NPASS Compound

Structure

CID49824 OpenBabel06191715382D 25 27 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	3.256
LogD:	2.496
LogS:	-3.957
# Rotatable Bonds:	4
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	2.3
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	2.5135230316664092e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	88.4203109741211%
Volume Distribution (VD):	0.821
Pgp-substrate:	13.691666603088379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.78
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.371
CYP2D6-substrate:	0.733
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	2.55
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.313
Carcinogencity:	0.071
Eye Corrosion:	0.004
Eye Irritation:	0.384
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC49824

Natural Product ID:	NPC49824
*Common Name:**	Mikanin
IUPAC Name:	3,5-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:	Mikanin
Standard InCHIKey:	SGCYGSKAUSOJND-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)17-16(21)14(19)13-11(25-17)8-12(23-2)18(24-3)15(13)20/h4-8,20-21H,1-3H3
SMILES:	COc1ccc(cc1)c1c(c(=O)c2c(cc(c(c2O)OC)OC)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554063
PubChem CID:	15560536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19267453]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23998	Auxarthron reticulatum	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24900275]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32941036]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24950	Eupatorium aschenbornianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23866	Anisocycla cymosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25313	Satureja douglasii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24242	Haminoea cymbalum	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25683	Columba livia	Species	Columbidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25115	Psychotria calocarpa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24142	Cereus ocamponis	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22408	Aconitum polyschistum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24662	Ulmus laevis	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24895	Parmelia springtonensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20331	Aerva tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23134	Artemisia kaschgarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23998	Auxarthron reticulatum	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1827	Morinda elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25341	Sanango racemosum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24854	Beltrania rhombica	Species	Beltraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25602	Crotalaria barbata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24950	Eupatorium aschenbornianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25399	Patrinia intermedia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25241	Cordyla africana	Species	Fabaceae	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
IC50	3
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	499.7	uM	PMID[463228]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	55500.0	nM	PMID[463228]
NPT27	Others	Unspecified		TC50	=	83.1	uM	PMID[463228]
NPT27	Others	Unspecified		TI	=	1.5	n.a.	PMID[463228]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	41600.0	nM	PMID[463228]
NPT27	Others	Unspecified		TI	=	2.0	n.a.	PMID[463228]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	166600.0	nM	PMID[463228]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[463228]

☑ 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 NPC49824 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	474
0.1-0.2	2018
0.2-0.3	5215
0.3-0.4	11473
0.4-0.5	5640
0.5-0.6	3975
0.6-0.7	5130
0.7-0.8	4761
0.8-0.85	1948
0.85-0.9	1138
0.9-0.95	630
0.95-1	295

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC101830
0.9933	High Similarity	NPC189179
0.9933	High Similarity	NPC227192
0.9933	High Similarity	NPC110070
0.9933	High Similarity	NPC224137
0.9933	High Similarity	NPC93376
0.9933	High Similarity	NPC203891
0.9933	High Similarity	NPC75215
0.9932	High Similarity	NPC44079
0.9932	High Similarity	NPC26227
0.9932	High Similarity	NPC201451
0.9867	High Similarity	NPC261004
0.9867	High Similarity	NPC152166
0.9867	High Similarity	NPC115798
0.9867	High Similarity	NPC22472
0.9867	High Similarity	NPC4481
0.9867	High Similarity	NPC130894
0.9867	High Similarity	NPC300943
0.9867	High Similarity	NPC9609
0.9867	High Similarity	NPC191459
0.9867	High Similarity	NPC18772
0.9867	High Similarity	NPC288669
0.9867	High Similarity	NPC176300
0.9867	High Similarity	NPC253634
0.9867	High Similarity	NPC143828
0.9867	High Similarity	NPC7846
0.9867	High Similarity	NPC25495
0.9867	High Similarity	NPC204854
0.9867	High Similarity	NPC19687
0.9867	High Similarity	NPC105242
0.9867	High Similarity	NPC18607
0.9866	High Similarity	NPC43243
0.9866	High Similarity	NPC474520
0.9866	High Similarity	NPC247017
0.9866	High Similarity	NPC266960
0.9866	High Similarity	NPC292107
0.9866	High Similarity	NPC98661
0.9866	High Similarity	NPC245546
0.9865	High Similarity	NPC145379
0.9865	High Similarity	NPC69394
0.9865	High Similarity	NPC231018
0.9865	High Similarity	NPC183878
0.9865	High Similarity	NPC86485
0.9865	High Similarity	NPC47781
0.9865	High Similarity	NPC22519
0.9865	High Similarity	NPC176775
0.9865	High Similarity	NPC160951
0.9865	High Similarity	NPC274327
0.9865	High Similarity	NPC255350
0.98	High Similarity	NPC78302
0.98	High Similarity	NPC472438
0.98	High Similarity	NPC7973
0.98	High Similarity	NPC305663
0.98	High Similarity	NPC287979
0.98	High Similarity	NPC29841
0.98	High Similarity	NPC163524
0.98	High Similarity	NPC235215
0.98	High Similarity	NPC176665
0.9799	High Similarity	NPC138360
0.9799	High Similarity	NPC280339
0.9799	High Similarity	NPC128863
0.9799	High Similarity	NPC146165
0.9799	High Similarity	NPC189960
0.9799	High Similarity	NPC92659
0.9799	High Similarity	NPC213622
0.9799	High Similarity	NPC256612
0.9799	High Similarity	NPC20830
0.9799	High Similarity	NPC183597
0.9799	High Similarity	NPC227325
0.9799	High Similarity	NPC32557
0.9799	High Similarity	NPC201136
0.9799	High Similarity	NPC196439
0.9799	High Similarity	NPC50715
0.9799	High Similarity	NPC4455
0.9799	High Similarity	NPC167815
0.9799	High Similarity	NPC163780
0.9799	High Similarity	NPC2476
0.9797	High Similarity	NPC131624
0.9797	High Similarity	NPC275836
0.9797	High Similarity	NPC275722
0.9797	High Similarity	NPC241498
0.9797	High Similarity	NPC198826
0.9797	High Similarity	NPC162313
0.9797	High Similarity	NPC212678
0.9797	High Similarity	NPC83508
0.9797	High Similarity	NPC120163
0.9797	High Similarity	NPC25270
0.9797	High Similarity	NPC57030
0.9797	High Similarity	NPC256283
0.9797	High Similarity	NPC239128
0.9797	High Similarity	NPC222830
0.9797	High Similarity	NPC187498
0.9797	High Similarity	NPC71334
0.9797	High Similarity	NPC156222
0.9797	High Similarity	NPC293183
0.9797	High Similarity	NPC188203
0.9797	High Similarity	NPC301323
0.9797	High Similarity	NPC100887
0.9797	High Similarity	NPC301123
0.9735	High Similarity	NPC193842
0.9733	High Similarity	NPC268161
0.9733	High Similarity	NPC265511
0.9733	High Similarity	NPC55619
0.9733	High Similarity	NPC178854
0.9733	High Similarity	NPC100916
0.9733	High Similarity	NPC200388
0.9732	High Similarity	NPC276409
0.9732	High Similarity	NPC78326
0.9732	High Similarity	NPC250822
0.9732	High Similarity	NPC179126
0.9732	High Similarity	NPC270620
0.9732	High Similarity	NPC75279
0.9732	High Similarity	NPC236223
0.973	High Similarity	NPC225731
0.973	High Similarity	NPC252933
0.973	High Similarity	NPC208043
0.973	High Similarity	NPC125062
0.973	High Similarity	NPC200740
0.973	High Similarity	NPC54394
0.973	High Similarity	NPC226973
0.9671	High Similarity	NPC246478
0.9669	High Similarity	NPC470402
0.9667	High Similarity	NPC214138
0.9667	High Similarity	NPC208197
0.9664	High Similarity	NPC39732
0.9664	High Similarity	NPC27208
0.9664	High Similarity	NPC134677
0.9664	High Similarity	NPC55205
0.9664	High Similarity	NPC82325
0.9664	High Similarity	NPC142540
0.9664	High Similarity	NPC60972
0.9664	High Similarity	NPC279989
0.9662	High Similarity	NPC50728
0.9662	High Similarity	NPC184136
0.9662	High Similarity	NPC166753
0.9662	High Similarity	NPC306821
0.9605	High Similarity	NPC195832
0.9605	High Similarity	NPC152904
0.9603	High Similarity	NPC472916
0.96	High Similarity	NPC246204
0.96	High Similarity	NPC162351
0.96	High Similarity	NPC58382
0.9597	High Similarity	NPC28274
0.9597	High Similarity	NPC50403
0.9597	High Similarity	NPC133953
0.9597	High Similarity	NPC236769
0.9597	High Similarity	NPC308451
0.9595	High Similarity	NPC48479
0.9595	High Similarity	NPC177298
0.9595	High Similarity	NPC137062
0.9595	High Similarity	NPC270465
0.9595	High Similarity	NPC159103
0.9595	High Similarity	NPC296197
0.9595	High Similarity	NPC87125
0.9595	High Similarity	NPC195351
0.9595	High Similarity	NPC17286
0.9595	High Similarity	NPC287101
0.9595	High Similarity	NPC259713
0.9595	High Similarity	NPC223579
0.9595	High Similarity	NPC216318
0.9595	High Similarity	NPC328119
0.9595	High Similarity	NPC183950
0.9595	High Similarity	NPC52005
0.9542	High Similarity	NPC263449
0.9542	High Similarity	NPC476980
0.9539	High Similarity	NPC222814
0.9539	High Similarity	NPC78225
0.9539	High Similarity	NPC96167
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC472913
0.9539	High Similarity	NPC245758
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC472914
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC472910
0.9539	High Similarity	NPC472911
0.9536	High Similarity	NPC2928
0.9533	High Similarity	NPC180234
0.9533	High Similarity	NPC120537
0.9533	High Similarity	NPC123886
0.9533	High Similarity	NPC199100
0.953	High Similarity	NPC149127
0.953	High Similarity	NPC286342
0.953	High Similarity	NPC45873
0.953	High Similarity	NPC219330
0.953	High Similarity	NPC188871
0.953	High Similarity	NPC77858
0.9527	High Similarity	NPC120464
0.9527	High Similarity	NPC195202
0.9527	High Similarity	NPC261548
0.9484	High Similarity	NPC470459
0.9481	High Similarity	NPC308992
0.9481	High Similarity	NPC258331
0.9474	High Similarity	NPC303255
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC255106

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 NPC49824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	995
0.2-0.3	1896
0.3-0.4	2684
0.4-0.5	1675
0.5-0.6	961
0.6-0.7	338
0.7-0.8	101
0.8-0.85	36
0.85-0.9	11
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9865	High Similarity	NPD2801	Approved
0.9392	High Similarity	NPD1512	Approved
0.9346	High Similarity	NPD3882	Suspended
0.9276	High Similarity	NPD1934	Approved
0.9257	High Similarity	NPD1511	Approved
0.9156	High Similarity	NPD3817	Phase 2
0.9091	High Similarity	NPD2393	Clinical (unspecified phase)
0.9057	High Similarity	NPD6166	Phase 2
0.9057	High Similarity	NPD6167	Clinical (unspecified phase)
0.9057	High Similarity	NPD6168	Clinical (unspecified phase)
0.9018	High Similarity	NPD4338	Clinical (unspecified phase)
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.8827	High Similarity	NPD3818	Discontinued
0.878	High Similarity	NPD6797	Phase 2
0.8773	High Similarity	NPD7054	Approved
0.8727	High Similarity	NPD7251	Discontinued
0.872	High Similarity	NPD7472	Approved
0.8675	High Similarity	NPD7808	Phase 3
0.8606	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD5494	Approved
0.8553	High Similarity	NPD5402	Approved
0.8506	High Similarity	NPD6799	Approved
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8405	Intermediate Similarity	NPD1247	Approved
0.8375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8289	Intermediate Similarity	NPD2796	Approved
0.8225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD943	Approved
0.82	Intermediate Similarity	NPD1240	Approved
0.8193	Intermediate Similarity	NPD3926	Phase 2
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8113	Intermediate Similarity	NPD5403	Approved
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD1607	Approved
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD919	Approved
0.8037	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5401	Approved
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7933	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7908	Intermediate Similarity	NPD447	Suspended
0.7867	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6959	Discontinued
0.7848	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7799	Intermediate Similarity	NPD6190	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.773	Intermediate Similarity	NPD1653	Approved
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7679	Intermediate Similarity	NPD3749	Approved
0.7661	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7632	Intermediate Similarity	NPD9494	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.7547	Intermediate Similarity	NPD2344	Approved
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD6099	Approved
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6651	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD1203	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7337	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7228	Approved
0.7226	Intermediate Similarity	NPD2798	Approved
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.7169	Intermediate Similarity	NPD4357	Discontinued
0.7161	Intermediate Similarity	NPD2797	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD2654	Approved
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD3225	Approved
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7048	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7044	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD2163	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7032	Intermediate Similarity	NPD2983	Phase 2
0.7032	Intermediate Similarity	NPD2982	Phase 2
0.703	Intermediate Similarity	NPD1652	Phase 2
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7015	Intermediate Similarity	NPD2899	Discontinued
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.6984	Remote Similarity	NPD4361	Phase 2
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7095	Approved
0.6981	Remote Similarity	NPD4625	Phase 3
0.6977	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7584	Approved
0.6968	Remote Similarity	NPD1481	Phase 2
0.6968	Remote Similarity	NPD2981	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