NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	238.27
LogP:	1.513
LogD:	1.167
LogS:	-2.82
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	3.116
Fsp3:	0.385
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:	-4.598
MDCK Permeability:	2.9710334274568595e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.833
Plasma Protein Binding (PPB):	56.36800003051758%
Volume Distribution (VD):	0.801
Pgp-substrate:	50.785911560058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.161
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.579
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	7.492
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.149
Carcinogencity:	0.029
Eye Corrosion:	0.005
Eye Irritation:	0.329
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC228739

Natural Product ID:	NPC228739
*Common Name:**	Swerilactone M
IUPAC Name:	7-acetyl-5-[(1S)-1-hydroxyethyl]-3,4-dihydroisochromen-1-one
Synonyms:	Swerilactone M
Standard InCHIKey:	DGTOBGOQSPGHCS-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-7(14)9-5-11(8(2)15)10-3-4-17-13(16)12(10)6-9/h5-6,8,15H,3-4H2,1-2H3/t8-/m0/s1
SMILES:	CC(=O)c1cc([C@@H](O)C)c2c(c1)C(=O)OCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1817920
PubChem CID:	53483971
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	3

Activity Type	# Activity
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.0	n.a.	PMID[542521]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.53	n.a.	PMID[542521]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1200000.0	nM	PMID[542521]
NPT27	Others	Unspecified		CC50	=	1840000.0	nM	PMID[542521]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	2690000.0	nM	PMID[542521]

☑ 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 NPC228739 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	264
0.1-0.2	1090
0.2-0.3	2767
0.3-0.4	6758
0.4-0.5	12115
0.5-0.6	9403
0.6-0.7	8694
0.7-0.8	1581
0.8-0.85	20
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC223351
0.8974	High Similarity	NPC306740
0.8632	High Similarity	NPC210089
0.8594	High Similarity	NPC82712
0.8333	Intermediate Similarity	NPC272524
0.8319	Intermediate Similarity	NPC167504
0.8268	Intermediate Similarity	NPC85511
0.8211	Intermediate Similarity	NPC158157
0.8197	Intermediate Similarity	NPC476357
0.8167	Intermediate Similarity	NPC260818
0.811	Intermediate Similarity	NPC167323
0.811	Intermediate Similarity	NPC269923
0.8099	Intermediate Similarity	NPC321852
0.8099	Intermediate Similarity	NPC79496
0.8077	Intermediate Similarity	NPC253681
0.8062	Intermediate Similarity	NPC295664
0.806	Intermediate Similarity	NPC310662
0.8049	Intermediate Similarity	NPC474095
0.8049	Intermediate Similarity	NPC474685
0.8029	Intermediate Similarity	NPC221104
0.8016	Intermediate Similarity	NPC204784
0.8015	Intermediate Similarity	NPC115797
0.8015	Intermediate Similarity	NPC51448
0.8	Intermediate Similarity	NPC265407
0.8	Intermediate Similarity	NPC85493
0.8	Intermediate Similarity	NPC83628
0.8	Intermediate Similarity	NPC477893
0.7986	Intermediate Similarity	NPC470842
0.7984	Intermediate Similarity	NPC472704
0.7984	Intermediate Similarity	NPC135730
0.7967	Intermediate Similarity	NPC153053
0.7967	Intermediate Similarity	NPC477411
0.7967	Intermediate Similarity	NPC196673
0.7955	Intermediate Similarity	NPC473744
0.7951	Intermediate Similarity	NPC158282
0.7949	Intermediate Similarity	NPC284477
0.7941	Intermediate Similarity	NPC27407
0.7941	Intermediate Similarity	NPC142027
0.7939	Intermediate Similarity	NPC110211
0.7939	Intermediate Similarity	NPC472706
0.7923	Intermediate Similarity	NPC184219
0.7923	Intermediate Similarity	NPC246166
0.7907	Intermediate Similarity	NPC472703
0.7899	Intermediate Similarity	NPC476643
0.7891	Intermediate Similarity	NPC472981
0.7886	Intermediate Similarity	NPC13784
0.7883	Intermediate Similarity	NPC291454
0.7872	Intermediate Similarity	NPC471731
0.7872	Intermediate Similarity	NPC159721
0.7869	Intermediate Similarity	NPC474157
0.7869	Intermediate Similarity	NPC476003
0.7868	Intermediate Similarity	NPC477896
0.7863	Intermediate Similarity	NPC275576
0.7857	Intermediate Similarity	NPC228318
0.7857	Intermediate Similarity	NPC149533
0.7852	Intermediate Similarity	NPC477407
0.7851	Intermediate Similarity	NPC318327
0.784	Intermediate Similarity	NPC226093
0.784	Intermediate Similarity	NPC100353
0.7836	Intermediate Similarity	NPC72915
0.7833	Intermediate Similarity	NPC119271
0.7826	Intermediate Similarity	NPC119542
0.7823	Intermediate Similarity	NPC474363
0.7823	Intermediate Similarity	NPC307651
0.7817	Intermediate Similarity	NPC151607
0.7817	Intermediate Similarity	NPC42540
0.7812	Intermediate Similarity	NPC133302
0.781	Intermediate Similarity	NPC472372
0.781	Intermediate Similarity	NPC472374
0.7805	Intermediate Similarity	NPC66208
0.7803	Intermediate Similarity	NPC169913
0.7803	Intermediate Similarity	NPC204579
0.7801	Intermediate Similarity	NPC471733
0.7797	Intermediate Similarity	NPC25458
0.7795	Intermediate Similarity	NPC27633
0.7795	Intermediate Similarity	NPC94298
0.7794	Intermediate Similarity	NPC48929
0.7794	Intermediate Similarity	NPC126516
0.7793	Intermediate Similarity	NPC247219
0.7778	Intermediate Similarity	NPC214702
0.7778	Intermediate Similarity	NPC228435
0.7778	Intermediate Similarity	NPC473777
0.7778	Intermediate Similarity	NPC470831
0.7769	Intermediate Similarity	NPC56493
0.7769	Intermediate Similarity	NPC67300
0.776	Intermediate Similarity	NPC186933
0.776	Intermediate Similarity	NPC228936
0.775	Intermediate Similarity	NPC209632
0.7742	Intermediate Similarity	NPC128368
0.7737	Intermediate Similarity	NPC474097
0.7734	Intermediate Similarity	NPC472708
0.7731	Intermediate Similarity	NPC301943
0.7731	Intermediate Similarity	NPC474365
0.773	Intermediate Similarity	NPC477894
0.773	Intermediate Similarity	NPC37530
0.773	Intermediate Similarity	NPC472604
0.773	Intermediate Similarity	NPC472603
0.773	Intermediate Similarity	NPC472605
0.7727	Intermediate Similarity	NPC49938
0.7724	Intermediate Similarity	NPC474057
0.7721	Intermediate Similarity	NPC302844
0.7714	Intermediate Similarity	NPC26924
0.7714	Intermediate Similarity	NPC88269
0.7712	Intermediate Similarity	NPC70624
0.7708	Intermediate Similarity	NPC471346
0.7705	Intermediate Similarity	NPC10251
0.7705	Intermediate Similarity	NPC17417
0.7705	Intermediate Similarity	NPC469636
0.7698	Intermediate Similarity	NPC149691
0.7698	Intermediate Similarity	NPC245058
0.7692	Intermediate Similarity	NPC293831
0.7692	Intermediate Similarity	NPC229242
0.7692	Intermediate Similarity	NPC260152
0.7692	Intermediate Similarity	NPC369
0.768	Intermediate Similarity	NPC196075
0.768	Intermediate Similarity	NPC237366
0.768	Intermediate Similarity	NPC471721
0.768	Intermediate Similarity	NPC308744
0.768	Intermediate Similarity	NPC87069
0.7674	Intermediate Similarity	NPC234337
0.7674	Intermediate Similarity	NPC183339
0.7674	Intermediate Similarity	NPC133389
0.7667	Intermediate Similarity	NPC31786
0.7667	Intermediate Similarity	NPC114594
0.7664	Intermediate Similarity	NPC329913
0.7664	Intermediate Similarity	NPC59459
0.7664	Intermediate Similarity	NPC43627
0.7661	Intermediate Similarity	NPC212415
0.7661	Intermediate Similarity	NPC270699
0.7661	Intermediate Similarity	NPC82899
0.7661	Intermediate Similarity	NPC474314
0.766	Intermediate Similarity	NPC315578
0.766	Intermediate Similarity	NPC99441
0.766	Intermediate Similarity	NPC182869
0.766	Intermediate Similarity	NPC472601
0.766	Intermediate Similarity	NPC472600
0.7655	Intermediate Similarity	NPC5568
0.7655	Intermediate Similarity	NPC471734
0.7647	Intermediate Similarity	NPC304873
0.7643	Intermediate Similarity	NPC126739
0.7643	Intermediate Similarity	NPC197666
0.7643	Intermediate Similarity	NPC61590
0.7642	Intermediate Similarity	NPC251854
0.7642	Intermediate Similarity	NPC174099
0.7642	Intermediate Similarity	NPC196246
0.7642	Intermediate Similarity	NPC214067
0.7642	Intermediate Similarity	NPC93084
0.7639	Intermediate Similarity	NPC473692
0.7639	Intermediate Similarity	NPC474630
0.7638	Intermediate Similarity	NPC131192
0.7634	Intermediate Similarity	NPC475192
0.7634	Intermediate Similarity	NPC65627
0.763	Intermediate Similarity	NPC27712
0.763	Intermediate Similarity	NPC262819
0.7627	Intermediate Similarity	NPC203925
0.7627	Intermediate Similarity	NPC217621
0.7626	Intermediate Similarity	NPC158481
0.7626	Intermediate Similarity	NPC235115
0.7626	Intermediate Similarity	NPC39549
0.7623	Intermediate Similarity	NPC211439
0.7622	Intermediate Similarity	NPC478202
0.7619	Intermediate Similarity	NPC274839
0.7619	Intermediate Similarity	NPC217111
0.7619	Intermediate Similarity	NPC210092
0.7615	Intermediate Similarity	NPC144547
0.7612	Intermediate Similarity	NPC121104
0.7607	Intermediate Similarity	NPC92754
0.7607	Intermediate Similarity	NPC276775
0.7607	Intermediate Similarity	NPC249912
0.7606	Intermediate Similarity	NPC478217
0.7606	Intermediate Similarity	NPC95449
0.7606	Intermediate Similarity	NPC472035
0.7606	Intermediate Similarity	NPC313123
0.7606	Intermediate Similarity	NPC478201
0.7606	Intermediate Similarity	NPC184053
0.7603	Intermediate Similarity	NPC105899
0.76	Intermediate Similarity	NPC478027
0.7594	Intermediate Similarity	NPC236405
0.7594	Intermediate Similarity	NPC9180
0.7594	Intermediate Similarity	NPC100402
0.7591	Intermediate Similarity	NPC476644
0.7589	Intermediate Similarity	NPC471602
0.7589	Intermediate Similarity	NPC268052
0.7589	Intermediate Similarity	NPC476477
0.7589	Intermediate Similarity	NPC92655
0.7589	Intermediate Similarity	NPC216312
0.7589	Intermediate Similarity	NPC299405
0.7589	Intermediate Similarity	NPC295339
0.7589	Intermediate Similarity	NPC473988
0.7589	Intermediate Similarity	NPC111422
0.7589	Intermediate Similarity	NPC29771
0.7589	Intermediate Similarity	NPC306835
0.7589	Intermediate Similarity	NPC256463
0.7586	Intermediate Similarity	NPC471735
0.7586	Intermediate Similarity	NPC473023
0.7583	Intermediate Similarity	NPC255676
0.7583	Intermediate Similarity	NPC60679
0.7583	Intermediate Similarity	NPC89886
0.7581	Intermediate Similarity	NPC1082
0.7581	Intermediate Similarity	NPC305912

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 NPC228739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	813
0.2-0.3	1514
0.3-0.4	2674
0.4-0.5	2369
0.5-0.6	1137
0.6-0.7	383
0.7-0.8	37
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
0.7895	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD9545	Approved
0.7761	Intermediate Similarity	NPD7008	Discontinued
0.7705	Intermediate Similarity	NPD2182	Approved
0.7669	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD164	Approved
0.7661	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5951	Approved
0.7606	Intermediate Similarity	NPD4628	Phase 3
0.7561	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1237	Approved
0.7479	Intermediate Similarity	NPD1238	Approved
0.744	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3764	Approved
0.7295	Intermediate Similarity	NPD1929	Approved
0.7295	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1930	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7236	Approved
0.7219	Intermediate Similarity	NPD7411	Suspended
0.719	Intermediate Similarity	NPD2066	Phase 3
0.7177	Intermediate Similarity	NPD5048	Discontinued
0.7164	Intermediate Similarity	NPD6287	Discontinued
0.7162	Intermediate Similarity	NPD2532	Approved
0.7162	Intermediate Similarity	NPD2534	Approved
0.7162	Intermediate Similarity	NPD2533	Approved
0.7154	Intermediate Similarity	NPD6647	Phase 2
0.7153	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7133	Intermediate Similarity	NPD7239	Suspended
0.7132	Intermediate Similarity	NPD6010	Discontinued
0.7124	Intermediate Similarity	NPD7819	Suspended
0.7107	Intermediate Similarity	NPD9495	Approved
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9256	Approved
0.7094	Intermediate Similarity	NPD9258	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD230	Phase 1
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1607	Approved
0.6986	Remote Similarity	NPD1549	Phase 2
0.6985	Remote Similarity	NPD1608	Approved
0.6972	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9493	Approved
0.6935	Remote Similarity	NPD1932	Approved
0.6929	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1202	Approved
0.6906	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6085	Phase 2
0.6903	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3750	Approved
0.6892	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD7075	Discontinued
0.6863	Remote Similarity	NPD7458	Discontinued
0.6861	Remote Similarity	NPD3972	Approved
0.686	Remote Similarity	NPD688	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1693	Approved
0.6859	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1240	Approved
0.6849	Remote Similarity	NPD1551	Phase 2
0.6839	Remote Similarity	NPD6801	Discontinued
0.6835	Remote Similarity	NPD1470	Approved
0.6832	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3268	Approved
0.6831	Remote Similarity	NPD2313	Discontinued
0.6825	Remote Similarity	NPD5909	Discontinued
0.6821	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6599	Discontinued
0.6818	Remote Similarity	NPD4380	Phase 2
0.6815	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1090	Approved
0.6807	Remote Similarity	NPD1089	Approved
0.6807	Remote Similarity	NPD1086	Approved
0.6803	Remote Similarity	NPD1989	Approved
0.6803	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1201	Approved
0.6788	Remote Similarity	NPD1281	Approved
0.6786	Remote Similarity	NPD8150	Discontinued
0.6781	Remote Similarity	NPD2799	Discontinued
0.6781	Remote Similarity	NPD1510	Phase 2
0.6779	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6273	Approved
0.6767	Remote Similarity	NPD4198	Discontinued
0.6765	Remote Similarity	NPD17	Approved
0.6752	Remote Similarity	NPD9257	Approved
0.6752	Remote Similarity	NPD9259	Approved
0.675	Remote Similarity	NPD6959	Discontinued
0.675	Remote Similarity	NPD1239	Approved
0.6748	Remote Similarity	NPD7177	Discontinued
0.6748	Remote Similarity	NPD7799	Discontinued
0.6744	Remote Similarity	NPD2329	Discontinued
0.6741	Remote Similarity	NPD7741	Discontinued
0.6739	Remote Similarity	NPD6637	Approved
0.6739	Remote Similarity	NPD9717	Approved
0.6735	Remote Similarity	NPD5405	Approved
0.6735	Remote Similarity	NPD5406	Approved
0.6735	Remote Similarity	NPD5408	Approved
0.6735	Remote Similarity	NPD5404	Approved
0.6723	Remote Similarity	NPD800	Approved
0.6713	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7058	Phase 2
0.6709	Remote Similarity	NPD7057	Phase 3
0.6708	Remote Similarity	NPD5710	Approved
0.6708	Remote Similarity	NPD5711	Approved
0.6694	Remote Similarity	NPD1088	Approved
0.6692	Remote Similarity	NPD2067	Discontinued
0.6691	Remote Similarity	NPD5157	Phase 1
0.6691	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5159	Phase 2
0.6689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6002	Phase 3
0.6689	Remote Similarity	NPD6005	Phase 3
0.6689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1471	Phase 3
0.6689	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD4308	Phase 3
0.6645	Remote Similarity	NPD6799	Approved
0.6642	Remote Similarity	NPD4626	Approved
0.6628	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2935	Discontinued
0.6621	Remote Similarity	NPD2979	Phase 3
0.6619	Remote Similarity	NPD4878	Approved
0.6617	Remote Similarity	NPD1241	Discontinued
0.6614	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1565	Approved
0.6613	Remote Similarity	NPD1566	Phase 3
0.6613	Remote Similarity	NPD1564	Approved
0.6607	Remote Similarity	NPD8313	Approved
0.6607	Remote Similarity	NPD8312	Approved
0.6605	Remote Similarity	NPD6232	Discontinued
0.6601	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1243	Approved
0.6597	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3267	Approved
0.6596	Remote Similarity	NPD3266	Approved
0.6596	Remote Similarity	NPD1203	Approved
0.6594	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD9508	Approved
0.6585	Remote Similarity	NPD7473	Discontinued
0.6582	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1651	Approved
0.6569	Remote Similarity	NPD5691	Approved
0.6565	Remote Similarity	NPD1317	Discontinued
0.6562	Remote Similarity	NPD3749	Approved
0.6556	Remote Similarity	NPD8166	Discontinued
0.6555	Remote Similarity	NPD650	Approved
0.6555	Remote Similarity	NPD1087	Approved
0.6547	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2199	Approved
0.6525	Remote Similarity	NPD1876	Approved
0.6525	Remote Similarity	NPD2198	Approved
0.6522	Remote Similarity	NPD1778	Approved
0.6522	Remote Similarity	NPD5305	Approved
0.6522	Remote Similarity	NPD5306	Approved
0.6516	Remote Similarity	NPD5403	Approved
0.6516	Remote Similarity	NPD920	Approved
0.651	Remote Similarity	NPD2438	Suspended
0.651	Remote Similarity	NPD6100	Approved
0.651	Remote Similarity	NPD6099	Approved
0.651	Remote Similarity	NPD2796	Approved
0.65	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7768	Phase 2
0.6496	Remote Similarity	NPD9491	Approved
0.6494	Remote Similarity	NPD5401	Approved
0.6491	Remote Similarity	NPD8434	Phase 2
0.649	Remote Similarity	NPD2800	Approved
0.6488	Remote Similarity	NPD8368	Discontinued
0.6486	Remote Similarity	NPD2567	Approved
0.6486	Remote Similarity	NPD2569	Approved
0.6483	Remote Similarity	NPD411	Approved
0.648	Remote Similarity	NPD3495	Discontinued
0.6479	Remote Similarity	NPD1164	Approved
0.6479	Remote Similarity	NPD2797	Approved
0.6475	Remote Similarity	NPD7609	Phase 3
0.6475	Remote Similarity	NPD4135	Approved
0.6475	Remote Similarity	NPD4106	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