NPASS Compound

Structure

CID119224 OpenBabel06191715472D 34 36 0 0 0 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 23 2 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 28 2 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.22
Volume:	493.551
LogP:	7.581
LogD:	3.251
LogS:	-2.754
# Rotatable Bonds:	6
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.194
Synthetic Accessibility Score:	3.452
Fsp3:	0.321
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	1.0626624316500966e-05
Pgp-inhibitor:	0.381
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.529
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	78.72454071044922%
Volume Distribution (VD):	1.552
Pgp-substrate:	22.044588088989258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.229
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.499
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.125
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	8.116
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.928
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.438
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC119224

Natural Product ID:	NPC119224
*Common Name:**	Garcinone E
IUPAC Name:	2,3,6,8-tetrahydroxy-1,4,7-tris(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Garcinone E
Standard InCHIKey:	WVJYEKGQSBGNRP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H32O6/c1-14(2)7-10-17-20(29)13-21-23(24(17)30)27(33)22-18(11-8-15(3)4)25(31)26(32)19(28(22)34-21)12-9-16(5)6/h7-9,13,29-32H,10-12H2,1-6H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c1c(CC=C(C)C)c(c(c(CC=C(C)C)c1o2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454580
PubChem CID:	10298511
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:0003519] 8-prenylated xanthones

*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
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(74)80113-5]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10361686]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724839]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113969]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296616]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	leaves	Bobai, Guangxi Province, China	2005-Dec	PMID[24679044]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	Barks	n.a.	n.a.	PMID[24754786]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9298	Piper wightii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26341	Trifolium resupinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2812	Lecanora kukunorensis	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6948	Davidsoniella virescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10228	Ascochyta viciae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15242	Setosphaeria holmii	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1154	Neomeris annulata	Species	Dasycladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	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	4
IC50	13
Others	4
Potency	47

Activity Type	# Activity
Cell Line	8
Individual Protein	40
Organism	4
Others	12
PROTEIN COMPLEX	3
PROTEIN-PROTEIN INTERACTION	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	15000.0	nM	PMID[456410]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	23.9	%	PMID[456411]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	25100.0	nM	PMID[456411]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	32.3	%	PMID[456411]
NPT134	Cell Line	SK-BR-3	Homo sapiens	Survival	=	52.3	%	PMID[456411]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[456412]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[456414]
NPT1387	Individual Protein	Genome polyprotein	Hepatitis C virus	IC50	>	49751.0	nM	PMID[456414]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[456414]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[456414]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[456414]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	19952.6	nM	PMID[456414]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	17740.7	nM	PMID[456414]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	14125.4	nM	PMID[456414]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	828.0	nM	PMID[456414]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	28183.8	nM	PMID[456414]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	19952.6	nM	PMID[456414]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	44668.4	nM	PMID[456414]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[456414]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[456414]
NPT2892	Individual Protein	X-box-binding protein 1	Homo sapiens	IC50	=	5240.0	nM	PMID[456414]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	6768.81	nM	PMID[456414]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	4649.0	nM	PMID[456414]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[456414]
NPT2893	Individual Protein	DNA damage-inducible transcript 3 protein	Mus musculus	IC50	>	9670.0	nM	PMID[456414]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	32629.4	nM	PMID[456414]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	=	4780.0	nM	PMID[456414]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	20000.0	nM	PMID[456414]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[456414]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[456414]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[456414]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[456414]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[456414]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	16833.6	nM	PMID[456414]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[456414]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[456414]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[456414]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[456414]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[456414]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[456414]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[456414]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[456414]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[456414]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	2.8	ug.mL-1	PMID[456412]
NPT2	Others	Unspecified		Ratio IC50	=	0.54	n.a.	PMID[456412]
NPT865	Individual Protein	Fatty acid synthase	Homo sapiens	IC50	=	3300.0	nM	PMID[456413]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3017.0	nM	PMID[456414]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	813.0	nM	PMID[456414]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	23280.9	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[456414]
NPT2	Others	Unspecified		IC50	=	3460.0	nM	PMID[456414]
NPT2	Others	Unspecified		IC50	=	2790.0	nM	PMID[456414]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[456414]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[456414]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[456414]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[456414]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[456414]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	23109.3	nM	PMID[456414]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[456414]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[456414]

☑ 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 NPC119224 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	455
0.1-0.2	1954
0.2-0.3	4490
0.3-0.4	11277
0.4-0.5	6738
0.5-0.6	3655
0.6-0.7	5088
0.7-0.8	5236
0.8-0.85	2240
0.85-0.9	1206
0.9-0.95	307
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC236796
0.9805	High Similarity	NPC236132
0.9801	High Similarity	NPC142339
0.974	High Similarity	NPC470694
0.9739	High Similarity	NPC320359
0.9677	High Similarity	NPC207690
0.9675	High Similarity	NPC40491
0.9675	High Similarity	NPC278052
0.9673	High Similarity	NPC100123
0.9669	High Similarity	NPC89474
0.961	High Similarity	NPC56085
0.961	High Similarity	NPC235018
0.961	High Similarity	NPC228785
0.961	High Similarity	NPC14353
0.961	High Similarity	NPC45146
0.9554	High Similarity	NPC37870
0.9551	High Similarity	NPC7483
0.9551	High Similarity	NPC270837
0.9548	High Similarity	NPC61010
0.9548	High Similarity	NPC32694
0.9548	High Similarity	NPC278427
0.9545	High Similarity	NPC85121
0.9542	High Similarity	NPC274730
0.9536	High Similarity	NPC202157
0.9487	High Similarity	NPC294965
0.9487	High Similarity	NPC25152
0.9487	High Similarity	NPC329760
0.9484	High Similarity	NPC475886
0.9484	High Similarity	NPC80375
0.9484	High Similarity	NPC474287
0.9481	High Similarity	NPC241904
0.9481	High Similarity	NPC165977
0.9481	High Similarity	NPC300727
0.9481	High Similarity	NPC217677
0.9477	High Similarity	NPC113906
0.9474	High Similarity	NPC249570
0.943	High Similarity	NPC39091
0.9427	High Similarity	NPC152659
0.9427	High Similarity	NPC220313
0.9427	High Similarity	NPC189473
0.9427	High Similarity	NPC23298
0.9427	High Similarity	NPC248638
0.9427	High Similarity	NPC197168
0.9427	High Similarity	NPC236521
0.9423	High Similarity	NPC474351
0.9423	High Similarity	NPC475883
0.9423	High Similarity	NPC474187
0.9423	High Similarity	NPC66288
0.9423	High Similarity	NPC474186
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC185258
0.9419	High Similarity	NPC476242
0.9419	High Similarity	NPC329091
0.9419	High Similarity	NPC172770
0.9416	High Similarity	NPC475799
0.9416	High Similarity	NPC138243
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC13779
0.9416	High Similarity	NPC68093
0.9412	High Similarity	NPC476631
0.9367	High Similarity	NPC473286
0.9367	High Similarity	NPC239752
0.9367	High Similarity	NPC275780
0.9367	High Similarity	NPC472450
0.9367	High Similarity	NPC326520
0.9367	High Similarity	NPC25361
0.9359	High Similarity	NPC200746
0.9359	High Similarity	NPC321399
0.9355	High Similarity	NPC79053
0.9355	High Similarity	NPC136674
0.9355	High Similarity	NPC273843
0.9355	High Similarity	NPC262286
0.9355	High Similarity	NPC36852
0.9355	High Similarity	NPC78225
0.9342	High Similarity	NPC227122
0.9308	High Similarity	NPC472449
0.9308	High Similarity	NPC170245
0.9304	High Similarity	NPC146134
0.9299	High Similarity	NPC472275
0.9295	High Similarity	NPC235448
0.9286	High Similarity	NPC298692
0.925	High Similarity	NPC126204
0.925	High Similarity	NPC117854
0.925	High Similarity	NPC6588
0.925	High Similarity	NPC477154
0.925	High Similarity	NPC218226
0.9245	High Similarity	NPC156432
0.9241	High Similarity	NPC229632
0.9241	High Similarity	NPC211107
0.9241	High Similarity	NPC201800
0.9236	High Similarity	NPC84571
0.9236	High Similarity	NPC471973
0.9236	High Similarity	NPC139036
0.9236	High Similarity	NPC36217
0.9236	High Similarity	NPC204290
0.9231	High Similarity	NPC223787
0.9231	High Similarity	NPC218871
0.9231	High Similarity	NPC469584
0.9231	High Similarity	NPC476630
0.9226	High Similarity	NPC67396
0.9221	High Similarity	NPC106976
0.9216	High Similarity	NPC151473
0.9216	High Similarity	NPC62042
0.9216	High Similarity	NPC88804
0.9216	High Similarity	NPC3825
0.9211	High Similarity	NPC194856
0.9211	High Similarity	NPC276930
0.9202	High Similarity	NPC227906
0.9198	High Similarity	NPC158226
0.9193	High Similarity	NPC476637
0.9193	High Similarity	NPC163130
0.9193	High Similarity	NPC165979
0.9187	High Similarity	NPC43319
0.9182	High Similarity	NPC473313
0.9182	High Similarity	NPC472278
0.9182	High Similarity	NPC41301
0.9182	High Similarity	NPC329669
0.9182	High Similarity	NPC474350
0.9182	High Similarity	NPC475985
0.9177	High Similarity	NPC167678
0.9177	High Similarity	NPC29876
0.9177	High Similarity	NPC311740
0.9177	High Similarity	NPC266314
0.9172	High Similarity	NPC95936
0.9172	High Similarity	NPC250214
0.9172	High Similarity	NPC474290
0.9172	High Similarity	NPC469658
0.9167	High Similarity	NPC209614
0.9167	High Similarity	NPC472907
0.9167	High Similarity	NPC470328
0.9167	High Similarity	NPC472626
0.9167	High Similarity	NPC24640
0.9167	High Similarity	NPC276444
0.9161	High Similarity	NPC280530
0.9161	High Similarity	NPC227337
0.9161	High Similarity	NPC273462
0.9161	High Similarity	NPC49402
0.9161	High Similarity	NPC93552
0.9161	High Similarity	NPC213896
0.9161	High Similarity	NPC95842
0.9161	High Similarity	NPC70433
0.9161	High Similarity	NPC135522
0.9161	High Similarity	NPC33051
0.9161	High Similarity	NPC192083
0.9161	High Similarity	NPC178964
0.9161	High Similarity	NPC107109
0.9161	High Similarity	NPC74924
0.9156	High Similarity	NPC205046
0.9156	High Similarity	NPC59162
0.9156	High Similarity	NPC304295
0.915	High Similarity	NPC223988
0.9145	High Similarity	NPC207729
0.9136	High Similarity	NPC109827
0.9136	High Similarity	NPC124470
0.913	High Similarity	NPC474024
0.9125	High Similarity	NPC37183
0.9125	High Similarity	NPC293319
0.9125	High Similarity	NPC475888
0.9119	High Similarity	NPC52204
0.9119	High Similarity	NPC83922
0.9119	High Similarity	NPC472448
0.9114	High Similarity	NPC299436
0.9114	High Similarity	NPC476980
0.9114	High Similarity	NPC246478
0.9108	High Similarity	NPC472910
0.9108	High Similarity	NPC199463
0.9108	High Similarity	NPC48208
0.9108	High Similarity	NPC474208
0.9108	High Similarity	NPC474836
0.9108	High Similarity	NPC96167
0.9108	High Similarity	NPC472913
0.9108	High Similarity	NPC472914
0.9108	High Similarity	NPC156057
0.9108	High Similarity	NPC245758
0.9108	High Similarity	NPC187745
0.9108	High Similarity	NPC162869
0.9108	High Similarity	NPC37543
0.9108	High Similarity	NPC472911
0.9108	High Similarity	NPC161960
0.9108	High Similarity	NPC475267
0.9108	High Similarity	NPC304008
0.9108	High Similarity	NPC222814
0.9108	High Similarity	NPC472963
0.9103	High Similarity	NPC152951
0.9103	High Similarity	NPC57674
0.9103	High Similarity	NPC117992
0.9103	High Similarity	NPC200761
0.9103	High Similarity	NPC470327
0.9103	High Similarity	NPC230149
0.9103	High Similarity	NPC45849
0.9103	High Similarity	NPC168247
0.9103	High Similarity	NPC477503
0.9103	High Similarity	NPC321779
0.9097	High Similarity	NPC37684
0.9097	High Similarity	NPC157784
0.9097	High Similarity	NPC63187
0.9097	High Similarity	NPC101996
0.9097	High Similarity	NPC471982
0.9097	High Similarity	NPC199100
0.9097	High Similarity	NPC180234

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 NPC119224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	1029
0.2-0.3	1774
0.3-0.4	2746
0.4-0.5	1736
0.5-0.6	936
0.6-0.7	341
0.7-0.8	133
0.8-0.85	31
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD2393	Clinical (unspecified phase)
0.9038	High Similarity	NPD2801	Approved
0.8854	High Similarity	NPD1934	Approved
0.8824	High Similarity	NPD1511	Approved
0.872	High Similarity	NPD7473	Discontinued
0.871	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD6232	Discontinued
0.8589	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD7819	Suspended
0.8528	High Similarity	NPD5494	Approved
0.8526	High Similarity	NPD4378	Clinical (unspecified phase)
0.8503	High Similarity	NPD5844	Phase 1
0.8457	Intermediate Similarity	NPD3882	Suspended
0.8434	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6166	Phase 2
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD1465	Phase 2
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8291	Intermediate Similarity	NPD2534	Approved
0.8291	Intermediate Similarity	NPD2533	Approved
0.8291	Intermediate Similarity	NPD2532	Approved
0.8284	Intermediate Similarity	NPD7054	Approved
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4380	Phase 2
0.8235	Intermediate Similarity	NPD7472	Approved
0.8225	Intermediate Similarity	NPD3818	Discontinued
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD1549	Phase 2
0.814	Intermediate Similarity	NPD7251	Discontinued
0.8129	Intermediate Similarity	NPD6099	Approved
0.8129	Intermediate Similarity	NPD6100	Approved
0.8089	Intermediate Similarity	NPD2800	Approved
0.8086	Intermediate Similarity	NPD3226	Approved
0.8081	Intermediate Similarity	NPD6797	Phase 2
0.8077	Intermediate Similarity	NPD2346	Discontinued
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD943	Approved
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7989	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD7411	Suspended
0.7965	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3749	Approved
0.7949	Intermediate Similarity	NPD1510	Phase 2
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7925	Intermediate Similarity	NPD3750	Approved
0.7922	Intermediate Similarity	NPD1240	Approved
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7898	Intermediate Similarity	NPD2796	Approved
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6801	Discontinued
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD1247	Approved
0.7812	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5711	Approved
0.7738	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4625	Phase 3
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD3926	Phase 2
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD2799	Discontinued
0.76	Intermediate Similarity	NPD7228	Approved
0.7595	Intermediate Similarity	NPD6651	Approved
0.758	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7531	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7783	Phase 2
0.7423	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD447	Suspended
0.7421	Intermediate Similarity	NPD7698	Approved
0.7421	Intermediate Similarity	NPD7696	Phase 3
0.7421	Intermediate Similarity	NPD7697	Approved
0.7414	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7870	Phase 2
0.7382	Intermediate Similarity	NPD7871	Phase 2
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7355	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD5404	Approved
0.7346	Intermediate Similarity	NPD5405	Approved
0.7346	Intermediate Similarity	NPD5406	Approved
0.7346	Intermediate Similarity	NPD5408	Approved
0.7342	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2309	Approved
0.733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.7321	Intermediate Similarity	NPD5403	Approved
0.7321	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1201	Approved
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7245	Intermediate Similarity	NPD7801	Approved
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7212	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5401	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7186	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD6696	Suspended
0.7176	Intermediate Similarity	NPD1653	Approved
0.7169	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD9269	Phase 2
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD1203	Approved
0.7126	Intermediate Similarity	NPD6190	Approved
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7099	Intermediate Similarity	NPD1933	Approved
0.7097	Intermediate Similarity	NPD1610	Phase 2
0.7089	Intermediate Similarity	NPD2798	Approved
0.7083	Intermediate Similarity	NPD3300	Phase 2
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.7066	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD4287	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD7685	Pre-registration
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7044	Intermediate Similarity	NPD9494	Approved
0.7037	Intermediate Similarity	NPD6213	Phase 3
0.7037	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6212	Phase 3
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7029	Intermediate Similarity	NPD4288	Approved
0.7027	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2797	Approved
0.7019	Intermediate Similarity	NPD411	Approved
0.7019	Intermediate Similarity	NPD3764	Approved
0.7017	Intermediate Similarity	NPD7177	Discontinued
0.7016	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2403	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