NPASS Compound

Structure

CID270883 OpenBabel06191716072D 24 26 0 0 0 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 -2.5981 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 -3.4641 -0.0000 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 1.7321 -0.0000 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 4.3301 3.5000 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 2.5981 1.5000 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 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 -0.0000 2.0000 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 0.8660 0.5000 0.0000 C 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 -0.0000 3.0000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 1 0 0 0 0 3 12 2 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.12
Volume:	340.24
LogP:	4.993
LogD:	3.211
LogS:	-3.41
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	2.485
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	1.4304565411293879e-05
Pgp-inhibitor:	0.111
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.75080108642578%
Volume Distribution (VD):	0.769
Pgp-substrate:	3.0070266723632812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.693
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	7.692
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.913
Carcinogencity:	0.175
Eye Corrosion:	0.003
Eye Irritation:	0.913
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC270883

Natural Product ID:	NPC270883
*Common Name:**	Licoflavanone A
IUPAC Name:	7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	HJGURBGBPIKRER-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-12(2)3-4-14-9-16-18(23)11-19(24-20(16)10-17(14)22)13-5-7-15(21)8-6-13/h3,5-11,21-22H,4H2,1-2H3
SMILES:	CC(=CCc1cc2c(=O)cc(c3ccc(cc3)O)oc2cc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506929
PubChem CID:	5319000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-prenylated flavones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO20984	Glycyrrhiza echinata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20984	Glycyrrhiza echinata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20984	Glycyrrhiza echinata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22336	Glycyrrhiza aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	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	1
Others	8

Activity Type	# Activity
Cell Line	4
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	54500.0	nM	PMID[480748]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	0.0	%	PMID[480750]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	30.0	%	PMID[480750]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	5.0	%	PMID[480750]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	11.0	%	PMID[480750]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	79.0	%	PMID[480750]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.05	n.a.	PMID[480751]
NPT2	Others	Unspecified		Inhibition	=	7.0	%	PMID[480750]
NPT2	Others	Unspecified		Inhibition	=	17.0	%	PMID[480750]

☑ 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 NPC270883 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	406
0.1-0.2	1792
0.2-0.3	4767
0.3-0.4	12092
0.4-0.5	5652
0.5-0.6	4366
0.6-0.7	5726
0.7-0.8	4156
0.8-0.85	1743
0.85-0.9	1363
0.9-0.95	553
0.95-1	81

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261227
1.0	High Similarity	NPC172986
0.9926	High Similarity	NPC156590
0.9926	High Similarity	NPC64908
0.9926	High Similarity	NPC118840
0.9926	High Similarity	NPC110969
0.9926	High Similarity	NPC205006
0.9926	High Similarity	NPC147688
0.9925	High Similarity	NPC220062
0.9925	High Similarity	NPC216978
0.9925	High Similarity	NPC55018
0.9925	High Similarity	NPC301217
0.9925	High Similarity	NPC303633
0.9925	High Similarity	NPC96565
0.9853	High Similarity	NPC11561
0.9853	High Similarity	NPC226636
0.9852	High Similarity	NPC159275
0.9852	High Similarity	NPC475680
0.9852	High Similarity	NPC69769
0.9852	High Similarity	NPC235239
0.9852	High Similarity	NPC241100
0.9852	High Similarity	NPC305355
0.9851	High Similarity	NPC201395
0.9781	High Similarity	NPC38219
0.9779	High Similarity	NPC103362
0.9779	High Similarity	NPC282300
0.9778	High Similarity	NPC217186
0.9778	High Similarity	NPC78913
0.9778	High Similarity	NPC18260
0.9778	High Similarity	NPC53181
0.971	High Similarity	NPC234629
0.971	High Similarity	NPC311741
0.9708	High Similarity	NPC62840
0.9708	High Similarity	NPC200694
0.9708	High Similarity	NPC299080
0.9708	High Similarity	NPC214236
0.9708	High Similarity	NPC59739
0.9708	High Similarity	NPC144499
0.9708	High Similarity	NPC293852
0.9708	High Similarity	NPC217083
0.9708	High Similarity	NPC78803
0.9706	High Similarity	NPC150522
0.9701	High Similarity	NPC13408
0.9638	High Similarity	NPC11700
0.9638	High Similarity	NPC293053
0.9638	High Similarity	NPC219915
0.9638	High Similarity	NPC149026
0.9638	High Similarity	NPC91560
0.9638	High Similarity	NPC257097
0.9638	High Similarity	NPC175504
0.9638	High Similarity	NPC143896
0.9638	High Similarity	NPC18585
0.9638	High Similarity	NPC68104
0.9638	High Similarity	NPC39329
0.9638	High Similarity	NPC150408
0.9638	High Similarity	NPC169591
0.9638	High Similarity	NPC166138
0.9638	High Similarity	NPC310130
0.9638	High Similarity	NPC75049
0.9638	High Similarity	NPC9117
0.9638	High Similarity	NPC106985
0.9638	High Similarity	NPC190637
0.9638	High Similarity	NPC164980
0.9638	High Similarity	NPC212932
0.9638	High Similarity	NPC221432
0.9638	High Similarity	NPC24821
0.9635	High Similarity	NPC3188
0.9635	High Similarity	NPC14871
0.963	High Similarity	NPC266597
0.963	High Similarity	NPC250266
0.963	High Similarity	NPC228661
0.9571	High Similarity	NPC79469
0.9571	High Similarity	NPC237635
0.9571	High Similarity	NPC23728
0.9571	High Similarity	NPC104406
0.9571	High Similarity	NPC24673
0.9571	High Similarity	NPC201731
0.9571	High Similarity	NPC110303
0.9571	High Similarity	NPC97716
0.9568	High Similarity	NPC326500
0.9568	High Similarity	NPC473015
0.9568	High Similarity	NPC236766
0.9568	High Similarity	NPC278175
0.9568	High Similarity	NPC319752
0.9568	High Similarity	NPC469953
0.9568	High Similarity	NPC197252
0.9568	High Similarity	NPC273538
0.9568	High Similarity	NPC209040
0.9568	High Similarity	NPC257236
0.9568	High Similarity	NPC216538
0.9568	High Similarity	NPC473013
0.9565	High Similarity	NPC148757
0.9565	High Similarity	NPC37496
0.9565	High Similarity	NPC125855
0.9565	High Similarity	NPC296917
0.9565	High Similarity	NPC1089
0.9565	High Similarity	NPC36181
0.9565	High Similarity	NPC265040
0.9565	High Similarity	NPC76338
0.9565	High Similarity	NPC306829
0.9565	High Similarity	NPC166934
0.9565	High Similarity	NPC182852
0.9565	High Similarity	NPC228504
0.9565	High Similarity	NPC32739
0.9565	High Similarity	NPC107572
0.9565	High Similarity	NPC227579
0.9565	High Similarity	NPC78
0.9565	High Similarity	NPC166482
0.9565	High Similarity	NPC223500
0.9565	High Similarity	NPC161506
0.9565	High Similarity	NPC177354
0.9565	High Similarity	NPC64915
0.9565	High Similarity	NPC328164
0.9565	High Similarity	NPC167624
0.9565	High Similarity	NPC324436
0.9565	High Similarity	NPC10937
0.9565	High Similarity	NPC473042
0.9565	High Similarity	NPC66515
0.9565	High Similarity	NPC324134
0.9565	High Similarity	NPC220998
0.9565	High Similarity	NPC194432
0.9565	High Similarity	NPC40833
0.9565	High Similarity	NPC76372
0.9562	High Similarity	NPC259166
0.9562	High Similarity	NPC219917
0.9562	High Similarity	NPC213659
0.9562	High Similarity	NPC144118
0.9562	High Similarity	NPC80962
0.9562	High Similarity	NPC48624
0.9562	High Similarity	NPC215311
0.9562	High Similarity	NPC204985
0.9562	High Similarity	NPC172250
0.9562	High Similarity	NPC326109
0.9559	High Similarity	NPC470668
0.9559	High Similarity	NPC124269
0.9559	High Similarity	NPC470669
0.9556	High Similarity	NPC98115
0.9556	High Similarity	NPC473887
0.9556	High Similarity	NPC29353
0.9556	High Similarity	NPC174999
0.9556	High Similarity	NPC186838
0.9556	High Similarity	NPC194281
0.9556	High Similarity	NPC477242
0.9556	High Similarity	NPC168105
0.9556	High Similarity	NPC127447
0.9556	High Similarity	NPC66349
0.9556	High Similarity	NPC124784
0.9556	High Similarity	NPC274109
0.9556	High Similarity	NPC477244
0.9556	High Similarity	NPC1486
0.9556	High Similarity	NPC477243
0.9556	High Similarity	NPC12165
0.9556	High Similarity	NPC150399
0.9556	High Similarity	NPC41461
0.9556	High Similarity	NPC25287
0.9556	High Similarity	NPC47815
0.9556	High Similarity	NPC231772
0.9556	High Similarity	NPC249606
0.9556	High Similarity	NPC234133
0.9552	High Similarity	NPC172262
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC160821
0.9504	High Similarity	NPC266572
0.9504	High Similarity	NPC6511
0.9504	High Similarity	NPC168085
0.95	High Similarity	NPC475052
0.95	High Similarity	NPC5820
0.95	High Similarity	NPC124729
0.95	High Similarity	NPC312973
0.95	High Similarity	NPC246948
0.95	High Similarity	NPC474161
0.95	High Similarity	NPC83357
0.95	High Similarity	NPC176229
0.95	High Similarity	NPC154217
0.95	High Similarity	NPC178343
0.95	High Similarity	NPC301276
0.95	High Similarity	NPC214774
0.95	High Similarity	NPC54577
0.95	High Similarity	NPC267375
0.95	High Similarity	NPC476088
0.95	High Similarity	NPC306488
0.95	High Similarity	NPC470647
0.95	High Similarity	NPC111786
0.95	High Similarity	NPC195621
0.95	High Similarity	NPC20488
0.95	High Similarity	NPC88964
0.95	High Similarity	NPC67805
0.95	High Similarity	NPC477955
0.95	High Similarity	NPC142405
0.9496	High Similarity	NPC196459
0.9496	High Similarity	NPC125894
0.9496	High Similarity	NPC85162
0.9496	High Similarity	NPC112791
0.9496	High Similarity	NPC278249
0.9496	High Similarity	NPC94794
0.9496	High Similarity	NPC107177
0.9496	High Similarity	NPC81697
0.9496	High Similarity	NPC188632
0.9496	High Similarity	NPC470296
0.9496	High Similarity	NPC87609

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 NPC270883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	994
0.2-0.3	1447
0.3-0.4	2720
0.4-0.5	1910
0.5-0.6	1154
0.6-0.7	352
0.7-0.8	118
0.8-0.85	36
0.85-0.9	26
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD7410	Clinical (unspecified phase)
0.9568	High Similarity	NPD4378	Clinical (unspecified phase)
0.9275	High Similarity	NPD1549	Phase 2
0.9203	High Similarity	NPD1550	Clinical (unspecified phase)
0.9203	High Similarity	NPD1552	Clinical (unspecified phase)
0.9197	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1240	Approved
0.913	High Similarity	NPD2796	Approved
0.9051	High Similarity	NPD1607	Approved
0.9041	High Similarity	NPD7411	Suspended
0.8973	High Similarity	NPD4380	Phase 2
0.8919	High Similarity	NPD2393	Clinical (unspecified phase)
0.8867	High Similarity	NPD7075	Discontinued
0.8859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8851	High Similarity	NPD6801	Discontinued
0.8819	High Similarity	NPD1511	Approved
0.8792	High Similarity	NPD7096	Clinical (unspecified phase)
0.8792	High Similarity	NPD7819	Suspended
0.8741	High Similarity	NPD3750	Approved
0.8699	High Similarity	NPD1512	Approved
0.869	High Similarity	NPD6799	Approved
0.8671	High Similarity	NPD7421	Clinical (unspecified phase)
0.8667	High Similarity	NPD2801	Approved
0.8618	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD7768	Phase 2
0.8542	High Similarity	NPD1243	Approved
0.8542	High Similarity	NPD2800	Approved
0.8526	High Similarity	NPD7852	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6599	Discontinued
0.8431	Intermediate Similarity	NPD3882	Suspended
0.8392	Intermediate Similarity	NPD3748	Approved
0.8392	Intermediate Similarity	NPD2799	Discontinued
0.838	Intermediate Similarity	NPD6651	Approved
0.8377	Intermediate Similarity	NPD3749	Approved
0.8365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD2313	Discontinued
0.8357	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8276	Intermediate Similarity	NPD2344	Approved
0.8267	Intermediate Similarity	NPD920	Approved
0.8267	Intermediate Similarity	NPD5403	Approved
0.8261	Intermediate Similarity	NPD1203	Approved
0.8247	Intermediate Similarity	NPD3817	Phase 2
0.8243	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.816	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD5953	Discontinued
0.8138	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7286	Phase 2
0.8133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5401	Approved
0.8108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD3268	Approved
0.8071	Intermediate Similarity	NPD2798	Approved
0.8054	Intermediate Similarity	NPD2309	Approved
0.805	Intermediate Similarity	NPD6232	Discontinued
0.8043	Intermediate Similarity	NPD9717	Approved
0.8039	Intermediate Similarity	NPD3226	Approved
0.8025	Intermediate Similarity	NPD7054	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD2797	Approved
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7986	Intermediate Similarity	NPD943	Approved
0.7975	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7972	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD422	Phase 1
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6100	Approved
0.7959	Intermediate Similarity	NPD6099	Approved
0.7958	Intermediate Similarity	NPD6832	Phase 2
0.7941	Intermediate Similarity	NPD1548	Phase 1
0.7927	Intermediate Similarity	NPD6797	Phase 2
0.7905	Intermediate Similarity	NPD2346	Discontinued
0.7898	Intermediate Similarity	NPD5402	Approved
0.7891	Intermediate Similarity	NPD4308	Phase 3
0.7891	Intermediate Similarity	NPD7033	Discontinued
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD919	Approved
0.7832	Intermediate Similarity	NPD4908	Phase 1
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7829	Intermediate Similarity	NPD7390	Discontinued
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.7801	Intermediate Similarity	NPD3225	Approved
0.7764	Intermediate Similarity	NPD1247	Approved
0.7746	Intermediate Similarity	NPD3266	Approved
0.7746	Intermediate Similarity	NPD3267	Approved
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7701	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4363	Phase 3
0.7688	Intermediate Similarity	NPD4360	Phase 2
0.7687	Intermediate Similarity	NPD5124	Phase 1
0.7687	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2654	Approved
0.7673	Intermediate Similarity	NPD4288	Approved
0.7669	Intermediate Similarity	NPD3926	Phase 2
0.766	Intermediate Similarity	NPD3972	Approved
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7651	Intermediate Similarity	NPD1729	Discontinued
0.7644	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4361	Phase 2
0.7619	Intermediate Similarity	NPD4307	Phase 2
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7603	Intermediate Similarity	NPD1296	Phase 2
0.7595	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1933	Approved
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD9545	Approved
0.7536	Intermediate Similarity	NPD9493	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD6585	Discontinued
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1164	Approved
0.7484	Intermediate Similarity	NPD5890	Approved
0.7484	Intermediate Similarity	NPD5889	Approved
0.7483	Intermediate Similarity	NPD5404	Approved
0.7483	Intermediate Similarity	NPD5408	Approved
0.7483	Intermediate Similarity	NPD5406	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7483	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7466	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1201	Approved
0.7453	Intermediate Similarity	NPD2296	Approved
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD447	Suspended
0.7445	Intermediate Similarity	NPD1241	Discontinued
0.7434	Intermediate Similarity	NPD1471	Phase 3
0.7403	Intermediate Similarity	NPD7003	Approved
0.7397	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5710	Approved
0.7394	Intermediate Similarity	NPD5711	Approved
0.7389	Intermediate Similarity	NPD5049	Phase 3
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7361	Intermediate Similarity	NPD4749	Approved
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4287	Approved
0.7355	Intermediate Similarity	NPD2354	Approved
0.7353	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7329	Intermediate Similarity	NPD1019	Discontinued
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD17	Approved
0.7322	Intermediate Similarity	NPD7584	Approved
0.7321	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD4661	Approved
0.7208	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2353	Approved
0.7192	Intermediate Similarity	NPD1876	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7152	Intermediate Similarity	NPD3140	Approved
0.7152	Intermediate Similarity	NPD6971	Discontinued
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7134	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7122	Intermediate Similarity	NPD5535	Approved
0.7118	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD7577	Discontinued
0.7117	Intermediate Similarity	NPD6279	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data