NPASS Compound

Structure

CID186397 OpenBabel06191715562D 23 25 0 0 0 0 0 0 0 0999 V2000 -5.1962 1.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 1.7321 -0.0000 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 -5.1962 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 -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 -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 -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 3.4641 0.0000 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 -1.7321 1.0000 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	4.442
LogD:	2.615
LogS:	-3.22
# Rotatable Bonds:	2
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	2.701
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.867
MDCK Permeability:	1.2527217222668696e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.404
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	93.09307098388672%
Volume Distribution (VD):	0.669
Pgp-substrate:	8.89864444732666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.8
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.4
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	6.95
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.553
Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.623
Skin Sensitization:	0.931
Carcinogencity:	0.204
Eye Corrosion:	0.004
Eye Irritation:	0.902
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC186397

Natural Product ID:	NPC186397
*Common Name:**	1,3,7-Trihydroxy-2-Prenylxanthone
IUPAC Name:	1,3,7-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Standard InCHIKey:	FLWKTILHZPCXDW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-9(2)3-5-11-13(20)8-15-16(17(11)21)18(22)12-7-10(19)4-6-14(12)23-15/h3-4,6-8,19-21H,5H2,1-2H3
SMILES:	CC(=CCc1c(O)cc2c(c1O)c(=O)c1c(o2)ccc(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506229
PubChem CID:	5495920
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:0003517] 2-prenylated xanthones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(74)80113-5]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10361686]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724839]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113969]
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]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000780]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	leaves	Bobai, Guangxi Province, China	2005-Dec	PMID[24679044]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	Barks	n.a.	n.a.	PMID[24754786]
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[24960143]
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]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6775	Cistanche salsa	Species	Orobanchaceae	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]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	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]
NPO1154	Neomeris annulata	Species	Dasycladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16291	Leptochloa digitata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11471	Garcinia oblongifolia	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]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19563	Gyrophora hyperborea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18013	Sceletium subvelutinum	n.a.	n.a.	n.a.	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]
NPO1755	Pinus heldreichii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9298	Piper wightii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6948	Davidsoniella virescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15264	Garcinia paucinervis	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]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18412	Lobophytum microlobulatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	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]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26341	Trifolium resupinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10228	Ascochyta viciae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2812	Lecanora kukunorensis	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15242	Setosphaeria holmii	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	6
MIC	8
Others	4

Activity Type	# Activity
Cell Line	5
Organism	9
Others	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	>	640000.0	nM	PMID[483332]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[483335]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[483335]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[483335]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	21300.0	nM	PMID[483335]
NPT27	Others	Unspecified		CC50	>	640000.0	nM	PMID[483332]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	128.0	ug.mL-1	PMID[483333]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT925	Organism	Emericella nidulans	Emericella nidulans	MIC	>	128.0	ug.mL-1	PMID[483333]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9.0	mm	PMID[483333]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[483335]
NPT610	Others	Molecular identity unknown		Survival	=	82.87	%	PMID[483336]
NPT21990	SINGLE PROTEIN	7,8-dihydro-8-oxoguanine triphosphatase	Homo sapiens	IC50	=	1700.0	nM	PMID[483337]

☑ 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 NPC186397 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	436
0.1-0.2	1881
0.2-0.3	4540
0.3-0.4	11378
0.4-0.5	6484
0.5-0.6	3865
0.6-0.7	5375
0.7-0.8	4406
0.8-0.85	1988
0.85-0.9	1700
0.9-0.95	623
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37135
0.993	High Similarity	NPC223988
0.993	High Similarity	NPC266499
0.9722	High Similarity	NPC120105
0.9722	High Similarity	NPC227122
0.9722	High Similarity	NPC101957
0.9645	High Similarity	NPC159855
0.9645	High Similarity	NPC169479
0.9524	High Similarity	NPC280530
0.9524	High Similarity	NPC178964
0.9524	High Similarity	NPC95842
0.9507	High Similarity	NPC144499
0.9504	High Similarity	NPC69769
0.9459	High Similarity	NPC113906
0.9452	High Similarity	NPC37348
0.9448	High Similarity	NPC39195
0.9444	High Similarity	NPC187282
0.9444	High Similarity	NPC24136
0.9444	High Similarity	NPC290133
0.9441	High Similarity	NPC18585
0.9441	High Similarity	NPC166138
0.9441	High Similarity	NPC106985
0.94	High Similarity	NPC172770
0.94	High Similarity	NPC185258
0.9396	High Similarity	NPC191146
0.9396	High Similarity	NPC138243
0.9396	High Similarity	NPC68093
0.9384	High Similarity	NPC10027
0.9384	High Similarity	NPC65775
0.9379	High Similarity	NPC308200
0.9375	High Similarity	NPC234629
0.9375	High Similarity	NPC311741
0.9366	High Similarity	NPC270883
0.9366	High Similarity	NPC172986
0.9366	High Similarity	NPC145673
0.9366	High Similarity	NPC261227
0.9362	High Similarity	NPC18457
0.9338	High Similarity	NPC471976
0.9333	High Similarity	NPC78225
0.9333	High Similarity	NPC79053
0.9333	High Similarity	NPC196448
0.9333	High Similarity	NPC36852
0.9333	High Similarity	NPC262286
0.9333	High Similarity	NPC476981
0.9329	High Similarity	NPC55662
0.9329	High Similarity	NPC166054
0.9324	High Similarity	NPC474843
0.932	High Similarity	NPC230713
0.932	High Similarity	NPC78335
0.932	High Similarity	NPC472633
0.9315	High Similarity	NPC145467
0.931	High Similarity	NPC196114
0.931	High Similarity	NPC472629
0.931	High Similarity	NPC477955
0.931	High Similarity	NPC299011
0.9306	High Similarity	NPC143896
0.9306	High Similarity	NPC221432
0.9306	High Similarity	NPC38219
0.9306	High Similarity	NPC310130
0.9306	High Similarity	NPC91560
0.9306	High Similarity	NPC75049
0.9306	High Similarity	NPC219915
0.9306	High Similarity	NPC293053
0.9306	High Similarity	NPC164980
0.9306	High Similarity	NPC149026
0.9306	High Similarity	NPC169591
0.9306	High Similarity	NPC212932
0.9306	High Similarity	NPC39329
0.9306	High Similarity	NPC68104
0.9306	High Similarity	NPC175504
0.9306	High Similarity	NPC257097
0.9306	High Similarity	NPC150408
0.9306	High Similarity	NPC9117
0.9306	High Similarity	NPC24821
0.9306	High Similarity	NPC190637
0.9301	High Similarity	NPC110969
0.9301	High Similarity	NPC64908
0.9301	High Similarity	NPC3188
0.9301	High Similarity	NPC156590
0.9301	High Similarity	NPC205006
0.9301	High Similarity	NPC118840
0.9301	High Similarity	NPC147688
0.9296	High Similarity	NPC301217
0.9296	High Similarity	NPC303633
0.9296	High Similarity	NPC96565
0.9296	High Similarity	NPC216978
0.9296	High Similarity	NPC55018
0.9296	High Similarity	NPC220062
0.9276	High Similarity	NPC472275
0.9276	High Similarity	NPC167678
0.9276	High Similarity	NPC3629
0.9276	High Similarity	NPC29876
0.9267	High Similarity	NPC142339
0.9262	High Similarity	NPC273462
0.9262	High Similarity	NPC472462
0.9262	High Similarity	NPC70433
0.9262	High Similarity	NPC33051
0.9262	High Similarity	NPC227337
0.9262	High Similarity	NPC135522
0.9262	High Similarity	NPC472915
0.9262	High Similarity	NPC49402
0.9257	High Similarity	NPC149614
0.9257	High Similarity	NPC117579
0.9257	High Similarity	NPC170169
0.9252	High Similarity	NPC178202
0.9252	High Similarity	NPC269420
0.9252	High Similarity	NPC471114
0.9252	High Similarity	NPC317492
0.9241	High Similarity	NPC326500
0.9241	High Similarity	NPC470890
0.9241	High Similarity	NPC473015
0.9241	High Similarity	NPC271288
0.9241	High Similarity	NPC311144
0.9241	High Similarity	NPC209040
0.9241	High Similarity	NPC184649
0.9241	High Similarity	NPC216538
0.9241	High Similarity	NPC273538
0.9241	High Similarity	NPC303185
0.9241	High Similarity	NPC473013
0.9241	High Similarity	NPC124780
0.9241	High Similarity	NPC236766
0.9241	High Similarity	NPC87486
0.9241	High Similarity	NPC197252
0.9236	High Similarity	NPC226636
0.9236	High Similarity	NPC166934
0.9236	High Similarity	NPC11561
0.9236	High Similarity	NPC1089
0.9236	High Similarity	NPC324134
0.9236	High Similarity	NPC223500
0.9236	High Similarity	NPC473042
0.9236	High Similarity	NPC37496
0.9236	High Similarity	NPC32739
0.9236	High Similarity	NPC40833
0.9236	High Similarity	NPC265040
0.9236	High Similarity	NPC324436
0.9236	High Similarity	NPC76338
0.9236	High Similarity	NPC328164
0.9236	High Similarity	NPC306829
0.9236	High Similarity	NPC194432
0.9236	High Similarity	NPC148757
0.9236	High Similarity	NPC296917
0.9236	High Similarity	NPC227579
0.9236	High Similarity	NPC125855
0.9236	High Similarity	NPC200694
0.9236	High Similarity	NPC76372
0.9236	High Similarity	NPC66515
0.9236	High Similarity	NPC161506
0.9236	High Similarity	NPC228504
0.9236	High Similarity	NPC167624
0.9236	High Similarity	NPC78
0.9236	High Similarity	NPC166482
0.9236	High Similarity	NPC73028
0.9236	High Similarity	NPC10937
0.9236	High Similarity	NPC220998
0.9236	High Similarity	NPC177354
0.9236	High Similarity	NPC64915
0.9236	High Similarity	NPC182852
0.9236	High Similarity	NPC107572
0.9231	High Similarity	NPC305355
0.9231	High Similarity	NPC235239
0.9231	High Similarity	NPC475680
0.9231	High Similarity	NPC241100
0.9231	High Similarity	NPC159275
0.9225	High Similarity	NPC201395
0.9216	High Similarity	NPC83922
0.9216	High Similarity	NPC329760
0.9216	High Similarity	NPC472448
0.9211	High Similarity	NPC204290
0.9211	High Similarity	NPC235018
0.9211	High Similarity	NPC476980
0.9211	High Similarity	NPC45146
0.9205	High Similarity	NPC236796
0.9205	High Similarity	NPC165977
0.9205	High Similarity	NPC217677
0.9205	High Similarity	NPC181960
0.92	High Similarity	NPC117992
0.92	High Similarity	NPC37392
0.92	High Similarity	NPC230149
0.92	High Similarity	NPC168247
0.92	High Similarity	NPC57674
0.92	High Similarity	NPC472909
0.92	High Similarity	NPC152951
0.9195	High Similarity	NPC142527
0.9195	High Similarity	NPC249570
0.9189	High Similarity	NPC29777
0.9189	High Similarity	NPC3825
0.9189	High Similarity	NPC471115
0.9189	High Similarity	NPC88804
0.9189	High Similarity	NPC179183
0.9189	High Similarity	NPC62042
0.9184	High Similarity	NPC168085
0.9184	High Similarity	NPC296869
0.9184	High Similarity	NPC266572
0.9184	High Similarity	NPC276930
0.9184	High Similarity	NPC194856
0.9178	High Similarity	NPC5820
0.9178	High Similarity	NPC124729
0.9178	High Similarity	NPC178343
0.9178	High Similarity	NPC469758
0.9178	High Similarity	NPC306488

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 NPC186397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	991
0.2-0.3	1593
0.3-0.4	2701
0.4-0.5	1849
0.5-0.6	1078
0.6-0.7	348
0.7-0.8	115
0.8-0.85	49
0.85-0.9	20
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD4378	Clinical (unspecified phase)
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.9007	High Similarity	NPD2801	Approved
0.898	High Similarity	NPD7410	Clinical (unspecified phase)
0.8958	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD1550	Clinical (unspecified phase)
0.8882	High Similarity	NPD7819	Suspended
0.8816	High Similarity	NPD1934	Approved
0.8808	High Similarity	NPD4380	Phase 2
0.8784	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD1510	Phase 2
0.875	High Similarity	NPD7411	Suspended
0.8732	High Similarity	NPD1240	Approved
0.8718	High Similarity	NPD5494	Approved
0.871	High Similarity	NPD7075	Discontinued
0.8701	High Similarity	NPD8443	Clinical (unspecified phase)
0.869	High Similarity	NPD2796	Approved
0.869	High Similarity	NPD2935	Discontinued
0.8667	High Similarity	NPD1512	Approved
0.8636	High Similarity	NPD7096	Clinical (unspecified phase)
0.8611	High Similarity	NPD1607	Approved
0.8544	High Similarity	NPD6959	Discontinued
0.8526	High Similarity	NPD3882	Suspended
0.8514	High Similarity	NPD2800	Approved
0.8471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD3750	Approved
0.8291	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7768	Phase 2
0.8289	Intermediate Similarity	NPD6799	Approved
0.8282	Intermediate Similarity	NPD3818	Discontinued
0.8267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.8258	Intermediate Similarity	NPD3226	Approved
0.8255	Intermediate Similarity	NPD2346	Discontinued
0.8243	Intermediate Similarity	NPD2799	Discontinued
0.8243	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2532	Approved
0.8235	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD2534	Approved
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8228	Intermediate Similarity	NPD3817	Phase 2
0.8228	Intermediate Similarity	NPD5402	Approved
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8207	Intermediate Similarity	NPD2313	Discontinued
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6559	Discontinued
0.8182	Intermediate Similarity	NPD7074	Phase 3
0.8146	Intermediate Similarity	NPD1243	Approved
0.8144	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2344	Approved
0.8129	Intermediate Similarity	NPD920	Approved
0.8121	Intermediate Similarity	NPD7054	Approved
0.8095	Intermediate Similarity	NPD943	Approved
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8086	Intermediate Similarity	NPD1247	Approved
0.8072	Intermediate Similarity	NPD7472	Approved
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8067	Intermediate Similarity	NPD6099	Approved
0.8067	Intermediate Similarity	NPD6100	Approved
0.8024	Intermediate Similarity	NPD5953	Discontinued
0.8024	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD7286	Phase 2
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD6651	Approved
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1465	Phase 2
0.7935	Intermediate Similarity	NPD7390	Discontinued
0.7929	Intermediate Similarity	NPD7808	Phase 3
0.7922	Intermediate Similarity	NPD2309	Approved
0.7871	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.777	Intermediate Similarity	NPD4625	Phase 3
0.7744	Intermediate Similarity	NPD919	Approved
0.7711	Intermediate Similarity	NPD5711	Approved
0.7711	Intermediate Similarity	NPD5710	Approved
0.7708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4908	Phase 1
0.7703	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2798	Approved
0.7682	Intermediate Similarity	NPD447	Suspended
0.7658	Intermediate Similarity	NPD5401	Approved
0.7655	Intermediate Similarity	NPD9717	Approved
0.7654	Intermediate Similarity	NPD6844	Discontinued
0.7635	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD1470	Approved
0.76	Intermediate Similarity	NPD3268	Approved
0.7593	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7584	Intermediate Similarity	NPD4360	Phase 2
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7584	Intermediate Similarity	NPD4363	Phase 3
0.7569	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD4308	Phase 3
0.7532	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD5404	Approved
0.7484	Intermediate Similarity	NPD5408	Approved
0.7484	Intermediate Similarity	NPD5406	Approved
0.7484	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7469	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7466	Intermediate Similarity	NPD1201	Approved
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1471	Phase 3
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7368	Intermediate Similarity	NPD3764	Approved
0.736	Intermediate Similarity	NPD4287	Approved
0.7351	Intermediate Similarity	NPD7435	Discontinued
0.7351	Intermediate Similarity	NPD7698	Approved
0.7351	Intermediate Similarity	NPD7696	Phase 3
0.7351	Intermediate Similarity	NPD7697	Approved
0.7349	Intermediate Similarity	NPD4288	Approved
0.7349	Intermediate Similarity	NPD2296	Approved
0.7348	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4361	Phase 2
0.7343	Intermediate Similarity	NPD6671	Approved
0.7342	Intermediate Similarity	NPD2654	Approved
0.7341	Intermediate Similarity	NPD1729	Discontinued
0.7338	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD17	Approved
0.7325	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3225	Approved
0.7312	Intermediate Similarity	NPD7870	Phase 2
0.7312	Intermediate Similarity	NPD7871	Phase 2
0.7308	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1481	Phase 2
0.7297	Intermediate Similarity	NPD3972	Approved
0.7273	Intermediate Similarity	NPD4307	Phase 2
0.7267	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3267	Approved
0.7256	Intermediate Similarity	NPD7458	Discontinued
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7234	Intermediate Similarity	NPD7584	Approved
0.723	Intermediate Similarity	NPD1535	Discovery
0.7212	Intermediate Similarity	NPD6585	Discontinued
0.7204	Intermediate Similarity	NPD6823	Phase 2
0.7198	Intermediate Similarity	NPD6535	Approved
0.7198	Intermediate Similarity	NPD6534	Approved
0.7196	Intermediate Similarity	NPD7701	Phase 2
0.7195	Intermediate Similarity	NPD1653	Approved
0.7192	Intermediate Similarity	NPD9545	Approved
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3027	Phase 3
0.7188	Intermediate Similarity	NPD7003	Approved
0.7186	Intermediate Similarity	NPD5761	Phase 2
0.7186	Intermediate Similarity	NPD5760	Phase 2
0.7173	Intermediate Similarity	NPD7783	Phase 2
0.7173	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9493	Approved
0.717	Intermediate Similarity	NPD2424	Discontinued
0.7169	Intermediate Similarity	NPD5889	Approved
0.7169	Intermediate Similarity	NPD5890	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