NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.07
Volume:	215.417
LogP:	2.631
LogD:	3.092
LogS:	-4.084
# Rotatable Bonds:	1
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	2.598
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.621
MDCK Permeability:	1.7291969925281592e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.515

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	82.51704406738281%
Volume Distribution (VD):	2.166
Pgp-substrate:	4.499172687530518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.222
CYP2D6-substrate:	0.818
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	4.053
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.472
Skin Sensitization:	0.746
Carcinogencity:	0.844
Eye Corrosion:	0.214
Eye Irritation:	0.957
Respiratory Toxicity:	0.158

Download Data

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

Natural Product: NPC269023

Natural Product ID:	NPC269023
*Common Name:**	Capillarin
IUPAC Name:	3-but-2-ynylisochromen-1-one
Synonyms:	Capillarin
Standard InCHIKey:	KUJLPCYCQICVRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O2/c1-2-3-7-11-9-10-6-4-5-8-12(10)13(14)15-11/h4-6,8-9H,7H2,1H3
SMILES:	CC#CCc1cc2ccccc2c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479330
PubChem CID:	3083811
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	underground organs	n.a.	n.a.	PMID[14738379]
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]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
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	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	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]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31579	Artemisia capillaries	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1
Others	1
Potency	5

Activity Type	# Activity
Individual Protein	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	3981.1	nM	PMID[533261]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[533261]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[533261]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	100.0	ug.mL-1	PMID[533260]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	92.0	ug ml-1	PMID[533260]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	37.0	ug.mL-1	PMID[533260]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[533261]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[533261]

☑ 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 NPC269023 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	425
0.1-0.2	2153
0.2-0.3	5078
0.3-0.4	12004
0.4-0.5	6234
0.5-0.6	7461
0.6-0.7	7854
0.7-0.8	1409
0.8-0.85	56
0.85-0.9	12
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99846
0.97	High Similarity	NPC209632
0.96	High Similarity	NPC114594
0.9434	High Similarity	NPC210092
0.9434	High Similarity	NPC474685
0.9238	High Similarity	NPC243355
0.9238	High Similarity	NPC474157
0.9223	High Similarity	NPC30594
0.9223	High Similarity	NPC37622
0.9118	High Similarity	NPC60679
0.9065	High Similarity	NPC272524
0.8981	High Similarity	NPC308744
0.8704	High Similarity	NPC210089
0.8692	High Similarity	NPC265407
0.8692	High Similarity	NPC83628
0.8679	High Similarity	NPC119271
0.8667	High Similarity	NPC31786
0.8654	High Similarity	NPC45613
0.8649	High Similarity	NPC100353
0.8641	High Similarity	NPC325497
0.8627	High Similarity	NPC92754
0.8627	High Similarity	NPC249912
0.8627	High Similarity	NPC276775
0.8624	High Similarity	NPC212415
0.8614	High Similarity	NPC130398
0.8598	High Similarity	NPC56493
0.8571	High Similarity	NPC89886
0.8558	High Similarity	NPC42211
0.8544	High Similarity	NPC225060
0.8544	High Similarity	NPC78701
0.8544	High Similarity	NPC35448
0.8519	High Similarity	NPC17417
0.8519	High Similarity	NPC10251
0.8482	Intermediate Similarity	NPC149691
0.8468	Intermediate Similarity	NPC196075
0.8462	Intermediate Similarity	NPC118343
0.8462	Intermediate Similarity	NPC146351
0.844	Intermediate Similarity	NPC196246
0.844	Intermediate Similarity	NPC174099
0.844	Intermediate Similarity	NPC214067
0.844	Intermediate Similarity	NPC251854
0.844	Intermediate Similarity	NPC93084
0.8396	Intermediate Similarity	NPC301943
0.8396	Intermediate Similarity	NPC474365
0.8381	Intermediate Similarity	NPC70624
0.8365	Intermediate Similarity	NPC229242
0.8364	Intermediate Similarity	NPC167504
0.8364	Intermediate Similarity	NPC476003
0.8364	Intermediate Similarity	NPC305912
0.8364	Intermediate Similarity	NPC260818
0.8364	Intermediate Similarity	NPC1082
0.8349	Intermediate Similarity	NPC474364
0.8349	Intermediate Similarity	NPC85493
0.8304	Intermediate Similarity	NPC477411
0.8304	Intermediate Similarity	NPC307651
0.8288	Intermediate Similarity	NPC82899
0.8288	Intermediate Similarity	NPC321852
0.8288	Intermediate Similarity	NPC79496
0.8288	Intermediate Similarity	NPC270699
0.8286	Intermediate Similarity	NPC203925
0.8257	Intermediate Similarity	NPC470391
0.822	Intermediate Similarity	NPC46634
0.8214	Intermediate Similarity	NPC128368
0.8214	Intermediate Similarity	NPC13784
0.8198	Intermediate Similarity	NPC291799
0.8182	Intermediate Similarity	NPC469636
0.8182	Intermediate Similarity	NPC181715
0.8158	Intermediate Similarity	NPC226093
0.8142	Intermediate Similarity	NPC153053
0.8131	Intermediate Similarity	NPC188895
0.8073	Intermediate Similarity	NPC269457
0.807	Intermediate Similarity	NPC228936
0.807	Intermediate Similarity	NPC306740
0.8056	Intermediate Similarity	NPC255676
0.8053	Intermediate Similarity	NPC161611
0.8	Intermediate Similarity	NPC318107
0.8	Intermediate Similarity	NPC135730
0.7981	Intermediate Similarity	NPC261181
0.7965	Intermediate Similarity	NPC158282
0.7965	Intermediate Similarity	NPC474314
0.7963	Intermediate Similarity	NPC284477
0.7946	Intermediate Similarity	NPC273837
0.7941	Intermediate Similarity	NPC173443
0.7934	Intermediate Similarity	NPC91475
0.7934	Intermediate Similarity	NPC265910
0.7921	Intermediate Similarity	NPC96625
0.7913	Intermediate Similarity	NPC474408
0.787	Intermediate Similarity	NPC282895
0.787	Intermediate Similarity	NPC112552
0.7863	Intermediate Similarity	NPC228318
0.7863	Intermediate Similarity	NPC45104
0.7826	Intermediate Similarity	NPC237366
0.7818	Intermediate Similarity	NPC269644
0.7815	Intermediate Similarity	NPC473243
0.7815	Intermediate Similarity	NPC232958
0.7805	Intermediate Similarity	NPC51292
0.7798	Intermediate Similarity	NPC304873
0.7798	Intermediate Similarity	NPC25458
0.7787	Intermediate Similarity	NPC246166
0.7787	Intermediate Similarity	NPC295664
0.7787	Intermediate Similarity	NPC107846
0.7778	Intermediate Similarity	NPC217621
0.7778	Intermediate Similarity	NPC470860
0.7769	Intermediate Similarity	NPC223351
0.7759	Intermediate Similarity	NPC474095
0.7757	Intermediate Similarity	NPC253423
0.7757	Intermediate Similarity	NPC270654
0.775	Intermediate Similarity	NPC50872
0.775	Intermediate Similarity	NPC144547
0.7748	Intermediate Similarity	NPC105899
0.7745	Intermediate Similarity	NPC89377
0.7739	Intermediate Similarity	NPC474176
0.7736	Intermediate Similarity	NPC5472
0.7731	Intermediate Similarity	NPC204784
0.7724	Intermediate Similarity	NPC121272
0.7712	Intermediate Similarity	NPC217423
0.7699	Intermediate Similarity	NPC318327
0.7699	Intermediate Similarity	NPC192577
0.7699	Intermediate Similarity	NPC281604
0.7692	Intermediate Similarity	NPC62765
0.7692	Intermediate Similarity	NPC188907
0.7692	Intermediate Similarity	NPC220540
0.7679	Intermediate Similarity	NPC1065
0.7672	Intermediate Similarity	NPC474363
0.767	Intermediate Similarity	NPC304760
0.7667	Intermediate Similarity	NPC988
0.7667	Intermediate Similarity	NPC289432
0.7652	Intermediate Similarity	NPC66208
0.7652	Intermediate Similarity	NPC23332
0.7642	Intermediate Similarity	NPC23453
0.7619	Intermediate Similarity	NPC119631
0.7615	Intermediate Similarity	NPC472318
0.7615	Intermediate Similarity	NPC98911
0.7611	Intermediate Similarity	NPC156648
0.7607	Intermediate Similarity	NPC81808
0.7607	Intermediate Similarity	NPC470764
0.7607	Intermediate Similarity	NPC186933
0.7596	Intermediate Similarity	NPC220893
0.7568	Intermediate Similarity	NPC234305
0.7565	Intermediate Similarity	NPC183648
0.7565	Intermediate Similarity	NPC137315
0.7563	Intermediate Similarity	NPC240664
0.7561	Intermediate Similarity	NPC228739
0.7549	Intermediate Similarity	NPC58616
0.7549	Intermediate Similarity	NPC294134
0.7547	Intermediate Similarity	NPC77273
0.7544	Intermediate Similarity	NPC40178
0.7525	Intermediate Similarity	NPC288903
0.7521	Intermediate Similarity	NPC470092
0.7521	Intermediate Similarity	NPC279916
0.7521	Intermediate Similarity	NPC230951
0.7521	Intermediate Similarity	NPC238861
0.7521	Intermediate Similarity	NPC77000
0.75	Intermediate Similarity	NPC94298
0.75	Intermediate Similarity	NPC27633
0.75	Intermediate Similarity	NPC470163
0.75	Intermediate Similarity	NPC85977
0.75	Intermediate Similarity	NPC32298
0.75	Intermediate Similarity	NPC71795
0.75	Intermediate Similarity	NPC61944
0.75	Intermediate Similarity	NPC470162
0.75	Intermediate Similarity	NPC94637
0.748	Intermediate Similarity	NPC471832
0.7479	Intermediate Similarity	NPC131192
0.7479	Intermediate Similarity	NPC128825
0.7479	Intermediate Similarity	NPC190298
0.7478	Intermediate Similarity	NPC234639
0.7478	Intermediate Similarity	NPC259554
0.7477	Intermediate Similarity	NPC244427
0.7477	Intermediate Similarity	NPC222390
0.746	Intermediate Similarity	NPC37512
0.7456	Intermediate Similarity	NPC47536
0.7456	Intermediate Similarity	NPC211439
0.7456	Intermediate Similarity	NPC203732
0.7456	Intermediate Similarity	NPC249811
0.7453	Intermediate Similarity	NPC110704
0.744	Intermediate Similarity	NPC275576
0.744	Intermediate Similarity	NPC470765
0.744	Intermediate Similarity	NPC476599
0.744	Intermediate Similarity	NPC165556
0.7438	Intermediate Similarity	NPC328459
0.7438	Intermediate Similarity	NPC90522
0.7438	Intermediate Similarity	NPC61779
0.7438	Intermediate Similarity	NPC54243
0.7436	Intermediate Similarity	NPC17693
0.7431	Intermediate Similarity	NPC156021
0.7426	Intermediate Similarity	NPC99240
0.7422	Intermediate Similarity	NPC475478
0.7422	Intermediate Similarity	NPC473271
0.7419	Intermediate Similarity	NPC182646
0.7417	Intermediate Similarity	NPC469574
0.7417	Intermediate Similarity	NPC469954
0.7414	Intermediate Similarity	NPC474057
0.7411	Intermediate Similarity	NPC274443
0.7411	Intermediate Similarity	NPC329556
0.7404	Intermediate Similarity	NPC286608
0.7404	Intermediate Similarity	NPC169050
0.7387	Intermediate Similarity	NPC473325
0.7381	Intermediate Similarity	NPC470753
0.7381	Intermediate Similarity	NPC473220

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 NPC269023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	990
0.2-0.3	1326
0.3-0.4	2828
0.4-0.5	2077
0.5-0.6	1105
0.6-0.7	336
0.7-0.8	70
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD164	Approved
0.8624	High Similarity	NPD1609	Clinical (unspecified phase)
0.8532	High Similarity	NPD2181	Clinical (unspecified phase)
0.8519	High Similarity	NPD2182	Approved
0.8462	Intermediate Similarity	NPD1238	Approved
0.8	Intermediate Similarity	NPD9259	Approved
0.8	Intermediate Similarity	NPD9257	Approved
0.7981	Intermediate Similarity	NPD1202	Approved
0.7913	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5909	Discontinued
0.7692	Intermediate Similarity	NPD9258	Approved
0.7692	Intermediate Similarity	NPD9256	Approved
0.7544	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1241	Discontinued
0.7521	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.7479	Intermediate Similarity	NPD9493	Approved
0.7458	Intermediate Similarity	NPD5951	Approved
0.7411	Intermediate Similarity	NPD1929	Approved
0.7411	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1930	Approved
0.7407	Intermediate Similarity	NPD9260	Approved
0.7404	Intermediate Similarity	NPD1282	Approved
0.7398	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6287	Discontinued
0.736	Intermediate Similarity	NPD1876	Approved
0.7344	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9717	Approved
0.7328	Intermediate Similarity	NPD2067	Discontinued
0.73	Intermediate Similarity	NPD9490	Approved
0.7297	Intermediate Similarity	NPD2066	Phase 3
0.7287	Intermediate Similarity	NPD3764	Approved
0.7281	Intermediate Similarity	NPD9697	Approved
0.7266	Intermediate Similarity	NPD6832	Phase 2
0.7258	Intermediate Similarity	NPD1281	Approved
0.7257	Intermediate Similarity	NPD9261	Approved
0.7244	Intermediate Similarity	NPD2798	Approved
0.7238	Intermediate Similarity	NPD1087	Approved
0.7238	Intermediate Similarity	NPD650	Approved
0.7236	Intermediate Similarity	NPD17	Approved
0.7218	Intermediate Similarity	NPD3748	Approved
0.7209	Intermediate Similarity	NPD7008	Discontinued
0.72	Intermediate Similarity	NPD3972	Approved
0.7193	Intermediate Similarity	NPD1237	Approved
0.7184	Intermediate Similarity	NPD9491	Approved
0.7182	Intermediate Similarity	NPD1989	Approved
0.7176	Intermediate Similarity	NPD4307	Phase 2
0.7165	Intermediate Similarity	NPD1203	Approved
0.7165	Intermediate Similarity	NPD3266	Approved
0.7165	Intermediate Similarity	NPD3267	Approved
0.7165	Intermediate Similarity	NPD2797	Approved
0.7154	Intermediate Similarity	NPD2313	Discontinued
0.712	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2346	Discontinued
0.7109	Intermediate Similarity	NPD1019	Discontinued
0.7091	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2199	Approved
0.7087	Intermediate Similarity	NPD2198	Approved
0.7087	Intermediate Similarity	NPD1283	Approved
0.7069	Intermediate Similarity	NPD3134	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7054	Intermediate Similarity	NPD9495	Approved
0.7037	Intermediate Similarity	NPD1086	Approved
0.7037	Intermediate Similarity	NPD1089	Approved
0.7037	Intermediate Similarity	NPD1090	Approved
0.703	Intermediate Similarity	NPD227	Approved
0.703	Intermediate Similarity	NPD225	Approved
0.7018	Intermediate Similarity	NPD1932	Approved
0.7009	Intermediate Similarity	NPD9267	Approved
0.7009	Intermediate Similarity	NPD9263	Approved
0.7009	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1358	Approved
0.7009	Intermediate Similarity	NPD9264	Approved
0.7	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1563	Approved
0.6977	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1239	Approved
0.6972	Remote Similarity	NPD7609	Phase 3
0.6963	Remote Similarity	NPD4308	Phase 3
0.6963	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD3750	Approved
0.6949	Remote Similarity	NPD74	Approved
0.6949	Remote Similarity	NPD9266	Approved
0.6944	Remote Similarity	NPD800	Approved
0.6937	Remote Similarity	NPD1693	Approved
0.6935	Remote Similarity	NPD1894	Discontinued
0.6934	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7631	Approved
0.6909	Remote Similarity	NPD1088	Approved
0.6894	Remote Similarity	NPD3268	Approved
0.6891	Remote Similarity	NPD5236	Approved
0.6891	Remote Similarity	NPD5237	Approved
0.6891	Remote Similarity	NPD5235	Approved
0.6891	Remote Similarity	NPD5239	Approved
0.6891	Remote Similarity	NPD5240	Approved
0.6881	Remote Similarity	NPD3673	Approved
0.6881	Remote Similarity	NPD3672	Approved
0.688	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD1651	Approved
0.688	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1933	Approved
0.6861	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5277	Phase 2
0.6835	Remote Similarity	NPD7003	Approved
0.6833	Remote Similarity	NPD2201	Approved
0.6827	Remote Similarity	NPD942	Approved
0.6827	Remote Similarity	NPD226	Approved
0.6825	Remote Similarity	NPD5305	Approved
0.6825	Remote Similarity	NPD5306	Approved
0.6814	Remote Similarity	NPD1566	Phase 3
0.6814	Remote Similarity	NPD1565	Approved
0.6814	Remote Similarity	NPD1564	Approved
0.681	Remote Similarity	NPD6647	Phase 2
0.6807	Remote Similarity	NPD2329	Discontinued
0.6797	Remote Similarity	NPD1481	Phase 2
0.6797	Remote Similarity	NPD6637	Approved
0.6791	Remote Similarity	NPD2979	Phase 3
0.6777	Remote Similarity	NPD9508	Approved
0.6769	Remote Similarity	NPD553	Approved
0.6769	Remote Similarity	NPD552	Approved
0.6769	Remote Similarity	NPD9567	Approved
0.6767	Remote Similarity	NPD411	Approved
0.6757	Remote Similarity	NPD1508	Approved
0.6748	Remote Similarity	NPD2629	Approved
0.6746	Remote Similarity	NPD5585	Approved
0.6744	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD447	Suspended
0.6739	Remote Similarity	NPD2353	Approved
0.6739	Remote Similarity	NPD1471	Phase 3
0.6739	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5535	Approved
0.672	Remote Similarity	NPD2347	Approved
0.6719	Remote Similarity	NPD1535	Discovery
0.6716	Remote Similarity	NPD8032	Phase 2
0.6714	Remote Similarity	NPD4628	Phase 3
0.6713	Remote Similarity	NPD6273	Approved
0.6698	Remote Similarity	NPD3971	Phase 1
0.6693	Remote Similarity	NPD4626	Approved
0.6692	Remote Similarity	NPD5667	Approved
0.6692	Remote Similarity	NPD6966	Discovery
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD3495	Discontinued
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD3373	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6643	Remote Similarity	NPD1243	Approved
0.6643	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2567	Approved
0.6642	Remote Similarity	NPD2569	Approved
0.6642	Remote Similarity	NPD1296	Phase 2
0.6641	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1164	Approved
0.6619	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD7611	Approved
0.6614	Remote Similarity	NPD4105	Approved
0.6614	Remote Similarity	NPD4102	Approved
0.6613	Remote Similarity	NPD9281	Approved
0.6609	Remote Similarity	NPD5926	Approved
0.6596	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7713	Phase 3
0.6591	Remote Similarity	NPD2788	Approved
0.6589	Remote Similarity	NPD1611	Approved
0.6589	Remote Similarity	NPD422	Phase 1
0.6589	Remote Similarity	NPD1201	Approved
0.6579	Remote Similarity	NPD1843	Approved
0.6575	Remote Similarity	NPD3226	Approved
0.6569	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6039	Approved
0.6565	Remote Similarity	NPD3225	Approved
0.656	Remote Similarity	NPD4198	Discontinued
0.6557	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2354	Approved
0.6549	Remote Similarity	NPD3887	Approved
0.6547	Remote Similarity	NPD2796	Approved
0.6547	Remote Similarity	NPD1551	Phase 2
0.6547	Remote Similarity	NPD2531	Phase 2
0.6547	Remote Similarity	NPD4476	Approved
0.6547	Remote Similarity	NPD2438	Suspended
0.6547	Remote Similarity	NPD4477	Approved
0.6544	Remote Similarity	NPD1240	Approved
0.6538	Remote Similarity	NPD1877	Discontinued
0.6515	Remote Similarity	NPD1470	Approved
0.6512	Remote Similarity	NPD4106	Approved
0.6512	Remote Similarity	NPD4136	Approved
0.6512	Remote Similarity	NPD3847	Discontinued
0.6512	Remote Similarity	NPD4135	Approved
0.6508	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD969	Suspended
0.6503	Remote Similarity	NPD7236	Approved
0.65	Remote Similarity	NPD2344	Approved
0.6496	Remote Similarity	NPD230	Phase 1
0.6496	Remote Similarity	NPD4622	Approved
0.6496	Remote Similarity	NPD4618	Approved
0.6489	Remote Similarity	NPD4359	Approved
0.6486	Remote Similarity	NPD5347	Phase 2
0.6486	Remote Similarity	NPD5346	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data