NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.03
Volume:	250.761
LogP:	2.682
LogD:	2.366
LogS:	-3.718
# Rotatable Bonds:	0
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	2.609
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	1.6994990801322274e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.169

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	94.52835083007812%
Volume Distribution (VD):	0.815
Pgp-substrate:	9.023513793945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	9.371
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.657
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.27
Skin Sensitization:	0.876
Carcinogencity:	0.889
Eye Corrosion:	0.031
Eye Irritation:	0.936
Respiratory Toxicity:	0.212

Download Data

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

Natural Product: NPC162668

Natural Product ID:	NPC162668
*Common Name:**	1,7-Dihydroxy-2,3-Methylenedioxyxanthone
IUPAC Name:	8,11-dihydroxy-[1,3]dioxolo[4,5-b]xanthen-10-one
Synonyms:
Standard InCHIKey:	BMRWSZGEVSNEOM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8O6/c15-6-1-2-8-7(3-6)12(16)11-9(20-8)4-10-14(13(11)17)19-5-18-10/h1-4,15,17H,5H2
SMILES:	Oc1ccc2c(c1)c(=O)c1c(o2)cc2c(c1O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436930
PubChem CID:	5316803
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
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)93394-0]
NPO28551	Centaurium erythraea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50044a037]
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843580]
NPO28166	Streptomyces nodosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730252]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18693022]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19201199]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647823]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	root	n.a.	PMID[24317429]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28149	Polygala fallax	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28205	Isodon setschwanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28515	Campanula kachetica	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14228	Mattfeldanthus nobilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24709	Justicia tranquebariensis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28551	Centaurium erythraea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28659	Euphorbia terracina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24634	Derris elliptica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28239	Indigofera hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21581	Polygala arillata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28365	Gelasinospora kobi	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21068	Centaurea sulphurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28166	Streptomyces nodosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28456	Anaptychia obscurata	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28205	Isodon setschwanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20441	Glaucium flavum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19599	Pogostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28434	Isotropis forrestii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25755	Haplopappus multifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28149	Polygala fallax	Species	Polygalaceae	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	20600.0	nM	PMID[564675]
NPT34	Cell Line	BV-2	Mus musculus	Inhibition	>	80.0	%	PMID[564675]

☑ 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 NPC162668 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	553
0.1-0.2	2186
0.2-0.3	5419
0.3-0.4	11236
0.4-0.5	5709
0.5-0.6	4111
0.6-0.7	5150
0.7-0.8	4993
0.8-0.85	1808
0.85-0.9	1103
0.9-0.95	415
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC470178
0.9557	High Similarity	NPC42892
0.9548	High Similarity	NPC285973
0.9548	High Similarity	NPC225624
0.9487	High Similarity	NPC260640
0.9487	High Similarity	NPC295009
0.9477	High Similarity	NPC167091
0.9477	High Similarity	NPC88645
0.9477	High Similarity	NPC271779
0.9477	High Similarity	NPC206238
0.9477	High Similarity	NPC244371
0.9477	High Similarity	NPC292214
0.9474	High Similarity	NPC251110
0.9427	High Similarity	NPC469575
0.9416	High Similarity	NPC18954
0.9412	High Similarity	NPC101996
0.9412	High Similarity	NPC39007
0.9412	High Similarity	NPC161277
0.9412	High Similarity	NPC120537
0.9412	High Similarity	NPC199100
0.9412	High Similarity	NPC180234
0.9408	High Similarity	NPC248102
0.9408	High Similarity	NPC61620
0.9367	High Similarity	NPC110257
0.9359	High Similarity	NPC62518
0.9359	High Similarity	NPC215375
0.9346	High Similarity	NPC149614
0.9346	High Similarity	NPC171010
0.9317	High Similarity	NPC34287
0.9317	High Similarity	NPC471416
0.9317	High Similarity	NPC212748
0.9313	High Similarity	NPC76482
0.9308	High Similarity	NPC165720
0.9295	High Similarity	NPC167595
0.9295	High Similarity	NPC99597
0.9295	High Similarity	NPC210084
0.929	High Similarity	NPC2928
0.9281	High Similarity	NPC62042
0.9281	High Similarity	NPC179183
0.9281	High Similarity	NPC45873
0.9281	High Similarity	NPC29231
0.9276	High Similarity	NPC194856
0.9276	High Similarity	NPC196277
0.9276	High Similarity	NPC272721
0.9276	High Similarity	NPC276930
0.9276	High Similarity	NPC43669
0.9264	High Similarity	NPC472607
0.9259	High Similarity	NPC48773
0.9259	High Similarity	NPC205076
0.9259	High Similarity	NPC307518
0.9255	High Similarity	NPC471457
0.9255	High Similarity	NPC112755
0.9255	High Similarity	NPC170675
0.925	High Similarity	NPC113093
0.9245	High Similarity	NPC88043
0.9236	High Similarity	NPC16935
0.9231	High Similarity	NPC255106
0.9231	High Similarity	NPC472916
0.9231	High Similarity	NPC235165
0.9221	High Similarity	NPC204515
0.9221	High Similarity	NPC117579
0.9221	High Similarity	NPC288316
0.9216	High Similarity	NPC259713
0.9216	High Similarity	NPC294502
0.9216	High Similarity	NPC296197
0.9216	High Similarity	NPC200221
0.9216	High Similarity	NPC17286
0.9216	High Similarity	NPC216318
0.9211	High Similarity	NPC77378
0.9211	High Similarity	NPC207729
0.9198	High Similarity	NPC72249
0.9198	High Similarity	NPC44558
0.9198	High Similarity	NPC474434
0.9198	High Similarity	NPC105511
0.9198	High Similarity	NPC224462
0.9198	High Similarity	NPC21190
0.9198	High Similarity	NPC183357
0.9198	High Similarity	NPC22195
0.9193	High Similarity	NPC146792
0.9193	High Similarity	NPC58716
0.9193	High Similarity	NPC45400
0.9193	High Similarity	NPC45618
0.9177	High Similarity	NPC269906
0.9172	High Similarity	NPC472914
0.9172	High Similarity	NPC472911
0.9172	High Similarity	NPC162869
0.9172	High Similarity	NPC48208
0.9172	High Similarity	NPC475267
0.9172	High Similarity	NPC262286
0.9172	High Similarity	NPC36852
0.9172	High Similarity	NPC222814
0.9172	High Similarity	NPC472910
0.9172	High Similarity	NPC78225
0.9172	High Similarity	NPC474208
0.9172	High Similarity	NPC258644
0.9172	High Similarity	NPC245758
0.9172	High Similarity	NPC472913
0.9172	High Similarity	NPC96167
0.9172	High Similarity	NPC156057
0.9172	High Similarity	NPC474836
0.9167	High Similarity	NPC20830
0.9167	High Similarity	NPC256612
0.9161	High Similarity	NPC188203
0.9161	High Similarity	NPC212678
0.9161	High Similarity	NPC57030
0.9161	High Similarity	NPC275722
0.9161	High Similarity	NPC198826
0.9161	High Similarity	NPC120163
0.9161	High Similarity	NPC131624
0.9161	High Similarity	NPC25270
0.9161	High Similarity	NPC292460
0.9161	High Similarity	NPC256283
0.9161	High Similarity	NPC71334
0.9161	High Similarity	NPC35544
0.9161	High Similarity	NPC239128
0.9161	High Similarity	NPC293183
0.9161	High Similarity	NPC187498
0.9161	High Similarity	NPC104728
0.9161	High Similarity	NPC100887
0.9161	High Similarity	NPC162313
0.9161	High Similarity	NPC156222
0.9161	High Similarity	NPC241498
0.9161	High Similarity	NPC83508
0.9161	High Similarity	NPC275836
0.9161	High Similarity	NPC301323
0.9161	High Similarity	NPC222830
0.915	High Similarity	NPC287395
0.915	High Similarity	NPC183655
0.915	High Similarity	NPC12367
0.915	High Similarity	NPC118726
0.9141	High Similarity	NPC475825
0.9141	High Similarity	NPC235575
0.9141	High Similarity	NPC223375
0.9141	High Similarity	NPC260263
0.9136	High Similarity	NPC210042
0.9136	High Similarity	NPC45638
0.9136	High Similarity	NPC105025
0.9136	High Similarity	NPC186807
0.9136	High Similarity	NPC475942
0.9136	High Similarity	NPC201292
0.9136	High Similarity	NPC93337
0.9136	High Similarity	NPC469931
0.9136	High Similarity	NPC95855
0.9136	High Similarity	NPC471287
0.9136	High Similarity	NPC183036
0.9136	High Similarity	NPC58053
0.9136	High Similarity	NPC472383
0.9136	High Similarity	NPC229687
0.9136	High Similarity	NPC472381
0.9136	High Similarity	NPC226294
0.9119	High Similarity	NPC308992
0.9119	High Similarity	NPC188486
0.9119	High Similarity	NPC94155
0.9119	High Similarity	NPC470756
0.9114	High Similarity	NPC195832
0.9114	High Similarity	NPC196879
0.9108	High Similarity	NPC474638
0.9108	High Similarity	NPC138243
0.9108	High Similarity	NPC68093
0.9108	High Similarity	NPC201837
0.9108	High Similarity	NPC191146
0.9103	High Similarity	NPC274327
0.9103	High Similarity	NPC47781
0.9103	High Similarity	NPC231018
0.9103	High Similarity	NPC255350
0.9103	High Similarity	NPC472915
0.9103	High Similarity	NPC176775
0.9103	High Similarity	NPC145379
0.9103	High Similarity	NPC183878
0.9103	High Similarity	NPC160951
0.9103	High Similarity	NPC22519
0.9103	High Similarity	NPC69394
0.9097	High Similarity	NPC31363
0.9097	High Similarity	NPC225731
0.9091	High Similarity	NPC183959
0.9091	High Similarity	NPC1612
0.9091	High Similarity	NPC257714
0.9091	High Similarity	NPC156635
0.9085	High Similarity	NPC275772
0.9085	High Similarity	NPC51774
0.9085	High Similarity	NPC168803
0.9085	High Similarity	NPC239312
0.9085	High Similarity	NPC236191
0.9085	High Similarity	NPC46941
0.9085	High Similarity	NPC239549
0.9085	High Similarity	NPC130230
0.908	High Similarity	NPC84265
0.908	High Similarity	NPC245014
0.908	High Similarity	NPC282987
0.9074	High Similarity	NPC471288
0.9074	High Similarity	NPC48640
0.9074	High Similarity	NPC149244
0.9074	High Similarity	NPC229729
0.9074	High Similarity	NPC116745
0.9074	High Similarity	NPC135345
0.9074	High Similarity	NPC93099
0.9062	High Similarity	NPC84515
0.9062	High Similarity	NPC300537
0.9062	High Similarity	NPC125991
0.9062	High Similarity	NPC472448

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 NPC162668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	475
0.1-0.2	1009
0.2-0.3	2059
0.3-0.4	2680
0.4-0.5	1640
0.5-0.6	869
0.6-0.7	273
0.7-0.8	100
0.8-0.85	31
0.85-0.9	9
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9313	High Similarity	NPD3818	Discontinued
0.9103	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD1934	Approved
0.8916	High Similarity	NPD4338	Clinical (unspecified phase)
0.8889	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8848	High Similarity	NPD7074	Phase 3
0.8788	High Similarity	NPD7054	Approved
0.8774	High Similarity	NPD1512	Approved
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.8735	High Similarity	NPD7472	Approved
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.8589	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD6797	Phase 2
0.8521	High Similarity	NPD7251	Discontinued
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6166	Phase 2
0.8494	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7808	Phase 3
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8395	Intermediate Similarity	NPD1465	Phase 2
0.8377	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.825	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8224	Intermediate Similarity	NPD943	Approved
0.821	Intermediate Similarity	NPD4380	Phase 2
0.8204	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1240	Approved
0.8086	Intermediate Similarity	NPD1653	Approved
0.8061	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6232	Discontinued
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.8012	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7976	Intermediate Similarity	NPD919	Approved
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.795	Intermediate Similarity	NPD6799	Approved
0.795	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.7871	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1613	Approved
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7861	Intermediate Similarity	NPD3751	Discontinued
0.7848	Intermediate Similarity	NPD2796	Approved
0.7831	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD230	Phase 1
0.7821	Intermediate Similarity	NPD447	Suspended
0.7821	Intermediate Similarity	NPD1933	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7764	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7702	Intermediate Similarity	NPD2800	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7593	Intermediate Similarity	NPD1243	Approved
0.759	Intermediate Similarity	NPD5403	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7578	Intermediate Similarity	NPD2344	Approved
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD2532	Approved
0.7576	Intermediate Similarity	NPD5401	Approved
0.7572	Intermediate Similarity	NPD6959	Discontinued
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7453	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.7436	Intermediate Similarity	NPD9494	Approved
0.7419	Intermediate Similarity	NPD1203	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6782	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7396	Intermediate Similarity	NPD3226	Approved
0.7394	Intermediate Similarity	NPD2309	Approved
0.7394	Intermediate Similarity	NPD6190	Approved
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7316	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7202	Intermediate Similarity	NPD7697	Approved
0.7202	Intermediate Similarity	NPD7698	Approved
0.7202	Intermediate Similarity	NPD7696	Phase 3
0.7198	Intermediate Similarity	NPD7240	Approved
0.7195	Intermediate Similarity	NPD6100	Approved
0.7195	Intermediate Similarity	NPD6099	Approved
0.7194	Intermediate Similarity	NPD8151	Discontinued
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7584	Approved
0.7165	Intermediate Similarity	NPD7871	Phase 2
0.7165	Intermediate Similarity	NPD7870	Phase 2
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7158	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD2798	Approved
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7115	Intermediate Similarity	NPD9717	Approved
0.7112	Intermediate Similarity	NPD4287	Approved
0.7095	Intermediate Similarity	NPD5242	Approved
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD3764	Approved
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD9268	Approved
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5005	Approved
0.7062	Intermediate Similarity	NPD5006	Approved
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7801	Approved
0.7031	Intermediate Similarity	NPD7700	Phase 2
0.7031	Intermediate Similarity	NPD7699	Phase 2
0.7029	Intermediate Similarity	NPD8455	Phase 2
0.7013	Intermediate Similarity	NPD1548	Phase 1
0.7012	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD1470	Approved
0.6975	Remote Similarity	NPD411	Approved
0.6971	Remote Similarity	NPD6844	Discontinued
0.6961	Remote Similarity	NPD2403	Approved
0.6957	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD6832	Phase 2
0.6949	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1471	Phase 3
0.6944	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD4420	Approved
0.6943	Remote Similarity	NPD422	Phase 1
0.6943	Remote Similarity	NPD1091	Approved
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD7033	Discontinued
0.6915	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	Approved
0.6911	Remote Similarity	NPD6212	Phase 3
0.6911	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6213	Phase 3
0.6907	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7390	Discontinued
0.6901	Remote Similarity	NPD4357	Discontinued
0.6899	Remote Similarity	NPD1481	Phase 2
0.6893	Remote Similarity	NPD4288	Approved
0.6893	Remote Similarity	NPD2296	Approved
0.6891	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7549	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