NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.03
Volume:	215.968
LogP:	3.206
LogD:	2.388
LogS:	-4.738
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.425
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.571
MDCK Permeability:	1.7778147594071925e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.7488784790039%
Volume Distribution (VD):	0.795
Pgp-substrate:	1.5915277004241943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	3.767
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.776
Carcinogencity:	0.777
Eye Corrosion:	0.329
Eye Irritation:	0.991
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC474910

Natural Product ID:	NPC474910
*Common Name:**	8-Chloro-2,7-Dimethyl-1,4-Naphthoquinone
IUPAC Name:	8-chloro-2,7-dimethylnaphthalene-1,4-dione
Synonyms:	8-chlorochimaphilin
Standard InCHIKey:	YCCXVFNHLXWDSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H9ClO2/c1-6-3-4-8-9(14)5-7(2)12(15)10(8)11(6)13/h3-5H,1-2H3
SMILES:	CC1=CC(=O)c2c(C1=O)c(Cl)c(cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487352
PubChem CID:	10376193
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO29252	Moneses uniflora	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984155]
NPO29252	Moneses uniflora	Species	Ericaceae	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
MIC	15

Activity Type	# Activity
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	800.0	ug.mL-1	PMID[569977]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	800.0	ug.mL-1	PMID[569977]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	800.0	ug.mL-1	PMID[569977]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	400.0	ug.mL-1	PMID[569977]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[569977]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	200.0	ug.mL-1	PMID[569977]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[569977]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[569977]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	100.0	ug.mL-1	PMID[569977]
NPT3480	Organism	Yarrowia lipolytica	Yarrowia lipolytica	MIC	=	50.0	ug.mL-1	PMID[569977]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	100.0	ug.mL-1	PMID[569977]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	3.1	ug.mL-1	PMID[569977]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MIC	=	12.5	ug.mL-1	PMID[569977]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	25.0	ug.mL-1	PMID[569977]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	25.0	ug.mL-1	PMID[569977]

☑ 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 NPC474910 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	421
0.1-0.2	2398
0.2-0.3	8479
0.3-0.4	16679
0.4-0.5	11932
0.5-0.6	2376
0.6-0.7	324
0.7-0.8	66
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.866	High Similarity	NPC173413
0.8485	Intermediate Similarity	NPC155232
0.8454	Intermediate Similarity	NPC157778
0.84	Intermediate Similarity	NPC238219
0.8384	Intermediate Similarity	NPC133461
0.8351	Intermediate Similarity	NPC43945
0.83	Intermediate Similarity	NPC153885
0.8247	Intermediate Similarity	NPC160339
0.8247	Intermediate Similarity	NPC307
0.8218	Intermediate Similarity	NPC289883
0.82	Intermediate Similarity	NPC284475
0.8137	Intermediate Similarity	NPC260233
0.8119	Intermediate Similarity	NPC188844
0.8119	Intermediate Similarity	NPC1682
0.81	Intermediate Similarity	NPC277277
0.8077	Intermediate Similarity	NPC134882
0.8077	Intermediate Similarity	NPC75724
0.8077	Intermediate Similarity	NPC49994
0.7981	Intermediate Similarity	NPC239185
0.7981	Intermediate Similarity	NPC265220
0.7941	Intermediate Similarity	NPC59677
0.7938	Intermediate Similarity	NPC215008
0.7925	Intermediate Similarity	NPC109514
0.7925	Intermediate Similarity	NPC476993
0.7921	Intermediate Similarity	NPC19256
0.7822	Intermediate Similarity	NPC418308
0.7767	Intermediate Similarity	NPC323420
0.7732	Intermediate Similarity	NPC145053
0.7723	Intermediate Similarity	NPC267262
0.7723	Intermediate Similarity	NPC153308
0.7714	Intermediate Similarity	NPC219573
0.7714	Intermediate Similarity	NPC185208
0.7636	Intermediate Similarity	NPC172483
0.7624	Intermediate Similarity	NPC69057
0.7619	Intermediate Similarity	NPC472880
0.7615	Intermediate Similarity	NPC247976
0.7576	Intermediate Similarity	NPC149263
0.7526	Intermediate Similarity	NPC300205
0.7525	Intermediate Similarity	NPC164526
0.75	Intermediate Similarity	NPC103346
0.7455	Intermediate Similarity	NPC274443
0.7449	Intermediate Similarity	NPC164086
0.7449	Intermediate Similarity	NPC190567
0.7434	Intermediate Similarity	NPC470252
0.7431	Intermediate Similarity	NPC472879
0.7423	Intermediate Similarity	NPC36342
0.7423	Intermediate Similarity	NPC2785
0.7423	Intermediate Similarity	NPC285470
0.7411	Intermediate Similarity	NPC100767
0.74	Intermediate Similarity	NPC273758
0.7387	Intermediate Similarity	NPC329282
0.7374	Intermediate Similarity	NPC12936
0.7374	Intermediate Similarity	NPC273033
0.7364	Intermediate Similarity	NPC222390
0.7364	Intermediate Similarity	NPC244427
0.732	Intermediate Similarity	NPC245966
0.7308	Intermediate Similarity	NPC325709
0.7308	Intermediate Similarity	NPC113307
0.7273	Intermediate Similarity	NPC17408
0.7273	Intermediate Similarity	NPC285716
0.7273	Intermediate Similarity	NPC71664
0.7255	Intermediate Similarity	NPC252067
0.7241	Intermediate Similarity	NPC292834
0.7228	Intermediate Similarity	NPC197581
0.7228	Intermediate Similarity	NPC39600
0.7179	Intermediate Similarity	NPC470253
0.7155	Intermediate Similarity	NPC474057
0.7143	Intermediate Similarity	NPC298115
0.713	Intermediate Similarity	NPC192577
0.7119	Intermediate Similarity	NPC326664
0.7117	Intermediate Similarity	NPC112552
0.7071	Intermediate Similarity	NPC103488
0.7059	Intermediate Similarity	NPC217111
0.7043	Intermediate Similarity	NPC203732
0.7034	Intermediate Similarity	NPC143768
0.703	Intermediate Similarity	NPC100039
0.703	Intermediate Similarity	NPC73978
0.7018	Intermediate Similarity	NPC134120
0.7009	Intermediate Similarity	NPC265513
0.7009	Intermediate Similarity	NPC137315
0.7	Intermediate Similarity	NPC156021
0.6991	Remote Similarity	NPC475939
0.6991	Remote Similarity	NPC471829
0.6991	Remote Similarity	NPC472691
0.6991	Remote Similarity	NPC474866
0.6975	Remote Similarity	NPC67377
0.6949	Remote Similarity	NPC280789
0.6949	Remote Similarity	NPC186128
0.6942	Remote Similarity	NPC469843
0.6931	Remote Similarity	NPC95868
0.6916	Remote Similarity	NPC110420
0.6916	Remote Similarity	NPC67585
0.6916	Remote Similarity	NPC58872
0.6916	Remote Similarity	NPC303967
0.6907	Remote Similarity	NPC285679
0.6891	Remote Similarity	NPC93287
0.6891	Remote Similarity	NPC13784
0.6864	Remote Similarity	NPC291799
0.6842	Remote Similarity	NPC329556
0.6833	Remote Similarity	NPC241851
0.6833	Remote Similarity	NPC471721
0.6833	Remote Similarity	NPC196673
0.6832	Remote Similarity	NPC151405
0.6832	Remote Similarity	NPC139901
0.6829	Remote Similarity	NPC318173
0.681	Remote Similarity	NPC83409
0.681	Remote Similarity	NPC37914
0.681	Remote Similarity	NPC472699
0.681	Remote Similarity	NPC472700
0.681	Remote Similarity	NPC185763
0.6804	Remote Similarity	NPC74458
0.6783	Remote Similarity	NPC324786
0.6777	Remote Similarity	NPC228936
0.6777	Remote Similarity	NPC474095
0.6777	Remote Similarity	NPC470764
0.6777	Remote Similarity	NPC215419
0.6777	Remote Similarity	NPC113099
0.6752	Remote Similarity	NPC472683
0.6752	Remote Similarity	NPC472695
0.6752	Remote Similarity	NPC470391
0.6752	Remote Similarity	NPC472701
0.6752	Remote Similarity	NPC472696
0.6752	Remote Similarity	NPC112903
0.6748	Remote Similarity	NPC80605
0.6748	Remote Similarity	NPC323440
0.6748	Remote Similarity	NPC222968
0.6731	Remote Similarity	NPC324624
0.6723	Remote Similarity	NPC210089
0.6721	Remote Similarity	NPC135730
0.6697	Remote Similarity	NPC125226
0.6696	Remote Similarity	NPC291426
0.6696	Remote Similarity	NPC240042
0.6695	Remote Similarity	NPC318327
0.6667	Remote Similarity	NPC66208
0.6667	Remote Similarity	NPC272260
0.6667	Remote Similarity	NPC218855
0.6667	Remote Similarity	NPC212415
0.6667	Remote Similarity	NPC158157
0.664	Remote Similarity	NPC202015
0.6639	Remote Similarity	NPC186933
0.6639	Remote Similarity	NPC93181
0.6634	Remote Similarity	NPC9796
0.6612	Remote Similarity	NPC471481
0.6609	Remote Similarity	NPC25458
0.6606	Remote Similarity	NPC26224
0.6602	Remote Similarity	NPC157055
0.6602	Remote Similarity	NPC477703
0.6598	Remote Similarity	NPC98880
0.6587	Remote Similarity	NPC232958
0.6585	Remote Similarity	NPC62138
0.6574	Remote Similarity	NPC473345
0.6569	Remote Similarity	NPC137847
0.6569	Remote Similarity	NPC76455
0.6562	Remote Similarity	NPC307174
0.6557	Remote Similarity	NPC130591
0.6557	Remote Similarity	NPC477411
0.6557	Remote Similarity	NPC234637
0.6557	Remote Similarity	NPC196075
0.6549	Remote Similarity	NPC226041
0.6545	Remote Similarity	NPC476484
0.6535	Remote Similarity	NPC144547
0.6535	Remote Similarity	NPC472981
0.6535	Remote Similarity	NPC78500
0.6531	Remote Similarity	NPC95289
0.6522	Remote Similarity	NPC225079
0.6512	Remote Similarity	NPC475691
0.6512	Remote Similarity	NPC318067
0.6512	Remote Similarity	NPC328107
0.6509	Remote Similarity	NPC267704
0.6508	Remote Similarity	NPC204784
0.6504	Remote Similarity	NPC274839
0.6504	Remote Similarity	NPC476357
0.65	Remote Similarity	NPC216122
0.6495	Remote Similarity	NPC311343
0.6491	Remote Similarity	NPC229242
0.6491	Remote Similarity	NPC145052
0.6476	Remote Similarity	NPC230068
0.6471	Remote Similarity	NPC298023
0.6471	Remote Similarity	NPC179726
0.6471	Remote Similarity	NPC329318
0.6466	Remote Similarity	NPC320891
0.6466	Remote Similarity	NPC304873
0.646	Remote Similarity	NPC12695
0.6457	Remote Similarity	NPC988
0.6457	Remote Similarity	NPC289432
0.6457	Remote Similarity	NPC105709
0.6452	Remote Similarity	NPC260886
0.6452	Remote Similarity	NPC226093
0.6449	Remote Similarity	NPC123476
0.6441	Remote Similarity	NPC105899
0.6441	Remote Similarity	NPC209632
0.6441	Remote Similarity	NPC471186
0.6435	Remote Similarity	NPC221825
0.6435	Remote Similarity	NPC217621
0.6434	Remote Similarity	NPC475692
0.6429	Remote Similarity	NPC246757
0.6429	Remote Similarity	NPC291070
0.6422	Remote Similarity	NPC477693
0.6422	Remote Similarity	NPC477704
0.641	Remote Similarity	NPC255676

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 NPC474910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1106
0.2-0.3	1840
0.3-0.4	3536
0.4-0.5	1813
0.5-0.6	384
0.6-0.7	75
0.7-0.8	7
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD650	Approved
0.82	Intermediate Similarity	NPD7609	Phase 3
0.8119	Intermediate Similarity	NPD7631	Approved
0.7981	Intermediate Similarity	NPD3495	Discontinued
0.7429	Intermediate Similarity	NPD1508	Approved
0.7374	Intermediate Similarity	NPD942	Approved
0.7355	Intermediate Similarity	NPD4879	Approved
0.7222	Intermediate Similarity	NPD1843	Approved
0.7155	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4878	Approved
0.6931	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1932	Approved
0.6842	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1929	Approved
0.6842	Remote Similarity	NPD1930	Approved
0.6792	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1074	Approved
0.6777	Remote Similarity	NPD1073	Approved
0.6777	Remote Similarity	NPD1075	Approved
0.6731	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2066	Phase 3
0.6695	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2648	Phase 3
0.6609	Remote Similarity	NPD2193	Phase 2
0.6577	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1022	Approved
0.6504	Remote Similarity	NPD1021	Approved
0.6504	Remote Similarity	NPD5951	Approved
0.6504	Remote Similarity	NPD1023	Approved
0.6504	Remote Similarity	NPD1020	Approved
0.6481	Remote Similarity	NPD1087	Approved
0.6466	Remote Similarity	NPD2196	Discontinued
0.6434	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7009	Phase 2
0.6418	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD1693	Approved
0.6372	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD664	Approved
0.6364	Remote Similarity	NPD1317	Discontinued
0.6356	Remote Similarity	NPD164	Approved
0.6349	Remote Similarity	NPD7610	Discontinued
0.6328	Remote Similarity	NPD4164	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5836	Discontinued
0.6328	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1086	Approved
0.6306	Remote Similarity	NPD1090	Approved
0.6306	Remote Similarity	NPD1089	Approved
0.6303	Remote Similarity	NPD1677	Discontinued
0.6303	Remote Similarity	NPD2197	Approved
0.6303	Remote Similarity	NPD2192	Approved
0.6293	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5653	Discontinued
0.6283	Remote Similarity	NPD1563	Approved
0.6279	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1100	Approved
0.6261	Remote Similarity	NPD1099	Approved
0.625	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1239	Approved
0.6239	Remote Similarity	NPD1616	Discontinued
0.6228	Remote Similarity	NPD6049	Phase 2
0.6228	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1237	Approved
0.6216	Remote Similarity	NPD800	Approved
0.6195	Remote Similarity	NPD1088	Approved
0.6186	Remote Similarity	NPD2171	Approved
0.6179	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1989	Approved
0.6172	Remote Similarity	NPD2617	Discontinued
0.6154	Remote Similarity	NPD1889	Phase 1
0.6154	Remote Similarity	NPD1302	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD2182	Approved
0.614	Remote Similarity	NPD1202	Approved
0.6134	Remote Similarity	NPD3357	Discontinued
0.6132	Remote Similarity	NPD914	Suspended
0.6121	Remote Similarity	NPD1566	Phase 3
0.6121	Remote Similarity	NPD1565	Approved
0.6121	Remote Similarity	NPD1564	Approved
0.6111	Remote Similarity	NPD1185	Approved
0.6111	Remote Similarity	NPD3971	Phase 1
0.6103	Remote Similarity	NPD2754	Discontinued
0.6095	Remote Similarity	NPD225	Approved
0.6095	Remote Similarity	NPD227	Approved
0.6091	Remote Similarity	NPD9259	Approved
0.6091	Remote Similarity	NPD9257	Approved
0.6087	Remote Similarity	NPD4094	Approved
0.6083	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7094	Approved
0.608	Remote Similarity	NPD6858	Approved
0.605	Remote Similarity	NPD813	Approved
0.6038	Remote Similarity	NPD1475	Approved
0.6038	Remote Similarity	NPD9490	Approved
0.6016	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4657	Approved
0.5983	Remote Similarity	NPD4655	Approved
0.5971	Remote Similarity	NPD4452	Approved
0.5971	Remote Similarity	NPD4453	Approved
0.597	Remote Similarity	NPD1888	Phase 1
0.5969	Remote Similarity	NPD997	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD9491	Approved
0.5954	Remote Similarity	NPD2345	Approved
0.5938	Remote Similarity	NPD3317	Approved
0.5926	Remote Similarity	NPD226	Approved
0.5926	Remote Similarity	NPD1470	Approved
0.592	Remote Similarity	NPD189	Phase 3
0.592	Remote Similarity	NPD188	Approved
0.5917	Remote Similarity	NPD5753	Discontinued
0.5909	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD182	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1238	Approved
0.5878	Remote Similarity	NPD1245	Approved
0.5877	Remote Similarity	NPD9256	Approved
0.5877	Remote Similarity	NPD3672	Approved
0.5877	Remote Similarity	NPD9258	Approved
0.5877	Remote Similarity	NPD3673	Approved
0.587	Remote Similarity	NPD7008	Discontinued
0.587	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1201	Approved
0.5857	Remote Similarity	NPD1588	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD1876	Approved
0.5852	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD4874	Phase 2
0.5833	Remote Similarity	NPD7611	Approved
0.5821	Remote Similarity	NPD3972	Approved
0.582	Remote Similarity	NPD5909	Discontinued
0.5816	Remote Similarity	NPD2863	Approved
0.581	Remote Similarity	NPD9716	Approved
0.5809	Remote Similarity	NPD3245	Phase 3
0.5809	Remote Similarity	NPD3244	Pre-registration
0.5798	Remote Similarity	NPD466	Approved
0.5797	Remote Similarity	NPD3063	Discontinued
0.5789	Remote Similarity	NPD5347	Phase 2
0.5789	Remote Similarity	NPD5346	Phase 2
0.5786	Remote Similarity	NPD7961	Discontinued
0.5786	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6027	Approved
0.5785	Remote Similarity	NPD6024	Approved
0.5781	Remote Similarity	NPD7077	Approved
0.5781	Remote Similarity	NPD7076	Approved
0.5758	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD1651	Approved
0.5752	Remote Similarity	NPD4793	Discontinued
0.575	Remote Similarity	NPD742	Approved
0.5746	Remote Similarity	NPD6287	Discontinued
0.5736	Remote Similarity	NPD2508	Discontinued
0.5736	Remote Similarity	NPD1246	Approved
0.5734	Remote Similarity	NPD3934	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD4449	Approved
0.5734	Remote Similarity	NPD2830	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD4448	Approved
0.5724	Remote Similarity	NPD2353	Approved
0.5724	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7949	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.569	Remote Similarity	NPD1007	Discontinued
0.5678	Remote Similarity	NPD9260	Approved
0.5676	Remote Similarity	NPD262	Approved
0.5676	Remote Similarity	NPD6485	Discontinued
0.5676	Remote Similarity	NPD7575	Phase 3
0.5676	Remote Similarity	NPD263	Approved
0.5664	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD1241	Discontinued
0.5658	Remote Similarity	NPD957	Approved
0.5646	Remote Similarity	NPD5009	Approved
0.5646	Remote Similarity	NPD5010	Approved
0.5643	Remote Similarity	NPD5246	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.563	Remote Similarity	NPD1281	Approved
0.562	Remote Similarity	NPD2056	Discontinued
0.562	Remote Similarity	NPD524	Approved
0.562	Remote Similarity	NPD523	Approved
0.562	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD2346	Discontinued
0.5616	Remote Similarity	NPD3935	Phase 3
0.5615	Remote Similarity	NPD2319	Discontinued
0.5615	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD1050	Approved
0.561	Remote Similarity	NPD9500	Approved
0.561	Remote Similarity	NPD6647	Phase 2
0.56	Remote Similarity	NPD675	Discontinued

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