NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.08
Volume:	226.843
LogP:	1.874
LogD:	1.683
LogS:	-3.128
# Rotatable Bonds:	2
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	2.948
Fsp3:	0.154
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:	-4.827
MDCK Permeability:	1.5832072676857933e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	87.18352508544922%
Volume Distribution (VD):	0.553
Pgp-substrate:	17.456050872802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.471
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.778
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	2.211
Half-life (T1/2):	0.454

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.954
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.298
Carcinogencity:	0.426
Eye Corrosion:	0.032
Eye Irritation:	0.952
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC272524

Natural Product ID:	NPC272524
*Common Name:**	(+)-(R)-E-3'-Hydroxyartemidin
IUPAC Name:	3-[(E,3R)-3-hydroxybut-1-enyl]isochromen-1-one
Synonyms:
Standard InCHIKey:	DTXUIAMWHHGGPB-XCODYQFDSA-N
Standard InCHI:	InChI=1S/C13H12O3/c1-9(14)6-7-11-8-10-4-2-3-5-12(10)13(15)16-11/h2-9,14H,1H3/b7-6+/t9-/m1/s1
SMILES:	C[C@H](/C=C/c1cc2ccccc2c(=O)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479324
PubChem CID:	44575579
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*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
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	roots and stolons	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	underground organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21334	Artemisia dracunculus	Species	Asteraceae	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
EC50	1
MIC	2
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	=	100.0	ug	PMID[572040]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	>	200.0	ug.mL-1	PMID[572040]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	292.0	ug ml-1	PMID[572040]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	140.0	ug.mL-1	PMID[572040]

☑ 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 NPC272524 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	278
0.1-0.2	1484
0.2-0.3	3930
0.3-0.4	9397
0.4-0.5	9537
0.5-0.6	5369
0.6-0.7	9249
0.7-0.8	3296
0.8-0.85	129
0.85-0.9	19
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC474685
0.9434	High Similarity	NPC474157
0.9327	High Similarity	NPC209632
0.9231	High Similarity	NPC114594
0.9174	High Similarity	NPC308744
0.9135	High Similarity	NPC60679
0.9065	High Similarity	NPC99846
0.9065	High Similarity	NPC269023
0.8919	High Similarity	NPC210092
0.8899	High Similarity	NPC260818
0.8889	High Similarity	NPC265407
0.8889	High Similarity	NPC83628
0.8879	High Similarity	NPC37622
0.8879	High Similarity	NPC30594
0.8818	High Similarity	NPC158282
0.8818	High Similarity	NPC321852
0.8818	High Similarity	NPC474314
0.875	High Similarity	NPC306740
0.8727	High Similarity	NPC476003
0.8727	High Similarity	NPC210089
0.8716	High Similarity	NPC85493
0.8704	High Similarity	NPC119271
0.8673	High Similarity	NPC149691
0.8661	High Similarity	NPC153053
0.8654	High Similarity	NPC276775
0.8654	High Similarity	NPC92754
0.8654	High Similarity	NPC249912
0.8624	High Similarity	NPC56493
0.8598	High Similarity	NPC89886
0.8585	High Similarity	NPC42211
0.8571	High Similarity	NPC78701
0.8571	High Similarity	NPC35448
0.8571	High Similarity	NPC229242
0.8571	High Similarity	NPC225060
0.8559	High Similarity	NPC223351
0.8559	High Similarity	NPC243355
0.8545	High Similarity	NPC474364
0.8545	High Similarity	NPC10251
0.8545	High Similarity	NPC17417
0.8519	High Similarity	NPC31786
0.8496	Intermediate Similarity	NPC237366
0.8496	Intermediate Similarity	NPC477411
0.8496	Intermediate Similarity	NPC196075
0.8496	Intermediate Similarity	NPC307651
0.8491	Intermediate Similarity	NPC146351
0.8491	Intermediate Similarity	NPC118343
0.8468	Intermediate Similarity	NPC214067
0.8468	Intermediate Similarity	NPC93084
0.8468	Intermediate Similarity	NPC251854
0.8468	Intermediate Similarity	NPC174099
0.8468	Intermediate Similarity	NPC196246
0.8462	Intermediate Similarity	NPC130398
0.8426	Intermediate Similarity	NPC301943
0.8426	Intermediate Similarity	NPC474365
0.8411	Intermediate Similarity	NPC70624
0.8407	Intermediate Similarity	NPC128368
0.8403	Intermediate Similarity	NPC46634
0.8393	Intermediate Similarity	NPC1082
0.8393	Intermediate Similarity	NPC167504
0.8393	Intermediate Similarity	NPC305912
0.8378	Intermediate Similarity	NPC469636
0.8348	Intermediate Similarity	NPC226093
0.8348	Intermediate Similarity	NPC100353
0.8333	Intermediate Similarity	NPC228739
0.8333	Intermediate Similarity	NPC474363
0.8333	Intermediate Similarity	NPC45613
0.8319	Intermediate Similarity	NPC212415
0.8319	Intermediate Similarity	NPC79496
0.8319	Intermediate Similarity	NPC270699
0.8319	Intermediate Similarity	NPC82899
0.8318	Intermediate Similarity	NPC325497
0.8288	Intermediate Similarity	NPC470391
0.8288	Intermediate Similarity	NPC211439
0.8264	Intermediate Similarity	NPC246166
0.8257	Intermediate Similarity	NPC255676
0.8246	Intermediate Similarity	NPC161611
0.8246	Intermediate Similarity	NPC13784
0.8197	Intermediate Similarity	NPC275576
0.8174	Intermediate Similarity	NPC87069
0.8165	Intermediate Similarity	NPC284477
0.8165	Intermediate Similarity	NPC188895
0.8148	Intermediate Similarity	NPC203925
0.813	Intermediate Similarity	NPC169913
0.8115	Intermediate Similarity	NPC91475
0.8115	Intermediate Similarity	NPC295664
0.8115	Intermediate Similarity	NPC265910
0.8108	Intermediate Similarity	NPC269457
0.8103	Intermediate Similarity	NPC228936
0.8091	Intermediate Similarity	NPC82426
0.8091	Intermediate Similarity	NPC160382
0.8091	Intermediate Similarity	NPC91820
0.8073	Intermediate Similarity	NPC282895
0.8067	Intermediate Similarity	NPC204784
0.8053	Intermediate Similarity	NPC281604
0.8036	Intermediate Similarity	NPC475203
0.8036	Intermediate Similarity	NPC474376
0.8036	Intermediate Similarity	NPC472315
0.8036	Intermediate Similarity	NPC472316
0.8036	Intermediate Similarity	NPC136962
0.8034	Intermediate Similarity	NPC135730
0.8033	Intermediate Similarity	NPC471466
0.8018	Intermediate Similarity	NPC280616
0.8018	Intermediate Similarity	NPC171831
0.8018	Intermediate Similarity	NPC249067
0.8018	Intermediate Similarity	NPC242913
0.8	Intermediate Similarity	NPC473243
0.8	Intermediate Similarity	NPC304873
0.8	Intermediate Similarity	NPC25458
0.7983	Intermediate Similarity	NPC27633
0.7983	Intermediate Similarity	NPC94298
0.7983	Intermediate Similarity	NPC94637
0.7982	Intermediate Similarity	NPC217621
0.7981	Intermediate Similarity	NPC173443
0.7969	Intermediate Similarity	NPC136608
0.7969	Intermediate Similarity	NPC38420
0.7963	Intermediate Similarity	NPC253423
0.7951	Intermediate Similarity	NPC217756
0.7949	Intermediate Similarity	NPC81808
0.7949	Intermediate Similarity	NPC474408
0.7946	Intermediate Similarity	NPC105899
0.7934	Intermediate Similarity	NPC50872
0.7931	Intermediate Similarity	NPC474176
0.792	Intermediate Similarity	NPC181715
0.7917	Intermediate Similarity	NPC90522
0.7917	Intermediate Similarity	NPC328459
0.7913	Intermediate Similarity	NPC291799
0.7905	Intermediate Similarity	NPC62765
0.7899	Intermediate Similarity	NPC45104
0.7899	Intermediate Similarity	NPC240664
0.7895	Intermediate Similarity	NPC318327
0.789	Intermediate Similarity	NPC175852
0.789	Intermediate Similarity	NPC160548
0.789	Intermediate Similarity	NPC210529
0.7885	Intermediate Similarity	NPC304760
0.7876	Intermediate Similarity	NPC37115
0.7876	Intermediate Similarity	NPC477251
0.7851	Intermediate Similarity	NPC233282
0.7851	Intermediate Similarity	NPC72977
0.785	Intermediate Similarity	NPC23453
0.7845	Intermediate Similarity	NPC66208
0.784	Intermediate Similarity	NPC110211
0.784	Intermediate Similarity	NPC470753
0.784	Intermediate Similarity	NPC473220
0.7826	Intermediate Similarity	NPC273837
0.7818	Intermediate Similarity	NPC472318
0.7818	Intermediate Similarity	NPC98911
0.7815	Intermediate Similarity	NPC128825
0.7815	Intermediate Similarity	NPC131192
0.7812	Intermediate Similarity	NPC470831
0.7812	Intermediate Similarity	NPC214702
0.7807	Intermediate Similarity	NPC20485
0.7807	Intermediate Similarity	NPC156648
0.7807	Intermediate Similarity	NPC277788
0.7805	Intermediate Similarity	NPC69403
0.7805	Intermediate Similarity	NPC291189
0.7805	Intermediate Similarity	NPC65627
0.7798	Intermediate Similarity	NPC270654
0.7797	Intermediate Similarity	NPC186933
0.7797	Intermediate Similarity	NPC474095
0.7797	Intermediate Similarity	NPC470764
0.7795	Intermediate Similarity	NPC82712
0.7788	Intermediate Similarity	NPC96625
0.7788	Intermediate Similarity	NPC89377
0.7787	Intermediate Similarity	NPC144547
0.7778	Intermediate Similarity	NPC470841
0.7769	Intermediate Similarity	NPC474097
0.7769	Intermediate Similarity	NPC61779
0.7768	Intermediate Similarity	NPC234305
0.776	Intermediate Similarity	NPC4164
0.776	Intermediate Similarity	NPC49938
0.776	Intermediate Similarity	NPC470765
0.776	Intermediate Similarity	NPC236405
0.7757	Intermediate Similarity	NPC77273
0.7752	Intermediate Similarity	NPC470160
0.775	Intermediate Similarity	NPC217423
0.7748	Intermediate Similarity	NPC112552
0.7739	Intermediate Similarity	NPC40178
0.7734	Intermediate Similarity	NPC72915
0.7731	Intermediate Similarity	NPC471616
0.7727	Intermediate Similarity	NPC475195
0.7717	Intermediate Similarity	NPC2596
0.7712	Intermediate Similarity	NPC196673
0.771	Intermediate Similarity	NPC142027
0.7706	Intermediate Similarity	NPC61944
0.7705	Intermediate Similarity	NPC289432
0.7705	Intermediate Similarity	NPC988
0.7699	Intermediate Similarity	NPC85977
0.7698	Intermediate Similarity	NPC472706
0.7698	Intermediate Similarity	NPC204579
0.7692	Intermediate Similarity	NPC43627
0.7692	Intermediate Similarity	NPC318107
0.7685	Intermediate Similarity	NPC261181
0.768	Intermediate Similarity	NPC221798
0.768	Intermediate Similarity	NPC184219
0.7674	Intermediate Similarity	NPC7012
0.7672	Intermediate Similarity	NPC234639
0.7667	Intermediate Similarity	NPC128249
0.7667	Intermediate Similarity	NPC190298
0.7664	Intermediate Similarity	NPC119631
0.7661	Intermediate Similarity	NPC472703

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 NPC272524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	957
0.2-0.3	1353
0.3-0.4	2493
0.4-0.5	2173
0.5-0.6	1315
0.6-0.7	483
0.7-0.8	122
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD2181	Clinical (unspecified phase)
0.8545	High Similarity	NPD2182	Approved
0.8519	High Similarity	NPD164	Approved
0.8491	Intermediate Similarity	NPD1238	Approved
0.8319	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD1237	Approved
0.8018	Intermediate Similarity	NPD5909	Discontinued
0.7983	Intermediate Similarity	NPD9545	Approved
0.7905	Intermediate Similarity	NPD9256	Approved
0.7905	Intermediate Similarity	NPD9258	Approved
0.789	Intermediate Similarity	NPD9495	Approved
0.7815	Intermediate Similarity	NPD9493	Approved
0.7795	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD7008	Discontinued
0.7739	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9259	Approved
0.7692	Intermediate Similarity	NPD9257	Approved
0.7685	Intermediate Similarity	NPD1202	Approved
0.7647	Intermediate Similarity	NPD5951	Approved
0.7619	Intermediate Similarity	NPD1282	Approved
0.7611	Intermediate Similarity	NPD6647	Phase 2
0.7563	Intermediate Similarity	NPD1241	Discontinued
0.7561	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2067	Discontinued
0.752	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD2629	Approved
0.7462	Intermediate Similarity	NPD3764	Approved
0.7456	Intermediate Similarity	NPD1930	Approved
0.7456	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1929	Approved
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7345	Intermediate Similarity	NPD2066	Phase 3
0.7344	Intermediate Similarity	NPD2797	Approved
0.7344	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7302	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6287	Discontinued
0.7302	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2798	Approved
0.728	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2198	Approved
0.7266	Intermediate Similarity	NPD2199	Approved
0.7266	Intermediate Similarity	NPD1283	Approved
0.7266	Intermediate Similarity	NPD1876	Approved
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.7239	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD9491	Approved
0.7236	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6273	Approved
0.7232	Intermediate Similarity	NPD1989	Approved
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9267	Approved
0.7203	Intermediate Similarity	NPD9263	Approved
0.7203	Intermediate Similarity	NPD9264	Approved
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7167	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1281	Approved
0.7154	Intermediate Similarity	NPD1019	Discontinued
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7153	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9260	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7132	Intermediate Similarity	NPD4308	Phase 3
0.7122	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3750	Approved
0.7122	Intermediate Similarity	NPD7003	Approved
0.7119	Intermediate Similarity	NPD3134	Approved
0.7109	Intermediate Similarity	NPD1608	Approved
0.7109	Intermediate Similarity	NPD3972	Approved
0.7097	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1089	Approved
0.7091	Intermediate Similarity	NPD1086	Approved
0.7091	Intermediate Similarity	NPD1090	Approved
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1932	Approved
0.7068	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD1358	Approved
0.7054	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5277	Phase 2
0.7034	Intermediate Similarity	NPD9697	Approved
0.7029	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1239	Approved
0.7021	Intermediate Similarity	NPD7236	Approved
0.7019	Intermediate Similarity	NPD9490	Approved
0.7009	Intermediate Similarity	NPD9261	Approved
0.7008	Intermediate Similarity	NPD17	Approved
0.7008	Intermediate Similarity	NPD5306	Approved
0.7008	Intermediate Similarity	NPD4626	Approved
0.7008	Intermediate Similarity	NPD5305	Approved
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD800	Approved
0.6991	Remote Similarity	NPD1693	Approved
0.6977	Remote Similarity	NPD1481	Phase 2
0.6972	Remote Similarity	NPD650	Approved
0.6972	Remote Similarity	NPD1087	Approved
0.6967	Remote Similarity	NPD9508	Approved
0.6967	Remote Similarity	NPD969	Suspended
0.6966	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1088	Approved
0.6963	Remote Similarity	NPD4307	Phase 2
0.6957	Remote Similarity	NPD2935	Discontinued
0.6957	Remote Similarity	NPD1551	Phase 2
0.6953	Remote Similarity	NPD4106	Approved
0.6953	Remote Similarity	NPD4136	Approved
0.6953	Remote Similarity	NPD4135	Approved
0.6947	Remote Similarity	NPD3267	Approved
0.6947	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD5403	Approved
0.694	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD3673	Approved
0.6937	Remote Similarity	NPD3672	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD5159	Phase 2
0.6923	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5157	Phase 1
0.6916	Remote Similarity	NPD3971	Phase 1
0.6912	Remote Similarity	NPD447	Suspended
0.6912	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD1535	Discovery
0.6899	Remote Similarity	NPD4807	Approved
0.6899	Remote Similarity	NPD4806	Approved
0.6894	Remote Similarity	NPD5647	Approved
0.6894	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6085	Phase 2
0.6891	Remote Similarity	NPD5048	Discontinued
0.6887	Remote Similarity	NPD226	Approved
0.688	Remote Similarity	NPD4198	Discontinued
0.687	Remote Similarity	NPD1566	Phase 3
0.687	Remote Similarity	NPD1565	Approved
0.687	Remote Similarity	NPD5667	Approved
0.687	Remote Similarity	NPD1564	Approved
0.6864	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2329	Discontinued
0.6855	Remote Similarity	NPD6010	Discontinued
0.6847	Remote Similarity	NPD689	Discontinued
0.6846	Remote Similarity	NPD4878	Approved
0.6846	Remote Similarity	NPD1877	Discontinued
0.6846	Remote Similarity	NPD6637	Approved
0.6842	Remote Similarity	NPD9494	Approved
0.6838	Remote Similarity	NPD1240	Approved
0.6838	Remote Similarity	NPD2979	Phase 3
0.6835	Remote Similarity	NPD4477	Approved
0.6835	Remote Similarity	NPD4476	Approved
0.6822	Remote Similarity	NPD3496	Discontinued
0.6818	Remote Similarity	NPD2625	Approved
0.6818	Remote Similarity	NPD1164	Approved
0.6818	Remote Similarity	NPD9567	Approved
0.6818	Remote Similarity	NPD2628	Approved
0.6818	Remote Similarity	NPD2160	Approved
0.6818	Remote Similarity	NPD2159	Approved
0.6818	Remote Similarity	NPD552	Approved
0.6818	Remote Similarity	NPD553	Approved
0.6818	Remote Similarity	NPD2627	Approved
0.6818	Remote Similarity	NPD2626	Approved
0.6815	Remote Similarity	NPD6798	Discontinued
0.6812	Remote Similarity	NPD2567	Approved
0.6812	Remote Similarity	NPD2569	Approved
0.68	Remote Similarity	NPD9281	Approved
0.6797	Remote Similarity	NPD1651	Approved
0.6797	Remote Similarity	NPD4105	Approved
0.6797	Remote Similarity	NPD5585	Approved
0.6797	Remote Similarity	NPD4102	Approved
0.6788	Remote Similarity	NPD1933	Approved
0.6788	Remote Similarity	NPD6355	Discontinued
0.6783	Remote Similarity	NPD7440	Discontinued
0.6781	Remote Similarity	NPD7239	Suspended
0.6772	Remote Similarity	NPD2347	Approved
0.6769	Remote Similarity	NPD1201	Approved
0.6769	Remote Similarity	NPD422	Phase 1
0.6765	Remote Similarity	NPD6663	Approved
0.6765	Remote Similarity	NPD6233	Phase 2
0.6765	Remote Similarity	NPD4062	Phase 3
0.6765	Remote Similarity	NPD520	Approved
0.6765	Remote Similarity	NPD7713	Phase 3
0.6763	Remote Similarity	NPD7033	Discontinued
0.6763	Remote Similarity	NPD1510	Phase 2
0.6762	Remote Similarity	NPD227	Approved
0.6762	Remote Similarity	NPD225	Approved
0.6754	Remote Similarity	NPD1563	Approved
0.6744	Remote Similarity	NPD1778	Approved
0.6742	Remote Similarity	NPD3225	Approved
0.6741	Remote Similarity	NPD6039	Approved
0.6739	Remote Similarity	NPD1607	Approved
0.6738	Remote Similarity	NPD1549	Phase 2
0.6736	Remote Similarity	NPD6799	Approved
0.6735	Remote Similarity	NPD2651	Approved
0.6735	Remote Similarity	NPD2649	Approved
0.6735	Remote Similarity	NPD3226	Approved
0.6726	Remote Similarity	NPD7609	Phase 3
0.6716	Remote Similarity	NPD5204	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