NPASS Compound

Structure

CID158329 OpenBabel06191715532D 46 51 0 0 1 0 0 0 0 0999 V2000 3.6982 -2.5082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9282 -1.7980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2690 -2.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1513 -2.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0820 -0.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1614 -1.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6658 -1.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2882 -0.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1082 -0.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6982 -1.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4412 -1.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1513 -0.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3212 -0.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3026 1.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6982 0.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 0.9971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9172 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 1.3337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2647 0.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1082 -1.7980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4412 -2.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6780 -0.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 0.7522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7269 0.9971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1513 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5756 0.9971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5360 -0.1223 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5756 0.9971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1513 1.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7269 0.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5756 0.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7417 0.2273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6307 -0.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1387 -0.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 0.3324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5246 -0.1574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5756 0.3324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1513 2.1494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.1494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4339 0.4187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9875 -1.1416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2267 -1.0598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3026 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0574 -0.8289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 35 1 0 0 0 0 7 35 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 36 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 26 2 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 22 34 1 0 0 0 0 23 18 1 6 0 0 0 23 33 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 30 1 0 0 0 0 27 35 1 0 0 0 0 27 38 1 6 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 32 2 0 0 0 0 29 39 1 0 0 0 0 30 40 2 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 37 1 0 0 0 0 33 41 2 0 0 0 0 34 42 2 0 0 0 0 34 43 1 0 0 0 0 35 46 1 0 0 0 0 36 8 1 6 0 0 0 36 44 1 0 0 0 0 37 38 1 6 0 0 0 37 46 1 0 0 0 0 38 26 1 6 0 0 0 38 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.3
Volume:	655.786
LogP:	7.96
LogD:	4.202
LogS:	-3.259
# Rotatable Bonds:	8
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	6.968
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.874
MDCK Permeability:	2.0986151866964065e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.399
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.204

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	92.1287612915039%
Volume Distribution (VD):	1.279
Pgp-substrate:	7.025338649749756%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.168
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.709

ADMET: Excretion

Clearance (CL):	2.191
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.965
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.235
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC158329

Natural Product ID:	NPC158329
*Common Name:**	Gambogic Acid
IUPAC Name:	n.a.
Synonyms:	(-)-Gambogic Acid; Gambogic Acid; R-Gambogic Acid
Standard InCHIKey:	GEZHEQNLKAOMCA-RRZNCOCZSA-N
Standard InCHI:	InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1
SMILES:	CC(=CCc1c2O[C@]34[C@@]5(C/C=C(C(=O)O)/C)OC([C@@H]4C[C@H](C5=O)C=C3C(=O)c2c(c2c1O[C@](C)(CCC=C(C)C)C=C2)O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555017
PubChem CID:	9852185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO17342	Microcosmus vulgaris	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785429]
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	whole plant	Guangxi Province, China	2002-AUG	PMID[15921435]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO33582	Garcinia harburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO40521	Garcinia bracteata	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29565129]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19508	Toxicodendron radicans	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6202	Aglaomorpha coronans	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19429	Millettia auriculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19760	Fragaria chiloensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18834	Scrophularia glabrata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13703	Croton discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1917	Prosopis nigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28098	Rhizomnium pseudopunctatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17093	Callitriche stagnalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO64	Lysidice brevicalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4723	Phanerochaete velutina	Species	Phanerochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19508	Toxicodendron radicans	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18593	Wrightia coccinea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15765	Vernonanthura discolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17342	Microcosmus vulgaris	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4477	Fasciola hepatica	Species	Fasciolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14692	Salix babylonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11950	Ruscus hypoglossum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6202	Aglaomorpha coronans	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20810	Lobaria adusta	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5660	Scleropyrum maingayi	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19300	Scleroderma tinctorium	Species	Sclerodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22632	Pteris glauca	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19429	Millettia auriculata	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
EC50	8
ED50	1
GI50	8
IC50	68
Kd	3
Ki	4
MIC	2
Others	78

Activity Type	# Activity
Cell Line	87
CELL-LINE	2
Individual Protein	26
NON-MOLECULAR	6
Organism	27
Others	14
PROTEIN COMPLEX	4
Protein Family	3
SINGLE PROTEIN	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	EC50	=	700.0	nM	PMID[476848]
NPT393	Cell Line	HCT-116	Homo sapiens	EC50	=	700.0	nM	PMID[476848]
NPT4783	Cell Line	SNU-398	Homo sapiens	EC50	=	700.0	nM	PMID[476848]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	200.0	nM	PMID[476848]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	100.0	nM	PMID[476848]
NPT4783	Cell Line	SNU-398	Homo sapiens	GI50	=	200.0	nM	PMID[476848]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5810.0	nM	PMID[476850]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	4510.0	nM	PMID[476850]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	3060.0	nM	PMID[476850]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5610.0	nM	PMID[476850]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3310.0	nM	PMID[476850]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	700.0	nM	PMID[476851]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2400.0	nM	PMID[476852]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	1470.0	nM	PMID[476852]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	500.0	nM	PMID[476852]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3650.0	nM	PMID[476853]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	2830.0	nM	PMID[476853]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3520.0	nM	PMID[476853]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	2080.0	nM	PMID[476853]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2190.0	nM	PMID[476854]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	2350.0	nM	PMID[476854]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	3200.0	nM	PMID[476854]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2400.0	nM	PMID[476854]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	45.27	%	PMID[476854]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.48	uM	PMID[476855]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	1500.0	nM	PMID[476856]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	2000.0	nM	PMID[476856]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	=	800.0	nM	PMID[476856]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	750.0	nM	PMID[476857]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	1130.0	nM	PMID[476857]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1170.0	nM	PMID[476857]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1100.0	nM	PMID[476858]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	2560.0	nM	PMID[476858]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[476859]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[476859]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[476859]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	1.17	%	PMID[476860]
NPT4786	Individual Protein	Thioredoxin, mitochondrial	Homo sapiens	Kinact	=	0.037	/min	PMID[476862]
NPT4787	Individual Protein	Thioredoxin	Homo sapiens	Kinact	=	0.063	/min	PMID[476862]
NPT4786	Individual Protein	Thioredoxin, mitochondrial	Homo sapiens	Ki	=	1310.0	nM	PMID[476862]
NPT4787	Individual Protein	Thioredoxin	Homo sapiens	Ki	=	3110.0	nM	PMID[476862]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	2560.0	nM	PMID[476863]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1100.0	nM	PMID[476863]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	890.0	nM	PMID[476863]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	<	2000.0	nM	PMID[476866]
NPT80	Cell Line	Raji	Homo sapiens	EC50	=	240.0	nM	PMID[476866]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	=	210.0	nM	PMID[476866]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	=	210.0	nM	PMID[476866]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	890.0	nM	PMID[476867]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1100.0	nM	PMID[476867]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	2560.0	nM	PMID[476867]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	4.0	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	8.57	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	32.3	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	27.6	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	13.7	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	12.6	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	36.5	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	2.6	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	6.0	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	76.6	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	5.8	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	33.4	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	2.8	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	Activity	=	38.5	%	PMID[476869]
NPT1125	Cell Line	T98G	Homo sapiens	IC50	<=	300.0	nM	PMID[476869]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3400.0	nM	PMID[476870]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	1720.0	nM	PMID[476870]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	790.0	nM	PMID[476871]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	470.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ratio IC50	=	30.0	n.a.	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	190.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	12.57	optical density/minute	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	12.95	optical density/minute	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	13.73	optical density/minute	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	4460000.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	6840000.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	12650000.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	499.0	nM	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ratio Ki	=	70.98	n.a.	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	K	=	0.0751	/uM/s	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	K	=	0.0249	/uM/s	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ratio Ki	=	74.24	n.a.	PMID[476872]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ratio Ki	=	82.89	n.a.	PMID[476872]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	600.0	nM	PMID[476874]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	300.0	nM	PMID[476874]
NPT5230	Cell Line	Breast carcinoma cells	Homo sapiens	Ratio IC50	=	20.0	n.a.	PMID[476876]
NPT5230	Cell Line	Breast carcinoma cells	Homo sapiens	IC50	=	420.0	nM	PMID[476876]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	170.0	nM	PMID[476878]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	FC	=	1.31	n.a.	PMID[476878]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1470.0	nM	PMID[476879]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2360.0	nM	PMID[476879]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1330.0	nM	PMID[476879]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	4270.0	nM	PMID[476879]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3110.0	nM	PMID[476879]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	31.8	%	PMID[476879]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	33.0	%	PMID[476879]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2190.0	nM	PMID[476882]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1190.0	nM	PMID[476882]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2370.0	nM	PMID[476882]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	890.0	nM	PMID[476882]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1200.0	nM	PMID[476882]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1250.0	nM	PMID[476882]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1550.0	nM	PMID[476887]
NPT2	Others	Unspecified		EC50	=	20.0	nM	PMID[476849]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	24.41	%	PMID[476849]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	85.83	%	PMID[476849]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1540.0	nM	PMID[476852]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	27.6	g	PMID[476854]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[476856]
NPT2	Others	Unspecified		Activity	=	10.0	%	PMID[476856]
NPT2264	Protein Family	Heat shock protein HSP90	Homo sapiens	Kd	=	9800.0	nM	PMID[476856]
NPT2264	Protein Family	Heat shock protein HSP90	Homo sapiens	Kd	=	7600.0	nM	PMID[476856]
NPT2264	Protein Family	Heat shock protein HSP90	Homo sapiens	Kd	=	7000.0	nM	PMID[476856]
NPT35	Others	n.a.		Solubility	=	13.0	ug.mL-1	PMID[476857]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4700.0	nM	PMID[476857]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	240.0	nM	PMID[476857]
NPT2	Others	Unspecified		Inhibition	=	50.2	%	PMID[476858]
NPT981	Individual Protein	Inhibitor of nuclear factor kappa B kinase beta subunit	Homo sapiens	IC50	=	3070.0	nM	PMID[476858]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.4	ug.mL-1	PMID[476859]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	8.47	%	PMID[476860]
NPT35	Others	n.a.		LogD	=	3.6	n.a.	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	Cmax	=	0.191	ug.mL-1	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	2005.0	ng.hr.mL-1	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	1072.0	ng.hr.mL-1	PMID[476863]
NPT35	Others	n.a.		Solubility	=	15000.0	nM	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	CL	=	41.02	mL.min-1.kg-1	PMID[476863]
NPT27	Others	Unspecified		permeability	=	26.5	ucm/s	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	Vd	=	19.7	L.kg-1	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	5.06	hr	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	4.51	hr	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	3.29	hr	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	2.26	hr	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	Tmax	=	0.5	hr	PMID[476863]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	69.11	%	PMID[476863]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	36.36	%	PMID[476863]
NPT32	Organism	Mus musculus	Mus musculus	F	=	13.4	%	PMID[476863]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	75.57	%	PMID[476865]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	65.8	%	PMID[476865]
NPT35	Others	n.a.		Solubility	=	15000.0	nM	PMID[476867]
NPT27	Others	Unspecified		permeability	=	0.9	ucm/s	PMID[476867]
NPT27	Others	Unspecified		permeability	=	1.8	ucm/s	PMID[476867]
NPT27	Others	Unspecified		permeability	=	2.3	ucm/s	PMID[476867]
NPT27	Others	Unspecified		Drug excretion	=	1.04	%	PMID[476868]
NPT27	Others	Unspecified		Retention_time	=	44.8	min	PMID[476868]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	16.59	mm	PMID[476870]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25000.0	nM	PMID[476870]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12500.0	nM	PMID[476870]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	17.29	mm	PMID[476870]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	25.0	uM	PMID[476870]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	50.0	uM	PMID[476870]
NPT22517	SINGLE PROTEIN	Regulator of G-protein signaling 17	Homo sapiens	IC50	=	10000.0	nM	PMID[476873]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	3.96	%	PMID[476875]
NPT23298	CELL-LINE	A549/TR	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT21782	CELL-LINE	A549/CDDP	Homo sapiens	IC50	=	290.0	nM	PMID[476877]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	96.0	%	PMID[476880]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	100.0	%	PMID[476880]
NPT22517	SINGLE PROTEIN	Regulator of G-protein signaling 17	Homo sapiens	IC50	=	10790.0	nM	PMID[476881]
NPT22517	SINGLE PROTEIN	Regulator of G-protein signaling 17	Homo sapiens	IC50	=	12260.0	nM	PMID[476881]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	IC50	=	21980.0	nM	PMID[476882]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	11.72	%	PMID[476883]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.977	%	PMID[476884]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.31	%	PMID[476885]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.34	%	PMID[476886]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[476888]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[476888]

☑ 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 NPC158329 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	399
0.1-0.2	1602
0.2-0.3	3207
0.3-0.4	7097
0.4-0.5	10770
0.5-0.6	6254
0.6-0.7	5926
0.7-0.8	7094
0.8-0.85	271
0.85-0.9	31
0.9-0.95	27
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC40089
1.0	High Similarity	NPC476146
0.9874	High Similarity	NPC55422
0.9874	High Similarity	NPC75141
0.9874	High Similarity	NPC47634
0.9814	High Similarity	NPC476152
0.9812	High Similarity	NPC476196
0.975	High Similarity	NPC476216
0.975	High Similarity	NPC41598
0.9691	High Similarity	NPC476229
0.9686	High Similarity	NPC189689
0.9623	High Similarity	NPC131578
0.9571	High Similarity	NPC476139
0.9515	High Similarity	NPC476199
0.9515	High Similarity	NPC476210
0.9444	High Similarity	NPC223413
0.9434	High Similarity	NPC286422
0.9394	High Similarity	NPC162248
0.939	High Similarity	NPC476159
0.9387	High Similarity	NPC63514
0.9333	High Similarity	NPC476311
0.9268	High Similarity	NPC102810
0.9226	High Similarity	NPC473607
0.9222	High Similarity	NPC227275
0.9198	High Similarity	NPC94796
0.9167	High Similarity	NPC233978
0.9146	High Similarity	NPC476255
0.9146	High Similarity	NPC476056
0.9112	High Similarity	NPC473729
0.9091	High Similarity	NPC193222
0.9074	High Similarity	NPC43490
0.9074	High Similarity	NPC475107
0.903	High Similarity	NPC62444
0.8994	High Similarity	NPC476162
0.8951	High Similarity	NPC476930
0.8935	High Similarity	NPC475398
0.8929	High Similarity	NPC169018
0.8909	High Similarity	NPC476931
0.8882	High Similarity	NPC98943
0.8817	High Similarity	NPC118128
0.8788	High Similarity	NPC476929
0.8765	High Similarity	NPC475080
0.8765	High Similarity	NPC147363
0.8765	High Similarity	NPC73899
0.8765	High Similarity	NPC17105
0.8765	High Similarity	NPC474276
0.8743	High Similarity	NPC473908
0.8735	High Similarity	NPC475106
0.8706	High Similarity	NPC477529
0.8667	High Similarity	NPC125969
0.8647	High Similarity	NPC193698
0.8639	High Similarity	NPC292233
0.8614	High Similarity	NPC172687
0.8605	High Similarity	NPC294149
0.8598	High Similarity	NPC469934
0.8563	High Similarity	NPC61382
0.8563	High Similarity	NPC103816
0.8555	High Similarity	NPC469345
0.8554	High Similarity	NPC474373
0.8554	High Similarity	NPC311574
0.8554	High Similarity	NPC264932
0.8547	High Similarity	NPC469393
0.8531	High Similarity	NPC174486
0.8523	High Similarity	NPC106700
0.8503	High Similarity	NPC243701
0.8497	Intermediate Similarity	NPC98667
0.8497	Intermediate Similarity	NPC232412
0.8497	Intermediate Similarity	NPC86809
0.8494	Intermediate Similarity	NPC210048
0.8494	Intermediate Similarity	NPC161650
0.8494	Intermediate Similarity	NPC201127
0.8488	Intermediate Similarity	NPC472620
0.848	Intermediate Similarity	NPC472619
0.848	Intermediate Similarity	NPC297195
0.848	Intermediate Similarity	NPC54903
0.848	Intermediate Similarity	NPC207574
0.848	Intermediate Similarity	NPC291795
0.848	Intermediate Similarity	NPC286074
0.8471	Intermediate Similarity	NPC17274
0.8471	Intermediate Similarity	NPC85047
0.8471	Intermediate Similarity	NPC120857
0.8471	Intermediate Similarity	NPC323137
0.8471	Intermediate Similarity	NPC475109
0.8466	Intermediate Similarity	NPC475656
0.8466	Intermediate Similarity	NPC475148
0.8434	Intermediate Similarity	NPC470352
0.8434	Intermediate Similarity	NPC470354
0.8434	Intermediate Similarity	NPC54830
0.8434	Intermediate Similarity	NPC56049
0.843	Intermediate Similarity	NPC251144
0.843	Intermediate Similarity	NPC241387
0.8427	Intermediate Similarity	NPC294863
0.8427	Intermediate Similarity	NPC282636
0.8412	Intermediate Similarity	NPC259007
0.8412	Intermediate Similarity	NPC204088
0.8412	Intermediate Similarity	NPC329215
0.8409	Intermediate Similarity	NPC208069
0.8405	Intermediate Similarity	NPC469932
0.8402	Intermediate Similarity	NPC473022
0.8395	Intermediate Similarity	NPC140120
0.8385	Intermediate Similarity	NPC71184
0.8385	Intermediate Similarity	NPC206212
0.8373	Intermediate Similarity	NPC476169
0.8373	Intermediate Similarity	NPC275575
0.8372	Intermediate Similarity	NPC20734
0.8365	Intermediate Similarity	NPC469818
0.8364	Intermediate Similarity	NPC470353
0.8364	Intermediate Similarity	NPC288534
0.8364	Intermediate Similarity	NPC142527
0.8363	Intermediate Similarity	NPC469394
0.8354	Intermediate Similarity	NPC476509
0.8354	Intermediate Similarity	NPC321387
0.8354	Intermediate Similarity	NPC327059
0.8354	Intermediate Similarity	NPC150928
0.8354	Intermediate Similarity	NPC158866
0.8353	Intermediate Similarity	NPC469395
0.8352	Intermediate Similarity	NPC244903
0.8352	Intermediate Similarity	NPC121888
0.8344	Intermediate Similarity	NPC161864
0.8344	Intermediate Similarity	NPC469933
0.8344	Intermediate Similarity	NPC208303
0.8344	Intermediate Similarity	NPC211811
0.8343	Intermediate Similarity	NPC312630
0.8343	Intermediate Similarity	NPC472346
0.8343	Intermediate Similarity	NPC324220
0.8343	Intermediate Similarity	NPC92589
0.8333	Intermediate Similarity	NPC470942
0.8333	Intermediate Similarity	NPC329678
0.8333	Intermediate Similarity	NPC473135
0.8333	Intermediate Similarity	NPC470676
0.8333	Intermediate Similarity	NPC82534
0.8333	Intermediate Similarity	NPC295436
0.8333	Intermediate Similarity	NPC181388
0.8333	Intermediate Similarity	NPC473132
0.8324	Intermediate Similarity	NPC101107
0.8324	Intermediate Similarity	NPC313717
0.8324	Intermediate Similarity	NPC315306
0.8323	Intermediate Similarity	NPC474609
0.8323	Intermediate Similarity	NPC474738
0.8323	Intermediate Similarity	NPC78554
0.8323	Intermediate Similarity	NPC321372
0.8323	Intermediate Similarity	NPC192587
0.8323	Intermediate Similarity	NPC469936
0.8323	Intermediate Similarity	NPC109967
0.8323	Intermediate Similarity	NPC129053
0.8323	Intermediate Similarity	NPC475797
0.8314	Intermediate Similarity	NPC286230
0.8314	Intermediate Similarity	NPC253730
0.8314	Intermediate Similarity	NPC472622
0.8314	Intermediate Similarity	NPC76647
0.8314	Intermediate Similarity	NPC478060
0.8314	Intermediate Similarity	NPC471975
0.8314	Intermediate Similarity	NPC470377
0.8314	Intermediate Similarity	NPC470374
0.8314	Intermediate Similarity	NPC478059
0.8314	Intermediate Similarity	NPC126204
0.8313	Intermediate Similarity	NPC236756
0.8313	Intermediate Similarity	NPC472799
0.8313	Intermediate Similarity	NPC471695
0.8313	Intermediate Similarity	NPC100134
0.8313	Intermediate Similarity	NPC311579
0.8313	Intermediate Similarity	NPC477669
0.8313	Intermediate Similarity	NPC470555
0.8313	Intermediate Similarity	NPC209760
0.8304	Intermediate Similarity	NPC316262
0.8304	Intermediate Similarity	NPC314653
0.8303	Intermediate Similarity	NPC305965
0.8302	Intermediate Similarity	NPC472343
0.8302	Intermediate Similarity	NPC19476
0.8302	Intermediate Similarity	NPC241975
0.8297	Intermediate Similarity	NPC314020
0.8295	Intermediate Similarity	NPC477683
0.8295	Intermediate Similarity	NPC477682
0.8295	Intermediate Similarity	NPC5671
0.8294	Intermediate Similarity	NPC219861
0.8293	Intermediate Similarity	NPC65775
0.8293	Intermediate Similarity	NPC10027
0.8293	Intermediate Similarity	NPC164205
0.8293	Intermediate Similarity	NPC104236
0.8293	Intermediate Similarity	NPC473978
0.8286	Intermediate Similarity	NPC245975
0.8284	Intermediate Similarity	NPC471973
0.8284	Intermediate Similarity	NPC121647
0.8284	Intermediate Similarity	NPC195136
0.8282	Intermediate Similarity	NPC297886
0.8282	Intermediate Similarity	NPC474108
0.8282	Intermediate Similarity	NPC177995
0.8282	Intermediate Similarity	NPC249942
0.8282	Intermediate Similarity	NPC180477
0.8276	Intermediate Similarity	NPC473113
0.8274	Intermediate Similarity	NPC324358
0.8274	Intermediate Similarity	NPC318527
0.8274	Intermediate Similarity	NPC218313
0.8274	Intermediate Similarity	NPC474637
0.8274	Intermediate Similarity	NPC322459
0.8274	Intermediate Similarity	NPC263483
0.8274	Intermediate Similarity	NPC474681
0.8274	Intermediate Similarity	NPC323627
0.8272	Intermediate Similarity	NPC1886
0.8272	Intermediate Similarity	NPC178627

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 NPC158329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	963
0.2-0.3	1880
0.3-0.4	2695
0.4-0.5	1964
0.5-0.6	884
0.6-0.7	283
0.7-0.8	132
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7411	Suspended
0.8161	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD3749	Approved
0.8049	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2533	Approved
0.8049	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD2534	Approved
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD3882	Suspended
0.7963	Intermediate Similarity	NPD2800	Approved
0.7941	Intermediate Similarity	NPD3817	Phase 2
0.7923	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD4380	Phase 2
0.7914	Intermediate Similarity	NPD3750	Approved
0.7901	Intermediate Similarity	NPD8434	Phase 2
0.7879	Intermediate Similarity	NPD6799	Approved
0.7877	Intermediate Similarity	NPD7808	Phase 3
0.7874	Intermediate Similarity	NPD6232	Discontinued
0.7861	Intermediate Similarity	NPD5494	Approved
0.7821	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7751	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5403	Approved
0.7733	Intermediate Similarity	NPD5402	Approved
0.7714	Intermediate Similarity	NPD6959	Discontinued
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1512	Approved
0.7674	Intermediate Similarity	NPD2801	Approved
0.7667	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7654	Intermediate Similarity	NPD7054	Approved
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6559	Discontinued
0.7619	Intermediate Similarity	NPD5401	Approved
0.7616	Intermediate Similarity	NPD1934	Approved
0.7614	Intermediate Similarity	NPD1247	Approved
0.7611	Intermediate Similarity	NPD7472	Approved
0.7611	Intermediate Similarity	NPD7074	Phase 3
0.7607	Intermediate Similarity	NPD3748	Approved
0.76	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6651	Approved
0.7576	Intermediate Similarity	NPD1549	Phase 2
0.7572	Intermediate Similarity	NPD1465	Phase 2
0.7571	Intermediate Similarity	NPD5710	Approved
0.7571	Intermediate Similarity	NPD5711	Approved
0.756	Intermediate Similarity	NPD1511	Approved
0.7541	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD8312	Approved
0.753	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6099	Approved
0.7455	Intermediate Similarity	NPD2796	Approved
0.7455	Intermediate Similarity	NPD6100	Approved
0.7433	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3926	Phase 2
0.7427	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD3751	Discontinued
0.7389	Intermediate Similarity	NPD2403	Approved
0.7378	Intermediate Similarity	NPD1607	Approved
0.7362	Intermediate Similarity	NPD1240	Approved
0.7346	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7874	Approved
0.7286	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4287	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7246	Intermediate Similarity	NPD1551	Phase 2
0.7245	Intermediate Similarity	NPD7698	Approved
0.7245	Intermediate Similarity	NPD7697	Approved
0.7245	Intermediate Similarity	NPD7696	Phase 3
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD3268	Approved
0.7236	Intermediate Similarity	NPD8151	Discontinued
0.7225	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8285	Discontinued
0.7213	Intermediate Similarity	NPD7228	Approved
0.7208	Intermediate Similarity	NPD7870	Phase 2
0.7208	Intermediate Similarity	NPD7871	Phase 2
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2344	Approved
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8366	Approved
0.7182	Intermediate Similarity	NPD3787	Discontinued
0.7179	Intermediate Similarity	NPD6777	Approved
0.7179	Intermediate Similarity	NPD6782	Approved
0.7179	Intermediate Similarity	NPD6776	Approved
0.7179	Intermediate Similarity	NPD6778	Approved
0.7179	Intermediate Similarity	NPD6781	Approved
0.7179	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD6780	Approved
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7286	Phase 2
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7199	Phase 2
0.712	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD37	Approved
0.7111	Intermediate Similarity	NPD6234	Discontinued
0.7104	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7095	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD4965	Approved
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7079	Intermediate Similarity	NPD7783	Phase 2
0.7079	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7801	Approved
0.7077	Intermediate Similarity	NPD7699	Phase 2
0.7077	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD7685	Pre-registration
0.7048	Intermediate Similarity	NPD8491	Approved
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5406	Approved
0.7041	Intermediate Similarity	NPD5404	Approved
0.7041	Intermediate Similarity	NPD5405	Approved
0.7041	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD4288	Approved
0.7035	Intermediate Similarity	NPD2309	Approved
0.703	Intermediate Similarity	NPD3764	Approved
0.7014	Intermediate Similarity	NPD8469	Approved
0.7011	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6534	Approved
0.701	Intermediate Similarity	NPD6535	Approved
0.7006	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD6585	Discontinued
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.6982	Remote Similarity	NPD4308	Phase 3
0.6977	Remote Similarity	NPD7003	Approved
0.6971	Remote Similarity	NPD5049	Phase 3
0.6968	Remote Similarity	NPD6764	Approved
0.6968	Remote Similarity	NPD6765	Approved
0.6946	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD943	Approved
0.694	Remote Similarity	NPD8127	Discontinued
0.6938	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7799	Discontinued
0.6933	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD3266	Approved
0.6933	Remote Similarity	NPD3267	Approved
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2798	Approved
0.6889	Remote Similarity	NPD5761	Phase 2
0.6889	Remote Similarity	NPD5760	Phase 2
0.6889	Remote Similarity	NPD8455	Phase 2
0.6882	Remote Similarity	NPD7033	Discontinued
0.6882	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7584	Approved
0.6879	Remote Similarity	NPD8166	Discontinued
0.6878	Remote Similarity	NPD7240	Approved
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5890	Approved
0.6872	Remote Similarity	NPD5889	Approved
0.6867	Remote Similarity	NPD4625	Phase 3
0.6859	Remote Similarity	NPD8407	Phase 2
0.6857	Remote Similarity	NPD7907	Approved
0.6857	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9717	Approved
0.685	Remote Similarity	NPD6823	Phase 2
0.6839	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD2354	Approved

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