NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.33
Volume:	477.08
LogP:	4.814
LogD:	5.002
LogS:	-5.224
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	5.054
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.764
MDCK Permeability:	2.5417915821890347e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.83
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.606
Plasma Protein Binding (PPB):	91.55142974853516%
Volume Distribution (VD):	0.554
Pgp-substrate:	2.877457618713379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.165
CYP1A2-substrate:	0.293
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.414
CYP3A4-inhibitor:	0.808
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	11.32
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.688
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.311
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.688
Carcinogencity:	0.051
Eye Corrosion:	0.037
Eye Irritation:	0.051
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC209632

Natural Product ID:	NPC209632
*Common Name:**	(E/Z)-Artemidin
IUPAC Name:	3-[(E)-but-1-enyl]isochromen-1-one
Synonyms:	(E/Z)-Artemidin
Standard InCHIKey:	DHKBMMCQVXFEJY-XVNBXDOJSA-N
Standard InCHI:	InChI=1S/C13H12O2/c1-2-3-7-11-9-10-6-4-5-8-12(10)13(14)15-11/h3-9H,2H2,1H3/b7-3+
SMILES:	CC/C=C/c1cc2ccccc2c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477123
PubChem CID:	5945155
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[470989]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	25.0	ug.mL-1	PMID[470989]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	19.0	ug ml-1	PMID[470989]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	11.0	ug.mL-1	PMID[470989]

☑ 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 NPC209632 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	398
0.1-0.2	2162
0.2-0.3	5057
0.3-0.4	11730
0.4-0.5	6299
0.5-0.6	7115
0.6-0.7	8056
0.7-0.8	1752
0.8-0.85	94
0.85-0.9	15
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC114594
0.97	High Similarity	NPC269023
0.97	High Similarity	NPC99846
0.951	High Similarity	NPC474157
0.95	High Similarity	NPC37622
0.95	High Similarity	NPC30594
0.9394	High Similarity	NPC60679
0.9327	High Similarity	NPC272524
0.9238	High Similarity	NPC308744
0.9151	High Similarity	NPC474685
0.9151	High Similarity	NPC210092
0.9135	High Similarity	NPC243355
0.8952	High Similarity	NPC210089
0.8942	High Similarity	NPC265407
0.8942	High Similarity	NPC83628
0.8932	High Similarity	NPC119271
0.8922	High Similarity	NPC31786
0.8911	High Similarity	NPC45613
0.89	High Similarity	NPC325497
0.8889	High Similarity	NPC92754
0.8889	High Similarity	NPC249912
0.8889	High Similarity	NPC276775
0.8878	High Similarity	NPC130398
0.8868	High Similarity	NPC212415
0.8846	High Similarity	NPC56493
0.8824	High Similarity	NPC89886
0.8812	High Similarity	NPC42211
0.88	High Similarity	NPC225060
0.88	High Similarity	NPC35448
0.88	High Similarity	NPC78701
0.8762	High Similarity	NPC10251
0.8762	High Similarity	NPC17417
0.8716	High Similarity	NPC149691
0.8713	High Similarity	NPC146351
0.8713	High Similarity	NPC118343
0.8704	High Similarity	NPC196075
0.8679	High Similarity	NPC196246
0.8679	High Similarity	NPC93084
0.8679	High Similarity	NPC174099
0.8679	High Similarity	NPC214067
0.8679	High Similarity	NPC251854
0.8641	High Similarity	NPC474365
0.8641	High Similarity	NPC301943
0.8627	High Similarity	NPC70624
0.8614	High Similarity	NPC229242
0.8598	High Similarity	NPC260818
0.8598	High Similarity	NPC167504
0.8598	High Similarity	NPC305912
0.8598	High Similarity	NPC1082
0.8585	High Similarity	NPC474364
0.8585	High Similarity	NPC85493
0.8532	High Similarity	NPC477411
0.8532	High Similarity	NPC307651
0.8529	High Similarity	NPC203925
0.8519	High Similarity	NPC79496
0.8519	High Similarity	NPC270699
0.8519	High Similarity	NPC82899
0.8519	High Similarity	NPC321852
0.8491	Intermediate Similarity	NPC470391
0.844	Intermediate Similarity	NPC128368
0.844	Intermediate Similarity	NPC13784
0.8435	Intermediate Similarity	NPC46634
0.8426	Intermediate Similarity	NPC291799
0.8411	Intermediate Similarity	NPC469636
0.8378	Intermediate Similarity	NPC100353
0.8378	Intermediate Similarity	NPC226093
0.8365	Intermediate Similarity	NPC188895
0.8364	Intermediate Similarity	NPC153053
0.8302	Intermediate Similarity	NPC269457
0.8288	Intermediate Similarity	NPC228936
0.8288	Intermediate Similarity	NPC306740
0.8286	Intermediate Similarity	NPC255676
0.8273	Intermediate Similarity	NPC161611
0.8247	Intermediate Similarity	NPC318107
0.8218	Intermediate Similarity	NPC261181
0.8214	Intermediate Similarity	NPC135730
0.819	Intermediate Similarity	NPC284477
0.8182	Intermediate Similarity	NPC173443
0.8182	Intermediate Similarity	NPC158282
0.8182	Intermediate Similarity	NPC474314
0.8165	Intermediate Similarity	NPC273837
0.8163	Intermediate Similarity	NPC96625
0.8136	Intermediate Similarity	NPC265910
0.8136	Intermediate Similarity	NPC91475
0.8125	Intermediate Similarity	NPC474408
0.8095	Intermediate Similarity	NPC282895
0.8095	Intermediate Similarity	NPC112552
0.8091	Intermediate Similarity	NPC476003
0.807	Intermediate Similarity	NPC45104
0.807	Intermediate Similarity	NPC228318
0.8037	Intermediate Similarity	NPC269644
0.8036	Intermediate Similarity	NPC237366
0.8019	Intermediate Similarity	NPC25458
0.8019	Intermediate Similarity	NPC304873
0.8017	Intermediate Similarity	NPC232958
0.8017	Intermediate Similarity	NPC473243
0.8	Intermediate Similarity	NPC51292
0.8	Intermediate Similarity	NPC217621
0.7983	Intermediate Similarity	NPC295664
0.7983	Intermediate Similarity	NPC107846
0.7983	Intermediate Similarity	NPC246166
0.7982	Intermediate Similarity	NPC470860
0.7981	Intermediate Similarity	NPC253423
0.7981	Intermediate Similarity	NPC270654
0.798	Intermediate Similarity	NPC89377
0.7966	Intermediate Similarity	NPC223351
0.7965	Intermediate Similarity	NPC474095
0.7963	Intermediate Similarity	NPC105899
0.7961	Intermediate Similarity	NPC5472
0.7949	Intermediate Similarity	NPC50872
0.7949	Intermediate Similarity	NPC144547
0.7946	Intermediate Similarity	NPC474176
0.7934	Intermediate Similarity	NPC181715
0.7931	Intermediate Similarity	NPC204784
0.7921	Intermediate Similarity	NPC62765
0.7917	Intermediate Similarity	NPC121272
0.7913	Intermediate Similarity	NPC217423
0.7909	Intermediate Similarity	NPC281604
0.7909	Intermediate Similarity	NPC192577
0.7909	Intermediate Similarity	NPC318327
0.79	Intermediate Similarity	NPC304760
0.7895	Intermediate Similarity	NPC188907
0.7895	Intermediate Similarity	NPC220540
0.789	Intermediate Similarity	NPC1065
0.7876	Intermediate Similarity	NPC474363
0.7864	Intermediate Similarity	NPC23453
0.7863	Intermediate Similarity	NPC289432
0.7863	Intermediate Similarity	NPC988
0.7857	Intermediate Similarity	NPC23332
0.7857	Intermediate Similarity	NPC66208
0.7843	Intermediate Similarity	NPC119631
0.783	Intermediate Similarity	NPC98911
0.783	Intermediate Similarity	NPC472318
0.7822	Intermediate Similarity	NPC220893
0.7818	Intermediate Similarity	NPC156648
0.7807	Intermediate Similarity	NPC186933
0.7807	Intermediate Similarity	NPC470764
0.7807	Intermediate Similarity	NPC81808
0.7778	Intermediate Similarity	NPC234305
0.7778	Intermediate Similarity	NPC294134
0.7778	Intermediate Similarity	NPC58616
0.7768	Intermediate Similarity	NPC137315
0.7768	Intermediate Similarity	NPC183648
0.7767	Intermediate Similarity	NPC77273
0.7759	Intermediate Similarity	NPC240664
0.7755	Intermediate Similarity	NPC288903
0.775	Intermediate Similarity	NPC228739
0.7748	Intermediate Similarity	NPC40178
0.7732	Intermediate Similarity	NPC71795
0.7719	Intermediate Similarity	NPC279916
0.7714	Intermediate Similarity	NPC61944
0.7712	Intermediate Similarity	NPC230951
0.7712	Intermediate Similarity	NPC470092
0.7712	Intermediate Similarity	NPC238861
0.7712	Intermediate Similarity	NPC77000
0.7706	Intermediate Similarity	NPC85977
0.7692	Intermediate Similarity	NPC32298
0.7692	Intermediate Similarity	NPC27633
0.7692	Intermediate Similarity	NPC94298
0.7692	Intermediate Similarity	NPC94637
0.7686	Intermediate Similarity	NPC470163
0.7686	Intermediate Similarity	NPC470162
0.7685	Intermediate Similarity	NPC244427
0.7685	Intermediate Similarity	NPC222390
0.7679	Intermediate Similarity	NPC259554
0.7679	Intermediate Similarity	NPC234639
0.7672	Intermediate Similarity	NPC128825
0.7672	Intermediate Similarity	NPC190298
0.7672	Intermediate Similarity	NPC131192
0.767	Intermediate Similarity	NPC110704
0.7661	Intermediate Similarity	NPC471832
0.7658	Intermediate Similarity	NPC47536
0.7658	Intermediate Similarity	NPC203732
0.7658	Intermediate Similarity	NPC249811
0.7658	Intermediate Similarity	NPC211439
0.7653	Intermediate Similarity	NPC99240
0.7642	Intermediate Similarity	NPC37512
0.7642	Intermediate Similarity	NPC156021
0.7632	Intermediate Similarity	NPC17693
0.7627	Intermediate Similarity	NPC90522
0.7627	Intermediate Similarity	NPC328459
0.7627	Intermediate Similarity	NPC54243
0.7627	Intermediate Similarity	NPC61779
0.7624	Intermediate Similarity	NPC286608
0.7624	Intermediate Similarity	NPC169050
0.7623	Intermediate Similarity	NPC165556
0.7623	Intermediate Similarity	NPC476599
0.7623	Intermediate Similarity	NPC275576
0.7623	Intermediate Similarity	NPC470765
0.7615	Intermediate Similarity	NPC274443
0.7615	Intermediate Similarity	NPC329556
0.7611	Intermediate Similarity	NPC474057
0.7607	Intermediate Similarity	NPC469954
0.7607	Intermediate Similarity	NPC469574
0.7603	Intermediate Similarity	NPC182646
0.76	Intermediate Similarity	NPC473271
0.76	Intermediate Similarity	NPC53299
0.76	Intermediate Similarity	NPC475478
0.7593	Intermediate Similarity	NPC473325
0.7573	Intermediate Similarity	NPC240108

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 NPC209632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	998
0.2-0.3	1300
0.3-0.4	2749
0.4-0.5	2078
0.5-0.6	1158
0.6-0.7	382
0.7-0.8	88
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8922	High Similarity	NPD164	Approved
0.8868	High Similarity	NPD1609	Clinical (unspecified phase)
0.8774	High Similarity	NPD2181	Clinical (unspecified phase)
0.8762	High Similarity	NPD2182	Approved
0.8713	High Similarity	NPD1238	Approved
0.8247	Intermediate Similarity	NPD9257	Approved
0.8247	Intermediate Similarity	NPD9259	Approved
0.8218	Intermediate Similarity	NPD1202	Approved
0.8125	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5909	Discontinued
0.7921	Intermediate Similarity	NPD9258	Approved
0.7921	Intermediate Similarity	NPD9256	Approved
0.7748	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1241	Discontinued
0.7712	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9545	Approved
0.7672	Intermediate Similarity	NPD9493	Approved
0.7652	Intermediate Similarity	NPD5951	Approved
0.7624	Intermediate Similarity	NPD1282	Approved
0.7619	Intermediate Similarity	NPD9260	Approved
0.7615	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1929	Approved
0.7615	Intermediate Similarity	NPD1930	Approved
0.7583	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6287	Discontinued
0.7541	Intermediate Similarity	NPD1876	Approved
0.7526	Intermediate Similarity	NPD9490	Approved
0.7522	Intermediate Similarity	NPD2067	Discontinued
0.7521	Intermediate Similarity	NPD9717	Approved
0.752	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2066	Phase 3
0.7477	Intermediate Similarity	NPD9697	Approved
0.746	Intermediate Similarity	NPD3764	Approved
0.7455	Intermediate Similarity	NPD9261	Approved
0.7451	Intermediate Similarity	NPD650	Approved
0.7451	Intermediate Similarity	NPD1087	Approved
0.744	Intermediate Similarity	NPD6832	Phase 2
0.7438	Intermediate Similarity	NPD1281	Approved
0.7419	Intermediate Similarity	NPD2798	Approved
0.7417	Intermediate Similarity	NPD17	Approved
0.74	Intermediate Similarity	NPD9491	Approved
0.7387	Intermediate Similarity	NPD1237	Approved
0.7385	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD1989	Approved
0.7381	Intermediate Similarity	NPD7008	Discontinued
0.7377	Intermediate Similarity	NPD3972	Approved
0.7344	Intermediate Similarity	NPD4307	Phase 2
0.7339	Intermediate Similarity	NPD3266	Approved
0.7339	Intermediate Similarity	NPD1203	Approved
0.7339	Intermediate Similarity	NPD3267	Approved
0.7339	Intermediate Similarity	NPD2797	Approved
0.7323	Intermediate Similarity	NPD2313	Discontinued
0.7295	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1283	Approved
0.7258	Intermediate Similarity	NPD2198	Approved
0.7258	Intermediate Similarity	NPD2199	Approved
0.7257	Intermediate Similarity	NPD3134	Approved
0.7248	Intermediate Similarity	NPD9495	Approved
0.7245	Intermediate Similarity	NPD227	Approved
0.7245	Intermediate Similarity	NPD225	Approved
0.7238	Intermediate Similarity	NPD1089	Approved
0.7238	Intermediate Similarity	NPD1090	Approved
0.7238	Intermediate Similarity	NPD1086	Approved
0.7236	Intermediate Similarity	NPD1608	Approved
0.7207	Intermediate Similarity	NPD1932	Approved
0.7196	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1563	Approved
0.7193	Intermediate Similarity	NPD9267	Approved
0.7193	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9263	Approved
0.7193	Intermediate Similarity	NPD1358	Approved
0.7193	Intermediate Similarity	NPD9264	Approved
0.717	Intermediate Similarity	NPD1239	Approved
0.717	Intermediate Similarity	NPD7609	Phase 3
0.7143	Intermediate Similarity	NPD800	Approved
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD74	Approved
0.713	Intermediate Similarity	NPD9266	Approved
0.713	Intermediate Similarity	NPD1693	Approved
0.7121	Intermediate Similarity	NPD2799	Discontinued
0.7121	Intermediate Similarity	NPD4308	Phase 3
0.7111	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD1894	Discontinued
0.7103	Intermediate Similarity	NPD1088	Approved
0.7103	Intermediate Similarity	NPD7631	Approved
0.709	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3673	Approved
0.7075	Intermediate Similarity	NPD3672	Approved
0.7069	Intermediate Similarity	NPD5239	Approved
0.7069	Intermediate Similarity	NPD5235	Approved
0.7069	Intermediate Similarity	NPD5237	Approved
0.7069	Intermediate Similarity	NPD5240	Approved
0.7069	Intermediate Similarity	NPD5236	Approved
0.7054	Intermediate Similarity	NPD3268	Approved
0.7049	Intermediate Similarity	NPD1651	Approved
0.7049	Intermediate Similarity	NPD5691	Approved
0.7034	Intermediate Similarity	NPD5277	Phase 2
0.703	Intermediate Similarity	NPD942	Approved
0.703	Intermediate Similarity	NPD226	Approved
0.7023	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1933	Approved
0.7015	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2201	Approved
0.7	Intermediate Similarity	NPD1564	Approved
0.7	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD1565	Approved
0.6991	Remote Similarity	NPD6647	Phase 2
0.6985	Remote Similarity	NPD7003	Approved
0.6983	Remote Similarity	NPD2329	Discontinued
0.696	Remote Similarity	NPD6637	Approved
0.696	Remote Similarity	NPD1481	Phase 2
0.6949	Remote Similarity	NPD9508	Approved
0.6947	Remote Similarity	NPD2979	Phase 3
0.6944	Remote Similarity	NPD1508	Approved
0.6929	Remote Similarity	NPD552	Approved
0.6929	Remote Similarity	NPD9567	Approved
0.6929	Remote Similarity	NPD553	Approved
0.6923	Remote Similarity	NPD411	Approved
0.6917	Remote Similarity	NPD2629	Approved
0.6911	Remote Similarity	NPD5585	Approved
0.6905	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD447	Suspended
0.6893	Remote Similarity	NPD3971	Phase 1
0.6891	Remote Similarity	NPD5535	Approved
0.6889	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2353	Approved
0.6889	Remote Similarity	NPD1471	Phase 3
0.6885	Remote Similarity	NPD2347	Approved
0.688	Remote Similarity	NPD1535	Discovery
0.687	Remote Similarity	NPD8032	Phase 2
0.6861	Remote Similarity	NPD4628	Phase 3
0.6857	Remote Similarity	NPD6273	Approved
0.6855	Remote Similarity	NPD4626	Approved
0.685	Remote Similarity	NPD5667	Approved
0.6847	Remote Similarity	NPD3495	Discontinued
0.6825	Remote Similarity	NPD4878	Approved
0.6818	Remote Similarity	NPD3142	Approved
0.6818	Remote Similarity	NPD3373	Approved
0.6818	Remote Similarity	NPD3140	Approved
0.6815	Remote Similarity	NPD2935	Discontinued
0.68	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1164	Approved
0.6794	Remote Similarity	NPD1296	Phase 2
0.6791	Remote Similarity	NPD2569	Approved
0.6791	Remote Similarity	NPD2567	Approved
0.6788	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1243	Approved
0.6786	Remote Similarity	NPD5926	Approved
0.6777	Remote Similarity	NPD9281	Approved
0.6774	Remote Similarity	NPD4102	Approved
0.6774	Remote Similarity	NPD4105	Approved
0.6765	Remote Similarity	NPD7611	Approved
0.6765	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1843	Approved
0.6746	Remote Similarity	NPD422	Phase 1
0.6746	Remote Similarity	NPD1201	Approved
0.6746	Remote Similarity	NPD1611	Approved
0.6744	Remote Similarity	NPD2788	Approved
0.6742	Remote Similarity	NPD7713	Phase 3
0.6739	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4198	Discontinued
0.672	Remote Similarity	NPD5305	Approved
0.672	Remote Similarity	NPD5306	Approved
0.6719	Remote Similarity	NPD3225	Approved
0.6718	Remote Similarity	NPD6039	Approved
0.6716	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3226	Approved
0.6693	Remote Similarity	NPD1877	Discontinued
0.6692	Remote Similarity	NPD1240	Approved
0.6691	Remote Similarity	NPD3887	Approved
0.6691	Remote Similarity	NPD2796	Approved
0.6691	Remote Similarity	NPD1551	Phase 2
0.6691	Remote Similarity	NPD4477	Approved
0.6691	Remote Similarity	NPD2438	Suspended
0.6691	Remote Similarity	NPD2531	Phase 2
0.6691	Remote Similarity	NPD4476	Approved
0.6691	Remote Similarity	NPD2354	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD5347	Phase 2
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD5346	Phase 2
0.6667	Remote Similarity	NPD969	Suspended
0.6643	Remote Similarity	NPD7236	Approved
0.6642	Remote Similarity	NPD4622	Approved
0.6642	Remote Similarity	NPD2344	Approved
0.6642	Remote Similarity	NPD4618	Approved
0.6642	Remote Similarity	NPD230	Phase 1
0.6641	Remote Similarity	NPD4359	Approved
0.664	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1752	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