NPASS Compound

Structure

CID239113 OpenBabel06191716042D 29 33 0 0 0 0 0 0 0 0999 V2000 2.9345 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -1.0827 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 -3.2127 -4.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 -2.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 10 29 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 21 2 0 0 0 0 15 18 2 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 29 1 0 0 0 0 19 20 2 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.11
Volume:	384.089
LogP:	3.896
LogD:	3.189
LogS:	-5.893
# Rotatable Bonds:	4
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.553
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212
MDCK Permeability:	6.617463805014268e-05
Pgp-inhibitor:	0.522
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	87.01522064208984%
Volume Distribution (VD):	0.881
Pgp-substrate:	2.8456573486328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.419
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.385
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	11.886
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.865
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.352
Skin Sensitization:	0.059
Carcinogencity:	0.929
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC239113

Natural Product ID:	NPC239113
*Common Name:**	Justicidin A
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:	Justicidin A; Justicidin-A
Standard InCHIKey:	ANFSXHKDCKWWDB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
SMILES:	COc1cc2c(c3ccc4c(c3)OCO4)c3C(=O)OCc3c(c2cc1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508532
PubChem CID:	159982
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395523]
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425143]
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087610]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11830167]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908984]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	Roots	n.a.	n.a.	PMID[2089115]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23006989]
NPO33442	phyllanthus poilanei	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[24937209]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734816]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988600]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16045.1	Justicia procumbens var. leucantha	Varieties	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16045.1	Justicia procumbens var. leucantha	Varieties	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25670	Aspergillus foveolatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO796	Diphasiastrum alpinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23369	Hertia intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24192	Piptoporus australiensis	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20023	Uncaria gambier	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22467	Kippistia suaedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24448	Haplopappus ciliatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23325	Doris verrucosa	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19177	Euphorbia franckiana	Species	Euphorbiaceae	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
ED50	15
IC50	4
MIC	1
Others	9

Activity Type	# Activity
Cell Line	19
CELL-LINE	1
NON-MOLECULAR	4
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	150.0	%	PMID[463159]
NPT91	Cell Line	KB	Homo sapiens	ED50	<	1.0	ug ml-1	PMID[463159]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	ED50	=	3.0	10'-3 ug/ml	PMID[463160]
NPT2245	Cell Line	SiHa	Homo sapiens	ED50	=	7.4	10'-3 ug/ml	PMID[463160]
NPT65	Cell Line	HepG2	Homo sapiens	ED50	=	2.0	10'-2 ug/ml	PMID[463160]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.9	10'-1 ug/ml	PMID[463160]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	20.3	%	PMID[463160]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	19.8	%	PMID[463160]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	-6.0	%	PMID[463160]
NPT91	Cell Line	KB	Homo sapiens	ED50	<	1.0	ug ml-1	PMID[463163]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	-157.5	%	PMID[463160]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	-340.5	%	PMID[463160]
NPT550	Cell Line	T-24	Homo sapiens	ED50	=	2.0	10'-3 ug/ml	PMID[463164]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	ED50	=	3.0	10'-3 ug/ml	PMID[463164]
NPT2245	Cell Line	SiHa	Homo sapiens	ED50	=	7.4	10'-3 ug/ml	PMID[463164]
NPT2428	Cell Line	HT-3	Homo sapiens	ED50	=	1.8	10'-3 ug/ml	PMID[463164]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	163000.0	nM	PMID[463165]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[463166]
NPT2428	Cell Line	HT-3	Homo sapiens	IC50	=	0.0018	ug.mL-1	PMID[463167]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	10.0	%	PMID[463158]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	48.0	%	PMID[463158]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	22.7	10'-3 ug/ml	PMID[463160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.9	10'-2 ug/ml	PMID[463160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.4	10'-2 ug/ml	PMID[463160]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	31700.0	nM	PMID[463161]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	=	650.0	nM	PMID[463162]
NPT27	Others	Unspecified		Activity	=	166.0	uM	PMID[463162]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.2	10'-3 ug/ml	PMID[463164]
NPT27	Others	Unspecified		ED50	=	22.7	10'-3 ug/ml	PMID[463164]

☑ 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 NPC239113 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	429
0.1-0.2	1740
0.2-0.3	3568
0.3-0.4	9447
0.4-0.5	9290
0.5-0.6	3343
0.6-0.7	7334
0.7-0.8	7219
0.8-0.85	248
0.85-0.9	46
0.9-0.95	24
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC115123
0.9801	High Similarity	NPC78944
0.98	High Similarity	NPC19600
0.9673	High Similarity	NPC22130
0.9673	High Similarity	NPC116838
0.9608	High Similarity	NPC15212
0.9605	High Similarity	NPC474043
0.9536	High Similarity	NPC234730
0.9487	High Similarity	NPC471923
0.947	High Similarity	NPC54179
0.9463	High Similarity	NPC475722
0.9427	High Similarity	NPC475453
0.9427	High Similarity	NPC473531
0.9419	High Similarity	NPC198796
0.9396	High Similarity	NPC127827
0.9363	High Similarity	NPC174734
0.9363	High Similarity	NPC474042
0.9351	High Similarity	NPC125713
0.9346	High Similarity	NPC473900
0.9338	High Similarity	NPC118332
0.925	High Similarity	NPC474075
0.925	High Similarity	NPC473697
0.925	High Similarity	NPC292712
0.925	High Similarity	NPC471920
0.925	High Similarity	NPC471922
0.925	High Similarity	NPC471921
0.925	High Similarity	NPC312006
0.925	High Similarity	NPC129930
0.925	High Similarity	NPC20114
0.925	High Similarity	NPC114550
0.9245	High Similarity	NPC117911
0.92	High Similarity	NPC181464
0.9193	High Similarity	NPC184624
0.9161	High Similarity	NPC143328
0.9139	High Similarity	NPC24193
0.9108	High Similarity	NPC191352
0.9108	High Similarity	NPC258322
0.9097	High Similarity	NPC109765
0.908	High Similarity	NPC196771
0.9045	High Similarity	NPC65784
0.9038	High Similarity	NPC202495
0.9024	High Similarity	NPC35266
0.897	High Similarity	NPC275690
0.897	High Similarity	NPC161609
0.8954	High Similarity	NPC149505
0.8902	High Similarity	NPC193377
0.8896	High Similarity	NPC210642
0.8896	High Similarity	NPC13985
0.8882	High Similarity	NPC304687
0.8882	High Similarity	NPC65574
0.8882	High Similarity	NPC101755
0.8882	High Similarity	NPC104024
0.8882	High Similarity	NPC80230
0.8868	High Similarity	NPC319749
0.8854	High Similarity	NPC261484
0.8846	High Similarity	NPC273578
0.8839	High Similarity	NPC104353
0.8831	High Similarity	NPC300983
0.8827	High Similarity	NPC79322
0.8812	High Similarity	NPC280778
0.8812	High Similarity	NPC19948
0.881	High Similarity	NPC114120
0.881	High Similarity	NPC167045
0.8797	High Similarity	NPC76458
0.8797	High Similarity	NPC82733
0.8766	High Similarity	NPC177476
0.8766	High Similarity	NPC262455
0.875	High Similarity	NPC209411
0.875	High Similarity	NPC239890
0.8742	High Similarity	NPC15764
0.8734	High Similarity	NPC301897
0.8726	High Similarity	NPC348849
0.8726	High Similarity	NPC178195
0.8706	High Similarity	NPC286301
0.8706	High Similarity	NPC313063
0.8704	High Similarity	NPC477884
0.8701	High Similarity	NPC40654
0.8701	High Similarity	NPC262804
0.8688	High Similarity	NPC474770
0.8688	High Similarity	NPC96593
0.8688	High Similarity	NPC139876
0.8679	High Similarity	NPC19947
0.8679	High Similarity	NPC207584
0.8654	High Similarity	NPC303519
0.865	High Similarity	NPC320471
0.865	High Similarity	NPC83049
0.865	High Similarity	NPC118162
0.8634	High Similarity	NPC296540
0.8634	High Similarity	NPC309335
0.8634	High Similarity	NPC288149
0.8625	High Similarity	NPC325122
0.8616	High Similarity	NPC237946
0.8616	High Similarity	NPC32373
0.8609	High Similarity	NPC162851
0.8609	High Similarity	NPC246474
0.8609	High Similarity	NPC218092
0.8606	High Similarity	NPC52598
0.8598	High Similarity	NPC311912
0.859	High Similarity	NPC261322
0.858	High Similarity	NPC61141
0.8571	High Similarity	NPC470637
0.8562	High Similarity	NPC163527
0.8562	High Similarity	NPC181168
0.8562	High Similarity	NPC115281
0.8553	High Similarity	NPC176586
0.8553	High Similarity	NPC3273
0.8553	High Similarity	NPC210354
0.8545	High Similarity	NPC88557
0.8544	High Similarity	NPC308555
0.8509	High Similarity	NPC68619
0.8506	High Similarity	NPC471305
0.85	High Similarity	NPC261090
0.8497	Intermediate Similarity	NPC125134
0.8497	Intermediate Similarity	NPC86455
0.8497	Intermediate Similarity	NPC137920
0.8491	Intermediate Similarity	NPC30009
0.8491	Intermediate Similarity	NPC103197
0.8481	Intermediate Similarity	NPC220577
0.8477	Intermediate Similarity	NPC233780
0.8476	Intermediate Similarity	NPC474301
0.8457	Intermediate Similarity	NPC268718
0.8457	Intermediate Similarity	NPC47623
0.8457	Intermediate Similarity	NPC119910
0.8457	Intermediate Similarity	NPC150943
0.8457	Intermediate Similarity	NPC91634
0.8452	Intermediate Similarity	NPC87295
0.8447	Intermediate Similarity	NPC167098
0.8447	Intermediate Similarity	NPC296044
0.8442	Intermediate Similarity	NPC191158
0.8442	Intermediate Similarity	NPC177644
0.8442	Intermediate Similarity	NPC475000
0.8442	Intermediate Similarity	NPC474036
0.8438	Intermediate Similarity	NPC254163
0.8431	Intermediate Similarity	NPC40237
0.8431	Intermediate Similarity	NPC151423
0.8428	Intermediate Similarity	NPC245948
0.8428	Intermediate Similarity	NPC477377
0.8408	Intermediate Similarity	NPC85141
0.8405	Intermediate Similarity	NPC109238
0.8405	Intermediate Similarity	NPC99968
0.8405	Intermediate Similarity	NPC152424
0.8405	Intermediate Similarity	NPC100465
0.8397	Intermediate Similarity	NPC153620
0.8397	Intermediate Similarity	NPC24257
0.8393	Intermediate Similarity	NPC72455
0.8393	Intermediate Similarity	NPC477881
0.8389	Intermediate Similarity	NPC205915
0.8387	Intermediate Similarity	NPC474158
0.8385	Intermediate Similarity	NPC477380
0.8385	Intermediate Similarity	NPC155063
0.8377	Intermediate Similarity	NPC474288
0.8373	Intermediate Similarity	NPC471180
0.8365	Intermediate Similarity	NPC475229
0.8365	Intermediate Similarity	NPC477378
0.8364	Intermediate Similarity	NPC222531
0.8354	Intermediate Similarity	NPC144843
0.8354	Intermediate Similarity	NPC474305
0.8344	Intermediate Similarity	NPC160425
0.8333	Intermediate Similarity	NPC193779
0.8333	Intermediate Similarity	NPC477885
0.8323	Intermediate Similarity	NPC188962
0.8323	Intermediate Similarity	NPC92693
0.8323	Intermediate Similarity	NPC42871
0.8323	Intermediate Similarity	NPC472835
0.8323	Intermediate Similarity	NPC478238
0.8323	Intermediate Similarity	NPC41853
0.8323	Intermediate Similarity	NPC218841
0.8323	Intermediate Similarity	NPC202249
0.8313	Intermediate Similarity	NPC144162
0.8303	Intermediate Similarity	NPC116759
0.8303	Intermediate Similarity	NPC477689
0.8303	Intermediate Similarity	NPC14294
0.8303	Intermediate Similarity	NPC475865
0.8302	Intermediate Similarity	NPC474975
0.8293	Intermediate Similarity	NPC115624
0.8291	Intermediate Similarity	NPC474306
0.8291	Intermediate Similarity	NPC475848
0.8289	Intermediate Similarity	NPC196420
0.8284	Intermediate Similarity	NPC316539
0.8274	Intermediate Similarity	NPC477883
0.8274	Intermediate Similarity	NPC135370
0.8269	Intermediate Similarity	NPC229787
0.8263	Intermediate Similarity	NPC167479
0.8261	Intermediate Similarity	NPC478213
0.8256	Intermediate Similarity	NPC208797
0.8256	Intermediate Similarity	NPC53680
0.825	Intermediate Similarity	NPC70320
0.825	Intermediate Similarity	NPC474414
0.8246	Intermediate Similarity	NPC477882
0.8246	Intermediate Similarity	NPC477880
0.8242	Intermediate Similarity	NPC22324
0.8242	Intermediate Similarity	NPC108767
0.8239	Intermediate Similarity	NPC316989
0.8235	Intermediate Similarity	NPC66804
0.8228	Intermediate Similarity	NPC252281
0.8228	Intermediate Similarity	NPC477375
0.8228	Intermediate Similarity	NPC327352
0.8228	Intermediate Similarity	NPC198129
0.8225	Intermediate Similarity	NPC471181
0.8225	Intermediate Similarity	NPC178737

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 NPC239113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	948
0.2-0.3	1582
0.3-0.4	2686
0.4-0.5	1898
0.5-0.6	1020
0.6-0.7	487
0.7-0.8	137
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8616	High Similarity	NPD4967	Phase 2
0.8616	High Similarity	NPD4966	Approved
0.8616	High Similarity	NPD4965	Approved
0.8509	High Similarity	NPD6234	Discontinued
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8462	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD37	Approved
0.8387	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD7199	Phase 2
0.8155	Intermediate Similarity	NPD7228	Approved
0.8084	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7240	Approved
0.7904	Intermediate Similarity	NPD5494	Approved
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7747	Intermediate Similarity	NPD4420	Approved
0.7733	Intermediate Similarity	NPD3818	Discontinued
0.7727	Intermediate Similarity	NPD2979	Phase 3
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2438	Suspended
0.7703	Intermediate Similarity	NPD3705	Approved
0.7683	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7458	Discontinued
0.7677	Intermediate Similarity	NPD1933	Approved
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7665	Intermediate Similarity	NPD3817	Phase 2
0.7633	Intermediate Similarity	NPD919	Approved
0.7627	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7003	Approved
0.7605	Intermediate Similarity	NPD7819	Suspended
0.7605	Intermediate Similarity	NPD8455	Phase 2
0.7584	Intermediate Similarity	NPD1281	Approved
0.7581	Intermediate Similarity	NPD5005	Approved
0.7581	Intermediate Similarity	NPD5006	Approved
0.7576	Intermediate Similarity	NPD3226	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD3764	Approved
0.7457	Intermediate Similarity	NPD3926	Phase 2
0.7453	Intermediate Similarity	NPD6674	Discontinued
0.7443	Intermediate Similarity	NPD7074	Phase 3
0.7442	Intermediate Similarity	NPD1247	Approved
0.7442	Intermediate Similarity	NPD6959	Discontinued
0.744	Intermediate Similarity	NPD1934	Approved
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1283	Approved
0.7425	Intermediate Similarity	NPD7028	Phase 2
0.7419	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.7412	Intermediate Similarity	NPD3882	Suspended
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7396	Intermediate Similarity	NPD2801	Approved
0.7386	Intermediate Similarity	NPD7054	Approved
0.7383	Intermediate Similarity	NPD1651	Approved
0.7381	Intermediate Similarity	NPD6385	Approved
0.7381	Intermediate Similarity	NPD6386	Approved
0.7375	Intermediate Similarity	NPD2531	Phase 2
0.7375	Intermediate Similarity	NPD5406	Approved
0.7375	Intermediate Similarity	NPD5405	Approved
0.7375	Intermediate Similarity	NPD5408	Approved
0.7375	Intermediate Similarity	NPD5404	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD5242	Approved
0.7354	Intermediate Similarity	NPD7680	Approved
0.7349	Intermediate Similarity	NPD920	Approved
0.7345	Intermediate Similarity	NPD7472	Approved
0.7341	Intermediate Similarity	NPD8127	Discontinued
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6599	Discontinued
0.7314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6166	Phase 2
0.7301	Intermediate Similarity	NPD3750	Approved
0.7294	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6273	Approved
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7267	Intermediate Similarity	NPD3749	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7233	Intermediate Similarity	NPD447	Suspended
0.7232	Intermediate Similarity	NPD7177	Discontinued
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7808	Phase 3
0.7219	Intermediate Similarity	NPD4626	Approved
0.7207	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6797	Phase 2
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD5710	Approved
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD4307	Phase 2
0.7169	Intermediate Similarity	NPD6799	Approved
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7075	Discontinued
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.716	Intermediate Similarity	NPD2796	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1611	Approved
0.7119	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4380	Phase 2
0.7108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7105	Intermediate Similarity	NPD6776	Approved
0.7105	Intermediate Similarity	NPD6782	Approved
0.7105	Intermediate Similarity	NPD6780	Approved
0.7105	Intermediate Similarity	NPD6781	Approved
0.7105	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD6779	Approved
0.7105	Intermediate Similarity	NPD6778	Approved
0.7102	Intermediate Similarity	NPD3787	Discontinued
0.7098	Intermediate Similarity	NPD7999	Approved
0.7095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4110	Phase 3
0.7091	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6873	Phase 2
0.7072	Intermediate Similarity	NPD7038	Approved
0.7072	Intermediate Similarity	NPD7039	Approved
0.7066	Intermediate Similarity	NPD1511	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7052	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5402	Approved
0.7052	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5353	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7044	Intermediate Similarity	NPD2313	Discontinued
0.7044	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7012	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD1653	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6995	Remote Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD7698	Approved
0.6994	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD17	Approved
0.6988	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1876	Approved
0.6982	Remote Similarity	NPD1512	Approved
0.6982	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5283	Phase 1
0.6973	Remote Similarity	NPD8150	Discontinued
0.6968	Remote Similarity	NPD3972	Approved
0.6964	Remote Similarity	NPD7390	Discontinued
0.6954	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7874	Approved
0.6951	Remote Similarity	NPD4477	Approved
0.6951	Remote Similarity	NPD4476	Approved
0.6951	Remote Similarity	NPD1551	Phase 2
0.6946	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD3267	Approved
0.6943	Remote Similarity	NPD3266	Approved
0.6943	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6004	Phase 3
0.6909	Remote Similarity	NPD6002	Phase 3
0.6909	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6005	Phase 3
0.69	Remote Similarity	NPD7930	Approved
0.6893	Remote Similarity	NPD6746	Phase 2
0.689	Remote Similarity	NPD1510	Phase 2
0.689	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8166	Discontinued
0.6882	Remote Similarity	NPD8434	Phase 2
0.6875	Remote Similarity	NPD3027	Phase 3

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