NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	586.28
Volume:	582.773
LogP:	3.862
LogD:	2.318
LogS:	-3.744
# Rotatable Bonds:	10
TPSA:	144.28
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.121
Synthetic Accessibility Score:	6.862
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.05
MDCK Permeability:	3.718998414115049e-05
Pgp-inhibitor:	0.131
Pgp-substrate:	0.397
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.308
30% Bioavailability (F30%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.403
Plasma Protein Binding (PPB):	77.39794158935547%
Volume Distribution (VD):	1.484
Pgp-substrate:	15.871408462524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.611
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	4.947
Half-life (T1/2):	0.624

ADMET: Toxicity

hERG Blockers:	0.806
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.591
Carcinogencity:	0.894
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC223351

Natural Product ID:	NPC223351
*Common Name:**	Swerilactone N
IUPAC Name:	5-[(1S)-1-hydroxy-3-oxobutyl]-3,4-dihydroisochromen-1-one
Synonyms:	Swerilactone N
Standard InCHIKey:	JUHKDTASENLCRJ-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-8(14)7-12(15)10-3-2-4-11-9(10)5-6-17-13(11)16/h2-4,12,15H,5-7H2,1H3/t12-/m0/s1
SMILES:	CC(=O)C[C@@H](c1cccc2c1CCOC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1817921
PubChem CID:	53494394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO31453	Swertia mileensis	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21823575]
NPO31453	Swertia mileensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8720386]
NPO25228	Corollospora pulchella	Species	Halosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9666182]
NPO31453	Swertia mileensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO31453	Swertia mileensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24661	Leontice leontopetalum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20828	Swertia leducii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31453	Swertia mileensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20828	Swertia leducii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24661	Leontice leontopetalum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21804	Dryopteris villarii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25228	Corollospora pulchella	Species	Halosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24875	Lithocarpus litseifolius	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25134	Cephalosporium chrysogenum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23166	Keteleeria evelyniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25070	Naranga aenescens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13483	Silene praemixta	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22424	Cetraria ornata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19759	Begonia fagifolia	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22085	Cercospora traversiana	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11200.1	Paenibacillus larvae subsp. pulvifaciens	Subspecies	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24468	Zanthoxylum macrophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2825	Chiloscyphus pallescens	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23292	Andrographis macrobotrys	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20828	Swertia leducii	Species	Gentianaceae	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	2
Others	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	510000.0	nM	PMID[467969]
NPT27	Others	Unspecified		CC50	>	510000.0	nM	PMID[467969]

☑ 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 NPC223351 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	258
0.1-0.2	1045
0.2-0.3	2641
0.3-0.4	6454
0.4-0.5	11487
0.5-0.6	8847
0.6-0.7	9110
0.7-0.8	2781
0.8-0.85	69
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC228739
0.9217	High Similarity	NPC306740
0.887	High Similarity	NPC210089
0.8559	High Similarity	NPC272524
0.8516	High Similarity	NPC82712
0.8409	Intermediate Similarity	NPC142027
0.8409	Intermediate Similarity	NPC27407
0.839	Intermediate Similarity	NPC167504
0.839	Intermediate Similarity	NPC260818
0.8358	Intermediate Similarity	NPC221104
0.8346	Intermediate Similarity	NPC291454
0.8333	Intermediate Similarity	NPC474363
0.8319	Intermediate Similarity	NPC321852
0.8319	Intermediate Similarity	NPC79496
0.8309	Intermediate Similarity	NPC470842
0.8264	Intermediate Similarity	NPC474685
0.8244	Intermediate Similarity	NPC470831
0.8244	Intermediate Similarity	NPC214702
0.822	Intermediate Similarity	NPC83628
0.822	Intermediate Similarity	NPC265407
0.822	Intermediate Similarity	NPC85493
0.8197	Intermediate Similarity	NPC149691
0.8195	Intermediate Similarity	NPC477893
0.8189	Intermediate Similarity	NPC472704
0.8182	Intermediate Similarity	NPC153053
0.8182	Intermediate Similarity	NPC87069
0.8167	Intermediate Similarity	NPC158282
0.8154	Intermediate Similarity	NPC473744
0.814	Intermediate Similarity	NPC110211
0.814	Intermediate Similarity	NPC472706
0.8125	Intermediate Similarity	NPC246166
0.8125	Intermediate Similarity	NPC184219
0.8125	Intermediate Similarity	NPC295664
0.811	Intermediate Similarity	NPC472703
0.8088	Intermediate Similarity	NPC126739
0.8088	Intermediate Similarity	NPC197666
0.8083	Intermediate Similarity	NPC476003
0.8083	Intermediate Similarity	NPC474157
0.808	Intermediate Similarity	NPC204784
0.8062	Intermediate Similarity	NPC275576
0.806	Intermediate Similarity	NPC477896
0.8051	Intermediate Similarity	NPC119271
0.8049	Intermediate Similarity	NPC100353
0.8043	Intermediate Similarity	NPC472605
0.8043	Intermediate Similarity	NPC472604
0.8043	Intermediate Similarity	NPC472603
0.8033	Intermediate Similarity	NPC307651
0.8033	Intermediate Similarity	NPC477411
0.8033	Intermediate Similarity	NPC172525
0.8029	Intermediate Similarity	NPC88269
0.8017	Intermediate Similarity	NPC284477
0.8015	Intermediate Similarity	NPC301915
0.8015	Intermediate Similarity	NPC261292
0.8	Intermediate Similarity	NPC253681
0.8	Intermediate Similarity	NPC169913
0.8	Intermediate Similarity	NPC42540
0.8	Intermediate Similarity	NPC151607
0.8	Intermediate Similarity	NPC27633
0.8	Intermediate Similarity	NPC94298
0.8	Intermediate Similarity	NPC204579
0.7985	Intermediate Similarity	NPC310662
0.7983	Intermediate Similarity	NPC56493
0.7983	Intermediate Similarity	NPC20485
0.7971	Intermediate Similarity	NPC472600
0.7971	Intermediate Similarity	NPC472601
0.797	Intermediate Similarity	NPC473777
0.7969	Intermediate Similarity	NPC67300
0.7969	Intermediate Similarity	NPC65627
0.7966	Intermediate Similarity	NPC209632
0.7956	Intermediate Similarity	NPC61590
0.7955	Intermediate Similarity	NPC262819
0.7949	Intermediate Similarity	NPC301943
0.7949	Intermediate Similarity	NPC474365
0.7941	Intermediate Similarity	NPC235115
0.7939	Intermediate Similarity	NPC115797
0.7939	Intermediate Similarity	NPC51448
0.7929	Intermediate Similarity	NPC159721
0.7929	Intermediate Similarity	NPC471731
0.7926	Intermediate Similarity	NPC474097
0.7923	Intermediate Similarity	NPC49938
0.7923	Intermediate Similarity	NPC236405
0.7923	Intermediate Similarity	NPC79608
0.7923	Intermediate Similarity	NPC476033
0.7917	Intermediate Similarity	NPC469636
0.7917	Intermediate Similarity	NPC10251
0.7917	Intermediate Similarity	NPC17417
0.7914	Intermediate Similarity	NPC149533
0.7913	Intermediate Similarity	NPC229242
0.791	Intermediate Similarity	NPC477407
0.791	Intermediate Similarity	NPC302844
0.7907	Intermediate Similarity	NPC85511
0.7907	Intermediate Similarity	NPC138798
0.7903	Intermediate Similarity	NPC135730
0.7903	Intermediate Similarity	NPC226093
0.7899	Intermediate Similarity	NPC216312
0.7899	Intermediate Similarity	NPC242355
0.7899	Intermediate Similarity	NPC299405
0.7899	Intermediate Similarity	NPC268052
0.7899	Intermediate Similarity	NPC471602
0.7899	Intermediate Similarity	NPC256463
0.7899	Intermediate Similarity	NPC295339
0.7899	Intermediate Similarity	NPC306835
0.7899	Intermediate Similarity	NPC111422
0.7899	Intermediate Similarity	NPC476477
0.7899	Intermediate Similarity	NPC29771
0.7895	Intermediate Similarity	NPC72915
0.7887	Intermediate Similarity	NPC473023
0.7886	Intermediate Similarity	NPC308744
0.7886	Intermediate Similarity	NPC196673
0.7886	Intermediate Similarity	NPC237366
0.7881	Intermediate Similarity	NPC31786
0.7881	Intermediate Similarity	NPC114594
0.7874	Intermediate Similarity	NPC133302
0.7869	Intermediate Similarity	NPC474314
0.7869	Intermediate Similarity	NPC270699
0.7869	Intermediate Similarity	NPC82899
0.7868	Intermediate Similarity	NPC472372
0.7868	Intermediate Similarity	NPC472374
0.7868	Intermediate Similarity	NPC470844
0.7857	Intermediate Similarity	NPC471733
0.7852	Intermediate Similarity	NPC43627
0.7852	Intermediate Similarity	NPC126516
0.7852	Intermediate Similarity	NPC48929
0.7851	Intermediate Similarity	NPC196246
0.7851	Intermediate Similarity	NPC93084
0.7851	Intermediate Similarity	NPC214067
0.7851	Intermediate Similarity	NPC251854
0.7851	Intermediate Similarity	NPC174099
0.7845	Intermediate Similarity	NPC228435
0.7842	Intermediate Similarity	NPC32749
0.7842	Intermediate Similarity	NPC155205
0.7842	Intermediate Similarity	NPC42262
0.7842	Intermediate Similarity	NPC182869
0.7842	Intermediate Similarity	NPC147542
0.7842	Intermediate Similarity	NPC327916
0.7842	Intermediate Similarity	NPC220496
0.7842	Intermediate Similarity	NPC37992
0.7842	Intermediate Similarity	NPC241349
0.784	Intermediate Similarity	NPC158157
0.784	Intermediate Similarity	NPC131192
0.7833	Intermediate Similarity	NPC211439
0.7826	Intermediate Similarity	NPC476643
0.7826	Intermediate Similarity	NPC249912
0.7826	Intermediate Similarity	NPC212693
0.7826	Intermediate Similarity	NPC94248
0.7826	Intermediate Similarity	NPC472602
0.7826	Intermediate Similarity	NPC191835
0.7826	Intermediate Similarity	NPC92754
0.7826	Intermediate Similarity	NPC276775
0.7826	Intermediate Similarity	NPC478200
0.7826	Intermediate Similarity	NPC33144
0.7823	Intermediate Similarity	NPC210092
0.7823	Intermediate Similarity	NPC474095
0.782	Intermediate Similarity	NPC27712
0.7812	Intermediate Similarity	NPC472981
0.7805	Intermediate Similarity	NPC128368
0.7805	Intermediate Similarity	NPC13784
0.7805	Intermediate Similarity	NPC474176
0.7803	Intermediate Similarity	NPC121104
0.7801	Intermediate Similarity	NPC127857
0.7801	Intermediate Similarity	NPC478202
0.7801	Intermediate Similarity	NPC476473
0.7801	Intermediate Similarity	NPC469542
0.7801	Intermediate Similarity	NPC472610
0.7797	Intermediate Similarity	NPC255676
0.7797	Intermediate Similarity	NPC60679
0.7797	Intermediate Similarity	NPC89886
0.7787	Intermediate Similarity	NPC305912
0.7787	Intermediate Similarity	NPC1082
0.7786	Intermediate Similarity	NPC472035
0.7786	Intermediate Similarity	NPC95449
0.7786	Intermediate Similarity	NPC158634
0.7786	Intermediate Similarity	NPC184053
0.7786	Intermediate Similarity	NPC53649
0.7786	Intermediate Similarity	NPC313123
0.7786	Intermediate Similarity	NPC478201
0.7786	Intermediate Similarity	NPC477894
0.7786	Intermediate Similarity	NPC257003
0.7786	Intermediate Similarity	NPC478217
0.7786	Intermediate Similarity	NPC471444
0.7778	Intermediate Similarity	NPC42211
0.7778	Intermediate Similarity	NPC197037
0.777	Intermediate Similarity	NPC473988
0.777	Intermediate Similarity	NPC32360
0.777	Intermediate Similarity	NPC77493
0.777	Intermediate Similarity	NPC105456
0.777	Intermediate Similarity	NPC213567
0.777	Intermediate Similarity	NPC52358
0.777	Intermediate Similarity	NPC139634
0.7769	Intermediate Similarity	NPC99846
0.7769	Intermediate Similarity	NPC269023
0.7769	Intermediate Similarity	NPC318327
0.7762	Intermediate Similarity	NPC250046
0.7762	Intermediate Similarity	NPC60509
0.7762	Intermediate Similarity	NPC81698
0.7761	Intermediate Similarity	NPC473271
0.7761	Intermediate Similarity	NPC109778
0.776	Intermediate Similarity	NPC471616
0.7759	Intermediate Similarity	NPC225060
0.7759	Intermediate Similarity	NPC78701

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 NPC223351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	793
0.2-0.3	1415
0.3-0.4	2563
0.4-0.5	2444
0.5-0.6	1183
0.6-0.7	471
0.7-0.8	64
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8083	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9545	Approved
0.7917	Intermediate Similarity	NPD2182	Approved
0.7881	Intermediate Similarity	NPD164	Approved
0.7863	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD1237	Approved
0.7724	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1238	Approved
0.7687	Intermediate Similarity	NPD7008	Discontinued
0.7667	Intermediate Similarity	NPD5048	Discontinued
0.7589	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5951	Approved
0.754	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4628	Phase 3
0.7517	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD1929	Approved
0.75	Intermediate Similarity	NPD1930	Approved
0.75	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6010	Discontinued
0.7447	Intermediate Similarity	NPD2346	Discontinued
0.7422	Intermediate Similarity	NPD9493	Approved
0.7394	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1549	Phase 2
0.7383	Intermediate Similarity	NPD7411	Suspended
0.7365	Intermediate Similarity	NPD3226	Approved
0.736	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6647	Phase 2
0.7333	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6085	Phase 2
0.7328	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD9495	Approved
0.731	Intermediate Similarity	NPD7236	Approved
0.7304	Intermediate Similarity	NPD9256	Approved
0.7304	Intermediate Similarity	NPD9258	Approved
0.7285	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1240	Approved
0.7266	Intermediate Similarity	NPD2629	Approved
0.7266	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7075	Discontinued
0.7246	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6801	Discontinued
0.7211	Intermediate Similarity	NPD2533	Approved
0.7211	Intermediate Similarity	NPD2532	Approved
0.7211	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1510	Phase 2
0.7183	Intermediate Similarity	NPD2799	Discontinued
0.7172	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1608	Approved
0.7164	Intermediate Similarity	NPD9717	Approved
0.7163	Intermediate Similarity	NPD1607	Approved
0.7132	Intermediate Similarity	NPD1470	Approved
0.712	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1202	Approved
0.7107	Intermediate Similarity	NPD2066	Phase 3
0.7092	Intermediate Similarity	NPD230	Phase 1
0.709	Intermediate Similarity	NPD1201	Approved
0.709	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6287	Discontinued
0.7083	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD5125	Phase 3
0.7067	Intermediate Similarity	NPD7239	Suspended
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3750	Approved
0.7027	Intermediate Similarity	NPD6799	Approved
0.702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5909	Discontinued
0.7014	Intermediate Similarity	NPD2935	Discontinued
0.7014	Intermediate Similarity	NPD1551	Phase 2
0.7013	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1203	Approved
0.6985	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6599	Discontinued
0.6966	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD9259	Approved
0.6948	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.694	Remote Similarity	NPD17	Approved
0.6934	Remote Similarity	NPD1283	Approved
0.6928	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7741	Discontinued
0.6897	Remote Similarity	NPD5404	Approved
0.6897	Remote Similarity	NPD2796	Approved
0.6897	Remote Similarity	NPD5408	Approved
0.6897	Remote Similarity	NPD5405	Approved
0.6897	Remote Similarity	NPD5406	Approved
0.6894	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7799	Discontinued
0.6887	Remote Similarity	NPD5403	Approved
0.6887	Remote Similarity	NPD920	Approved
0.6884	Remote Similarity	NPD1164	Approved
0.6875	Remote Similarity	NPD2569	Approved
0.6875	Remote Similarity	NPD2567	Approved
0.6875	Remote Similarity	NPD2067	Discontinued
0.6871	Remote Similarity	NPD1243	Approved
0.6867	Remote Similarity	NPD5401	Approved
0.6866	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5157	Phase 1
0.6861	Remote Similarity	NPD5159	Phase 2
0.6859	Remote Similarity	NPD7768	Phase 2
0.6857	Remote Similarity	NPD6832	Phase 2
0.6855	Remote Similarity	NPD1932	Approved
0.685	Remote Similarity	NPD9264	Approved
0.685	Remote Similarity	NPD9267	Approved
0.685	Remote Similarity	NPD9263	Approved
0.6849	Remote Similarity	NPD6005	Phase 3
0.6849	Remote Similarity	NPD6002	Phase 3
0.6849	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6004	Phase 3
0.6849	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2798	Approved
0.6828	Remote Similarity	NPD3748	Approved
0.6824	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD6273	Approved
0.6815	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9266	Approved
0.6797	Remote Similarity	NPD7458	Discontinued
0.6797	Remote Similarity	NPD74	Approved
0.6794	Remote Similarity	NPD1241	Discontinued
0.6792	Remote Similarity	NPD6959	Discontinued
0.6788	Remote Similarity	NPD3972	Approved
0.6788	Remote Similarity	NPD6637	Approved
0.6777	Remote Similarity	NPD1693	Approved
0.6774	Remote Similarity	NPD1934	Approved
0.6765	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3268	Approved
0.6757	Remote Similarity	NPD2800	Approved
0.6755	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7057	Phase 3
0.6752	Remote Similarity	NPD7058	Phase 2
0.675	Remote Similarity	NPD6232	Discontinued
0.675	Remote Similarity	NPD5711	Approved
0.675	Remote Similarity	NPD5710	Approved
0.6747	Remote Similarity	NPD8312	Approved
0.6747	Remote Similarity	NPD8313	Approved
0.6738	Remote Similarity	NPD2613	Approved
0.6735	Remote Similarity	NPD2344	Approved
0.6735	Remote Similarity	NPD1471	Phase 3
0.6728	Remote Similarity	NPD7473	Discontinued
0.6727	Remote Similarity	NPD8368	Discontinued
0.6723	Remote Similarity	NPD1089	Approved
0.6723	Remote Similarity	NPD1086	Approved
0.6723	Remote Similarity	NPD1090	Approved
0.6721	Remote Similarity	NPD1989	Approved
0.6715	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1281	Approved
0.6714	Remote Similarity	NPD5647	Approved
0.6714	Remote Similarity	NPD1019	Discontinued
0.6713	Remote Similarity	NPD520	Approved
0.6712	Remote Similarity	NPD7305	Phase 1
0.6711	Remote Similarity	NPD2575	Approved
0.6696	Remote Similarity	NPD9491	Approved
0.6692	Remote Similarity	NPD4198	Discontinued
0.6691	Remote Similarity	NPD2198	Approved
0.6691	Remote Similarity	NPD1876	Approved
0.6691	Remote Similarity	NPD2199	Approved
0.6691	Remote Similarity	NPD5305	Approved
0.6691	Remote Similarity	NPD5306	Approved
0.669	Remote Similarity	NPD6651	Approved
0.6687	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD1239	Approved
0.6646	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2797	Approved
0.6643	Remote Similarity	NPD411	Approved
0.6642	Remote Similarity	NPD4136	Approved
0.6642	Remote Similarity	NPD4106	Approved
0.6642	Remote Similarity	NPD4135	Approved
0.6642	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6685	Approved
0.6639	Remote Similarity	NPD800	Approved
0.6627	Remote Similarity	NPD8434	Phase 2
0.6621	Remote Similarity	NPD5124	Phase 1
0.6621	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD447	Suspended
0.6617	Remote Similarity	NPD9281	Approved

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