NPASS Compound

Structure

CID120537 OpenBabel06191715472D 21 23 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 -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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.8660 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 19 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.928
LogD:	2.645
LogS:	-3.476
# Rotatable Bonds:	2
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	2.44
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	1.3287831279740203e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	90.37012481689453%
Volume Distribution (VD):	0.859
Pgp-substrate:	14.871370315551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.72
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.409
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	3.562
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.311
Skin Sensitization:	0.789
Carcinogencity:	0.047
Eye Corrosion:	0.159
Eye Irritation:	0.973
Respiratory Toxicity:	0.226

Download Data

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

Natural Product: NPC120537

Natural Product ID:	NPC120537
*Common Name:**	Getiacaulein
IUPAC Name:	2,8-dihydroxy-1,6-dimethoxyxanthen-9-one
Synonyms:	Getiacaulein
Standard InCHIKey:	WYOSCUWDVFHQFY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-10-4-3-8(16)15(20-2)13(10)14(12)18/h3-6,16-17H,1-2H3
SMILES:	COc1cc(O)c2c(c1)oc1c(c2=O)c(OC)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467590
PubChem CID:	5281634
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

*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
NPO2806	Gentiana nivalis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94333-4]
NPO6580	Smirnowia iranica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502308]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12960376]
NPO27608	Gentianopsis barbata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14558348]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18406151]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2166136]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26020634]
NPO27608	Gentianopsis barbata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2608753]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8229021]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2806	Gentiana nivalis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30732	Phlomis pungens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18740	Larrea divaricata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7431.1	Phlomis herba-venti subsp. pungens	Subspecies	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18740	Larrea divaricata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2806	Gentiana nivalis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2806	Gentiana nivalis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25088	Larrea tridentata	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5845	Nectandra elaiophora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7431.1	Phlomis herba-venti subsp. pungens	Subspecies	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4684	Derris ovalifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13472	Cotula cinerea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO917	Betula alleghaniensis	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6580	Smirnowia iranica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27608	Gentianopsis barbata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1873	Nectandra miranda	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2806	Gentiana nivalis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24485	Dendrilla rosea	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5
Others	6
Potency	26

Activity Type	# Activity
Cell Line	8
Individual Protein	20
Organism	2
Others	3
Protein Complex	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	56600.0	nM	PMID[501760]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	53200.0	nM	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	73.2	%	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	5.8	%	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	18.8	%	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	5.5	%	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	4.5	%	PMID[501760]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	6.0	%	PMID[501760]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	15848.9	nM	PMID[501761]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[501761]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	25118.9	nM	PMID[501761]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[501761]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	12589.3	nM	PMID[501761]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[501761]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[501761]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[501761]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[501761]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[501761]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[501761]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	19011.5	nM	PMID[501761]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[501761]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[501761]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	63095.7	nM	PMID[501761]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[501761]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[501761]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[501761]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[501761]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000	nM	Patent: US9114126 B2
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[501760]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	13091.8	nM	PMID[501761]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	22387.2	nM	PMID[501761]
NPT2	Others	Unspecified		Potency	n.a.	8199.5	nM	PMID[501761]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[501761]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[501761]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[501761]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000.0	nM	PMID[501762]

☑ 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 NPC120537 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	462
0.1-0.2	1978
0.2-0.3	5108
0.3-0.4	11555
0.4-0.5	5658
0.5-0.6	3782
0.6-0.7	5099
0.7-0.8	4798
0.8-0.85	2113
0.85-0.9	1191
0.9-0.95	667
0.95-1	286

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180234
1.0	High Similarity	NPC199100
0.9932	High Similarity	NPC206238
0.9932	High Similarity	NPC292214
0.9932	High Similarity	NPC167091
0.9932	High Similarity	NPC88645
0.9932	High Similarity	NPC271779
0.9863	High Similarity	NPC161277
0.9863	High Similarity	NPC39007
0.9863	High Similarity	NPC101996
0.9862	High Similarity	NPC61620
0.9862	High Similarity	NPC62042
0.9797	High Similarity	NPC235165
0.9797	High Similarity	NPC255106
0.9795	High Similarity	NPC251110
0.9795	High Similarity	NPC149614
0.9795	High Similarity	NPC117579
0.9795	High Similarity	NPC171010
0.9732	High Similarity	NPC472910
0.9732	High Similarity	NPC472913
0.9732	High Similarity	NPC48208
0.9732	High Similarity	NPC222814
0.9732	High Similarity	NPC99597
0.9732	High Similarity	NPC78225
0.9732	High Similarity	NPC474836
0.9732	High Similarity	NPC472914
0.9732	High Similarity	NPC210084
0.9732	High Similarity	NPC162869
0.9732	High Similarity	NPC474208
0.9732	High Similarity	NPC156057
0.9732	High Similarity	NPC245758
0.9732	High Similarity	NPC96167
0.9732	High Similarity	NPC472911
0.9732	High Similarity	NPC475267
0.973	High Similarity	NPC2928
0.9728	High Similarity	NPC239128
0.9728	High Similarity	NPC187498
0.9728	High Similarity	NPC222830
0.9728	High Similarity	NPC71334
0.9728	High Similarity	NPC83508
0.9728	High Similarity	NPC301323
0.9728	High Similarity	NPC188203
0.9728	High Similarity	NPC293183
0.9728	High Similarity	NPC156222
0.9728	High Similarity	NPC100887
0.9728	High Similarity	NPC256283
0.9728	High Similarity	NPC198826
0.9728	High Similarity	NPC120163
0.9728	High Similarity	NPC57030
0.9728	High Similarity	NPC212678
0.9728	High Similarity	NPC275836
0.9728	High Similarity	NPC131624
0.9728	High Similarity	NPC275722
0.9728	High Similarity	NPC25270
0.9728	High Similarity	NPC241498
0.9728	High Similarity	NPC162313
0.9726	High Similarity	NPC29231
0.9726	High Similarity	NPC248102
0.9726	High Similarity	NPC179183
0.9724	High Similarity	NPC276930
0.9664	High Similarity	NPC191146
0.9664	High Similarity	NPC472916
0.9664	High Similarity	NPC68093
0.9662	High Similarity	NPC69394
0.9662	High Similarity	NPC183878
0.9662	High Similarity	NPC22519
0.9662	High Similarity	NPC47781
0.9662	High Similarity	NPC145379
0.9662	High Similarity	NPC176775
0.9662	High Similarity	NPC274327
0.9662	High Similarity	NPC231018
0.9662	High Similarity	NPC160951
0.9662	High Similarity	NPC255350
0.966	High Similarity	NPC204515
0.9658	High Similarity	NPC200221
0.9658	High Similarity	NPC17286
0.9658	High Similarity	NPC216318
0.9658	High Similarity	NPC259713
0.9658	High Similarity	NPC294502
0.9658	High Similarity	NPC296197
0.9603	High Similarity	NPC263449
0.96	High Similarity	NPC262286
0.96	High Similarity	NPC36852
0.96	High Similarity	NPC300727
0.96	High Similarity	NPC469584
0.96	High Similarity	NPC241904
0.9597	High Similarity	NPC2476
0.9597	High Similarity	NPC37392
0.9597	High Similarity	NPC20830
0.9597	High Similarity	NPC183597
0.9597	High Similarity	NPC50715
0.9597	High Similarity	NPC227325
0.9597	High Similarity	NPC163780
0.9597	High Similarity	NPC196439
0.9597	High Similarity	NPC201136
0.9597	High Similarity	NPC256612
0.9597	High Similarity	NPC128863
0.9597	High Similarity	NPC44079
0.9597	High Similarity	NPC213622
0.9597	High Similarity	NPC146165
0.9597	High Similarity	NPC167815
0.9597	High Similarity	NPC92659
0.9597	High Similarity	NPC4455
0.9597	High Similarity	NPC201451
0.9597	High Similarity	NPC26227
0.9597	High Similarity	NPC472909
0.9597	High Similarity	NPC138360
0.9597	High Similarity	NPC280339
0.9595	High Similarity	NPC236637
0.9595	High Similarity	NPC302950
0.9595	High Similarity	NPC219582
0.9595	High Similarity	NPC142540
0.9592	High Similarity	NPC184136
0.9592	High Similarity	NPC306821
0.9592	High Similarity	NPC45873
0.9589	High Similarity	NPC43669
0.9589	High Similarity	NPC194856
0.9589	High Similarity	NPC287395
0.9589	High Similarity	NPC196277
0.9589	High Similarity	NPC272721
0.9589	High Similarity	NPC183655
0.9539	High Similarity	NPC308992
0.9539	High Similarity	NPC266314
0.9536	High Similarity	NPC95936
0.9536	High Similarity	NPC476242
0.9536	High Similarity	NPC152904
0.9536	High Similarity	NPC250214
0.9533	High Similarity	NPC98661
0.9533	High Similarity	NPC274730
0.9533	High Similarity	NPC43243
0.9533	High Similarity	NPC138243
0.9533	High Similarity	NPC245546
0.9533	High Similarity	NPC266960
0.9533	High Similarity	NPC49824
0.9533	High Similarity	NPC201837
0.9533	High Similarity	NPC247017
0.953	High Similarity	NPC75279
0.953	High Similarity	NPC18727
0.953	High Similarity	NPC472915
0.953	High Similarity	NPC276409
0.953	High Similarity	NPC250822
0.9527	High Similarity	NPC226973
0.9527	High Similarity	NPC31363
0.9527	High Similarity	NPC225731
0.9527	High Similarity	NPC208043
0.9527	High Similarity	NPC202157
0.9524	High Similarity	NPC287101
0.9524	High Similarity	NPC223579
0.9524	High Similarity	NPC183950
0.9524	High Similarity	NPC137062
0.9524	High Similarity	NPC52005
0.9521	High Similarity	NPC77378
0.9521	High Similarity	NPC207729
0.9521	High Similarity	NPC30647
0.9521	High Similarity	NPC61871
0.9521	High Similarity	NPC46941
0.9521	High Similarity	NPC275772
0.9521	High Similarity	NPC55557
0.9521	High Similarity	NPC239312
0.9521	High Similarity	NPC130230
0.9477	High Similarity	NPC83922
0.9477	High Similarity	NPC472448
0.9474	High Similarity	NPC228785
0.9474	High Similarity	NPC56085
0.9474	High Similarity	NPC139036
0.9474	High Similarity	NPC204290
0.9474	High Similarity	NPC14353
0.9474	High Similarity	NPC476980
0.947	High Similarity	NPC93376
0.947	High Similarity	NPC75215
0.947	High Similarity	NPC176665
0.947	High Similarity	NPC227192
0.947	High Similarity	NPC101830
0.947	High Similarity	NPC223787
0.947	High Similarity	NPC299520
0.947	High Similarity	NPC110070
0.947	High Similarity	NPC470402
0.947	High Similarity	NPC129684
0.947	High Similarity	NPC287979
0.947	High Similarity	NPC181960
0.947	High Similarity	NPC163524
0.947	High Similarity	NPC224137
0.947	High Similarity	NPC203891
0.947	High Similarity	NPC305663
0.947	High Similarity	NPC189179
0.9467	High Similarity	NPC208197
0.9467	High Similarity	NPC57674
0.9467	High Similarity	NPC152951
0.9467	High Similarity	NPC168247
0.9467	High Similarity	NPC113906
0.9467	High Similarity	NPC117992
0.9467	High Similarity	NPC230149
0.9463	High Similarity	NPC245382
0.9463	High Similarity	NPC35763
0.9463	High Similarity	NPC100263
0.9463	High Similarity	NPC301123
0.9463	High Similarity	NPC100971
0.9463	High Similarity	NPC216769
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC209487

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 NPC120537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	983
0.2-0.3	1848
0.3-0.4	2670
0.4-0.5	1719
0.5-0.6	963
0.6-0.7	360
0.7-0.8	110
0.8-0.85	29
0.85-0.9	17
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9662	High Similarity	NPD2801	Approved
0.9595	High Similarity	NPD1934	Approved
0.9315	High Similarity	NPD1511	Approved
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9189	High Similarity	NPD1512	Approved
0.9026	High Similarity	NPD3882	Suspended
0.8987	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8987	High Similarity	NPD6168	Clinical (unspecified phase)
0.8776	High Similarity	NPD1552	Clinical (unspecified phase)
0.8776	High Similarity	NPD1550	Clinical (unspecified phase)
0.8765	High Similarity	NPD7074	Phase 3
0.8758	High Similarity	NPD3818	Discontinued
0.8734	High Similarity	NPD5494	Approved
0.872	High Similarity	NPD4338	Clinical (unspecified phase)
0.8718	High Similarity	NPD3817	Phase 2
0.8716	High Similarity	NPD1549	Phase 2
0.8704	High Similarity	NPD7054	Approved
0.8662	High Similarity	NPD4868	Clinical (unspecified phase)
0.865	High Similarity	NPD7472	Approved
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8535	High Similarity	NPD1465	Phase 2
0.8514	High Similarity	NPD1510	Phase 2
0.8493	Intermediate Similarity	NPD943	Approved
0.8493	Intermediate Similarity	NPD1240	Approved
0.8485	Intermediate Similarity	NPD6797	Phase 2
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8434	Intermediate Similarity	NPD7251	Discontinued
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8383	Intermediate Similarity	NPD7808	Phase 3
0.8378	Intermediate Similarity	NPD1607	Approved
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1247	Approved
0.8302	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.8212	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD447	Suspended
0.8067	Intermediate Similarity	NPD230	Phase 1
0.8063	Intermediate Similarity	NPD7411	Suspended
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD919	Approved
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7935	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7785	Intermediate Similarity	NPD9494	Approved
0.7764	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1933	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7702	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD2533	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6100	Approved
0.7628	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3226	Approved
0.7596	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1243	Approved
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD3748	Approved
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.745	Intermediate Similarity	NPD9269	Phase 2
0.7436	Intermediate Similarity	NPD6651	Approved
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7365	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7345	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7283	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5710	Approved
0.7225	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.719	Intermediate Similarity	NPD1470	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7181	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD411	Approved
0.7176	Intermediate Similarity	NPD5353	Approved
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD17	Approved
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7121	Intermediate Similarity	NPD2899	Discontinued
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7105	Intermediate Similarity	NPD1481	Phase 2
0.7103	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7097	Intermediate Similarity	NPD3018	Phase 2
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD4749	Approved
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD2654	Approved
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD1535	Discovery
0.7037	Intermediate Similarity	NPD1471	Phase 3
0.7029	Intermediate Similarity	NPD7229	Phase 3
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7016	Intermediate Similarity	NPD7698	Approved
0.7013	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD4287	Approved
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9545	Approved
0.6995	Remote Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD2424	Discontinued
0.6981	Remote Similarity	NPD1558	Phase 1
0.698	Remote Similarity	NPD9493	Approved
0.6979	Remote Similarity	NPD7871	Phase 2
0.6979	Remote Similarity	NPD7870	Phase 2

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