism	Pichia guilliermondii	Meyerozyma guilliermondii	MIC	=	0.007	ug.mL-1	PMID[31288127]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	0.007	ug.mL-1	PMID[31288127]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	0.06	ug.mL-1	PMID[31288127]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	1.0	ug.mL-1	PMID[31288127]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	4.0	ug.mL-1	PMID[31288127]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	0.125	ug.mL-1	PMID[31288127]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	17.52	%	DOI[10.6019/CHEMBL4495564]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.16	%	DOI[10.6019/CHEMBL4495565]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	312.5	nM	DOI[10.6019/CHEMBL4296181]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	20000.0	nM	DOI[10.6019/CHEMBL4296181]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	20000.0	nM	DOI[10.6019/CHEMBL4296181]

☑ 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 NPC479190 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	611
0.1-0.2	4323
0.2-0.3	13160
0.3-0.4	14641
0.4-0.5	7411
0.5-0.6	2383
0.6-0.7	157
0.7-0.8	6
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	3

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 NPC479190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	677
0.2-0.3	935
0.3-0.4	1687
0.4-0.5	3099
0.5-0.6	1940
0.6-0.7	493
0.7-0.8	28
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	2

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