NPASS Compound

Structure

CID300098 OpenBabel06191716102D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 0.8660 -1.5000 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 0.0000 2.0000 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 4.1808 -1.8364 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 -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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -0.8660 1.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 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 17 1 0 0 0 0 12 18 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 14 17 1 0 0 0 0 16 20 1 1 0 0 0 17 21 1 1 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:	300.21
Volume:	335.841
LogP:	4.302
LogD:	4.222
LogS:	-4.585
# Rotatable Bonds:	2
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	4.42
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:	-4.616
MDCK Permeability:	2.312965261808131e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.212
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	92.76151275634766%
Volume Distribution (VD):	1.428
Pgp-substrate:	12.667109489440918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.791
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.708
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	11.74
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.375
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.053
Carcinogencity:	0.589
Eye Corrosion:	0.493
Eye Irritation:	0.561
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC300098

Natural Product ID:	NPC300098
*Common Name:**	Coronarin A
IUPAC Name:	(2S,4R,4aS,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-4a,8,8-trimethyl-3-methylidene-2,4,5,6,7,8a-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	RHCBUXSXDFNUAG-UDMCIFMYSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-14-16(7-6-15-8-11-22-13-15)20(4)10-5-9-19(2,3)18(20)12-17(14)21/h6-8,11,13,16-18,21H,1,5,9-10,12H2,2-4H3/b7-6+/t16-,17-,18-,20+/m0/s1
SMILES:	C=C1[C@@H](O)C[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL64407
PubChem CID:	24851535
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]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
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]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944995]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26231157]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30169038]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
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]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	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]
NPO18947	Ervatamia dichotoma	n.a.	n.a.	n.a.	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]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18947	Ervatamia dichotoma	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	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]
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]
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]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25469	Lupinus luteus	Species	Fabaceae	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]
NPO24733	Celastrus dispermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	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]
NPO25996	Stenolobium stans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO25086	Viburnum betulifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO26554	Hexagonia speciosa	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26079	Asterococcus muratae	Species	Cerococcidae	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]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23589	Pecten irradians	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7465	Vachellia leucophloea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25393	Coelogyne flavida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26175	Spongionella gracilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10372	Kiggelaria africana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22353	Lucilia caesar	Species	Calliphoridae	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]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	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]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	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]
NPO17771	Senna didymobotrya	Species	Fabaceae	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]
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]
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]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	4.22	ug.mL-1	PMID[561288]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	55.0	%	PMID[561288]
NPT3171	Cell Line	V79	Cricetulus griseus	IC50	=	1.65	ug.mL-1	PMID[561289]

☑ 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 NPC300098 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	256
0.1-0.2	1276
0.2-0.3	2669
0.3-0.4	6622
0.4-0.5	12374
0.5-0.6	11784
0.6-0.7	7144
0.7-0.8	505
0.8-0.85	55
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC290193
0.9187	High Similarity	NPC290955
0.888	High Similarity	NPC246392
0.881	High Similarity	NPC279877
0.881	High Similarity	NPC26532
0.8803	High Similarity	NPC277525
0.875	High Similarity	NPC61788
0.8651	High Similarity	NPC23086
0.8626	High Similarity	NPC476947
0.8615	High Similarity	NPC218838
0.8593	High Similarity	NPC475519
0.8516	High Similarity	NPC329707
0.8507	High Similarity	NPC202260
0.8504	High Similarity	NPC46536
0.8504	High Similarity	NPC138139
0.8455	Intermediate Similarity	NPC87466
0.8397	Intermediate Similarity	NPC473982
0.8372	Intermediate Similarity	NPC207294
0.8372	Intermediate Similarity	NPC112706
0.8333	Intermediate Similarity	NPC477967
0.8321	Intermediate Similarity	NPC89133
0.8321	Intermediate Similarity	NPC263337
0.8309	Intermediate Similarity	NPC67003
0.8308	Intermediate Similarity	NPC59502
0.8308	Intermediate Similarity	NPC208389
0.8268	Intermediate Similarity	NPC16922
0.8261	Intermediate Similarity	NPC476946
0.8222	Intermediate Similarity	NPC307401
0.8203	Intermediate Similarity	NPC118853
0.8201	Intermediate Similarity	NPC476944
0.8188	Intermediate Similarity	NPC52412
0.8162	Intermediate Similarity	NPC472376
0.8154	Intermediate Similarity	NPC83178
0.8148	Intermediate Similarity	NPC46896
0.814	Intermediate Similarity	NPC179354
0.8129	Intermediate Similarity	NPC243577
0.8125	Intermediate Similarity	NPC272899
0.8116	Intermediate Similarity	NPC205765
0.8102	Intermediate Similarity	NPC90953
0.8092	Intermediate Similarity	NPC477040
0.8077	Intermediate Similarity	NPC74612
0.8074	Intermediate Similarity	NPC158525
0.8065	Intermediate Similarity	NPC150895
0.8062	Intermediate Similarity	NPC178382
0.8062	Intermediate Similarity	NPC243269
0.8058	Intermediate Similarity	NPC121158
0.8045	Intermediate Similarity	NPC298190
0.8016	Intermediate Similarity	NPC243704
0.8014	Intermediate Similarity	NPC5676
0.8014	Intermediate Similarity	NPC185456
0.8	Intermediate Similarity	NPC303010
0.8	Intermediate Similarity	NPC294511
0.8	Intermediate Similarity	NPC473885
0.8	Intermediate Similarity	NPC471074
0.8	Intermediate Similarity	NPC121615
0.7986	Intermediate Similarity	NPC212257
0.7972	Intermediate Similarity	NPC93666
0.7971	Intermediate Similarity	NPC474722
0.797	Intermediate Similarity	NPC476925
0.7969	Intermediate Similarity	NPC97566
0.7955	Intermediate Similarity	NPC477123
0.7955	Intermediate Similarity	NPC476917
0.7955	Intermediate Similarity	NPC327527
0.7955	Intermediate Similarity	NPC477966
0.7943	Intermediate Similarity	NPC251865
0.7943	Intermediate Similarity	NPC158871
0.7923	Intermediate Similarity	NPC130275
0.7917	Intermediate Similarity	NPC470998
0.7914	Intermediate Similarity	NPC201370
0.7914	Intermediate Similarity	NPC148374
0.7914	Intermediate Similarity	NPC473983
0.7902	Intermediate Similarity	NPC216755
0.7902	Intermediate Similarity	NPC302987
0.7902	Intermediate Similarity	NPC471174
0.7877	Intermediate Similarity	NPC246164
0.7872	Intermediate Similarity	NPC64568
0.7862	Intermediate Similarity	NPC228842
0.7847	Intermediate Similarity	NPC471007
0.7847	Intermediate Similarity	NPC66991
0.7826	Intermediate Similarity	NPC170604
0.7826	Intermediate Similarity	NPC215109
0.7826	Intermediate Similarity	NPC4764
0.7823	Intermediate Similarity	NPC44606
0.782	Intermediate Similarity	NPC477039
0.7795	Intermediate Similarity	NPC212918
0.7794	Intermediate Similarity	NPC293253
0.7793	Intermediate Similarity	NPC472654
0.7793	Intermediate Similarity	NPC125182
0.7793	Intermediate Similarity	NPC195325
0.7793	Intermediate Similarity	NPC69647
0.7793	Intermediate Similarity	NPC234494
0.7786	Intermediate Similarity	NPC90296
0.7786	Intermediate Similarity	NPC477038
0.7786	Intermediate Similarity	NPC56197
0.7786	Intermediate Similarity	NPC477965
0.7785	Intermediate Similarity	NPC304692
0.7785	Intermediate Similarity	NPC194499
0.7778	Intermediate Similarity	NPC286038
0.7778	Intermediate Similarity	NPC255414
0.7778	Intermediate Similarity	NPC71821
0.777	Intermediate Similarity	NPC471996
0.7769	Intermediate Similarity	NPC471549
0.7769	Intermediate Similarity	NPC317217
0.7769	Intermediate Similarity	NPC473379
0.7762	Intermediate Similarity	NPC56731
0.7761	Intermediate Similarity	NPC198904
0.7761	Intermediate Similarity	NPC223063
0.7761	Intermediate Similarity	NPC120836
0.7755	Intermediate Similarity	NPC33938
0.7746	Intermediate Similarity	NPC267632
0.774	Intermediate Similarity	NPC470997
0.774	Intermediate Similarity	NPC196846
0.7737	Intermediate Similarity	NPC106247
0.7733	Intermediate Similarity	NPC474611
0.7727	Intermediate Similarity	NPC474829
0.7724	Intermediate Similarity	NPC177331
0.7721	Intermediate Similarity	NPC471995
0.7718	Intermediate Similarity	NPC41880
0.7718	Intermediate Similarity	NPC104736
0.7708	Intermediate Similarity	NPC97904
0.7708	Intermediate Similarity	NPC346
0.7703	Intermediate Similarity	NPC114880
0.7698	Intermediate Similarity	NPC473268
0.7698	Intermediate Similarity	NPC470742
0.7676	Intermediate Similarity	NPC20578
0.7676	Intermediate Similarity	NPC62103
0.7671	Intermediate Similarity	NPC211625
0.7667	Intermediate Similarity	NPC7059
0.7667	Intermediate Similarity	NPC88007
0.7667	Intermediate Similarity	NPC195954
0.7664	Intermediate Similarity	NPC471006
0.7656	Intermediate Similarity	NPC144745
0.7656	Intermediate Similarity	NPC208906
0.7655	Intermediate Similarity	NPC250228
0.7652	Intermediate Similarity	NPC188377
0.7652	Intermediate Similarity	NPC65735
0.7651	Intermediate Similarity	NPC35000
0.7651	Intermediate Similarity	NPC179170
0.7647	Intermediate Similarity	NPC477645
0.7643	Intermediate Similarity	NPC236532
0.7643	Intermediate Similarity	NPC476943
0.7639	Intermediate Similarity	NPC290038
0.7635	Intermediate Similarity	NPC470996
0.7635	Intermediate Similarity	NPC469503
0.7635	Intermediate Similarity	NPC472672
0.7634	Intermediate Similarity	NPC36255
0.7634	Intermediate Similarity	NPC263870
0.7632	Intermediate Similarity	NPC79571
0.7632	Intermediate Similarity	NPC18986
0.7626	Intermediate Similarity	NPC146872
0.7616	Intermediate Similarity	NPC140952
0.7616	Intermediate Similarity	NPC84349
0.7616	Intermediate Similarity	NPC472823
0.7616	Intermediate Similarity	NPC116639
0.7612	Intermediate Similarity	NPC474830
0.7606	Intermediate Similarity	NPC20500
0.7597	Intermediate Similarity	NPC21831
0.7597	Intermediate Similarity	NPC187547
0.7591	Intermediate Similarity	NPC471817
0.7589	Intermediate Similarity	NPC233707
0.7586	Intermediate Similarity	NPC233763
0.7584	Intermediate Similarity	NPC34421
0.7584	Intermediate Similarity	NPC237259
0.7584	Intermediate Similarity	NPC302054
0.7584	Intermediate Similarity	NPC30222
0.7584	Intermediate Similarity	NPC253201
0.7584	Intermediate Similarity	NPC282445
0.7584	Intermediate Similarity	NPC98206
0.7584	Intermediate Similarity	NPC178932
0.7582	Intermediate Similarity	NPC283209
0.7574	Intermediate Similarity	NPC939
0.7571	Intermediate Similarity	NPC310830
0.7571	Intermediate Similarity	NPC278832
0.7571	Intermediate Similarity	NPC42400
0.7571	Intermediate Similarity	NPC64157
0.7569	Intermediate Similarity	NPC238843
0.7569	Intermediate Similarity	NPC199044
0.7568	Intermediate Similarity	NPC272590
0.7566	Intermediate Similarity	NPC287559
0.7566	Intermediate Similarity	NPC8389
0.7566	Intermediate Similarity	NPC472299
0.7557	Intermediate Similarity	NPC79557
0.7556	Intermediate Similarity	NPC474438
0.7556	Intermediate Similarity	NPC474279
0.7554	Intermediate Similarity	NPC324117
0.7554	Intermediate Similarity	NPC265793
0.7554	Intermediate Similarity	NPC92941
0.7554	Intermediate Similarity	NPC209858
0.7551	Intermediate Similarity	NPC95526
0.755	Intermediate Similarity	NPC81405
0.7537	Intermediate Similarity	NPC329694
0.7537	Intermediate Similarity	NPC474260
0.7537	Intermediate Similarity	NPC329922
0.7537	Intermediate Similarity	NPC81912
0.7536	Intermediate Similarity	NPC470740
0.7535	Intermediate Similarity	NPC18904
0.7534	Intermediate Similarity	NPC476937
0.7534	Intermediate Similarity	NPC476938
0.7533	Intermediate Similarity	NPC88958
0.7533	Intermediate Similarity	NPC296807

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 NPC300098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	901
0.2-0.3	1769
0.3-0.4	2802
0.4-0.5	2026
0.5-0.6	1159
0.6-0.7	231
0.7-0.8	7
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
0.7655	Intermediate Similarity	NPD6273	Approved
0.7651	Intermediate Similarity	NPD5761	Phase 2
0.7651	Intermediate Similarity	NPD5760	Phase 2
0.7589	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD2344	Approved
0.7132	Intermediate Similarity	NPD5327	Phase 3
0.7113	Intermediate Similarity	NPD5735	Approved
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.708	Intermediate Similarity	NPD1876	Approved
0.7075	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD6765	Approved
0.7055	Intermediate Similarity	NPD6764	Approved
0.7048	Intermediate Similarity	NPD8434	Phase 2
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2309	Approved
0.7015	Intermediate Similarity	NPD5585	Approved
0.6986	Remote Similarity	NPD1471	Phase 3
0.697	Remote Similarity	NPD7157	Approved
0.6947	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD6353	Approved
0.6923	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4060	Phase 1
0.6906	Remote Similarity	NPD2797	Approved
0.6892	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6785	Approved
0.6886	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD6355	Discontinued
0.6861	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2798	Approved
0.6853	Remote Similarity	NPD8032	Phase 2
0.6846	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4110	Phase 3
0.6838	Remote Similarity	NPD4626	Approved
0.6835	Remote Similarity	NPD1283	Approved
0.6831	Remote Similarity	NPD7095	Approved
0.6822	Remote Similarity	NPD2684	Approved
0.6812	Remote Similarity	NPD1608	Approved
0.6809	Remote Similarity	NPD2861	Phase 2
0.6809	Remote Similarity	NPD5736	Approved
0.6806	Remote Similarity	NPD3620	Phase 2
0.6806	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2935	Discontinued
0.6788	Remote Similarity	NPD3496	Discontinued
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5691	Approved
0.6763	Remote Similarity	NPD4359	Approved
0.6757	Remote Similarity	NPD5763	Approved
0.6757	Remote Similarity	NPD2346	Discontinued
0.6757	Remote Similarity	NPD5762	Approved
0.6747	Remote Similarity	NPD6559	Discontinued
0.6738	Remote Similarity	NPD4624	Approved
0.6715	Remote Similarity	NPD1778	Approved
0.6715	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6653	Approved
0.6711	Remote Similarity	NPD2424	Discontinued
0.671	Remote Similarity	NPD7458	Discontinued
0.6708	Remote Similarity	NPD8127	Discontinued
0.6691	Remote Similarity	NPD3091	Approved
0.6691	Remote Similarity	NPD2235	Phase 2
0.6691	Remote Similarity	NPD2231	Phase 2
0.669	Remote Similarity	NPD9494	Approved
0.6689	Remote Similarity	NPD4477	Approved
0.6689	Remote Similarity	NPD2796	Approved
0.6689	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6002	Phase 3
0.6643	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6832	Phase 2
0.6642	Remote Similarity	NPD1651	Approved
0.6623	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3750	Approved
0.6622	Remote Similarity	NPD4308	Phase 3
0.6621	Remote Similarity	NPD6663	Approved
0.6621	Remote Similarity	NPD4870	Approved
0.662	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1281	Approved
0.6617	Remote Similarity	NPD7843	Approved
0.6604	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2651	Approved
0.6603	Remote Similarity	NPD2649	Approved
0.66	Remote Similarity	NPD1549	Phase 2
0.66	Remote Similarity	NPD4534	Discontinued
0.6596	Remote Similarity	NPD6696	Suspended
0.6594	Remote Similarity	NPD2932	Approved
0.6594	Remote Similarity	NPD17	Approved
0.6594	Remote Similarity	NPD3019	Approved
0.6593	Remote Similarity	NPD6671	Approved
0.6591	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1551	Phase 2
0.6577	Remote Similarity	NPD6100	Approved
0.6577	Remote Similarity	NPD6099	Approved
0.6575	Remote Similarity	NPD2979	Phase 3
0.6571	Remote Similarity	NPD9717	Approved
0.6569	Remote Similarity	NPD1894	Discontinued
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7097	Phase 1
0.6552	Remote Similarity	NPD6798	Discontinued
0.6552	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6362	Approved
0.6549	Remote Similarity	NPD1203	Approved
0.6549	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD968	Approved
0.6536	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4908	Phase 1
0.6522	Remote Similarity	NPD1357	Approved
0.6519	Remote Similarity	NPD2629	Approved
0.6513	Remote Similarity	NPD8166	Discontinued
0.651	Remote Similarity	NPD7033	Discontinued
0.6503	Remote Similarity	NPD6584	Phase 3
0.6503	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5647	Approved
0.65	Remote Similarity	NPD2296	Approved
0.65	Remote Similarity	NPD1610	Phase 2
0.65	Remote Similarity	NPD3092	Approved
0.6497	Remote Similarity	NPD3226	Approved
0.6496	Remote Similarity	NPD5536	Phase 2
0.6493	Remote Similarity	NPD5535	Approved
0.649	Remote Similarity	NPD5958	Discontinued
0.649	Remote Similarity	NPD7037	Approved
0.6489	Remote Similarity	NPD290	Approved
0.6486	Remote Similarity	NPD2157	Approved
0.6486	Remote Similarity	NPD4097	Suspended
0.6483	Remote Similarity	NPD7008	Discontinued
0.6481	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD8651	Approved
0.6478	Remote Similarity	NPD6280	Approved
0.6478	Remote Similarity	NPD6279	Approved
0.6478	Remote Similarity	NPD7577	Discontinued
0.6475	Remote Similarity	NPD3095	Discontinued
0.6474	Remote Similarity	NPD920	Approved
0.6467	Remote Similarity	NPD5844	Phase 1
0.6467	Remote Similarity	NPD2438	Suspended
0.6463	Remote Similarity	NPD2238	Phase 2
0.6463	Remote Similarity	NPD3140	Approved
0.6463	Remote Similarity	NPD1240	Approved
0.6463	Remote Similarity	NPD3142	Approved
0.646	Remote Similarity	NPD7768	Phase 2
0.646	Remote Similarity	NPD3882	Suspended
0.6458	Remote Similarity	NPD1712	Approved
0.6456	Remote Similarity	NPD6599	Discontinued
0.6456	Remote Similarity	NPD7028	Phase 2
0.6456	Remote Similarity	NPD4380	Phase 2
0.6454	Remote Similarity	NPD2230	Approved
0.6454	Remote Similarity	NPD2232	Approved
0.6454	Remote Similarity	NPD2233	Approved
0.6452	Remote Similarity	NPD4661	Approved
0.6452	Remote Similarity	NPD4662	Approved
0.6452	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD9545	Approved
0.6447	Remote Similarity	NPD2800	Approved
0.6444	Remote Similarity	NPD5283	Phase 1
0.6442	Remote Similarity	NPD5494	Approved
0.6438	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3847	Discontinued
0.6429	Remote Similarity	NPD6667	Approved
0.6429	Remote Similarity	NPD6666	Approved
0.6429	Remote Similarity	NPD7440	Discontinued
0.6429	Remote Similarity	NPD7236	Approved
0.642	Remote Similarity	NPD3749	Approved
0.642	Remote Similarity	NPD7075	Discontinued
0.6419	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5124	Phase 1
0.6415	Remote Similarity	NPD7411	Suspended
0.6408	Remote Similarity	NPD6582	Phase 2
0.6408	Remote Similarity	NPD3685	Discontinued
0.6408	Remote Similarity	NPD6583	Phase 3
0.64	Remote Similarity	NPD1510	Phase 2
0.64	Remote Similarity	NPD3748	Approved
0.6395	Remote Similarity	NPD4062	Phase 3
0.6395	Remote Similarity	NPD6233	Phase 2
0.6395	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD9092	Discovery
0.6376	Remote Similarity	NPD1607	Approved
0.6375	Remote Similarity	NPD1934	Approved
0.6375	Remote Similarity	NPD6801	Discontinued
0.6375	Remote Similarity	NPD6844	Discontinued
0.637	Remote Similarity	NPD821	Approved
0.637	Remote Similarity	NPD4625	Phase 3
0.6369	Remote Similarity	NPD3869	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data