NPASS Compound

Structure

CID201459 OpenBabel06191715592D 32 36 0 0 1 0 0 0 0 0999 V2000 5.7135 0.3460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1803 0.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4468 1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9548 0.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0243 1.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8700 -1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6429 0.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1072 -1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6420 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6434 2.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 2.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2869 -1.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 -1.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 -2.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7771 0.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1069 -0.4732 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6432 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6423 0.9482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4643 2.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4649 -0.4736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4637 1.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8214 1.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8217 -0.4741 0.0000 C 0 0 1 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 2.4652 -1.4217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1702 -3.0039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3159 2.8610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 30 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	5.437
LogD:	5.206
LogS:	-5.596
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	4.74
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248
MDCK Permeability:	1.2907516975246836e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.709
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	89.73944854736328%
Volume Distribution (VD):	1.015
Pgp-substrate:	1.8414162397384644%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.8
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	5.087
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.384
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.126
Carcinogencity:	0.011
Eye Corrosion:	0.218
Eye Irritation:	0.499
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC201459

Natural Product ID:	NPC201459
*Common Name:**	Betulone
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:	Betulone
Standard InCHIKey:	JYDNKGUBLIKNAM-CNRMHUMKSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-23,25,31H,1,8-18H2,2-7H3/t20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469284
PubChem CID:	10411004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO31410	Cupania cinerea	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[21438586]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO40286	Phoradendron vernicosum	Species	Viscaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29120172]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23989	Cyclamen neapolitanum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1
IC50	28
Others	12

Activity Type	# Activity
Cell Line	27
NON-MOLECULAR	9
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	ED50	=	0.19	uM	PMID[456543]
NPT319	Cell Line	B16	Mus musculus	IC50	=	29300.0	nM	PMID[456543]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[456544]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[456544]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10.0	ug.mL-1	PMID[456544]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	22200.0	nM	PMID[456545]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[456546]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[456546]
NPT460	Cell Line	MT2	Homo sapiens	CC50	>	100000.0	nM	PMID[456547]
NPT2245	Cell Line	SiHa	Homo sapiens	CC50	=	197400.0	nM	PMID[456549]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	135700.0	nM	PMID[456549]
NPT83	Cell Line	MCF7	Homo sapiens	CC50	>	500000.0	nM	PMID[456549]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	CC50	=	135800.0	nM	PMID[456549]
NPT90	Cell Line	DU-145	Homo sapiens	CC50	=	102400.0	nM	PMID[456549]
NPT91	Cell Line	KB	Homo sapiens	CC50	>	500000.0	nM	PMID[456549]
NPT1171	Cell Line	HEp-2	Homo sapiens	CC50	>	500000.0	nM	PMID[456549]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	500000.0	nM	PMID[456549]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	500000.0	nM	PMID[456549]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT2245	Cell Line	SiHa	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	500000.0	nM	PMID[456549]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	500000.0	nM	PMID[456549]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3000.0	nM	PMID[456545]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	18900.0	nM	PMID[456545]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[456546]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[456547]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	4100.0	nM	PMID[456547]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	24.5	n.a.	PMID[456547]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13250.0	nM	PMID[456548]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34030.0	nM	PMID[456548]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22480.0	nM	PMID[456548]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18220.0	nM	PMID[456548]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32940.0	nM	PMID[456548]

☑ 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 NPC201459 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	159
0.1-0.2	1654
0.2-0.3	8900
0.3-0.4	14973
0.4-0.5	6183
0.5-0.6	5104
0.6-0.7	4001
0.7-0.8	1493
0.8-0.85	158
0.85-0.9	49
0.9-0.95	16
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC103754
0.9733	High Similarity	NPC474484
0.9481	High Similarity	NPC475726
0.9481	High Similarity	NPC175410
0.9481	High Similarity	NPC472743
0.9359	High Similarity	NPC474482
0.9359	High Similarity	NPC474233
0.9359	High Similarity	NPC475745
0.9241	High Similarity	NPC292553
0.9241	High Similarity	NPC201655
0.9211	High Similarity	NPC192744
0.92	High Similarity	NPC106078
0.9125	High Similarity	NPC472738
0.9114	High Similarity	NPC74595
0.9114	High Similarity	NPC264665
0.9103	High Similarity	NPC145143
0.9103	High Similarity	NPC477858
0.9012	High Similarity	NPC57469
0.9012	High Similarity	NPC4643
0.9	High Similarity	NPC264317
0.9	High Similarity	NPC294438
0.8947	High Similarity	NPC68828
0.8902	High Similarity	NPC472739
0.8902	High Similarity	NPC474719
0.8889	High Similarity	NPC2783
0.8889	High Similarity	NPC269396
0.8889	High Similarity	NPC98236
0.8889	High Similarity	NPC12774
0.8846	High Similarity	NPC164999
0.8831	High Similarity	NPC63020
0.878	High Similarity	NPC93778
0.878	High Similarity	NPC269360
0.878	High Similarity	NPC264005
0.878	High Similarity	NPC33768
0.8765	High Similarity	NPC76518
0.875	High Similarity	NPC245866
0.875	High Similarity	NPC472740
0.8734	High Similarity	NPC3915
0.8718	High Similarity	NPC215843
0.8701	High Similarity	NPC66105
0.8675	High Similarity	NPC471900
0.8675	High Similarity	NPC16377
0.8659	High Similarity	NPC70661
0.8642	High Similarity	NPC214043
0.8642	High Similarity	NPC85774
0.8642	High Similarity	NPC82902
0.8642	High Similarity	NPC221758
0.8642	High Similarity	NPC59453
0.8625	High Similarity	NPC310989
0.8625	High Similarity	NPC46881
0.8625	High Similarity	NPC110780
0.8571	High Similarity	NPC246445
0.8571	High Similarity	NPC57954
0.8571	High Similarity	NPC220498
0.8571	High Similarity	NPC213832
0.8537	High Similarity	NPC474218
0.8537	High Similarity	NPC469948
0.8537	High Similarity	NPC471224
0.8519	High Similarity	NPC471036
0.8519	High Similarity	NPC118800
0.8519	High Similarity	NPC291320
0.8519	High Similarity	NPC472498
0.85	High Similarity	NPC328264
0.8488	Intermediate Similarity	NPC244356
0.8488	Intermediate Similarity	NPC224060
0.8471	Intermediate Similarity	NPC169933
0.8462	Intermediate Similarity	NPC471035
0.8462	Intermediate Similarity	NPC149249
0.8462	Intermediate Similarity	NPC212661
0.8452	Intermediate Similarity	NPC193360
0.8452	Intermediate Similarity	NPC4309
0.8442	Intermediate Similarity	NPC231256
0.8442	Intermediate Similarity	NPC240235
0.8442	Intermediate Similarity	NPC178383
0.8442	Intermediate Similarity	NPC195155
0.8442	Intermediate Similarity	NPC212879
0.8442	Intermediate Similarity	NPC104387
0.8442	Intermediate Similarity	NPC174964
0.8442	Intermediate Similarity	NPC97534
0.8434	Intermediate Similarity	NPC51014
0.8434	Intermediate Similarity	NPC31564
0.8434	Intermediate Similarity	NPC474732
0.8434	Intermediate Similarity	NPC474778
0.8434	Intermediate Similarity	NPC145879
0.8434	Intermediate Similarity	NPC474733
0.8434	Intermediate Similarity	NPC80590
0.8434	Intermediate Similarity	NPC469994
0.8421	Intermediate Similarity	NPC244708
0.8421	Intermediate Similarity	NPC330659
0.8421	Intermediate Similarity	NPC36310
0.8421	Intermediate Similarity	NPC161187
0.8415	Intermediate Similarity	NPC146683
0.8415	Intermediate Similarity	NPC473246
0.8415	Intermediate Similarity	NPC237712
0.8415	Intermediate Similarity	NPC180834
0.8415	Intermediate Similarity	NPC263974
0.8395	Intermediate Similarity	NPC170985
0.8395	Intermediate Similarity	NPC151519
0.8378	Intermediate Similarity	NPC473225
0.8375	Intermediate Similarity	NPC472478
0.8372	Intermediate Similarity	NPC272746
0.8372	Intermediate Similarity	NPC475416
0.8356	Intermediate Similarity	NPC43300
0.8354	Intermediate Similarity	NPC82635
0.8353	Intermediate Similarity	NPC247312
0.8353	Intermediate Similarity	NPC271974
0.8353	Intermediate Similarity	NPC122116
0.8333	Intermediate Similarity	NPC78067
0.8333	Intermediate Similarity	NPC20466
0.8333	Intermediate Similarity	NPC317590
0.8333	Intermediate Similarity	NPC5767
0.8333	Intermediate Similarity	NPC14112
0.8333	Intermediate Similarity	NPC86305
0.8333	Intermediate Similarity	NPC475742
0.8333	Intermediate Similarity	NPC58063
0.8333	Intermediate Similarity	NPC96496
0.8333	Intermediate Similarity	NPC90652
0.8333	Intermediate Similarity	NPC134197
0.8333	Intermediate Similarity	NPC278091
0.8333	Intermediate Similarity	NPC93662
0.8333	Intermediate Similarity	NPC475740
0.8313	Intermediate Similarity	NPC102292
0.8313	Intermediate Similarity	NPC190704
0.8313	Intermediate Similarity	NPC474083
0.8313	Intermediate Similarity	NPC471034
0.8313	Intermediate Similarity	NPC274724
0.8313	Intermediate Similarity	NPC133954
0.8312	Intermediate Similarity	NPC25511
0.8312	Intermediate Similarity	NPC62657
0.8312	Intermediate Similarity	NPC192638
0.8312	Intermediate Similarity	NPC159497
0.8293	Intermediate Similarity	NPC471037
0.8289	Intermediate Similarity	NPC156277
0.8289	Intermediate Similarity	NPC58057
0.8289	Intermediate Similarity	NPC151018
0.8289	Intermediate Similarity	NPC320549
0.8276	Intermediate Similarity	NPC473690
0.8276	Intermediate Similarity	NPC291373
0.8276	Intermediate Similarity	NPC471902
0.8276	Intermediate Similarity	NPC287118
0.8272	Intermediate Similarity	NPC164210
0.8272	Intermediate Similarity	NPC147066
0.8267	Intermediate Similarity	NPC475952
0.8256	Intermediate Similarity	NPC85173
0.8256	Intermediate Similarity	NPC126993
0.8256	Intermediate Similarity	NPC46758
0.825	Intermediate Similarity	NPC472490
0.825	Intermediate Similarity	NPC471475
0.825	Intermediate Similarity	NPC476812
0.8235	Intermediate Similarity	NPC183374
0.8235	Intermediate Similarity	NPC211162
0.8235	Intermediate Similarity	NPC328313
0.8235	Intermediate Similarity	NPC146937
0.8235	Intermediate Similarity	NPC470417
0.8228	Intermediate Similarity	NPC472746
0.8228	Intermediate Similarity	NPC248830
0.8228	Intermediate Similarity	NPC476811
0.8228	Intermediate Similarity	NPC119355
0.8228	Intermediate Similarity	NPC221420
0.8228	Intermediate Similarity	NPC23884
0.8228	Intermediate Similarity	NPC202540
0.8228	Intermediate Similarity	NPC212241
0.8219	Intermediate Similarity	NPC27243
0.8219	Intermediate Similarity	NPC476737
0.8214	Intermediate Similarity	NPC213412
0.8214	Intermediate Similarity	NPC473168
0.8214	Intermediate Similarity	NPC72133
0.8214	Intermediate Similarity	NPC475862
0.8214	Intermediate Similarity	NPC155011
0.8214	Intermediate Similarity	NPC74363
0.8214	Intermediate Similarity	NPC471737
0.8193	Intermediate Similarity	NPC58841
0.8193	Intermediate Similarity	NPC161423
0.8193	Intermediate Similarity	NPC227064
0.8193	Intermediate Similarity	NPC475509
0.8193	Intermediate Similarity	NPC321187
0.8193	Intermediate Similarity	NPC329043
0.8193	Intermediate Similarity	NPC473157
0.8182	Intermediate Similarity	NPC277399
0.8182	Intermediate Similarity	NPC279241
0.8182	Intermediate Similarity	NPC232112
0.8182	Intermediate Similarity	NPC310766
0.8182	Intermediate Similarity	NPC303863
0.8161	Intermediate Similarity	NPC160506
0.8161	Intermediate Similarity	NPC471901
0.8158	Intermediate Similarity	NPC91369
0.8158	Intermediate Similarity	NPC108131
0.8148	Intermediate Similarity	NPC2482
0.814	Intermediate Similarity	NPC474245
0.814	Intermediate Similarity	NPC26959
0.814	Intermediate Similarity	NPC477943
0.814	Intermediate Similarity	NPC2983
0.814	Intermediate Similarity	NPC24772
0.814	Intermediate Similarity	NPC32830
0.814	Intermediate Similarity	NPC116146
0.814	Intermediate Similarity	NPC473999
0.814	Intermediate Similarity	NPC268406
0.814	Intermediate Similarity	NPC309603
0.814	Intermediate Similarity	NPC1015
0.814	Intermediate Similarity	NPC186688

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 NPC201459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2087
0.2-0.3	4446
0.3-0.4	1666
0.4-0.5	379
0.5-0.6	154
0.6-0.7	171
0.7-0.8	78
0.8-0.85	11
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7520	Clinical (unspecified phase)
0.8987	High Similarity	NPD4788	Approved
0.8642	High Similarity	NPD4786	Approved
0.84	Intermediate Similarity	NPD4789	Approved
0.8395	Intermediate Similarity	NPD3667	Approved
0.8289	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3665	Phase 1
0.8193	Intermediate Similarity	NPD3666	Approved
0.8193	Intermediate Similarity	NPD3133	Approved
0.8161	Intermediate Similarity	NPD8035	Phase 2
0.8161	Intermediate Similarity	NPD8034	Phase 2
0.8158	Intermediate Similarity	NPD4245	Approved
0.8158	Intermediate Similarity	NPD4244	Approved
0.814	Intermediate Similarity	NPD5328	Approved
0.8026	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3698	Phase 2
0.8	Intermediate Similarity	NPD3618	Phase 1
0.7955	Intermediate Similarity	NPD6079	Approved
0.7952	Intermediate Similarity	NPD4223	Phase 3
0.7952	Intermediate Similarity	NPD4221	Approved
0.7931	Intermediate Similarity	NPD4753	Phase 2
0.7895	Intermediate Similarity	NPD5360	Phase 3
0.7895	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5329	Approved
0.7848	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5279	Phase 3
0.7765	Intermediate Similarity	NPD4197	Approved
0.7753	Intermediate Similarity	NPD7515	Phase 2
0.7683	Intermediate Similarity	NPD3617	Approved
0.7667	Intermediate Similarity	NPD4202	Approved
0.7667	Intermediate Similarity	NPD6399	Phase 3
0.7654	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD4224	Phase 2
0.7614	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6081	Approved
0.7586	Intermediate Similarity	NPD4689	Approved
0.7586	Intermediate Similarity	NPD5205	Approved
0.7586	Intermediate Similarity	NPD4693	Phase 3
0.7586	Intermediate Similarity	NPD4690	Approved
0.7586	Intermediate Similarity	NPD4138	Approved
0.7586	Intermediate Similarity	NPD4688	Approved
0.7561	Intermediate Similarity	NPD6116	Phase 1
0.7558	Intermediate Similarity	NPD3668	Phase 3
0.7531	Intermediate Similarity	NPD6942	Approved
0.7531	Intermediate Similarity	NPD7339	Approved
0.7531	Intermediate Similarity	NPD3703	Phase 2
0.7527	Intermediate Similarity	NPD6084	Phase 2
0.7527	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD5210	Approved
0.747	Intermediate Similarity	NPD6115	Approved
0.747	Intermediate Similarity	NPD6697	Approved
0.747	Intermediate Similarity	NPD6118	Approved
0.747	Intermediate Similarity	NPD6114	Approved
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4697	Phase 3
0.7416	Intermediate Similarity	NPD6672	Approved
0.7416	Intermediate Similarity	NPD5737	Approved
0.7412	Intermediate Similarity	NPD4692	Approved
0.7412	Intermediate Similarity	NPD4139	Approved
0.7391	Intermediate Similarity	NPD7748	Approved
0.7386	Intermediate Similarity	NPD5690	Phase 2
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD4694	Approved
0.7386	Intermediate Similarity	NPD5280	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7375	Intermediate Similarity	NPD4758	Discontinued
0.734	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD4755	Approved
0.7262	Intermediate Similarity	NPD3671	Phase 1
0.725	Intermediate Similarity	NPD4747	Approved
0.7229	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6903	Approved
0.7195	Intermediate Similarity	NPD6924	Approved
0.7195	Intermediate Similarity	NPD6926	Approved
0.7191	Intermediate Similarity	NPD6098	Approved
0.7191	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5286	Approved
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD4700	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7176	Intermediate Similarity	NPD7645	Phase 2
0.7176	Intermediate Similarity	NPD4195	Approved
0.716	Intermediate Similarity	NPD4243	Approved
0.716	Intermediate Similarity	NPD5777	Approved
0.7158	Intermediate Similarity	NPD7902	Approved
0.7128	Intermediate Similarity	NPD5695	Phase 3
0.7125	Intermediate Similarity	NPD4137	Phase 3
0.7113	Intermediate Similarity	NPD5223	Approved
0.7108	Intermediate Similarity	NPD3702	Approved
0.7093	Intermediate Similarity	NPD4695	Discontinued
0.7083	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD5364	Discontinued
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD4691	Approved
0.7024	Intermediate Similarity	NPD6933	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD4623	Approved
0.7	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7128	Approved
0.6989	Remote Similarity	NPD5284	Approved
0.6989	Remote Similarity	NPD5281	Approved
0.6988	Remote Similarity	NPD5733	Approved
0.6988	Remote Similarity	NPD4785	Approved
0.6988	Remote Similarity	NPD4784	Approved
0.697	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD4754	Approved
0.6957	Remote Similarity	NPD6904	Approved
0.6957	Remote Similarity	NPD6673	Approved
0.6957	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6080	Approved
0.6931	Remote Similarity	NPD6412	Phase 2
0.6914	Remote Similarity	NPD6923	Approved
0.6914	Remote Similarity	NPD6922	Approved
0.6907	Remote Similarity	NPD7638	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6882	Remote Similarity	NPD4096	Approved
0.6863	Remote Similarity	NPD7320	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5208	Approved
0.6842	Remote Similarity	NPD7900	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7640	Approved
0.6837	Remote Similarity	NPD7639	Approved
0.6832	Remote Similarity	NPD4768	Approved
0.6832	Remote Similarity	NPD4767	Approved
0.6829	Remote Similarity	NPD7143	Approved
0.6829	Remote Similarity	NPD7144	Approved
0.6796	Remote Similarity	NPD6373	Approved
0.6796	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD4687	Approved
0.6786	Remote Similarity	NPD4058	Approved
0.6782	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.6747	Remote Similarity	NPD5276	Approved
0.6747	Remote Similarity	NPD7152	Approved
0.6747	Remote Similarity	NPD7151	Approved
0.6747	Remote Similarity	NPD7150	Approved
0.6737	Remote Similarity	NPD5133	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD7290	Approved
0.6707	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5275	Approved
0.6706	Remote Similarity	NPD4190	Phase 3
0.6705	Remote Similarity	NPD6930	Phase 2
0.6705	Remote Similarity	NPD6931	Approved
0.6699	Remote Similarity	NPD5168	Approved
0.6699	Remote Similarity	NPD4730	Approved
0.6699	Remote Similarity	NPD6011	Approved
0.6699	Remote Similarity	NPD4729	Approved
0.6699	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6632	Remote Similarity	NPD5693	Phase 1
0.6632	Remote Similarity	NPD6050	Approved
0.6627	Remote Similarity	NPD4787	Phase 1
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD5251	Approved
0.6571	Remote Similarity	NPD5247	Approved
0.6571	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD5135	Approved
0.6559	Remote Similarity	NPD4751	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