NPASS Compound

Structure

CID240593 OpenBabel06191716042D 23 24 0 0 0 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -5.1962 -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 -4.3301 -1.5000 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 1.7321 -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 -1.7321 -1.0000 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 3.4641 -0.0000 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 5.1962 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	340.006
LogP:	5.168
LogD:	4.133
LogS:	-5.565
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	2.188
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:	-4.775
MDCK Permeability:	1.4147915862849914e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	101.63500213623047%
Volume Distribution (VD):	0.667
Pgp-substrate:	1.0889328718185425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.568
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	12.383
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.675
Drug-inuced Liver Injury (DILI):	0.563
AMES Toxicity:	0.842
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.919
Carcinogencity:	0.707
Eye Corrosion:	0.004
Eye Irritation:	0.975
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC240593

Natural Product ID:	NPC240593
*Common Name:**	Cordoin
IUPAC Name:	(E)-1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-phenylprop-2-en-1-one
Synonyms:	Cordoin
Standard InCHIKey:	DGUGLZYULGVSIZ-DHZHZOJOSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-15(2)12-13-23-17-9-10-18(20(22)14-17)19(21)11-8-16-6-4-3-5-7-16/h3-12,14,22H,13H2,1-2H3/b11-8+
SMILES:	CC(=CCOc1ccc(C(=O)/C=C/c2ccccc2)c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450771
PubChem CID:	5961410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514323]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594155]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677277]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10256	Liquidambar orientalis	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10256	Liquidambar orientalis	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26405	Duguetia staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10256	Liquidambar orientalis	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10256	Liquidambar orientalis	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10256	Liquidambar orientalis	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7018	Quamoclit pennata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11494	Echinogorgia complexa	Species	Paramuriceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13666	Salvia phlomoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1322	Solidago arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4006	Crotalaria dura	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26405	Duguetia staudtii	Species	Annonaceae	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	9
MIC	4
Others	12

Activity Type	# Activity
Cell Line	4
Individual Protein	6
NON-MOLECULAR	6
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	54.32	%	PMID[571432]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	58.51	%	PMID[571432]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	18760.0	nM	PMID[571432]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	18620.87	nM	PMID[571432]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	54000.0	nM	PMID[571434]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	71000.0	nM	PMID[571434]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	81000.0	nM	PMID[571434]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	58000.0	nM	PMID[571434]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Activity	=	-16.41	%	PMID[571436]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	18620871.37	nM	PMID[571436]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	2000.0	ug.mL-1	PMID[571431]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MBC	=	2000.0	ug ml-1	PMID[571431]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2000.0	ug.mL-1	PMID[571431]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	>	2000.0	ug ml-1	PMID[571431]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	2000.0	ug.mL-1	PMID[571431]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	2000.0	ug ml-1	PMID[571431]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2000.0	ug.mL-1	PMID[571431]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	2000.0	ug ml-1	PMID[571431]
NPT2	Others	Unspecified		Ratio IC50	>	1.1	n.a.	PMID[571432]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	53000.0	nM	PMID[571434]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39000.0	nM	PMID[571434]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	95.0	%	PMID[571434]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.0	%	PMID[571434]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	16.4	%	PMID[571435]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.3	%	PMID[571435]

☑ 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 NPC240593 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	332
0.1-0.2	1566
0.2-0.3	4286
0.3-0.4	10886
0.4-0.5	7098
0.5-0.6	3730
0.6-0.7	5796
0.7-0.8	5340
0.8-0.85	2114
0.85-0.9	971
0.9-0.95	508
0.95-1	70

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC188879
0.9848	High Similarity	NPC124269
0.9699	High Similarity	NPC188947
0.9699	High Similarity	NPC99333
0.9699	High Similarity	NPC280284
0.9624	High Similarity	NPC250266
0.9624	High Similarity	NPC266597
0.9624	High Similarity	NPC290291
0.9624	High Similarity	NPC275055
0.9618	High Similarity	NPC312318
0.9618	High Similarity	NPC263670
0.9618	High Similarity	NPC472365
0.9618	High Similarity	NPC175098
0.9618	High Similarity	NPC188646
0.9618	High Similarity	NPC242294
0.9618	High Similarity	NPC139813
0.9618	High Similarity	NPC337373
0.9618	High Similarity	NPC56031
0.9618	High Similarity	NPC192304
0.9615	High Similarity	NPC308037
0.9615	High Similarity	NPC64359
0.9556	High Similarity	NPC6407
0.9556	High Similarity	NPC129853
0.9556	High Similarity	NPC188243
0.9556	High Similarity	NPC284550
0.9556	High Similarity	NPC76445
0.9556	High Similarity	NPC110228
0.9549	High Similarity	NPC231772
0.9549	High Similarity	NPC47815
0.9549	High Similarity	NPC473887
0.9549	High Similarity	NPC124784
0.9549	High Similarity	NPC13408
0.9549	High Similarity	NPC194281
0.9549	High Similarity	NPC29353
0.9549	High Similarity	NPC127447
0.9549	High Similarity	NPC234133
0.9545	High Similarity	NPC286336
0.9542	High Similarity	NPC129132
0.9542	High Similarity	NPC205468
0.9542	High Similarity	NPC87231
0.9542	High Similarity	NPC212631
0.9542	High Similarity	NPC203817
0.9542	High Similarity	NPC257756
0.9489	High Similarity	NPC257097
0.9489	High Similarity	NPC143896
0.9489	High Similarity	NPC91560
0.9489	High Similarity	NPC75049
0.9489	High Similarity	NPC175504
0.9489	High Similarity	NPC310130
0.9489	High Similarity	NPC221432
0.9489	High Similarity	NPC169591
0.9489	High Similarity	NPC68104
0.9489	High Similarity	NPC39329
0.9489	High Similarity	NPC150408
0.9489	High Similarity	NPC164980
0.9489	High Similarity	NPC149026
0.9485	High Similarity	NPC3188
0.9485	High Similarity	NPC110969
0.9481	High Similarity	NPC329203
0.9481	High Similarity	NPC310135
0.9481	High Similarity	NPC225153
0.9481	High Similarity	NPC20709
0.9481	High Similarity	NPC140890
0.9481	High Similarity	NPC274784
0.9481	High Similarity	NPC261234
0.9481	High Similarity	NPC265871
0.9481	High Similarity	NPC222342
0.9481	High Similarity	NPC150648
0.9478	High Similarity	NPC476480
0.9478	High Similarity	NPC228661
0.9478	High Similarity	NPC84585
0.947	High Similarity	NPC144051
0.947	High Similarity	NPC18877
0.947	High Similarity	NPC204960
0.947	High Similarity	NPC294593
0.947	High Similarity	NPC82225
0.947	High Similarity	NPC57601
0.947	High Similarity	NPC159623
0.947	High Similarity	NPC20560
0.947	High Similarity	NPC28753
0.9466	High Similarity	NPC262359
0.9466	High Similarity	NPC313618
0.942	High Similarity	NPC473015
0.942	High Similarity	NPC197252
0.942	High Similarity	NPC209040
0.942	High Similarity	NPC236766
0.942	High Similarity	NPC473013
0.9416	High Similarity	NPC167624
0.9416	High Similarity	NPC64915
0.9416	High Similarity	NPC76338
0.9416	High Similarity	NPC220998
0.9416	High Similarity	NPC228504
0.9416	High Similarity	NPC227579
0.9416	High Similarity	NPC78
0.9416	High Similarity	NPC223500
0.9416	High Similarity	NPC265040
0.9416	High Similarity	NPC177354
0.9416	High Similarity	NPC10937
0.9416	High Similarity	NPC40833
0.9416	High Similarity	NPC1089
0.9416	High Similarity	NPC125855
0.9416	High Similarity	NPC182852
0.9416	High Similarity	NPC296917
0.9416	High Similarity	NPC328164
0.9416	High Similarity	NPC306829
0.9416	High Similarity	NPC66515
0.9416	High Similarity	NPC76372
0.9416	High Similarity	NPC148757
0.9416	High Similarity	NPC32739
0.9416	High Similarity	NPC226636
0.9416	High Similarity	NPC166482
0.9416	High Similarity	NPC324134
0.9416	High Similarity	NPC107572
0.9416	High Similarity	NPC202981
0.9416	High Similarity	NPC161506
0.9416	High Similarity	NPC11561
0.9416	High Similarity	NPC37496
0.9416	High Similarity	NPC166934
0.9416	High Similarity	NPC194432
0.9416	High Similarity	NPC324436
0.9412	High Similarity	NPC172986
0.9412	High Similarity	NPC159275
0.9412	High Similarity	NPC281207
0.9412	High Similarity	NPC305355
0.9412	High Similarity	NPC269652
0.9412	High Similarity	NPC261227
0.9412	High Similarity	NPC475680
0.9412	High Similarity	NPC241100
0.9412	High Similarity	NPC270883
0.9412	High Similarity	NPC69769
0.9407	High Similarity	NPC329225
0.9407	High Similarity	NPC118813
0.9407	High Similarity	NPC147686
0.9407	High Similarity	NPC472460
0.9403	High Similarity	NPC41461
0.9403	High Similarity	NPC25287
0.9403	High Similarity	NPC477244
0.9403	High Similarity	NPC274109
0.9403	High Similarity	NPC150399
0.9403	High Similarity	NPC98115
0.9403	High Similarity	NPC476333
0.9403	High Similarity	NPC12165
0.9403	High Similarity	NPC186838
0.9403	High Similarity	NPC477242
0.9403	High Similarity	NPC187826
0.9403	High Similarity	NPC168105
0.9403	High Similarity	NPC249606
0.9403	High Similarity	NPC477243
0.9403	High Similarity	NPC66349
0.9403	High Similarity	NPC1486
0.9403	High Similarity	NPC472367
0.9403	High Similarity	NPC473391
0.9403	High Similarity	NPC472364
0.9398	High Similarity	NPC125269
0.9398	High Similarity	NPC144027
0.9398	High Similarity	NPC172262
0.9398	High Similarity	NPC236974
0.9394	High Similarity	NPC10971
0.9353	High Similarity	NPC99454
0.9353	High Similarity	NPC299011
0.9353	High Similarity	NPC130176
0.9348	High Similarity	NPC214166
0.9348	High Similarity	NPC185276
0.9348	High Similarity	NPC81697
0.9348	High Similarity	NPC18585
0.9348	High Similarity	NPC478086
0.9348	High Similarity	NPC316816
0.9348	High Similarity	NPC125894
0.9348	High Similarity	NPC223812
0.9348	High Similarity	NPC77794
0.9348	High Similarity	NPC85162
0.9348	High Similarity	NPC278249
0.9348	High Similarity	NPC106985
0.9348	High Similarity	NPC166138
0.9348	High Similarity	NPC107177
0.9343	High Similarity	NPC136840
0.9343	High Similarity	NPC110038
0.9343	High Similarity	NPC166689
0.9343	High Similarity	NPC64908
0.9343	High Similarity	NPC282300
0.9343	High Similarity	NPC90582
0.9343	High Similarity	NPC324386
0.9343	High Similarity	NPC96408
0.9343	High Similarity	NPC262094
0.9343	High Similarity	NPC17170
0.9343	High Similarity	NPC248372
0.9343	High Similarity	NPC118840
0.9343	High Similarity	NPC213322
0.9343	High Similarity	NPC103362
0.9343	High Similarity	NPC4743
0.9343	High Similarity	NPC156190
0.9343	High Similarity	NPC156590
0.9343	High Similarity	NPC147688
0.9343	High Similarity	NPC258630
0.9343	High Similarity	NPC205006
0.9343	High Similarity	NPC279650
0.9343	High Similarity	NPC312391
0.9338	High Similarity	NPC301217
0.9338	High Similarity	NPC143799
0.9338	High Similarity	NPC96565

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 NPC240593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	951
0.2-0.3	1524
0.3-0.4	2600
0.4-0.5	1856
0.5-0.6	1219
0.6-0.7	465
0.7-0.8	150
0.8-0.85	44
0.85-0.9	15
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD1240	Approved
0.9407	High Similarity	NPD1549	Phase 2
0.9333	High Similarity	NPD1552	Clinical (unspecified phase)
0.9333	High Similarity	NPD1550	Clinical (unspecified phase)
0.9323	High Similarity	NPD1607	Approved
0.9259	High Similarity	NPD2796	Approved
0.9185	High Similarity	NPD1510	Phase 2
0.9143	High Similarity	NPD4378	Clinical (unspecified phase)
0.9071	High Similarity	NPD6799	Approved
0.9007	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD7411	Suspended
0.8784	High Similarity	NPD3882	Suspended
0.8776	High Similarity	NPD2393	Clinical (unspecified phase)
0.8741	High Similarity	NPD6859	Clinical (unspecified phase)
0.8725	High Similarity	NPD7075	Discontinued
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8707	High Similarity	NPD1934	Approved
0.8705	High Similarity	NPD1551	Phase 2
0.8699	High Similarity	NPD4380	Phase 2
0.8699	High Similarity	NPD6599	Discontinued
0.8671	High Similarity	NPD1511	Approved
0.8649	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD2801	Approved
0.8649	High Similarity	NPD7096	Clinical (unspecified phase)
0.86	High Similarity	NPD4381	Clinical (unspecified phase)
0.8581	High Similarity	NPD6801	Discontinued
0.8552	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3750	Approved
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD7768	Phase 2
0.8387	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD2344	Approved
0.837	Intermediate Similarity	NPD1203	Approved
0.8367	Intermediate Similarity	NPD5403	Approved
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD6832	Phase 2
0.8269	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6166	Phase 2
0.8264	Intermediate Similarity	NPD2800	Approved
0.8264	Intermediate Similarity	NPD1243	Approved
0.8235	Intermediate Similarity	NPD3749	Approved
0.8231	Intermediate Similarity	NPD5401	Approved
0.8227	Intermediate Similarity	NPD6651	Approved
0.8219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD1548	Phase 1
0.8165	Intermediate Similarity	NPD3818	Discontinued
0.8151	Intermediate Similarity	NPD2309	Approved
0.8148	Intermediate Similarity	NPD9717	Approved
0.8125	Intermediate Similarity	NPD5953	Discontinued
0.8121	Intermediate Similarity	NPD920	Approved
0.8113	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7054	Approved
0.8113	Intermediate Similarity	NPD7286	Phase 2
0.8112	Intermediate Similarity	NPD3748	Approved
0.8112	Intermediate Similarity	NPD2799	Discontinued
0.8108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD4628	Phase 3
0.8074	Intermediate Similarity	NPD422	Phase 1
0.8063	Intermediate Similarity	NPD7472	Approved
0.8063	Intermediate Similarity	NPD7074	Phase 3
0.8052	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD9545	Approved
0.8013	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD5402	Approved
0.7963	Intermediate Similarity	NPD7251	Discontinued
0.7958	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7939	Intermediate Similarity	NPD1241	Discontinued
0.7931	Intermediate Similarity	NPD6100	Approved
0.7931	Intermediate Similarity	NPD6099	Approved
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD2798	Approved
0.7914	Intermediate Similarity	NPD7808	Phase 3
0.7914	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD9493	Approved
0.7891	Intermediate Similarity	NPD2654	Approved
0.7883	Intermediate Similarity	NPD3972	Approved
0.7862	Intermediate Similarity	NPD7033	Discontinued
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.7842	Intermediate Similarity	NPD2797	Approved
0.7817	Intermediate Similarity	NPD2313	Discontinued
0.7817	Intermediate Similarity	NPD3268	Approved
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.775	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1729	Discontinued
0.7722	Intermediate Similarity	NPD919	Approved
0.7669	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD3226	Approved
0.766	Intermediate Similarity	NPD1019	Discontinued
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7655	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD3225	Approved
0.7626	Intermediate Similarity	NPD1608	Approved
0.7625	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3140	Approved
0.7586	Intermediate Similarity	NPD3142	Approved
0.7576	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD411	Approved
0.7534	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2296	Approved
0.753	Intermediate Similarity	NPD6104	Discontinued
0.7518	Intermediate Similarity	NPD1894	Discontinued
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD4662	Approved
0.7516	Intermediate Similarity	NPD4661	Approved
0.7471	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7465	Intermediate Similarity	NPD3267	Approved
0.7465	Intermediate Similarity	NPD3266	Approved
0.7457	Intermediate Similarity	NPD4360	Phase 2
0.7457	Intermediate Similarity	NPD4363	Phase 3
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7390	Discontinued
0.7448	Intermediate Similarity	NPD1296	Phase 2
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7421	Intermediate Similarity	NPD4288	Approved
0.7415	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5124	Phase 1
0.7414	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4361	Phase 2
0.741	Intermediate Similarity	NPD17	Approved
0.7405	Intermediate Similarity	NPD6280	Approved
0.7405	Intermediate Similarity	NPD6279	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1876	Approved
0.7383	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4625	Phase 3
0.7378	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1481	Phase 2
0.7362	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD5710	Approved
0.7361	Intermediate Similarity	NPD9494	Approved
0.7347	Intermediate Similarity	NPD1613	Approved
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7347	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD3764	Approved
0.7325	Intermediate Similarity	NPD7458	Discontinued
0.7324	Intermediate Similarity	NPD4749	Approved
0.732	Intermediate Similarity	NPD3887	Approved
0.732	Intermediate Similarity	NPD2354	Approved
0.731	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1201	Approved
0.7305	Intermediate Similarity	NPD1535	Discovery
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.7296	Intermediate Similarity	NPD6844	Discontinued
0.7296	Intermediate Similarity	NPD7577	Discontinued
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7440	Discontinued
0.726	Intermediate Similarity	NPD3027	Phase 3
0.7255	Intermediate Similarity	NPD7003	Approved
0.7247	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD5890	Approved
0.7233	Intermediate Similarity	NPD5889	Approved
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4287	Approved
0.7222	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD6971	Discontinued
0.7219	Intermediate Similarity	NPD4476	Approved
0.7219	Intermediate Similarity	NPD4477	Approved
0.7219	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7199	Phase 2
0.7192	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7186	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5940	Clinical (unspecified phase)

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