NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.03
Volume:	242.021
LogP:	1.877
LogD:	1.695
LogS:	-3.392
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	2.558
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.08
MDCK Permeability:	5.839536697749281e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.705
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.57106018066406%
Volume Distribution (VD):	0.632
Pgp-substrate:	11.20837116241455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.537
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.18
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	6.128
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.624
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.411
Skin Sensitization:	0.942
Carcinogencity:	0.062
Eye Corrosion:	0.218
Eye Irritation:	0.955
Respiratory Toxicity:	0.141

Download Data

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

Natural Product: NPC276930

Natural Product ID:	NPC276930
*Common Name:**	1,2,6,8-Tetrahydroxyxanthen-9-One
IUPAC Name:	1,2,6,8-tetrahydroxyxanthen-9-one
Synonyms:
Standard InCHIKey:	RVOUOPDWADMVBA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O6/c14-5-3-7(16)10-9(4-5)19-8-2-1-6(15)12(17)11(8)13(10)18/h1-4,14-17H
SMILES:	Oc1cc(O)c2c(c1)oc1c(c2=O)c(O)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL187043
PubChem CID:	5281658
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
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO12166	Gentiana bavarica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00303-4]
NPO12166	Gentiana bavarica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)86673-X]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[1002/hlca.19760590517]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19489596]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[931752]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15414	Swertia swertiopsis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12166	Gentiana bavarica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28852	Euphorbia makinoi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12166	Gentiana bavarica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19861	Drypetes molunduana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28149	Polygala fallax	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15414	Swertia swertiopsis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28532	Streptomyces gougerotii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27923	Calophyllum apetalum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26420	Swertia perennis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28417	Monnina emarginata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28149	Polygala fallax	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28366	Cladonia furcata	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28252	Lophozia barbata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12166	Gentiana bavarica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28852	Euphorbia makinoi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19861	Drypetes molunduana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28020	Hypaphorus subumbrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28793	Wettsteinia inversa	Species	Adelanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20937	Heterocapsa niei	Species	Heterocapsaceae	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	=	24000.0	nM	PMID[572694]

☑ 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 NPC276930 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	566
0.1-0.2	2270
0.2-0.3	5840
0.3-0.4	11846
0.4-0.5	4567
0.5-0.6	4209
0.6-0.7	5137
0.7-0.8	4693
0.8-0.85	1929
0.85-0.9	1005
0.9-0.95	524
0.95-1	111

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC62042
0.986	High Similarity	NPC61620
0.9859	High Similarity	NPC194856
0.9792	High Similarity	NPC204515
0.9792	High Similarity	NPC251110
0.9789	High Similarity	NPC130230
0.9789	High Similarity	NPC239312
0.9789	High Similarity	NPC207729
0.9789	High Similarity	NPC275772
0.9724	High Similarity	NPC120537
0.9724	High Similarity	NPC199100
0.9724	High Similarity	NPC180234
0.9722	High Similarity	NPC248102
0.972	High Similarity	NPC12367
0.972	High Similarity	NPC118726
0.9658	High Similarity	NPC88645
0.9658	High Similarity	NPC271779
0.9658	High Similarity	NPC206238
0.9658	High Similarity	NPC167091
0.9658	High Similarity	NPC292214
0.9655	High Similarity	NPC202157
0.9653	High Similarity	NPC17286
0.9653	High Similarity	NPC216318
0.9653	High Similarity	NPC259713
0.9653	High Similarity	NPC296197
0.9653	High Similarity	NPC195351
0.9589	High Similarity	NPC39007
0.9589	High Similarity	NPC161277
0.9589	High Similarity	NPC101996
0.9586	High Similarity	NPC77858
0.9586	High Similarity	NPC45873
0.9586	High Similarity	NPC184136
0.9583	High Similarity	NPC196277
0.9583	High Similarity	NPC43669
0.9583	High Similarity	NPC294852
0.9583	High Similarity	NPC321011
0.9583	High Similarity	NPC188679
0.9583	High Similarity	NPC272721
0.9577	High Similarity	NPC279121
0.9527	High Similarity	NPC201837
0.9527	High Similarity	NPC191146
0.9527	High Similarity	NPC68093
0.9527	High Similarity	NPC235165
0.9527	High Similarity	NPC255106
0.9524	High Similarity	NPC89474
0.9521	High Similarity	NPC171010
0.9521	High Similarity	NPC149614
0.9521	High Similarity	NPC225731
0.9521	High Similarity	NPC117579
0.9517	High Similarity	NPC1612
0.9517	High Similarity	NPC183959
0.9514	High Similarity	NPC77378
0.951	High Similarity	NPC70136
0.9507	High Similarity	NPC169479
0.9507	High Similarity	NPC159855
0.9507	High Similarity	NPC175013
0.9463	High Similarity	NPC156057
0.9463	High Similarity	NPC245758
0.9463	High Similarity	NPC99597
0.9463	High Similarity	NPC472911
0.9463	High Similarity	NPC474208
0.9463	High Similarity	NPC162869
0.9463	High Similarity	NPC210084
0.9463	High Similarity	NPC474836
0.9463	High Similarity	NPC472910
0.9463	High Similarity	NPC78225
0.9463	High Similarity	NPC475267
0.9463	High Similarity	NPC472913
0.9463	High Similarity	NPC48208
0.9463	High Similarity	NPC222814
0.9463	High Similarity	NPC96167
0.9463	High Similarity	NPC472914
0.9459	High Similarity	NPC113906
0.9459	High Similarity	NPC2928
0.9456	High Similarity	NPC120163
0.9456	High Similarity	NPC83508
0.9456	High Similarity	NPC198826
0.9456	High Similarity	NPC27208
0.9456	High Similarity	NPC275836
0.9456	High Similarity	NPC212678
0.9456	High Similarity	NPC293183
0.9456	High Similarity	NPC162313
0.9456	High Similarity	NPC131624
0.9456	High Similarity	NPC25270
0.9456	High Similarity	NPC222830
0.9456	High Similarity	NPC156222
0.9456	High Similarity	NPC239128
0.9456	High Similarity	NPC256283
0.9456	High Similarity	NPC187498
0.9456	High Similarity	NPC71334
0.9456	High Similarity	NPC241498
0.9456	High Similarity	NPC57030
0.9456	High Similarity	NPC100887
0.9456	High Similarity	NPC301323
0.9456	High Similarity	NPC188203
0.9456	High Similarity	NPC275722
0.9452	High Similarity	NPC179183
0.9452	High Similarity	NPC29231
0.9448	High Similarity	NPC3036
0.9448	High Similarity	NPC218490
0.9444	High Similarity	NPC20791
0.9444	High Similarity	NPC179271
0.94	High Similarity	NPC185258
0.94	High Similarity	NPC172770
0.9396	High Similarity	NPC274730
0.9396	High Similarity	NPC138243
0.9396	High Similarity	NPC142339
0.9396	High Similarity	NPC472916
0.9392	High Similarity	NPC274327
0.9392	High Similarity	NPC183878
0.9392	High Similarity	NPC176775
0.9392	High Similarity	NPC231018
0.9392	High Similarity	NPC47781
0.9392	High Similarity	NPC255350
0.9392	High Similarity	NPC69394
0.9392	High Similarity	NPC145379
0.9392	High Similarity	NPC22519
0.9392	High Similarity	NPC160951
0.9384	High Similarity	NPC294502
0.9384	High Similarity	NPC105512
0.9384	High Similarity	NPC200221
0.9379	High Similarity	NPC168803
0.9379	High Similarity	NPC74881
0.9379	High Similarity	NPC51443
0.9379	High Similarity	NPC95864
0.9379	High Similarity	NPC108406
0.9338	High Similarity	NPC139036
0.9338	High Similarity	NPC45146
0.9338	High Similarity	NPC235018
0.9338	High Similarity	NPC263449
0.9338	High Similarity	NPC204290
0.9333	High Similarity	NPC300727
0.9333	High Similarity	NPC79053
0.9333	High Similarity	NPC262286
0.9333	High Similarity	NPC469584
0.9333	High Similarity	NPC241904
0.9333	High Similarity	NPC36852
0.9333	High Similarity	NPC236796
0.9329	High Similarity	NPC92659
0.9329	High Similarity	NPC201136
0.9329	High Similarity	NPC213622
0.9329	High Similarity	NPC196439
0.9329	High Similarity	NPC4455
0.9329	High Similarity	NPC163780
0.9329	High Similarity	NPC138360
0.9329	High Similarity	NPC280339
0.9329	High Similarity	NPC201451
0.9329	High Similarity	NPC146165
0.9329	High Similarity	NPC37392
0.9329	High Similarity	NPC227325
0.9329	High Similarity	NPC44079
0.9329	High Similarity	NPC167815
0.9329	High Similarity	NPC20830
0.9329	High Similarity	NPC26227
0.9329	High Similarity	NPC472909
0.9329	High Similarity	NPC183597
0.9329	High Similarity	NPC214138
0.9329	High Similarity	NPC256612
0.9329	High Similarity	NPC128863
0.9329	High Similarity	NPC50715
0.9329	High Similarity	NPC2476
0.9324	High Similarity	NPC302950
0.9324	High Similarity	NPC219582
0.9324	High Similarity	NPC236637
0.9324	High Similarity	NPC125300
0.9324	High Similarity	NPC260491
0.9324	High Similarity	NPC249570
0.9324	High Similarity	NPC142540
0.9324	High Similarity	NPC240476
0.9324	High Similarity	NPC61506
0.9324	High Similarity	NPC246162
0.9324	High Similarity	NPC9743
0.9324	High Similarity	NPC36835
0.932	High Similarity	NPC3825
0.932	High Similarity	NPC306821
0.932	High Similarity	NPC88804
0.932	High Similarity	NPC10467
0.932	High Similarity	NPC151473
0.9315	High Similarity	NPC119059
0.9315	High Similarity	NPC287395
0.9315	High Similarity	NPC183655
0.931	High Similarity	NPC169749
0.9306	High Similarity	NPC59551
0.9276	High Similarity	NPC266314
0.9276	High Similarity	NPC472275
0.9276	High Similarity	NPC167678
0.9276	High Similarity	NPC308992
0.9276	High Similarity	NPC29876
0.9276	High Similarity	NPC162668
0.9276	High Similarity	NPC32694
0.9272	High Similarity	NPC95936
0.9272	High Similarity	NPC152904
0.9272	High Similarity	NPC250214
0.9272	High Similarity	NPC476242
0.9272	High Similarity	NPC329091
0.9272	High Similarity	NPC100123
0.9267	High Similarity	NPC266960
0.9267	High Similarity	NPC49824
0.9267	High Similarity	NPC98661
0.9267	High Similarity	NPC474638

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 NPC276930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1041
0.2-0.3	1900
0.3-0.4	2717
0.4-0.5	1632
0.5-0.6	917
0.6-0.7	297
0.7-0.8	96
0.8-0.85	35
0.85-0.9	12
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9577	High Similarity	NPD1511	Approved
0.9444	High Similarity	NPD1512	Approved
0.9392	High Similarity	NPD2801	Approved
0.9324	High Similarity	NPD1934	Approved
0.9262	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD1550	Clinical (unspecified phase)
0.8828	High Similarity	NPD1549	Phase 2
0.8766	High Similarity	NPD3882	Suspended
0.8734	High Similarity	NPD6166	Phase 2
0.8734	High Similarity	NPD6167	Clinical (unspecified phase)
0.8734	High Similarity	NPD6168	Clinical (unspecified phase)
0.8732	High Similarity	NPD943	Approved
0.8645	High Similarity	NPD4868	Clinical (unspecified phase)
0.8625	High Similarity	NPD3818	Discontinued
0.8621	High Similarity	NPD1510	Phase 2
0.86	High Similarity	NPD4378	Clinical (unspecified phase)
0.8589	High Similarity	NPD4338	Clinical (unspecified phase)
0.8519	High Similarity	NPD7074	Phase 3
0.8516	High Similarity	NPD1465	Phase 2
0.8481	Intermediate Similarity	NPD5494	Approved
0.8472	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD7054	Approved
0.8451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD4380	Phase 2
0.8405	Intermediate Similarity	NPD7472	Approved
0.838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1607	Approved
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6797	Phase 2
0.8303	Intermediate Similarity	NPD7251	Discontinued
0.8239	Intermediate Similarity	NPD7075	Discontinued
0.8235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1613	Approved
0.8219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2796	Approved
0.8165	Intermediate Similarity	NPD7819	Suspended
0.8165	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5402	Approved
0.8113	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8092	Intermediate Similarity	NPD3750	Approved
0.8086	Intermediate Similarity	NPD1247	Approved
0.8079	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6799	Approved
0.8041	Intermediate Similarity	NPD230	Phase 1
0.8038	Intermediate Similarity	NPD7411	Suspended
0.8026	Intermediate Similarity	NPD2800	Approved
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7947	Intermediate Similarity	NPD1551	Phase 2
0.7919	Intermediate Similarity	NPD447	Suspended
0.7904	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6801	Discontinued
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3748	Approved
0.7744	Intermediate Similarity	NPD919	Approved
0.774	Intermediate Similarity	NPD1203	Approved
0.7725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD6100	Approved
0.7688	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD1243	Approved
0.7673	Intermediate Similarity	NPD920	Approved
0.7673	Intermediate Similarity	NPD5403	Approved
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2534	Approved
0.7658	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD5401	Approved
0.7658	Intermediate Similarity	NPD2533	Approved
0.7655	Intermediate Similarity	NPD9269	Phase 2
0.7633	Intermediate Similarity	NPD3751	Discontinued
0.7625	Intermediate Similarity	NPD1653	Approved
0.7622	Intermediate Similarity	NPD7768	Phase 2
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.758	Intermediate Similarity	NPD2309	Approved
0.7564	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD6190	Approved
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1933	Approved
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7415	Intermediate Similarity	NPD9717	Approved
0.7415	Intermediate Similarity	NPD1608	Approved
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7403	Intermediate Similarity	NPD6651	Approved
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD1470	Approved
0.7379	Intermediate Similarity	NPD9268	Approved
0.7377	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7390	Discontinued
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7347	Intermediate Similarity	NPD422	Phase 1
0.7347	Intermediate Similarity	NPD1201	Approved
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7314	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1481	Phase 2
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2861	Phase 2
0.7255	Intermediate Similarity	NPD3268	Approved
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD411	Approved
0.7251	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1535	Discovery
0.7229	Intermediate Similarity	NPD6844	Discontinued
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2798	Approved
0.7211	Intermediate Similarity	NPD17	Approved
0.72	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD4308	Phase 3
0.7193	Intermediate Similarity	NPD5710	Approved
0.7193	Intermediate Similarity	NPD5711	Approved
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7175	Intermediate Similarity	NPD8313	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7167	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD4749	Approved
0.7126	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD7228	Approved
0.7124	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1471	Phase 3
0.7104	Intermediate Similarity	NPD4363	Phase 3
0.7104	Intermediate Similarity	NPD4360	Phase 2
0.7101	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD4965	Approved
0.7101	Intermediate Similarity	NPD4967	Phase 2
0.7097	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6779	Approved
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7052	Intermediate Similarity	NPD5242	Approved
0.7041	Intermediate Similarity	NPD2296	Approved
0.7039	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD3267	Approved
0.7019	Intermediate Similarity	NPD2654	Approved
0.7011	Intermediate Similarity	NPD2403	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6987	Remote Similarity	NPD6233	Phase 2
0.6986	Remote Similarity	NPD6671	Approved
0.6984	Remote Similarity	NPD7435	Discontinued
0.6961	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD9545	Approved
0.6946	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4307	Phase 2
0.6941	Remote Similarity	NPD5353	Approved
0.6939	Remote Similarity	NPD9493	Approved
0.6939	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5408	Approved
0.6937	Remote Similarity	NPD5405	Approved
0.6937	Remote Similarity	NPD5404	Approved
0.6937	Remote Similarity	NPD5406	Approved
0.6935	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2354	Approved
0.6928	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6919	Remote Similarity	NPD2899	Discontinued
0.6914	Remote Similarity	NPD1652	Phase 2
0.6907	Remote Similarity	NPD7783	Phase 2
0.6907	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7696	Phase 3

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