NPASS Compound

Structure

CID277525 OpenBabel06191716082D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 -2.5981 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5468 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 17 20 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.21
Volume:	327.051
LogP:	5.676
LogD:	4.813
LogS:	-5.019
# Rotatable Bonds:	2
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	4.075
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.477
MDCK Permeability:	1.5150188119150698e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.259
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	93.75404357910156%
Volume Distribution (VD):	1.792
Pgp-substrate:	3.8369762897491455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.81
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.632
CYP2C19-substrate:	0.451
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.277
CYP2D6-inhibitor:	0.68
CYP2D6-substrate:	0.794
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	11.299
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.23
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.066
Carcinogencity:	0.826
Eye Corrosion:	0.268
Eye Irritation:	0.91
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC277525

Natural Product ID:	NPC277525
*Common Name:**	Coronarin E
IUPAC Name:	3-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]furan
Synonyms:	Coranorin E; Coronarin E
Standard InCHIKey:	QXVXYNOIXUIXBI-NDLVVHCESA-N
Standard InCHI:	InChI=1S/C20H28O/c1-15-6-9-18-19(2,3)11-5-12-20(18,4)17(15)8-7-16-10-13-21-14-16/h7-8,10,13-14,17-18H,1,5-6,9,11-12H2,2-4H3/b8-7+/t17-,18-,20+/m0/s1
SMILES:	C=C1CC[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL109252
PubChem CID:	9971144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517742]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25996	Stenolobium stans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23410	Potentilla candicans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25582	Aquilegia viridiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5704	Pecten caurinus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26524	Chondria californica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26743	Lippia adoensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25086	Viburnum betulifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24829	Gyrostroma missouriense	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26554	Hexagonia speciosa	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO26079	Asterococcus muratae	Species	Cerococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23589	Pecten irradians	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24894	Parmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25393	Coelogyne flavida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26175	Spongionella gracilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10372	Kiggelaria africana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22353	Lucilia caesar	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7465	Vachellia leucophloea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6584	Pterodon apparicioi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26846	Guettarda noumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26676	Daphne arisanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11542	Laminaria cloustoni	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26208	Brombya platynema	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29093	Homalium longifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25732	Trichilia havanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26357	Trachyrhamphus serratus	Species	Syngnathidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7302	Glycosmis parva	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14283	Ponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26481	Astragalus kabadianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26392	Piptadenia colubrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24733	Celastrus dispermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15693	Guadua angustifolia	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	7
Others	2

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[490289]
NPT319	Cell Line	B16	Mus musculus	IC50	=	18.8	ug.mL-1	PMID[490289]
NPT788	Cell Line	SNU1	Homo sapiens	IC50	=	8.0	ug.mL-1	PMID[490289]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	33990.0	nM	PMID[490290]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	31210.0	nM	PMID[490290]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	36580.0	nM	PMID[490290]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	53260.0	nM	PMID[490290]
NPT111	Cell Line	K562	Homo sapiens	FC	=	0.7	n.a.	PMID[490291]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	87.2	%	PMID[490291]

☑ 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 NPC277525 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	360
0.1-0.2	1730
0.2-0.3	4065
0.3-0.4	12660
0.4-0.5	10933
0.5-0.6	11563
0.6-0.7	1200
0.7-0.8	163
0.8-0.85	18
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC87466
0.8803	High Similarity	NPC300098
0.8803	High Similarity	NPC290193
0.85	High Similarity	NPC246392
0.85	High Similarity	NPC290955
0.8475	Intermediate Similarity	NPC16922
0.843	Intermediate Similarity	NPC26532
0.843	Intermediate Similarity	NPC279877
0.8421	Intermediate Similarity	NPC150895
0.8361	Intermediate Similarity	NPC208389
0.8333	Intermediate Similarity	NPC179354
0.8264	Intermediate Similarity	NPC138139
0.8264	Intermediate Similarity	NPC46536
0.8264	Intermediate Similarity	NPC74612
0.8211	Intermediate Similarity	NPC59502
0.8205	Intermediate Similarity	NPC243704
0.8182	Intermediate Similarity	NPC473885
0.8182	Intermediate Similarity	NPC471074
0.8151	Intermediate Similarity	NPC97566
0.813	Intermediate Similarity	NPC476917
0.813	Intermediate Similarity	NPC327527
0.813	Intermediate Similarity	NPC477040
0.812	Intermediate Similarity	NPC212918
0.8115	Intermediate Similarity	NPC23086
0.8083	Intermediate Similarity	NPC317217
0.8083	Intermediate Similarity	NPC477967
0.8	Intermediate Similarity	NPC476925
0.7984	Intermediate Similarity	NPC477966
0.7984	Intermediate Similarity	NPC307401
0.7984	Intermediate Similarity	NPC112706
0.7984	Intermediate Similarity	NPC207294
0.7984	Intermediate Similarity	NPC477123
0.7951	Intermediate Similarity	NPC178382
0.7951	Intermediate Similarity	NPC477965
0.7951	Intermediate Similarity	NPC477038
0.7937	Intermediate Similarity	NPC89133
0.7903	Intermediate Similarity	NPC83178
0.7863	Intermediate Similarity	NPC202260
0.784	Intermediate Similarity	NPC477039
0.7795	Intermediate Similarity	NPC61788
0.7787	Intermediate Similarity	NPC36255
0.7734	Intermediate Similarity	NPC473982
0.7727	Intermediate Similarity	NPC474722
0.7724	Intermediate Similarity	NPC272899
0.7698	Intermediate Similarity	NPC329707
0.7692	Intermediate Similarity	NPC476947
0.7687	Intermediate Similarity	NPC475519
0.7687	Intermediate Similarity	NPC263337
0.7686	Intermediate Similarity	NPC137710
0.7674	Intermediate Similarity	NPC471006
0.7674	Intermediate Similarity	NPC218838
0.7661	Intermediate Similarity	NPC83115
0.7661	Intermediate Similarity	NPC130275
0.7661	Intermediate Similarity	NPC188377
0.7661	Intermediate Similarity	NPC118853
0.7661	Intermediate Similarity	NPC65735
0.7661	Intermediate Similarity	NPC243269
0.7656	Intermediate Similarity	NPC298190
0.7647	Intermediate Similarity	NPC205523
0.7634	Intermediate Similarity	NPC46896
0.76	Intermediate Similarity	NPC303010
0.76	Intermediate Similarity	NPC230979
0.7597	Intermediate Similarity	NPC471817
0.7576	Intermediate Similarity	NPC42400
0.7557	Intermediate Similarity	NPC158525
0.7541	Intermediate Similarity	NPC473969
0.7538	Intermediate Similarity	NPC470740
0.7538	Intermediate Similarity	NPC293253
0.7537	Intermediate Similarity	NPC148374
0.7521	Intermediate Similarity	NPC208906
0.7521	Intermediate Similarity	NPC131801
0.7521	Intermediate Similarity	NPC217180
0.7521	Intermediate Similarity	NPC312525
0.7521	Intermediate Similarity	NPC144745
0.7519	Intermediate Similarity	NPC476943
0.75	Intermediate Similarity	NPC471521
0.75	Intermediate Similarity	NPC473356
0.75	Intermediate Similarity	NPC28054
0.75	Intermediate Similarity	NPC146872
0.7458	Intermediate Similarity	NPC105249
0.7444	Intermediate Similarity	NPC215109
0.7444	Intermediate Similarity	NPC310830
0.7444	Intermediate Similarity	NPC170604
0.7438	Intermediate Similarity	NPC59035
0.7438	Intermediate Similarity	NPC79202
0.7436	Intermediate Similarity	NPC177331
0.7424	Intermediate Similarity	NPC324117
0.7424	Intermediate Similarity	NPC92941
0.741	Intermediate Similarity	NPC71821
0.7407	Intermediate Similarity	NPC67003
0.7407	Intermediate Similarity	NPC56197
0.7395	Intermediate Similarity	NPC22678
0.7391	Intermediate Similarity	NPC56731
0.7391	Intermediate Similarity	NPC290038
0.7388	Intermediate Similarity	NPC472376
0.7364	Intermediate Similarity	NPC223063
0.7364	Intermediate Similarity	NPC120836
0.7364	Intermediate Similarity	NPC198904
0.7353	Intermediate Similarity	NPC205765
0.7339	Intermediate Similarity	NPC246214
0.7338	Intermediate Similarity	NPC233763
0.7333	Intermediate Similarity	NPC90953
0.7333	Intermediate Similarity	NPC233707
0.7317	Intermediate Similarity	NPC206007
0.7317	Intermediate Similarity	NPC187547
0.7317	Intermediate Similarity	NPC21831
0.7313	Intermediate Similarity	NPC470742
0.7299	Intermediate Similarity	NPC52412
0.7299	Intermediate Similarity	NPC121158
0.7295	Intermediate Similarity	NPC45536
0.7293	Intermediate Similarity	NPC209858
0.7279	Intermediate Similarity	NPC473983
0.7279	Intermediate Similarity	NPC201370
0.7259	Intermediate Similarity	NPC236532
0.7259	Intermediate Similarity	NPC220094
0.7258	Intermediate Similarity	NPC4898
0.7254	Intermediate Similarity	NPC212257
0.7254	Intermediate Similarity	NPC228842
0.7252	Intermediate Similarity	NPC477645
0.725	Intermediate Similarity	NPC26157
0.725	Intermediate Similarity	NPC1811
0.7246	Intermediate Similarity	NPC476946
0.7246	Intermediate Similarity	NPC267632
0.7246	Intermediate Similarity	NPC243577
0.7236	Intermediate Similarity	NPC227660
0.7234	Intermediate Similarity	NPC93666
0.7226	Intermediate Similarity	NPC20500
0.7222	Intermediate Similarity	NPC471549
0.7222	Intermediate Similarity	NPC289911
0.7222	Intermediate Similarity	NPC283284
0.7222	Intermediate Similarity	NPC473379
0.7214	Intermediate Similarity	NPC478166
0.7209	Intermediate Similarity	NPC95567
0.7209	Intermediate Similarity	NPC319140
0.7197	Intermediate Similarity	NPC471995
0.7194	Intermediate Similarity	NPC251865
0.7194	Intermediate Similarity	NPC199044
0.7194	Intermediate Similarity	NPC476944
0.7194	Intermediate Similarity	NPC142113
0.7194	Intermediate Similarity	NPC238843
0.7188	Intermediate Similarity	NPC71274
0.7188	Intermediate Similarity	NPC474829
0.7188	Intermediate Similarity	NPC75557
0.7183	Intermediate Similarity	NPC95526
0.7179	Intermediate Similarity	NPC42471
0.7174	Intermediate Similarity	NPC473152
0.7165	Intermediate Similarity	NPC475818
0.7163	Intermediate Similarity	NPC281398
0.7154	Intermediate Similarity	NPC316062
0.7153	Intermediate Similarity	NPC121615
0.7153	Intermediate Similarity	NPC294511
0.7153	Intermediate Similarity	NPC246164
0.7153	Intermediate Similarity	NPC90296
0.7143	Intermediate Similarity	NPC245522
0.7143	Intermediate Similarity	NPC115859
0.7143	Intermediate Similarity	NPC185456
0.7143	Intermediate Similarity	NPC5676
0.7143	Intermediate Similarity	NPC114513
0.7143	Intermediate Similarity	NPC1848
0.7143	Intermediate Similarity	NPC474136
0.7133	Intermediate Similarity	NPC472298
0.7132	Intermediate Similarity	NPC329694
0.7132	Intermediate Similarity	NPC83301
0.7132	Intermediate Similarity	NPC81912
0.7132	Intermediate Similarity	NPC329922
0.7132	Intermediate Similarity	NPC470858
0.7132	Intermediate Similarity	NPC177262
0.7132	Intermediate Similarity	NPC474260
0.7131	Intermediate Similarity	NPC252004
0.7122	Intermediate Similarity	NPC223415
0.7119	Intermediate Similarity	NPC140688
0.7103	Intermediate Similarity	NPC471863
0.7092	Intermediate Similarity	NPC471292
0.7092	Intermediate Similarity	NPC262198
0.7092	Intermediate Similarity	NPC62799
0.7092	Intermediate Similarity	NPC470999
0.709	Intermediate Similarity	NPC471998
0.709	Intermediate Similarity	NPC106247
0.7087	Intermediate Similarity	NPC263870
0.7077	Intermediate Similarity	NPC474830
0.7077	Intermediate Similarity	NPC141059
0.7055	Intermediate Similarity	NPC25351
0.7043	Intermediate Similarity	NPC156768
0.7042	Intermediate Similarity	NPC255414
0.7042	Intermediate Similarity	NPC224418
0.7042	Intermediate Similarity	NPC302987
0.7042	Intermediate Similarity	NPC216755
0.7042	Intermediate Similarity	NPC221809
0.7042	Intermediate Similarity	NPC471174
0.7031	Intermediate Similarity	NPC476351
0.7029	Intermediate Similarity	NPC156077
0.7023	Intermediate Similarity	NPC474279
0.7023	Intermediate Similarity	NPC474438
0.7007	Intermediate Similarity	NPC41880
0.7007	Intermediate Similarity	NPC104736
0.7	Intermediate Similarity	NPC470741
0.6993	Remote Similarity	NPC471007
0.6993	Remote Similarity	NPC19747
0.6992	Remote Similarity	NPC475092
0.6991	Remote Similarity	NPC146316

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 NPC277525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	1053
0.2-0.3	1883
0.3-0.4	3285
0.4-0.5	1891
0.5-0.6	657
0.6-0.7	44
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7206	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6911	Remote Similarity	NPD1241	Discontinued
0.687	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5585	Approved
0.6822	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6273	Approved
0.6779	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3134	Approved
0.6718	Remote Similarity	NPD5327	Phase 3
0.6716	Remote Similarity	NPD6832	Phase 2
0.6714	Remote Similarity	NPD1471	Phase 3
0.6711	Remote Similarity	NPD5760	Phase 2
0.6711	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2344	Approved
0.6591	Remote Similarity	NPD4359	Approved
0.6573	Remote Similarity	NPD4628	Phase 3
0.6571	Remote Similarity	NPD2799	Discontinued
0.6569	Remote Similarity	NPD8032	Phase 2
0.6567	Remote Similarity	NPD2798	Approved
0.6532	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4140	Approved
0.6493	Remote Similarity	NPD2797	Approved
0.6462	Remote Similarity	NPD5691	Approved
0.6458	Remote Similarity	NPD7003	Approved
0.6429	Remote Similarity	NPD5535	Approved
0.6423	Remote Similarity	NPD1358	Approved
0.6414	Remote Similarity	NPD2309	Approved
0.6412	Remote Similarity	NPD17	Approved
0.6408	Remote Similarity	NPD2796	Approved
0.6406	Remote Similarity	NPD7157	Approved
0.6403	Remote Similarity	NPD3140	Approved
0.6403	Remote Similarity	NPD3142	Approved
0.6389	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD2684	Approved
0.637	Remote Similarity	NPD3266	Approved
0.637	Remote Similarity	NPD643	Clinical (unspecified phase)
0.637	Remote Similarity	NPD3267	Approved
0.6336	Remote Similarity	NPD3444	Approved
0.6336	Remote Similarity	NPD1651	Approved
0.6336	Remote Similarity	NPD3443	Approved
0.6336	Remote Similarity	NPD3445	Approved
0.6331	Remote Similarity	NPD4870	Approved
0.6316	Remote Similarity	NPD1281	Approved
0.6316	Remote Similarity	NPD6280	Approved
0.6316	Remote Similarity	NPD6279	Approved
0.6309	Remote Similarity	NPD3873	Phase 3
0.6309	Remote Similarity	NPD3869	Phase 3
0.6309	Remote Similarity	NPD920	Approved
0.6308	Remote Similarity	NPD5536	Phase 2
0.6296	Remote Similarity	NPD6765	Approved
0.6296	Remote Similarity	NPD6764	Approved
0.6286	Remote Similarity	NPD2979	Phase 3
0.6286	Remote Similarity	NPD4307	Phase 2
0.6284	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2557	Approved
0.6269	Remote Similarity	NPD1608	Approved
0.626	Remote Similarity	NPD9697	Approved
0.6259	Remote Similarity	NPD3268	Approved
0.6259	Remote Similarity	NPD2313	Discontinued
0.625	Remote Similarity	NPD2346	Discontinued
0.6241	Remote Similarity	NPD3496	Discontinued
0.6241	Remote Similarity	NPD6355	Discontinued
0.6241	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5735	Approved
0.6241	Remote Similarity	NPD4618	Approved
0.6241	Remote Similarity	NPD4622	Approved
0.624	Remote Similarity	NPD2182	Approved
0.6231	Remote Similarity	NPD3596	Phase 2
0.6225	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3748	Approved
0.6205	Remote Similarity	NPD8434	Phase 2
0.6204	Remote Similarity	NPD1019	Discontinued
0.6197	Remote Similarity	NPD6353	Approved
0.619	Remote Similarity	NPD3887	Approved
0.6187	Remote Similarity	NPD7095	Approved
0.6187	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD6599	Discontinued
0.6181	Remote Similarity	NPD4477	Approved
0.6181	Remote Similarity	NPD4476	Approved
0.6176	Remote Similarity	NPD1283	Approved
0.6172	Remote Similarity	NPD7843	Approved
0.617	Remote Similarity	NPD4060	Phase 1
0.6165	Remote Similarity	NPD1778	Approved
0.6165	Remote Similarity	NPD4626	Approved
0.6164	Remote Similarity	NPD1243	Approved
0.6154	Remote Similarity	NPD5688	Approved
0.6154	Remote Similarity	NPD5689	Approved
0.6148	Remote Similarity	NPD9717	Approved
0.6145	Remote Similarity	NPD6785	Approved
0.6145	Remote Similarity	NPD6784	Approved
0.6143	Remote Similarity	NPD7294	Phase 1
0.6136	Remote Similarity	NPD1894	Discontinued
0.6136	Remote Similarity	NPD6581	Approved
0.6136	Remote Similarity	NPD6580	Approved
0.6131	Remote Similarity	NPD1203	Approved
0.6127	Remote Similarity	NPD1933	Approved
0.6124	Remote Similarity	NPD5283	Phase 1
0.6122	Remote Similarity	NPD4110	Phase 3
0.6122	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD7458	Discontinued
0.6116	Remote Similarity	NPD1238	Approved
0.6115	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4308	Phase 3
0.6094	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.609	Remote Similarity	NPD3049	Approved
0.6087	Remote Similarity	NPD4624	Approved
0.608	Remote Similarity	NPD968	Approved
0.6076	Remote Similarity	NPD5494	Approved
0.6074	Remote Similarity	NPD1611	Approved
0.6069	Remote Similarity	NPD2438	Suspended
0.6069	Remote Similarity	NPD2935	Discontinued
0.6069	Remote Similarity	NPD1551	Phase 2
0.6069	Remote Similarity	NPD2531	Phase 2
0.6067	Remote Similarity	NPD4661	Approved
0.6067	Remote Similarity	NPD4662	Approved
0.6065	Remote Similarity	NPD7819	Suspended
0.6063	Remote Similarity	NPD5451	Approved
0.6043	Remote Similarity	NPD9494	Approved
0.6042	Remote Similarity	NPD7097	Phase 1
0.6028	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD6798	Discontinued
0.6028	Remote Similarity	NPD3764	Approved
0.6027	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD2353	Approved
0.6027	Remote Similarity	NPD5763	Approved
0.6027	Remote Similarity	NPD5762	Approved
0.6014	Remote Similarity	NPD4098	Discontinued
0.6014	Remote Similarity	NPD6362	Approved
0.6014	Remote Similarity	NPD3750	Approved
0.6014	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2649	Approved
0.6013	Remote Similarity	NPD919	Approved
0.6013	Remote Similarity	NPD2651	Approved
0.6	Remote Similarity	NPD6808	Phase 2
0.6	Remote Similarity	NPD7577	Discontinued
0.6	Remote Similarity	NPD6799	Approved
0.6	Remote Similarity	NPD3847	Discontinued
0.5987	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD1549	Phase 2
0.5986	Remote Similarity	NPD4534	Discontinued
0.5986	Remote Similarity	NPD2897	Discontinued
0.5986	Remote Similarity	NPD2424	Discontinued
0.5986	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5647	Approved
0.5971	Remote Similarity	NPD7018	Phase 2
0.596	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD6100	Approved
0.5959	Remote Similarity	NPD6099	Approved
0.5951	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD1240	Approved
0.5942	Remote Similarity	NPD6696	Suspended
0.5942	Remote Similarity	NPD8651	Approved
0.594	Remote Similarity	NPD9092	Discovery
0.5938	Remote Similarity	NPD8127	Discontinued
0.5938	Remote Similarity	NPD1247	Approved
0.5935	Remote Similarity	NPD7411	Suspended
0.5935	Remote Similarity	NPD6873	Phase 2
0.5933	Remote Similarity	NPD7440	Discontinued
0.5929	Remote Similarity	NPD1712	Approved
0.5929	Remote Similarity	NPD5736	Approved
0.5929	Remote Similarity	NPD2861	Phase 2
0.5926	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2556	Approved
0.5926	Remote Similarity	NPD5846	Approved
0.5926	Remote Similarity	NPD6516	Phase 2
0.5926	Remote Similarity	NPD2554	Approved
0.5924	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD2296	Approved
0.5923	Remote Similarity	NPD821	Approved
0.592	Remote Similarity	NPD164	Approved
0.5918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6004	Phase 3
0.5918	Remote Similarity	NPD6002	Phase 3
0.5918	Remote Similarity	NPD6005	Phase 3
0.5918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD1840	Phase 2
0.5909	Remote Similarity	NPD3226	Approved
0.5909	Remote Similarity	NPD6671	Approved
0.5909	Remote Similarity	NPD6387	Discontinued
0.5906	Remote Similarity	NPD290	Approved
0.5904	Remote Similarity	NPD6559	Discontinued
0.5896	Remote Similarity	NPD9545	Approved
0.589	Remote Similarity	NPD7033	Discontinued
0.5887	Remote Similarity	NPD4908	Phase 1
0.5886	Remote Similarity	NPD7768	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