NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.05
Volume:	250.527
LogP:	2.621
LogD:	2.541
LogS:	-3.759
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.236
Fsp3:	0.071
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:	-4.782
MDCK Permeability:	1.3550702533393633e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.559
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.559

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	91.47444915771484%
Volume Distribution (VD):	0.813
Pgp-substrate:	12.527653694152832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.85
CYP3A4-inhibitor:	0.544
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	7.33
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.766
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.579
Skin Sensitization:	0.871
Carcinogencity:	0.815
Eye Corrosion:	0.068
Eye Irritation:	0.915
Respiratory Toxicity:	0.302

Download Data

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

Natural Product: NPC46941

Natural Product ID:	NPC46941
*Common Name:**	1,7-Dihydroxy-4-Methoxyxanthone
IUPAC Name:	1,7-dihydroxy-4-methoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	YDZGWMWSKOGVLG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O5/c1-18-11-5-3-9(16)12-13(17)8-6-7(15)2-4-10(8)19-14(11)12/h2-6,15-16H,1H3
SMILES:	COc1ccc(c2c1oc1ccc(cc1c2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484030
PubChem CID:	5465785
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
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11914965]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15182859]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	Uzbekistan	n.a.	PMID[15568778]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568778]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16310231]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16651783]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	roots	n.a.	n.a.	PMID[16989524]
NPO32808	cratoxylum formosum ssp. pruniflorum	Species	Hypericaceae	Eukaryota	stems	n.a.	n.a.	PMID[20608716]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428375]
NPO32798	polygala karensium	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22552195]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22863942]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24042007]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27116034]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27280968]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667821]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21963	Hypericum japonicum	Species	Hypericaceae	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]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27260	Polygala tenuifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	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	10
Others	2

Activity Type	# Activity
Cell Line	6
CELL-LINE	1
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8500.0	ug.mL-1	PMID[552593]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15200.0	ug.mL-1	PMID[552593]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	12.8	ug.mL-1	PMID[552595]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	9.33	ug.mL-1	PMID[552595]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	25.59	ug.mL-1	PMID[552595]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	28.42	ug.mL-1	PMID[552595]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	7400.0	nM	PMID[552596]
NPT34	Cell Line	BV-2	Mus musculus	Inhibition	>	80.0	%	PMID[552596]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	38880.0	nM	PMID[552597]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	15120.0	nM	PMID[552597]
NPT2	Others	Unspecified		Ratio IC50	=	243.0	n.a.	PMID[552595]
NPT20985	CELL-LINE	MCF7-ADR	Homo sapiens	IC50	=	185040.0	nM	PMID[552597]

☑ 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 NPC46941 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	512
0.1-0.2	2133
0.2-0.3	5445
0.3-0.4	11527
0.4-0.5	5475
0.5-0.6	4255
0.6-0.7	5459
0.7-0.8	4766
0.8-0.85	1724
0.85-0.9	884
0.9-0.95	379
0.95-1	138

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC294502
0.9859	High Similarity	NPC200221
0.9722	High Similarity	NPC149614
0.9653	High Similarity	NPC179183
0.9648	High Similarity	NPC209278
0.9589	High Similarity	NPC167091
0.9589	High Similarity	NPC271779
0.9589	High Similarity	NPC292214
0.9589	High Similarity	NPC88645
0.9589	High Similarity	NPC206238
0.9586	High Similarity	NPC117579
0.9571	High Similarity	NPC145673
0.9521	High Similarity	NPC161277
0.9521	High Similarity	NPC101996
0.9521	High Similarity	NPC120537
0.9521	High Similarity	NPC199100
0.9521	High Similarity	NPC180234
0.9521	High Similarity	NPC39007
0.9521	High Similarity	NPC75069
0.9507	High Similarity	NPC59551
0.9456	High Similarity	NPC472915
0.9452	High Similarity	NPC251110
0.9452	High Similarity	NPC475076
0.9452	High Similarity	NPC171010
0.9429	High Similarity	NPC18457
0.9396	High Similarity	NPC181960
0.9396	High Similarity	NPC210084
0.9396	High Similarity	NPC99597
0.9392	High Similarity	NPC37392
0.9392	High Similarity	NPC472909
0.9392	High Similarity	NPC2928
0.9384	High Similarity	NPC62042
0.9384	High Similarity	NPC306821
0.9384	High Similarity	NPC61620
0.9384	High Similarity	NPC248102
0.9384	High Similarity	NPC29231
0.9375	High Similarity	NPC231013
0.9329	High Similarity	NPC235165
0.9329	High Similarity	NPC472916
0.9329	High Similarity	NPC255106
0.9324	High Similarity	NPC280937
0.932	High Similarity	NPC208043
0.932	High Similarity	NPC308451
0.932	High Similarity	NPC226973
0.9267	High Similarity	NPC162869
0.9267	High Similarity	NPC472911
0.9267	High Similarity	NPC156057
0.9267	High Similarity	NPC474208
0.9267	High Similarity	NPC475267
0.9267	High Similarity	NPC96167
0.9267	High Similarity	NPC472914
0.9267	High Similarity	NPC472913
0.9267	High Similarity	NPC78225
0.9267	High Similarity	NPC222814
0.9267	High Similarity	NPC262286
0.9267	High Similarity	NPC476981
0.9267	High Similarity	NPC36852
0.9267	High Similarity	NPC474836
0.9267	High Similarity	NPC472910
0.9267	High Similarity	NPC48208
0.9267	High Similarity	NPC245758
0.9262	High Similarity	NPC255807
0.9262	High Similarity	NPC256612
0.9262	High Similarity	NPC31018
0.9262	High Similarity	NPC20830
0.9257	High Similarity	NPC212678
0.9257	High Similarity	NPC71334
0.9257	High Similarity	NPC100887
0.9257	High Similarity	NPC301123
0.9257	High Similarity	NPC83508
0.9257	High Similarity	NPC275836
0.9257	High Similarity	NPC301323
0.9257	High Similarity	NPC239128
0.9257	High Similarity	NPC25270
0.9257	High Similarity	NPC156222
0.9257	High Similarity	NPC57030
0.9257	High Similarity	NPC256283
0.9257	High Similarity	NPC293183
0.9257	High Similarity	NPC187498
0.9257	High Similarity	NPC162313
0.9257	High Similarity	NPC198826
0.9257	High Similarity	NPC188203
0.9257	High Similarity	NPC131624
0.9257	High Similarity	NPC241498
0.9257	High Similarity	NPC275722
0.9257	High Similarity	NPC222830
0.9257	High Similarity	NPC120163
0.9252	High Similarity	NPC45873
0.9252	High Similarity	NPC156953
0.9247	High Similarity	NPC10304
0.9247	High Similarity	NPC63256
0.9247	High Similarity	NPC272721
0.9247	High Similarity	NPC196277
0.9247	High Similarity	NPC276930
0.9247	High Similarity	NPC194856
0.9247	High Similarity	NPC287395
0.9247	High Similarity	NPC43669
0.9247	High Similarity	NPC183655
0.9231	High Similarity	NPC124467
0.9231	High Similarity	NPC214919
0.9211	High Similarity	NPC308992
0.9205	High Similarity	NPC152904
0.92	High Similarity	NPC68093
0.92	High Similarity	NPC191146
0.92	High Similarity	NPC138243
0.9195	High Similarity	NPC231018
0.9195	High Similarity	NPC47781
0.9195	High Similarity	NPC22519
0.9195	High Similarity	NPC176775
0.9195	High Similarity	NPC274327
0.9195	High Similarity	NPC183878
0.9195	High Similarity	NPC255350
0.9195	High Similarity	NPC145379
0.9195	High Similarity	NPC69394
0.9195	High Similarity	NPC160951
0.9195	High Similarity	NPC86485
0.9189	High Similarity	NPC262623
0.9189	High Similarity	NPC204515
0.9189	High Similarity	NPC31363
0.9184	High Similarity	NPC296197
0.9184	High Similarity	NPC328119
0.9184	High Similarity	NPC216318
0.9184	High Similarity	NPC259713
0.9184	High Similarity	NPC17286
0.9178	High Similarity	NPC207729
0.9178	High Similarity	NPC93034
0.9178	High Similarity	NPC119660
0.9178	High Similarity	NPC77378
0.9178	High Similarity	NPC12200
0.9172	High Similarity	NPC472917
0.9167	High Similarity	NPC159855
0.9167	High Similarity	NPC169479
0.915	High Similarity	NPC472448
0.915	High Similarity	NPC83922
0.9145	High Similarity	NPC476980
0.9145	High Similarity	NPC263449
0.9139	High Similarity	NPC129684
0.9139	High Similarity	NPC165977
0.9139	High Similarity	NPC241904
0.9139	High Similarity	NPC300727
0.9139	High Similarity	NPC469584
0.9139	High Similarity	NPC217677
0.9139	High Similarity	NPC299520
0.9133	High Similarity	NPC201136
0.9133	High Similarity	NPC152951
0.9133	High Similarity	NPC146165
0.9133	High Similarity	NPC2476
0.9133	High Similarity	NPC4455
0.9133	High Similarity	NPC57674
0.9133	High Similarity	NPC32557
0.9133	High Similarity	NPC201451
0.9133	High Similarity	NPC213622
0.9133	High Similarity	NPC138360
0.9133	High Similarity	NPC280339
0.9133	High Similarity	NPC168247
0.9133	High Similarity	NPC183597
0.9133	High Similarity	NPC26227
0.9133	High Similarity	NPC196439
0.9133	High Similarity	NPC44079
0.9133	High Similarity	NPC163780
0.9133	High Similarity	NPC167815
0.9133	High Similarity	NPC117992
0.9133	High Similarity	NPC128863
0.9133	High Similarity	NPC92659
0.9133	High Similarity	NPC113906
0.9133	High Similarity	NPC208197
0.9133	High Similarity	NPC50715
0.9133	High Similarity	NPC230149
0.9133	High Similarity	NPC227325
0.9133	High Similarity	NPC189960
0.9128	High Similarity	NPC216769
0.9128	High Similarity	NPC219582
0.9128	High Similarity	NPC257648
0.9128	High Similarity	NPC39732
0.9128	High Similarity	NPC131266
0.9128	High Similarity	NPC35763
0.9128	High Similarity	NPC269451
0.9128	High Similarity	NPC142540
0.9128	High Similarity	NPC477231
0.9128	High Similarity	NPC100971
0.9128	High Similarity	NPC60972
0.9128	High Similarity	NPC121522
0.9128	High Similarity	NPC245382
0.9128	High Similarity	NPC291802
0.9128	High Similarity	NPC236637
0.9128	High Similarity	NPC100263
0.9128	High Similarity	NPC302950
0.9128	High Similarity	NPC181209
0.9128	High Similarity	NPC209487
0.9122	High Similarity	NPC184136
0.9122	High Similarity	NPC338131
0.9122	High Similarity	NPC239363
0.9116	High Similarity	NPC195202
0.9116	High Similarity	NPC118726
0.9116	High Similarity	NPC12367
0.9103	High Similarity	NPC23955
0.9085	High Similarity	NPC167678
0.9085	High Similarity	NPC258331
0.9085	High Similarity	NPC266314
0.9085	High Similarity	NPC162668

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 NPC46941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	470
0.1-0.2	1022
0.2-0.3	1863
0.3-0.4	2676
0.4-0.5	1727
0.5-0.6	946
0.6-0.7	299
0.7-0.8	100
0.8-0.85	31
0.85-0.9	9
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9195	High Similarity	NPD2801	Approved
0.9128	High Similarity	NPD1934	Approved
0.8844	High Similarity	NPD1511	Approved
0.8816	High Similarity	NPD2393	Clinical (unspecified phase)
0.8725	High Similarity	NPD1512	Approved
0.8701	High Similarity	NPD3882	Suspended
0.8654	High Similarity	NPD5494	Approved
0.863	High Similarity	NPD1549	Phase 2
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8472	Intermediate Similarity	NPD447	Suspended
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8425	Intermediate Similarity	NPD1510	Phase 2
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1240	Approved
0.8397	Intermediate Similarity	NPD5402	Approved
0.8397	Intermediate Similarity	NPD3817	Phase 2
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1607	Approved
0.8282	Intermediate Similarity	NPD7054	Approved
0.8258	Intermediate Similarity	NPD4380	Phase 2
0.825	Intermediate Similarity	NPD1247	Approved
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8232	Intermediate Similarity	NPD7472	Approved
0.8217	Intermediate Similarity	NPD1465	Phase 2
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8151	Intermediate Similarity	NPD943	Approved
0.8125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2935	Discontinued
0.8121	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD1933	Approved
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8056	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1613	Approved
0.8027	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3750	Approved
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.7987	Intermediate Similarity	NPD6799	Approved
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7949	Intermediate Similarity	NPD5403	Approved
0.7947	Intermediate Similarity	NPD2346	Discontinued
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5401	Approved
0.7927	Intermediate Similarity	NPD3926	Phase 2
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD1203	Approved
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD919	Approved
0.7895	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3226	Approved
0.784	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7805	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD230	Phase 1
0.7727	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD9717	Approved
0.7697	Intermediate Similarity	NPD3748	Approved
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1653	Approved
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6099	Approved
0.7647	Intermediate Similarity	NPD6100	Approved
0.7616	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD920	Approved
0.7597	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD6844	Discontinued
0.7584	Intermediate Similarity	NPD3027	Phase 3
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7582	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7551	Intermediate Similarity	NPD1470	Approved
0.7533	Intermediate Similarity	NPD411	Approved
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2532	Approved
0.7484	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.745	Intermediate Similarity	NPD9494	Approved
0.7421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD2309	Approved
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD1201	Approved
0.7378	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD6234	Discontinued
0.7361	Intermediate Similarity	NPD1548	Phase 1
0.7358	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4625	Phase 3
0.7349	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD4967	Phase 2
0.7349	Intermediate Similarity	NPD4966	Approved
0.7347	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7326	Intermediate Similarity	NPD7286	Phase 2
0.7315	Intermediate Similarity	NPD2797	Approved
0.7303	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD4749	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7246	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6651	Approved
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD4307	Phase 2
0.7205	Intermediate Similarity	NPD4357	Discontinued
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD6190	Approved
0.7172	Intermediate Similarity	NPD5536	Phase 2
0.7168	Intermediate Similarity	NPD7228	Approved
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7549	Discontinued
0.7153	Intermediate Similarity	NPD6671	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7133	Intermediate Similarity	NPD3225	Approved
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7114	Intermediate Similarity	NPD1481	Phase 2
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3018	Phase 2
0.7103	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD3266	Approved
0.7083	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD5353	Approved
0.7078	Intermediate Similarity	NPD3764	Approved
0.7078	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6823	Phase 2
0.7055	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD4661	Approved
0.7052	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1535	Discovery
0.7044	Intermediate Similarity	NPD1471	Phase 3
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD5710	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7021	Intermediate Similarity	NPD7697	Approved
0.7021	Intermediate Similarity	NPD7698	Approved
0.7021	Intermediate Similarity	NPD7435	Discontinued
0.7021	Intermediate Similarity	NPD7696	Phase 3
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.7012	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD7685	Pre-registration
0.7006	Intermediate Similarity	NPD6386	Approved
0.6984	Remote Similarity	NPD7870	Phase 2
0.6984	Remote Similarity	NPD7871	Phase 2
0.698	Remote Similarity	NPD3496	Discontinued
0.6968	Remote Similarity	NPD1296	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