NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	96.06
Volume:	107.293
LogP:	2.241
LogD:	2.269
LogS:	-1.955
# Rotatable Bonds:	1
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	2.076
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.238
MDCK Permeability:	3.289586675236933e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.441
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.144
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	91.41971588134766%
Volume Distribution (VD):	2.668
Pgp-substrate:	16.810808181762695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.536
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.278
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	11.447
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.209
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.726
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.187
Carcinogencity:	0.732
Eye Corrosion:	0.966
Eye Irritation:	0.991
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC156768

Natural Product ID:	NPC156768
*Common Name:**	2-Ethylfuran
IUPAC Name:	2-ethylfuran
Synonyms:
Standard InCHIKey:	HLPIHRDZBHXTFJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H8O/c1-2-6-4-3-5-7-6/h3-5H,2H2,1H3
SMILES:	CCc1ccco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269084
PubChem CID:	18554
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24014097]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128451]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11411	Gossypium herbaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26429	Capsella bursa-pastoris	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26429	Capsella bursa-pastoris	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11411	Gossypium herbaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26429	Capsella bursa-pastoris	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31579	Artemisia capillaries	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7576	Brassica oleracea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26429	Capsella bursa-pastoris	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11411	Gossypium herbaceum	Species	Malvaceae	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
NPO7576	NPC156768	Other	Stem	0.008	0.008	0.008	mg/100g	Database [DUKE]

☑ 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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT563	Organism	Escherichia coli O157:H7	Escherichia coli O157:H7	GI	=	0.0	%	PMID[494146]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	=	4.3	%	PMID[494146]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	GI	=	0.0	%	PMID[494146]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	GI	=	2.3	%	PMID[494146]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	GI	=	1.6	%	PMID[494146]
NPT314	Organism	Bacillus cereus	Bacillus cereus	GI	=	0.0	%	PMID[494146]

☑ 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 NPC156768 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	442
0.1-0.2	4438
0.2-0.3	11195
0.3-0.4	8650
0.4-0.5	7951
0.5-0.6	8672
0.6-0.7	1191
0.7-0.8	131
0.8-0.85	18
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC146316
0.949	High Similarity	NPC42471
0.9355	High Similarity	NPC233791
0.901	High Similarity	NPC219969
0.8889	High Similarity	NPC217226
0.8774	High Similarity	NPC292036
0.8725	High Similarity	NPC298087
0.8611	High Similarity	NPC476031
0.8611	High Similarity	NPC476014
0.8571	High Similarity	NPC229387
0.8519	High Similarity	NPC205523
0.8455	Intermediate Similarity	NPC21831
0.8455	Intermediate Similarity	NPC187547
0.844	Intermediate Similarity	NPC474987
0.8364	Intermediate Similarity	NPC312525
0.8364	Intermediate Similarity	NPC217180
0.8302	Intermediate Similarity	NPC209111
0.8288	Intermediate Similarity	NPC254958
0.8288	Intermediate Similarity	NPC291619
0.8241	Intermediate Similarity	NPC22678
0.8198	Intermediate Similarity	NPC107482
0.8125	Intermediate Similarity	NPC206007
0.8037	Intermediate Similarity	NPC471521
0.8037	Intermediate Similarity	NPC473356
0.8018	Intermediate Similarity	NPC11821
0.8017	Intermediate Similarity	NPC118853
0.8	Intermediate Similarity	NPC311987
0.7963	Intermediate Similarity	NPC177331
0.7949	Intermediate Similarity	NPC473885
0.7949	Intermediate Similarity	NPC471074
0.7946	Intermediate Similarity	NPC76844
0.7944	Intermediate Similarity	NPC140688
0.7928	Intermediate Similarity	NPC252004
0.7895	Intermediate Similarity	NPC4898
0.7895	Intermediate Similarity	NPC244862
0.7895	Intermediate Similarity	NPC67345
0.7895	Intermediate Similarity	NPC137710
0.7881	Intermediate Similarity	NPC83301
0.7876	Intermediate Similarity	NPC131801
0.7876	Intermediate Similarity	NPC227660
0.7857	Intermediate Similarity	NPC28054
0.7845	Intermediate Similarity	NPC272487
0.7818	Intermediate Similarity	NPC105249
0.7815	Intermediate Similarity	NPC141059
0.7788	Intermediate Similarity	NPC45536
0.7788	Intermediate Similarity	NPC328451
0.7788	Intermediate Similarity	NPC59035
0.7788	Intermediate Similarity	NPC79202
0.7748	Intermediate Similarity	NPC1811
0.7748	Intermediate Similarity	NPC26157
0.7739	Intermediate Similarity	NPC473969
0.7739	Intermediate Similarity	NPC244293
0.7692	Intermediate Similarity	NPC174915
0.7692	Intermediate Similarity	NPC270807
0.7686	Intermediate Similarity	NPC59502
0.7658	Intermediate Similarity	NPC57879
0.7658	Intermediate Similarity	NPC54626
0.7652	Intermediate Similarity	NPC243704
0.7634	Intermediate Similarity	NPC225539
0.7632	Intermediate Similarity	NPC316062
0.7607	Intermediate Similarity	NPC97566
0.7563	Intermediate Similarity	NPC188377
0.7563	Intermediate Similarity	NPC65735
0.7561	Intermediate Similarity	NPC475092
0.7544	Intermediate Similarity	NPC150895
0.7522	Intermediate Similarity	NPC53953
0.7521	Intermediate Similarity	NPC246214
0.75	Intermediate Similarity	NPC473982
0.7458	Intermediate Similarity	NPC115859
0.7458	Intermediate Similarity	NPC79557
0.7458	Intermediate Similarity	NPC474136
0.7458	Intermediate Similarity	NPC1848
0.7438	Intermediate Similarity	NPC52035
0.7438	Intermediate Similarity	NPC216810
0.7419	Intermediate Similarity	NPC477645
0.7417	Intermediate Similarity	NPC11799
0.7417	Intermediate Similarity	NPC141252
0.7414	Intermediate Similarity	NPC208906
0.7414	Intermediate Similarity	NPC144745
0.7411	Intermediate Similarity	NPC183648
0.7398	Intermediate Similarity	NPC50583
0.7395	Intermediate Similarity	NPC283284
0.7395	Intermediate Similarity	NPC289911
0.7395	Intermediate Similarity	NPC263870
0.7381	Intermediate Similarity	NPC106247
0.7377	Intermediate Similarity	NPC184391
0.7373	Intermediate Similarity	NPC474817
0.7345	Intermediate Similarity	NPC23332
0.7333	Intermediate Similarity	NPC475818
0.7333	Intermediate Similarity	NPC476351
0.7328	Intermediate Similarity	NPC470860
0.7295	Intermediate Similarity	NPC470858
0.7273	Intermediate Similarity	NPC178382
0.725	Intermediate Similarity	NPC471549
0.725	Intermediate Similarity	NPC473379
0.7222	Intermediate Similarity	NPC13755
0.7216	Intermediate Similarity	NPC124576
0.7213	Intermediate Similarity	NPC75557
0.7213	Intermediate Similarity	NPC71274
0.7213	Intermediate Similarity	NPC474829
0.7209	Intermediate Similarity	NPC215109
0.7209	Intermediate Similarity	NPC307401
0.7209	Intermediate Similarity	NPC473268
0.7209	Intermediate Similarity	NPC170604
0.7203	Intermediate Similarity	NPC87466
0.7188	Intermediate Similarity	NPC265793
0.7188	Intermediate Similarity	NPC209858
0.7177	Intermediate Similarity	NPC329707
0.7156	Intermediate Similarity	NPC84325
0.7154	Intermediate Similarity	NPC130976
0.7154	Intermediate Similarity	NPC472376
0.7154	Intermediate Similarity	NPC329922
0.7154	Intermediate Similarity	NPC474260
0.7154	Intermediate Similarity	NPC329694
0.7154	Intermediate Similarity	NPC81912
0.7154	Intermediate Similarity	NPC473626
0.7143	Intermediate Similarity	NPC136340
0.7131	Intermediate Similarity	NPC243269
0.7119	Intermediate Similarity	NPC217423
0.7119	Intermediate Similarity	NPC45104
0.7117	Intermediate Similarity	NPC128730
0.7107	Intermediate Similarity	NPC477967
0.7107	Intermediate Similarity	NPC314329
0.7107	Intermediate Similarity	NPC317217
0.7099	Intermediate Similarity	NPC202260
0.7097	Intermediate Similarity	NPC474830
0.7083	Intermediate Similarity	NPC230951
0.7077	Intermediate Similarity	NPC64157
0.7077	Intermediate Similarity	NPC278832
0.7073	Intermediate Similarity	NPC471559
0.7069	Intermediate Similarity	NPC279916
0.7063	Intermediate Similarity	NPC66246
0.7063	Intermediate Similarity	NPC939
0.7063	Intermediate Similarity	NPC170546
0.7059	Intermediate Similarity	NPC32298
0.7059	Intermediate Similarity	NPC293424
0.7054	Intermediate Similarity	NPC176971
0.7054	Intermediate Similarity	NPC324117
0.7049	Intermediate Similarity	NPC291189
0.7049	Intermediate Similarity	NPC16922
0.7049	Intermediate Similarity	NPC69403
0.7045	Intermediate Similarity	NPC473983
0.7045	Intermediate Similarity	NPC201370
0.7045	Intermediate Similarity	NPC148374
0.7043	Intermediate Similarity	NPC277525
0.704	Intermediate Similarity	NPC474279
0.704	Intermediate Similarity	NPC474438
0.7037	Intermediate Similarity	NPC175298
0.7031	Intermediate Similarity	NPC293253
0.703	Intermediate Similarity	NPC125306
0.7027	Intermediate Similarity	NPC38209
0.7025	Intermediate Similarity	NPC295317
0.7008	Intermediate Similarity	NPC183348
0.7008	Intermediate Similarity	NPC282230
0.7	Intermediate Similarity	NPC54243
0.7	Intermediate Similarity	NPC35744
0.6992	Remote Similarity	NPC477038
0.6992	Remote Similarity	NPC477965
0.6991	Remote Similarity	NPC151530
0.6991	Remote Similarity	NPC157473
0.6975	Remote Similarity	NPC469954
0.697	Remote Similarity	NPC233707
0.696	Remote Similarity	NPC476016
0.696	Remote Similarity	NPC95567
0.696	Remote Similarity	NPC319140
0.696	Remote Similarity	NPC471573
0.696	Remote Similarity	NPC290955
0.696	Remote Similarity	NPC473355
0.696	Remote Similarity	NPC471501
0.696	Remote Similarity	NPC246392
0.696	Remote Similarity	NPC137570
0.696	Remote Similarity	NPC471554
0.6953	Remote Similarity	NPC15083
0.6953	Remote Similarity	NPC470977
0.6953	Remote Similarity	NPC196979
0.6953	Remote Similarity	NPC470976
0.6952	Remote Similarity	NPC318429
0.6949	Remote Similarity	NPC220540
0.6949	Remote Similarity	NPC188907
0.694	Remote Similarity	NPC263337
0.6937	Remote Similarity	NPC298224
0.6937	Remote Similarity	NPC179686
0.6935	Remote Similarity	NPC221798
0.6935	Remote Similarity	NPC179354
0.6929	Remote Similarity	NPC21460
0.6929	Remote Similarity	NPC45947
0.6923	Remote Similarity	NPC159786
0.6923	Remote Similarity	NPC90903
0.6917	Remote Similarity	NPC171023
0.6917	Remote Similarity	NPC152159
0.6905	Remote Similarity	NPC26532
0.6905	Remote Similarity	NPC279877
0.6899	Remote Similarity	NPC470859
0.6899	Remote Similarity	NPC470740
0.6889	Remote Similarity	NPC27220
0.6881	Remote Similarity	NPC95755
0.688	Remote Similarity	NPC74612
0.688	Remote Similarity	NPC46536
0.688	Remote Similarity	NPC23086
0.688	Remote Similarity	NPC224657

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 NPC156768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1323
0.2-0.3	2715
0.3-0.4	2656
0.4-0.5	1459
0.5-0.6	520
0.6-0.7	71
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8198	Intermediate Similarity	NPD9092	Discovery
0.7522	Intermediate Similarity	NPD1241	Discontinued
0.7438	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD9069	Phase 1
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9365	Approved
0.6825	Remote Similarity	NPD1019	Discontinued
0.6774	Remote Similarity	NPD9717	Approved
0.6754	Remote Similarity	NPD3134	Approved
0.6719	Remote Similarity	NPD6832	Phase 2
0.6696	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6641	Remote Similarity	NPD3142	Approved
0.6641	Remote Similarity	NPD9494	Approved
0.6641	Remote Similarity	NPD3140	Approved
0.664	Remote Similarity	NPD3972	Approved
0.6604	Remote Similarity	NPD9295	Approved
0.6594	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2344	Approved
0.6593	Remote Similarity	NPD1471	Phase 3
0.6549	Remote Similarity	NPD291	Approved
0.6525	Remote Similarity	NPD920	Approved
0.6522	Remote Similarity	NPD9697	Approved
0.6504	Remote Similarity	NPD9545	Approved
0.65	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1203	Approved
0.6466	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD769	Approved
0.6403	Remote Similarity	NPD2309	Approved
0.6397	Remote Similarity	NPD2796	Approved
0.6397	Remote Similarity	NPD1551	Phase 2
0.6387	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1243	Approved
0.6372	Remote Similarity	NPD1238	Approved
0.6343	Remote Similarity	NPD1933	Approved
0.6341	Remote Similarity	NPD9493	Approved
0.6331	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5585	Approved
0.6308	Remote Similarity	NPD5647	Approved
0.6308	Remote Similarity	NPD2798	Approved
0.6306	Remote Similarity	NPD9296	Approved
0.6294	Remote Similarity	NPD3869	Phase 3
0.6294	Remote Similarity	NPD3873	Phase 3
0.6293	Remote Similarity	NPD9501	Approved
0.629	Remote Similarity	NPD5536	Phase 2
0.6271	Remote Similarity	NPD290	Approved
0.6271	Remote Similarity	NPD5373	Approved
0.6271	Remote Similarity	NPD5374	Approved
0.6271	Remote Similarity	NPD9624	Approved
0.627	Remote Similarity	NPD1778	Approved
0.627	Remote Similarity	NPD17	Approved
0.6269	Remote Similarity	NPD4307	Phase 2
0.6259	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD2313	Discontinued
0.6241	Remote Similarity	NPD411	Approved
0.624	Remote Similarity	NPD1894	Discontinued
0.6231	Remote Similarity	NPD3267	Approved
0.6231	Remote Similarity	NPD3266	Approved
0.6222	Remote Similarity	NPD447	Suspended
0.6218	Remote Similarity	NPD2684	Approved
0.6204	Remote Similarity	NPD2799	Discontinued
0.62	Remote Similarity	NPD919	Approved
0.6198	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6279	Approved
0.619	Remote Similarity	NPD6280	Approved
0.6187	Remote Similarity	NPD1549	Phase 2
0.6186	Remote Similarity	NPD968	Approved
0.617	Remote Similarity	NPD3887	Approved
0.6167	Remote Similarity	NPD556	Approved
0.6148	Remote Similarity	NPD1240	Approved
0.6134	Remote Similarity	NPD9552	Approved
0.6131	Remote Similarity	NPD743	Approved
0.6124	Remote Similarity	NPD1608	Approved
0.6118	Remote Similarity	NPD1247	Approved
0.6116	Remote Similarity	NPD2671	Approved
0.6116	Remote Similarity	NPD2673	Approved
0.6115	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD2353	Approved
0.6115	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6362	Approved
0.6107	Remote Similarity	NPD2797	Approved
0.6099	Remote Similarity	NPD4628	Phase 3
0.6094	Remote Similarity	NPD3496	Discontinued
0.6087	Remote Similarity	NPD3748	Approved
0.6087	Remote Similarity	NPD4308	Phase 3
0.6084	Remote Similarity	NPD6799	Approved
0.6083	Remote Similarity	NPD2182	Approved
0.6077	Remote Similarity	NPD4359	Approved
0.6068	Remote Similarity	NPD9261	Approved
0.6063	Remote Similarity	NPD1651	Approved
0.6058	Remote Similarity	NPD1607	Approved
0.6042	Remote Similarity	NPD4661	Approved
0.6042	Remote Similarity	NPD4662	Approved
0.6017	Remote Similarity	NPD164	Approved
0.6016	Remote Similarity	NPD5535	Approved
0.6016	Remote Similarity	NPD821	Approved
0.6016	Remote Similarity	NPD7843	Approved
0.6015	Remote Similarity	NPD454	Approved
0.6	Remote Similarity	NPD6273	Approved
0.6	Remote Similarity	NPD2346	Discontinued
0.6	Remote Similarity	NPD3268	Approved
0.6	Remote Similarity	NPD1481	Phase 2
0.5971	Remote Similarity	NPD1510	Phase 2
0.5959	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD2354	Approved
0.5938	Remote Similarity	NPD5691	Approved
0.5931	Remote Similarity	NPD5401	Approved
0.5926	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD1281	Approved
0.5923	Remote Similarity	NPD1535	Discovery
0.592	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD957	Approved
0.5909	Remote Similarity	NPD5262	Discontinued
0.5909	Remote Similarity	NPD3225	Approved
0.5903	Remote Similarity	NPD7440	Discontinued
0.5894	Remote Similarity	NPD2296	Approved
0.5891	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.589	Remote Similarity	NPD2186	Approved
0.5882	Remote Similarity	NPD6798	Discontinued
0.5882	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD2649	Approved
0.5878	Remote Similarity	NPD2651	Approved
0.5874	Remote Similarity	NPD3750	Approved
0.5874	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD2557	Approved
0.5873	Remote Similarity	NPD7157	Approved
0.5872	Remote Similarity	NPD9259	Approved
0.5872	Remote Similarity	NPD9257	Approved
0.5871	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD6808	Phase 2
0.587	Remote Similarity	NPD4622	Approved
0.587	Remote Similarity	NPD6355	Discontinued
0.587	Remote Similarity	NPD4618	Approved
0.5868	Remote Similarity	NPD9267	Approved
0.5868	Remote Similarity	NPD9263	Approved
0.5868	Remote Similarity	NPD9264	Approved
0.5868	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD1182	Approved
0.5855	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD3882	Suspended
0.585	Remote Similarity	NPD3613	Discontinued
0.585	Remote Similarity	NPD5403	Approved
0.584	Remote Similarity	NPD594	Approved
0.584	Remote Similarity	NPD592	Approved
0.5839	Remote Similarity	NPD8032	Phase 2
0.5839	Remote Similarity	NPD6599	Discontinued
0.5839	Remote Similarity	NPD4062	Phase 3
0.5839	Remote Similarity	NPD1143	Approved
0.5839	Remote Similarity	NPD1140	Approved
0.5839	Remote Similarity	NPD6233	Phase 2
0.5839	Remote Similarity	NPD1142	Approved
0.5839	Remote Similarity	NPD1141	Approved
0.5828	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD3596	Phase 2
0.5822	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.582	Remote Similarity	NPD9266	Approved
0.582	Remote Similarity	NPD74	Approved
0.5816	Remote Similarity	NPD2935	Discontinued
0.5816	Remote Similarity	NPD5712	Approved
0.5804	Remote Similarity	NPD2654	Approved
0.5802	Remote Similarity	NPD422	Phase 1
0.58	Remote Similarity	NPD7411	Suspended
0.58	Remote Similarity	NPD958	Approved
0.5796	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1283	Approved
0.5786	Remote Similarity	NPD5689	Approved
0.5786	Remote Similarity	NPD1212	Approved
0.5786	Remote Similarity	NPD5688	Approved
0.5784	Remote Similarity	NPD9087	Approved
0.5781	Remote Similarity	NPD1102	Approved
0.5781	Remote Similarity	NPD1103	Approved
0.5781	Remote Similarity	NPD254	Approved
0.5781	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6764	Approved
0.5776	Remote Similarity	NPD6559	Discontinued
0.5776	Remote Similarity	NPD6765	Approved
0.5766	Remote Similarity	NPD3764	Approved
0.5766	Remote Similarity	NPD1296	Phase 2
0.5762	Remote Similarity	NPD6844	Discontinued
0.5762	Remote Similarity	NPD7577	Discontinued
0.5752	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.575	Remote Similarity	NPD2425	Phase 1
0.575	Remote Similarity	NPD1237	Approved
0.5748	Remote Similarity	NPD191	Approved
0.5745	Remote Similarity	NPD7033	Discontinued
0.5743	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD5494	Approved
0.5736	Remote Similarity	NPD6580	Approved
0.5736	Remote Similarity	NPD6581	Approved
0.5736	Remote Similarity	NPD7533	Approved
0.5736	Remote Similarity	NPD7534	Approved
0.5734	Remote Similarity	NPD2424	Discontinued
0.5732	Remote Similarity	NPD3926	Phase 2
0.5725	Remote Similarity	NPD4870	Approved
0.5725	Remote Similarity	NPD3847	Discontinued
0.5725	Remote Similarity	NPD155	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