NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.14
Volume:	259.928
LogP:	1.49
LogD:	1.456
LogS:	-2.328
# Rotatable Bonds:	0
TPSA:	58.88
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	4.941
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.41
MDCK Permeability:	1.6432548363809474e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.243
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	86.89061737060547%
Volume Distribution (VD):	1.731
Pgp-substrate:	13.032756805419922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.669
CYP2C19-inhibitor:	0.386
CYP2C19-substrate:	0.335
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.469
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	5.931
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.591
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.29
Carcinogencity:	0.646
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC47298

Natural Product ID:	NPC47298
*Common Name:**	ZRJBHWIHUMBLCN-YQEJDHNASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZRJBHWIHUMBLCN-YQEJDHNASA-N
Standard InCHI:	InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
SMILES:	C/C=C/1[C@H]2C=C(C)C[C@@]1(c1ccc(nc1C2)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL395280
PubChem CID:	854026
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones 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
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141864]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO40458	Aspergillus versicolor Y10	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26618211]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30183289]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30701972]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32941036]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6403	Phlegmariurus squarrosus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	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
AC50	2
IC50	18
Ki	2
LD50	2
Others	18
Potency	1

Activity Type	# Activity
Individual Protein	14
ORGANISM	8
Others	19
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	600.0	nM	PMID[488948]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	82.0	nM	PMID[488950]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	120.0	nM	PMID[488951]
NPT2748	Individual Protein	Butyrylcholinesterase	Rattus norvegicus	IC50	=	36400.0	nM	PMID[488951]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	98.0	nM	PMID[488952]
NPT2748	Individual Protein	Butyrylcholinesterase	Rattus norvegicus	IC50	=	36400.0	nM	PMID[488952]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	400.0	nM	PMID[488953]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[488955]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	33.0	nM	PMID[488955]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	4300.0	nM	PMID[488956]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	5170.0	nM	PMID[488959]
NPT2748	Individual Protein	Butyrylcholinesterase	Rattus norvegicus	IC50	=	74430.0	nM	PMID[488961]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	82.0	nM	PMID[488961]
NPT2	Others	Unspecified		AC50	n.a.	11220.2	nM	PMID[488947]
NPT2	Others	Unspecified		Ac50	n.a.	11.22	uM	PMID[488947]
NPT2	Others	Unspecified		Ac50	n.a.	44.67	uM	PMID[488947]
NPT2	Others	Unspecified		AC50	n.a.	44668.4	nM	PMID[488947]
NPT2	Others	Unspecified		IC50	=	36400.0	nM	PMID[488950]
NPT2	Others	Unspecified		Ratio IC50	=	444.0	n.a.	PMID[488950]
NPT2	Others	Unspecified		Ratio IC50	>	371.0	n.a.	PMID[488952]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-5.72	%	PMID[488954]
NPT2	Others	Unspecified		Ratio IC50	>	15.1	n.a.	PMID[488955]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.2718	%	PMID[488957]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.1	%	PMID[488958]
NPT25979	SINGLE PROTEIN	Cholinesterase	Canis lupus familiaris	IC50	>	10000000.0	nM	PMID[488959]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[488960]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[488960]
NPT27	Others	Unspecified		LD50	>	4.0	mg.kg-1	PMID[488961]
NPT27	Others	Unspecified		LD50	=	2.0	mg.kg-1	PMID[488961]
NPT2	Others	Unspecified		Activity	=	85.0	%	PMID[488961]
NPT2	Others	Unspecified		Ki	=	9500.0	nM	PMID[488961]
NPT2	Others	Unspecified		Ki	=	5600.0	nM	PMID[488961]
NPT2	Others	Unspecified		Activity	=	505.0	nM	PMID[488961]
NPT2	Others	Unspecified		Activity	=	668.0	nM	PMID[488961]
NPT2	Others	Unspecified		Activity	=	30.0	%	PMID[488961]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ratio	=	2.0	n.a.	PMID[488961]
NPT2	Others	Unspecified		Inhibition	=	21.0	%	PMID[488961]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ratio	=	140.0	n.a.	PMID[488961]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ratio	=	15.0	n.a.	PMID[488961]
NPT2	Others	Unspecified		Inhibition	=	16.0	%	PMID[488961]
NPT914	Individual Protein	Acetylcholinesterase	Bos taurus	IC50	=	100.0	nM	PMID[488962]
NPT2	Others	Unspecified		Potency	n.a.	29849.3	nM	PubChem BioAssay data set

☑ 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 NPC47298 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	459
0.1-0.2	2961
0.2-0.3	12718
0.3-0.4	11939
0.4-0.5	9549
0.5-0.6	3606
0.6-0.7	1333
0.7-0.8	112
0.8-0.85	2
0.85-0.9	6
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC315214
0.9933	High Similarity	NPC32028
0.98	High Similarity	NPC159319
0.9548	High Similarity	NPC259545
0.9545	High Similarity	NPC126481
0.9308	High Similarity	NPC232340
0.9177	High Similarity	NPC471294
0.8788	High Similarity	NPC133306
0.8655	High Similarity	NPC45850
0.8529	High Similarity	NPC183805
0.8366	Intermediate Similarity	NPC60553
0.8038	Intermediate Similarity	NPC161292
0.8037	Intermediate Similarity	NPC84508
0.7892	Intermediate Similarity	NPC473057
0.784	Intermediate Similarity	NPC153769
0.7834	Intermediate Similarity	NPC245657
0.7797	Intermediate Similarity	NPC128751
0.7771	Intermediate Similarity	NPC280853
0.7753	Intermediate Similarity	NPC469497
0.7753	Intermediate Similarity	NPC106833
0.7746	Intermediate Similarity	NPC88363
0.7746	Intermediate Similarity	NPC72980
0.7722	Intermediate Similarity	NPC285016
0.7707	Intermediate Similarity	NPC471596
0.7697	Intermediate Similarity	NPC246700
0.764	Intermediate Similarity	NPC206186
0.7627	Intermediate Similarity	NPC94943
0.7616	Intermediate Similarity	NPC474409
0.7614	Intermediate Similarity	NPC212535
0.7595	Intermediate Similarity	NPC471594
0.7578	Intermediate Similarity	NPC471598
0.7574	Intermediate Similarity	NPC97367
0.7571	Intermediate Similarity	NPC190007
0.7544	Intermediate Similarity	NPC44161
0.7529	Intermediate Similarity	NPC471178
0.7529	Intermediate Similarity	NPC288943
0.7516	Intermediate Similarity	NPC278451
0.7515	Intermediate Similarity	NPC471177
0.7515	Intermediate Similarity	NPC59779
0.7515	Intermediate Similarity	NPC124542
0.75	Intermediate Similarity	NPC288445
0.75	Intermediate Similarity	NPC478032
0.7486	Intermediate Similarity	NPC283152
0.7485	Intermediate Similarity	NPC141353
0.7473	Intermediate Similarity	NPC249040
0.7471	Intermediate Similarity	NPC303225
0.747	Intermediate Similarity	NPC26872
0.7457	Intermediate Similarity	NPC476686
0.7457	Intermediate Similarity	NPC476688
0.7457	Intermediate Similarity	NPC105758
0.743	Intermediate Similarity	NPC476319
0.7405	Intermediate Similarity	NPC153042
0.7405	Intermediate Similarity	NPC474188
0.7389	Intermediate Similarity	NPC171171
0.7377	Intermediate Similarity	NPC280964
0.7377	Intermediate Similarity	NPC114335
0.7377	Intermediate Similarity	NPC141915
0.7374	Intermediate Similarity	NPC204717
0.7374	Intermediate Similarity	NPC320394
0.7348	Intermediate Similarity	NPC66083
0.7341	Intermediate Similarity	NPC278874
0.7337	Intermediate Similarity	NPC26850
0.7333	Intermediate Similarity	NPC314002
0.7318	Intermediate Similarity	NPC220765
0.7318	Intermediate Similarity	NPC19679
0.7316	Intermediate Similarity	NPC475070
0.7314	Intermediate Similarity	NPC208060
0.7301	Intermediate Similarity	NPC470394
0.7301	Intermediate Similarity	NPC470404
0.7301	Intermediate Similarity	NPC470403
0.7293	Intermediate Similarity	NPC194040
0.7293	Intermediate Similarity	NPC314573
0.7292	Intermediate Similarity	NPC477111
0.7283	Intermediate Similarity	NPC108469
0.7278	Intermediate Similarity	NPC62069
0.7268	Intermediate Similarity	NPC3715
0.7263	Intermediate Similarity	NPC223427
0.7257	Intermediate Similarity	NPC158129
0.7253	Intermediate Similarity	NPC46580
0.7243	Intermediate Similarity	NPC329541
0.7238	Intermediate Similarity	NPC42591
0.7219	Intermediate Similarity	NPC70956
0.7219	Intermediate Similarity	NPC243834
0.7212	Intermediate Similarity	NPC470395
0.7209	Intermediate Similarity	NPC177404
0.7209	Intermediate Similarity	NPC224632
0.7202	Intermediate Similarity	NPC475910
0.7202	Intermediate Similarity	NPC470931
0.72	Intermediate Similarity	NPC473764
0.72	Intermediate Similarity	NPC314940
0.7196	Intermediate Similarity	NPC329747
0.7196	Intermediate Similarity	NPC329793
0.7189	Intermediate Similarity	NPC324149
0.7189	Intermediate Similarity	NPC99666
0.7188	Intermediate Similarity	NPC477113
0.7184	Intermediate Similarity	NPC98187
0.7167	Intermediate Similarity	NPC144114
0.7165	Intermediate Similarity	NPC476116
0.7158	Intermediate Similarity	NPC254762
0.7143	Intermediate Similarity	NPC476167
0.7143	Intermediate Similarity	NPC317430
0.7143	Intermediate Similarity	NPC154293
0.7127	Intermediate Similarity	NPC176127
0.7126	Intermediate Similarity	NPC257142
0.7121	Intermediate Similarity	NPC469928
0.7121	Intermediate Similarity	NPC330009
0.7121	Intermediate Similarity	NPC183407
0.712	Intermediate Similarity	NPC475112
0.712	Intermediate Similarity	NPC291535
0.712	Intermediate Similarity	NPC475085
0.712	Intermediate Similarity	NPC32771
0.7112	Intermediate Similarity	NPC276517
0.7107	Intermediate Similarity	NPC478074
0.7104	Intermediate Similarity	NPC61350
0.7095	Intermediate Similarity	NPC184964
0.709	Intermediate Similarity	NPC192315
0.709	Intermediate Similarity	NPC306376
0.7088	Intermediate Similarity	NPC84478
0.7083	Intermediate Similarity	NPC476098
0.7081	Intermediate Similarity	NPC95783
0.7079	Intermediate Similarity	NPC189812
0.7079	Intermediate Similarity	NPC312872
0.7079	Intermediate Similarity	NPC329688
0.7076	Intermediate Similarity	NPC285469
0.7074	Intermediate Similarity	NPC205403
0.7072	Intermediate Similarity	NPC477891
0.7072	Intermediate Similarity	NPC314394
0.7069	Intermediate Similarity	NPC118511
0.7062	Intermediate Similarity	NPC193777
0.7059	Intermediate Similarity	NPC36168
0.7056	Intermediate Similarity	NPC67659
0.7052	Intermediate Similarity	NPC131718
0.7043	Intermediate Similarity	NPC469390
0.7039	Intermediate Similarity	NPC150048
0.7039	Intermediate Similarity	NPC203754
0.7039	Intermediate Similarity	NPC134586
0.7037	Intermediate Similarity	NPC77555
0.7026	Intermediate Similarity	NPC18348
0.7022	Intermediate Similarity	NPC313791
0.7022	Intermediate Similarity	NPC472123
0.7022	Intermediate Similarity	NPC34508
0.7011	Intermediate Similarity	NPC16667
0.701	Intermediate Similarity	NPC475841
0.701	Intermediate Similarity	NPC474145
0.7006	Intermediate Similarity	NPC164664
0.7006	Intermediate Similarity	NPC280548
0.7	Intermediate Similarity	NPC284348
0.7	Intermediate Similarity	NPC211997
0.7	Intermediate Similarity	NPC96890
0.6984	Remote Similarity	NPC242209
0.6984	Remote Similarity	NPC472193
0.6979	Remote Similarity	NPC267423
0.6971	Remote Similarity	NPC476118
0.697	Remote Similarity	NPC294620
0.697	Remote Similarity	NPC48353
0.6968	Remote Similarity	NPC289786
0.6963	Remote Similarity	NPC476175
0.6963	Remote Similarity	NPC128823
0.6963	Remote Similarity	NPC280714
0.6959	Remote Similarity	NPC137929
0.6959	Remote Similarity	NPC164374
0.6954	Remote Similarity	NPC5145
0.695	Remote Similarity	NPC477110
0.6947	Remote Similarity	NPC156704
0.6946	Remote Similarity	NPC242556
0.6936	Remote Similarity	NPC116573
0.6935	Remote Similarity	NPC242928
0.6931	Remote Similarity	NPC195314
0.6927	Remote Similarity	NPC11017
0.6923	Remote Similarity	NPC304183
0.6923	Remote Similarity	NPC198339
0.6919	Remote Similarity	NPC9894
0.6919	Remote Similarity	NPC208284
0.6919	Remote Similarity	NPC220337
0.6919	Remote Similarity	NPC207726
0.6915	Remote Similarity	NPC476041
0.6915	Remote Similarity	NPC304926
0.6912	Remote Similarity	NPC162748
0.6907	Remote Similarity	NPC477135
0.6906	Remote Similarity	NPC151939
0.6895	Remote Similarity	NPC70259
0.6888	Remote Similarity	NPC53344
0.6888	Remote Similarity	NPC270918
0.6882	Remote Similarity	NPC37548
0.6882	Remote Similarity	NPC124005
0.6879	Remote Similarity	NPC184476
0.6878	Remote Similarity	NPC307963
0.6875	Remote Similarity	NPC32200
0.6875	Remote Similarity	NPC102423
0.6872	Remote Similarity	NPC252590
0.6872	Remote Similarity	NPC470500
0.6869	Remote Similarity	NPC309845
0.6869	Remote Similarity	NPC471304
0.6868	Remote Similarity	NPC472443
0.6868	Remote Similarity	NPC472168
0.6868	Remote Similarity	NPC270009
0.6863	Remote Similarity	NPC81561
0.686	Remote Similarity	NPC6215
0.6859	Remote Similarity	NPC473814
0.6859	Remote Similarity	NPC78767

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 NPC47298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	641
0.2-0.3	857
0.3-0.4	1166
0.4-0.5	3092
0.5-0.6	2496
0.6-0.7	558
0.7-0.8	58
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1684	Approved
1.0	High Similarity	NPD1685	Approved
0.8362	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD925	Approved
0.7738	Intermediate Similarity	NPD926	Approved
0.773	Intermediate Similarity	NPD6158	Phase 2
0.773	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2882	Phase 1
0.7609	Intermediate Similarity	NPD2177	Approved
0.7609	Intermediate Similarity	NPD2176	Approved
0.7609	Intermediate Similarity	NPD2175	Phase 3
0.7602	Intermediate Similarity	NPD1326	Approved
0.7602	Intermediate Similarity	NPD1325	Approved
0.7586	Intermediate Similarity	NPD6159	Phase 2
0.7542	Intermediate Similarity	NPD2383	Phase 1
0.7516	Intermediate Similarity	NPD3525	Discontinued
0.7485	Intermediate Similarity	NPD425	Approved
0.7485	Intermediate Similarity	NPD424	Approved
0.7474	Intermediate Similarity	NPD2916	Discontinued
0.7458	Intermediate Similarity	NPD4204	Approved
0.7458	Intermediate Similarity	NPD4203	Approved
0.7457	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5936	Approved
0.7448	Intermediate Similarity	NPD5939	Approved
0.7443	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD862	Approved
0.7368	Intermediate Similarity	NPD863	Approved
0.7368	Intermediate Similarity	NPD861	Approved
0.7346	Intermediate Similarity	NPD1592	Phase 3
0.734	Intermediate Similarity	NPD4511	Phase 1
0.7333	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2381	Approved
0.733	Intermediate Similarity	NPD2380	Approved
0.733	Intermediate Similarity	NPD5100	Phase 3
0.733	Intermediate Similarity	NPD2382	Approved
0.7299	Intermediate Similarity	NPD7474	Suspended
0.7294	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5255	Approved
0.7273	Intermediate Similarity	NPD6492	Phase 2
0.7273	Intermediate Similarity	NPD5065	Approved
0.7247	Intermediate Similarity	NPD3920	Phase 2
0.7243	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2781	Approved
0.724	Intermediate Similarity	NPD6290	Phase 2
0.7235	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4702	Approved
0.7229	Intermediate Similarity	NPD4703	Approved
0.7225	Intermediate Similarity	NPD2780	Approved
0.7225	Intermediate Similarity	NPD2782	Approved
0.7216	Intermediate Similarity	NPD7418	Discontinued
0.7182	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4502	Phase 2
0.7173	Intermediate Similarity	NPD4044	Discontinued
0.7168	Intermediate Similarity	NPD444	Approved
0.7152	Intermediate Similarity	NPD3813	Approved
0.7151	Intermediate Similarity	NPD3417	Phase 1
0.7143	Intermediate Similarity	NPD2762	Phase 2
0.7143	Intermediate Similarity	NPD8396	Approved
0.7143	Intermediate Similarity	NPD8395	Approved
0.7128	Intermediate Similarity	NPD7948	Phase 1
0.7113	Intermediate Similarity	NPD6376	Discontinued
0.709	Intermediate Similarity	NPD2727	Phase 2
0.7086	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3814	Phase 1
0.7045	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3931	Approved
0.7031	Intermediate Similarity	NPD3928	Approved
0.7029	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6590	Discontinued
0.7018	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3404	Approved
0.7	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3717	Discontinued
0.6983	Remote Similarity	NPD9690	Approved
0.6971	Remote Similarity	NPD5138	Approved
0.6971	Remote Similarity	NPD5140	Approved
0.6966	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9705	Discontinued
0.6954	Remote Similarity	NPD112	Approved
0.6949	Remote Similarity	NPD2844	Phase 3
0.6943	Remote Similarity	NPD6975	Discontinued
0.6939	Remote Similarity	NPD7671	Approved
0.6939	Remote Similarity	NPD7672	Approved
0.6927	Remote Similarity	NPD3224	Phase 2
0.6923	Remote Similarity	NPD5530	Phase 1
0.6918	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD972	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6991	Approved
0.6898	Remote Similarity	NPD6281	Approved
0.6888	Remote Similarity	NPD7222	Phase 2
0.6885	Remote Similarity	NPD7867	Phase 1
0.6884	Remote Similarity	NPD3330	Phase 1
0.6879	Remote Similarity	NPD6026	Approved
0.6878	Remote Similarity	NPD1038	Approved
0.6875	Remote Similarity	NPD947	Approved
0.6868	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6227	Discontinued
0.6865	Remote Similarity	NPD4889	Approved
0.6857	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3243	Approved
0.6848	Remote Similarity	NPD5596	Phase 2
0.6848	Remote Similarity	NPD852	Discontinued
0.6842	Remote Similarity	NPD6251	Discontinued
0.6842	Remote Similarity	NPD4462	Approved
0.6842	Remote Similarity	NPD4463	Approved
0.6839	Remote Similarity	NPD2582	Approved
0.6839	Remote Similarity	NPD2581	Approved
0.6834	Remote Similarity	NPD6220	Phase 3
0.6828	Remote Similarity	NPD5256	Discontinued
0.6826	Remote Similarity	NPD5020	Approved
0.6825	Remote Similarity	NPD3923	Approved
0.6825	Remote Similarity	NPD6569	Phase 2
0.6825	Remote Similarity	NPD3922	Approved
0.6825	Remote Similarity	NPD3924	Approved
0.6825	Remote Similarity	NPD3921	Approved
0.6806	Remote Similarity	NPD6594	Discontinued
0.6806	Remote Similarity	NPD5512	Phase 3
0.6805	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5429	Discontinued
0.68	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1251	Discontinued
0.6789	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6361	Phase 2
0.6789	Remote Similarity	NPD802	Phase 2
0.6789	Remote Similarity	NPD9695	Approved
0.6786	Remote Similarity	NPD4795	Phase 2
0.6786	Remote Similarity	NPD4038	Approved
0.6786	Remote Similarity	NPD4035	Approved
0.6786	Remote Similarity	NPD4034	Approved
0.6786	Remote Similarity	NPD4033	Approved
0.6786	Remote Similarity	NPD31	Approved
0.6786	Remote Similarity	NPD32	Approved
0.6786	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4037	Approved
0.6786	Remote Similarity	NPD4122	Approved
0.6786	Remote Similarity	NPD4039	Approved
0.6786	Remote Similarity	NPD4036	Approved
0.6782	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7726	Phase 1
0.6774	Remote Similarity	NPD3082	Discontinued
0.6772	Remote Similarity	NPD5913	Phase 3
0.6772	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2616	Phase 3
0.6766	Remote Similarity	NPD2615	Phase 3
0.6765	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1739	Approved
0.6753	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1740	Approved
0.6753	Remote Similarity	NPD484	Approved
0.6751	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9080	Approved
0.675	Remote Similarity	NPD995	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9284	Approved
0.6748	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4375	Approved
0.6736	Remote Similarity	NPD7419	Discontinued
0.6735	Remote Similarity	NPD4886	Phase 2
0.6727	Remote Similarity	NPD1256	Approved
0.6727	Remote Similarity	NPD1254	Approved
0.6727	Remote Similarity	NPD1253	Approved
0.6727	Remote Similarity	NPD1255	Approved
0.6719	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7453	Approved
0.6717	Remote Similarity	NPD7452	Approved
0.6716	Remote Similarity	NPD2794	Discontinued
0.6702	Remote Similarity	NPD4551	Phase 2
0.67	Remote Similarity	NPD7112	Discontinued
0.6698	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2789	Approved
0.6684	Remote Similarity	NPD2952	Discontinued
0.6684	Remote Similarity	NPD6208	Discontinued
0.6684	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5003	Discontinued
0.6683	Remote Similarity	NPD5658	Approved
0.6667	Remote Similarity	NPD7221	Approved
0.6667	Remote Similarity	NPD7219	Approved
0.6667	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7469	Discontinued
0.6667	Remote Similarity	NPD1649	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