NPASS Compound

Structure

CID87466 OpenBabel06191715422D 22 24 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 2.2321 0.8660 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 -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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 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 -3.6808 -2.7024 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 -3.5116 -1.0933 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 16 20 1 1 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	5.03
LogD:	4.619
LogS:	-4.69
# Rotatable Bonds:	2
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.148
Fsp3:	0.55
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:	-4.991
MDCK Permeability:	2.754709930741228e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.678

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.625
Plasma Protein Binding (PPB):	96.04244232177734%
Volume Distribution (VD):	2.468
Pgp-substrate:	3.4467973709106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.783
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	15.05
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.695
Skin Sensitization:	0.24
Carcinogencity:	0.836
Eye Corrosion:	0.214
Eye Irritation:	0.29
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC87466

Natural Product ID:	NPC87466
*Common Name:**	Hedychenone
IUPAC Name:	(4S,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-4H-naphthalen-1-one
Synonyms:	Hedychenone
Standard InCHIKey:	MXTCKNHXBBXULO-ZJDHVTHPSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-14-12-17(21)18-19(2,3)9-5-10-20(18,4)16(14)7-6-15-8-11-22-13-15/h6-8,11-13,16,18H,5,9-10H2,1-4H3/b7-6+/t16-,18-,20+/m0/s1
SMILES:	CC1=CC(=O)[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450467
PubChem CID:	12067184
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
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]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17125224]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
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]
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]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[27400231]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
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]
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]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO11192	Hedera helix	Species	Araliaceae	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]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26743	Lippia adoensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24894	Parmelia tinctina	Species	Parmeliaceae	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]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	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]
NPO7465	Vachellia leucophloea	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]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11192	Hedera helix	Species	Araliaceae	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]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	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]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22353	Lucilia caesar	Species	Calliphoridae	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]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26676	Daphne arisanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29093	Homalium longifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26208	Brombya platynema	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26357	Trachyrhamphus serratus	Species	Syngnathidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25732	Trichilia havanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26481	Astragalus kabadianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14283	Ponera metallica	Species	Formicidae	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]
NPO26392	Piptadenia colubrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23410	Potentilla candicans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26524	Chondria californica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25582	Aquilegia viridiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	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]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	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
GI50	4
IC50	5
Others	5

Activity Type	# Activity
Cell Line	13
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	19.41	ug.mL-1	PMID[556313]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	17.68	ug.mL-1	PMID[556313]
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	8.2	ug.mL-1	PMID[556313]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	21.13	ug.mL-1	PMID[556313]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	33.12	ug.mL-1	PMID[556313]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	7400.0	nM	PMID[556314]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	14000.0	nM	PMID[556314]
NPT136	Cell Line	SK-N-SH	Homo sapiens	GI50	=	11600.0	nM	PMID[556314]
NPT136	Cell Line	SK-N-SH	Homo sapiens	LC50	=	17200.0	nM	PMID[556314]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	14900.0	nM	PMID[556314]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	=	19800.0	nM	PMID[556314]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	63200.0	nM	PMID[556314]
NPT165	Cell Line	HeLa	Homo sapiens	LC50	=	81500.0	nM	PMID[556314]
NPT2	Others	Unspecified		Inhibition	=	55.6	%	PMID[556312]

☑ 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 NPC87466 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	305
0.1-0.2	1539
0.2-0.3	3697
0.3-0.4	10165
0.4-0.5	12173
0.5-0.6	11284
0.6-0.7	3159
0.7-0.8	319
0.8-0.85	42
0.85-0.9	6
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC246392
0.9244	High Similarity	NPC290955
0.9189	High Similarity	NPC277525
0.9167	High Similarity	NPC26532
0.9167	High Similarity	NPC279877
0.9091	High Similarity	NPC208389
0.8803	High Similarity	NPC243704
0.878	High Similarity	NPC59502
0.8607	High Similarity	NPC471074
0.8607	High Similarity	NPC473885
0.8583	High Similarity	NPC97566
0.8537	High Similarity	NPC23086
0.8455	Intermediate Similarity	NPC300098
0.8455	Intermediate Similarity	NPC290193
0.8443	Intermediate Similarity	NPC16922
0.84	Intermediate Similarity	NPC477123
0.84	Intermediate Similarity	NPC207294
0.84	Intermediate Similarity	NPC112706
0.84	Intermediate Similarity	NPC477966
0.8397	Intermediate Similarity	NPC474722
0.839	Intermediate Similarity	NPC150895
0.8385	Intermediate Similarity	NPC307401
0.8361	Intermediate Similarity	NPC317217
0.8361	Intermediate Similarity	NPC477967
0.8359	Intermediate Similarity	NPC471006
0.8346	Intermediate Similarity	NPC61788
0.832	Intermediate Similarity	NPC83178
0.8306	Intermediate Similarity	NPC179354
0.8258	Intermediate Similarity	NPC202260
0.8254	Intermediate Similarity	NPC476917
0.8254	Intermediate Similarity	NPC327527
0.8254	Intermediate Similarity	NPC329707
0.8254	Intermediate Similarity	NPC477039
0.8254	Intermediate Similarity	NPC477040
0.824	Intermediate Similarity	NPC46536
0.824	Intermediate Similarity	NPC74612
0.824	Intermediate Similarity	NPC138139
0.8235	Intermediate Similarity	NPC205523
0.8231	Intermediate Similarity	NPC158525
0.8226	Intermediate Similarity	NPC477038
0.8226	Intermediate Similarity	NPC178382
0.8226	Intermediate Similarity	NPC477965
0.8217	Intermediate Similarity	NPC218838
0.8217	Intermediate Similarity	NPC470740
0.8203	Intermediate Similarity	NPC298190
0.8195	Intermediate Similarity	NPC148374
0.8168	Intermediate Similarity	NPC146872
0.814	Intermediate Similarity	NPC473982
0.8125	Intermediate Similarity	NPC476925
0.8099	Intermediate Similarity	NPC312525
0.8099	Intermediate Similarity	NPC217180
0.8099	Intermediate Similarity	NPC212918
0.808	Intermediate Similarity	NPC188377
0.808	Intermediate Similarity	NPC65735
0.808	Intermediate Similarity	NPC118853
0.8077	Intermediate Similarity	NPC293253
0.8074	Intermediate Similarity	NPC263337
0.803	Intermediate Similarity	NPC46896
0.8	Intermediate Similarity	NPC471817
0.797	Intermediate Similarity	NPC310830
0.7967	Intermediate Similarity	NPC473969
0.7967	Intermediate Similarity	NPC137710
0.7955	Intermediate Similarity	NPC92941
0.7955	Intermediate Similarity	NPC476947
0.7934	Intermediate Similarity	NPC28054
0.7926	Intermediate Similarity	NPC56197
0.7923	Intermediate Similarity	NPC89133
0.792	Intermediate Similarity	NPC36255
0.791	Intermediate Similarity	NPC220094
0.791	Intermediate Similarity	NPC476943
0.791	Intermediate Similarity	NPC236532
0.791	Intermediate Similarity	NPC472376
0.7869	Intermediate Similarity	NPC59035
0.7869	Intermediate Similarity	NPC79202
0.7857	Intermediate Similarity	NPC272899
0.7852	Intermediate Similarity	NPC90953
0.7836	Intermediate Similarity	NPC215109
0.7836	Intermediate Similarity	NPC470742
0.7836	Intermediate Similarity	NPC170604
0.7836	Intermediate Similarity	NPC42400
0.782	Intermediate Similarity	NPC209858
0.781	Intermediate Similarity	NPC473152
0.7805	Intermediate Similarity	NPC131801
0.7795	Intermediate Similarity	NPC83115
0.7795	Intermediate Similarity	NPC243269
0.7795	Intermediate Similarity	NPC130275
0.7794	Intermediate Similarity	NPC90296
0.7786	Intermediate Similarity	NPC71821
0.777	Intermediate Similarity	NPC56731
0.777	Intermediate Similarity	NPC290038
0.7734	Intermediate Similarity	NPC230979
0.7734	Intermediate Similarity	NPC303010
0.7727	Intermediate Similarity	NPC471995
0.7724	Intermediate Similarity	NPC45536
0.7721	Intermediate Similarity	NPC233707
0.7714	Intermediate Similarity	NPC233763
0.7698	Intermediate Similarity	NPC199044
0.7698	Intermediate Similarity	NPC142113
0.7698	Intermediate Similarity	NPC238843
0.7687	Intermediate Similarity	NPC324117
0.7686	Intermediate Similarity	NPC22678
0.7681	Intermediate Similarity	NPC52412
0.7664	Intermediate Similarity	NPC67003
0.7664	Intermediate Similarity	NPC473983
0.7664	Intermediate Similarity	NPC201370
0.7661	Intermediate Similarity	NPC227660
0.7661	Intermediate Similarity	NPC208906
0.7661	Intermediate Similarity	NPC144745
0.7652	Intermediate Similarity	NPC477645
0.7647	Intermediate Similarity	NPC177262
0.7643	Intermediate Similarity	NPC245522
0.7643	Intermediate Similarity	NPC114513
0.7643	Intermediate Similarity	NPC185456
0.7639	Intermediate Similarity	NPC246164
0.7634	Intermediate Similarity	NPC198904
0.7626	Intermediate Similarity	NPC243577
0.7626	Intermediate Similarity	NPC267632
0.7622	Intermediate Similarity	NPC212257
0.7622	Intermediate Similarity	NPC228842
0.7615	Intermediate Similarity	NPC95567
0.7615	Intermediate Similarity	NPC319140
0.7609	Intermediate Similarity	NPC205765
0.7606	Intermediate Similarity	NPC93666
0.76	Intermediate Similarity	NPC21831
0.76	Intermediate Similarity	NPC187547
0.76	Intermediate Similarity	NPC206007
0.7594	Intermediate Similarity	NPC279596
0.7589	Intermediate Similarity	NPC470999
0.7589	Intermediate Similarity	NPC471292
0.7589	Intermediate Similarity	NPC478166
0.7586	Intermediate Similarity	NPC471863
0.7554	Intermediate Similarity	NPC121158
0.7554	Intermediate Similarity	NPC475519
0.7552	Intermediate Similarity	NPC95526
0.7538	Intermediate Similarity	NPC470858
0.7535	Intermediate Similarity	NPC302987
0.7535	Intermediate Similarity	NPC224418
0.7535	Intermediate Similarity	NPC471174
0.7535	Intermediate Similarity	NPC281398
0.7535	Intermediate Similarity	NPC10088
0.7534	Intermediate Similarity	NPC25351
0.7518	Intermediate Similarity	NPC34056
0.7517	Intermediate Similarity	NPC121615
0.7517	Intermediate Similarity	NPC294511
0.75	Intermediate Similarity	NPC471521
0.75	Intermediate Similarity	NPC470741
0.75	Intermediate Similarity	NPC472298
0.75	Intermediate Similarity	NPC120836
0.75	Intermediate Similarity	NPC473356
0.75	Intermediate Similarity	NPC476946
0.75	Intermediate Similarity	NPC223415
0.75	Intermediate Similarity	NPC223063
0.7481	Intermediate Similarity	NPC106247
0.7481	Intermediate Similarity	NPC141059
0.748	Intermediate Similarity	NPC246214
0.7479	Intermediate Similarity	NPC42471
0.7465	Intermediate Similarity	NPC62799
0.7465	Intermediate Similarity	NPC276676
0.7465	Intermediate Similarity	NPC262198
0.7465	Intermediate Similarity	NPC346
0.7462	Intermediate Similarity	NPC71274
0.7462	Intermediate Similarity	NPC75557
0.7462	Intermediate Similarity	NPC474829
0.7459	Intermediate Similarity	NPC105249
0.7447	Intermediate Similarity	NPC476944
0.7447	Intermediate Similarity	NPC251865
0.7447	Intermediate Similarity	NPC117674
0.7447	Intermediate Similarity	NPC84479
0.7444	Intermediate Similarity	NPC21460
0.7438	Intermediate Similarity	NPC177331
0.7431	Intermediate Similarity	NPC471001
0.7431	Intermediate Similarity	NPC470998
0.7431	Intermediate Similarity	NPC234494
0.7426	Intermediate Similarity	NPC265793
0.7422	Intermediate Similarity	NPC1848
0.7419	Intermediate Similarity	NPC252004
0.7413	Intermediate Similarity	NPC250228
0.7413	Intermediate Similarity	NPC216755
0.7405	Intermediate Similarity	NPC474260
0.7405	Intermediate Similarity	NPC81912
0.7405	Intermediate Similarity	NPC329922
0.7405	Intermediate Similarity	NPC329694
0.7405	Intermediate Similarity	NPC83301
0.7402	Intermediate Similarity	NPC4898
0.7394	Intermediate Similarity	NPC5676
0.7394	Intermediate Similarity	NPC247221
0.7391	Intermediate Similarity	NPC130976
0.7391	Intermediate Similarity	NPC471996
0.7388	Intermediate Similarity	NPC475092
0.7385	Intermediate Similarity	NPC11799
0.7385	Intermediate Similarity	NPC141252
0.7379	Intermediate Similarity	NPC196846
0.7379	Intermediate Similarity	NPC46551
0.7379	Intermediate Similarity	NPC470997
0.7379	Intermediate Similarity	NPC5180
0.7379	Intermediate Similarity	NPC159927
0.7379	Intermediate Similarity	NPC469335
0.7368	Intermediate Similarity	NPC50583
0.7365	Intermediate Similarity	NPC104736
0.7365	Intermediate Similarity	NPC41880

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 NPC87466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	1073
0.2-0.3	1819
0.3-0.4	3067
0.4-0.5	2019
0.5-0.6	755
0.6-0.7	122
0.7-0.8	4
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
0.748	Intermediate Similarity	NPD1241	Discontinued
0.7464	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3972	Approved
0.7209	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1471	Phase 3
0.7055	Intermediate Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD8032	Phase 2
0.6954	Remote Similarity	NPD5760	Phase 2
0.6954	Remote Similarity	NPD5761	Phase 2
0.6861	Remote Similarity	NPD6832	Phase 2
0.6853	Remote Similarity	NPD2344	Approved
0.6838	Remote Similarity	NPD2798	Approved
0.6831	Remote Similarity	NPD2799	Discontinued
0.6828	Remote Similarity	NPD4628	Phase 3
0.6825	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3142	Approved
0.6786	Remote Similarity	NPD3140	Approved
0.6772	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5585	Approved
0.6742	Remote Similarity	NPD1651	Approved
0.6735	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6765	Approved
0.6728	Remote Similarity	NPD6764	Approved
0.6712	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3869	Phase 3
0.6644	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2797	Approved
0.6642	Remote Similarity	NPD3267	Approved
0.6642	Remote Similarity	NPD3266	Approved
0.664	Remote Similarity	NPD3134	Approved
0.6627	Remote Similarity	NPD8434	Phase 2
0.6621	Remote Similarity	NPD2346	Discontinued
0.6618	Remote Similarity	NPD5327	Phase 3
0.6597	Remote Similarity	NPD3748	Approved
0.6593	Remote Similarity	NPD1281	Approved
0.6567	Remote Similarity	NPD17	Approved
0.6566	Remote Similarity	NPD6785	Approved
0.6566	Remote Similarity	NPD6784	Approved
0.6558	Remote Similarity	NPD6279	Approved
0.6558	Remote Similarity	NPD6280	Approved
0.6549	Remote Similarity	NPD2979	Phase 3
0.6549	Remote Similarity	NPD4307	Phase 2
0.6536	Remote Similarity	NPD6599	Discontinued
0.6531	Remote Similarity	NPD1243	Approved
0.6525	Remote Similarity	NPD3268	Approved
0.6525	Remote Similarity	NPD2313	Discontinued
0.6496	Remote Similarity	NPD4359	Approved
0.6493	Remote Similarity	NPD5691	Approved
0.6486	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1019	Discontinued
0.6471	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7458	Discontinued
0.6454	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1283	Approved
0.6443	Remote Similarity	NPD3887	Approved
0.6434	Remote Similarity	NPD4140	Approved
0.6423	Remote Similarity	NPD9717	Approved
0.6423	Remote Similarity	NPD1608	Approved
0.6406	Remote Similarity	NPD2182	Approved
0.6393	Remote Similarity	NPD3495	Discontinued
0.6389	Remote Similarity	NPD6355	Discontinued
0.6389	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4622	Approved
0.6389	Remote Similarity	NPD4618	Approved
0.6376	Remote Similarity	NPD4110	Phase 3
0.6376	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3750	Approved
0.637	Remote Similarity	NPD4308	Phase 3
0.6357	Remote Similarity	NPD5647	Approved
0.6352	Remote Similarity	NPD919	Approved
0.6333	Remote Similarity	NPD7631	Approved
0.6329	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1358	Approved
0.6327	Remote Similarity	NPD6099	Approved
0.6327	Remote Similarity	NPD4477	Approved
0.6327	Remote Similarity	NPD2531	Phase 2
0.6327	Remote Similarity	NPD4476	Approved
0.6327	Remote Similarity	NPD1551	Phase 2
0.6327	Remote Similarity	NPD2438	Suspended
0.6327	Remote Similarity	NPD6100	Approved
0.6324	Remote Similarity	NPD1778	Approved
0.6324	Remote Similarity	NPD2932	Approved
0.6323	Remote Similarity	NPD7028	Phase 2
0.6316	Remote Similarity	NPD4661	Approved
0.6316	Remote Similarity	NPD7157	Approved
0.6316	Remote Similarity	NPD4662	Approved
0.6312	Remote Similarity	NPD5494	Approved
0.6312	Remote Similarity	NPD9494	Approved
0.6309	Remote Similarity	NPD2800	Approved
0.6306	Remote Similarity	NPD7819	Suspended
0.6301	Remote Similarity	NPD5688	Approved
0.6301	Remote Similarity	NPD5689	Approved
0.6296	Remote Similarity	NPD1894	Discontinued
0.6286	Remote Similarity	NPD1203	Approved
0.6284	Remote Similarity	NPD2353	Approved
0.6284	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2684	Approved
0.6276	Remote Similarity	NPD1933	Approved
0.6273	Remote Similarity	NPD1247	Approved
0.6267	Remote Similarity	NPD8166	Discontinued
0.6258	Remote Similarity	NPD2651	Approved
0.6258	Remote Similarity	NPD2649	Approved
0.6258	Remote Similarity	NPD3226	Approved
0.625	Remote Similarity	NPD4870	Approved
0.625	Remote Similarity	NPD6799	Approved
0.625	Remote Similarity	NPD7609	Phase 3
0.625	Remote Similarity	NPD3025	Approved
0.625	Remote Similarity	NPD3024	Approved
0.6242	Remote Similarity	NPD7577	Discontinued
0.6242	Remote Similarity	NPD1549	Phase 2
0.6242	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6808	Phase 2
0.6234	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1607	Approved
0.6232	Remote Similarity	NPD6287	Discontinued
0.6228	Remote Similarity	NPD6559	Discontinued
0.6225	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5536	Phase 2
0.6222	Remote Similarity	NPD9092	Discovery
0.6216	Remote Similarity	NPD2935	Discontinued
0.6212	Remote Similarity	NPD5535	Approved
0.6209	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1240	Approved
0.6204	Remote Similarity	NPD4626	Approved
0.6204	Remote Similarity	NPD3019	Approved
0.6181	Remote Similarity	NPD6798	Discontinued
0.6181	Remote Similarity	NPD3764	Approved
0.6178	Remote Similarity	NPD7411	Suspended
0.6176	Remote Similarity	NPD9545	Approved
0.6174	Remote Similarity	NPD6005	Phase 3
0.6174	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6004	Phase 3
0.6174	Remote Similarity	NPD6002	Phase 3
0.6173	Remote Similarity	NPD8127	Discontinued
0.6172	Remote Similarity	NPD9697	Approved
0.6164	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5735	Approved
0.6164	Remote Similarity	NPD2296	Approved
0.616	Remote Similarity	NPD1238	Approved
0.6159	Remote Similarity	NPD3023	Approved
0.6159	Remote Similarity	NPD3496	Discontinued
0.6159	Remote Similarity	NPD3026	Approved
0.6159	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4534	Discontinued
0.6133	Remote Similarity	NPD2897	Discontinued
0.6131	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6353	Approved
0.6118	Remote Similarity	NPD2354	Approved
0.6111	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7008	Discontinued
0.6104	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3926	Phase 2
0.6094	Remote Similarity	NPD164	Approved
0.609	Remote Similarity	NPD7843	Approved
0.6087	Remote Similarity	NPD3749	Approved
0.6078	Remote Similarity	NPD7236	Approved
0.6078	Remote Similarity	NPD7440	Discontinued
0.6076	Remote Similarity	NPD5890	Approved
0.6076	Remote Similarity	NPD5889	Approved
0.6076	Remote Similarity	NPD6873	Phase 2
0.6069	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD7294	Phase 1
0.6069	Remote Similarity	NPD411	Approved
0.6069	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD5049	Phase 3
0.6056	Remote Similarity	NPD6362	Approved
0.605	Remote Similarity	NPD650	Approved
0.6042	Remote Similarity	NPD2614	Approved
0.604	Remote Similarity	NPD1510	Phase 2
0.6038	Remote Similarity	NPD6801	Discontinued
0.6034	Remote Similarity	NPD4107	Approved
0.6029	Remote Similarity	NPD9493	Approved
0.6027	Remote Similarity	NPD4062	Phase 3
0.6027	Remote Similarity	NPD6233	Phase 2
0.6027	Remote Similarity	NPD7713	Phase 3
0.6027	Remote Similarity	NPD6663	Approved
0.6026	Remote Similarity	NPD5403	Approved
0.6026	Remote Similarity	NPD2424	Discontinued
0.6026	Remote Similarity	NPD5958	Discontinued
0.6026	Remote Similarity	NPD6980	Clinical (unspecified phase)

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