NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.07
Volume:	215.417
LogP:	2.7
LogD:	3.16
LogS:	-3.935
# Rotatable Bonds:	2
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.553
Fsp3:	0.0
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:	-4.829
MDCK Permeability:	1.346333920082543e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.463
30% Bioavailability (F30%):	0.308

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	90.5693588256836%
Volume Distribution (VD):	0.444
Pgp-substrate:	11.791824340820312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.63
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.193
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	1.465
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.616
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.364
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.375
Skin Sensitization:	0.773
Carcinogencity:	0.844
Eye Corrosion:	0.398
Eye Irritation:	0.988
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC114594

Natural Product ID:	NPC114594
*Common Name:**	(E/Z)-Dracumerin
IUPAC Name:	3-[(1E)-buta-1,3-dienyl]isochromen-1-one
Synonyms:	(E/Z)-Dracumerin
Standard InCHIKey:	NCJLODXKOVAPFB-XVNBXDOJSA-N
Standard InCHI:	InChI=1S/C13H10O2/c1-2-3-7-11-9-10-6-4-5-8-12(10)13(14)15-11/h2-9H,1H2/b7-3+
SMILES:	C=C/C=C/c1cc2ccccc2c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460603
PubChem CID:	11275633
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	=	25.0	ug	PMID[461295]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	50.0	ug.mL-1	PMID[461295]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	45.0	ug ml-1	PMID[461295]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	14.0	ug.mL-1	PMID[461295]

☑ 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 NPC114594 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	427
0.1-0.2	2312
0.2-0.3	5311
0.3-0.4	11950
0.4-0.5	5859
0.5-0.6	7318
0.6-0.7	7876
0.7-0.8	1539
0.8-0.85	74
0.85-0.9	13
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC209632
0.96	High Similarity	NPC269023
0.96	High Similarity	NPC99846
0.949	High Similarity	NPC60679
0.9412	High Similarity	NPC474157
0.94	High Similarity	NPC37622
0.94	High Similarity	NPC30594
0.9231	High Similarity	NPC272524
0.9223	High Similarity	NPC243355
0.9143	High Similarity	NPC308744
0.9057	High Similarity	NPC474685
0.9057	High Similarity	NPC210092
0.9	High Similarity	NPC45613
0.8911	High Similarity	NPC89886
0.89	High Similarity	NPC42211
0.8857	High Similarity	NPC210089
0.8846	High Similarity	NPC83628
0.8846	High Similarity	NPC265407
0.8835	High Similarity	NPC119271
0.8824	High Similarity	NPC31786
0.88	High Similarity	NPC325497
0.88	High Similarity	NPC118343
0.8788	High Similarity	NPC92754
0.8788	High Similarity	NPC276775
0.8788	High Similarity	NPC249912
0.8776	High Similarity	NPC130398
0.8774	High Similarity	NPC212415
0.875	High Similarity	NPC56493
0.87	High Similarity	NPC225060
0.87	High Similarity	NPC35448
0.87	High Similarity	NPC78701
0.8679	High Similarity	NPC167504
0.8667	High Similarity	NPC17417
0.8667	High Similarity	NPC10251
0.8624	High Similarity	NPC149691
0.8614	High Similarity	NPC146351
0.8611	High Similarity	NPC196075
0.8598	High Similarity	NPC79496
0.8585	High Similarity	NPC196246
0.8585	High Similarity	NPC174099
0.8585	High Similarity	NPC214067
0.8585	High Similarity	NPC93084
0.8585	High Similarity	NPC251854
0.8544	High Similarity	NPC474365
0.8544	High Similarity	NPC301943
0.8529	High Similarity	NPC70624
0.8515	High Similarity	NPC229242
0.8505	High Similarity	NPC1082
0.8505	High Similarity	NPC260818
0.8505	High Similarity	NPC305912
0.8491	Intermediate Similarity	NPC85493
0.8491	Intermediate Similarity	NPC474364
0.8455	Intermediate Similarity	NPC100353
0.844	Intermediate Similarity	NPC307651
0.844	Intermediate Similarity	NPC477411
0.8431	Intermediate Similarity	NPC203925
0.8426	Intermediate Similarity	NPC82899
0.8426	Intermediate Similarity	NPC321852
0.8426	Intermediate Similarity	NPC270699
0.8396	Intermediate Similarity	NPC470391
0.8381	Intermediate Similarity	NPC269457
0.8365	Intermediate Similarity	NPC255676
0.8364	Intermediate Similarity	NPC306740
0.8349	Intermediate Similarity	NPC128368
0.8349	Intermediate Similarity	NPC13784
0.8348	Intermediate Similarity	NPC46634
0.8333	Intermediate Similarity	NPC318107
0.8333	Intermediate Similarity	NPC291799
0.8318	Intermediate Similarity	NPC469636
0.83	Intermediate Similarity	NPC261181
0.8288	Intermediate Similarity	NPC226093
0.8273	Intermediate Similarity	NPC153053
0.8269	Intermediate Similarity	NPC188895
0.8269	Intermediate Similarity	NPC284477
0.8257	Intermediate Similarity	NPC158282
0.8257	Intermediate Similarity	NPC474314
0.8198	Intermediate Similarity	NPC228936
0.8182	Intermediate Similarity	NPC161611
0.8173	Intermediate Similarity	NPC282895
0.8142	Intermediate Similarity	NPC228318
0.8125	Intermediate Similarity	NPC135730
0.8113	Intermediate Similarity	NPC269644
0.8108	Intermediate Similarity	NPC237366
0.8081	Intermediate Similarity	NPC173443
0.8073	Intermediate Similarity	NPC273837
0.8061	Intermediate Similarity	NPC96625
0.8058	Intermediate Similarity	NPC270654
0.8051	Intermediate Similarity	NPC107846
0.8051	Intermediate Similarity	NPC265910
0.8051	Intermediate Similarity	NPC91475
0.8036	Intermediate Similarity	NPC474408
0.8018	Intermediate Similarity	NPC474176
0.8	Intermediate Similarity	NPC476003
0.8	Intermediate Similarity	NPC112552
0.8	Intermediate Similarity	NPC62765
0.7982	Intermediate Similarity	NPC45104
0.7982	Intermediate Similarity	NPC318327
0.7931	Intermediate Similarity	NPC473243
0.7931	Intermediate Similarity	NPC232958
0.7925	Intermediate Similarity	NPC304873
0.7925	Intermediate Similarity	NPC25458
0.7921	Intermediate Similarity	NPC119631
0.7917	Intermediate Similarity	NPC51292
0.7905	Intermediate Similarity	NPC217621
0.7905	Intermediate Similarity	NPC98911
0.7905	Intermediate Similarity	NPC472318
0.7899	Intermediate Similarity	NPC295664
0.7899	Intermediate Similarity	NPC246166
0.7895	Intermediate Similarity	NPC470860
0.789	Intermediate Similarity	NPC156648
0.7885	Intermediate Similarity	NPC253423
0.7881	Intermediate Similarity	NPC223351
0.7879	Intermediate Similarity	NPC89377
0.7876	Intermediate Similarity	NPC474095
0.787	Intermediate Similarity	NPC105899
0.7864	Intermediate Similarity	NPC5472
0.7863	Intermediate Similarity	NPC50872
0.7863	Intermediate Similarity	NPC144547
0.7851	Intermediate Similarity	NPC181715
0.7845	Intermediate Similarity	NPC204784
0.7843	Intermediate Similarity	NPC77273
0.7833	Intermediate Similarity	NPC121272
0.7826	Intermediate Similarity	NPC217423
0.7818	Intermediate Similarity	NPC281604
0.7818	Intermediate Similarity	NPC192577
0.7818	Intermediate Similarity	NPC40178
0.7812	Intermediate Similarity	NPC71795
0.7807	Intermediate Similarity	NPC188907
0.7807	Intermediate Similarity	NPC220540
0.78	Intermediate Similarity	NPC304760
0.7798	Intermediate Similarity	NPC1065
0.7788	Intermediate Similarity	NPC279916
0.7788	Intermediate Similarity	NPC61944
0.7788	Intermediate Similarity	NPC474363
0.7778	Intermediate Similarity	NPC988
0.7778	Intermediate Similarity	NPC289432
0.7768	Intermediate Similarity	NPC66208
0.7768	Intermediate Similarity	NPC23332
0.7767	Intermediate Similarity	NPC23453
0.7759	Intermediate Similarity	NPC32298
0.7745	Intermediate Similarity	NPC110704
0.7739	Intermediate Similarity	NPC190298
0.7727	Intermediate Similarity	NPC47536
0.7727	Intermediate Similarity	NPC211439
0.7723	Intermediate Similarity	NPC220893
0.7719	Intermediate Similarity	NPC470764
0.7719	Intermediate Similarity	NPC186933
0.7719	Intermediate Similarity	NPC81808
0.7714	Intermediate Similarity	NPC156021
0.7692	Intermediate Similarity	NPC54243
0.7685	Intermediate Similarity	NPC234305
0.7679	Intermediate Similarity	NPC137315
0.7679	Intermediate Similarity	NPC183648
0.7677	Intermediate Similarity	NPC58616
0.7677	Intermediate Similarity	NPC294134
0.7672	Intermediate Similarity	NPC469574
0.7672	Intermediate Similarity	NPC240664
0.7667	Intermediate Similarity	NPC228739
0.7664	Intermediate Similarity	NPC473325
0.7653	Intermediate Similarity	NPC288903
0.7647	Intermediate Similarity	NPC240108
0.7647	Intermediate Similarity	NPC213156
0.7632	Intermediate Similarity	NPC87069
0.7627	Intermediate Similarity	NPC238861
0.7627	Intermediate Similarity	NPC77000
0.7627	Intermediate Similarity	NPC233282
0.7627	Intermediate Similarity	NPC230951
0.7627	Intermediate Similarity	NPC470092
0.7615	Intermediate Similarity	NPC85977
0.7611	Intermediate Similarity	NPC233238
0.7607	Intermediate Similarity	NPC27633
0.7607	Intermediate Similarity	NPC94298
0.7607	Intermediate Similarity	NPC94637
0.7603	Intermediate Similarity	NPC470162
0.7603	Intermediate Similarity	NPC470163
0.7593	Intermediate Similarity	NPC244427
0.7593	Intermediate Similarity	NPC222390
0.7589	Intermediate Similarity	NPC259554
0.7589	Intermediate Similarity	NPC234639
0.7586	Intermediate Similarity	NPC128825
0.7586	Intermediate Similarity	NPC158157
0.7586	Intermediate Similarity	NPC131192
0.7581	Intermediate Similarity	NPC471832
0.757	Intermediate Similarity	NPC228435
0.7568	Intermediate Similarity	NPC203732
0.7568	Intermediate Similarity	NPC249811
0.7561	Intermediate Similarity	NPC37512
0.7551	Intermediate Similarity	NPC99240
0.7549	Intermediate Similarity	NPC9822
0.7545	Intermediate Similarity	NPC139891
0.7544	Intermediate Similarity	NPC17693
0.7542	Intermediate Similarity	NPC264976
0.7542	Intermediate Similarity	NPC90522
0.7542	Intermediate Similarity	NPC328459
0.7542	Intermediate Similarity	NPC35744
0.7542	Intermediate Similarity	NPC61779
0.7542	Intermediate Similarity	NPC201284
0.7541	Intermediate Similarity	NPC476599
0.7541	Intermediate Similarity	NPC275576
0.7541	Intermediate Similarity	NPC470765

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 NPC114594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	998
0.2-0.3	1354
0.3-0.4	2783
0.4-0.5	2056
0.5-0.6	1116
0.6-0.7	348
0.7-0.8	79
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD164	Approved
0.88	High Similarity	NPD1238	Approved
0.8774	High Similarity	NPD1609	Clinical (unspecified phase)
0.8679	High Similarity	NPD2181	Clinical (unspecified phase)
0.8667	High Similarity	NPD2182	Approved
0.8333	Intermediate Similarity	NPD9257	Approved
0.8333	Intermediate Similarity	NPD9259	Approved
0.83	Intermediate Similarity	NPD1202	Approved
0.8036	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9256	Approved
0.8	Intermediate Similarity	NPD9258	Approved
0.7944	Intermediate Similarity	NPD5909	Discontinued
0.7692	Intermediate Similarity	NPD9260	Approved
0.7658	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1241	Discontinued
0.7627	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD9545	Approved
0.7604	Intermediate Similarity	NPD9490	Approved
0.7586	Intermediate Similarity	NPD9493	Approved
0.7565	Intermediate Similarity	NPD5951	Approved
0.7545	Intermediate Similarity	NPD9697	Approved
0.7525	Intermediate Similarity	NPD1282	Approved
0.7523	Intermediate Similarity	NPD9261	Approved
0.7523	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1929	Approved
0.7523	Intermediate Similarity	NPD1930	Approved
0.752	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6287	Discontinued
0.7475	Intermediate Similarity	NPD9491	Approved
0.7459	Intermediate Similarity	NPD1876	Approved
0.7455	Intermediate Similarity	NPD1237	Approved
0.7442	Intermediate Similarity	NPD3748	Approved
0.744	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD9717	Approved
0.7434	Intermediate Similarity	NPD2067	Discontinued
0.7407	Intermediate Similarity	NPD2066	Phase 3
0.7398	Intermediate Similarity	NPD1203	Approved
0.7381	Intermediate Similarity	NPD2313	Discontinued
0.736	Intermediate Similarity	NPD6832	Phase 2
0.7358	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1281	Approved
0.7355	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1087	Approved
0.7353	Intermediate Similarity	NPD650	Approved
0.7339	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD17	Approved
0.732	Intermediate Similarity	NPD227	Approved
0.732	Intermediate Similarity	NPD225	Approved
0.7315	Intermediate Similarity	NPD9495	Approved
0.7302	Intermediate Similarity	NPD7008	Discontinued
0.7295	Intermediate Similarity	NPD3972	Approved
0.729	Intermediate Similarity	NPD1989	Approved
0.7273	Intermediate Similarity	NPD1932	Approved
0.7266	Intermediate Similarity	NPD4307	Phase 2
0.7258	Intermediate Similarity	NPD2797	Approved
0.7258	Intermediate Similarity	NPD3267	Approved
0.7258	Intermediate Similarity	NPD3266	Approved
0.7257	Intermediate Similarity	NPD9263	Approved
0.7257	Intermediate Similarity	NPD9264	Approved
0.7257	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9267	Approved
0.7238	Intermediate Similarity	NPD1239	Approved
0.72	Intermediate Similarity	NPD1019	Discontinued
0.72	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7193	Intermediate Similarity	NPD9266	Approved
0.7193	Intermediate Similarity	NPD74	Approved
0.719	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1283	Approved
0.7177	Intermediate Similarity	NPD2198	Approved
0.7177	Intermediate Similarity	NPD2199	Approved
0.7168	Intermediate Similarity	NPD3134	Approved
0.7167	Intermediate Similarity	NPD1894	Discontinued
0.7164	Intermediate Similarity	NPD3750	Approved
0.7154	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1086	Approved
0.7143	Intermediate Similarity	NPD1090	Approved
0.7105	Intermediate Similarity	NPD1358	Approved
0.7103	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1563	Approved
0.71	Intermediate Similarity	NPD942	Approved
0.71	Intermediate Similarity	NPD226	Approved
0.7075	Intermediate Similarity	NPD7609	Phase 3
0.7048	Intermediate Similarity	NPD800	Approved
0.7045	Intermediate Similarity	NPD4308	Phase 3
0.7045	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD1693	Approved
0.7016	Intermediate Similarity	NPD1481	Phase 2
0.7015	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1508	Approved
0.7009	Intermediate Similarity	NPD7631	Approved
0.7009	Intermediate Similarity	NPD1088	Approved
0.7009	Intermediate Similarity	NPD9508	Approved
0.6983	Remote Similarity	NPD5240	Approved
0.6983	Remote Similarity	NPD5237	Approved
0.6983	Remote Similarity	NPD5235	Approved
0.6983	Remote Similarity	NPD5236	Approved
0.6983	Remote Similarity	NPD5239	Approved
0.6981	Remote Similarity	NPD3673	Approved
0.6981	Remote Similarity	NPD3672	Approved
0.6977	Remote Similarity	NPD3268	Approved
0.6967	Remote Similarity	NPD5691	Approved
0.6967	Remote Similarity	NPD1651	Approved
0.6949	Remote Similarity	NPD5277	Phase 2
0.6947	Remote Similarity	NPD1933	Approved
0.6947	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1535	Discovery
0.6923	Remote Similarity	NPD2201	Approved
0.6912	Remote Similarity	NPD7003	Approved
0.6909	Remote Similarity	NPD1564	Approved
0.6909	Remote Similarity	NPD1565	Approved
0.6909	Remote Similarity	NPD1566	Phase 3
0.6903	Remote Similarity	NPD6647	Phase 2
0.6897	Remote Similarity	NPD2329	Discontinued
0.688	Remote Similarity	NPD6637	Approved
0.688	Remote Similarity	NPD4878	Approved
0.687	Remote Similarity	NPD2979	Phase 3
0.685	Remote Similarity	NPD553	Approved
0.685	Remote Similarity	NPD1164	Approved
0.685	Remote Similarity	NPD552	Approved
0.685	Remote Similarity	NPD9567	Approved
0.6846	Remote Similarity	NPD1296	Phase 2
0.6846	Remote Similarity	NPD411	Approved
0.6833	Remote Similarity	NPD2629	Approved
0.6833	Remote Similarity	NPD9281	Approved
0.6829	Remote Similarity	NPD5585	Approved
0.6825	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD447	Suspended
0.6818	Remote Similarity	NPD1843	Approved
0.6815	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1471	Phase 3
0.6815	Remote Similarity	NPD2353	Approved
0.6807	Remote Similarity	NPD5535	Approved
0.6803	Remote Similarity	NPD2347	Approved
0.68	Remote Similarity	NPD1201	Approved
0.6796	Remote Similarity	NPD3971	Phase 1
0.6794	Remote Similarity	NPD8032	Phase 2
0.6788	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD6273	Approved
0.6774	Remote Similarity	NPD4626	Approved
0.6772	Remote Similarity	NPD5667	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6757	Remote Similarity	NPD3495	Discontinued
0.6742	Remote Similarity	NPD3373	Approved
0.6742	Remote Similarity	NPD3142	Approved
0.6742	Remote Similarity	NPD3140	Approved
0.6741	Remote Similarity	NPD2935	Discontinued
0.6741	Remote Similarity	NPD1551	Phase 2
0.6723	Remote Similarity	NPD969	Suspended
0.672	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1470	Approved
0.6716	Remote Similarity	NPD2567	Approved
0.6716	Remote Similarity	NPD2569	Approved
0.6715	Remote Similarity	NPD1243	Approved
0.6715	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4793	Discontinued
0.6696	Remote Similarity	NPD5926	Approved
0.6694	Remote Similarity	NPD4105	Approved
0.6694	Remote Similarity	NPD4102	Approved
0.6691	Remote Similarity	NPD7611	Approved
0.6691	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2788	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD9716	Approved
0.6643	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3226	Approved
0.6642	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6039	Approved
0.664	Remote Similarity	NPD5306	Approved
0.664	Remote Similarity	NPD5305	Approved
0.6639	Remote Similarity	NPD4198	Discontinued
0.6639	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7798	Approved
0.6619	Remote Similarity	NPD2354	Approved
0.6619	Remote Similarity	NPD3887	Approved
0.6618	Remote Similarity	NPD2438	Suspended
0.6618	Remote Similarity	NPD4476	Approved
0.6618	Remote Similarity	NPD2796	Approved
0.6618	Remote Similarity	NPD2531	Phase 2
0.6618	Remote Similarity	NPD4477	Approved
0.6617	Remote Similarity	NPD1240	Approved
0.6615	Remote Similarity	NPD454	Approved
0.6614	Remote Similarity	NPD1877	Discontinued
0.6596	Remote Similarity	NPD5401	Approved
0.6587	Remote Similarity	NPD4136	Approved
0.6587	Remote Similarity	NPD4106	Approved
0.6587	Remote Similarity	NPD1889	Phase 1
0.6587	Remote Similarity	NPD4135	Approved
0.6587	Remote Similarity	NPD3847	Discontinued
0.6585	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5346	Phase 2
0.6574	Remote Similarity	NPD5347	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