NPASS Compound

Structure

CID275780 OpenBabel06191716082D 30 33 0 0 0 0 0 0 0 0999 V2000 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 6.0622 -4.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 4.3301 -0.5000 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 4.3301 -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 1.7321 -2.0000 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 6.0622 -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 6.9282 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 24 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.16
Volume:	418.447
LogP:	5.902
LogD:	4.037
LogS:	-3.148
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	3.416
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	1.4278266462497413e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.199
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.52622985839844%
Volume Distribution (VD):	0.446
Pgp-substrate:	4.720791339874268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.593
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.788
CYP2D6-substrate:	0.537
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	1.402
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.437
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.806
Carcinogencity:	0.781
Eye Corrosion:	0.004
Eye Irritation:	0.516
Respiratory Toxicity:	0.722

Download Data

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

Natural Product: NPC275780

Natural Product ID:	NPC275780
*Common Name:**	Mangostanin
IUPAC Name:	5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Synonyms:	9-Hydroxycalabaxanthone; Mangostanin
Standard InCHIKey:	HQWHKELJHUFLGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H24O6/c1-12(2)6-7-14-19-17(10-15(25)23(14)28-5)29-18-11-16-13(8-9-24(3,4)30-16)21(26)20(18)22(19)27/h6,8-11,25-26H,7H2,1-5H3
SMILES:	COc1c(O)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc2c(c1O)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561643
PubChem CID:	5495929
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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
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]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296616]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
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]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
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]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO40853	Garcinia tetrandra	Species	Clusiaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[30978023]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
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.	Database[FooDB]
NPO25472	Garcinia cowa	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]
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[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	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]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	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]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	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
ED50	1
IC50	20
Ki	1
MIC	6
Others	5

Activity Type	# Activity
Cell Line	11
CELL-LINE	1
Individual Protein	9
NON-MOLECULAR	1
Organism	7
Others	3
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[483310]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.1	uM	PMID[483311]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[483311]
NPT3892	Individual Protein	Tumor necrosis factor receptor superfamily member 10B	Homo sapiens	FC	=	4.0	n.a.	PMID[483312]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	20100.0	nM	PMID[483313]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	5900.0	nM	PMID[483313]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	19690.0	nM	PMID[483315]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	21060.0	nM	PMID[483315]
NPT2297	Cell Line	ASPC1	Homo sapiens	IC50	=	25490.0	nM	PMID[483315]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	26140.0	nM	PMID[483315]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1600.0	nM	PMID[483318]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3400.0	nM	PMID[483318]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1900.0	nM	PMID[483318]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1700.0	nM	PMID[483318]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18600.0	nM	PMID[483319]
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	420.0	nM	PMID[483320]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	1.9	ug.mL-1	PMID[483310]
NPT2	Others	Unspecified		Ratio IC50	=	2.05	n.a.	PMID[483310]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[483311]
NPT865	Individual Protein	Fatty acid synthase	Homo sapiens	IC50	=	40640.0	nM	PMID[483314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26170.0	nM	PMID[483315]
NPT2	Others	Unspecified		Inhibition	=	70.1	%	PMID[483316]
NPT2	Others	Unspecified		IC50	=	34600.0	nM	PMID[483316]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[483316]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[483316]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[483316]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[483316]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[483316]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[483316]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	98.7	%	PMID[483317]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	108.7	%	PMID[483317]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	IC50	=	1900.0	nM	PMID[483318]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	=	11400.0	nM	PMID[483319]

☑ 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 NPC275780 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	459
0.1-0.2	1844
0.2-0.3	4274
0.3-0.4	10849
0.4-0.5	7223
0.5-0.6	3545
0.6-0.7	5021
0.7-0.8	5015
0.8-0.85	2518
0.85-0.9	1242
0.9-0.95	615
0.95-1	92

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472450
1.0	High Similarity	NPC239752
0.9936	High Similarity	NPC39091
0.9935	High Similarity	NPC189473
0.9935	High Similarity	NPC23298
0.9871	High Similarity	NPC229632
0.9809	High Similarity	NPC37870
0.9809	High Similarity	NPC472449
0.9808	High Similarity	NPC248638
0.9808	High Similarity	NPC152659
0.9808	High Similarity	NPC236521
0.9806	High Similarity	NPC61010
0.9744	High Similarity	NPC329760
0.9744	High Similarity	NPC83922
0.9744	High Similarity	NPC25152
0.9744	High Similarity	NPC472448
0.9742	High Similarity	NPC228785
0.9742	High Similarity	NPC139036
0.9742	High Similarity	NPC471973
0.9742	High Similarity	NPC56085
0.9742	High Similarity	NPC14353
0.9742	High Similarity	NPC204290
0.9682	High Similarity	NPC186686
0.9682	High Similarity	NPC207690
0.9682	High Similarity	NPC220313
0.9679	High Similarity	NPC167678
0.9679	High Similarity	NPC40491
0.9679	High Similarity	NPC29876
0.9679	High Similarity	NPC278052
0.9677	High Similarity	NPC100123
0.9677	High Similarity	NPC474290
0.9677	High Similarity	NPC476242
0.9623	High Similarity	NPC477154
0.9623	High Similarity	NPC6588
0.9623	High Similarity	NPC117854
0.9618	High Similarity	NPC474150
0.9618	High Similarity	NPC474162
0.9615	High Similarity	NPC200746
0.9615	High Similarity	NPC320359
0.9615	High Similarity	NPC476980
0.9613	High Similarity	NPC300727
0.9613	High Similarity	NPC78225
0.9613	High Similarity	NPC217677
0.9613	High Similarity	NPC136674
0.9613	High Similarity	NPC165977
0.9613	High Similarity	NPC241904
0.956	High Similarity	NPC170245
0.956	High Similarity	NPC43319
0.9557	High Similarity	NPC7483
0.9557	High Similarity	NPC270837
0.9557	High Similarity	NPC306321
0.9557	High Similarity	NPC146134
0.9557	High Similarity	NPC303460
0.9557	High Similarity	NPC236132
0.9554	High Similarity	NPC474187
0.9554	High Similarity	NPC32694
0.9554	High Similarity	NPC259456
0.9551	High Similarity	NPC204879
0.9548	High Similarity	NPC191146
0.9548	High Similarity	NPC68093
0.9548	High Similarity	NPC274730
0.9548	High Similarity	NPC142339
0.95	High Similarity	NPC218226
0.9497	High Similarity	NPC326520
0.9497	High Similarity	NPC293319
0.9494	High Similarity	NPC261470
0.9494	High Similarity	NPC52204
0.9494	High Similarity	NPC294965
0.949	High Similarity	NPC474960
0.949	High Similarity	NPC119209
0.949	High Similarity	NPC235018
0.949	High Similarity	NPC80375
0.949	High Similarity	NPC45146
0.949	High Similarity	NPC36217
0.949	High Similarity	NPC474287
0.949	High Similarity	NPC475886
0.949	High Similarity	NPC192686
0.949	High Similarity	NPC118256
0.9487	High Similarity	NPC474681
0.9487	High Similarity	NPC236796
0.9487	High Similarity	NPC476981
0.9487	High Similarity	NPC36852
0.9487	High Similarity	NPC218313
0.9487	High Similarity	NPC262286
0.9441	High Similarity	NPC476637
0.9437	High Similarity	NPC120593
0.9434	High Similarity	NPC475985
0.9434	High Similarity	NPC41301
0.943	High Similarity	NPC474351
0.943	High Similarity	NPC66288
0.943	High Similarity	NPC475883
0.943	High Similarity	NPC258331
0.943	High Similarity	NPC474038
0.943	High Similarity	NPC474186
0.943	High Similarity	NPC57715
0.943	High Similarity	NPC266314
0.943	High Similarity	NPC234644
0.9427	High Similarity	NPC250214
0.9427	High Similarity	NPC235448
0.9427	High Similarity	NPC95936
0.9423	High Similarity	NPC5322
0.9423	High Similarity	NPC472455
0.9423	High Similarity	NPC471985
0.9423	High Similarity	NPC276444
0.9423	High Similarity	NPC133970
0.9423	High Similarity	NPC138243
0.9423	High Similarity	NPC6633
0.9419	High Similarity	NPC89474
0.9419	High Similarity	NPC69394
0.9419	High Similarity	NPC183878
0.9419	High Similarity	NPC145379
0.9419	High Similarity	NPC255350
0.9419	High Similarity	NPC178964
0.9419	High Similarity	NPC47781
0.9419	High Similarity	NPC22519
0.9419	High Similarity	NPC176775
0.9419	High Similarity	NPC274327
0.9419	High Similarity	NPC160951
0.9419	High Similarity	NPC280530
0.9419	High Similarity	NPC231018
0.9419	High Similarity	NPC95842
0.9387	High Similarity	NPC310794
0.9383	High Similarity	NPC472276
0.9383	High Similarity	NPC101107
0.9379	High Similarity	NPC126204
0.9375	High Similarity	NPC50960
0.9375	High Similarity	NPC224280
0.9375	High Similarity	NPC62261
0.9375	High Similarity	NPC303174
0.9375	High Similarity	NPC156432
0.9371	High Similarity	NPC201800
0.9371	High Similarity	NPC472402
0.9367	High Similarity	NPC188433
0.9367	High Similarity	NPC475784
0.9367	High Similarity	NPC119224
0.9367	High Similarity	NPC246478
0.9363	High Similarity	NPC245758
0.9363	High Similarity	NPC96167
0.9363	High Similarity	NPC472914
0.9363	High Similarity	NPC52889
0.9363	High Similarity	NPC469584
0.9363	High Similarity	NPC162869
0.9363	High Similarity	NPC472911
0.9363	High Similarity	NPC156057
0.9363	High Similarity	NPC27337
0.9363	High Similarity	NPC222814
0.9363	High Similarity	NPC472963
0.9363	High Similarity	NPC472913
0.9363	High Similarity	NPC218871
0.9363	High Similarity	NPC476630
0.9363	High Similarity	NPC475267
0.9363	High Similarity	NPC474208
0.9363	High Similarity	NPC472910
0.9363	High Similarity	NPC48208
0.9363	High Similarity	NPC284820
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC473272
0.9363	High Similarity	NPC474836
0.9359	High Similarity	NPC20830
0.9359	High Similarity	NPC183597
0.9359	High Similarity	NPC196439
0.9359	High Similarity	NPC167815
0.9359	High Similarity	NPC256612
0.9359	High Similarity	NPC146165
0.9359	High Similarity	NPC234255
0.9359	High Similarity	NPC117992
0.9359	High Similarity	NPC163780
0.9359	High Similarity	NPC168247
0.9359	High Similarity	NPC50715
0.9359	High Similarity	NPC113906
0.9359	High Similarity	NPC128863
0.9359	High Similarity	NPC2476
0.9359	High Similarity	NPC200246
0.9359	High Similarity	NPC201136
0.9359	High Similarity	NPC472280
0.9359	High Similarity	NPC152951
0.9359	High Similarity	NPC4455
0.9359	High Similarity	NPC138360
0.9359	High Similarity	NPC280339
0.9359	High Similarity	NPC57674
0.9359	High Similarity	NPC213622
0.9359	High Similarity	NPC230149
0.9359	High Similarity	NPC256925
0.9359	High Similarity	NPC92659
0.9359	High Similarity	NPC227325
0.9355	High Similarity	NPC275836
0.9355	High Similarity	NPC239128
0.9355	High Similarity	NPC212678
0.9355	High Similarity	NPC199100
0.9355	High Similarity	NPC57030
0.9355	High Similarity	NPC25270
0.9355	High Similarity	NPC83508
0.9355	High Similarity	NPC471982
0.9355	High Similarity	NPC100887
0.9355	High Similarity	NPC156222
0.9355	High Similarity	NPC301323
0.9355	High Similarity	NPC187498
0.9355	High Similarity	NPC71334
0.9355	High Similarity	NPC180234
0.9355	High Similarity	NPC131624

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 NPC275780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	982
0.2-0.3	1774
0.3-0.4	2689
0.4-0.5	1788
0.5-0.6	920
0.6-0.7	419
0.7-0.8	129
0.8-0.85	30
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD2801	Approved
0.9172	High Similarity	NPD2393	Clinical (unspecified phase)
0.9108	High Similarity	NPD1934	Approved
0.8889	High Similarity	NPD5494	Approved
0.8839	High Similarity	NPD1511	Approved
0.8788	High Similarity	NPD6167	Clinical (unspecified phase)
0.8788	High Similarity	NPD6166	Phase 2
0.8788	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD1512	Approved
0.8704	High Similarity	NPD3882	Suspended
0.8667	High Similarity	NPD6232	Discontinued
0.8662	High Similarity	NPD4378	Clinical (unspecified phase)
0.8647	High Similarity	NPD4338	Clinical (unspecified phase)
0.8631	High Similarity	NPD7054	Approved
0.8631	High Similarity	NPD5844	Phase 1
0.8625	High Similarity	NPD4380	Phase 2
0.8623	High Similarity	NPD7473	Discontinued
0.858	High Similarity	NPD7074	Phase 3
0.858	High Similarity	NPD7472	Approved
0.8571	High Similarity	NPD3818	Discontinued
0.8528	High Similarity	NPD3817	Phase 2
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7819	Suspended
0.8466	Intermediate Similarity	NPD1465	Phase 2
0.8428	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6797	Phase 2
0.8383	Intermediate Similarity	NPD6959	Discontinued
0.8372	Intermediate Similarity	NPD7251	Discontinued
0.8324	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD1247	Approved
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD3749	Approved
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8084	Intermediate Similarity	NPD5402	Approved
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8063	Intermediate Similarity	NPD3750	Approved
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7925	Intermediate Similarity	NPD2935	Discontinued
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6799	Approved
0.7888	Intermediate Similarity	NPD2800	Approved
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.7849	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1607	Approved
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.7836	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3787	Discontinued
0.7784	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2346	Discontinued
0.775	Intermediate Similarity	NPD3748	Approved
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6234	Discontinued
0.7722	Intermediate Similarity	NPD1613	Approved
0.7722	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6099	Approved
0.7702	Intermediate Similarity	NPD6100	Approved
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7665	Intermediate Similarity	NPD5403	Approved
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.7644	Intermediate Similarity	NPD7199	Phase 2
0.7627	Intermediate Similarity	NPD7228	Approved
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7562	Intermediate Similarity	NPD447	Suspended
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5401	Approved
0.7544	Intermediate Similarity	NPD37	Approved
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.7455	Intermediate Similarity	NPD1243	Approved
0.7449	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7783	Phase 2
0.7448	Intermediate Similarity	NPD7697	Approved
0.7448	Intermediate Similarity	NPD7698	Approved
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2344	Approved
0.741	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7407	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7396	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD4360	Phase 2
0.7394	Intermediate Similarity	NPD4363	Phase 3
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6190	Approved
0.7358	Intermediate Similarity	NPD4908	Phase 1
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD1933	Approved
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD9494	Approved
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD7801	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7584	Approved
0.7241	Intermediate Similarity	NPD6844	Discontinued
0.7228	Intermediate Similarity	NPD7549	Discontinued
0.7225	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4287	Approved
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.7174	Intermediate Similarity	NPD7240	Approved
0.717	Intermediate Similarity	NPD1470	Approved
0.7169	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD5406	Approved
0.7169	Intermediate Similarity	NPD5404	Approved
0.7169	Intermediate Similarity	NPD5408	Approved
0.7167	Intermediate Similarity	NPD5242	Approved
0.7165	Intermediate Similarity	NPD2493	Approved
0.7165	Intermediate Similarity	NPD2494	Approved
0.716	Intermediate Similarity	NPD3268	Approved
0.7159	Intermediate Similarity	NPD4288	Approved
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7134	Intermediate Similarity	NPD1201	Approved
0.7127	Intermediate Similarity	NPD2403	Approved
0.7125	Intermediate Similarity	NPD2798	Approved
0.7122	Intermediate Similarity	NPD7907	Approved
0.7118	Intermediate Similarity	NPD3300	Phase 2
0.7108	Intermediate Similarity	NPD4665	Approved
0.7108	Intermediate Similarity	NPD4111	Phase 1
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7086	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7077	Intermediate Similarity	NPD3452	Approved
0.7077	Intermediate Similarity	NPD3450	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7068	Intermediate Similarity	NPD6213	Phase 3
0.7068	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6212	Phase 3
0.7063	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD1203	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