NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	259.266
LogP:	3.016
LogD:	2.771
LogS:	-4.684
# Rotatable Bonds:	1
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	2.325
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.701
MDCK Permeability:	3.565646693459712e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	87.47007751464844%
Volume Distribution (VD):	0.872
Pgp-substrate:	10.582889556884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.697
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.65
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	6.645
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.741
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.412
Carcinogencity:	0.952
Eye Corrosion:	0.008
Eye Irritation:	0.391
Respiratory Toxicity:	0.548

Download Data

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

Natural Product: NPC244371

Natural Product ID:	NPC244371
*Common Name:**	4-Methoxy-2,3-Methylenedioxyxanthone
IUPAC Name:	4-methoxy-[1,3]dioxolo[4,5-b]xanthen-10-one
Synonyms:
Standard InCHIKey:	VVUQORLQHOKQDW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O5/c1-17-15-13-9(6-11-14(15)19-7-18-11)12(16)8-4-2-3-5-10(8)20-13/h2-6H,7H2,1H3
SMILES:	COc1c2OCOc2cc2c1oc1ccccc1c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2029862
PubChem CID:	70687907
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
NPO32798	polygala karensium	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22552195]

☑ 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	2
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	>	100.0	ug.mL-1	PMID[566548]
NPT2	Others	Unspecified		Ratio IC50	=	243.0	n.a.	PMID[566548]

☑ 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 NPC244371 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	571
0.1-0.2	2222
0.2-0.3	5502
0.3-0.4	11402
0.4-0.5	5750
0.5-0.6	4190
0.6-0.7	5951
0.7-0.8	4699
0.8-0.85	1502
0.85-0.9	716
0.9-0.95	172
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC258644
0.9662	High Similarity	NPC292460
0.9542	High Similarity	NPC478199
0.953	High Similarity	NPC153008
0.953	High Similarity	NPC148497
0.9521	High Similarity	NPC231013
0.9477	High Similarity	NPC162668
0.9467	High Similarity	NPC478213
0.9452	High Similarity	NPC224687
0.94	High Similarity	NPC68882
0.9392	High Similarity	NPC63256
0.9392	High Similarity	NPC10304
0.9346	High Similarity	NPC257914
0.9346	High Similarity	NPC238405
0.9346	High Similarity	NPC104459
0.9342	High Similarity	NPC155063
0.9338	High Similarity	NPC279930
0.9338	High Similarity	NPC57211
0.9333	High Similarity	NPC279061
0.929	High Similarity	NPC273021
0.929	High Similarity	NPC18284
0.929	High Similarity	NPC469575
0.9286	High Similarity	NPC131557
0.9281	High Similarity	NPC310206
0.9276	High Similarity	NPC284353
0.9276	High Similarity	NPC478238
0.9272	High Similarity	NPC52623
0.9236	High Similarity	NPC113093
0.9231	High Similarity	NPC470178
0.9226	High Similarity	NPC34376
0.9221	High Similarity	NPC215375
0.9221	High Similarity	NPC62518
0.9205	High Similarity	NPC149614
0.92	High Similarity	NPC238366
0.9195	High Similarity	NPC205522
0.9189	High Similarity	NPC296575
0.9172	High Similarity	NPC187923
0.9156	High Similarity	NPC167595
0.9139	High Similarity	NPC179183
0.9128	High Similarity	NPC40818
0.9128	High Similarity	NPC110639
0.9128	High Similarity	NPC106461
0.9128	High Similarity	NPC215932
0.9128	High Similarity	NPC14958
0.9108	High Similarity	NPC110257
0.9103	High Similarity	NPC260640
0.9103	High Similarity	NPC295009
0.9097	High Similarity	NPC113055
0.9091	High Similarity	NPC301897
0.9085	High Similarity	NPC271779
0.9085	High Similarity	NPC206238
0.9085	High Similarity	NPC292214
0.9085	High Similarity	NPC186507
0.9085	High Similarity	NPC167091
0.9085	High Similarity	NPC88645
0.9079	High Similarity	NPC474663
0.9079	High Similarity	NPC117579
0.9079	High Similarity	NPC198615
0.9067	High Similarity	NPC85233
0.906	High Similarity	NPC136278
0.9057	High Similarity	NPC42892
0.9057	High Similarity	NPC135345
0.9045	High Similarity	NPC125991
0.9045	High Similarity	NPC302741
0.9038	High Similarity	NPC269906
0.9038	High Similarity	NPC285973
0.9038	High Similarity	NPC298093
0.9038	High Similarity	NPC225624
0.9032	High Similarity	NPC19097
0.9026	High Similarity	NPC18954
0.902	High Similarity	NPC120537
0.902	High Similarity	NPC161277
0.902	High Similarity	NPC166201
0.902	High Similarity	NPC199100
0.902	High Similarity	NPC101996
0.902	High Similarity	NPC180234
0.902	High Similarity	NPC39007
0.9013	High Similarity	NPC29056
0.9012	High Similarity	NPC66804
0.9006	High Similarity	NPC223375
0.9006	High Similarity	NPC475825
0.9	High Similarity	NPC302408
0.9	High Similarity	NPC120924
0.9	High Similarity	NPC283002
0.9	High Similarity	NPC195919
0.9	High Similarity	NPC216314
0.8993	High Similarity	NPC293201
0.8993	High Similarity	NPC113089
0.8993	High Similarity	NPC23955
0.8981	High Similarity	NPC94155
0.8961	High Similarity	NPC472915
0.8961	High Similarity	NPC472408
0.8957	High Similarity	NPC156635
0.8954	High Similarity	NPC171010
0.8954	High Similarity	NPC251110
0.8951	High Similarity	NPC72455
0.8947	High Similarity	NPC474648
0.8947	High Similarity	NPC69752
0.8944	High Similarity	NPC44558
0.8944	High Similarity	NPC105511
0.8944	High Similarity	NPC212748
0.894	High Similarity	NPC46941
0.894	High Similarity	NPC117463
0.894	High Similarity	NPC470511
0.8938	High Similarity	NPC76482
0.8933	High Similarity	NPC165512
0.8933	High Similarity	NPC471590
0.8926	High Similarity	NPC70853
0.8926	High Similarity	NPC9966
0.8919	High Similarity	NPC58229
0.891	High Similarity	NPC210084
0.891	High Similarity	NPC181960
0.891	High Similarity	NPC99597
0.8903	High Similarity	NPC472909
0.8903	High Similarity	NPC37392
0.8903	High Similarity	NPC2928
0.8896	High Similarity	NPC35544
0.8896	High Similarity	NPC104728
0.8889	High Similarity	NPC475155
0.8889	High Similarity	NPC307518
0.8889	High Similarity	NPC61620
0.8889	High Similarity	NPC29231
0.8889	High Similarity	NPC475964
0.8889	High Similarity	NPC62042
0.8889	High Similarity	NPC205076
0.8889	High Similarity	NPC306821
0.8889	High Similarity	NPC48773
0.8889	High Similarity	NPC248102
0.8889	High Similarity	NPC259058
0.8889	High Similarity	NPC234152
0.8889	High Similarity	NPC201547
0.8882	High Similarity	NPC41853
0.8882	High Similarity	NPC476342
0.8882	High Similarity	NPC211309
0.8882	High Similarity	NPC472381
0.8882	High Similarity	NPC183236
0.8882	High Similarity	NPC472383
0.8867	High Similarity	NPC182842
0.8859	High Similarity	NPC29536
0.8859	High Similarity	NPC214919
0.8859	High Similarity	NPC124467
0.8854	High Similarity	NPC16935
0.8846	High Similarity	NPC235165
0.8846	High Similarity	NPC255106
0.8846	High Similarity	NPC45131
0.8846	High Similarity	NPC472916
0.8846	High Similarity	NPC303255
0.8839	High Similarity	NPC128961
0.8839	High Similarity	NPC280937
0.8831	High Similarity	NPC226973
0.8831	High Similarity	NPC208043
0.8831	High Similarity	NPC308451
0.8827	High Similarity	NPC34287
0.8827	High Similarity	NPC474434
0.8827	High Similarity	NPC21190
0.8827	High Similarity	NPC293004
0.8827	High Similarity	NPC22195
0.8827	High Similarity	NPC183357
0.8827	High Similarity	NPC471416
0.8827	High Similarity	NPC224462
0.8824	High Similarity	NPC294502
0.8824	High Similarity	NPC200221
0.8824	High Similarity	NPC181250
0.882	High Similarity	NPC93099
0.882	High Similarity	NPC167479
0.8816	High Similarity	NPC299923
0.8812	High Similarity	NPC165720
0.879	High Similarity	NPC474208
0.879	High Similarity	NPC474836
0.879	High Similarity	NPC78225
0.879	High Similarity	NPC36852
0.879	High Similarity	NPC472913
0.879	High Similarity	NPC476981
0.879	High Similarity	NPC262286
0.879	High Similarity	NPC472910
0.879	High Similarity	NPC475267
0.879	High Similarity	NPC48208
0.879	High Similarity	NPC472914
0.879	High Similarity	NPC245758
0.879	High Similarity	NPC472911
0.879	High Similarity	NPC474990
0.879	High Similarity	NPC162869
0.879	High Similarity	NPC96167
0.879	High Similarity	NPC222814
0.879	High Similarity	NPC156057
0.8788	High Similarity	NPC67302
0.8782	High Similarity	NPC34725
0.8782	High Similarity	NPC31018
0.8782	High Similarity	NPC256612
0.8782	High Similarity	NPC276059
0.8782	High Similarity	NPC255807
0.8782	High Similarity	NPC122623
0.8782	High Similarity	NPC241774
0.8782	High Similarity	NPC20830
0.878	High Similarity	NPC290304
0.878	High Similarity	NPC236327
0.878	High Similarity	NPC472607
0.8774	High Similarity	NPC222830
0.8774	High Similarity	NPC275722
0.8774	High Similarity	NPC256283

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 NPC244371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1026
0.2-0.3	1976
0.3-0.4	2739
0.4-0.5	1688
0.5-0.6	827
0.6-0.7	292
0.7-0.8	98
0.8-0.85	22
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD5494	Approved
0.882	High Similarity	NPD3818	Discontinued
0.8718	High Similarity	NPD2801	Approved
0.8693	High Similarity	NPD6980	Clinical (unspecified phase)
0.8654	High Similarity	NPD1934	Approved
0.8625	High Similarity	NPD1247	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8485	Intermediate Similarity	NPD7074	Phase 3
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD3817	Phase 2
0.8424	Intermediate Similarity	NPD7054	Approved
0.8385	Intermediate Similarity	NPD919	Approved
0.8377	Intermediate Similarity	NPD1511	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8269	Intermediate Similarity	NPD1512	Approved
0.8255	Intermediate Similarity	NPD1933	Approved
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.817	Intermediate Similarity	NPD1549	Phase 2
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD920	Approved
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8025	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1243	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1510	Phase 2
0.7947	Intermediate Similarity	NPD1240	Approved
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7911	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7866	Intermediate Similarity	NPD5402	Approved
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7843	Intermediate Similarity	NPD1607	Approved
0.784	Intermediate Similarity	NPD6599	Discontinued
0.784	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD3749	Approved
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6801	Discontinued
0.7742	Intermediate Similarity	NPD3748	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.7607	Intermediate Similarity	NPD1653	Approved
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD4966	Approved
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1551	Phase 2
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5242	Approved
0.7439	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7427	Intermediate Similarity	NPD6959	Discontinued
0.7423	Intermediate Similarity	NPD2532	Approved
0.7423	Intermediate Similarity	NPD2534	Approved
0.7423	Intermediate Similarity	NPD2533	Approved
0.7421	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7399	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD5005	Approved
0.738	Intermediate Similarity	NPD5006	Approved
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3226	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7337	Intermediate Similarity	NPD5353	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2798	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7312	Intermediate Similarity	NPD1471	Phase 3
0.7299	Intermediate Similarity	NPD2403	Approved
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7294	Intermediate Similarity	NPD7768	Phase 2
0.7262	Intermediate Similarity	NPD6385	Approved
0.7262	Intermediate Similarity	NPD6386	Approved
0.7258	Intermediate Similarity	NPD4420	Approved
0.7247	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD2654	Approved
0.72	Intermediate Similarity	NPD17	Approved
0.7193	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7105	Intermediate Similarity	NPD3705	Approved
0.7097	Intermediate Similarity	NPD1019	Discontinued
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7079	Intermediate Similarity	NPD7286	Phase 2
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7044	Intermediate Similarity	NPD4307	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD6099	Approved
0.7037	Intermediate Similarity	NPD6100	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7018	Intermediate Similarity	NPD6844	Discontinued
0.7017	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5710	Approved
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD8151	Discontinued
0.697	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3027	Phase 3
0.6959	Remote Similarity	NPD7584	Approved
0.6959	Remote Similarity	NPD1241	Discontinued
0.6948	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD3018	Phase 2
0.6936	Remote Similarity	NPD5978	Approved
0.6936	Remote Similarity	NPD5977	Approved
0.6928	Remote Similarity	NPD6190	Approved
0.6927	Remote Similarity	NPD6823	Phase 2
0.6927	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7701	Phase 2
0.6919	Remote Similarity	NPD6280	Approved
0.6919	Remote Similarity	NPD6279	Approved
0.6918	Remote Similarity	NPD411	Approved
0.6915	Remote Similarity	NPD6534	Approved
0.6915	Remote Similarity	NPD6535	Approved
0.691	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9268	Approved
0.6905	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7783	Phase 2
0.6904	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7028	Phase 2
0.6893	Remote Similarity	NPD6808	Phase 2
0.689	Remote Similarity	NPD2353	Approved
0.689	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1610	Phase 2
0.6882	Remote Similarity	NPD4287	Approved
0.6879	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD7033	Discontinued
0.6871	Remote Similarity	NPD4308	Phase 3
0.6859	Remote Similarity	NPD1876	Approved
0.6853	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6651	Approved
0.6845	Remote Similarity	NPD4357	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