NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.09
Volume:	214.871
LogP:	3.06
LogD:	2.77
LogS:	-3.021
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	2.358
Fsp3:	0.364
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:	-4.691
MDCK Permeability:	1.4155140888760798e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.544

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	88.99236297607422%
Volume Distribution (VD):	0.966
Pgp-substrate:	12.939273834228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.266
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	14.602
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.623
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.924
Carcinogencity:	0.13
Eye Corrosion:	0.088
Eye Irritation:	0.967
Respiratory Toxicity:	0.455

Download Data

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

Natural Product: NPC146642

Natural Product ID:	NPC146642
*Common Name:**	3-Methyl-1-(2,4,6-Trihydroxyphenyl)Butan-1-One
IUPAC Name:	3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
Synonyms:
Standard InCHIKey:	VSDWHZGJGWMIRN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O4/c1-6(2)3-8(13)11-9(14)4-7(12)5-10(11)15/h4-6,12,14-15H,3H2,1-2H3
SMILES:	CC(CC(=O)c1c(O)cc(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL19948
PubChem CID:	441269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.12691/jfnr-2-5-9]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217296]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499319]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast	2003-JUN	PMID[18298079]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[19628108]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[22538527]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[24811150]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[28274428]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30236698]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	Guangzhou, China		PMID[30563201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30583361]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30599958]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31159190]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31861466]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13585	Rapanea lancifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12196	Buphane fischeri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12700	Diospyros eriantha	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11848	Lemaireocereus griseus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13671	Ononis vaginalis	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	2
Others	4

Activity Type	# Activity
Individual Protein	1
Organism	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	22.7	%	PMID[466615]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	96.6	%	PMID[466615]
NPT938	Organism	Cavia porcellus	Cavia porcellus	IC50	=	4700.0	nM	PMID[466615]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	30.5	%	PMID[466615]
NPT869	Individual Protein	Free fatty acid receptor 1	Homo sapiens	FC	=	1.116	n.a.	PMID[466616]
NPT21726	SINGLE PROTEIN	Tyrosine-protein kinase SRC	Mus musculus	IC50	=	50600.0	nM	PMID[466617]

☑ 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 NPC146642 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	312
0.1-0.2	1542
0.2-0.3	4115
0.3-0.4	11413
0.4-0.5	7846
0.5-0.6	5349
0.6-0.7	6809
0.7-0.8	4349
0.8-0.85	673
0.85-0.9	206
0.9-0.95	70
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC294037
0.9735	High Similarity	NPC209486
0.9735	High Similarity	NPC40649
0.9652	High Similarity	NPC149246
0.9576	High Similarity	NPC475733
0.9573	High Similarity	NPC65761
0.9573	High Similarity	NPC472029
0.9569	High Similarity	NPC215392
0.9487	High Similarity	NPC91105
0.9478	High Similarity	NPC161617
0.9402	High Similarity	NPC226275
0.9402	High Similarity	NPC242895
0.9322	High Similarity	NPC32032
0.9322	High Similarity	NPC309765
0.9322	High Similarity	NPC133909
0.925	High Similarity	NPC10926
0.925	High Similarity	NPC477454
0.9237	High Similarity	NPC156139
0.9237	High Similarity	NPC45438
0.9237	High Similarity	NPC73532
0.9237	High Similarity	NPC143427
0.9237	High Similarity	NPC267552
0.9237	High Similarity	NPC303737
0.9237	High Similarity	NPC224273
0.9237	High Similarity	NPC115159
0.9237	High Similarity	NPC19174
0.9211	High Similarity	NPC276111
0.9211	High Similarity	NPC118288
0.918	High Similarity	NPC473017
0.9174	High Similarity	NPC267846
0.9174	High Similarity	NPC8745
0.9174	High Similarity	NPC473691
0.9167	High Similarity	NPC13238
0.9153	High Similarity	NPC297186
0.9138	High Similarity	NPC121259
0.9106	High Similarity	NPC212379
0.9106	High Similarity	NPC69235
0.9106	High Similarity	NPC474998
0.9098	High Similarity	NPC105157
0.9098	High Similarity	NPC162612
0.9098	High Similarity	NPC72158
0.9098	High Similarity	NPC30501
0.9098	High Similarity	NPC266689
0.9098	High Similarity	NPC116513
0.9098	High Similarity	NPC169250
0.9098	High Similarity	NPC98254
0.9098	High Similarity	NPC100067
0.9098	High Similarity	NPC190043
0.9098	High Similarity	NPC23126
0.9098	High Similarity	NPC103356
0.9091	High Similarity	NPC262671
0.9091	High Similarity	NPC201728
0.9076	High Similarity	NPC196976
0.9068	High Similarity	NPC159525
0.904	High Similarity	NPC175738
0.9024	High Similarity	NPC221777
0.9024	High Similarity	NPC21305
0.9024	High Similarity	NPC41263
0.9016	High Similarity	NPC62952
0.8983	High Similarity	NPC158222
0.8974	High Similarity	NPC230349
0.8952	High Similarity	NPC92624
0.8952	High Similarity	NPC109123
0.8943	High Similarity	NPC305518
0.8943	High Similarity	NPC128428
0.8898	High Similarity	NPC241089
0.8889	High Similarity	NPC27490
0.888	High Similarity	NPC233056
0.888	High Similarity	NPC17840
0.888	High Similarity	NPC247477
0.888	High Similarity	NPC259942
0.8843	High Similarity	NPC218333
0.8833	High Similarity	NPC248363
0.8824	High Similarity	NPC195262
0.8824	High Similarity	NPC188814
0.8819	High Similarity	NPC267205
0.8819	High Similarity	NPC139074
0.8819	High Similarity	NPC48036
0.8819	High Similarity	NPC40524
0.8819	High Similarity	NPC213485
0.881	High Similarity	NPC324482
0.881	High Similarity	NPC475042
0.88	High Similarity	NPC120488
0.88	High Similarity	NPC102829
0.88	High Similarity	NPC476119
0.88	High Similarity	NPC230818
0.877	High Similarity	NPC306288
0.876	High Similarity	NPC475955
0.876	High Similarity	NPC474726
0.875	High Similarity	NPC282780
0.875	High Similarity	NPC166480
0.875	High Similarity	NPC475088
0.875	High Similarity	NPC474519
0.874	High Similarity	NPC135801
0.8739	High Similarity	NPC283844
0.873	High Similarity	NPC84772
0.873	High Similarity	NPC147757
0.873	High Similarity	NPC26697
0.873	High Similarity	NPC62219
0.872	High Similarity	NPC186098
0.872	High Similarity	NPC179898
0.872	High Similarity	NPC80694
0.871	High Similarity	NPC328983
0.871	High Similarity	NPC95309
0.8692	High Similarity	NPC213603
0.8682	High Similarity	NPC70859
0.8682	High Similarity	NPC144027
0.8682	High Similarity	NPC236974
0.8682	High Similarity	NPC283590
0.8682	High Similarity	NPC290803
0.8682	High Similarity	NPC61153
0.8682	High Similarity	NPC130899
0.8678	High Similarity	NPC229649
0.8672	High Similarity	NPC37299
0.8672	High Similarity	NPC180261
0.8672	High Similarity	NPC25937
0.8661	High Similarity	NPC469526
0.8661	High Similarity	NPC270369
0.8661	High Similarity	NPC219892
0.8661	High Similarity	NPC189823
0.8661	High Similarity	NPC275504
0.8661	High Similarity	NPC5515
0.8661	High Similarity	NPC34070
0.8661	High Similarity	NPC198249
0.864	High Similarity	NPC329205
0.864	High Similarity	NPC316625
0.8632	High Similarity	NPC223004
0.8615	High Similarity	NPC264112
0.8615	High Similarity	NPC194764
0.8615	High Similarity	NPC254847
0.8615	High Similarity	NPC191976
0.8615	High Similarity	NPC65005
0.8615	High Similarity	NPC84699
0.8605	High Similarity	NPC204960
0.8605	High Similarity	NPC294593
0.8605	High Similarity	NPC93756
0.8605	High Similarity	NPC159623
0.8605	High Similarity	NPC44437
0.8605	High Similarity	NPC144051
0.8605	High Similarity	NPC108113
0.8605	High Similarity	NPC82225
0.8605	High Similarity	NPC28753
0.8605	High Similarity	NPC18877
0.8605	High Similarity	NPC20560
0.8595	High Similarity	NPC294964
0.8594	High Similarity	NPC262359
0.8594	High Similarity	NPC313618
0.8594	High Similarity	NPC478190
0.8594	High Similarity	NPC475589
0.8594	High Similarity	NPC473584
0.8594	High Similarity	NPC31872
0.8583	High Similarity	NPC244441
0.8571	High Similarity	NPC470981
0.8571	High Similarity	NPC293453
0.8561	High Similarity	NPC470672
0.8561	High Similarity	NPC470671
0.8561	High Similarity	NPC162939
0.8561	High Similarity	NPC474487
0.8561	High Similarity	NPC474504
0.856	High Similarity	NPC473751
0.855	High Similarity	NPC65837
0.855	High Similarity	NPC470397
0.855	High Similarity	NPC290030
0.855	High Similarity	NPC53414
0.855	High Similarity	NPC149372
0.855	High Similarity	NPC187826
0.855	High Similarity	NPC53206
0.855	High Similarity	NPC474771
0.855	High Similarity	NPC470398
0.855	High Similarity	NPC471905
0.855	High Similarity	NPC156910
0.855	High Similarity	NPC474849
0.855	High Similarity	NPC178467
0.8538	High Similarity	NPC125920
0.8538	High Similarity	NPC470210
0.8538	High Similarity	NPC278375
0.8538	High Similarity	NPC164136
0.8538	High Similarity	NPC286336
0.8537	High Similarity	NPC232708
0.8537	High Similarity	NPC66252
0.8527	High Similarity	NPC153783
0.8527	High Similarity	NPC212631
0.8527	High Similarity	NPC205468
0.8527	High Similarity	NPC203817
0.8527	High Similarity	NPC10971
0.8527	High Similarity	NPC470988
0.8527	High Similarity	NPC129132
0.8527	High Similarity	NPC257756
0.8527	High Similarity	NPC285054
0.8527	High Similarity	NPC87231
0.8522	High Similarity	NPC224584
0.8496	Intermediate Similarity	NPC169452
0.8496	Intermediate Similarity	NPC477956
0.8496	Intermediate Similarity	NPC109232
0.8496	Intermediate Similarity	NPC181560
0.8485	Intermediate Similarity	NPC162680
0.8485	Intermediate Similarity	NPC7013
0.8485	Intermediate Similarity	NPC209560
0.8485	Intermediate Similarity	NPC116632
0.8485	Intermediate Similarity	NPC472403

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 NPC146642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	967
0.2-0.3	1635
0.3-0.4	2904
0.4-0.5	1880
0.5-0.6	1048
0.6-0.7	302
0.7-0.8	98
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.874	High Similarity	NPD943	Approved
0.8615	High Similarity	NPD1509	Clinical (unspecified phase)
0.8594	High Similarity	NPD1240	Approved
0.8473	Intermediate Similarity	NPD1510	Phase 2
0.8462	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1549	Phase 2
0.8116	Intermediate Similarity	NPD7390	Discontinued
0.8058	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD9266	Approved
0.8051	Intermediate Similarity	NPD74	Approved
0.8016	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD940	Approved
0.8	Intermediate Similarity	NPD846	Approved
0.7967	Intermediate Similarity	NPD9493	Approved
0.7966	Intermediate Similarity	NPD9264	Approved
0.7966	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD9267	Approved
0.7966	Intermediate Similarity	NPD9263	Approved
0.7953	Intermediate Similarity	NPD9269	Phase 2
0.792	Intermediate Similarity	NPD9268	Approved
0.792	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6651	Approved
0.7907	Intermediate Similarity	NPD1164	Approved
0.7907	Intermediate Similarity	NPD1470	Approved
0.7857	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD2800	Approved
0.7823	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1512	Approved
0.7737	Intermediate Similarity	NPD2796	Approved
0.7704	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD9545	Approved
0.7687	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1934	Approved
0.7661	Intermediate Similarity	NPD9281	Approved
0.7655	Intermediate Similarity	NPD4380	Phase 2
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD9261	Approved
0.7619	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1243	Approved
0.7552	Intermediate Similarity	NPD2532	Approved
0.7552	Intermediate Similarity	NPD2533	Approved
0.7552	Intermediate Similarity	NPD2534	Approved
0.7541	Intermediate Similarity	NPD4750	Phase 3
0.7538	Intermediate Similarity	NPD9717	Approved
0.7518	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD6799	Approved
0.7483	Intermediate Similarity	NPD7411	Suspended
0.7482	Intermediate Similarity	NPD5404	Approved
0.7482	Intermediate Similarity	NPD5406	Approved
0.7482	Intermediate Similarity	NPD5408	Approved
0.7482	Intermediate Similarity	NPD1551	Phase 2
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7482	Intermediate Similarity	NPD5405	Approved
0.7467	Intermediate Similarity	NPD7075	Discontinued
0.7447	Intermediate Similarity	NPD2654	Approved
0.7429	Intermediate Similarity	NPD2344	Approved
0.74	Intermediate Similarity	NPD3882	Suspended
0.7383	Intermediate Similarity	NPD7819	Suspended
0.7383	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1203	Approved
0.7351	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3749	Approved
0.7313	Intermediate Similarity	NPD2798	Approved
0.7311	Intermediate Similarity	NPD1242	Phase 1
0.7297	Intermediate Similarity	NPD6599	Discontinued
0.7286	Intermediate Similarity	NPD2799	Discontinued
0.7244	Intermediate Similarity	NPD7473	Discontinued
0.7234	Intermediate Similarity	NPD6099	Approved
0.7234	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2309	Approved
0.7211	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD6959	Discontinued
0.72	Intermediate Similarity	NPD6801	Discontinued
0.7197	Intermediate Similarity	NPD422	Phase 1
0.7179	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6166	Phase 2
0.7179	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7768	Phase 2
0.7163	Intermediate Similarity	NPD3748	Approved
0.7161	Intermediate Similarity	NPD6232	Discontinued
0.7105	Intermediate Similarity	NPD3817	Phase 2
0.7101	Intermediate Similarity	NPD411	Approved
0.7101	Intermediate Similarity	NPD3764	Approved
0.7083	Intermediate Similarity	NPD3020	Approved
0.7083	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD447	Suspended
0.7059	Intermediate Similarity	NPD288	Approved
0.7055	Intermediate Similarity	NPD3300	Phase 2
0.705	Intermediate Similarity	NPD520	Approved
0.7045	Intermediate Similarity	NPD2932	Approved
0.7045	Intermediate Similarity	NPD3019	Approved
0.7044	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7074	Phase 3
0.6981	Remote Similarity	NPD3818	Discontinued
0.6978	Remote Similarity	NPD2313	Discontinued
0.6978	Remote Similarity	NPD3268	Approved
0.6975	Remote Similarity	NPD2859	Approved
0.6975	Remote Similarity	NPD1809	Phase 2
0.6975	Remote Similarity	NPD2860	Approved
0.6975	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD844	Approved
0.6957	Remote Similarity	NPD5953	Discontinued
0.6949	Remote Similarity	NPD845	Approved
0.6948	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1610	Phase 2
0.6937	Remote Similarity	NPD6020	Phase 2
0.6937	Remote Similarity	NPD7054	Approved
0.6923	Remote Similarity	NPD5494	Approved
0.6923	Remote Similarity	NPD256	Approved
0.6923	Remote Similarity	NPD255	Approved
0.6894	Remote Similarity	NPD7472	Approved
0.6894	Remote Similarity	NPD1759	Phase 1
0.6891	Remote Similarity	NPD2934	Approved
0.6891	Remote Similarity	NPD2933	Approved
0.6889	Remote Similarity	NPD1608	Approved
0.6889	Remote Similarity	NPD3972	Approved
0.6885	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9494	Approved
0.6867	Remote Similarity	NPD5403	Approved
0.6861	Remote Similarity	NPD2797	Approved
0.6859	Remote Similarity	NPD919	Approved
0.6857	Remote Similarity	NPD1296	Phase 2
0.6855	Remote Similarity	NPD1237	Approved
0.6852	Remote Similarity	NPD6797	Phase 2
0.6846	Remote Similarity	NPD5401	Approved
0.6842	Remote Similarity	NPD111	Approved
0.6838	Remote Similarity	NPD1755	Approved
0.6835	Remote Similarity	NPD5710	Approved
0.6835	Remote Similarity	NPD5711	Approved
0.6835	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD4908	Phase 1
0.6832	Remote Similarity	NPD7286	Phase 2
0.6818	Remote Similarity	NPD1465	Phase 2
0.6818	Remote Similarity	NPD1758	Phase 1
0.6812	Remote Similarity	NPD1019	Discontinued
0.681	Remote Similarity	NPD7251	Discontinued
0.6806	Remote Similarity	NPD4308	Phase 3
0.6806	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4628	Phase 3
0.6788	Remote Similarity	NPD1876	Approved
0.6776	Remote Similarity	NPD3226	Approved
0.6772	Remote Similarity	NPD1247	Approved
0.6769	Remote Similarity	NPD1241	Discontinued
0.6768	Remote Similarity	NPD7808	Phase 3
0.6767	Remote Similarity	NPD1548	Phase 1
0.6755	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3267	Approved
0.6739	Remote Similarity	NPD3266	Approved
0.6738	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3021	Approved
0.6719	Remote Similarity	NPD3022	Approved
0.6715	Remote Similarity	NPD4749	Approved
0.6712	Remote Similarity	NPD2346	Discontinued
0.6707	Remote Similarity	NPD6559	Discontinued
0.6695	Remote Similarity	NPD9256	Approved
0.6695	Remote Similarity	NPD9258	Approved
0.6687	Remote Similarity	NPD1729	Discontinued
0.6687	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6646	Remote Similarity	NPD2403	Approved
0.6643	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1930	Approved
0.664	Remote Similarity	NPD1929	Approved
0.6637	Remote Similarity	NPD9093	Approved
0.6618	Remote Similarity	NPD3023	Approved
0.6618	Remote Similarity	NPD3026	Approved
0.6617	Remote Similarity	NPD9568	Approved
0.6599	Remote Similarity	NPD1471	Phase 3
0.6597	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3025	Approved
0.6593	Remote Similarity	NPD3024	Approved
0.6579	Remote Similarity	NPD9089	Approved
0.6577	Remote Similarity	NPD7003	Approved
0.6577	Remote Similarity	NPD3400	Discontinued
0.6577	Remote Similarity	NPD1196	Approved
0.6575	Remote Similarity	NPD7033	Discontinued
0.6571	Remote Similarity	NPD257	Approved
0.6571	Remote Similarity	NPD258	Approved
0.657	Remote Similarity	NPD4360	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data