NPASS Compound

Structure

CID54394 OpenBabel06191715392D 23 25 0 0 0 0 0 0 0 0999 V2000 4.3301 -2.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -0.8660 0.5000 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 -0.0000 2.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.06
Volume:	300.063
LogP:	2.553
LogD:	2.308
LogS:	-3.74
# Rotatable Bonds:	2
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	2.47
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.064
MDCK Permeability:	9.447854608879425e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.29076385498047%
Volume Distribution (VD):	0.646
Pgp-substrate:	8.09290885925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.675
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.542
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	7.014
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.611
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.785
Carcinogencity:	0.036
Eye Corrosion:	0.005
Eye Irritation:	0.916
Respiratory Toxicity:	0.136

Download Data

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

Natural Product: NPC54394

Natural Product ID:	NPC54394
*Common Name:**	Tamarixetin
IUPAC Name:	3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Synonyms:	4'-O-methylquercetin
Standard InCHIKey:	FPLMIPQZHHQWHN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
SMILES:	COc1ccc(cc1O)c1oc2cc(O)cc(c2c(=O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226034
PubChem CID:	5281699
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	North Sea	n.a.	PMID[14640534]
NPO17398	Cyperus teneriffae	Species	Cyperaceae	Eukaryota	n.a.	root	n.a.	PMID[21504148]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7853008]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	DOI[DOI: 10.1111/j.1574-6968.1992.tb05311.x]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1391	Zanthoxylum rubescens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15151	Syringa vulgaris	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11616	Vibrio parahaemolyticus	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9827	Indigofera linnaei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15972	Quercus gilva	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16526	Papularia sphaerosperma	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17398	Cyperus teneriffae	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15151	Syringa vulgaris	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13005	Aplophyllum telephioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5473	Streptomyces orinoci	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3488	Glossocalyx brevipes	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14896	Reaumuria mucronata	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11241	Arisarum vulgare	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1556	Gundelia tournefortii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16439	Alphitonia macrocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13257	Euphorbia officinarum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15762	Eucalyptus sieberiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1391	Zanthoxylum rubescens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15027	Helianthus divaricatus	Species	Asteraceae	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	1
IC50	30
Others	41

Activity Type	# Activity
Cell Line	8
CELL-LINE	6
Individual Protein	12
NON-MOLECULAR	9
Organism	12
Others	20
Protein Family	1
SINGLE PROTEIN	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	170.3	ug.mL-1	PMID[471286]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	1215.0	nM	PMID[471287]
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	120.0	nM	PMID[471287]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	20.0	nM	PMID[471287]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	TT	=	16.6	s	PMID[471290]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	PT	=	6.9	s	PMID[471290]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	APTT	=	49.8	s	PMID[471290]
NPT1628	Individual Protein	Thrombin	Oryctolagus cuniculus	Activity	=	7.5	g/L	PMID[471290]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	25.93	%	PMID[471291]
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	59.7	%	PMID[471292]
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	3040.0	nM	PMID[471294]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2630.0	nM	PMID[471294]
NPT1669	Cell Line	NCI-H1792	Homo sapiens	IC50	=	4060.0	nM	PMID[471294]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	>	50000.0	nM	PMID[471294]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	=	9930.0	nM	PMID[471294]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	14850.0	nM	PMID[471294]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1810.0	nM	PMID[471294]
NPT1426	Individual Protein	c-Jun N-terminal kinase 1	Homo sapiens	K	=	4.9	10'5/M	PMID[471299]
NPT281	Individual Protein	MAP kinase ERK1	Homo sapiens	K	=	6.31	10'4/M	PMID[471301]
NPT2	Others	Unspecified		IC50	=	4600.0	nM	PMID[471284]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[471285]
NPT2	Others	Unspecified		IC50	=	16400.0	nM	PMID[471285]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.1	ug.mL-1	PMID[471286]
NPT1	Others	Radical scavenging activity		EC50	>	100.0	ug	PMID[471289]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.18	%	PMID[471291]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	95.1	%	PMID[471293]
NPT27	Others	Unspecified		Activity	=	100.9	%	PMID[471293]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	97.5	%	PMID[471293]
NPT27	Others	Unspecified		Activity	=	103.6	%	PMID[471293]
NPT27	Others	Unspecified		Activity	=	103.0	%	PMID[471293]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	133.5	%	PMID[471293]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	125.6	%	PMID[471293]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	106.9	%	PMID[471293]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	97.9	%	PMID[471293]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4450.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3860.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7570.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21970.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12540.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24950.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19910.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[471294]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7970.0	nM	PMID[471294]
NPT2	Others	Unspecified		FC	=	1.52	n.a.	PMID[471296]
NPT2	Others	Unspecified		FC	=	1.32	n.a.	PMID[471296]
NPT27	Others	Unspecified		Activity	=	105.0	%	PMID[471296]
NPT27	Others	Unspecified		Activity	=	102.0	%	PMID[471296]
NPT27	Others	Unspecified		Activity	=	97.0	%	PMID[471296]
NPT27	Others	Unspecified		Activity	=	93.0	%	PMID[471296]
NPT27	Others	Unspecified		Activity	=	94.0	%	PMID[471296]
NPT27	Others	Unspecified		Activity	=	96.0	%	PMID[471296]
NPT2	Others	Unspecified		IC50	=	25000.0	nM	PMID[471298]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	80.0	%	PMID[471299]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	60.0	%	PMID[471299]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	93700.0	nM	PMID[471300]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	100000.0	nM	PMID[471300]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Inhibition	=	46.0	%	PMID[471300]
NPT21852	SINGLE PROTEIN	Dihydroorotate dehydrogenase	Homo sapiens	Inhibition	=	29.0	%	PMID[471300]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	53150.0	nM	PMID[471300]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	20250.0	nM	PMID[471300]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	46830.0	nM	PMID[471300]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	632000.0	nM	PMID[471301]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	632000.0	nM	PMID[471301]
NPT35	Others	n.a.		LogP	=	1.856	n.a.	PMID[471301]
NPT207	Protein Family	MAP kinase p38	Homo sapiens	K	=	4.64	10'4/M	PMID[471301]

☑ 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 NPC54394 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	515
0.1-0.2	2105
0.2-0.3	5258
0.3-0.4	11459
0.4-0.5	5508
0.5-0.6	3986
0.6-0.7	5117
0.7-0.8	4702
0.8-0.85	2012
0.85-0.9	1229
0.9-0.95	512
0.95-1	294

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC200740
1.0	High Similarity	NPC252933
1.0	High Similarity	NPC125062
0.9931	High Similarity	NPC55205
0.9931	High Similarity	NPC82325
0.9931	High Similarity	NPC279989
0.9863	High Similarity	NPC270620
0.9863	High Similarity	NPC236223
0.9863	High Similarity	NPC78326
0.9863	High Similarity	NPC179126
0.9862	High Similarity	NPC28274
0.9862	High Similarity	NPC50403
0.9862	High Similarity	NPC133953
0.9861	High Similarity	NPC270465
0.9861	High Similarity	NPC223579
0.9861	High Similarity	NPC87125
0.9861	High Similarity	NPC159103
0.9861	High Similarity	NPC287101
0.9861	High Similarity	NPC137062
0.9861	High Similarity	NPC52005
0.9861	High Similarity	NPC183950
0.9796	High Similarity	NPC201451
0.9796	High Similarity	NPC26227
0.9796	High Similarity	NPC44079
0.9795	High Similarity	NPC123886
0.9793	High Similarity	NPC50728
0.9793	High Similarity	NPC188871
0.9793	High Similarity	NPC166753
0.9793	High Similarity	NPC149127
0.9793	High Similarity	NPC286342
0.9792	High Similarity	NPC120464
0.973	High Similarity	NPC43243
0.973	High Similarity	NPC265511
0.973	High Similarity	NPC247017
0.973	High Similarity	NPC266960
0.973	High Similarity	NPC98661
0.973	High Similarity	NPC245546
0.973	High Similarity	NPC49824
0.9728	High Similarity	NPC58382
0.9728	High Similarity	NPC162351
0.9726	High Similarity	NPC260895
0.9726	High Similarity	NPC236769
0.9724	High Similarity	NPC48479
0.9724	High Similarity	NPC177298
0.9722	High Similarity	NPC12200
0.9722	High Similarity	NPC108406
0.9664	High Similarity	NPC203891
0.9664	High Similarity	NPC93376
0.9664	High Similarity	NPC174908
0.9664	High Similarity	NPC189179
0.9664	High Similarity	NPC305663
0.9664	High Similarity	NPC176665
0.9664	High Similarity	NPC224137
0.9664	High Similarity	NPC163524
0.9664	High Similarity	NPC227192
0.9664	High Similarity	NPC110070
0.9664	High Similarity	NPC101830
0.9664	High Similarity	NPC287979
0.9664	High Similarity	NPC75215
0.966	High Similarity	NPC83508
0.966	High Similarity	NPC301323
0.966	High Similarity	NPC293183
0.966	High Similarity	NPC275722
0.966	High Similarity	NPC301123
0.966	High Similarity	NPC275836
0.966	High Similarity	NPC198826
0.966	High Similarity	NPC60972
0.966	High Similarity	NPC162313
0.966	High Similarity	NPC25270
0.966	High Similarity	NPC57030
0.966	High Similarity	NPC241498
0.966	High Similarity	NPC239128
0.966	High Similarity	NPC100887
0.966	High Similarity	NPC120163
0.966	High Similarity	NPC187498
0.966	High Similarity	NPC131624
0.966	High Similarity	NPC256283
0.966	High Similarity	NPC71334
0.966	High Similarity	NPC212678
0.966	High Similarity	NPC222830
0.966	High Similarity	NPC39732
0.966	High Similarity	NPC188203
0.966	High Similarity	NPC156222
0.9658	High Similarity	NPC219330
0.9655	High Similarity	NPC195202
0.9655	High Similarity	NPC261548
0.9653	High Similarity	NPC179271
0.9653	High Similarity	NPC20791
0.96	High Similarity	NPC261004
0.96	High Similarity	NPC22472
0.96	High Similarity	NPC176300
0.96	High Similarity	NPC19687
0.96	High Similarity	NPC105242
0.96	High Similarity	NPC4481
0.96	High Similarity	NPC204854
0.96	High Similarity	NPC288669
0.96	High Similarity	NPC7846
0.96	High Similarity	NPC18607
0.96	High Similarity	NPC25495
0.96	High Similarity	NPC115798
0.96	High Similarity	NPC9609
0.96	High Similarity	NPC18772
0.96	High Similarity	NPC143828
0.96	High Similarity	NPC191459
0.96	High Similarity	NPC300943
0.96	High Similarity	NPC152166
0.96	High Similarity	NPC130894
0.96	High Similarity	NPC253634
0.9597	High Similarity	NPC326037
0.9597	High Similarity	NPC100916
0.9597	High Similarity	NPC55619
0.9597	High Similarity	NPC474520
0.9597	High Similarity	NPC13858
0.9597	High Similarity	NPC320825
0.9597	High Similarity	NPC200388
0.9597	High Similarity	NPC292107
0.9595	High Similarity	NPC176775
0.9595	High Similarity	NPC183878
0.9595	High Similarity	NPC145379
0.9595	High Similarity	NPC160951
0.9595	High Similarity	NPC274327
0.9595	High Similarity	NPC86485
0.9595	High Similarity	NPC255350
0.9595	High Similarity	NPC47781
0.9595	High Similarity	NPC22519
0.9595	High Similarity	NPC231018
0.9595	High Similarity	NPC69394
0.9592	High Similarity	NPC76376
0.9592	High Similarity	NPC225731
0.9586	High Similarity	NPC51443
0.9586	High Similarity	NPC33265
0.9586	High Similarity	NPC62536
0.9586	High Similarity	NPC74881
0.9533	High Similarity	NPC472438
0.9533	High Similarity	NPC7973
0.9533	High Similarity	NPC29841
0.9533	High Similarity	NPC67876
0.9533	High Similarity	NPC471479
0.9533	High Similarity	NPC78302
0.9533	High Similarity	NPC52530
0.9533	High Similarity	NPC471515
0.9533	High Similarity	NPC235215
0.953	High Similarity	NPC163780
0.953	High Similarity	NPC92659
0.953	High Similarity	NPC2476
0.953	High Similarity	NPC201136
0.953	High Similarity	NPC128863
0.953	High Similarity	NPC32557
0.953	High Similarity	NPC256612
0.953	High Similarity	NPC214138
0.953	High Similarity	NPC213622
0.953	High Similarity	NPC50715
0.953	High Similarity	NPC138360
0.953	High Similarity	NPC183597
0.953	High Similarity	NPC167815
0.953	High Similarity	NPC196439
0.953	High Similarity	NPC146165
0.953	High Similarity	NPC4455
0.953	High Similarity	NPC20830
0.953	High Similarity	NPC227325
0.953	High Similarity	NPC56786
0.953	High Similarity	NPC80534
0.953	High Similarity	NPC133392
0.953	High Similarity	NPC189960
0.953	High Similarity	NPC280339
0.9527	High Similarity	NPC219582
0.9527	High Similarity	NPC27208
0.9527	High Similarity	NPC236637
0.9527	High Similarity	NPC157784
0.9527	High Similarity	NPC63187
0.9527	High Similarity	NPC37684
0.9527	High Similarity	NPC142540
0.9527	High Similarity	NPC471982
0.9527	High Similarity	NPC304954
0.9527	High Similarity	NPC302950
0.9524	High Similarity	NPC184136
0.9524	High Similarity	NPC306821
0.9521	High Similarity	NPC119059
0.9517	High Similarity	NPC169749
0.9514	High Similarity	NPC279121
0.947	High Similarity	NPC193842
0.947	High Similarity	NPC280680
0.947	High Similarity	NPC55738
0.9467	High Similarity	NPC474638
0.9467	High Similarity	NPC178854
0.9467	High Similarity	NPC471500
0.9467	High Similarity	NPC250922
0.9467	High Similarity	NPC268161
0.9463	High Similarity	NPC250822
0.9463	High Similarity	NPC18727
0.9463	High Similarity	NPC246204
0.9463	High Similarity	NPC75279
0.9463	High Similarity	NPC141212
0.9463	High Similarity	NPC276409
0.9459	High Similarity	NPC304295
0.9459	High Similarity	NPC226973
0.9459	High Similarity	NPC205046
0.9459	High Similarity	NPC59162
0.9459	High Similarity	NPC31363
0.9459	High Similarity	NPC208043

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 NPC54394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1009
0.2-0.3	1890
0.3-0.4	2655
0.4-0.5	1672
0.5-0.6	954
0.6-0.7	339
0.7-0.8	99
0.8-0.85	37
0.85-0.9	9
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9653	High Similarity	NPD1512	Approved
0.9595	High Similarity	NPD2801	Approved
0.9527	High Similarity	NPD1934	Approved
0.9514	High Similarity	NPD1511	Approved
0.9338	High Similarity	NPD3882	Suspended
0.9272	High Similarity	NPD3817	Phase 2
0.9205	High Similarity	NPD2393	Clinical (unspecified phase)
0.9167	High Similarity	NPD6166	Phase 2
0.9167	High Similarity	NPD6167	Clinical (unspecified phase)
0.9167	High Similarity	NPD6168	Clinical (unspecified phase)
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.8882	High Similarity	NPD6797	Phase 2
0.8875	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7251	Discontinued
0.882	High Similarity	NPD7472	Approved
0.8812	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD7808	Phase 3
0.8773	High Similarity	NPD4338	Clinical (unspecified phase)
0.8704	High Similarity	NPD7074	Phase 3
0.8609	High Similarity	NPD6799	Approved
0.8581	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1510	Phase 2
0.8544	High Similarity	NPD7075	Discontinued
0.8523	High Similarity	NPD1549	Phase 2
0.8516	High Similarity	NPD4380	Phase 2
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.8389	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD5494	Approved
0.8312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1607	Approved
0.8303	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5402	Approved
0.8299	Intermediate Similarity	NPD943	Approved
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1247	Approved
0.8261	Intermediate Similarity	NPD919	Approved
0.8239	Intermediate Similarity	NPD1465	Phase 2
0.8205	Intermediate Similarity	NPD5403	Approved
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5401	Approved
0.8171	Intermediate Similarity	NPD3926	Phase 2
0.8151	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8082	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1613	Approved
0.8052	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD447	Suspended
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7871	Intermediate Similarity	NPD2800	Approved
0.7862	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3027	Phase 3
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD1933	Approved
0.7758	Intermediate Similarity	NPD3749	Approved
0.7738	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3748	Approved
0.7718	Intermediate Similarity	NPD9494	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6190	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD920	Approved
0.7628	Intermediate Similarity	NPD2344	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2533	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7593	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD1203	Approved
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7564	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD3226	Approved
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6651	Approved
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD422	Phase 1
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7389	Intermediate Similarity	NPD2799	Discontinued
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7383	Intermediate Similarity	NPD9717	Approved
0.7377	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.733	Intermediate Similarity	NPD7685	Pre-registration
0.732	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.7305	Intermediate Similarity	NPD37	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.729	Intermediate Similarity	NPD6233	Phase 2
0.7285	Intermediate Similarity	NPD3225	Approved
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1608	Approved
0.7255	Intermediate Similarity	NPD3018	Phase 2
0.7237	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5242	Approved
0.7222	Intermediate Similarity	NPD2354	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7205	Intermediate Similarity	NPD2654	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4363	Phase 3
0.7174	Intermediate Similarity	NPD4360	Phase 2
0.7153	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD6385	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7124	Intermediate Similarity	NPD3266	Approved
0.7124	Intermediate Similarity	NPD3267	Approved
0.7118	Intermediate Similarity	NPD5353	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD9268	Approved
0.7105	Intermediate Similarity	NPD2982	Phase 2
0.7105	Intermediate Similarity	NPD2983	Phase 2
0.7102	Intermediate Similarity	NPD2163	Approved
0.7101	Intermediate Similarity	NPD6844	Discontinued
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7091	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1201	Approved
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7067	Intermediate Similarity	NPD17	Approved
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8312	Approved
0.7051	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD4625	Phase 3
0.7047	Intermediate Similarity	NPD9545	Approved
0.7043	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4361	Phase 2
0.7039	Intermediate Similarity	NPD2981	Phase 2
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7031	Intermediate Similarity	NPD7584	Approved
0.7027	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD1558	Phase 1
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7013	Intermediate Similarity	NPD1470	Approved
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.6993	Remote Similarity	NPD4749	Approved
0.6988	Remote Similarity	NPD3146	Approved
0.6988	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4340	Discontinued

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