NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.04
Volume:	224.441
LogP:	2.878
LogD:	2.538
LogS:	-3.409
# Rotatable Bonds:	0
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	2.215
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	1.518100907560438e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	95.236328125%
Volume Distribution (VD):	0.522
Pgp-substrate:	7.622550964355469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.497
CYP2C19-inhibitor:	0.431
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	3.786
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.751
Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.873
Carcinogencity:	0.873
Eye Corrosion:	0.381
Eye Irritation:	0.967
Respiratory Toxicity:	0.311

Download Data

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

Natural Product: NPC59551

Natural Product ID:	NPC59551
*Common Name:**	1,5-Dihydroxyxanthen-9-One
IUPAC Name:	1,5-dihydroxyxanthen-9-one
Synonyms:
Standard InCHIKey:	APIPFXZYOMIJQG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O4/c14-8-4-2-6-10-11(8)12(16)7-3-1-5-9(15)13(7)17-10/h1-6,14-15H
SMILES:	Oc1cccc2c1oc1cccc(c1c2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL185686
PubChem CID:	5480299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18794770]
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000780]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	Chinese	n.a.	n.a.	PMID[20624681]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[21214226]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288442]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7400820]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO30864	Garcinia spp	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26911	Mesua thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19755	Artemisia anomala	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]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13305	Mammea africana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31543	Calophyllum spp	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26911	Mesua thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27674	Garcinia spp.	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13305	Mammea africana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24379	Calophyllum spp.	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21034	0cardia alba	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21852	Montanoa karwinskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13305	Mammea africana	Species	Calophyllaceae	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]
NPO26911	Mesua thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16291	Leptochloa digitata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1755	Pinus heldreichii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20897	Suberites domuncula	Species	Suberitidae	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]
NPO20773	Jacobaea persoonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20647	Eugenia myrcianthes	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23186	Verbena bonariensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18516	Aplysilla spinifera	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21601	Crocus sieberi	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18412	Lobophytum microlobulatum	Species	Alcyoniidae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	730.0	nM	PMID[521560]

☑ 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 NPC59551 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	555
0.1-0.2	2325
0.2-0.3	6104
0.3-0.4	11763
0.4-0.5	4469
0.5-0.6	4578
0.6-0.7	5359
0.7-0.8	4739
0.8-0.85	1598
0.85-0.9	780
0.9-0.95	373
0.95-1	54

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC209278
0.9716	High Similarity	NPC272721
0.9716	High Similarity	NPC43669
0.9716	High Similarity	NPC196277
0.9648	High Similarity	NPC200221
0.9648	High Similarity	NPC294502
0.9645	High Similarity	NPC77378
0.958	High Similarity	NPC29231
0.9514	High Similarity	NPC251110
0.9507	High Similarity	NPC46941
0.9507	High Similarity	NPC168803
0.9448	High Similarity	NPC75069
0.9444	High Similarity	NPC248102
0.9444	High Similarity	NPC61620
0.9384	High Similarity	NPC273462
0.9384	High Similarity	NPC271779
0.9384	High Similarity	NPC206238
0.9384	High Similarity	NPC292214
0.9384	High Similarity	NPC33051
0.9384	High Similarity	NPC167091
0.9384	High Similarity	NPC49402
0.9384	High Similarity	NPC70433
0.9384	High Similarity	NPC227337
0.9384	High Similarity	NPC88645
0.9379	High Similarity	NPC31363
0.932	High Similarity	NPC57674
0.932	High Similarity	NPC230149
0.932	High Similarity	NPC168247
0.932	High Similarity	NPC117992
0.932	High Similarity	NPC152951
0.9315	High Similarity	NPC257648
0.9315	High Similarity	NPC199100
0.9315	High Similarity	NPC101996
0.9315	High Similarity	NPC180234
0.9315	High Similarity	NPC39007
0.9315	High Similarity	NPC477231
0.9315	High Similarity	NPC120537
0.9315	High Similarity	NPC161277
0.931	High Similarity	NPC45873
0.931	High Similarity	NPC151473
0.9306	High Similarity	NPC194856
0.9306	High Similarity	NPC276930
0.9257	High Similarity	NPC5322
0.9257	High Similarity	NPC474638
0.9257	High Similarity	NPC133970
0.9257	High Similarity	NPC6633
0.9252	High Similarity	NPC469550
0.9247	High Similarity	NPC475076
0.9247	High Similarity	NPC171010
0.9247	High Similarity	NPC149614
0.9241	High Similarity	NPC296197
0.9241	High Similarity	NPC259713
0.9241	High Similarity	NPC183959
0.9241	High Similarity	NPC17286
0.9241	High Similarity	NPC105512
0.9241	High Similarity	NPC1612
0.9241	High Similarity	NPC216318
0.9236	High Similarity	NPC188074
0.9236	High Similarity	NPC125449
0.9236	High Similarity	NPC95864
0.9236	High Similarity	NPC207729
0.9231	High Similarity	NPC70136
0.9214	High Similarity	NPC18457
0.9195	High Similarity	NPC210084
0.9195	High Similarity	NPC304008
0.9195	High Similarity	NPC218313
0.9195	High Similarity	NPC187745
0.9195	High Similarity	NPC474681
0.9195	High Similarity	NPC161960
0.9195	High Similarity	NPC299520
0.9195	High Similarity	NPC129684
0.9195	High Similarity	NPC99597
0.9189	High Similarity	NPC472280
0.9189	High Similarity	NPC200246
0.9189	High Similarity	NPC256925
0.9189	High Similarity	NPC2928
0.9184	High Similarity	NPC39732
0.9184	High Similarity	NPC472912
0.9184	High Similarity	NPC60972
0.9184	High Similarity	NPC236637
0.9184	High Similarity	NPC260979
0.9184	High Similarity	NPC302950
0.9184	High Similarity	NPC219582
0.9178	High Similarity	NPC260582
0.9178	High Similarity	NPC179183
0.9178	High Similarity	NPC62042
0.9172	High Similarity	NPC294852
0.9172	High Similarity	NPC118726
0.9172	High Similarity	NPC3036
0.9172	High Similarity	NPC188679
0.9172	High Similarity	NPC321011
0.9172	High Similarity	NPC12367
0.9161	High Similarity	NPC279121
0.9133	High Similarity	NPC55738
0.9133	High Similarity	NPC204879
0.9128	High Similarity	NPC472907
0.9128	High Similarity	NPC472916
0.9128	High Similarity	NPC255106
0.9128	High Similarity	NPC68093
0.9128	High Similarity	NPC138243
0.9128	High Similarity	NPC191146
0.9128	High Similarity	NPC472455
0.9128	High Similarity	NPC115853
0.9128	High Similarity	NPC235165
0.9128	High Similarity	NPC470600
0.9122	High Similarity	NPC27532
0.9122	High Similarity	NPC256346
0.9122	High Similarity	NPC246328
0.9122	High Similarity	NPC325028
0.9122	High Similarity	NPC472905
0.9122	High Similarity	NPC18727
0.9122	High Similarity	NPC141212
0.9116	High Similarity	NPC117579
0.9116	High Similarity	NPC225731
0.9116	High Similarity	NPC204515
0.911	High Similarity	NPC52005
0.911	High Similarity	NPC183950
0.911	High Similarity	NPC200060
0.911	High Similarity	NPC142876
0.911	High Similarity	NPC195763
0.911	High Similarity	NPC137062
0.911	High Similarity	NPC264550
0.911	High Similarity	NPC40290
0.911	High Similarity	NPC223579
0.911	High Similarity	NPC139293
0.911	High Similarity	NPC69430
0.911	High Similarity	NPC333691
0.911	High Similarity	NPC287101
0.911	High Similarity	NPC264289
0.9103	High Similarity	NPC74881
0.9103	High Similarity	NPC239312
0.9103	High Similarity	NPC130230
0.9103	High Similarity	NPC275772
0.9103	High Similarity	NPC51443
0.9091	High Similarity	NPC287722
0.9091	High Similarity	NPC175013
0.9085	High Similarity	NPC145673
0.9067	High Similarity	NPC474836
0.9067	High Similarity	NPC67876
0.9067	High Similarity	NPC48208
0.9067	High Similarity	NPC96167
0.9067	High Similarity	NPC472913
0.9067	High Similarity	NPC475267
0.9067	High Similarity	NPC180011
0.9067	High Similarity	NPC222814
0.9067	High Similarity	NPC156057
0.9067	High Similarity	NPC472910
0.9067	High Similarity	NPC136674
0.9067	High Similarity	NPC291508
0.9067	High Similarity	NPC472963
0.9067	High Similarity	NPC472911
0.9067	High Similarity	NPC474208
0.9067	High Similarity	NPC162869
0.9067	High Similarity	NPC262286
0.9067	High Similarity	NPC472914
0.9067	High Similarity	NPC78225
0.9067	High Similarity	NPC52530
0.9067	High Similarity	NPC245758
0.9067	High Similarity	NPC219867
0.9067	High Similarity	NPC36852
0.906	High Similarity	NPC31018
0.906	High Similarity	NPC234255
0.906	High Similarity	NPC20830
0.906	High Similarity	NPC256612
0.906	High Similarity	NPC255807
0.9054	High Similarity	NPC131624
0.9054	High Similarity	NPC9743
0.9054	High Similarity	NPC27208
0.9054	High Similarity	NPC187498
0.9054	High Similarity	NPC36835
0.9054	High Similarity	NPC240476
0.9054	High Similarity	NPC246162
0.9054	High Similarity	NPC156222
0.9054	High Similarity	NPC239128
0.9054	High Similarity	NPC237994
0.9054	High Similarity	NPC260491
0.9054	High Similarity	NPC198826
0.9054	High Similarity	NPC83508
0.9054	High Similarity	NPC100887
0.9054	High Similarity	NPC301323
0.9054	High Similarity	NPC212678
0.9054	High Similarity	NPC241498
0.9054	High Similarity	NPC25270
0.9054	High Similarity	NPC222830
0.9054	High Similarity	NPC275836
0.9054	High Similarity	NPC256283
0.9054	High Similarity	NPC71334
0.9054	High Similarity	NPC57030
0.9054	High Similarity	NPC162313
0.9054	High Similarity	NPC275722
0.9054	High Similarity	NPC120163
0.9054	High Similarity	NPC55205
0.9054	High Similarity	NPC188203
0.9054	High Similarity	NPC293183
0.9054	High Similarity	NPC61506
0.9041	High Similarity	NPC80710
0.9041	High Similarity	NPC120464
0.9041	High Similarity	NPC139364
0.9041	High Similarity	NPC183655
0.9041	High Similarity	NPC254702

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 NPC59551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	508
0.1-0.2	1053
0.2-0.3	1847
0.3-0.4	2740
0.4-0.5	1648
0.5-0.6	954
0.6-0.7	266
0.7-0.8	89
0.8-0.85	30
0.85-0.9	9
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD1934	Approved
0.9161	High Similarity	NPD1511	Approved
0.9034	High Similarity	NPD1512	Approved
0.8993	High Similarity	NPD2801	Approved
0.8874	High Similarity	NPD3882	Suspended
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8681	High Similarity	NPD1549	Phase 2
0.8611	High Similarity	NPD1552	Clinical (unspecified phase)
0.8611	High Similarity	NPD1550	Clinical (unspecified phase)
0.8608	High Similarity	NPD3818	Discontinued
0.8599	High Similarity	NPD6168	Clinical (unspecified phase)
0.8599	High Similarity	NPD6166	Phase 2
0.8599	High Similarity	NPD6167	Clinical (unspecified phase)
0.8582	High Similarity	NPD943	Approved
0.8506	High Similarity	NPD4868	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1465	Phase 2
0.8472	Intermediate Similarity	NPD1510	Phase 2
0.8429	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD447	Suspended
0.8385	Intermediate Similarity	NPD7074	Phase 3
0.8357	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD1240	Approved
0.8301	Intermediate Similarity	NPD4380	Phase 2
0.8288	Intermediate Similarity	NPD1551	Phase 2
0.8272	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD7075	Discontinued
0.8217	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1607	Approved
0.8205	Intermediate Similarity	NPD5402	Approved
0.8194	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1613	Approved
0.8188	Intermediate Similarity	NPD3750	Approved
0.8141	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD5403	Approved
0.8092	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1203	Approved
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8041	Intermediate Similarity	NPD2796	Approved
0.8026	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8014	Intermediate Similarity	NPD1933	Approved
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7931	Intermediate Similarity	NPD2313	Discontinued
0.7929	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7411	Suspended
0.7867	Intermediate Similarity	NPD2346	Discontinued
0.7862	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3926	Phase 2
0.7852	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3748	Approved
0.7848	Intermediate Similarity	NPD6801	Discontinued
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.784	Intermediate Similarity	NPD1247	Approved
0.7834	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD919	Approved
0.7815	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD3226	Approved
0.777	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD9717	Approved
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1470	Approved
0.7702	Intermediate Similarity	NPD7768	Phase 2
0.7682	Intermediate Similarity	NPD6100	Approved
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7682	Intermediate Similarity	NPD6099	Approved
0.7665	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2800	Approved
0.7643	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2344	Approved
0.7622	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.7616	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2799	Discontinued
0.7603	Intermediate Similarity	NPD9494	Approved
0.7595	Intermediate Similarity	NPD1653	Approved
0.759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD411	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7552	Intermediate Similarity	NPD1201	Approved
0.7534	Intermediate Similarity	NPD2798	Approved
0.7532	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7444	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8313	Approved
0.7442	Intermediate Similarity	NPD8312	Approved
0.7436	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD6832	Phase 2
0.7421	Intermediate Similarity	NPD920	Approved
0.7419	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD9269	Phase 2
0.7379	Intermediate Similarity	NPD1608	Approved
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7347	Intermediate Similarity	NPD2797	Approved
0.7342	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD422	Phase 1
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7296	Intermediate Similarity	NPD2533	Approved
0.7296	Intermediate Similarity	NPD2534	Approved
0.7296	Intermediate Similarity	NPD2532	Approved
0.7279	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5953	Discontinued
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7254	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9493	Approved
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3764	Approved
0.7215	Intermediate Similarity	NPD6190	Approved
0.7212	Intermediate Similarity	NPD4288	Approved
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD37	Approved
0.7193	Intermediate Similarity	NPD7228	Approved
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD17	Approved
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7169	Intermediate Similarity	NPD4966	Approved
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD6651	Approved
0.7125	Intermediate Similarity	NPD4357	Discontinued
0.7114	Intermediate Similarity	NPD3267	Approved
0.7114	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD1296	Phase 2
0.7103	Intermediate Similarity	NPD9268	Approved
0.7086	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5536	Phase 2
0.7081	Intermediate Similarity	NPD4661	Approved
0.7081	Intermediate Similarity	NPD4662	Approved
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7067	Intermediate Similarity	NPD1019	Discontinued
0.7051	Intermediate Similarity	NPD7033	Discontinued
0.7039	Intermediate Similarity	NPD4287	Approved
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD228	Approved
0.702	Intermediate Similarity	NPD3018	Phase 2
0.7019	Intermediate Similarity	NPD7390	Discontinued
0.7018	Intermediate Similarity	NPD5242	Approved
0.7013	Intermediate Similarity	NPD1558	Phase 1
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9266	Approved
0.6929	Remote Similarity	NPD74	Approved
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8434	Phase 2
0.6927	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD1241	Discontinued
0.6913	Remote Similarity	NPD1481	Phase 2
0.6908	Remote Similarity	NPD2861	Phase 2
0.6905	Remote Similarity	NPD5353	Approved
0.6905	Remote Similarity	NPD2296	Approved
0.6902	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2354	Approved
0.6882	Remote Similarity	NPD6780	Approved
0.6882	Remote Similarity	NPD6777	Approved
0.6882	Remote Similarity	NPD6776	Approved
0.6882	Remote Similarity	NPD6781	Approved
0.6882	Remote Similarity	NPD6778	Approved
0.6882	Remote Similarity	NPD6779	Approved
0.6882	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD1652	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data