NPASS Compound

Structure

CID300727 OpenBabel06191716112D 30 32 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -3.4641 -3.0000 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 -1.7321 -1.0000 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 1.7321 2.0000 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 -6.0622 -2.5000 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 -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 -2.5981 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 -0.8660 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 0.8660 0.5000 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 -2.5981 0.5000 0.0000 C 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 1.7321 -1.0000 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 0.0000 -1.0000 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 22 23 1 0 0 0 0 23 28 2 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.17
Volume:	427.004
LogP:	5.843
LogD:	3.81
LogS:	-3.16
# Rotatable Bonds:	6
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.644
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:	-4.984
MDCK Permeability:	1.2806091945094522e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.421
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.313

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.76348114013672%
Volume Distribution (VD):	0.774
Pgp-substrate:	5.943178176879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.75
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	6.522
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.191
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.412
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.915
Carcinogencity:	0.354
Eye Corrosion:	0.011
Eye Irritation:	0.904
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC300727

Natural Product ID:	NPC300727
*Common Name:**	Rubraxanthone
IUPAC Name:	1-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,6,8-trihydroxy-2-methoxyxanthen-9-one
Synonyms:	Rubraxanthone
Standard InCHIKey:	JLTSTSRANGPLOQ-RIYZIHGNSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-13(2)6-5-7-14(3)8-9-16-21-20(12-18(27)24(16)29-4)30-19-11-15(25)10-17(26)22(19)23(21)28/h6,8,10-12,25-27H,5,7,9H2,1-4H3/b14-8+
SMILES:	CC(=CCC/C(=C/Cc1c2c(cc(c1OC)O)oc1cc(cc(c1c2=O)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458846
PubChem CID:	9953366
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
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]
NPO2060	Garcinia parvifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12494345]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608849]
NPO15507	Allanblackia monticola	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	PMID[16394561]
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]
NPO22533	Garcinia merguensis	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[18523924]
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	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	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]
NPO408	Garcinia dioica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8887739]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO30446	Mesua	Genus	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
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]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22533	Garcinia merguensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7692	Liatris provincialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15507	Allanblackia monticola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25216	Senecio vellereus	Species	Asteraceae	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]
NPO7692	Liatris provincialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO408	Garcinia dioica	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]
NPO2060	Garcinia parvifolia	Species	Clusiaceae	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]
NPO15507	Allanblackia monticola	Species	Clusiaceae	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]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	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]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10169	Hypogymnia physodes	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22533	Garcinia merguensis	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
IC50	9
MIC	6
Others	10

Activity Type	# Activity
Cell Line	9
CELL-LINE	1
Organism	7
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[533846]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[533846]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[533847]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[533849]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[533849]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[533849]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[533849]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[533846]
NPT2	Others	Unspecified		Inhibition	=	39.5	%	PMID[533846]
NPT2	Others	Unspecified		Inhibition	=	74.1	%	PMID[533846]
NPT2	Others	Unspecified		Inhibition	=	96.8	%	PMID[533846]
NPT2	Others	Unspecified		IC50	=	340.0	molar ratio	PMID[533846]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	3.4	ug.mL-1	PMID[533847]
NPT2	Others	Unspecified		Ratio IC50	=	0.76	n.a.	PMID[533847]
NPT2	Others	Unspecified		Inhibition	=	71.2	%	PMID[533848]
NPT2	Others	Unspecified		IC50	=	23400.0	nM	PMID[533848]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[533848]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2.0	ug.mL-1	PMID[533848]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[533848]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[533848]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	64.0	ug.mL-1	PMID[533848]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	64.0	ug.mL-1	PMID[533848]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	IC50	>	10000.0	nM	PMID[533849]

☑ 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 NPC300727 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	443
0.1-0.2	1798
0.2-0.3	4433
0.3-0.4	10972
0.4-0.5	7054
0.5-0.6	3567
0.6-0.7	4880
0.7-0.8	5268
0.8-0.85	2354
0.85-0.9	1191
0.9-0.95	630
0.95-1	107

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241904
0.9933	High Similarity	NPC274730
0.9933	High Similarity	NPC476242
0.9868	High Similarity	NPC14353
0.9868	High Similarity	NPC228785
0.9868	High Similarity	NPC56085
0.9803	High Similarity	NPC40491
0.9803	High Similarity	NPC278052
0.9803	High Similarity	NPC61010
0.9801	High Similarity	NPC100123
0.9799	High Similarity	NPC89474
0.9737	High Similarity	NPC320359
0.9737	High Similarity	NPC200746
0.9735	High Similarity	NPC165977
0.9735	High Similarity	NPC217677
0.9735	High Similarity	NPC469584
0.9675	High Similarity	NPC475985
0.9675	High Similarity	NPC248638
0.9675	High Similarity	NPC220313
0.9675	High Similarity	NPC236521
0.9675	High Similarity	NPC7483
0.9675	High Similarity	NPC236132
0.9675	High Similarity	NPC152659
0.9671	High Similarity	NPC329091
0.9669	High Similarity	NPC142339
0.9664	High Similarity	NPC202157
0.9613	High Similarity	NPC239752
0.9613	High Similarity	NPC326520
0.9613	High Similarity	NPC472450
0.9613	High Similarity	NPC275780
0.961	High Similarity	NPC25152
0.9608	High Similarity	NPC474287
0.9608	High Similarity	NPC475886
0.9608	High Similarity	NPC139036
0.9605	High Similarity	NPC36852
0.9605	High Similarity	NPC236796
0.9605	High Similarity	NPC222814
0.9605	High Similarity	NPC474208
0.9605	High Similarity	NPC472913
0.9605	High Similarity	NPC156057
0.9605	High Similarity	NPC96167
0.9605	High Similarity	NPC475267
0.9605	High Similarity	NPC474836
0.9605	High Similarity	NPC262286
0.9605	High Similarity	NPC472911
0.9605	High Similarity	NPC472910
0.9605	High Similarity	NPC162869
0.9605	High Similarity	NPC245758
0.9605	High Similarity	NPC48208
0.9605	High Similarity	NPC78225
0.9605	High Similarity	NPC472914
0.96	High Similarity	NPC120537
0.96	High Similarity	NPC101996
0.96	High Similarity	NPC180234
0.96	High Similarity	NPC199100
0.9597	High Similarity	NPC151473
0.9551	High Similarity	NPC39091
0.9551	High Similarity	NPC170245
0.9548	High Similarity	NPC23298
0.9548	High Similarity	NPC270837
0.9548	High Similarity	NPC189473
0.9545	High Similarity	NPC474351
0.9545	High Similarity	NPC32694
0.9545	High Similarity	NPC474186
0.9545	High Similarity	NPC474187
0.9545	High Similarity	NPC475883
0.9542	High Similarity	NPC474290
0.9539	High Similarity	NPC138243
0.9539	High Similarity	NPC472916
0.9539	High Similarity	NPC68093
0.9539	High Similarity	NPC255106
0.9539	High Similarity	NPC235165
0.9539	High Similarity	NPC191146
0.9536	High Similarity	NPC167091
0.9536	High Similarity	NPC274327
0.9536	High Similarity	NPC206238
0.9536	High Similarity	NPC47781
0.9536	High Similarity	NPC292214
0.9536	High Similarity	NPC250822
0.9536	High Similarity	NPC88645
0.9536	High Similarity	NPC231018
0.9536	High Similarity	NPC255350
0.9536	High Similarity	NPC271779
0.9536	High Similarity	NPC276409
0.9536	High Similarity	NPC176775
0.9536	High Similarity	NPC160951
0.9536	High Similarity	NPC183878
0.9536	High Similarity	NPC145379
0.9536	High Similarity	NPC69394
0.9536	High Similarity	NPC22519
0.9536	High Similarity	NPC75279
0.9533	High Similarity	NPC117579
0.9533	High Similarity	NPC171010
0.949	High Similarity	NPC117854
0.949	High Similarity	NPC6588
0.949	High Similarity	NPC477154
0.9484	High Similarity	NPC229632
0.9484	High Similarity	NPC294965
0.9481	High Similarity	NPC36217
0.9481	High Similarity	NPC119224
0.9481	High Similarity	NPC45146
0.9481	High Similarity	NPC235018
0.9477	High Similarity	NPC136674
0.9477	High Similarity	NPC99597
0.9477	High Similarity	NPC181960
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC472963
0.9477	High Similarity	NPC223787
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC210084
0.9474	High Similarity	NPC472909
0.9474	High Similarity	NPC92659
0.9474	High Similarity	NPC163780
0.9474	High Similarity	NPC113906
0.9474	High Similarity	NPC50715
0.9474	High Similarity	NPC227325
0.9474	High Similarity	NPC167815
0.9474	High Similarity	NPC2476
0.9474	High Similarity	NPC256612
0.9474	High Similarity	NPC201136
0.9474	High Similarity	NPC213622
0.9474	High Similarity	NPC196439
0.9474	High Similarity	NPC4455
0.9474	High Similarity	NPC37392
0.9474	High Similarity	NPC208197
0.9474	High Similarity	NPC146165
0.9474	High Similarity	NPC138360
0.9474	High Similarity	NPC2928
0.9474	High Similarity	NPC280339
0.9474	High Similarity	NPC67396
0.9474	High Similarity	NPC20830
0.9474	High Similarity	NPC183597
0.9474	High Similarity	NPC128863
0.947	High Similarity	NPC275722
0.947	High Similarity	NPC198826
0.947	High Similarity	NPC161277
0.947	High Similarity	NPC83508
0.947	High Similarity	NPC162313
0.947	High Similarity	NPC275836
0.947	High Similarity	NPC256283
0.947	High Similarity	NPC39007
0.947	High Similarity	NPC25270
0.947	High Similarity	NPC241498
0.947	High Similarity	NPC131624
0.947	High Similarity	NPC239128
0.947	High Similarity	NPC301323
0.947	High Similarity	NPC120163
0.947	High Similarity	NPC100887
0.947	High Similarity	NPC187498
0.947	High Similarity	NPC293183
0.947	High Similarity	NPC71334
0.947	High Similarity	NPC212678
0.947	High Similarity	NPC188203
0.947	High Similarity	NPC57030
0.947	High Similarity	NPC156222
0.947	High Similarity	NPC222830
0.9467	High Similarity	NPC62042
0.9467	High Similarity	NPC179183
0.9467	High Similarity	NPC61620
0.9427	High Similarity	NPC472449
0.9427	High Similarity	NPC37870
0.9423	High Similarity	NPC41301
0.9423	High Similarity	NPC133065
0.9423	High Similarity	NPC146134
0.9423	High Similarity	NPC197168
0.9423	High Similarity	NPC474350
0.9419	High Similarity	NPC66288
0.9419	High Similarity	NPC266314
0.9416	High Similarity	NPC95936
0.9416	High Similarity	NPC250214
0.9416	High Similarity	NPC152904
0.9416	High Similarity	NPC235448
0.9412	High Similarity	NPC474520
0.9412	High Similarity	NPC24640
0.9412	High Similarity	NPC49824
0.9412	High Similarity	NPC472907
0.9408	High Similarity	NPC280937
0.9408	High Similarity	NPC18727
0.9408	High Similarity	NPC472905
0.9408	High Similarity	NPC472915
0.9404	High Similarity	NPC251110
0.9404	High Similarity	NPC149614
0.9404	High Similarity	NPC226973
0.9404	High Similarity	NPC208043
0.94	High Similarity	NPC48479
0.94	High Similarity	NPC328119
0.94	High Similarity	NPC177298
0.9363	High Similarity	NPC473286
0.9363	High Similarity	NPC39306
0.9363	High Similarity	NPC224280
0.9363	High Similarity	NPC25361
0.9359	High Similarity	NPC329760
0.9359	High Similarity	NPC52204
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC470694
0.9359	High Similarity	NPC201800
0.9359	High Similarity	NPC83922
0.9359	High Similarity	NPC472964
0.9355	High Similarity	NPC204290
0.9355	High Similarity	NPC476980

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 NPC300727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	971
0.2-0.3	1820
0.3-0.4	2723
0.4-0.5	1746
0.5-0.6	927
0.6-0.7	409
0.7-0.8	119
0.8-0.85	28
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9536	High Similarity	NPD2801	Approved
0.9342	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD2393	Clinical (unspecified phase)
0.894	High Similarity	NPD1511	Approved
0.8917	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD6166	Phase 2
0.8824	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD5494	Approved
0.8679	High Similarity	NPD4868	Clinical (unspecified phase)
0.8671	High Similarity	NPD1465	Phase 2
0.8667	High Similarity	NPD7074	Phase 3
0.8659	High Similarity	NPD3818	Discontinued
0.8642	High Similarity	NPD6232	Discontinued
0.8623	High Similarity	NPD4338	Clinical (unspecified phase)
0.8616	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD7054	Approved
0.8598	High Similarity	NPD7473	Discontinued
0.8554	High Similarity	NPD7472	Approved
0.8516	High Similarity	NPD4378	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD6797	Phase 2
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8365	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8343	Intermediate Similarity	NPD7251	Discontinued
0.8294	Intermediate Similarity	NPD7808	Phase 3
0.8282	Intermediate Similarity	NPD7075	Discontinued
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1510	Phase 2
0.816	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1240	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8117	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD6799	Approved
0.8061	Intermediate Similarity	NPD3749	Approved
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD5402	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8025	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8024	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7962	Intermediate Similarity	NPD2800	Approved
0.7953	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.791	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1613	Approved
0.7904	Intermediate Similarity	NPD6234	Discontinued
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD6099	Approved
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7814	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7744	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD447	Suspended
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7711	Intermediate Similarity	NPD37	Approved
0.7707	Intermediate Similarity	NPD3748	Approved
0.7692	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD7228	Approved
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4965	Approved
0.7679	Intermediate Similarity	NPD7768	Phase 2
0.7654	Intermediate Similarity	NPD7390	Discontinued
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5403	Approved
0.761	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD1653	Approved
0.7558	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD5710	Approved
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9494	Approved
0.7468	Intermediate Similarity	NPD6651	Approved
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.741	Intermediate Similarity	NPD920	Approved
0.7407	Intermediate Similarity	NPD1243	Approved
0.7374	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2403	Approved
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1203	Approved
0.7226	Intermediate Similarity	NPD1470	Approved
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7698	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD3268	Approved
0.7209	Intermediate Similarity	NPD5353	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.719	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7169	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7166	Intermediate Similarity	NPD4360	Phase 2
0.7166	Intermediate Similarity	NPD4363	Phase 3
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4287	Approved
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2797	Approved
0.711	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2654	Approved
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7088	Intermediate Similarity	NPD7549	Discontinued
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7065	Intermediate Similarity	NPD2899	Discontinued
0.7063	Intermediate Similarity	NPD6233	Phase 2
0.7056	Intermediate Similarity	NPD7801	Approved
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7039	Intermediate Similarity	NPD1548	Phase 1
0.7035	Intermediate Similarity	NPD6386	Approved
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6385	Approved
0.7033	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD9717	Approved
0.7031	Intermediate Similarity	NPD2493	Approved
0.7031	Intermediate Similarity	NPD2494	Approved
0.7025	Intermediate Similarity	NPD3018	Phase 2
0.7024	Intermediate Similarity	NPD4357	Discontinued

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