NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	153.908
LogP:	2.15
LogD:	2.105
LogS:	-2.145
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	1.201
Fsp3:	0.222
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:	-4.385
MDCK Permeability:	2.3621176296728663e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.661
Plasma Protein Binding (PPB):	81.10181427001953%
Volume Distribution (VD):	0.645
Pgp-substrate:	21.39999771118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.877
CYP2C19-substrate:	0.521
CYP2C9-inhibitor:	0.364
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.733
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	5.498
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.745
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.178
Carcinogencity:	0.559
Eye Corrosion:	0.899
Eye Irritation:	0.994
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC145053

Natural Product ID:	NPC145053
*Common Name:**	1-(4-Methylphenyl)Ethanone
IUPAC Name:	1-(4-methylphenyl)ethanone
Synonyms:	1-P-Tolylethanone
Standard InCHIKey:	GNKZMNRKLCTJAY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3
SMILES:	Cc1ccc(cc1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL271871
PubChem CID:	8500
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]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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[TCMID]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	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]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12700	Diospyros eriantha	Species	Ebenaceae	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]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	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]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13671	Ononis vaginalis	Species	Fabaceae	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]

☑ 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
Others	6
Potency	3

Activity Type	# Activity
Individual Protein	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Km	=	27710000.0	nM	PMID[524854]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Vmax	=	0.2	micromol/min	PMID[524854]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Ratio	=	7.21	uL/min	PMID[524854]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Km	=	13200000.0	nM	PMID[524854]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Ratio	=	1.01	uL/min	PMID[524854]
NPT590	Individual Protein	3-alpha-hydroxysteroid dehydrogenase	Rattus norvegicus	Vmax	=	0.013	micromol/min	PMID[524854]
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10870.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC145053 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	385
0.1-0.2	2584
0.2-0.3	7449
0.3-0.4	15135
0.4-0.5	12295
0.5-0.6	3975
0.6-0.7	666
0.7-0.8	120
0.8-0.85	33
0.85-0.9	36
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC190567
0.96	High Similarity	NPC285470
0.96	High Similarity	NPC36342
0.96	High Similarity	NPC2785
0.9474	High Similarity	NPC300205
0.9467	High Similarity	NPC245966
0.9375	High Similarity	NPC307
0.9375	High Similarity	NPC160339
0.9351	High Similarity	NPC164086
0.9259	High Similarity	NPC69057
0.9241	High Similarity	NPC197581
0.9231	High Similarity	NPC12936
0.9231	High Similarity	NPC273033
0.9103	High Similarity	NPC285716
0.9103	High Similarity	NPC17408
0.9103	High Similarity	NPC71664
0.9012	High Similarity	NPC252067
0.9	High Similarity	NPC273758
0.8987	High Similarity	NPC100039
0.8933	High Similarity	NPC285679
0.8929	High Similarity	NPC277277
0.8929	High Similarity	NPC173413
0.8916	High Similarity	NPC157778
0.8846	High Similarity	NPC103488
0.8824	High Similarity	NPC133461
0.88	High Similarity	NPC74458
0.8795	High Similarity	NPC43945
0.875	High Similarity	NPC73978
0.8721	High Similarity	NPC155232
0.8721	High Similarity	NPC153885
0.869	High Similarity	NPC267262
0.869	High Similarity	NPC153308
0.8625	High Similarity	NPC95868
0.8621	High Similarity	NPC238219
0.8621	High Similarity	NPC289883
0.8605	High Similarity	NPC284475
0.8537	High Similarity	NPC149263
0.8537	High Similarity	NPC215008
0.8537	High Similarity	NPC324624
0.8537	High Similarity	NPC39600
0.8533	High Similarity	NPC98880
0.8523	High Similarity	NPC260233
0.8506	High Similarity	NPC59677
0.8506	High Similarity	NPC188844
0.8506	High Similarity	NPC1682
0.8506	High Similarity	NPC323420
0.85	High Similarity	NPC139901
0.85	High Similarity	NPC151405
0.8488	Intermediate Similarity	NPC19256
0.8488	Intermediate Similarity	NPC58872
0.8452	Intermediate Similarity	NPC164526
0.8427	Intermediate Similarity	NPC219573
0.8427	Intermediate Similarity	NPC185208
0.8421	Intermediate Similarity	NPC95289
0.84	Intermediate Similarity	NPC311343
0.8375	Intermediate Similarity	NPC76455
0.8375	Intermediate Similarity	NPC137847
0.8372	Intermediate Similarity	NPC418308
0.8372	Intermediate Similarity	NPC113307
0.8354	Intermediate Similarity	NPC78500
0.8333	Intermediate Similarity	NPC239185
0.8256	Intermediate Similarity	NPC473345
0.825	Intermediate Similarity	NPC9796
0.825	Intermediate Similarity	NPC329318
0.8242	Intermediate Similarity	NPC75724
0.8242	Intermediate Similarity	NPC49994
0.8242	Intermediate Similarity	NPC134882
0.8182	Intermediate Similarity	NPC103346
0.8171	Intermediate Similarity	NPC157055
0.8132	Intermediate Similarity	NPC265220
0.8111	Intermediate Similarity	NPC472880
0.8101	Intermediate Similarity	NPC208075
0.8065	Intermediate Similarity	NPC109514
0.8065	Intermediate Similarity	NPC476993
0.8049	Intermediate Similarity	NPC272260
0.8025	Intermediate Similarity	NPC298023
0.8	Intermediate Similarity	NPC246757
0.8	Intermediate Similarity	NPC291070
0.7979	Intermediate Similarity	NPC25458
0.7976	Intermediate Similarity	NPC230068
0.7975	Intermediate Similarity	NPC271437
0.7955	Intermediate Similarity	NPC325709
0.7952	Intermediate Similarity	NPC477703
0.7895	Intermediate Similarity	NPC247976
0.7872	Intermediate Similarity	NPC472879
0.7865	Intermediate Similarity	NPC303967
0.7865	Intermediate Similarity	NPC110420
0.7865	Intermediate Similarity	NPC67585
0.7848	Intermediate Similarity	NPC326200
0.7805	Intermediate Similarity	NPC179726
0.7778	Intermediate Similarity	NPC110704
0.7766	Intermediate Similarity	NPC217621
0.7753	Intermediate Similarity	NPC298115
0.7742	Intermediate Similarity	NPC240042
0.7732	Intermediate Similarity	NPC474910
0.7732	Intermediate Similarity	NPC172483
0.7708	Intermediate Similarity	NPC474866
0.7708	Intermediate Similarity	NPC472691
0.7708	Intermediate Similarity	NPC471829
0.7708	Intermediate Similarity	NPC274443
0.7708	Intermediate Similarity	NPC475939
0.7701	Intermediate Similarity	NPC123476
0.7653	Intermediate Similarity	NPC100767
0.7629	Intermediate Similarity	NPC329282
0.7604	Intermediate Similarity	NPC222390
0.7604	Intermediate Similarity	NPC244427
0.7604	Intermediate Similarity	NPC304873
0.76	Intermediate Similarity	NPC54368
0.76	Intermediate Similarity	NPC248705
0.7595	Intermediate Similarity	NPC169222
0.7595	Intermediate Similarity	NPC235059
0.7595	Intermediate Similarity	NPC16190
0.7582	Intermediate Similarity	NPC476484
0.7553	Intermediate Similarity	NPC253423
0.7526	Intermediate Similarity	NPC329556
0.75	Intermediate Similarity	NPC112552
0.75	Intermediate Similarity	NPC470252
0.75	Intermediate Similarity	NPC50192
0.75	Intermediate Similarity	NPC473325
0.75	Intermediate Similarity	NPC95965
0.7475	Intermediate Similarity	NPC472700
0.7475	Intermediate Similarity	NPC472699
0.7473	Intermediate Similarity	NPC86670
0.7473	Intermediate Similarity	NPC274455
0.7473	Intermediate Similarity	NPC70940
0.7471	Intermediate Similarity	NPC288903
0.7447	Intermediate Similarity	NPC12695
0.7444	Intermediate Similarity	NPC477693
0.7444	Intermediate Similarity	NPC477704
0.7416	Intermediate Similarity	NPC318107
0.7403	Intermediate Similarity	NPC88566
0.74	Intermediate Similarity	NPC472695
0.74	Intermediate Similarity	NPC472701
0.74	Intermediate Similarity	NPC472696
0.74	Intermediate Similarity	NPC472683
0.7396	Intermediate Similarity	NPC203925
0.7374	Intermediate Similarity	NPC105899
0.7374	Intermediate Similarity	NPC167336
0.7368	Intermediate Similarity	NPC156021
0.7363	Intermediate Similarity	NPC231591
0.7353	Intermediate Similarity	NPC265513
0.7353	Intermediate Similarity	NPC474057
0.734	Intermediate Similarity	NPC130398
0.7333	Intermediate Similarity	NPC194326
0.7333	Intermediate Similarity	NPC8235
0.7333	Intermediate Similarity	NPC322387
0.7327	Intermediate Similarity	NPC192577
0.7326	Intermediate Similarity	NPC127343
0.732	Intermediate Similarity	NPC70624
0.7312	Intermediate Similarity	NPC77273
0.7308	Intermediate Similarity	NPC198023
0.7303	Intermediate Similarity	NPC294134
0.73	Intermediate Similarity	NPC185763
0.73	Intermediate Similarity	NPC37914
0.73	Intermediate Similarity	NPC83409
0.7292	Intermediate Similarity	NPC145052
0.7292	Intermediate Similarity	NPC229242
0.7282	Intermediate Similarity	NPC280789
0.7282	Intermediate Similarity	NPC292834
0.7273	Intermediate Similarity	NPC285773
0.7273	Intermediate Similarity	NPC249067
0.7273	Intermediate Similarity	NPC44830
0.7263	Intermediate Similarity	NPC61944
0.7253	Intermediate Similarity	NPC329064
0.7245	Intermediate Similarity	NPC188895
0.7234	Intermediate Similarity	NPC34243
0.7234	Intermediate Similarity	NPC261181
0.7228	Intermediate Similarity	NPC249811
0.7228	Intermediate Similarity	NPC112903
0.7228	Intermediate Similarity	NPC203732
0.7216	Intermediate Similarity	NPC325497
0.7215	Intermediate Similarity	NPC178527
0.7212	Intermediate Similarity	NPC93287
0.7212	Intermediate Similarity	NPC470253
0.7204	Intermediate Similarity	NPC125226
0.72	Intermediate Similarity	NPC134120
0.72	Intermediate Similarity	NPC300345
0.72	Intermediate Similarity	NPC120441
0.72	Intermediate Similarity	NPC212114
0.72	Intermediate Similarity	NPC65873
0.7188	Intermediate Similarity	NPC92754
0.7188	Intermediate Similarity	NPC249912
0.7188	Intermediate Similarity	NPC103048
0.7188	Intermediate Similarity	NPC276775
0.7184	Intermediate Similarity	NPC137315
0.7176	Intermediate Similarity	NPC3672
0.7176	Intermediate Similarity	NPC287790
0.7172	Intermediate Similarity	NPC301943
0.7172	Intermediate Similarity	NPC474365
0.7143	Intermediate Similarity	NPC210849
0.7143	Intermediate Similarity	NPC471721
0.7143	Intermediate Similarity	NPC206800
0.7143	Intermediate Similarity	NPC135924
0.7143	Intermediate Similarity	NPC67377
0.7143	Intermediate Similarity	NPC150196
0.7143	Intermediate Similarity	NPC32203
0.7143	Intermediate Similarity	NPC326664
0.7129	Intermediate Similarity	NPC6984
0.7125	Intermediate Similarity	NPC6107
0.7125	Intermediate Similarity	NPC267443

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 NPC145053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1065
0.2-0.3	1808
0.3-0.4	3397
0.4-0.5	1770
0.5-0.6	579
0.6-0.7	97
0.7-0.8	40
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD942	Approved
0.8795	High Similarity	NPD650	Approved
0.8625	High Similarity	NPD1507	Clinical (unspecified phase)
0.8605	High Similarity	NPD7609	Phase 3
0.8571	High Similarity	NPD506	Clinical (unspecified phase)
0.8506	High Similarity	NPD7631	Approved
0.8333	Intermediate Similarity	NPD3495	Discontinued
0.809	Intermediate Similarity	NPD1508	Approved
0.7979	Intermediate Similarity	NPD2193	Phase 2
0.7979	Intermediate Similarity	NPD2196	Discontinued
0.7979	Intermediate Similarity	NPD2648	Phase 3
0.7826	Intermediate Similarity	NPD1843	Approved
0.7789	Intermediate Similarity	NPD1932	Approved
0.7766	Intermediate Similarity	NPD2066	Phase 3
0.7742	Intermediate Similarity	NPD1100	Approved
0.7742	Intermediate Similarity	NPD1099	Approved
0.7732	Intermediate Similarity	NPD1677	Discontinued
0.7732	Intermediate Similarity	NPD2192	Approved
0.7732	Intermediate Similarity	NPD2197	Approved
0.7727	Intermediate Similarity	NPD1087	Approved
0.7556	Intermediate Similarity	NPD800	Approved
0.7527	Intermediate Similarity	NPD1693	Approved
0.7526	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1930	Approved
0.7526	Intermediate Similarity	NPD1929	Approved
0.75	Intermediate Similarity	NPD225	Approved
0.75	Intermediate Similarity	NPD2329	Discontinued
0.75	Intermediate Similarity	NPD227	Approved
0.7473	Intermediate Similarity	NPD1090	Approved
0.7473	Intermediate Similarity	NPD1089	Approved
0.7473	Intermediate Similarity	NPD1086	Approved
0.7426	Intermediate Similarity	NPD1317	Discontinued
0.7423	Intermediate Similarity	NPD2171	Approved
0.7419	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD9259	Approved
0.7416	Intermediate Similarity	NPD9257	Approved
0.7412	Intermediate Similarity	NPD9490	Approved
0.7353	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1088	Approved
0.7273	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9491	Approved
0.7273	Intermediate Similarity	NPD1237	Approved
0.7241	Intermediate Similarity	NPD226	Approved
0.7234	Intermediate Similarity	NPD1202	Approved
0.7234	Intermediate Similarity	NPD1563	Approved
0.7204	Intermediate Similarity	NPD1239	Approved
0.7158	Intermediate Similarity	NPD4094	Approved
0.7143	Intermediate Similarity	NPD9716	Approved
0.7115	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9256	Approved
0.7097	Intermediate Similarity	NPD9258	Approved
0.7083	Intermediate Similarity	NPD1989	Approved
0.7071	Intermediate Similarity	NPD813	Approved
0.701	Intermediate Similarity	NPD1564	Approved
0.701	Intermediate Similarity	NPD1565	Approved
0.701	Intermediate Similarity	NPD4657	Approved
0.701	Intermediate Similarity	NPD4655	Approved
0.701	Intermediate Similarity	NPD1566	Phase 3
0.6989	Remote Similarity	NPD5347	Phase 2
0.6989	Remote Similarity	NPD5346	Phase 2
0.6957	Remote Similarity	NPD4793	Discontinued
0.6931	Remote Similarity	NPD164	Approved
0.6915	Remote Similarity	NPD3672	Approved
0.6915	Remote Similarity	NPD3673	Approved
0.6881	Remote Similarity	NPD7610	Discontinued
0.6869	Remote Similarity	NPD1238	Approved
0.6857	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1007	Discontinued
0.6832	Remote Similarity	NPD3357	Discontinued
0.6827	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7009	Phase 2
0.6804	Remote Similarity	NPD9260	Approved
0.6762	Remote Similarity	NPD664	Approved
0.6759	Remote Similarity	NPD1246	Approved
0.6759	Remote Similarity	NPD5951	Approved
0.6757	Remote Similarity	NPD1245	Approved
0.675	Remote Similarity	NPD675	Discontinued
0.6739	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6027	Approved
0.6733	Remote Similarity	NPD6024	Approved
0.6703	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD7076	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD7077	Approved
0.6637	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1075	Approved
0.6606	Remote Similarity	NPD1074	Approved
0.6606	Remote Similarity	NPD1073	Approved
0.6602	Remote Similarity	NPD5909	Discontinued
0.66	Remote Similarity	NPD466	Approved
0.6579	Remote Similarity	NPD6287	Discontinued
0.6549	Remote Similarity	NPD5836	Discontinued
0.6535	Remote Similarity	NPD742	Approved
0.6522	Remote Similarity	NPD3972	Approved
0.6505	Remote Similarity	NPD9261	Approved
0.6505	Remote Similarity	NPD6647	Phase 2
0.6481	Remote Similarity	NPD9508	Approved
0.6471	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6049	Phase 2
0.6465	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD851	Approved
0.6455	Remote Similarity	NPD853	Approved
0.6436	Remote Similarity	NPD9495	Approved
0.6422	Remote Similarity	NPD6858	Approved
0.6422	Remote Similarity	NPD7094	Approved
0.6421	Remote Similarity	NPD1282	Approved
0.641	Remote Similarity	NPD2056	Discontinued
0.6408	Remote Similarity	NPD4803	Discontinued
0.6404	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2345	Approved
0.6395	Remote Similarity	NPD292	Approved
0.6395	Remote Similarity	NPD294	Approved
0.6364	Remote Similarity	NPD1241	Discontinued
0.6353	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4879	Approved
0.6316	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2067	Discontinued
0.6283	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD253	Approved
0.6273	Remote Similarity	NPD5277	Phase 2
0.6271	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD9264	Approved
0.6262	Remote Similarity	NPD9267	Approved
0.6262	Remote Similarity	NPD9263	Approved
0.6261	Remote Similarity	NPD1727	Approved
0.6239	Remote Similarity	NPD4878	Approved
0.6238	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1766	Approved
0.6226	Remote Similarity	NPD1765	Approved
0.6226	Remote Similarity	NPD1761	Approved
0.6226	Remote Similarity	NPD1767	Approved
0.6226	Remote Similarity	NPD1018	Approved
0.6226	Remote Similarity	NPD1763	Approved
0.6214	Remote Similarity	NPD7798	Approved
0.6214	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD74	Approved
0.6204	Remote Similarity	NPD9266	Approved
0.6195	Remote Similarity	NPD9493	Approved
0.6195	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5157	Phase 1
0.6186	Remote Similarity	NPD1101	Approved
0.6186	Remote Similarity	NPD5159	Phase 2
0.6186	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD9566	Approved
0.6163	Remote Similarity	NPD1673	Approved
0.6154	Remote Similarity	NPD1201	Approved
0.6154	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD2754	Discontinued
0.6147	Remote Similarity	NPD3581	Discontinued
0.6134	Remote Similarity	NPD1876	Approved
0.6126	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4733	Approved
0.6117	Remote Similarity	NPD5926	Approved
0.6106	Remote Similarity	NPD1323	Discontinued
0.6106	Remote Similarity	NPD1025	Discontinued
0.6106	Remote Similarity	NPD3317	Approved
0.6102	Remote Similarity	NPD3356	Approved
0.6102	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3355	Approved
0.6087	Remote Similarity	NPD9545	Approved
0.6083	Remote Similarity	NPD5653	Discontinued
0.6083	Remote Similarity	NPD1470	Approved
0.6075	Remote Similarity	NPD5048	Discontinued
0.6071	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1175	Approved
0.6067	Remote Similarity	NPD9588	Approved
0.6067	Remote Similarity	NPD9594	Approved
0.6067	Remote Similarity	NPD9589	Approved
0.6067	Remote Similarity	NPD80	Approved
0.6067	Remote Similarity	NPD9590	Approved
0.6067	Remote Similarity	NPD9591	Approved
0.6067	Remote Similarity	NPD9593	Approved
0.6067	Remote Similarity	NPD9592	Approved
0.6048	Remote Similarity	NPD7713	Phase 3
0.6048	Remote Similarity	NPD7961	Discontinued
0.604	Remote Similarity	NPD1066	Discontinued
0.6034	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2798	Approved
0.6019	Remote Similarity	NPD467	Phase 1
0.6018	Remote Similarity	NPD1022	Approved
0.6018	Remote Similarity	NPD1020	Approved
0.6018	Remote Similarity	NPD2508	Discontinued
0.6018	Remote Similarity	NPD2319	Discontinued
0.6018	Remote Similarity	NPD1021	Approved
0.6018	Remote Similarity	NPD1023	Approved
0.6016	Remote Similarity	NPD1190	Approved
0.6016	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7008	Discontinued
0.6	Remote Similarity	NPD1752	Approved
0.6	Remote Similarity	NPD4233	Approved
0.6	Remote Similarity	NPD1574	Approved
0.6	Remote Similarity	NPD1756	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