NPASS Compound

Structure

CID221992 OpenBabel06191716012D 23 26 0 0 0 0 0 0 0 0999 V2000 5.0284 -2.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8968 -2.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8654 -0.4823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0276 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3523 -1.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8657 -1.4501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8361 2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1901 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5136 -0.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -1.4506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3517 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5131 1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3515 0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0282 -1.9343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3521 3.2554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5128 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2173 1.4685 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	319.66
LogP:	3.971
LogD:	2.931
LogS:	-5.512
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.819
Synthetic Accessibility Score:	3.062
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	1.926756158354692e-05
Pgp-inhibitor:	0.672
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.32

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	98.39452362060547%
Volume Distribution (VD):	1.974
Pgp-substrate:	1.6073623895645142%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.383
CYP2C19-inhibitor:	0.39
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.387
CYP2D6-inhibitor:	0.496
CYP2D6-substrate:	0.522
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	3.483
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.552
Skin Sensitization:	0.364
Carcinogencity:	0.867
Eye Corrosion:	0.003
Eye Irritation:	0.331
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC221992

Natural Product ID:	NPC221992
*Common Name:**	Przewaquinone A
IUPAC Name:	1-(hydroxymethyl)-6,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:
Standard InCHIKey:	CEHVTERMWMYLCP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-19(2)7-3-4-11-13(19)6-5-12-15(11)17(22)16(21)14-10(8-20)9-23-18(12)14/h5-6,9,20H,3-4,7-8H2,1-2H3
SMILES:	CC1(C)CCCc2c1ccc1-c3c(c(CO)co3)C(=O)C(=O)c21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL578036
PubChem CID:	619402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880325]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Himeji City, Japan	n.a.	PMID[15053555]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1567426]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764147]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO25813.1	Salvia przewalskii var. mandarinorum	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813.1	Salvia przewalskii var. mandarinorum	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	0tholaena dealbata	Species	Pteridaceae	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	1
Others	1

Activity Type	# Activity
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3912	Tissue	Artery	Sus scrofa	ED50	=	-7.4	ug ml-1	PMID[473279]
NPT3912	Tissue	Artery	Sus scrofa	Emax	=	29.2	%	PMID[473279]

☑ 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 NPC221992 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	363
0.1-0.2	1547
0.2-0.3	3297
0.3-0.4	8660
0.4-0.5	10876
0.5-0.6	5359
0.6-0.7	6801
0.7-0.8	5623
0.8-0.85	140
0.85-0.9	17
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC145830
0.96	High Similarity	NPC179170
0.9392	High Similarity	NPC281398
0.9342	High Similarity	NPC88958
0.9286	High Similarity	NPC10051
0.9286	High Similarity	NPC299094
0.9272	High Similarity	NPC144010
0.9128	High Similarity	NPC93241
0.9128	High Similarity	NPC27798
0.906	High Similarity	NPC117674
0.8938	High Similarity	NPC472784
0.8766	High Similarity	NPC192069
0.8726	High Similarity	NPC290927
0.8712	High Similarity	NPC44602
0.8688	High Similarity	NPC472782
0.8688	High Similarity	NPC472781
0.8684	High Similarity	NPC163948
0.8662	High Similarity	NPC24232
0.8634	High Similarity	NPC472783
0.8634	High Similarity	NPC472780
0.8634	High Similarity	NPC24761
0.8623	High Similarity	NPC295914
0.8608	High Similarity	NPC42458
0.8608	High Similarity	NPC158261
0.8589	High Similarity	NPC136641
0.8571	High Similarity	NPC233763
0.8562	High Similarity	NPC140952
0.8544	High Similarity	NPC44606
0.8543	High Similarity	NPC18904
0.8528	High Similarity	NPC100849
0.8509	High Similarity	NPC476350
0.8509	High Similarity	NPC476349
0.8509	High Similarity	NPC472299
0.8506	High Similarity	NPC114513
0.8506	High Similarity	NPC245522
0.85	High Similarity	NPC81405
0.85	High Similarity	NPC160015
0.85	High Similarity	NPC247677
0.8491	Intermediate Similarity	NPC23559
0.8485	Intermediate Similarity	NPC473945
0.8471	Intermediate Similarity	NPC472298
0.8462	Intermediate Similarity	NPC478018
0.8462	Intermediate Similarity	NPC252208
0.8452	Intermediate Similarity	NPC478166
0.8452	Intermediate Similarity	NPC478019
0.8447	Intermediate Similarity	NPC164110
0.8447	Intermediate Similarity	NPC212967
0.8447	Intermediate Similarity	NPC296957
0.8447	Intermediate Similarity	NPC96342
0.8447	Intermediate Similarity	NPC246647
0.8447	Intermediate Similarity	NPC260902
0.8428	Intermediate Similarity	NPC263676
0.8405	Intermediate Similarity	NPC269117
0.8397	Intermediate Similarity	NPC300540
0.8395	Intermediate Similarity	NPC472877
0.8385	Intermediate Similarity	NPC180924
0.8375	Intermediate Similarity	NPC469966
0.8375	Intermediate Similarity	NPC208806
0.8365	Intermediate Similarity	NPC471613
0.8354	Intermediate Similarity	NPC56358
0.8333	Intermediate Similarity	NPC474611
0.8333	Intermediate Similarity	NPC67197
0.8333	Intermediate Similarity	NPC317900
0.8333	Intermediate Similarity	NPC123153
0.8333	Intermediate Similarity	NPC294300
0.8333	Intermediate Similarity	NPC476404
0.8323	Intermediate Similarity	NPC53016
0.8323	Intermediate Similarity	NPC148938
0.8323	Intermediate Similarity	NPC158871
0.8323	Intermediate Similarity	NPC3898
0.8313	Intermediate Similarity	NPC40356
0.8313	Intermediate Similarity	NPC282793
0.8313	Intermediate Similarity	NPC67654
0.8313	Intermediate Similarity	NPC154683
0.8313	Intermediate Similarity	NPC191012
0.8313	Intermediate Similarity	NPC255787
0.8303	Intermediate Similarity	NPC121995
0.8302	Intermediate Similarity	NPC472787
0.8291	Intermediate Similarity	NPC95526
0.8282	Intermediate Similarity	NPC287559
0.8272	Intermediate Similarity	NPC304692
0.8263	Intermediate Similarity	NPC472660
0.8261	Intermediate Similarity	NPC75310
0.8261	Intermediate Similarity	NPC1477
0.8261	Intermediate Similarity	NPC235333
0.8261	Intermediate Similarity	NPC213608
0.8258	Intermediate Similarity	NPC64568
0.8258	Intermediate Similarity	NPC69755
0.8253	Intermediate Similarity	NPC270312
0.825	Intermediate Similarity	NPC116604
0.825	Intermediate Similarity	NPC156244
0.8242	Intermediate Similarity	NPC193998
0.8242	Intermediate Similarity	NPC472664
0.8239	Intermediate Similarity	NPC226578
0.8235	Intermediate Similarity	NPC265181
0.8232	Intermediate Similarity	NPC18986
0.8221	Intermediate Similarity	NPC217602
0.8221	Intermediate Similarity	NPC268360
0.8221	Intermediate Similarity	NPC104380
0.8221	Intermediate Similarity	NPC473282
0.821	Intermediate Similarity	NPC41880
0.821	Intermediate Similarity	NPC104736
0.821	Intermediate Similarity	NPC297531
0.821	Intermediate Similarity	NPC213936
0.8208	Intermediate Similarity	NPC228209
0.8205	Intermediate Similarity	NPC476944
0.8204	Intermediate Similarity	NPC296558
0.8199	Intermediate Similarity	NPC5871
0.8199	Intermediate Similarity	NPC130015
0.8199	Intermediate Similarity	NPC38361
0.8199	Intermediate Similarity	NPC10429
0.8199	Intermediate Similarity	NPC114880
0.8199	Intermediate Similarity	NPC253872
0.8199	Intermediate Similarity	NPC207624
0.8194	Intermediate Similarity	NPC149780
0.8194	Intermediate Similarity	NPC263337
0.8193	Intermediate Similarity	NPC308156
0.8187	Intermediate Similarity	NPC472406
0.8187	Intermediate Similarity	NPC255641
0.8187	Intermediate Similarity	NPC135303
0.8187	Intermediate Similarity	NPC147735
0.8187	Intermediate Similarity	NPC472661
0.8187	Intermediate Similarity	NPC148423
0.8187	Intermediate Similarity	NPC290954
0.8182	Intermediate Similarity	NPC304387
0.8176	Intermediate Similarity	NPC280025
0.8176	Intermediate Similarity	NPC211625
0.8171	Intermediate Similarity	NPC324736
0.817	Intermediate Similarity	NPC177262
0.8165	Intermediate Similarity	NPC211565
0.8165	Intermediate Similarity	NPC224418
0.8165	Intermediate Similarity	NPC60389
0.8161	Intermediate Similarity	NPC472662
0.8161	Intermediate Similarity	NPC472663
0.816	Intermediate Similarity	NPC474360
0.8153	Intermediate Similarity	NPC290038
0.8153	Intermediate Similarity	NPC469385
0.8148	Intermediate Similarity	NPC472786
0.8148	Intermediate Similarity	NPC122365
0.8148	Intermediate Similarity	NPC472785
0.8148	Intermediate Similarity	NPC214632
0.8144	Intermediate Similarity	NPC314653
0.8144	Intermediate Similarity	NPC316262
0.8141	Intermediate Similarity	NPC267632
0.8141	Intermediate Similarity	NPC329493
0.8137	Intermediate Similarity	NPC193976
0.8137	Intermediate Similarity	NPC475777
0.8137	Intermediate Similarity	NPC58668
0.8137	Intermediate Similarity	NPC115324
0.8137	Intermediate Similarity	NPC474417
0.8137	Intermediate Similarity	NPC106372
0.8137	Intermediate Similarity	NPC170169
0.8137	Intermediate Similarity	NPC149526
0.8137	Intermediate Similarity	NPC470569
0.8137	Intermediate Similarity	NPC23668
0.8125	Intermediate Similarity	NPC37226
0.8125	Intermediate Similarity	NPC226644
0.8125	Intermediate Similarity	NPC39929
0.8125	Intermediate Similarity	NPC296030
0.8121	Intermediate Similarity	NPC470810
0.8121	Intermediate Similarity	NPC115432
0.8121	Intermediate Similarity	NPC313368
0.8121	Intermediate Similarity	NPC260296
0.8117	Intermediate Similarity	NPC233707
0.8117	Intermediate Similarity	NPC202260
0.8113	Intermediate Similarity	NPC198427
0.8113	Intermediate Similarity	NPC71055
0.8113	Intermediate Similarity	NPC150215
0.811	Intermediate Similarity	NPC65504
0.811	Intermediate Similarity	NPC272196
0.811	Intermediate Similarity	NPC44199
0.811	Intermediate Similarity	NPC269495
0.811	Intermediate Similarity	NPC270044
0.8103	Intermediate Similarity	NPC8927
0.8101	Intermediate Similarity	NPC62799
0.8101	Intermediate Similarity	NPC97904
0.8098	Intermediate Similarity	NPC198490
0.8098	Intermediate Similarity	NPC233776
0.8098	Intermediate Similarity	NPC478159
0.8098	Intermediate Similarity	NPC478161
0.8098	Intermediate Similarity	NPC99199
0.8095	Intermediate Similarity	NPC291742
0.8092	Intermediate Similarity	NPC104682
0.8089	Intermediate Similarity	NPC66593
0.8086	Intermediate Similarity	NPC178932
0.8086	Intermediate Similarity	NPC142308
0.8086	Intermediate Similarity	NPC164912
0.8084	Intermediate Similarity	NPC101769
0.8084	Intermediate Similarity	NPC38591
0.8077	Intermediate Similarity	NPC52412
0.8077	Intermediate Similarity	NPC124365
0.8075	Intermediate Similarity	NPC321896
0.8075	Intermediate Similarity	NPC476185
0.8075	Intermediate Similarity	NPC230713
0.8075	Intermediate Similarity	NPC78335
0.8075	Intermediate Similarity	NPC13282
0.8075	Intermediate Similarity	NPC202595
0.8075	Intermediate Similarity	NPC167576
0.8075	Intermediate Similarity	NPC470568
0.8072	Intermediate Similarity	NPC283209

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 NPC221992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	971
0.2-0.3	1453
0.3-0.4	2628
0.4-0.5	2214
0.5-0.6	1086
0.6-0.7	362
0.7-0.8	102
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD3226	Approved
0.8235	Intermediate Similarity	NPD1471	Phase 3
0.8117	Intermediate Similarity	NPD2344	Approved
0.8117	Intermediate Similarity	NPD2346	Discontinued
0.8117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5761	Phase 2
0.7927	Intermediate Similarity	NPD5760	Phase 2
0.7911	Intermediate Similarity	NPD2309	Approved
0.7841	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7751	Intermediate Similarity	NPD6959	Discontinued
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7711	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7679	Intermediate Similarity	NPD3749	Approved
0.7673	Intermediate Similarity	NPD2800	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD920	Approved
0.7665	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7633	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6232	Discontinued
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7546	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1247	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7529	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7003	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7456	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4380	Phase 2
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3972	Approved
0.7399	Intermediate Similarity	NPD6808	Phase 2
0.7391	Intermediate Similarity	NPD1549	Phase 2
0.7384	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD2796	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD2296	Approved
0.7337	Intermediate Similarity	NPD6279	Approved
0.7337	Intermediate Similarity	NPD6280	Approved
0.7329	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD3882	Suspended
0.731	Intermediate Similarity	NPD7768	Phase 2
0.7308	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1607	Approved
0.7294	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7239	Intermediate Similarity	NPD1243	Approved
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1934	Approved
0.7235	Intermediate Similarity	NPD6801	Discontinued
0.7232	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD2798	Approved
0.7225	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.7193	Intermediate Similarity	NPD2801	Approved
0.717	Intermediate Similarity	NPD1240	Approved
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6765	Approved
0.7167	Intermediate Similarity	NPD6764	Approved
0.7161	Intermediate Similarity	NPD1203	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6166	Phase 2
0.7119	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7097	Intermediate Similarity	NPD1876	Approved
0.7091	Intermediate Similarity	NPD3750	Approved
0.7078	Intermediate Similarity	NPD9717	Approved
0.7076	Intermediate Similarity	NPD5890	Approved
0.7076	Intermediate Similarity	NPD5889	Approved
0.7066	Intermediate Similarity	NPD1511	Approved
0.7066	Intermediate Similarity	NPD6799	Approved
0.7052	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7044	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD1651	Approved
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7033	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD447	Suspended
0.7016	Intermediate Similarity	NPD6778	Approved
0.7016	Intermediate Similarity	NPD6781	Approved
0.7016	Intermediate Similarity	NPD6782	Approved
0.7016	Intermediate Similarity	NPD6780	Approved
0.7016	Intermediate Similarity	NPD6776	Approved
0.7016	Intermediate Similarity	NPD6777	Approved
0.7016	Intermediate Similarity	NPD6779	Approved
0.7013	Intermediate Similarity	NPD1201	Approved
0.7011	Intermediate Similarity	NPD6784	Approved
0.7011	Intermediate Similarity	NPD6785	Approved
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7033	Discontinued
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1283	Approved
0.6982	Remote Similarity	NPD1512	Approved
0.6981	Remote Similarity	NPD7008	Discontinued
0.6975	Remote Similarity	NPD6651	Approved
0.6973	Remote Similarity	NPD8150	Discontinued
0.697	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8285	Discontinued
0.6957	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD4307	Phase 2
0.6954	Remote Similarity	NPD3817	Phase 2
0.6941	Remote Similarity	NPD5403	Approved
0.6937	Remote Similarity	NPD3764	Approved
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5953	Discontinued
0.6919	Remote Similarity	NPD6585	Discontinued
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7435	Discontinued
0.6907	Remote Similarity	NPD7697	Approved
0.6907	Remote Similarity	NPD7696	Phase 3
0.6907	Remote Similarity	NPD7698	Approved
0.6905	Remote Similarity	NPD7236	Approved
0.6898	Remote Similarity	NPD4287	Approved
0.6894	Remote Similarity	NPD8032	Phase 2
0.689	Remote Similarity	NPD3748	Approved
0.6878	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6213	Phase 3
0.6878	Remote Similarity	NPD6212	Phase 3
0.6875	Remote Similarity	NPD4625	Phase 3
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD7870	Phase 2
0.6868	Remote Similarity	NPD7074	Phase 3
0.6852	Remote Similarity	NPD4140	Approved
0.6842	Remote Similarity	NPD6534	Approved
0.6842	Remote Similarity	NPD6535	Approved
0.6839	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5401	Approved
0.6821	Remote Similarity	NPD5951	Approved
0.6818	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD4965	Approved
0.6818	Remote Similarity	NPD4967	Phase 2
0.6816	Remote Similarity	NPD3787	Discontinued
0.6813	Remote Similarity	NPD7286	Phase 2
0.6813	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD1933	Approved
0.6807	Remote Similarity	NPD6004	Phase 3
0.6807	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6005	Phase 3
0.6807	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6002	Phase 3
0.6802	Remote Similarity	NPD7239	Suspended
0.6795	Remote Similarity	NPD1281	Approved
0.6792	Remote Similarity	NPD1019	Discontinued
0.6776	Remote Similarity	NPD7472	Approved
0.6768	Remote Similarity	NPD7701	Phase 2
0.6766	Remote Similarity	NPD2424	Discontinued
0.676	Remote Similarity	NPD8127	Discontinued
0.6752	Remote Similarity	NPD1608	Approved
0.6749	Remote Similarity	NPD8404	Phase 2
0.6747	Remote Similarity	NPD4476	Approved
0.6747	Remote Similarity	NPD4477	Approved
0.6747	Remote Similarity	NPD2438	Suspended
0.6746	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6797	Phase 2
0.6736	Remote Similarity	NPD7699	Phase 2

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