Compounds > bedaquiline

Page last updated: 2024-08-01 18:28:04

bedaquiline

Description

bedaquiline: a diarylquinoline Antitubercular Agent [MeSH]

bedaquiline : A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria. [CHeBI]

Cross-References

ID Source	ID
PubMed CID	5388906
CHEMBL ID	376488
SCHEMBL ID	295482
CHEBI ID	72292
MeSH ID	M0492968

Synonyms (75)

Synonym
bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol
3-quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphar,betas)-rel-
r-207910
1-(1r)-(6-bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(2s)-(naphthalen-1-yl)-1-phenyl-butan-2-ol
bedaquiline
(1r,2s)-1-(6-bromo-2-methoxy-3-quinolyl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenyl-butan-2-ol
843663-66-1
r 207910
r207910 ,
tmc207
(1r,2s)-1-(6-bromo-2-methoxy-quinolin-3-yl)-4-methyl-amino-2-naphthalen-1-yl-1-phenyl-butan-2-ol
bdq ,
tmc-207
chebi:72292 ,
CHEMBL376488
(1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
D09872
bedaquiline (usan/inn)
hsdb 8217
3-quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphas,betar)-
aids 222089
aids-222089
78846i289y ,
tmc 207
1-(6-bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol
bedaquiline [usan:inn]
unii-78846i289y
bedaquilinum
bedaquilina
(1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol
NCGC00348215-01
S5623
(1r)-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2(s)-(1-naphthyl)-1-phenylbutan-2-ol
bedaquiline [inn]
bedaquiline [mi]
DB08903
bedaquiline [who-dd]
3-quinolineethanol, 6-bromo-.alpha.-(2-(dimethylamino)ethyl)-2-methoxy-.alpha.-1-naphthalenyl-.beta.-phenyl-, (.alpha.s,.beta.r)-
bedaquiline [usan]
(1r,2s) 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-(1-naphthyl)-beta-phenyl-3-quinolineethanol
(1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1- phenylbutan-2-ol
bedaquiline [vandf]
HY-14881
SCHEMBL295482
AKOS022186476
(1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
J-500265
bq1 ,
AC-28385
(\|as,\|ar)-bedaquiline
bdbm50063995
gtpl11171
compound 1a [pmid: 17496888]
(alphas,betar)-6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
NCGC00348215-04
mmv689758
r403323; tmc207; r207910
c32h31brn2o2
DTXSID80903989 ,
(1r,2s)-1-(6-bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(3-fluorophenyl)-1-phenyl-butan-2-ol
Q1257318
CCG-270030
NCGC00348215-03
EX-A4133
(1r,2s)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol
843663-66-1 (free base)
SR-05000022473-1
sr-05000022473
rel-(1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
DTXSID101027810
compound 1a (pmid: 17496888)
1-(6-bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(3-fluorophenyl)-1-phenyl-butan-2-ol
3-quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alpha-s,beta-r)-
dtxcid501331924
j04ak05

Roles (2)

Role	Description
antitubercular agent	A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ATP synthase inhibitor	A mitochondrial respiratory-chain inhibitor that interferes with the action of ATP synthase.

Drug Classes (6)

Class	Description
quinolines	A class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
naphthalenes	Any benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
organobromine compound	A compound containing at least one carbon-bromine bond.
aromatic ether	Any ether in which the oxygen is attached to at least one aryl substituent.
tertiary alcohol	A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
tertiary amino compound	A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.

Protein Targets (18)

Potency Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4	Homo sapiens (human)	Potency	18.9991	AID1645841
G	Vesicular stomatitis virus	Potency	3.7908	AID1645842
cytochrome P450 2D6	Homo sapiens (human)	Potency	7.5637	AID1645840
Interferon beta	Homo sapiens (human)	Potency	3.7908	AID1645842
HLA class I histocompatibility antigen, B alpha chain	Homo sapiens (human)	Potency	3.7908	AID1645842
Spike glycoprotein	Severe acute respiratory syndrome-related coronavirus	Potency	39.8107	AID1479145
Inositol hexakisphosphate kinase 1	Homo sapiens (human)	Potency	3.7908	AID1645842
cytochrome P450 2C9, partial	Homo sapiens (human)	Potency	3.7908	AID1645842

Inhibition Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
Cytochrome P450 1A2	Homo sapiens (human)	IC50	10.0000	AID1861201
Cytochrome P450 3A4	Homo sapiens (human)	IC50	35.0000	AID1367752; AID1638959; AID1639007; AID1861205
Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	IC50	4.3600	AID1640021
Cytochrome P450 2D6	Homo sapiens (human)	IC50	10.0000	AID1861204
Cytochrome P450 2C9	Homo sapiens (human)	IC50	10.0000	AID1861202
Cytochrome P450 2C19	Homo sapiens (human)	IC50	5.8000	AID1389805; AID1861203
Potassium voltage-gated channel subfamily H member 2	Homo sapiens (human)	IC50	4.8425	AID1367747; AID1389805; AID1389808; AID1503834; AID1638948; AID1639008; AID1650508; AID1861206
ATP synthase subunit c	Mycolicibacterium smegmatis	IC50	0.0119	AID502989; AID544553; AID544555
Sigma intracellular receptor 2	Rattus norvegicus (Norway rat)	IC50	1.6000	AID1389805

Activation Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
ATP synthase subunit c	Bacillus sp. PS3	Kd	0.5000	AID503001
Potassium voltage-gated channel subfamily H member 2	Homo sapiens (human)	EC50	15.0000	AID1726775

Bioassays (446)

Assay ID	Title	Year	Journal	Article
AID502972	Antimicrobial activity against Mycobacterium tuberculosis by alamar blue assay	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1650518	Protein binding in human plasma	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID503006	Binding affinity to Bacillus PS3 ATP synthase subunit beta by mass spectroscopy	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1900066	AUC in mouse at 100 mg/kg, po administered as single dose	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID1900064	Intrinsic clearance in mouse liver microsomes	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID529105	Cardiotoxicity in pulmonary tuberculosis patient assessed as increase in QT interval at 400 mg/kg, po once daily for 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1639015	AUC (0 to infinity) in po dosed mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID502980	Ratio of MIC for Mycobacterium tuberculosis H37Rv isolate LV13 expressing ATP synthase atpE I66M mutant protein to MIC for Mycobacterium tuberculosis H37Rv	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1503834	Inhibition of human ERG	2017	ACS medicinal chemistry letters, Oct-12, Volume: 8, Issue:10 ISSN: 1948-5875
AID1861199	Microsomal stability in rat liver microsomes assessed as clearance	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1483726	Inhibition of oxygen consumption in Mycobacterium smegmatis inverted membrane vesicles lacking cytochrome bc1 complex treated between 250 to 450 secs post NADH addition	2017	Journal of medicinal chemistry, 02-23, Volume: 60, Issue:4 ISSN: 1520-4804	Discovery of Imidazo[1,2-a]pyridine Ethers and Squaramides as Selective and Potent Inhibitors of Mycobacterial Adenosine Triphosphate (ATP) Synthesis.
AID283244	Reduction of lung lesions in Mycobacterium tuberculosis H37Rv infected Swiss mouse at 25 mg/kg, po for 5 days/week after 2 months	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3 ISSN: 0066-4804	Synergistic activity of R207910 combined with pyrazinamide against murine tuberculosis.
AID1154327	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID544557	Inhibition of human ATP synthase mediated ATP production at 100 nM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID565299	Antitubercular activity against Mycobacterium avium infected in C57BL/6J mouse assessed as reduction of CFU counts in spleen at 200 mg/kg, po administered one month post-infection five times weekly for 2 months (Rvb = 9.4 +/- 0.2 log10CFU)	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID1389804	Inhibition of CYP3A4 in human liver microsomes after 20 mins	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1194570	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv expressing Lux assessed as reduction in growth measured after 3 weeks by bioluminescence assay	2015	Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9 ISSN: 1464-3391	Design and synthesis of novel anti-tuberculosis agents from the celecoxib pharmacophore.
AID698993	Cmax in human at 10 mg, po	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID529093	Steady-state plasma concentration in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID528932	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 2 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID525522	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 5 expressing wild type atpE Ile66Met mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1861226	Drug concentration in CD-1 mouse plasma at 6.25 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID528931	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 1 day	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID544545	Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID528965	Drug uptake in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID562292	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1367750	Growth inhibition of Mycobacterium tuberculosis H37Rv under aerobic condition after 4 days by MABA method	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID528928	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 5 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1181170	Antimicrobial activity against second mutant generation Mycobacterium tuberculosis 1024_8.12 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID528926	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 3 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID372788	Antimicrobial activity against Mycobacterium intracellular 14 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1861227	Ratio of drug concentration in CD-1 mouse lung to plasma at 6.25 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1888139	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis clinical isolate HD5 assessed as inhibition of bacterial growth incubated for 7 days by by microplate alamar blue assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254	Exploring disordered loops in DprE1 provides a functional site to combat drug-resistance in Mycobacterium strains.
AID780666	Antitubercular activity against Mycobacterium tuberculosis H37Rv assessed as parasite growth inhibition	2013	Bioorganic & medicinal chemistry letters, Nov-15, Volume: 23, Issue:22 ISSN: 1464-3405	Rational drug design based synthesis of novel arylquinolines as anti-tuberculosis agents.
AID1698409	Inhibition of human ATPsynthase	2020	Bioorganic & medicinal chemistry, 11-15, Volume: 28, Issue:22 ISSN: 1464-3391	Synthesis and structure-activity relationships for tetrahydroisoquinoline-based inhibitors of Mycobacterium tuberculosis.
AID372662	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1367748	Intrinsic clearance in human liver microsomes at 1 mg/ml after 60 mins	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID1726777	Antitubercular activity against Mycobacterium tuberculosis H37Rv by broth microdilution method	2021	RSC medicinal chemistry, Jun-23, Volume: 12, Issue:6 ISSN: 2632-8682	Synthesis and evaluation of pyridine-derived bedaquiline analogues containing modifications at the A-ring subunit.
AID562285	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 6 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID698990	AUC at steady state (0 to 24 hrs) in human at 400 mg, po qd for 14 days	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1389810	Antitubercular activity against Mycobacterium tuberculosis Erdman infected in BALB/c mouse assessed as reduction in bacterial burden in lungs at 20 mg/kg, po qd for 12 continuous days from day 11 post infection measured on day 25 relative to 10 mg/kg beda	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1639013	Clearance in iv dosed mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID529099	Toxicity in pulmonary tuberculosis patient assessed as rash at 100 mg/kg, po once daily	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1265239	Antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 27294 after 5 days	2015	European journal of medicinal chemistry, Dec-01, Volume: 106ISSN: 1768-3254	Structure activity relationships of 4-hydroxy-2-pyridones: A novel class of antituberculosis agents.
AID1580694	Inhibition of ATP-synthase (unknown origin)	2019	Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23 ISSN: 1520-4804	Changing the Rules of TB-Drug Discovery.
AID1861212	Oral bioavailability in mouse at 6.25 mg/kg	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1861215	Half life in Sprague-Dawley rat at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID562298	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 6 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1639007	Inhibition of CYP3A4 (unknown origin)	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1650520	Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 72 hrs by MTS-PBS assay	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID372803	Antimicrobial activity against Mycobacterium conspicuum after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID739412	Antitubercular activity against Mycobacterium tuberculosis H37Rv	2013	Journal of medicinal chemistry, May-23, Volume: 56, Issue:10 ISSN: 1520-4804	Preliminary structure-activity relationships and biological evaluation of novel antitubercular indolecarboxamide derivatives against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains.
AID503001	Binding affinity to Bacillus PS3 ATP synthase subunit c	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1900065	Intrinsic clearance in human liver microsomes	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID562468	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 100 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 302 t	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861204	Inhibition of CYP2D6 (unknown origin)	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372805	Antimicrobial activity against Mycobacterium xenopi after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID562470	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 120 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 302	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID562290	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1883682	Potency index, ratio of Suda-pyridine MIC90 to test compound MIC90 for antibacterial activity against Mycobacterium tuberculosis H37Rv assessed as inhibition of bacterial growth	2022	Journal of medicinal chemistry, 06-09, Volume: 65, Issue:11 ISSN: 1520-4804	Tuberculosis Drug Discovery: Challenges and New Horizons.
AID1650506	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as bacterial growth inhibition under replicating, aerobic condition by microplate Alamar blue assay	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID502986	Antimicrobial activity against Mycobacterium smegmatis expressing ATP synthase AtpE D32V mutant protein by 7H9 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1603257	Antibacterial activity against INH-resistant Mycobacterium tuberculosis after 7 days by microplate alamar blue assay	2019	ACS medicinal chemistry letters, Mar-14, Volume: 10, Issue:3 ISSN: 1948-5875
AID502975	Antimicrobial activity against Mycobacterium tuberculosis H37Rv isolate LV13 expressing ATP synthase atpE I66M mutant protein by 7H9 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID565301	Antimicrobial activity against Mycobacterium avium	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID544541	Antimicrobial activity against Mycobacterium tuberculosis	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID565298	Antitubercular activity against Mycobacterium avium infected in C57BL/6J mouse assessed as reduction of CFU counts in spleen at 25 mg/kg, po administered one month post-infection five times weekly for 1 month (Rvb = 7.4 +/- 1.7 log10CFU)	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID562307	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 100 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1367749	Half life in human liver microsomes	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID1659808	Antimycobacterial activity against Mycobacterium smegmatis	2020	Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17 ISSN: 1520-4804	Molecule Property Analyses of Active Compounds for
AID372661	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID528933	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 3 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID528942	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 5 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID529097	Toxicity in pulmonary tuberculosis patient assessed as hemoptysis at 400 mg/kg, po once daily	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1389806	Intrinsic clearance in human liver microsomes at 1 uM after 60 mins	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1650516	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv infected in BALB/c mouse model of acute infection assessed as log reduction in bacterial burden in lung at 20 mg/kg, po via gavage administered as single dose for 12 days starting from 10	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1861187	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as mycobacterial growth inhibition by microplate alamar blue assay	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID502989	Inhibition of Mycobacterium smegmatis ATCC 607 ATP synthase subunit c-mediated ATP synthesis after 60 mins by luminometry	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID529080	Drug uptake in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID544563	Inhibition of ATP synthase in bovine heart mitochondria assessed as effect on oxygen consumption at 175 uM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID669834	Antibacterial activity against Mycobacterium tuberculosis H37Rv ATCC 27294 by microplate alamar blue assay	2012	Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8 ISSN: 1520-4804	Discovery of selective menaquinone biosynthesis inhibitors against Mycobacterium tuberculosis.
AID562287	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1181171	Antimicrobial activity against second mutant generation Mycobacterium tuberculosis 1024_16.5 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID1821091	Antibacterial activity against Mycobacterium tuberculosis mc2 6230 assessed as bacterial growth inhibition incubated for 5 days by resazurin microtiter assay	2022	Journal of natural products, 01-28, Volume: 85, Issue:1 ISSN: 1520-6025
AID502984	Ratio of MIC for Mycobacterium smegmatis isolate R09 expressing ATP synthase AtpE D32V mutant protein to MIC for wild type Mycobacterium smegmatis	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID581002	Antimicrobial activity against compound-susceptible Mycobacterium tuberculosis	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	New drugs against tuberculosis: problems, progress, and evaluation of agents in clinical development.
AID1861193	Apparent permeability across apical side to basolateral side in dog MDCK cells	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1639009	Aqueous solubility of the compound at pH 7.4	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID502973	Antimicrobial activity against Mycobacterium bovis BCG by alamar blue assay	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1888135	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis clinical isolate HD1 assessed as inhibition of bacterial growth incubated for 7 days by by microplate alamar blue assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254	Exploring disordered loops in DprE1 provides a functional site to combat drug-resistance in Mycobacterium strains.
AID529083	Cmin in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID525531	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 2 expressing atpE Glu61Asp mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID502971	Antimicrobial activity against Mycobacterium smegmatis ATCC 607 by alamar blue assay	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID525520	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis H37Rv expressing wild type atpE Ala63Pro mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID529091	AUC (0 to 24 hrs) in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID562306	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID581000	Tmax in human	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	New drugs against tuberculosis: problems, progress, and evaluation of agents in clinical development.
AID528959	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured on day 8 after starting standard TB therapy	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID372779	Antimicrobial activity against Mycobacterium avium 6 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1639014	Apparent volume of distribution during terminal phase in iv dosed mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID604585	Antimicrobial activity against Mycobacterium tuberculosis H37Rv ATCC 27294 after 16 to 24 hrs by microplate alamar blue assay	2011	European journal of medicinal chemistry, Apr, Volume: 46, Issue:4 ISSN: 1768-3254	Synthesis and antimycobacterial activity of prodrugs of indeno[2,1-c]quinoline derivatives.
AID502988	Ratio of MIC for Mycobacterium smegmatis expressing ATP synthase AtpE D32V mutant protein to MIC for wild type Mycobacterium smegmatis ATCC 607 expressing vector pSD5	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1888136	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis clinical isolate HD2 assessed as inhibition of bacterial growth incubated for 7 days by by microplate alamar blue assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254	Exploring disordered loops in DprE1 provides a functional site to combat drug-resistance in Mycobacterium strains.
AID1181169	Antimicrobial activity against second mutant generation Mycobacterium tuberculosis 1024_18 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID1639008	Inhibition of human ERG	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1861239	AUC in Sprague-Dawley rat at 200 mg/kg,po measured after 12 days	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1367751	Antitubercular activity against Mycobacterium tuberculosis H37Rv incubated for 10 days in non-replicating anaerobic condition followed by incubation for 28 hrs in ambient gaseous condition measured after day 11 by LORA assay	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID528941	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 4 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861225	Drug concentration in CD-1 mouse lung at 6.25 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1389808	Inhibition of human ERG assessed as prolongation of QT interval	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID521903	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 5 expressing wild type atpE and F0 operon selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID372806	Antimicrobial activity against Mycobacterium shimoidei after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID502998	Antimicrobial activity against wild-type Mycobacterium tuberculosis expressing ATP synthase AtpE assessed as growth inhibition in early log-phase by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1861198	Microsomal stability in human liver microsomes assessed as clearance	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372784	Antimicrobial activity against Mycobacterium avium 21 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1639005	Antitubercular activity against Mycobacterium tuberculosis H37Rv incubated for 10 days in non-replicating anaerobic condition followed by incubation for 28 hrs in ambient gaseous condition and measured after day 11 by LORA assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1726774	Antitubercular activity against Mycobacterium tuberculosis H37Rv assessed as bacterial growth inhibition incubated for 5 days by resazurin microtiter assay	2021	RSC medicinal chemistry, Jun-23, Volume: 12, Issue:6 ISSN: 2632-8682	Synthesis and evaluation of pyridine-derived bedaquiline analogues containing modifications at the A-ring subunit.
AID544551	Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 1 uM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID502982	Antimicrobial activity against wild type Mycobacterium smegmatis ATCC 607 by 7H9 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1483722	Selectivity ratio of IC50 for NDH2 in Mycobacterium smegmatis inverted membrane vesicles using NADH as substrate to IC50 for SDH in Mycobacterium smegmatis inverted membrane vesicles using succinate as substrate	2017	Journal of medicinal chemistry, 02-23, Volume: 60, Issue:4 ISSN: 1520-4804	Discovery of Imidazo[1,2-a]pyridine Ethers and Squaramides as Selective and Potent Inhibitors of Mycobacterial Adenosine Triphosphate (ATP) Synthesis.
AID372791	Antimicrobial activity against Mycobacterium mageritense after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1639017	Protein binding in human plasma	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1861242	Toxicity in Beagle dog assessed as effect on electrocardiogram at 200 mg/kg,po	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1638951	Intrinsic clearance in human liver microsomes	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1162176	Antitubercular activity against Mycobacterium tuberculosis assessed as growth inhibition by alamar blue assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86ISSN: 1768-3254	SAR analysis of new anti-TB drugs currently in pre-clinical and clinical development.
AID544549	Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 5 uM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID1743152	Inhibition of ATP synthase in bedaquiline-resistant Mycobacterium tuberculosis assessed as reduction in bacterial growth incubated for 7 days by microplate alamar blue assay	2020	European journal of medicinal chemistry, Nov-15, Volume: 206ISSN: 1768-3254	Design, synthesis and biological evaluation of diamino substituted cyclobut-3-ene-1,2-dione derivatives for the treatment of drug-resistant tuberculosis.
AID525533	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 1 expressing atpE Glu63Asp mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID562300	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861205	Inhibition of CYP3A4 (unknown origin)	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1639010	Intrinsic clearance in human liver microsomes assessed per mg protein	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID502999	Antimicrobial activity against wild-type Mycobacterium tuberculosis isolate BK12 expressing ATP synthase AtpE A63P mutant protein assessed as growth inhibition in early log-phase by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID544559	Selectivity index, ratio of IC50 for human ATP synthase to IC50 for Mycobacterium smegmatis ATP synthase subunit c	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID765269	fT>MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID525513	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 4 expressing wild type atpE Glu61Asp mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1685617	Inhibition of cytochrome-bd oxidase in Mycobacterium bovis BCG assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in absence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID525521	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis H37Rv expressing wild type atpE selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID698992	AUC at steady state (0 to 24 hrs) in human at 150 mg, po qd for 14 days	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1638958	Ratio of AUC in mouse to MIC90 of replicating Mycobacterium tuberculosis H37Rv after 4 days by Alamar blue assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1192645	Inhibition of human ERG channel	2015	Bioorganic & medicinal chemistry, Feb-15, Volume: 23, Issue:4 ISSN: 1464-3391	Novel, potent, orally bioavailable and selective mycobacterial ATP synthase inhibitors that demonstrated activity against both replicating and non-replicating M. tuberculosis.
AID562469	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 302 t	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861233	Antimycobacterial activity against Mycobacterium tuberculosis infected by aerosol in mouse chronic infection model assessed as reduction in colony forming unit in lungs at 5 mg/kg, po treated 5 days per week from day 28 to day 58 post infection	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID765271	fAUC/MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID283235	Reduction of bacterial counts in Mycobacterium tuberculosis H37Rv infected Swiss mouse lung at 25 mg/kg, po for 5 days/week after 1 month	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3 ISSN: 0066-4804	Synergistic activity of R207910 combined with pyrazinamide against murine tuberculosis.
AID502981	Ratio of MIC for Mycobacterium tuberculosis H37Rv isolate BK12 expressing ATP synthase atpE A63P mutant protein to MIC for Mycobacterium tuberculosis H37Rv	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1389796	Antitubercular activity against Mycobacterium tuberculosis H37Rv after 24 hrs under aerobic condition by MABA	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID525535	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 1 expressing atpE Glu61Asp mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1900061	Inhibition of Mycobacterium smegmatis ATP synthase	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID502994	Antimicrobial activity against wild-type Mycobacterium smegmatis ATCC 607 expressing ATP synthase AtpE subunit by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID525517	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 6 expressing wild type atpE selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1375999	Inhibition of Mycobacterium tuberculosis H37Rv cytochrome bc1 oxidase assessed as reduction in ATP level measured up to 24 hrs under anaerobic condition	2016	MedChemComm, Nov-01, Volume: 7, Issue:11 ISSN: 2040-2503	SAR and identification of 2-(quinolin-4-yloxy)acetamides as
AID503005	Binding affinity to Bacillus PS3 ATP synthase subunit alpha by mass spectroscopy	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1772301	Non-covalent inhibition of DprE1 in Mycobacterium tuberculosis H37Rv measured after 7 days by microplate Alamar blue assay	2021	Journal of medicinal chemistry, 05-13, Volume: 64, Issue:9 ISSN: 1520-4804
AID1154349	Antimycobacterial activity against Mycobacterium tuberculosis over expressing TopA after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID1638955	AUC in mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1639006	Cytotoxicity against African green monkey Vero cells measured after 72 hrs by MTT assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1861234	Antimycobacterial activity against Mycobacterium tuberculosis infected by aerosol in mouse chronic infection model assessed as reduction in colony forming unit in lungs at 20 mg/kg, po treated 5 days per week from day 28 to day 58 post infection	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1154352	Antimycobacterial activity against TMC207R-resistant Mycobacterium tuberculosis clone 8.1 over expressing DprE1 mutant after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID372785	Antimicrobial activity against Mycobacterium avium 23 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1897864	Bactericidal activity against Non-replicating Mycobacterium tuberculosis ss18b-lux model assessed as decrease in luminescence at 10 to 10000 nM	2022	Journal of medicinal chemistry, 12-22, Volume: 65, Issue:24 ISSN: 1520-4804
AID1367746	Terminal half life in healthy human subjects dosed as single 400 mg dose on Day 1 followed by PK sampling (Days 1 to 14)	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID502990	Antimicrobial activity against wild type Mycobacterium smegmatis ATCC 607 by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID525532	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 2 expressing atpE Ala28Val mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1861200	Microsomal stability in mouse liver microsomes assessed as clearance	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID525525	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 3 expressing wild type atpE and F0 operon selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID529087	Tmax in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1154353	Antimycobacterial activity against moxifloxacin-resistant Mycobacterium tuberculosis clone 4.1 over expressing DprE1 mutant after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID525526	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 3 expressing wild type atpE selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID502974	Antimicrobial activity against Mycobacterium tuberculosis H37Rv by 7H9 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID562288	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1181172	Antimicrobial activity against second mutant generation Mycobacterium tuberculosis 1024_16.6 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID1639011	Intrinsic clearance in mouse liver microsomes assessed per mg protein	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1154350	Antimycobacterial activity against Mycobacterium tuberculosis over expressing PimA after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID529096	Toxicity in pulmonary tuberculosis patient assessed as hemoptysis at 100 mg/kg, po once daily	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1638960	Protein binding in human plasma	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID370056	Antimycobacterial activity against Mycobacterium tuberculosis	2005	Antimicrobial agents and chemotherapy, Jun, Volume: 49, Issue:6 ISSN: 0066-4804	New small-molecule synthetic antimycobacterials.
AID1650508	Inhibition of human ERG	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1861202	Inhibition of CYP2C9 (unknown origin)	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID544555	Inhibition of Mycobacterium smegmatis MC2 155 ATP synthase subunit c-mediated ATP production at 100 nM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID1483723	Selectivity ratio of IC50 for NADH dependent ATP synthesis in Mycobacterium smegmatis inverted membrane vesicles lacking cytochrome-bc1 complex to IC50 for cytochrome c oxidase in Mycobacterium smegmatis inverted membrane vesicles assessed as decrease in	2017	Journal of medicinal chemistry, 02-23, Volume: 60, Issue:4 ISSN: 1520-4804	Discovery of Imidazo[1,2-a]pyridine Ethers and Squaramides as Selective and Potent Inhibitors of Mycobacterial Adenosine Triphosphate (ATP) Synthesis.
AID565294	Antitubercular activity against Mycobacterium avium infected in C57BL/6J mouse assessed as reduction of CFU counts in spleen at 150 mg/kg, sc administered one month post-infection five times weekly for 3 months (Rvb = 7.9 +/- 0.7 log10CFU)	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID1603259	Selectivity index, ratio of IC50 for African green monkey Vero cells to MIC>=90 for Mycobacterium tuberculosis H37Rv	2019	ACS medicinal chemistry letters, Mar-14, Volume: 10, Issue:3 ISSN: 1948-5875
AID1638948	Inhibition of human ERG by manual patch clamp electrophysiology assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID372798	Antimicrobial activity against Mycobacterium scrofulaceum after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1861211	AUC (0 to last) in mouse at 6.25 mg/kg,po	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID529088	Tmax in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID310930	Antituberculosis activity against Mycobacterium tuberculosis	2007	Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7 ISSN: 0968-0896	Antituberculosis drugs: ten years of research.
AID525510	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis H37Rv	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1861191	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis assessed as mycobacterial growth inhibition	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID529095	Steady-state plasma concentration in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID372889	Antimicrobial activity against Mycobacterium avium 2 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID525536	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis H37Rv	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID372663	Antimicrobial activity against Mycobacterium avium complex isolate after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID372801	Antimicrobial activity against Mycobacterium szulgai after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1616089	Selectivity index, ratio of CC50 for human HepG2 cells to MIC of Mycobacterium tuberculosis H37Rv	2019	European journal of medicinal chemistry, Nov-15, Volume: 182ISSN: 1768-3254	Recent advancements in mechanistic studies and structure activity relationship of F
AID372792	Antimicrobial activity against Mycobacterium phlei after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1577421	Antitubercular activity against Mycobacterium tuberculosis H37Rv	2019	Journal of medicinal chemistry, 09-12, Volume: 62, Issue:17 ISSN: 1520-4804	Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-d-ribofuranose 2'-Oxidase.
AID1678479	Inhibition of recombinant His6-tagged SARS-CoV-2 main protease using Dabcyl-KTSAVLQ-SGFRKM-E(Edans-NH2) as substrate preincubated for 15 mins followed by substrate addition by FRET based assay	2020	ACS medicinal chemistry letters, Dec-10, Volume: 11, Issue:12 ISSN: 1948-5875	Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2.
AID1861196	Plasma protein binding in human assessed as bound fraction	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372795	Antimicrobial activity against Mycobacterium malmoense after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1897848	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv infected in human A-THP1 macrophages assessed as viability of infected macrophages incubated for 96 hrs by fluorescence microplate assay	2022	Journal of medicinal chemistry, 12-22, Volume: 65, Issue:24 ISSN: 1520-4804
AID372780	Antimicrobial activity against Mycobacterium avium 8 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID503003	Binding affinity to Mycobacterium smegmatis ATCC 607 ATP synthase subunit alpha by mass spectroscopy	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1638947	Cytotoxicity against African green monkey Vero cells after 72 hrs by MTS-PMS assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1883681	Antibacterial activity against Mycobacterium tuberculosis H37Rv assessed as inhibition of bacterial growth	2022	Journal of medicinal chemistry, 06-09, Volume: 65, Issue:11 ISSN: 1520-4804	Tuberculosis Drug Discovery: Challenges and New Horizons.
AID525523	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 5 expressing wild type atpE Ala63Pro mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID529084	Cmax in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID372799	Antimicrobial activity against Mycobacterium hiberniae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID502978	Antimicrobial activity against Mycobacterium tuberculosis H37Rv isolate LV13 expressing ATP synthase atpE I66M mutant protein by 7H10 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1603258	Cytotoxicity against African green monkey Vero cells measured after 72 hrs by CellTiter 96 aqueous non-radioactive cell proliferation assay	2019	ACS medicinal chemistry letters, Mar-14, Volume: 10, Issue:3 ISSN: 1948-5875
AID1476362	Antitubercular activity against bedaquiline resistant Mycobacterium tuberculosis H37Rv after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID765268	T>MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID544567	Inhibition of ATP synthase in bovine heart mitochondria assessed as inhibition of oxygen consumption	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID1698407	Metabolic stability in mouse liver microsomes assessed as intrinsic clearance	2020	Bioorganic & medicinal chemistry, 11-15, Volume: 28, Issue:22 ISSN: 1464-3391	Synthesis and structure-activity relationships for tetrahydroisoquinoline-based inhibitors of Mycobacterium tuberculosis.
AID1678478	Inhibition of recombinant His6-tagged SARS-CoV-2 main protease assessed as residual enzyme activity at 100 uM using Dabcyl-KTSAVLQ-SGFRKM-E(Edans-NH2) as substrate preincubated for 15 mins followed by substrate addition by FRET based assay relative to con	2020	ACS medicinal chemistry letters, Dec-10, Volume: 11, Issue:12 ISSN: 1948-5875	Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2.
AID1616093	Inhibition of ATP synthase in Mycobacterium smegmatis	2019	European journal of medicinal chemistry, Nov-15, Volume: 182ISSN: 1768-3254	Recent advancements in mechanistic studies and structure activity relationship of F
AID1861214	Volume of distribution at steady state in Sprague-Dawley rat at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID529110	Bactericidal activity against Mycobacterium tuberculosis selected on 100 times compound MIC measured after 6 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861229	Drug concentration in Sprague-Dawley rat plasma at 5 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID529100	Toxicity in pulmonary tuberculosis patient assessed as diarrhea at 400 mg/kg, po once daily	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID503000	Antimicrobial activity against wild-type Mycobacterium tuberculosis isolate LV13 expressing ATP synthase AtpE I66M mutant protein assessed as growth inhibition in early log-phase by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1685619	Inhibition of cytochrome-bd oxidase in Mycobacterium tuberculosis H37Rv assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in absence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID1483725	Inhibition of cytochrome c oxidase in Mycobacterium smegmatis inverted membrane vesicles lacking cytochrome-bd complex assessed as reduction of oxygen consumption treated between 250 to 450 secs post NADH addition	2017	Journal of medicinal chemistry, 02-23, Volume: 60, Issue:4 ISSN: 1520-4804	Discovery of Imidazo[1,2-a]pyridine Ethers and Squaramides as Selective and Potent Inhibitors of Mycobacterial Adenosine Triphosphate (ATP) Synthesis.
AID1162175	Antitubercular activity against drug-susceptible Mycobacterium tuberculosis clinical isolates assessed as growth inhibition	2014	European journal of medicinal chemistry, Oct-30, Volume: 86ISSN: 1768-3254	SAR analysis of new anti-TB drugs currently in pre-clinical and clinical development.
AID544565	Inhibition of ATP synthase in M18 mouse liver mitochondria assessed as inhibition of oxygen consumption	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID562305	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID528927	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 4 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1580695	Inhibition of Mycobacterium phlei DSM-43239 C-terminal ATP-synthase assessed as reduction in luciferase activity incubated for 10 mins in presence of ATP by luminometric method	2019	Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23 ISSN: 1520-4804	Changing the Rules of TB-Drug Discovery.
AID1638953	Clearance in iv dosed mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1389803	Half life in human liver microsomes at 1 uM in presence of CYP3A4 inhibitor ketoconazole	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID529092	AUC (0 to 24 hrs) in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861192	Antimycobacterial activity against drug-sensitive Mycobacterium tuberculosis assessed as mycobacterial growth inhibition	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372790	Antimicrobial activity against Mycobacterium fortuitum after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1162172	Antitubercular activity against drug-resistant Mycobacterium tuberculosis clinical isolates assessed as growth inhibition	2014	European journal of medicinal chemistry, Oct-30, Volume: 86ISSN: 1768-3254	SAR analysis of new anti-TB drugs currently in pre-clinical and clinical development.
AID1888138	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis clinical isolate HD4 assessed as inhibition of bacterial growth incubated for 7 days by by microplate alamar blue assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254	Exploring disordered loops in DprE1 provides a functional site to combat drug-resistance in Mycobacterium strains.
AID1900067	Half-life in mouse at 100 mg/kg, po administered as single dose	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID1698406	Metabolic stability in human liver microsomes assessed as intrinsic clearance	2020	Bioorganic & medicinal chemistry, 11-15, Volume: 28, Issue:22 ISSN: 1464-3391	Synthesis and structure-activity relationships for tetrahydroisoquinoline-based inhibitors of Mycobacterium tuberculosis.
AID1389799	Kinetic solubility of the compound in pH 7.4 KH2PO4/KOAc/KCl buffer	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1638959	Inhibition of CYP3A4 (unknown origin)	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID372800	Antimicrobial activity against Mycobacterium interjectum after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID529106	Cardiotoxicity in pulmonary tuberculosis patient assessed as increase in QT interval at 25 mg/kg, po once daily for 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1389800	Protein binding in human plasma	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID525519	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis Mycobacterium tuberculosis H37Rv expressing wild type atpE and F0 operon selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID562467	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 302 to	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID529086	Cmax in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1650512	Clearance in CD-1 mouse at 2 to 3 mg/kg, iv administered as single bolus dose	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1601486	Antimycobacterial activity against Mycobacterium bovis assessed as 90 percent growth inhibition measured after 120 hrs by turbidometric analysis	2019	Bioorganic & medicinal chemistry letters, 10-15, Volume: 29, Issue:20 ISSN: 1464-3405	Synthesis and evaluation of a novel quinoline-triazole analogs for antitubercular properties via molecular hybridization approach.
AID529109	Bactericidal activity against Mycobacterium tuberculosis selected on 10 times compound MIC measured after 6 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861216	Cmax in Sprague-Dawley rat at 5 mg/kg,po	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1154348	Antimycobacterial activity against Mycobacterium tuberculosis over expressing InhA after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID529108	Antimicrobial activity against drug-resistant Mycobacterium tuberculosis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID528924	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 1 day	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1638954	Apparent volume of distribution during terminal phase in iv dosed mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID1685620	Inhibition of cytochrome-bcc aa3 in Mycobacterium tuberculosis H37Rv assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in presence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID562295	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 120 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID528939	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 2 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1698408	Inhibition of Mycobacterium smegmatis ATPsynthase	2020	Bioorganic & medicinal chemistry, 11-15, Volume: 28, Issue:22 ISSN: 1464-3391	Synthesis and structure-activity relationships for tetrahydroisoquinoline-based inhibitors of Mycobacterium tuberculosis.
AID562297	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 3 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1639004	Antitubercular activity against Mycobacterium tuberculosis H37Rv after 4 days by microplate alamar blue assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID1389802	Half life in human liver microsomes at 1 uM	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1154347	Antimycobacterial activity against Mycobacterium tuberculosis over expressing DprE1 after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID1181167	Antimicrobial activity against first mutant generation Mycobacterium tuberculosis 1024_1 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID502979	Antimicrobial activity against Mycobacterium tuberculosis H37Rv isolate BK12 expressing ATP synthase atpE A63P mutant protein by 7H10 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1861194	Apparent permeability across basolateral side to apical side in dog MDCK cells	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID544553	Inhibition of Mycobacterium smegmatis MC2 155 ATP synthase subunit c-mediated ATP production	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID529090	AUC (0 to 24 hrs) in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID562289	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 30 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID528930	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861228	Drug concentration in Sprague-Dawley rat lung at 5 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1638945	Antitubercular activity against replicating Mycobacterium tuberculosis H37Rv after 4 days by Alamar blue assay	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID669835	Antibacterial activity against non-replicating Mycobacterium tuberculosis H37Rv ATCC 27294 by low oxygen recovery assay	2012	Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8 ISSN: 1520-4804	Discovery of selective menaquinone biosynthesis inhibitors against Mycobacterium tuberculosis.
AID502997	Inhibition of Mycobacterium tuberculosis ATP synthase subunit c-mediated ATP synthesis after 24 hrs mins by luminometry	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1638952	Intrinsic clearance in mouse liver microsomes	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID562293	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861206	Inhibition of human ERG	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID528943	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 6 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID765273	fCmax/MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID525512	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 4 expressing wild type atpE and F0 operon selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID525518	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis H37Rv expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID528944	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID529104	Cardiotoxicity in pulmonary tuberculosis patient assessed as increase in QT interval at 100 mg/kg, po once daily for 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1679141	Inhibition of Mycobacterium bovis BCG QcrB assessed as decrease in ATP level at 0.01 to 10 uM incubated for 20 hrs by Bactiter-Glo microbial cell viability assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds.
AID1504967	Cytotoxicity against African green monkey Vero cells after 72 hrs by MTS/PMS assay	2017	ACS medicinal chemistry letters, Dec-14, Volume: 8, Issue:12 ISSN: 1948-5875	Antitubercular Nitroimidazoles Revisited: Synthesis and Activity of the Authentic 3-Nitro Isomer of Pretomanid.
AID1530552	Antimycobacterial activity against Mycobacterium tuberculosis	2019	European journal of medicinal chemistry, Jan-01, Volume: 161ISSN: 1768-3254	Naphthalene, a versatile platform in medicinal chemistry: Sky-high perspective.
AID1861209	Half life in mouse at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID562304	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 100 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1476360	Antitubercular activity against rifampicin resistant Mycobacterium tuberculosis H37Rv ATCC 35838 after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID529081	Cmin in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID529101	Toxicity in pulmonary tuberculosis patient assessed as somnolence at 400 mg/kg, po once daily for 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID503002	Binding affinity to Bacillus PS3 ATP synthase subunit c A63P mutant	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1772305	Non-covalent inhibition of DprE1 in bedaquiline-resistant Mycobacterium tuberculosis measured after 7 days by microplate Alamar blue assay	2021	Journal of medicinal chemistry, 05-13, Volume: 64, Issue:9 ISSN: 1520-4804
AID529082	Cmin in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861190	Cytotoxicity against African green monkey Vero cells	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID525527	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 3 expressing wild type atpE and ATP synthase selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID565295	Antitubercular activity against Mycobacterium avium infected in C57BL/6J mouse assessed as reduction of CFU counts in spleen at 25 mg/kg, po administered one month post-infection five times weekly for 4 months (Rvb = 8.9 +/- 0.3 log10CFU)	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID372664	Antimicrobial activity against Mycobacterium avium 1 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID529094	Steady-state plasma concentration in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID502985	Antimicrobial activity against wild type Mycobacterium smegmatis ATCC 607 expressing vector pSD5 by 7H9 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1650511	Intrinsic clearance in mouse liver microsomes assessed per mg protein	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1861218	Oral bioavailability in Sprague-Dawley rat at 5 mg/kg	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372787	Antimicrobial activity against Mycobacterium intracellular 20 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1726776	Terminal half life in human	2021	RSC medicinal chemistry, Jun-23, Volume: 12, Issue:6 ISSN: 2632-8682	Synthesis and evaluation of pyridine-derived bedaquiline analogues containing modifications at the A-ring subunit.
AID562466	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 30 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 302 to	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID544543	Antimicrobial activity against Mycobacterium smegmatis	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID1650507	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as bacterial growth inhibition incubated for 10 days under anerobic condition followed by incubation under ambient gaseous condition for 28 days by low oxygen recovery assay	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1832953	Antitubercular activity against Mycobacterium tuberculosis mc2 6230 assessed as inhibition of bacterial growth incubated for 7 days	2021	Bioorganic & medicinal chemistry, 11-01, Volume: 49ISSN: 1464-3391	Discovery of 5-methylpyrimidopyridone analogues as selective antimycobacterial agents.
AID528929	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 6 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1871986	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv by agar dilution method	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Tuberculosis drug discovery: Progression and future interventions in the wake of emerging resistance.
AID372783	Antimicrobial activity against Mycobacterium avium 16 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1638956	Oral bioavailability in mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID562303	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 50 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861241	Toxicity in Sprague-Dawley rat assessed as death at 200 mg/kg,po measured after 12 days	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID529085	Cmax in pulmonary tuberculosis patient at 100 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID372796	Antimicrobial activity against Mycobacterium gordonae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1367747	Inhibition of human ERG	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID525514	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 6 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1367753	Oral bioavailability in rat	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID1861189	Cytotoxicity against human HeLa cells	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID372782	Antimicrobial activity against Mycobacterium avium 11 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1861207	Clearance in mouse at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID525534	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 1 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID525524	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 5 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID502991	Antimicrobial activity against Mycobacterium smegmatis isolate R09 expressing ATP synthase AtpE D32V mutant protein by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1679140	Inhibition of Mycobacterium bovis BCG QcrB harboring CydAB deletion mutant assessed as decrease in ATP level at 0.01 to 10 uM incubated for 20 hrs by Bactiter-Glo microbial cell viability assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds.
AID1650517	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv infected in BALB/c mouse model of acute infection assessed as log reduction in bacterial burden in lung at 16.7 mg/kg, po via gavage administered as single dose for 12 days starting from	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID502976	Antimicrobial activity against Mycobacterium tuberculosis H37Rv isolate BK12 expressing ATP synthase atpE A63P mutant protein by 7H9 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1639012	Half life in human liver microsomes	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID528961	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured on day 8 after starting standard TB therapy	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1650514	AUC (0 to infinity) in CD-1 mouse at 10 mg/kg, po via gavage administered as single dose	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID1616096	Antimicrobial activity against Mycobacterium tuberculosis H37Rv	2019	European journal of medicinal chemistry, Nov-15, Volume: 182ISSN: 1768-3254	Recent advancements in mechanistic studies and structure activity relationship of F
AID1685622	Inhibition of cytochrome-bcc aa3 Mycobacterium tuberculosis clinical isolate N0145 assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in presence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID521902	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 4 expressing wild type atpE Asp28Pro mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID372797	Antimicrobial activity against Mycobacterium simiae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1638946	Antitubercular activity against non-replicating Mycobacterium tuberculosis H37Rv after 10 days by LORA	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	Structure-activity relationships for unit C pyridyl analogues of the tuberculosis drug bedaquiline.
AID698991	AUC at steady state (0 to 24 hrs) in human at 50 mg, po qd for 14 days	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1181168	Antimicrobial activity against first mutant generation Mycobacterium tuberculosis 1024_18 assessed as fold shift in MIC relative to parent strain	2014	Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15 ISSN: 1520-4804	Diarylthiazole: an antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system.
AID699004	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1367752	Inhibition of CYP3A4 (unknown origin) after 20 mins	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID1503833	Lipophilicity, log P of the compound	2017	ACS medicinal chemistry letters, Oct-12, Volume: 8, Issue:10 ISSN: 1948-5875
AID565302	Antimicrobial activity against Mycobacterium tuberculosis	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID525516	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 6 expressing wild type atpE Ala63Pro mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID528934	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 4 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID698819	Antimycobacterial activity against Mycobacterium tuberculosis infected in human assessed as log reduction of bacterial count at 400 mg, qd measured up to 7 days	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID562283	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 1 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID372781	Antimicrobial activity against Mycobacterium avium 9 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID562302	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 30 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1367754	Cytotoxicity against African green monkey Vero cells after 72 hrs by MTS-PMS assay	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID544561	Inhibition of ATP synthase in M18 mouse liver mitochondria assessed as effect on oxygen consumption at 175 uM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID1726775	Inhibition of fluorescently labelled tracer binding to human ERG by competitive binding assay	2021	RSC medicinal chemistry, Jun-23, Volume: 12, Issue:6 ISSN: 2632-8682	Synthesis and evaluation of pyridine-derived bedaquiline analogues containing modifications at the A-ring subunit.
AID765270	AUC/MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID528940	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 3 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID562286	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 12.5 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 1	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861208	Volume of distribution at steady state in mouse at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1504965	Antitubercular activity against Mycobacterium tuberculosis H37Rv measured after 7 days under aerobic condition by alamar blue assay	2017	ACS medicinal chemistry letters, Dec-14, Volume: 8, Issue:12 ISSN: 1948-5875	Antitubercular Nitroimidazoles Revisited: Synthesis and Activity of the Authentic 3-Nitro Isomer of Pretomanid.
AID525511	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 4 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1888137	Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis clinical isolate HD3 assessed as inhibition of bacterial growth incubated for 7 days by by microplate alamar blue assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254	Exploring disordered loops in DprE1 provides a functional site to combat drug-resistance in Mycobacterium strains.
AID1476364	Antitubercular activity against streptomycin resistant Mycobacterium tuberculosis H37Rv ATCC 35820 after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID562296	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 1 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1743153	Ratio of MIC for inhibition of ATP synthase in bedaquiline-resistant Mycobacterium tuberculosis to MIC for inhibition of ATP synthase in Mycobacterium tuberculosis H37Rv	2020	European journal of medicinal chemistry, Nov-15, Volume: 206ISSN: 1768-3254	Design, synthesis and biological evaluation of diamino substituted cyclobut-3-ene-1,2-dione derivatives for the treatment of drug-resistant tuberculosis.
AID1650515	Oral bioavailability in CD-1 mouse at 10 mg/kg administered via gavage as single dose	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID372804	Antimicrobial activity against R207910 resistant Mycobacterium novocastrense after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID528938	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 400 mg/kg, po once daily measured after 1 day	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861201	Inhibition of CYP1A2 (unknown origin)	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID502987	Antimicrobial activity against Mycobacterium smegmatis ATCC 607 expressing ATP synthase AtpE subunit by 7H9 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1861217	AUC (0 to last) in Sprague-Dawley rat at 5 mg/kg,po	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1900063	Selectivity ratio of IC50 for Mycobacterium smegmatis ATP synthase over IC50 for human ATP synthase	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID502992	Antimicrobial activity against wild type Mycobacterium smegmatis ATCC 607 expressing vector pSD5 by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID699003	Antimycobacterial activity against Mycobacterium tuberculosis clinical isolate	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1743131	Inhibition of ATP synthase in Mycobacterium tuberculosis H37Rv assessed as reduction in bacterial growth incubated for 7 days by microplate alamar blue assay	2020	European journal of medicinal chemistry, Nov-15, Volume: 206ISSN: 1768-3254	Design, synthesis and biological evaluation of diamino substituted cyclobut-3-ene-1,2-dione derivatives for the treatment of drug-resistant tuberculosis.
AID1389811	Antitubercular activity against Mycobacterium tuberculosis Erdman infected in BALB/c mouse assessed as reduction in bacterial burden in lungs at 20 mg/kg, po qd for 12 continuous days from day 11 post infection measured on day 25 relative to 20 mg/kg beda	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1861213	Clearance in Sprague-Dawley rat at 1 mg/kg,iv	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID502993	Antimicrobial activity against Mycobacterium smegmatis expressing ATP synthase AtpE D32V mutant protein by 7H10 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID502983	Antimicrobial activity against Mycobacterium smegmatis isolate R09 expressing ATP synthase AtpE D32V mutant protein by 7H9 agar dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID525537	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 4 expressing wild type atpE Glu61Asp mutant selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID1154351	Antimycobacterial activity against BTZ043-resistant Mycobacterium tuberculosis over expressing DprE1 C387S mutant after 5 days by standard microdilution method	2014	Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12 ISSN: 1520-4804	4-aminoquinolone piperidine amides: noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity.
AID502996	Inhibition of Mycobacterium tuberculosis isolate LV13 ATP synthase subunit c I66M mutant-mediated ATP synthesis after 24 hrs by luminometry	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1650513	Apparent volume of distribution during terminal phase in CD-1 mouse at 2 to 3 mg/kg, iv administered as single bolus dose	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID528964	Drug uptake in pulmonary tuberculosis patient at 25 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1685621	Inhibition of cytochrome-bd oxidase in Mycobacterium tuberculosis clinical isolate N0145 assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in absence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID503004	Binding affinity to Mycobacterium smegmatis ATCC 607 ATP synthase subunit beta by mass spectroscopy	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1389801	Oral bioavailability in CD-1 mouse at 10 mg/kg	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID581001	Antimicrobial activity against multiple drug-resistant Mycobacterium tuberculosis	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	New drugs against tuberculosis: problems, progress, and evaluation of agents in clinical development.
AID699002	Cmax in human at 400 mg, po	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1639018	Antitubercular activity against Mycobacterium tuberculosis H37Rv infected in BALB/c mouse assessed as log reduction in lung colony forming units at 20 mg/kg, po administered daily via gavage for 12 days starting from 10 days post-infection	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID283243	Reduction of lung lesions in Mycobacterium tuberculosis H37Rv infected Swiss mouse at 25 mg/kg, po for 5 days/week after 1 month	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3 ISSN: 0066-4804	Synergistic activity of R207910 combined with pyrazinamide against murine tuberculosis.
AID528925	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 25 mg/kg, po once daily measured after 2 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1476361	Antitubercular activity against moxifloxacin resistant Mycobacterium tuberculosis H37Rv after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID528935	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 5 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861203	Inhibition of CYP2C19 (unknown origin)	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID502995	Inhibition of Mycobacterium tuberculosis isolate BK12 ATP synthase subunit c A63P mutant-mediated ATP synthesis after 24 hrs by luminometry	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID372778	Antimicrobial activity against Mycobacterium avium 4 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID1861210	Cmax in mouse at 6.25 mg/kg,po	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1504966	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 incubated for 10 days under low oxygen condition followed by second incubation under aerobic condition for 28 hrs by LORA	2017	ACS medicinal chemistry letters, Dec-14, Volume: 8, Issue:12 ISSN: 1948-5875	Antitubercular Nitroimidazoles Revisited: Synthesis and Activity of the Authentic 3-Nitro Isomer of Pretomanid.
AID529107	Antimicrobial activity against drug-sensitive Mycobacterium tuberculosis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1164300	Inhibition of oxidative phosphorylation in Mycobacterium smegmatis membrane vesicles assessed as inhibition of NADH driven ATP synthesis by luciferin/luciferase assay	2014	ACS medicinal chemistry letters, Sep-11, Volume: 5, Issue:9 ISSN: 1948-5875	2-Phenylindole and Arylsulphonamide: Novel Scaffolds Bactericidal against Mycobacterium tuberculosis.
AID1603254	Antibacterial activity against Mycobacterium tuberculosis H37Rv after 7 days by microplate alamar blue assay	2019	ACS medicinal chemistry letters, Mar-14, Volume: 10, Issue:3 ISSN: 1948-5875
AID562299	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 12.5 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 2	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID372794	Antimicrobial activity against Mycobacterium kansasii after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID562465	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 120 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1639016	Oral bioavailability in mouse	2019	Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7 ISSN: 1464-3391	3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel.
AID372789	Antimicrobial activity against Mycobacterium chelonae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID562294	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 100 mg/kg, po administered once monthly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1503832	Antitubercular activity against Mycobacterium tuberculosis H37Rv after 4 days by MABA method	2017	ACS medicinal chemistry letters, Oct-12, Volume: 8, Issue:10 ISSN: 1948-5875
AID1861197	Plasma protein binding in rat assessed as bound fraction	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID1861188	Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as mycobacterial growth inhibition by low oxygen recovery assay	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID525515	Antimicrobial activity against drug-susceptible Mycobacterium tuberculosis isolate 6 expressing wild type atpE Glu61Asp mutant selected after 30 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID580999	Half life in human	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	New drugs against tuberculosis: problems, progress, and evaluation of agents in clinical development.
AID1389797	Antitubercular activity against Mycobacterium tuberculosis H37Rv incubated for 10 days in non-replicating anaerobic condition followed by incubation for 28 hrs in ambient gaseous condition measured on day 11 by LORA assay	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1685618	Inhibition of cytochrome-bd oxidase in Mycobacterium bovis BCG assessed as replicating ATP by measuring ATP depletion incubated for 15 hrs in presence of Q203 by BacTiter-Glo luminescence assay	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1 ISSN: 2632-8682	Structure guided generation of thieno[3,2-
AID1900062	Inhibition of human ATP synthase	2022	European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254	Synthesis and structure-activity relationships for a new class of tetrahydronaphthalene amide inhibitors of Mycobacterium tuberculosis.
AID528936	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 6 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1476363	Antitubercular activity against capreomycin resistant Mycobacterium tuberculosis H37Rv after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID1603256	Antibacterial activity against RMP-resistant Mycobacterium tuberculosis after 7 days by microplate alamar blue assay	2019	ACS medicinal chemistry letters, Mar-14, Volume: 10, Issue:3 ISSN: 1948-5875
AID1268503	Antibacterial activity against Mycobacterium tuberculosis	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2 ISSN: 1464-3405	Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents.
AID372802	Antimicrobial activity against Mycobacterium terrae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID765272	Cmax/MIC in Mycobacterium tuberculosis infected mouse	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17 ISSN: 1464-3405	A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.
AID525530	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 2 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID529089	Tmax in pulmonary tuberculosis patient at 400 mg/kg, po once daily for 7 days by liquid chromatography-MS/MS analysis	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID283236	Reduction of bacterial counts in Mycobacterium tuberculosis H37Rv infected Swiss mouse lung at 25 mg/kg, po for 5 days/week after 2 months	2007	Antimicrobial agents and chemotherapy, Mar, Volume: 51, Issue:3 ISSN: 0066-4804	Synergistic activity of R207910 combined with pyrazinamide against murine tuberculosis.
AID698995	Antimycobacterial activity against drug-sensitive Mycobacterium tuberculosis	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID562291	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 100 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152 p	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1389805	Inhibition of human ERG by patch clamp assay	2018	Bioorganic & medicinal chemistry, 05-01, Volume: 26, Issue:8 ISSN: 1464-3391	Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.
AID1650510	Intrinsic clearance in human liver microsomes assessed per mg protein	2020	Bioorganic & medicinal chemistry, 01-01, Volume: 28, Issue:1 ISSN: 1464-3391	Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.
AID372793	Antimicrobial activity against Mycobacterium vaccae after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID528937	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured after 7 days	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1861230	Ratio of drug concentration in Sprague-Dawley rat lung to plasma at 5 mg/kg,po measured after 96 hrs	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID562284	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 3 mg/kg, po administered 5 times weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 152	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID525528	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 3 expressing wild type atpE and F0 operon selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID562301	Antimycobacterial activity against Mycobacterium leprae infected in CBA/J mouse assessed as microbial growth inhibition at 25 mg/kg, po administered once weekly during logarithmic multiplication from day 60 to day 150 post infection measured on day 228 po	2009	Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9 ISSN: 1098-6596	The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently.
AID1861195	Efflux ratio of apparent permeability across basolateral to apical over apical to basolateral membrane in dog MDCK cells	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID565307	Antitubercular activity against Mycobacterium avium infected in C57BL/6J mouse assessed as reduction of CFU counts in spleen at 25 mg/kg, po administered one day post-infection five times weekly for 1 month (Rvb = 8.0 +/- 0.9 log10CFU)	2009	Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11 ISSN: 1098-6596	ATP synthase inhibition of Mycobacterium avium is not bactericidal.
AID544547	Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 200 uM	2009	Antimicrobial agents and chemotherapy, Mar, Volume: 53, Issue:3 ISSN: 1098-6596	Selectivity of TMC207 towards mycobacterial ATP synthase compared with that towards the eukaryotic homologue.
AID528960	Bactericidal activity against Mycobacterium tuberculosis in pulmonary tuberculosis patient assessed as reduction in sputum bacterial count at 100 mg/kg, po once daily measured on day 8 after starting standard TB therapy	2008	Antimicrobial agents and chemotherapy, Aug, Volume: 52, Issue:8 ISSN: 1098-6596	Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis.
AID1476350	Antitubercular activity against isoniazid resistant Mycobacterium tuberculosis H37Rv ATCC 35822 after 24 hrs by MABA method	2017	Journal of medicinal chemistry, 10-26, Volume: 60, Issue:20 ISSN: 1520-4804	Design, Synthesis, and Characterization of N-Oxide-Containing Heterocycles with in Vivo Sterilizing Antitubercular Activity.
AID525529	Antimicrobial activity against multidrug-resistant Mycobacterium tuberculosis isolate 3 expressing wild type atpE selected after 10 times MIC drug exposure	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3 ISSN: 1098-6596	Rates and mechanisms of resistance development in Mycobacterium tuberculosis to a novel diarylquinoline ATP synthase inhibitor.
AID372786	Antimicrobial activity against Mycobacterium intracellular 7 after 2 to 4 weeks by two fold dilution method	2007	Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11 ISSN: 0066-4804	In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.
AID502977	Antimicrobial activity against Mycobacterium tuberculosis H37Rv by 7H10 broth dilution method	2007	Nature chemical biology, Jun, Volume: 3, Issue:6 ISSN: 1552-4450	Diarylquinolines target subunit c of mycobacterial ATP synthase.
AID1861231	Antimycobacterial activity against Mycobacterium tuberculosis infected by aerosol in mouse acute infection model assessed as reduction in colony forming unit in lungs at 5 to 20 mg/kg, po treated 5 days per week from day 28 to day 38 post infection	2022	Bioorganic & medicinal chemistry letters, 09-01, Volume: 71ISSN: 1464-3405	Discovery and preclinical profile of sudapyridine (WX-081), a novel anti-tuberculosis agent.
AID698994	Antimycobacterial activity against drug-resistant Mycobacterium tuberculosis	2012	European journal of medicinal chemistry, May, Volume: 51ISSN: 1768-3254	Tuberculosis: the drug development pipeline at a glance.
AID1897867	Bactericidal activity against Non-replicating Mycobacterium tuberculosis ss18b-lux assessed as decrease in colony forming unit measured at 1 uM after 1 weeks	2022	Journal of medicinal chemistry, 12-22, Volume: 65, Issue:24 ISSN: 1520-4804
AID1367755	Lipophilicity log P of the compound	2017	Bioorganic & medicinal chemistry letters, 12-01, Volume: 27, Issue:23 ISSN: 1464-3405	Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 ISSN: 2472-5560	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 ISSN: 1091-6490	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 ISSN: 1091-6490	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5 ISSN: 1521-0111	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5 ISSN: 1521-0111	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.

Research

Studies (688)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	41 (5.96)	29.6817
2010's	398 (57.85)	24.3611
2020's	249 (36.19)	2.80

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	41 (5.82%)	5.53%
Reviews	101 (14.35%)	6.00%
Case Studies	38 (5.40%)	4.05%
Observational	19 (2.70%)	0.25%
Other	505 (71.73%)	84.16%

Substance	Classes	Roles	Relationship Strength
5,7-dichlorokynurenic acid	quinolines		low
broxyquinoline	organohalogen compound; quinolines		low
bu 224	quinolines		low
cilostamide	quinolines		low
cloxyquin	organochlorine compound; quinolines		low
ethoxyquin	aromatic ether; quinolines	antifungal agrochemical; food antioxidant; genotoxin; geroprotector; herbicide; Hsp90 inhibitor; neuroprotective agent; UDP-glucuronosyltransferase activator	low
fleroxacin	difluorobenzene; fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; quinolines	antibacterial drug; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor	low
mefloquine hydrochloride	organofluorine compound; piperidines; quinolines; secondary alcohol		low
oxamniquine	aromatic primary alcohol; C-nitro compound; quinolines; secondary amino compound		low
procaterol	quinolines		low
6-nitroquipazine	nitro compound; quinolines		low
pf 5901	quinolines		low
quinophthalone	aromatic ketone; beta-diketone; quinolines	dye	low
echinopsine	quinolines		low
dimoxyline	quinolines		low
quinoline	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines		low
6-methylquinoline	quinolines		low
2-methylquinoline	quinolines		low
cinchophen	quinolines		low
oxycinchophen	quinolines		low
6-methoxyquinoline	aromatic ether; quinolines		low
actinoquinol	quinolines		low
nequinate	quinolines		low
miloxacin	quinolines		low
amifloxacin	quinolines		low
sarafloxacin	quinolines		low
rufloxacin	fluoroquinolone antibiotic; quinolines; quinolone antibiotic		low
clinafloxacin	quinolines		low
orbifloxacin	quinolines		low
marbofloxacin	quinolines		low
toborinone	quinolines		low
3,4-dihydro-2(1h)-quinolinone	quinolines		low
tilbroquinol	organohalogen compound; quinolines		low
pazufloxacin	quinolines		low
7-(trifluoromethyl)-1H-quinolin-4-one	quinolines		low
2-Methyl-4-quinolinol	quinolines		low
1,2,3,4-tetrahydroquinoline	quinolines		low
danofloxacin	quinolines		low
premafloxacin	quinolines		low
quinfamide	quinolines		low
grepafloxacin	fluoroquinolone antibiotic; quinolines; quinolone antibiotic		low
8-hydroxy-2-quinolinecarboxylic acid	quinolines		low
8-(trifluoromethyl)-1H-quinolin-4-one	quinolines		low
cloquintocet-mexyl	aromatic ether; carboxylic ester; organochlorine compound; quinolines		low
2-hydroxyamino-3-methylimidazolo(4,5-f)quinoline	quinolines		low
ulifloxacin	quinolines		low
8-hydroxycarteolol	quinolines		low
3-(4-carboxybenzoyl)-2-quinolinecarboxaldehyde	benzoic acids; quinolines	fluorochrome	low
sr 2640	quinolines		low
a 195773	macrolide antibiotic; monosaccharide derivative; quinolines	antibacterial drug; protein synthesis inhibitor	low
torcetrapib	(trifluoromethyl)benzenes; carbamate ester; quinolines	anticholesteremic drug; CETP inhibitor	low
mefloquine carboxylic acid	quinolines		low
6-Methoxyquinoline N-oxide	quinolines		low
1-[(4-methoxyphenyl)-oxomethyl]-2H-quinoline-2-carbonitrile	quinolines		low
2-quinolinecarboxylic acid (4-nitrophenyl) ester	quinolines		low
3-nitro-1H-quinolin-4-one	nitro compound; quinolines		low
graveoline	quinolines		low
Dubamine	quinolines		low
saquinavir	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor	low
bms 195614	benzoic acids; quinolines; secondary carboxamide	retinoic acid receptor alpha antagonist	low
hts 466284	pyrazoles; pyridines; quinolines	TGFbeta receptor antagonist	low
5-carboxy-8-hydroxyquinoline	quinolines		low
sitafloxacin	fluoroquinolone antibiotic; quinolines; quinolone antibiotic		low
8-prop-2-enylsulfonylquinoline	quinolines		low
2-amino-3-cyano-5,6,7,8-tetrahydroquinoline-4-carboxylic acid methyl ester	quinolines		low
3-[[cyclopentyl-[[1-(phenylmethyl)-5-tetrazolyl]methyl]amino]methyl]-8-methyl-1H-quinolin-2-one	quinolines		low
N-[(8-methyl-2-oxo-1H-quinolin-3-yl)methyl]-N-(2-oxolanylmethyl)-2-furancarboxamide	quinolines		low
3-[(1-cyclopentyl-5-tetrazolyl)-(3,4-dihydro-1H-isoquinolin-2-yl)methyl]-7-methoxy-1H-quinolin-2-one	quinolines		low
3-[[1,3-benzodioxol-5-ylmethyl-[[1-(2-furanylmethyl)-5-tetrazolyl]methyl]amino]methyl]-6-methyl-1H-quinolin-2-one	quinolines		low
1-[3-(dimethylamino)propyl]-3-(4-fluorophenyl)-1-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]urea	quinolines		low
1-[3-(dimethylamino)propyl]-1-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-phenylurea	quinolines		low
6-[[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]-[1-(2-methylbutan-2-yl)-5-tetrazolyl]methyl]quinoline	quinolines		low
3-[(1-tert-butyl-5-tetrazolyl)-[2-furanylmethyl(2-oxolanylmethyl)amino]methyl]-6-methoxy-1H-quinolin-2-one	quinolines		low
3-[[1,3-benzodioxol-5-ylmethyl-[(1-cyclopentyl-5-tetrazolyl)methyl]amino]methyl]-6-ethyl-1H-quinolin-2-one	quinolines		low
6-ethyl-3-[[[1-(2-furanylmethyl)-5-tetrazolyl]methyl-(phenylmethyl)amino]methyl]-1H-quinolin-2-one	quinolines		low
N-(2-hydroxyethyl)-5-methyl-N-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-2,1,3-benzothiadiazole-4-sulfonamide	quinolines		low
3-[[[1-[1-(2-furanylmethyl)-5-tetrazolyl]-2-methylpropyl]-(2-oxolanylmethyl)amino]methyl]-8-methyl-1H-quinolin-2-one	quinolines		low
6,8-dimethyl-3-[(3-methyl-1-piperidinyl)-[1-(2-oxolanylmethyl)-5-tetrazolyl]methyl]-1H-quinolin-2-one	quinolines		low
1-[3-(4-morpholinyl)propyl]-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-3-phenylurea	quinolines		low
6-methyl-3-[[[1-(phenylmethyl)-5-tetrazolyl]methyl-(thiophen-2-ylmethyl)amino]methyl]-1H-quinolin-2-one	quinolines		low
N-[(6-ethoxy-2-oxo-1H-quinolin-3-yl)methyl]-4-fluoro-N-(2-hydroxyethyl)benzamide	quinolines		low
6-ethoxy-3-[[2-oxolanylmethyl-[[1-(2-phenylethyl)-5-tetrazolyl]methyl]amino]methyl]-1H-quinolin-2-one	quinolines		low
1-[(7,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-1-[(1-ethyl-2-pyrrolidinyl)methyl]-3-(2-methoxyphenyl)urea	quinolines		low
3-[1-azepanyl-[1-(phenylmethyl)-5-tetrazolyl]methyl]-7-methoxy-1H-quinolin-2-one	quinolines		low
3-[[[1-(2-furanylmethyl)-5-tetrazolyl]methyl-[(2-methoxyphenyl)methyl]amino]methyl]-6-methyl-1H-quinolin-2-one	quinolines		low
7-[[1-(2-oxolanylmethyl)-5-tetrazolyl]-(1-pyrrolidinyl)methyl]-5H-[1,3]dioxolo[4,5-g]quinolin-6-one	quinolines		low
1-(1,3-benzodioxol-5-ylmethyl)-3-(4-methylphenyl)-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]urea	quinolines		low
N-[(7-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(3-pyridinylmethyl)benzenesulfonamide	quinolines		low
1-[(1-tert-butyl-5-tetrazolyl)-thiophen-2-ylmethyl]-3,4-dihydro-2H-quinoline	quinolines		low
2-[(3-ethyl-2-quinolinyl)thio]-N-(5-methyl-3-isoxazolyl)acetamide	quinolines		low
3-cyclohexyl-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-1-[2-(1-pyrrolidinyl)ethyl]urea	quinolines		low
1-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-(4-methoxyphenyl)-1-(2-oxolanylmethyl)urea	quinolines		low
3-[3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl-[1-(2-oxolanylmethyl)-5-tetrazolyl]methyl]-6-ethyl-1H-quinolin-2-one	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(2-methylphenyl)propanamide	quinolines		low
3-[[[1-[(4-fluorophenyl)methyl]-5-tetrazolyl]methyl-(2-hydroxyethyl)amino]methyl]-7-methyl-1H-quinolin-2-one	quinolines		low
1-[2-(dimethylamino)ethyl]-1-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-(phenylmethyl)urea	quinolines		low
2-[[2-(1-azepanyl)-2-oxoethyl]thio]-6-methoxy-3-quinolinecarbonitrile	quinolines		low
6-methoxy-3-[[2-oxolanylmethyl-[1-[1-(phenylmethyl)-5-tetrazolyl]propyl]amino]methyl]-1H-quinolin-2-one	quinolines		low
3-[2-hydroxyethyl-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]sulfamoyl]benzoic acid ethyl ester	quinolines		low
3-(3-chlorophenyl)-1-(3-hydroxypropyl)-1-[(8-methyl-2-oxo-1H-quinolin-3-yl)methyl]urea	quinolines		low
6-methoxy-3-[[[1-(2-methoxyethyl)-5-tetrazolyl]methyl-(3-pyridinylmethyl)amino]methyl]-1H-quinolin-2-one	quinolines		low
4-bromo-N-[(6-ethoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(2-hydroxyethyl)benzamide	quinolines		low
6-ethoxy-3-[[[1-(2-methylbutan-2-yl)-5-tetrazolyl]methyl-(thiophen-2-ylmethyl)amino]methyl]-1H-quinolin-2-one	quinolines		low
3-[3,4-dihydro-1H-isoquinolin-2-yl-[1-(2-methylbutan-2-yl)-5-tetrazolyl]methyl]-7-methoxy-1H-quinolin-2-one	quinolines		low
1-[3-(dimethylamino)propyl]-1-[(5,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-3-(phenylmethyl)urea	quinolines		low
3-(2-chlorophenyl)-1-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-1-[2-(1-pyrrolidinyl)ethyl]urea	quinolines		low
8-[(1-tert-butyl-5-tetrazolyl)-thiomorpholin-4-ylmethyl]-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-7-one	quinolines		low
1-cyclopentyl-1-[(7-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-(2-methoxyphenyl)urea	quinolines		low
3-[3,4-dihydro-1H-isoquinolin-2-yl-[1-(2-oxolanylmethyl)-5-tetrazolyl]methyl]-6-methyl-1H-quinolin-2-one	quinolines		low
2-fluoro-N-(2-hydroxyethyl)-N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]benzamide	quinolines		low
3-[[(1-tert-butyl-5-tetrazolyl)methyl-(thiophen-2-ylmethyl)amino]methyl]-6-ethoxy-1H-quinolin-2-one	quinolines		low
6-ethoxy-3-[[2-furanylmethyl-[[1-(phenylmethyl)-5-tetrazolyl]methyl]amino]methyl]-1H-quinolin-2-one	quinolines		low
3-[1-azepanyl-[1-[(4-fluorophenyl)methyl]-5-tetrazolyl]methyl]-6,7-dimethoxy-1H-quinolin-2-one	quinolines		low
N-(2-furanylmethyl)-N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]benzamide	quinolines		low
N-[(6,7-dimethoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(3-hydroxypropyl)benzenesulfonamide	quinolines		low
6-methoxy-3-[[2-oxolanylmethyl-[[1-(phenylmethyl)-5-tetrazolyl]methyl]amino]methyl]-1H-quinolin-2-one	quinolines		low
1-[(6,7-dimethoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-(phenylmethyl)-1-(3-pyridinylmethyl)urea	quinolines		low
4-[2-(3,4-dihydro-2H-quinolin-1-yl)-2-oxoethyl]-5-furo[3,2-b]pyrrolecarboxylic acid ethyl ester	quinolines		low
4-methyl-6-(methylthio)-1H-quinolin-2-one	quinolines		low
2-[(3-cyano-5,7-dimethyl-2-quinolinyl)thio]-N-(2-furanylmethyl)acetamide	quinolines		low
3-[[cyclopentyl-[[1-[(4-methoxyphenyl)methyl]-5-tetrazolyl]methyl]amino]methyl]-7-methyl-1H-quinolin-2-one	quinolines		low
3-cyclohexyl-1-[(6,7-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-1-[3-(4-morpholinyl)propyl]urea	quinolines		low
3-[[1-(1,3-benzodioxol-5-ylmethyl)-5-tetrazolyl]-(1-pyrrolidinyl)methyl]-8-methyl-1H-quinolin-2-one	quinolines		low
3-[[1-[1-(2-furanylmethyl)-5-tetrazolyl]propyl-(2-phenylethyl)amino]methyl]-7-methoxy-1H-quinolin-2-one	quinolines		low
1-[(5,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-1-(2-furanylmethyl)-3-phenylurea	quinolines		low
N-(2-furanylmethyl)-N-[(7-methyl-4-tetrazolo[1,5-a]quinolinyl)methyl]-2-phenoxyacetamide	quinolines		low
9-oxo-N-(3-pyridinylmethyl)-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinoline-8-carboxamide	aromatic amide; quinolines		low
(6-fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-[5-(2-furanyl)-7-(trifluoromethyl)-2-pyrazolo[1,5-a]pyrimidinyl]methanone	quinolines		low
6-methoxy-3-[[[1-(2-oxolanylmethyl)-5-tetrazolyl]methyl-(2-phenylethyl)amino]methyl]-1H-quinolin-2-one	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(thiophen-2-ylmethyl)-2,1,3-benzothiadiazole-4-sulfonamide	quinolines		low
1-piperidinecarboxylic acid (5-chloro-8-quinolinyl) ester	organochlorine compound; quinolines		low
N-[(5,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-4-methoxy-N-[3-(2-oxo-1-pyrrolidinyl)propyl]benzenesulfonamide	quinolines		low
4-chloro-N-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-N-(2-oxolanylmethyl)benzenesulfonamide	quinolines		low
3-[3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl-[1-(2-oxolanylmethyl)-5-tetrazolyl]methyl]-5,7-dimethyl-1H-quinolin-2-one	quinolines		low
2-[[3-cyano-4-(5-methyl-2-furanyl)-5,6,7,8-tetrahydroquinolin-2-yl]thio]acetic acid methyl ester	quinolines		low
N-[(2R,4S)-2-methyl-1-(1-oxopropyl)-3,4-dihydro-2H-quinolin-4-yl]-N-phenylacetamide	quinolines		low
1-ethyl-6-methoxy-4-oxo-3-quinolinecarboxylic acid	quinolines		low
2-[[3-cyano-4-(2-furanyl)-5,6,7,8-tetrahydroquinolin-2-yl]thio]-N-(2-methylphenyl)acetamide	quinolines		low
2-(6-bromo-2-methyl-4-oxo-1-quinolinyl)-N-(2-methoxyphenyl)acetamide	quinolines		low
3-methyl-N-(1-propyl-3-pyrazolo[3,4-b]quinolinyl)butanamide	quinolines		low
N-(1-propyl-3-pyrazolo[3,4-b]quinolinyl)butanamide	quinolines		low
3-[(4-methoxyanilino)methyl]-1H-quinolin-2-one	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-methyl-4-pyridinecarboxamide	quinolines		low
3-(ethylaminomethyl)-6-methyl-1H-quinolin-2-one	quinolines		low
N-(1,8-dimethyl-3-pyrazolo[3,4-b]quinolinyl)propanamide	quinolines		low
2-methoxy-N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(2-methoxyphenyl)acetamide	quinolines		low
2,3-dihydroindol-1-yl-(6-fluoro-2-methyl-4-quinolinyl)methanone	quinolines		low
N-(1-ethyl-7-methyl-3-pyrazolo[3,4-b]quinolinyl)-2-furancarboxamide	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(4-methylphenyl)-2-oxolanecarboxamide	quinolines		low
N-[(7-methyl-2-oxo-1H-quinolin-3-yl)methyl]-N-propan-2-yl-4-pyridinecarboxamide	quinolines		low
N-[(7-methyl-2-oxo-1H-quinolin-3-yl)methyl]-N-propyl-2-pyridinecarboxamide	quinolines		low
N-butyl-N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-2-pyridinecarboxamide	quinolines		low
N-(1,7-dimethyl-3-pyrazolo[3,4-b]quinolinyl)acetamide	quinolines		low
N-(1-ethyl-6-methyl-3-pyrazolo[3,4-b]quinolinyl)-4-pyridinecarboxamide	quinolines		low
N-(2-furanylmethyl)-N-[(8-methyl-2-oxo-1H-quinolin-3-yl)methyl]-2-thiophenecarboxamide	quinolines		low
5-(1-imidazolylsulfonyl)-8-methoxyquinoline	quinolines		low
2-amino-4-(5-methyl-2-furanyl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile	quinolines		low
2-(8-quinolinylthio)acetic acid	quinolines		low
4-chloro-1-methyl-3-nitro-2-quinolinone	nitro compound; quinolines		low
4-(1H-benzimidazol-2-yl)quinoline	quinolines		low
3-[(4,8-dimethyl-2-quinolinyl)thio]propanoic acid	quinolines		low
3-pyridinecarboxylic acid (5-chloro-8-quinolinyl) ester	organochlorine compound; quinolines		low
2-amino-4-thiophen-2-yl-5,6,7,8-tetrahydroquinoline-3-carbonitrile	quinolines		low
2,2,2-trifluoro-N-(2-methyl-8-quinolinyl)acetamide	quinolines; secondary carboxamide; trifluoroacetamide		low
8-(3,5-dimethyl-1-pyrazolyl)quinoline	quinolines		low
1-methyl-4-[(4-methylphenyl)thio]-3-nitro-2-quinolinone	nitro compound; quinolines		low
4-chloro-2-methyl-3-(3-oxobutyl)-6-quinolinecarboxylic acid	quinolines		low
4-chloro-1-ethyl-3-nitro-2-quinolinone	nitro compound; quinolines		low
4-chloro-3-nitro-1-(phenylmethyl)-2-quinolinone	quinolines		low
6-(1,4,5,7-tetramethyl-6-pyrrolo[3,4-d]pyridazinyl)quinoline	quinolines		low
N-[[(2,4-dimethyl-8-quinolinyl)amino]-sulfanylidenemethyl]-4-methylbenzamide	quinolines		low
4,7-dimethoxy-1-methyl-2-quinolinone	quinolines		low
N-[3,4-dihydro-2H-quinolin-1-yl(sulfanylidene)methyl]-2-(3-methylphenoxy)acetamide	quinolines		low
2-[(7-ethyl-[1,3]dioxolo[4,5-g]quinolin-6-yl)thio]acetic acid propan-2-yl ester	quinolines		low
N-cyclopentyl-2-[(6-methoxy-3-methyl-2-quinolinyl)thio]acetamide	quinolines		low
4-(4-morpholinylmethyl)-3-quinolinol	quinolines		low
N-(4-hydroxyphenyl)-8-quinolinesulfonamide	quinolines		low
[2-(5-methyl-2-thiophenyl)-4-quinolinyl]-(1-pyrrolidinyl)methanone	quinolines		low
2-thiophenecarboxylic acid (6-methyl-2-oxo-1H-quinolin-3-yl)methyl ester	quinolines		low
N-[6-methyl-1-(2-methylpropyl)-3-pyrazolo[3,4-b]quinolinyl]-2-furancarboxamide	quinolines		low
3-[(6-methoxy-4-methyl-2-quinolinyl)thio]propanoic acid	quinolines		low
6-methoxy-3-[(3-methylanilino)methyl]-1H-quinolin-2-one	quinolines		low
3-[(2,5-dimethylanilino)methyl]-6-methoxy-1H-quinolin-2-one	quinolines		low
N-(5-quinolinyl)-2-benzofurancarboxamide	quinolines		low
1-(1-pyrrolidinyl)-2-(8-quinolinylthio)ethanone	quinolines		low
N-(5-bromo-8-quinolinyl)-5-[(4-chloro-1-pyrazolyl)methyl]-2-furancarboxamide	organohalogen compound; quinolines		low
1-[[[2-(2,4-dichlorophenyl)-4-quinolinyl]-oxomethyl]amino]-3-phenylurea	quinolines		low
2-[9-(4-methoxyphenyl)-1,8-dioxo-3,4,5,6,7,9-hexahydro-2H-acridin-10-yl]acetic acid	quinolines		low
2-(3-bromophenyl)-N-(4,5-dihydrothiazol-2-yl)-4-quinolinecarboxamide	quinolines		low
6-chloro-4-phenyl-3-(1-phenyl-5-tetrazolyl)quinoline	quinolines		low
2-[3-(4-methoxyphenyl)-1-benzo[f]quinolinyl]acetic acid ethyl ester	quinolines		low
[3-bromo-5-thiophen-2-yl-7-(trifluoromethyl)-2-pyrazolo[1,5-a]pyrimidinyl]-(3,4-dihydro-2H-quinolin-1-yl)methanone	quinolines		low
2-[2-oxo-2-(2,2,4,6-tetramethyl-1-quinolinyl)ethyl]isoindole-1,3-dione	quinolines		low
6-bromo-3-(4-morpholinyl)-4-phenyl-1H-quinolin-2-one	quinolines		low
7-chloro-2,3-dihydro-1H-cyclopenta[b]quinoline-9-carboxylic acid	quinolines		low
6-ethyl-2-thieno[2,3-b]quinolinecarboxylic acid	quinolines		low
N-[4-[(4-methyl-1-piperidinyl)sulfonyl]phenyl]-2-[(4-methyl-[1,2,4]triazolo[4,3-a]quinolin-1-yl)thio]acetamide	quinolines		low
2-[(7-methoxy-4-methyl-[1,2,4]triazolo[4,3-a]quinolin-1-yl)thio]-N-methyl-N-(4-phenyl-2-thiazolyl)acetamide	quinolines		low
1-cyclopentyl-1-[(5,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-3-ethylthiourea	quinolines		low
2-[[[1,3-benzodioxol-5-ylmethyl-[(6-methyl-2-oxo-1H-quinolin-3-yl)methyl]amino]-sulfanylidenemethyl]amino]benzoic acid methyl ester	quinolines		low
3-(4-ethoxyphenyl)-1-[2-(4-morpholinyl)ethyl]-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]thiourea	quinolines		low
1-[(6,7-dimethoxy-2-oxo-1H-quinolin-3-yl)methyl]-3-methyl-1-(thiophen-2-ylmethyl)thiourea	quinolines		low
2-[9-(3-chloro-4-methoxyphenyl)-1,8-dioxo-3,4,5,6,7,9-hexahydro-2H-acridin-10-yl]acetic acid	quinolines		low
N-[(6-chloro-2-oxo-4-phenyl-1H-quinolin-3-yl)methyl]-4-methylbenzenesulfonamide	quinolines		low
N-(2,6-dimethylphenyl)-2-[(6-methoxy-2-methyl-4-quinolinyl)thio]acetamide	quinolines		low
2-[(3-cyano-6-methoxy-2-quinolinyl)thio]-N-(2-methyl-1,3-benzothiazol-5-yl)acetamide	quinolines		low
1-(6-methoxy-2,2,4-trimethyl-1-quinolinyl)-2-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]thio]ethanone	quinolines		low
1-[(7,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-1-(2-furanylmethyl)-3-(2-methoxyphenyl)thiourea	quinolines		low
10-(4-methoxyphenyl)-3,4,5,6,7,9-hexahydro-2H-acridine-1,8-dione	quinolines		low
3-[[[2-(3-methylphenyl)-4-quinolinyl]-oxomethyl]amino]-2-thiophenecarboxylic acid methyl ester	quinolines		low
1-benzimidazolyl-[2-(4-methoxyphenyl)-4-quinolinyl]methanone	quinolines		low
N-(1,3-benzothiazol-2-yl)-2-(3-methoxyphenyl)-4-quinolinecarboxamide	quinolines		low
2-(4-ethylphenyl)-N-(4-methyl-1-piperazinyl)-4-quinolinecarboxamide	quinolines		low
LSM-27108	quinolines		low
[2-(4-propylphenyl)-4-quinolinyl]-[4-(2-pyridinyl)-1-piperazinyl]methanone	quinolines		low
2-(4-propylphenyl)-N-[2-(4-sulfamoylphenyl)ethyl]-4-quinolinecarboxamide	quinolines		low
2-(3-bromophenyl)-6-methyl-N-(1,2,4-triazol-4-yl)-4-quinolinecarboxamide	quinolines		low
N-(1,3-benzodioxol-5-yl)-6-methyl-2-(2-pyridinyl)-4-quinolinecarboxamide	quinolines		low
[4-[(2-chlorophenyl)methyl]-1-piperazinyl]-(6,8-dimethyl-2-pyridin-4-yl-4-quinolinyl)methanone	quinolines		low
2-[[5-[(2-methyl-8-quinolinyl)oxymethyl]-4-prop-2-enyl-1,2,4-triazol-3-yl]thio]acetamide	quinolines		low
2-phenyl-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-4-quinolinecarboxamide	quinolines		low
N-(4-fluorophenyl)-3-([1,2,4]triazolo[4,3-a]quinolin-1-ylthio)propanamide	quinolines		low
9-(3-bromo-4-hydroxyphenyl)-10-phenyl-3,4,5,6,7,9-hexahydro-2H-acridine-1,8-dione	quinolines		low
[2-(4-methoxyphenyl)-6-methyl-4-quinolinyl]-(4-morpholinyl)methanone	quinolines		low
7-[4-(4-acetamidophenyl)sulfonyl-1-piperazinyl]-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acid	quinolines		low
N-[6-methoxy-1-(2-methylpropyl)-3-pyrazolo[3,4-b]quinolinyl]-3-methylbutanamide	quinolines		low
2-(8-methoxy-2-methyl-4-oxo-1-quinolinyl)-N-(2-methoxyphenyl)acetamide	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-propan-2-yl-2-furancarboxamide	quinolines		low
1-[2-(3,4-dimethoxyphenyl)ethyl]-1-[(5,7-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-3-methylthiourea	quinolines		low
8,9-dimethyl-N-(3-methylphenyl)-3-[2-(4-morpholinyl)ethyl]-4H-[1,3]thiazino[6,5-b]quinolin-2-imine	quinolines		low
6-[[2-(4-morpholinyl)-2-oxoethyl]thio]-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-(2-phenylethyl)acetamide	quinolines		low
N-[(4-fluorophenyl)methyl]-N-[(8-methyl-2-oxo-1H-quinolin-3-yl)methyl]-4-morpholinecarboxamide	quinolines		low
4-methyl-N-[(2-methyl-4-quinolinyl)methyl]-3-nitrobenzamide	quinolines		low
2-(3,5-dimethyl-4-nitro-1-pyrazolyl)-N-[(2-methyl-4-quinolinyl)methyl]acetamide	quinolines		low
2-phenyl-N-[4-(2-thiazolylsulfamoyl)phenyl]-4-quinolinecarboxamide	quinolines		low
1-ethyl-3-[[[2-(2-methylpropyl)-4-quinolinyl]-oxomethyl]amino]thiourea	quinolines		low
2-[6-bromo-4-(2-chlorophenyl)-2-oxo-1H-quinolin-3-yl]acetic acid	quinolines		low
3-cyclohexyl-10-methyl-2-thiophen-2-ylpyrimido[4,5-b]quinoline-4,5-dione	quinolines		low
2-(4-fluorophenyl)-3-(2-furanylmethyl)-10-methylpyrimido[4,5-b]quinoline-4,5-dione	quinolines		low
N-(1-ethyl-6-methyl-3-pyrazolo[3,4-b]quinolinyl)-2-(4-methoxyphenyl)acetamide	quinolines		low
N-[3-(2-methoxyphenyl)-1-methyl-4-oxo-2-quinolinyl]-2-methylpropanamide	quinolines		low
N-(1,3-benzodioxol-5-ylmethyl)-8-quinolinesulfonamide	quinolines		low
1-(1,3-benzodioxol-5-ylmethylthio)-[1,2,4]triazolo[4,3-a]quinoline	quinolines		low
N-(4,5-dihydrothiazol-2-yl)-2-thiophen-2-yl-4-quinolinecarboxamide	quinolines		low
2-(4-methoxyphenyl)-4-quinolinecarboxylic acid [2-oxo-2-(propan-2-ylamino)ethyl] ester	quinolines		low
2-(2-furanyl)-4-quinolinecarboxylic acid [2-[4-amino-1-methyl-3-(2-methylpropyl)-2,6-dioxo-5-pyrimidinyl]-2-oxoethyl] ester	quinolines		low
1-cyclopropyl-7-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-1-piperazinyl]-6-fluoro-4-oxo-3-quinolinecarboxylic acid	quinolines		low
N-[5-(ethylthio)-1,3,4-thiadiazol-2-yl]-2-quinolinecarboxamide	quinolines		low
N-(3-acetyl-2-methyl-5-benzofuranyl)-N-(8-quinolinylsulfonyl)acetamide	quinolines		low
N-[3-(6-methyl-4-phenyl-2-quinolinyl)phenyl]methanesulfonamide	quinolines		low
2-[3-[(4-chlorophenyl)-oxomethyl]-6-methoxy-4-oxo-1-quinolinyl]-N-(4-fluorophenyl)acetamide	aromatic ketone; quinolines		low
5-[(4-fluorophenyl)methyl]-7-(4-methylphenyl)sulfonyl-[1,3]dioxolo[4,5-g]quinolin-8-one	quinolines		low
[9-(4-ethoxyphenyl)sulfonyl-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-yl]-(4-methylphenyl)methanone	aromatic ketone; quinolines		low
2-[[5-(5-chloro-2-thiophenyl)-1,3,4-oxadiazol-2-yl]thio]-1-(3,4-dihydro-2H-quinolin-1-yl)ethanone	quinolines		low
2-quinolinecarboxylic acid (4-oxo-1,2,3-benzotriazin-3-yl)methyl ester	quinolines		low
3,4-dihydro-2H-quinolin-1-yl-(4-propoxyphenyl)methanone	quinolines		low
N-(5-tert-butyl-3-isoxazolyl)-7-chloro-8-methyl-2-(2-pyridinyl)-4-quinolinecarboxamide	quinolines		low
6-bromo-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-(2-pyridinyl)-4-quinolinecarboxamide	quinolines		low
8-quinolinecarboxylic acid phenyl ester	quinolines		low
1-[4-(5-fluoro-1,2-benzoxazol-3-yl)-1-piperidinyl]-2-[(4-methyl-2-quinolinyl)thio]ethanone	quinolines		low
8-[2-(4-chloro-3,5-dimethylphenoxy)ethoxy]quinoline	quinolines		low
8-[2-(4-chloro-2,5-dimethylphenoxy)ethoxy]quinoline	quinolines		low
8-[3-(3,4-dimethylphenoxy)propoxy]quinoline	quinolines		low
2-(4-methoxyphenyl)-N-[2-(4-morpholinyl)ethyl]-4-quinolinecarboxamide	quinolines		low
1-[(7-chloro-4-quinolinyl)amino]-3-(2,4-dichlorophenyl)thiourea	organochlorine compound; quinolines		low
N-[4-[(4,6-dimethyl-2-pyrimidinyl)sulfamoyl]phenyl]-2-phenyl-4-quinolinecarboxamide	quinolines		low
3-[2-(4-fluorophenyl)-4-quinolinyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine	quinolines		low
2-(2-chlorophenyl)-N-[4-[(3,4-dimethyl-5-isoxazolyl)sulfamoyl]phenyl]-4-quinolinecarboxamide	quinolines		low
N-(2-cyanophenyl)-2-[(5,7-dibromo-8-quinolinyl)oxy]acetamide	organohalogen compound; quinolines		low
5-bromo-2-furancarboxylic acid [2-(3,4-dihydro-2H-quinolin-1-yl)-2-oxoethyl] ester	quinolines		low
3-[2-(4-chlorophenyl)-4-quinolinyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine	quinolines		low
4-[4-(2,3,5,6-Tetramethylphenyl)sulfonylpiperazine-1-carbonyl]-1H-quinolin-2-one	quinolines	anticoronaviral agent	low
N-(5-methyl-1,3,4-thiadiazol-2-yl)-2-quinolinecarboxamide	quinolines		low
4,6,8-trimethyl-1H-quinoline-2-thione	quinolines		low
4-[4-(2,3-Dimethylphenyl)piperazine-1-carbonyl]-1H-quinolin-2-one	quinolines	anticoronaviral agent	low
4-[4-[3-(Trifluoromethyl)phenyl]piperazine-1-carbonyl]-1H-quinolin-2-one	quinolines	anticoronaviral agent	low
4-ethyl-3-[2-(4-methylphenyl)-4-quinolinyl]-1H-1,2,4-triazole-5-thione	quinolines		low
1-(2-benzofuranyl)-2-[(4-methyl-2-quinolinyl)thio]ethanone	quinolines		low
N-[2-(2-Methoxyphenoxy)ethyl]-2-oxo-1H-quinoline-4-carboxamide	quinolines	anticoronaviral agent	low
2-phenyl-N-(2-piperidin-1-ylethyl)quinolin-4-amine	quinolines		low
6-(4-methoxybenzyl)-3-methyl-5,6,7,8-tetrahydroquinoline	quinolines		low
8-methoxy-4-oxo-1H-quinoline-2-carboxylic acid methyl ester	quinolines		low
N-(2-quinolinyl)cyclohexanecarboxamide	quinolines		low
LSM-28160	quinolines		low
2-(3,4-dimethoxyphenyl)quinoline	quinolines		low
N-[2-[[2-(trifluoromethyl)-4-quinolinyl]thio]ethyl]methanesulfonamide	quinolines		low
5-nitro-8-(1-pyrrolidinyl)quinoline	nitro compound; quinolines		low
8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methyl-2-quinolinone	quinolines		low
4-Methoxy-1-methyl-8-((2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methoxy)quinolin-2(1H)-one	quinolines		low
2-[4-(2,2-dimethyl-4-oxo-1,3,5,6-tetrahydrobenzo[a]phenanthridin-5-yl)-2-methoxyphenoxy]acetic acid	quinolines		low
1-[8-chloro-4-(1-naphthalenyl)-3,3a,4,9b-tetrahydrocyclopenta[c]quinolin-5-yl]ethanone	quinolines		low
7,7-dimethyl-1-(4-methylphenyl)-2,5-dioxo-N-(2-oxo-3-thiolanyl)-6,8-dihydroquinoline-3-carboxamide	quinolines		low
N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-phenyl-4-quinolinecarboxamide	quinolines		low
1-(8-quinolinylsulfonyl)-3-piperidinecarboxylic acid ethyl ester	quinolines		low
N-ethyl-N-[2-[(5-nitro-8-quinolinyl)amino]ethyl]benzenesulfonamide	nitro compound; quinolines		low
2,5-dimethoxy-n-(quinolin-3-yl)benzenesulfonamide	quinolines		low
N-(4-carbamoylphenyl)-2-(4-methoxyphenyl)-4-quinolinecarboxamide	quinolines		low
4-ethoxy-N-(3-quinolinyl)benzenesulfonamide	quinolines		low
[2-(3-chlorophenyl)-4-quinolinyl]-[4-(2-pyridinyl)-1-piperazinyl]methanone	quinolines		low
[4-(benzenesulfonyl)-1-piperazinyl]-[6-bromo-2-(2-pyridinyl)-4-quinolinyl]methanone	quinolines		low
5-chloro-7-[3-pyridinyl-(2-pyridinylamino)methyl]-8-quinolinol	organochlorine compound; quinolines		low
6-[[4-(3,4-dihydro-2H-quinolin-1-ylsulfonyl)anilino]-oxomethyl]-1-cyclohex-3-enecarboxylic acid	quinolines		low
cb 7969312	organochlorine compound; quinolines		low
LSM-18518	quinolines		low
3-methyl-N-[[(2-methyl-5-quinolinyl)amino]-sulfanylidenemethyl]benzamide	quinolines		low
2-quinolinecarboxylic acid (2-oxo-3-oxolanyl) ester	quinolines		low
3-(3,4-dihydro-2H-quinolin-1-ylmethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine	quinolines		low
[4-(2-pyridinyl)-1-piperazinyl]-[2-(3,4,5-trimethoxyphenyl)-4-quinolinyl]methanone	quinolines		low
2-(2-furanyl)-N-(2-oxolanylmethyl)-4-quinolinecarboxamide	quinolines		low
2-(3,4-dimethoxyphenyl)-4-quinolinecarboxylic acid (2-oxo-3-oxolanyl) ester	quinolines		low
1-[1-chloro-2-[(2-nitrophenyl)thio]-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinolin-8-yl]ethanone	quinolines		low
4-(6-bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline	quinolines		low
4-(6-bromo-1,3-benzodioxol-5-yl)-7,9-dimethyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline	quinolines		low
1-[4-(6-bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]ethanone	quinolines		low
N'-[2-[(6-methoxy-2-methyl-4-quinolinyl)thio]-1-oxoethyl]-2-(1-naphthalenyloxy)acetohydrazide	quinolines		low
9-(2-ethoxy-3-methoxyphenyl)-3,6,8,9-tetrahydro-2H-[1,4]dioxino[2,3-g]quinolin-7-one	quinolines		low
2-(1,5-dimethyl-4-pyrazolyl)-4-quinolinecarboxylic acid	quinolines		low
1-[(5,8-dimethyl-2-oxo-1H-quinolin-3-yl)methyl]-1-(2-furanylmethyl)-3-(2-oxolanylmethyl)thiourea	quinolines		low
1-[2-(dimethylamino)ethyl]-1-[(6-oxo-5H-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-3-(2-oxolanylmethyl)thiourea	quinolines		low
3-ethyl-1-(2-furanylmethyl)-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]thiourea	quinolines		low
1-[2-(diethylamino)ethyl]-1-[(7-oxo-3,6-dihydro-2H-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-3-(2-oxolanylmethyl)thiourea	quinolines		low
1-[(6,7-dimethoxy-2-oxo-1H-quinolin-3-yl)methyl]-1-[2-(3-methylphenyl)ethyl]-3-[3-(4-morpholinyl)propyl]thiourea	quinolines		low
N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-5-methyl-N-(thiophen-2-ylmethyl)-2,1,3-benzothiadiazole-4-sulfonamide	quinolines		low
3-butan-2-yl-1-[(6,7-dimethoxy-2-oxo-1H-quinolin-3-yl)methyl]-1-(2-phenylethyl)thiourea	quinolines		low
2-[(3,6-dimethyl-2-quinolinyl)thio]-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone	quinolines		low
3-(2,4-dimethoxyphenyl)-1-[(1-ethyl-2-pyrrolidinyl)methyl]-1-[(7-methyl-2-oxo-1H-quinolin-3-yl)methyl]thiourea	quinolines		low
4-ethoxy-N-[(6-methoxy-2-oxo-1H-quinolin-3-yl)methyl]-N-[(4-methoxyphenyl)methyl]benzamide	quinolines		low
3-(4-fluorophenyl)-1-[(6-oxo-5H-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-1-(thiophen-2-ylmethyl)urea	quinolines		low
2-[(3-cyano-8-methyl-2-quinolinyl)thio]-N-(2-oxolanylmethyl)acetamide	quinolines		low
N-(2,4-dioxo-1H-pyrimidin-5-yl)-2-[(3-ethyl-5,8-dimethyl-2-quinolinyl)thio]acetamide	quinolines		low
N-[2-(cyclohexylamino)-2-oxo-1-(6-quinolinyl)ethyl]-N-[(4-fluorophenyl)methyl]-2,3-dihydro-1,4-benzodioxin-6-carboxamide	quinolines		low
3,4-dihydro-2H-quinolin-1-yl-[4-(phenylmethyl)-5-thieno[3,2-b]pyrrolyl]methanone	quinolines		low
4-[2-(3,4-dihydro-2H-quinolin-1-yl)-2-oxoethyl]-2-methyl-5-furo[3,2-b]pyrrolecarboxylic acid methyl ester	quinolines		low
6-[(2-methoxyphenyl)methylsulfamoyl]-4-oxo-1H-quinoline-3-carboxylic acid	quinolines		low
2-[(3,5-dimethyl-4-isoxazolyl)methylthio]-4-ethyl-7,7-dimethyl-5-oxo-6,8-dihydroquinoline-3-carbonitrile	quinolines		low
4-[(1-methyl-2-oxo-4-quinolinyl)oxy]-N-(4-methyl-2-pyridinyl)butanamide	quinolines		low
N-[2-(6,7-dimethyl-2-oxo-1H-quinolin-3-yl)ethyl]-1-propanesulfonamide	quinolines		low
N-[2-(6,7-dimethyl-2-oxo-1H-quinolin-3-yl)ethyl]ethanesulfonamide	quinolines		low
N-(2-methyl-4-oxo-1-propyl-6-quinolinyl)-2-pyrazinecarboxamide	quinolines		low
3,4-dihydro-2H-quinolin-1-yl-(7-methoxy-4,5-dihydrobenzo[g][1,2]benzoxazol-3-yl)methanone	quinolines		low
4,5-dihydrobenzo[g][1,2]benzoxazol-3-yl(3,4-dihydro-2H-quinolin-1-yl)methanone	quinolines		low
9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-10-[2-(4-morpholinyl)ethyl]-4,5,7,9-tetrahydro-2H-acridine-1,8-dione	quinolines		low
2-(2,4-dimethoxyanilino)-N-[3-(4-methyl-1-piperazinyl)propyl]-4-quinolinecarboxamide	quinolines		low
1-[oxo-[4-oxo-6-[(4-propan-2-ylphenyl)sulfamoyl]-1H-quinolin-3-yl]methyl]-4-piperidinecarboxamide	aromatic amide; quinolines		low
[4-[6-(4-morpholinyl)-3-pyridazinyl]-1-piperazinyl]-(2-pyridin-4-yl-4-quinolinyl)methanone	quinolines		low
5-bromo-N-[2-(6,7-dimethyl-2-oxo-1H-quinolin-3-yl)ethyl]-2-furancarboxamide	quinolines		low
6-[(2-ethylphenyl)sulfamoyl]-N-(2-furanylmethyl)-4-oxo-1H-quinoline-3-carboxamide	aromatic amide; quinolines		low
N-ethyl-3-[4-morpholinyl(oxo)methyl]-4-oxo-N-phenyl-1H-quinoline-6-sulfonamide	aromatic amide; quinolines		low
2-ethyl-N-[2-(7-methoxy-2-oxo-1H-quinolin-3-yl)ethyl]butanamide	quinolines		low
3,4-dihydro-2H-quinolin-1-yl-[5-(4-methoxyphenyl)-3-isoxazolyl]methanone	quinolines		low
6-[(2-ethylphenyl)sulfamoyl]-4-oxo-N-(2-oxolanylmethyl)-1H-quinoline-3-carboxamide	aromatic amide; quinolines		low
N-(1,3-benzodioxol-5-yl)-2-[(1-ethyl-2-oxo-4-quinolinyl)thio]acetamide	quinolines		low
6-(1-azepanylsulfonyl)-1-ethyl-N-(2-furanylmethyl)-4-oxo-3-quinolinecarboxamide	aromatic amide; quinolines		low
N-[2-(7-methoxy-2-oxo-1H-quinolin-3-yl)ethyl]cyclopropanecarboxamide	quinolines		low
N-[3-(3,5-dimethyl-1-piperidinyl)propyl]-2-[(1-methyl-2-oxo-4-quinolinyl)oxy]acetamide	quinolines		low
1-acetyl-N-propyl-3,4-dihydro-2H-quinoline-6-sulfonamide	quinolines		low
2-(2,5-dimethoxyanilino)-N-[3-(4-morpholinyl)propyl]-4-quinolinecarboxamide	quinolines		low
3-acetyl-6-methyl-1H-quinolin-4-one	quinolines		low
2-amino-4-[4-(methylthio)phenyl]-5-oxo-1-phenyl-4,6,7,8-tetrahydroquinoline-3-carbonitrile	quinolines		low
N-[1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-1-methyl-4-oxo-6-(1-pyrrolidinylsulfonyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
N-butan-2-yl-6-[(4-ethoxyphenyl)sulfamoyl]-4-oxo-1H-quinoline-3-carboxamide	aromatic amide; quinolines		low
1-methyl-6-[(4-methyl-1-piperidinyl)sulfonyl]-3-[oxo(1-piperidinyl)methyl]-4-quinolinone	aromatic amide; quinolines		low
1-methyl-N-(2-methylcyclohexyl)-4-oxo-6-(1-pyrrolidinylsulfonyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
8-(2-propoxyphenyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]quinolin-6-one	quinolines		low
2,6-dimethyl-4-(4-phenyl-2-quinolinyl)morpholine	quinolines		low
quinoxyfen	aromatic ether; monofluorobenzenes; organochlorine compound; quinolines	antifungal agrochemical	low
N-[4-(methoxymethyl)-6-methyl-2-oxo-1H-quinolin-7-yl]cyclopropanecarboxamide	quinolines		low
N-[2-(4-morpholinyl)ethyl]-2-(4-propan-2-yloxyphenyl)-4-quinolinecarboxamide	quinolines		low
5-chloro-7-[1-piperidinyl(2-pyridinyl)methyl]-8-quinolinol	organochlorine compound; quinolines		low
4-(3,4-dihydro-2H-quinolin-1-ylsulfonyl)-N-(5-ethyl-1,3,4-oxadiazol-2-yl)benzamide	quinolines		low
5-chloro-7-[(4-ethyl-1-piperazinyl)-(3-pyridinyl)methyl]-8-quinolinol	organochlorine compound; quinolines		low
N-[2-(6,7-dimethyl-2-oxo-1H-quinolin-3-yl)ethyl]-2-thiophenecarboxamide	quinolines		low
6-bromo-2-(4-methylphenyl)-N-[(1-methyl-4-pyrazolyl)methyl]-4-quinolinecarboxamide	quinolines		low
3-acetyl-6-bromo-2-methyl-4-quinolinecarboxylic acid	quinolines		low
2-thiophen-2-yl-4-quinolinecarboxylic acid (2-oxo-3-oxolanyl) ester	quinolines		low
6,8-dibromo-2-thiophen-2-ylquinoline	organohalogen compound; quinolines		low
N-(4-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide	quinolines		low
2-(4-methoxyphenyl)-N-[2-(4-morpholinyl)-5-(4-morpholinylsulfonyl)phenyl]-4-quinolinecarboxamide	quinolines		low
N-(3-methylbutyl)-6-(4-morpholinylsulfonyl)-2-pyridin-4-yl-4-quinolinecarboxamide	quinolines		low
2-(4-ethoxyphenyl)-N-[3-(1-imidazolyl)propyl]-4-quinolinecarboxamide	quinolines		low
7-ethoxy-3-[5-(2-furanyl)-2-methylsulfonyl-3,4-dihydropyrazol-3-yl]-1H-quinolin-2-one	quinolines		low
2-amino-4-(5-bromo-2-thiophenyl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile	quinolines		low
N-[(5-quinolinylamino)-sulfanylidenemethyl]benzamide	quinolines		low
7-[(3-hydroxy-3,4-dihydro-2H-benzo[h]quinolin-1-yl)methyl]-5-thiazolo[3,2-a]pyrimidinone	quinolines		low
N-(3,5-dichloro-2-pyridinyl)-2-[(4-methyl-2-quinolinyl)thio]propanamide	quinolines		low
2-amino-1-(dimethylamino)-4-(1-naphthalenyl)-5-oxo-7-phenyl-4,6,7,8-tetrahydroquinoline-3-carbonitrile	naphthalenes; quinolines		low
2-(2-chlorophenyl)-N-[3-(3,4,5,6-tetrahydro-2H-azepin-7-ylsulfamoyl)phenyl]-4-quinolinecarboxamide	quinolines		low
2-phenyl-4-quinolinecarboxylic acid [2-[2-chloro-5-(dimethylsulfamoyl)anilino]-2-oxoethyl] ester	quinolines		low
2-amino-4-(3,4-dimethoxyphenyl)-7,7-dimethyl-5-oxo-1-(3-pyridinyl)-6,8-dihydro-4H-quinoline-3-carbonitrile	quinolines		low
2-(1-naphthalenyl)-4-quinolinecarboxylic acid [1-[(1,5-dimethyl-3-oxo-2-phenyl-4-pyrazolyl)amino]-1-oxopropan-2-yl] ester	naphthalenes; quinolines		low
2-(5-bromo-2-thiophenyl)-N-(4-methyl-1-piperazinyl)-4-quinolinecarboxamide	quinolines		low
[3,5-bis(difluoromethyl)-5-hydroxy-4H-pyrazol-1-yl]-[2-(4-propan-2-ylphenyl)-4-quinolinyl]methanone	quinolines		low
[2-(3,4-dimethylphenyl)-4-quinolinyl]-(1-piperidinyl)methanone	quinolines		low
sb 408124	organohalogen compound; quinolines		low
2-(4-fluorophenyl)-4-quinolinecarboxylic acid [2-oxo-2-(2-oxolanylmethylamino)ethyl] ester	quinolines		low
5-[3-(2-chloro-6-methoxy-3-quinolinyl)-5-(2-furanyl)-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid	organochlorine compound; quinolines		low
[3-(2-chloro-6-ethoxy-3-quinolinyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone	organochlorine compound; quinolines		low
flosequinan	quinolines		low
N-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide	quinolines		low
1-[(4-fluorophenyl)-oxomethyl]-3-[(5-methyl-[1,2,4]triazolo[4,3-a]quinolin-1-yl)thio]-2-azepanone	quinolines		low
7,7-dimethyl-1-(4-methylphenyl)-N-[3-(4-morpholinyl)propyl]-2,5-dioxo-6,8-dihydroquinoline-3-carboxamide	quinolines		low
2-(4-bromophenyl)-4-quinolinecarboxylic acid (2-oxo-3-oxolanyl) ester	quinolines		low
N-(5-methyl-3-isoxazolyl)-2-(4-propan-2-yloxyphenyl)-4-quinolinecarboxamide	quinolines		low
2-methyl-1-cyclopropanecarboxylic acid [5-[2-(3,4-dimethoxyphenyl)-4-quinolinyl]-1,3,4-oxadiazol-2-yl]methyl ester	quinolines		low
1-(4-bromophenyl)-1'-methyl-6'-nitro-2'-phenylspiro[1,3-diazinane-5,3'-2,4-dihydroquinoline]-2,4,6-trione	quinolines		low
1-phenylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1H-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione	quinolines		low
LSM-4833	quinolines		low
1-[[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]methyl]-4-methyl-2-quinolinone	quinolines		low
4-[[2-(4-ethyl-1-piperazinyl)-2-oxoethyl]thio]-1-methyl-2-quinolinone	quinolines		low
2-[2-(7-methoxy-2-oxo-1H-quinolin-3-yl)ethyl]isoindole-1,3-dione	quinolines		low
montelukast	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist	low
l 660,711	quinolines		low
pitavastatin	cyclopropanes; dihydroxy monocarboxylic acid; monofluorobenzenes; quinolines; statin (synthetic)	antioxidant	low
1-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)sulfonyl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-piperidinecarboxamide	quinolines		low
1-(3-amino-7-methoxy-1-pyrazolo[3,4-b]quinolinyl)-2-(2-methoxyphenyl)ethanone	quinolines		low
N-(2-ethoxyphenyl)-1-(8-quinolinylsulfonyl)-3-piperidinecarboxamide	quinolines		low
N-[2-(1-pyrrolidinyl)ethyl]-8-quinolinesulfonamide	quinolines		low
N-[[4-(dimethylamino)phenyl]methyl]-2-[methyl(8-quinolinylsulfonyl)amino]acetamide	quinolines		low
N-[(2-methoxyphenyl)methyl]-1-(8-quinolinylsulfonyl)-4-piperidinecarboxamide	quinolines		low
evocarpine	quinolines		low
4-[(3aR,4S,9bS)-8-[(4-methoxyphenyl)sulfamoyl]-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl]benzoic acid	quinolines		low
Bucharaine	quinolines		low
1,1'-diethyl-2,2'-cyanine	1,1'-diethyl-2,2'-cyanine; quinolines		low
penicillin v	1,1'-diethyl-2,2'-cyanine; quinolines		low
salubrinal	aminal; organochlorine compound; quinolines; secondary carboxamide; thioureas		low
2-(1-ethyl-4-pyrazolyl)-4-quinolinecarboxylic acid	quinolines		low
4-[2-(3,4-dimethoxyphenyl)ethylamino]-2-oxo-1H-quinoline-3-carboxaldehyde	quinolines		low
sb 222200	quinolines		low
l 689560	quinolines		low
sb 218795	quinolines		low
1-(3-amino-7-methoxy-1-pyrazolo[3,4-b]quinolinyl)-2-(4-chlorophenyl)ethanone	quinolines		low
N-butyl-N-phenyl-8-quinolinesulfonamide	quinolines		low
ik 682	hydroxamic acid; pyrrolidin-2-ones; quinolines		low
N-(3-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide	quinolines		low
3-butyl-10-phenylpyrimido[4,5-b]quinoline-2,4-dione	quinolines		low
N-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide	quinolines		low
N-[2-(3-methoxyphenyl)-4-[(4-methoxyphenyl)methoxy]-6-quinolinyl]-3-pyridinecarboxamide	quinolines		low
pq 401	quinolines		low
3-(4-ethoxyphenyl)-1-[3-(4-morpholinyl)propyl]-1-[(1-propyl-3,4-dihydro-2H-quinolin-6-yl)methyl]urea	quinolines		low
lenvatinib	aromatic amide; aromatic ether; cyclopropanes; monocarboxylic acid amide; monochlorobenzenes; phenylureas; quinolines	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; fibroblast growth factor receptor antagonist; orphan drug; vascular endothelial growth factor receptor antagonist	low
ozenoxacin	quinolines		low
jte 907	aromatic amide; quinolines		low
hki 272	nitrile; quinolines	antineoplastic agent; tyrosine kinase inhibitor	low
tan 67	quinolines		low
ly-2157299	aromatic amide; methylpyridines; monocarboxylic acid amide; pyrrolopyrazole; quinolines	antineoplastic agent; TGFbeta receptor antagonist	low
5-iodo-6-nitro-2-piperazinylquinoline	nitro compound; quinolines		low
besifloxacin	quinolines		low
ofloxacin n-oxide	quinolines		low
crenolanib	aminopiperidine; aromatic ether; benzimidazoles; oxetanes; quinolines; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
ki11502	aromatic ether; benzamides; quinolines; thioureas	antineoplastic agent; apoptosis inducer; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
pf 573228	quinolines		low
osi 906	cyclobutanes; quinolines		low
dactolisib	imidazoquinoline; nitrile; quinolines; ring assembly; ureas	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor	low
nemonoxacin	quinolines		low
[9-(benzenesulfonyl)-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-yl]-(4-methylphenyl)methanone	aromatic ketone; quinolines		low
1-(phenylmethyl)-4-quinolinone	quinolines		low
CDN1163	aromatic ether; quinolines; secondary carboxamide	SERCA activator	low
3,5-dimethoxy-N-[1-[oxo(thiophen-2-yl)methyl]-3,4-dihydro-2H-quinolin-6-yl]benzamide	quinolines		low
picogreen	benzothiazoles; cyanine dye; quinolines; tertiary amine	fluorescent dye	low
1-[(1-ethyl-3,4-dihydro-2H-quinolin-6-yl)methyl]-3-(3-methylphenyl)-1-[2-(4-morpholinyl)ethyl]thiourea	quinolines		low
1-[(1-ethyl-3,4-dihydro-2H-quinolin-6-yl)methyl]-3-(4-methylphenyl)-1-[2-(4-morpholinyl)ethyl]thiourea	quinolines		low
1-[(1-ethyl-3,4-dihydro-2H-quinolin-6-yl)methyl]-3-(3-methoxyphenyl)-1-[2-(4-morpholinyl)ethyl]thiourea	quinolines		low
2-[4-[(6-ethoxy-2-quinolinyl)methyl]-1-(3-thiophenylmethyl)-2-piperazinyl]ethanol	quinolines		low
nk 5	organic iodide salt; quinolines	fluorochrome	low
peniprequinolone	quinolines		low
pf 04217903	quinolines		low
sgx 523	aryl sulfide; biaryl; pyrazoles; quinolines; triazolopyridazine	c-Met tyrosine kinase inhibitor; nephrotoxic agent	low
AMG-208	aromatic ether; quinolines; triazolopyridazine	antineoplastic agent; c-Met tyrosine kinase inhibitor	low
lucitanib	aromatic ether; cyclopropanes; naphthalenecarboxamide; primary amino compound; quinolines	antineoplastic agent; fibroblast growth factor receptor antagonist; vascular endothelial growth factor receptor antagonist	low
dcc-2036	organofluorine compound; phenylureas; pyrazoles; pyridinecarboxamide; quinolines	tyrosine kinase inhibitor	low
cabozantinib	aromatic ether; dicarboxylic acid diamide; organofluorine compound; quinolines	antineoplastic agent; tyrosine kinase inhibitor	low
pf 750	quinolines		low
gsk 2126458	aromatic ether; difluorobenzene; pyridazines; pyridines; quinolines; sulfonamide	anticoronaviral agent; antineoplastic agent; autophagy inducer; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor; radiosensitizing agent	low
N-[(8-methoxy-5-nitro-7-quinolinyl)-thiophen-2-ylmethyl]propanamide	nitro compound; quinolines		low
iwr-1 endo	benzamides; bridged compound; dicarboximide; quinolines	axin stabilizer; Wnt signalling inhibitor	low
jnj38877605	quinolines		low
torin 1	N-acylpiperazine; N-arylpiperazine; organofluorine compound; pyridoquinoline; quinolines	antineoplastic agent; mTOR inhibitor	low
DMH1	aromatic ether; pyrazolopyrimidine; quinolines	antineoplastic agent; bone morphogenetic protein receptor antagonist; protein kinase inhibitor	low
1-butyl-4-hydroxy-N-(3-methyl-2-pyridinyl)-2-oxo-3-quinolinecarboxamide	aromatic amide; quinolines		low
4-hydroxy-2-oxo-1-propyl-N-(pyridin-4-ylmethyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
4-hydroxy-1-methyl-3-(phenylthio)-1,2-dihydroquinolin-2-one	quinolines		low
LSM-23865	quinolines		low
N-[(4-chlorophenyl)methyl]-4-hydroxy-2-oxo-1-prop-2-enyl-3-quinolinecarboxamide	aromatic amide; quinolines		low
4-hydroxy-1-methyl-2-oxo-N-(4-oxo-2-propyl-3-quinazolinyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
1-butyl-N-[(4-chlorophenyl)methyl]-4-hydroxy-2-oxo-3-quinolinecarboxamide	aromatic amide; quinolines		low
N'-[(2-chlorophenyl)-oxomethyl]-1-ethyl-4-hydroxy-2-oxo-3-quinolinecarbohydrazide	aromatic amide; quinolines		low
4-hydroxy-1-methyl-N'-[(3-methylphenyl)-oxomethyl]-2-oxo-3-quinolinecarbohydrazide	aromatic amide; quinolines		low
Bucharidine	quinolines		low
4-hydroxy-2-oxo-1-prop-2-enyl-N-(3-pyridinyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
LSM-23565	aromatic amide; quinolines		low
l 701324	quinolines		low
1-ethyl-4-hydroxy-2-oxo-N'-(1-oxoheptyl)-3-quinolinecarbohydrazide	aromatic amide; quinolines		low
2-[[[4-hydroxy-2-oxo-1-(phenylmethyl)-3-quinolinyl]-oxomethyl]amino]acetic acid	quinolines		low
1-ethyl-4-hydroxy-2-oxo-N'-(1-oxodecyl)-3-quinolinecarbohydrazide	aromatic amide; quinolines		low
LSM-31922	aromatic amide; quinolines		low
1-ethyl-4-hydroxy-2-oxo-N-(3-pyridinylmethyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
N-(1H-benzimidazol-2-yl)-1-ethyl-4-hydroxy-2-oxo-3-quinolinecarboxamide	aromatic amide; quinolines		low
N-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-oxo-1-propyl-3-quinolinecarboxamide	aromatic amide; quinolines		low
4-hydroxy-N-(2-methyl-4-oxo-3-quinazolinyl)-1-(2-methylpropyl)-2-oxo-5,6,7,8-tetrahydroquinoline-3-carboxamide	aromatic amide; quinolines		low
4-hydroxy-1-(2-methylpropyl)-2-oxo-N-[4-oxo-2-(phenylmethyl)-3-quinazolinyl]-5,6,7,8-tetrahydroquinoline-3-carboxamide	aromatic amide; quinolines		low
4-hydroxy-2-oxo-1-pentyl-N-(2-pyridinylmethyl)-3-quinolinecarboxamide	aromatic amide; quinolines		low
N-[2-(4-chlorophenyl)ethyl]-4-hydroxy-2-oxo-1-propyl-3-quinolinecarboxamide	aromatic amide; quinolines		low
4-hydroxy-1,7,7-trimethyl-3-(2,4,6-trimethylphenyl)-6,8-dihydroquinoline-2,5-dione	quinolines		low
sybr green i	benzothiazolium ion; cyanine dye; quinolines; tertiary amine	fluorescent dye	low
9-(3,5-dimethoxyphenyl)-1-[4-(1-piperazinyl)-3-(trifluoromethyl)phenyl]-2-benzo[h][1,6]naphthyridinone	quinolines		low
GSK1059615	pyridines; quinolines; thiazolidinone	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor	low
naphthalene	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component	low
2-(6-methoxy-2-naphthalenyl)propanoic acid	naphthalenes		low
N-(2-aminoethyl)-5-chloro-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
butenafine	naphthalenes; tertiary amine	antifungal drug; EC 1.14.13.132 (squalene monooxygenase) inhibitor	low
hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylester	acetate ester; naphthalenes; organic phosphonate	tyrosine kinase inhibitor	low
1-(2-naphthalenyl)-3-[(phenylmethyl)-propan-2-ylamino]-1-propanone	naphthalenes		low
1-(2-naphthalenyl)-2-propen-1-one	naphthalenes		low
ml 9	naphthalenes; sulfonic acid derivative		low
w 12	naphthalenes; sulfonic acid derivative		low
n-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide	naphthalenes; organochlorine compound; primary amino compound; sulfonamide		low
n-(6-aminohexyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
nafoxidine	benzenes; naphthalenes; ring assembly		low
nafronyl	naphthalenes		low
naphazoline	naphthalenes		low
pronethalol	naphthalenes		low
propranolol	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic	low
sc-10	naphthalenes; sulfonic acid derivative		low
N,6,6-trimethyl-N-(1-naphthalenylmethyl)-1-hept-2-en-4-ynamine	naphthalenes		low
carbaryl	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant	low
naphthaleneacetamide	naphthalenes; primary carboxamide	synthetic auxin	low
1-naphthylphenylamine	naphthalenes		low
2-naphthalenethiol	naphthalenes		low
2-methoxynaphthalene	naphthalenes		low
bromelia	naphthalenes		low
neozone	naphthalenes		low
benzo(j)fluoranthene	naphthalenes		low
benzo(k)fluoranthene	naphthalenes		low
chlornaphazin	naphthalenes		low
methallenestril	naphthalenes		low
1,5-naphthylene di-isocyanate	naphthalenes		low
nitrosocarbaryl	carbamate ester; naphthalenes; nitroso compound	carcinogenic agent; mutagen	low
devrinol	aromatic ether; monocarboxylic acid amide; naphthalenes		low
2,6-diisopropylnaphthalene	naphthalenes	agrochemical; plant growth retardant	low
nadoxolol	naphthalenes		low
naftifine	allylamine antifungal drug; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; sterol biosynthesis inhibitor	low
tolrestat	naphthalenes	EC 1.1.1.21 (aldehyde reductase) inhibitor	low
lonapalene	naphthalenes; organochlorine compound		low
fananserin	naphthalenes; sulfonic acid derivative		low
aptiganel	naphthalenes		low
5-Aminoacenaphthene	naphthalenes		low
dapoxetine	naphthalenes		low
2-naphthyl sulfate	aryl sulfate; naphthalenes		low
bexarotene	benzoic acids; naphthalenes; retinoid	antineoplastic agent	low
1,8-bis(dimethylamino)naphthalene	naphthalenes		low
1-(1,2-dihydroacenaphthylen-5-yl)ethanone	naphthalenes		low
1,1,6-trimethyl-1,2-dihydronaphthalene	naphthalenes		low
11-(dansylamino)undecanoic acid	naphthalenes; sulfonic acid derivative		low
5-(dimethylamino)-n-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
n-(6-phenylhexyl)-5-chloro-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
xaliproden hydrochloride	naphthalenes		low
xaliproden	(trifluoromethyl)benzenes; naphthalenes; tertiary amino compound; tetrahydropyridine	serotonergic agonist	low
1-naphthylacetylspermine	naphthalenes		low
cinacalcet	(trifluoromethyl)benzenes; naphthalenes; secondary amino compound	calcimimetic; P450 inhibitor	low
birb 796	aromatic ether; morpholines; naphthalenes; pyrazoles; ureas	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; immunomodulator	low
5-(2-naphthalenylmethylidene)-1,3-diazinane-2,4,6-trione	naphthalenes		low
6,11-dioxo-12-naphtho[2,3-b]indolizinecarboxylic acid ethyl ester	naphthalenes		low
acetic acid (4-acetyloxy-6,7-dimethyl-5,8-dihydronaphthalen-1-yl) ester	naphthalenes		low
korupensamine-b	isoquinolines; naphthalenes		low
dioncophylline a	biaryl; isoquinoline alkaloid; isoquinolines; methoxynaphthalene; methylnaphthalenes; naphthalenes	antifungal agent; antimalarial; metabolite; molluscicide	low
1-[(4-fluoro-1-naphthalenyl)sulfonyl]piperidine	naphthalenes; sulfonic acid derivative		low
6-tert-butylnaphthalene-2,3-dicarbonitrile	naphthalenes		low
5-(diethylsulfamoyl)-3-hydroxy-2-naphthalenecarboxylic acid	naphthalenes; sulfonic acid derivative		low
2,6-dimethyl-4-[1-(2-naphthalenylsulfonyl)-4-piperidinyl]morpholine	naphthalenes; sulfonic acid derivative		low
1,3-dimethyl-6-(1-naphthalenyl)pyrrolo[3,4-d]pyrimidine-2,4-dione	naphthalenes		low
5-(4-methyl-1-piperidinyl)-2-(1-naphthalenylmethyl)-4-oxazolecarbonitrile	naphthalenes		low
5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-(1-naphthalenylmethyl)-4-oxazolecarbonitrile	naphthalenes		low
3-methyl-6-(1-naphthalenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole	naphthalenes; triazolothiadiazole		low
N-(1,2-dihydroacenaphthylen-5-yl)methanesulfonamide	naphthalenes		low
N,N-diethyl-2-oxo-1H-benzo[cd]indole-6-sulfonamide	naphthalenes; sulfonic acid derivative		low
spiro[1,3-dihydroperimidine-2,1'-cycloheptane]	naphthalenes		low
2-(3-nitrophenyl)-2,3-dihydro-1H-perimidine	naphthalenes		low
2-phenylmethoxy-1-naphthalenecarboxaldehyde	naphthalenes		low
alpha-naphthyl thiourea	naphthalenes		low
4-[(2-methoxy-1-naphthalenyl)methyl]thiomorpholine	naphthalenes		low
N-(3-methoxyphenyl)-2-benzo[cd]indolamine	naphthalenes		low
LSM-21110	naphthalenes; sulfonic acid derivative		low
4-[(6-methoxy-2-naphthalenyl)sulfonyl]morpholine	naphthalenes; sulfonic acid derivative		low
LSM-28278	naphthalenes		low
4-(2-naphthalenylmethyl)-1-piperazinecarboxylic acid ethyl ester	naphthalenes		low
6-(4-morpholinyl)naphthalene-2,3-dicarbonitrile	naphthalenes		low
N-(1-naphthalenyl)-4-(phenylmethyl)-1-piperazinecarboxamide	naphthalenes		low
3,5-dimethyl-1-[(7-methyl-2-naphthalenyl)sulfonyl]pyrazole	naphthalenes; sulfonic acid derivative		low
2-methyl-N-(2-naphthalenyl)-3-furancarboxamide	naphthalenes		low
4-chloro-N-(2-pyridinyl)-1-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
3-(2-benzo[cd]indolylamino)benzoic acid	naphthalenes		low
4-(2-naphthalenyloxymethyl)-2-thiazolamine	naphthalenes		low
1-(1-naphthalenylmethoxy)benzotriazole	naphthalenes		low
3-chloro-4,5-dimethoxy-N-(1-naphthalenylmethyl)benzamide	naphthalenes		low
1-[[2-(4-chlorophenyl)-1-oxoethyl]amino]-3-(1-naphthalenyl)urea	naphthalenes		low
1-methyl-N-(2-naphthalenyl)-5-benzotriazolecarboxamide	naphthalenes		low
N-(1-naphthalenyl)-5-pyridin-4-yl-1,3,4-thiadiazol-2-amine	naphthalenes		low
1-methyl-2-oxo-N-(2-pyridinyl)-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
pyrabactin	naphthalenes; organobromine compound; pyridines; sulfonamide	abscisic acid receptor agonist; hormone; plant growth regulator	low
1-ethyl-2-oxo-N-(2-pyridinylmethyl)-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
N-[(1,2-dihydroacenaphthylen-5-ylamino)-sulfanylidenemethyl]-2-phenoxyacetamide	naphthalenes		low
1-(4-bromophenyl)-4-[1-naphthalenyl(oxo)methyl]-3-pyrazolecarboxylic acid ethyl ester	carbonyl compound; naphthalenes		low
1-(1,2,3-benzothiadiazol-5-yl)-3-(1-naphthalenyl)urea	naphthalenes		low
1-(4-methylphenyl)sulfonyl-4-(2-naphthalenylsulfonyl)-1,4-diazepane	naphthalenes; sulfonic acid derivative		low
N2,N2-dimethyl-6-[[[1-(1-naphthalenyl)-5-tetrazolyl]thio]methyl]-1,3,5-triazine-2,4-diamine	naphthalenes		low
terbinafine	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor	low
1-ethyl-N-[3-(4-morpholinyl)propyl]-2-oxo-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
N-[4-(4-morpholinyl)phenyl]-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
4-fluorobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
4-bromobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
2-benzofurancarboxylic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
N-(5-methyl-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-2-yl)-2-(2-naphthalenyloxy)acetamide	naphthalenes		low
thiocyanic acid [2-(1-naphthalenyl)-2-oxoethyl] ester	naphthalenes		low
2-[2-(1-naphthalenyloxy)ethylthio]pyrimidine	naphthalenes		low
N-[2-(1-naphthalenyl)-1,3-benzoxazol-5-yl]-1H-1,2,4-triazole-5-carboxamide	naphthalenes		low
N-(2-naphthalenyl)-2-[[6-[[[2-(2-naphthalenylamino)-2-oxoethyl]thio]methyl]-2-pyridinyl]methylthio]acetamide	naphthalenes		low
1-(1-naphthalenylmethyl)-3-phenylurea	naphthalenes		low
N'-(3,4-dihydro-2H-pyrrol-5-yl)-2-(2-naphthalenylamino)acetohydrazide	naphthalenes		low
N-butyl-N-methyl-2-benzo[cd]indolamine	naphthalenes		low
N-(5-methyl-3-isoxazolyl)-2-(2-naphthalenylthio)acetamide	naphthalenes		low
LSM-19724	naphthalenes; sulfonic acid derivative		low
N-(3-chloro-2-quinoxalinyl)-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
2-(2-naphthalenylsulfonylamino)acetic acid [2-(2,5-dimethyl-1-phenyl-3-pyrrolyl)-2-oxoethyl] ester	naphthalenes; sulfonic acid derivative		low
5-(1-naphthalenylamino)-3H-1,3,4-thiadiazole-2-thione	naphthalenes		low
4-(3,5-dichloro-4-pyridinyl)-N-(1-naphthalenyl)-1,4-diazepane-1-carboxamide	naphthalenes		low
2-(1-naphthalenyl)-N-[2,2,2-trichloro-1-[[(2-chloroanilino)-sulfanylidenemethyl]amino]ethyl]acetamide	naphthalenes		low
acetic acid [4-[acetyl-(4-chlorophenyl)sulfonylamino]-1-naphthalenyl] ester	naphthalenes		low
2,2-dibromo-1-methyl-N-(2-naphthalenyl)-1-cyclopropanecarboxamide	naphthalenes		low
N'-[2-(1-naphthalenyloxy)-1-oxoethyl]-2-oxolanecarbohydrazide	naphthalenes		low
N-[3-(3,5-dimethyl-1-pyrazolyl)-2-hydroxypropyl]-N-(4-methylphenyl)-2-naphthalenesulfonamide	naphthalenes; sulfonic acid derivative		low
1-[2-furanyl(oxo)methyl]-6-(1-pyrrolidinylsulfonyl)-2-benzo[cd]indolone	naphthalenes; sulfonic acid derivative		low
2-(2-bromophenyl)-2,3-dihydro-1H-perimidine	naphthalenes		low
acetic acid [1-[(3-nitrophenyl)-(1-oxopentylamino)methyl]-2-naphthalenyl] ester	naphthalenes		low
4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]-2-butyn-1-ol	naphthalenes		low
N-(2-methoxyethyl)-1-methyl-2-oxo-6-benzo[cd]indolesulfonamide	naphthalenes; sulfonic acid derivative		low
3-(5-methyl-2-furanyl)-5-[1-(2-naphthalenylsulfonyl)-3-piperidinyl]-1,2,4-oxadiazole	naphthalenes; sulfonic acid derivative		low
(7-methoxy-4,5-dihydrobenzo[g][1,2]benzoxazol-3-yl)-(4-morpholinyl)methanone	naphthalenes		low
1-(1-naphthalenyl)-3-[3-(1-pyrrolidinyl)propyl]urea	naphthalenes		low
N-[3-(1-imidazolyl)propyl]-7-methoxy-4,5-dihydrobenzo[g][1,2]benzoxazole-3-carboxamide	naphthalenes		low
7-methoxy-4,5-dihydro-2H-benzo[g]indazole-3-carboxylic acid	naphthalenes		low
(1R,2R)-2-[(R)-(diphenylphosphorylamino)-phenylmethyl]-N-(2-naphthalenyl)-1-cyclopropanecarboxamide	naphthalenes		low
5-methyl-N-[(S)-[(1S,2R)-1-methyl-2-[(2R)-1-(2-naphthalenylamino)-1-oxopropan-2-yl]cyclopropyl]-phenylmethyl]-3-isoxazolecarboxamide	naphthalenes		low
2,5-dimethyl-N-[(S)-[(1S,2R)-1-methyl-2-[(2R)-1-(2-naphthalenylamino)-1-oxopropan-2-yl]cyclopropyl]-phenylmethyl]-3-pyrazolecarboxamide	naphthalenes		low
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline	naphthalenes; sulfonic acid derivative		low
2-(1-naphthalenyl)acetic acid [2-[4-chloro-3-(dimethylsulfamoyl)anilino]-2-oxoethyl] ester	naphthalenes		low
1,1-dimethyl-3-[3-(4-morpholinyl)propyl]-3-(1-naphthalenylmethyl)urea	naphthalenes		low
N-(4-ethoxyphenyl)sulfonyl-N-(2-oxo-5-benzo[g][1,3]benzoxathiolyl)-2-furancarboxamide	naphthalenes		low
N-[2-(3,4-dimethoxyphenyl)ethyl]-4-dimethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolamine	naphthalenes		low
4-[4-dimethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolyl]morpholine	naphthalenes		low
4-[4-diethoxyphosphoryl-2-(1-naphthalenyl)-5-oxazolyl]morpholine	naphthalenes		low
2-[(1-methyl-2-imidazolyl)thio]-1-(2-naphthalenyl)ethanone	naphthalenes		low
5-methyl-4-[(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)-[1-(1-naphthalenylmethyl)-3-indolyl]methyl]-1,2-dihydropyrazol-3-one	naphthalenes		low
N-(1-dibutoxyphosphoryl-4-oxo-1-naphthalenyl)benzenesulfonamide	naphthalenes		low
4-dimethoxyphosphoryl-2-(1-naphthalenyl)-N-(phenylmethyl)-5-oxazolamine	naphthalenes		low
4-chlorobenzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
4-amino-5-cyano-2-(1-naphthalenylmethylthio)-3-azaspiro[5.5]undeca-2,4-diene-1-carboxamide	naphthalenes		low
N-[[[2-(2-naphthalenyloxy)-1-oxopropyl]hydrazo]-sulfanylidenemethyl]-2-furancarboxamide	naphthalenes		low
(4-chloro-1-ethyl-3-pyrazolyl)-[3-(2-hydroxyphenyl)-5-(2-naphthalenyl)-3,4-dihydropyrazol-2-yl]methanone	naphthalenes		low
N-(4-methoxyphenyl)sulfonyl-N-(2-oxo-5-benzo[g][1,3]benzoxathiolyl)-2-furancarboxamide	naphthalenes		low
4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid	benzoic acids; naphthalenes; retinoid	antineoplastic agent; retinoic acid receptor agonist; teratogenic agent	low
cgp 71683 a	naphthalenes; sulfonic acid derivative		low
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one	naphthalenes		low
2-methyl-5-[(2-oxo-1H-benzo[cd]indol-6-yl)sulfonylamino]-3-benzofurancarboxylic acid butyl ester	naphthalenes; sulfonic acid derivative		low
N'-(1-methyl-4-pyrazolo[3,4-d]pyrimidinyl)-2-(1-naphthalenyl)acetohydrazide	naphthalenes		low
1-(3-ethylphenyl)-3-(1-naphthalenyl)thiourea	naphthalenes		low
ws-5995 c	benzenes; naphthalenes; ring assembly		low
np 031112	benzenes; naphthalenes; thiadiazolidine	anti-inflammatory agent; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent	low
(6-methoxy-2-naphthalenyl)-[1-[(2-methyl-5-thiazolyl)methyl]-3-piperidinyl]methanone	naphthalenes		low
1,2-dihydroacenaphthylen-5-yl-[1-[(6-methyl-2-pyridinyl)methyl]-3-piperidinyl]methanone	naphthalenes		low
1,2-dihydroacenaphthylen-5-yl-[1-(2-pyridinylmethyl)-3-piperidinyl]methanone	naphthalenes		low
1-[3-[(6-methoxy-2-naphthalenyl)-oxomethyl]-1-piperidinyl]-2-[(5-methyl-1,3,4-oxadiazol-2-yl)thio]ethanone	naphthalenes		low
4-[[(4S)-2-amino-3-[2-(1-naphthalenyl)ethyl]-4,5-dihydroimidazol-4-yl]methyl]phenol	naphthalenes		low
[5-[(4-methoxy-1-naphthalenyl)oxymethyl]-3-isoxazolyl]-(4-methoxy-1-piperidinyl)methanone	naphthalenes		low
GRL-0617	benzamides; naphthalenes; secondary carboxamide; substituted aniline	anticoronaviral agent; protease inhibitor	low
N-(1-naphthalenylmethyl)-2-thiophenecarboxamide	naphthalenes		low
(1-(4-(naphthalen-2-yl)pyrimidin-2-yl)piperidin-4-yl)methanamine	naphthalenes		low
N-[4-cyano-2-(1-naphthalenyl)-5-oxazolyl]acetamide	naphthalenes		low
2-[(4-methylphenyl)methylthio]-5-(1-naphthalenyl)-1,3,4-oxadiazole	naphthalenes		low
5-amino-2-(1-naphthalenyl)-4-oxazolecarbonitrile	naphthalenes		low
4-(dimethylamino)benzoic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
1H-imidazole-5-carboxylic acid 4-[[5-(1-naphthalenyl)-1,3,4-oxadiazol-2-yl]thio]but-2-ynyl ester	naphthalenes		low
N-[(2R,3S)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(1-naphthalenylamino)-oxomethyl]amino]methyl]-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]-2-phenylacetamide	naphthalenes		low
KOM70144	acetamides; benzamides; naphthalenes; secondary carboxamide	anticoronaviral agent; protease inhibitor	low
lesinurad	aryl sulfide; cyclopropanes; monocarboxylic acid; naphthalenes; organobromine compound; triazoles	uricosuric drug	low
difenacoum	benzenes; naphthalenes; ring assembly		low
bromfenacoum	benzenes; naphthalenes; ring assembly		low
flocoumafen	benzenes; naphthalenes; ring assembly		low
abt-333	aromatic ether; naphthalenes; pyrimidone; sulfonamide	antiviral drug; nonnucleoside hepatitis C virus polymerase inhibitor	low
bromhexine	organobromine compound; substituted aniline; tertiary amino compound	mucolytic	low
bromodiphenhydramine	organobromine compound; tertiary amino compound	antimicrobial agent; H1-receptor antagonist; muscarinic antagonist	low
bromisovalum	N-acylurea; organobromine compound		low
liquid crystal polymer	conazole fungicide; dichlorobenzene; organobromine compound; oxolanes; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor	low
halothane	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic	low
nsc 664704	indolobenzazepine; lactam; organobromine compound	cardioprotective agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; geroprotector	low
naled	dialkyl phosphate; organobromine compound; organochlorine compound; organophosphate insecticide	acaricide; agrochemical; antibacterial agent; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor	low
pipobroman	N-acylpiperazine; organobromine compound; tertiary carboxamide	alkylating agent; antineoplastic agent	low
sulfobromophthalein	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye	low
tribromoethanol	alcohol; organobromine compound		low
bromthymol blue	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; polyphenol; sultone	acid-base indicator; dye; two-colour indicator	low
brompheniramine	organobromine compound; pyridines	anti-allergic agent; H1-receptor antagonist	low
4-bromophenyl phenyl ether	aromatic ether; organobromine compound		low
1-bromo-2-chloroethane	haloalkane; organobromine compound; organochlorine compound	mutagen	low
bromphenol blue	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; phenols; sultone	acid-base indicator; dye; two-colour indicator	low
bromcresol purple	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; polyphenol; sultone	acid-base indicator; dye; two-colour indicator	low
bromacil	organobromine compound; pyrimidone		low
bromochlorodifluoromethane	one-carbon compound; organobromine compound; organochlorine compound; organofluorine compound		low
perflubron	haloalkane; organobromine compound; perfluorinated compound	blood substitute; radioopaque medium	low
eosine yellowish-(ys)	organic sodium salt; organobromine compound	fluorochrome; histological dye	low
1-bromo-2,4-dinitrobenzene	C-nitro compound; organobromine compound		low
4-bromo-2-chlorophenol	halophenol; monochlorobenzenes; organobromine compound		low
6-bromo-2-naphthol	naphthols; organobromine compound		low
cincreasin	benzoxazole; organobromine compound		low
8-bromo cyclic adenosine monophosphate	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist	low
2,3,7,8-tetrabromodibenzo-4-dioxin	dibenzodioxine; organobromine compound		low
decamethrin	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide	low
bromfenac	aromatic amino acid; benzophenones; organobromine compound; substituted aniline	non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
1,2-dibromo-2,4-dicyanobutane	aliphatic nitrile; organobromine compound	allergen; sensitiser	low
5-bromo-4-chloro-3-indolyl beta-galactoside	beta-D-galactoside; D-aldohexose derivative; indolyl carbohydrate; organobromine compound; organochlorine compound	chromogenic compound	low
5-bromo-4-chloro-3-indoxyl phosphate	aryl phosphate; indoles; organobromine compound; organochlorine compound	chromogenic compound	low
bromosuccinimide	dicarboximide; organobromine compound; pyrrolidinone	reagent	low
bromopyruvate	2-oxo monocarboxylic acid; organobromine compound; oxo carboxylic acid	alkylating agent; antineoplastic agent	low
gr 117289	1-benzofurans; biaryl; imidazolyl carboxylic acid; monocarboxylic acid; organobromine compound; organochlorine compound; tetrazoles	angiotensin receptor antagonist; antihypertensive agent	low
6-bromo-2-naphthyl-beta-galactopyranoside	beta-D-galactoside; organobromine compound	chromogenic compound	low
2,2',4,4'-tetrabromodiphenyl ether	aromatic ether; organobromine compound		low
bromoacetaldehyde	organobromine compound		low
monobromobimane	organobromine compound; pyrazolopyrazole	fluorochrome	low
dibromobimane	organobromine compound; pyrazolopyrazole	fluorochrome	low
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene	monoterpenoid; organobromine compound; organochlorine compound	algal metabolite; antineoplastic agent; marine metabolite	low
2,2',4,4',5,5'-hexabrominated diphenyl ether	aromatic ether; organobromine compound		low
eosine-5-isothiocyanate	isothiocyanate; organobromine compound		low
4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile	monochlorobenzenes; nitrile; organobromine compound; organochlorine acaricide; organochlorine insecticide; organofluorine acaricide; organofluorine insecticide; pyrroles	acaricide; antifouling biocide; insecticide	low
etravirine	aminopyrimidine; aromatic ether; dinitrile; organobromine compound	antiviral agent; HIV-1 reverse transcriptase inhibitor	low
2-(4-bromophenyl)-5-(2-methylphenyl)-1,3,4-oxadiazole	organobromine compound		low
mitobronitol	alcohol; organobromine compound		low
2-amino-4-[(4-bromophenyl)methylthio]-3-azaspiro[5.5]undeca-1,4-diene-1,5-dicarbonitrile	organobromine compound		low
SMER 28	organobromine compound; quinazolines; secondary amino compound	autophagy inducer	low
2-(4-bromophenyl)-3,5-dimethyl-4-oxido-6-phenylpyrazin-1-ium 1-oxide	organobromine compound		low
2-(4-bromophenyl)thiazolidine	organobromine compound		low
wiskostatin	carbazoles; organobromine compound; secondary alcohol; tertiary amino compound		low
N-[1-(4-bromophenyl)ethyl]cyclobutanecarboxamide	organobromine compound		low
zd 6474	aromatic ether; organobromine compound; organofluorine compound; piperidines; quinazolines; secondary amine	antineoplastic agent; tyrosine kinase inhibitor	low
bromohydrin pyrophosphate	alkyl diphosphate; organobromine compound	phosphoantigen	low
mitolactol	alcohol; organobromine compound		low
metrafenone	aromatic ether; aryl phenyl ketone fungicide; benzophenones; organobromine compound	antifungal agrochemical	low
1-azakenpaullone	lactam; organic heterotetracyclic compound; organobromine compound; organonitrogen heterocyclic compound	EC 2.7.11.26 (tau-protein kinase) inhibitor; Wnt signalling activator	low
lonafarnib	benzocycloheptapyridine; heteroarylpiperidine; N-acylpiperidine; organobromine compound; organochlorine compound; ureas		low
5-bromouridine triphosphate	organobromine compound; pyrimidine ribonucleoside 5'-triphosphate		low
2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid	biphenyls; organobromine compound		low
ageladine a	alkaloid; aromatic amine; imidazopyridine; organobromine compound; pyrroles	angiogenesis inhibitor; antineoplastic agent; matrix metalloproteinase inhibitor; metabolite	low
jaspamide b	cyclodepsipeptide; organobromine compound	animal metabolite; antineoplastic agent; marine metabolite	low
massadine	alkaloid; guanidines; organobromine compound; pyrrolecarboxamide	animal metabolite; EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor; marine metabolite	low
chlorantranilipole	monochlorobenzenes; organobromine compound; pyrazole insecticide; pyrazoles; pyridines; secondary carboxamide	ryanodine receptor agonist	low
laurinterol	organobromine compound; phenols; sesquiterpenoid	antibacterial agent; apoptosis inducer; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; metabolite	low
ceratamine a	alkaloid; aromatic ether; cyclic ketone; organic heterobicyclic compound; organobromine compound; secondary amino compound; tertiary amine	antimitotic; metabolite	low
cyantraniliprole	nitrile; organobromine compound; organochlorine compound; pyrazole insecticide; pyridines; secondary carboxamide	ryanodine receptor agonist	low
2,2',4,5'-tetrabromodiphenyl ether	aromatic ether; organobromine compound		low
hexabromodiphenyl ether 154	aromatic ether; organobromine compound		low
bde 183	aromatic ether; organobromine compound		low
macitentan	aromatic ether; organobromine compound; pyrimidines; ring assembly; sulfamides	antihypertensive agent; endothelin receptor antagonist; orphan drug	low
bromophycolide a	diterpenoid; macrolide; organobromine compound; phenols; tertiary alcohol	anti-HIV agent; antibacterial agent; antifungal agent; antimalarial; antineoplastic agent; metabolite	low
ph 797804	aromatic ether; benzamides; organobromine compound; organofluorine compound; pyridone	anti-inflammatory agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
act-132577	aromatic ether; organobromine compound; pyrimidines; sulfamides	antihypertensive agent; drug metabolite; endothelin receptor antagonist; xenobiotic metabolite	low
dibromophakellin	alkaloid; guanidines; organobromine compound	alpha-adrenergic agonist; animal metabolite; marine metabolite	low
(E,E)-1-bromo-2,5-bis-(4-hydroxystyryl)benzene	organobromine compound; polyphenol	fluorescent dye	low
AZ3451	benzimidazoles; benzodioxoles; nitrile; organobromine compound; secondary carboxamide	anti-inflammatory agent; autophagy inducer; PAR2 negative allosteric modulator	low
8-bromocyclic gmp	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist	low
8-bromo-2'-deoxyguanosine	guanosines; organobromine compound		low
quinacrine	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor	low
vanilmandelic acid	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite	low
4-(2,4-dichlorophenoxy)butyric acid	aromatic ether; monocarboxylic acid; organochlorine compound	agrochemical; phenoxy herbicide; synthetic auxin	low
win 52035	aromatic ether		low
win 52084	aromatic ether		low
5-(nonyloxy)tryptamine	aromatic ether; primary amino compound; tryptamines	serotonergic agonist	low
methylbufotenin	aromatic ether; tertiary amino compound; tryptamine alkaloid	hallucinogen; plant metabolite	low
5-methoxytryptamine	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist	low
ro 48-8071	aromatic ether; aromatic ketone; bromobenzenes; monofluorobenzenes; olefinic compound; tertiary amino compound	antineoplastic agent; EC 5.4.99.7 (lanosterol synthase) inhibitor	low
rtki cpd	aromatic ether; monochlorobenzenes; quinazolines	antineoplastic agent; antiviral agent; epidermal growth factor receptor antagonist; geroprotector	low
amsacrine	acridines; aromatic ether; sulfonamide	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
aristolochic acid i	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin	low
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite	low
bufetolol	aromatic ether		low
bufexamac	aromatic ether; hydroxamic acid	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
bunitrolol	aromatic ether		low
bupranolol	aromatic ether		low
verapamil	aromatic ether; nitrile; polyether; tertiary amino compound		low
cgp 12177	aromatic ether; benzimidazoles; secondary alcohol; secondary amino compound	beta-adrenergic antagonist	low
ciglitazone	aromatic ether; thiazolidinone	antineoplastic agent; insulin-sensitizing drug	low
cirazoline	aromatic ether		low
clofibrate	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist	low
clofibric acid	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist	low
colchicine, (+-)-isomer	acetamides; alkaloid; aromatic ether; carbotricyclic compound	microtubule-destabilising agent; plant metabolite	low
croconazole	aromatic ether; conazole antifungal drug; imidazole antifungal drug; monochlorobenzenes		low
cypermethrin	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide	low
racemethorphan	aromatic ether; morphinane alkaloid; morphinane-like compound; organic heterotetracyclic compound		low
dibucaine	aromatic ether; monocarboxylic acid amide; tertiary amino compound	topical anaesthetic	low
dilacor xr	acetate ester; aromatic ether; benzothiazepine; lactam; tertiary amino compound		low
domiphen	aromatic ether		low
donepezil	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent	low
epirizole	aromatic ether		low
ethacrynic acid	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic	low
ethoxzolamide	aromatic ether; benzothiazoles; sulfonamide	antiglaucoma drug; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor	low
2-hexyloxybenzamide	aromatic ether; benzamides	antifungal agent	low
carbonyl cyanide p-trifluoromethoxyphenylhydrazone	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore	low
fenofibrate	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic	low
fenvalerate	aromatic ether; carboxylic ester; monochlorobenzenes	pyrethroid ester acaricide; pyrethroid ester insecticide	low
flecainide	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug	low
fluoxetine	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound		low
gallamine triethiodide	aromatic ether		low
gemfibrozil	aromatic ether	antilipemic drug	low
haloprogin	aromatic ether		low
indomethacin	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic	low
ipriflavone	aromatic ether; isoflavones	bone density conservation agent	low
ly 171883	acetophenones; aromatic ether; phenols; tetrazoles	anti-asthmatic drug; leukotriene antagonist	low
mephenesin	aromatic ether; glycerol ether		low
methocarbamol	aromatic ether; carbamate ester; secondary alcohol		low
methoctramine	aromatic ether; tetramine	muscarinic antagonist	low
methoxsalen	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite	low
metoprolol	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic	low
mexiletine	aromatic ether; primary amino compound	anti-arrhythmia drug	low
midodrine	amino acid amide; aromatic ether; secondary alcohol	alpha-adrenergic agonist; prodrug; sympathomimetic agent; vasoconstrictor agent	low
clorgyline	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor	low
nefazodone	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor	low
nimesulide	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug	low
nisoxetine	aromatic ether; secondary amino compound	adrenergic uptake inhibitor; antidepressant	low
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide	aromatic ether; C-nitro compound; sulfonamide	antineoplastic agent; cyclooxygenase 2 inhibitor	low
omeprazole	aromatic ether; benzimidazoles; pyridines; sulfoxide		low
oxprenolol	aromatic ether		low
pantoprazole	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic	low
pd 153035	aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist	low
pentamidine	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic	low
phenacetin	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug	low
pioglitazone	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic	low
piretanide	aromatic ether		low
pramoxine	aromatic ether; morpholines	local anaesthetic	low
prazosin	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor	low
primaquine	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial	low
proglumetacin	aromatic ether; benzamides; carboxylic ester; monochlorobenzenes; N-acylindole; N-alkylpiperazine	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; lipoxygenase inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug	low
propoxur	aromatic ether; carbamate ester	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor	low
pyrilamine	aromatic ether; ethylenediamine derivative	H1-receptor antagonist	low
sulfadimethoxine	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic	low
tetrahydropapaverine	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; polyether; secondary amino compound		low
tilorone	aromatic ether; diether; fluoren-9-ones; tertiary amino compound	anti-inflammatory agent; antineoplastic agent; antiviral agent; interferon inducer; nicotinic acetylcholine receptor agonist	low
ultram	aromatic ether; tertiary alcohol; tertiary amino compound		low
triclosan	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic	low
viloxazine	aromatic ether		low
wb 4101	aromatic ether; benzodioxine; secondary amino compound	alpha-adrenergic antagonist	low
3,3',5-triiodothyropropionic acid	aromatic ether		low
methacetin	acetamides; aromatic ether		low
mestranol	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen	low
visnagin	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent	low
2-tert-butyl-4-hydroxyanisole	aromatic ether; phenols		low
mecoprop	aromatic ether; monocarboxylic acid; monochlorobenzenes		low
phenetidine	aromatic ether; substituted aniline		low
2-methyl-4-chlorophenoxy gamma-butyric acid	aromatic ether; monocarboxylic acid; monochlorobenzenes	environmental contaminant; phenoxy herbicide; xenobiotic	low
di-(4-aminophenyl)ether	aromatic ether		low
phenyl ether	aromatic ether	plant metabolite	low
diglycidyl resorcinol ether	aromatic ether		low
phenetole	aromatic ether		low
scoparone	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite	low
dimethoxyphenylethylamine	alkaloid; aromatic ether; phenylethylamine	allergen; plant metabolite	low
dichlorprop	aromatic ether; dichlorobenzene; monocarboxylic acid		low
3-tert-butyl-4-hydroxyanisole	aromatic ether; phenols	antioxidant; human xenobiotic metabolite	low
ethyl vanillin	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent	low
benzethonium chloride	aromatic ether; chloride salt; quaternary ammonium salt	antibacterial agent; antifungal agent; antiseptic drug; antiviral agent; disinfectant	low
peucedanin	aromatic ether; furanocoumarin; lactone	plant metabolite	low
phenetidine	aromatic ether; primary amino compound; substituted aniline	drug metabolite	low
6-methoxybenzoxazolinone	aromatic ether; benzoxazole	antibacterial agent; anticonvulsant; antifungal agent; muscle relaxant; plant metabolite	low
3-anisidine	aromatic ether; substituted aniline		low
domiphen bromide	aromatic ether		low
dibrompropamidine	aromatic ether		low
4-Ethoxyphenol	aromatic ether; phenols		low
bulbocapnine	aporphine alkaloid; aromatic ether; oxacycle; phenols	EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor; EC 1.4.3.22 (diamine oxidase) inhibitor; plant metabolite	low
benzydamine	aromatic ether; indazoles; tertiary amino compound	analgesic; central nervous system stimulant; hallucinogen; local anaesthetic; non-steroidal anti-inflammatory drug	low
xylocholine	aromatic ether		low
3-methoxycatechol	aromatic ether; catechols	G-protein-coupled receptor agonist	low
2-phenoxypropanoic acid	aromatic ether; carboxylic acid		low
metaxalone	aromatic ether		low
heliamine	aromatic ether; diether; isoquinoline alkaloid; isoquinolines	plant metabolite	low
2,4,6-trichlorophenyl 4-nitrophenyl ether	aromatic ether; C-nitro compound; chlorobenzenes	EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
etridiazol	aromatic ether; organochlorine compound; thiadiazole antifungal agent; thiadiazoles	antifungal agrochemical; nitrification inhibitor	low
toliprolol	aromatic ether		low
5-methoxyindoleacetic acid	aromatic ether; indole-3-acetic acids	antibacterial agent; Brassica napus metabolite; carcinogenic agent; human urinary metabolite; marine xenobiotic metabolite; rat metabolite	low
iproclozide	aromatic ether		low
phenoxyacetic acid	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant	low
nafenopin	aromatic ether; monocarboxylic acid		low
methyl vanillate	aromatic ether; benzoate ester; phenols	antioxidant; plant metabolite	low
5-methoxyindole-2-carboxylic acid	aromatic ether; indolecarboxylic acid	EC 1.8.1.4 (dihydrolipoyl dehydrogenase) inhibitor; hypoglycemic agent; plant metabolite	low
2-isopropoxyphenol	aromatic ether; phenols		low
dehydroemetine	aromatic ether; isoquinolines; pyridoisoquinoline	antileishmanial agent; antimalarial; antiprotozoal drug	low
1,2-epoxy-3-(p-nitrophenoxy)propane	aromatic ether; C-nitro compound; epoxide		low
laurolitsine	aporphine alkaloid; aromatic ether; phenols	HIV-1 integrase inhibitor; metabolite	low
metocurine iodide	aromatic ether		low
ac 45594	aromatic ether		low
3-phenoxybenzylalcohol	aromatic ether; benzyl alcohols	marine xenobiotic metabolite	low
fluorodifen	aromatic ether		low
acridine half-mustard	aminoacridines; aromatic ether; organochlorine compound; secondary amino compound	mutagen	low
precocene i	aromatic ether; chromenes	plant metabolite; precocenes	low
oxadiazon	aromatic ether		low
lofexidine	aromatic ether; carboxamidine; dichlorobenzene; imidazoles	alpha-adrenergic agonist; antihypertensive agent	low
alclofenac	aromatic ether; monocarboxylic acid; monochlorobenzenes	drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
phenylglycidyl ether	aromatic ether		low
phenoxyethanol	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant	low
metipranolol	acetate ester; aromatic ether; propanolamine; secondary amino compound	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist	low
silybin	aromatic ether; benzodioxine; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; hepatoprotective agent; plant metabolite	low
oxamethacin	aromatic ether; hydroxamic acid; N-acylindole; organochlorine compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
canadine	aromatic ether; berberine alkaloid; organic heteropentacyclic compound; oxacycle		low
7-ethoxycoumarin	aromatic ether; coumarins		low
medifoxamine	aromatic ether		low
chlormethoxynil	aromatic ether		low
climbazole	aromatic ether; hemiaminal ether; imidazoles; ketone; monochlorobenzenes		low
4-hexyloxyaniline	aromatic ether; substituted aniline		low
ticrynafen	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid; thiophenes	antihypertensive agent; hepatotoxic agent; loop diuretic	low
2-(4-(2,4-dichlorophenoxy)phenoxy)propionic acid	aromatic ether; dichlorobenzene; diether; monocarboxylic acid		low
bezafibrate	aromatic ether; monocarboxylic acid amide; monocarboxylic acid; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic	low
oxyfluorofen	aromatic ether	EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
triadimefon	aromatic ether; hemiaminal ether; ketone; monochlorobenzenes; triazoles		low
levobunolol	aromatic ether; cyclic ketone; propanolamine	antiglaucoma drug; beta-adrenergic antagonist	low
dichlorfop-methyl	aromatic ether; dichlorobenzene; diether; methyl ester		low
triadimenol	aromatic ether; conazole fungicide; hemiaminal ether; monochlorobenzenes; secondary alcohol; triazole fungicide	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; xenobiotic metabolite	low
triclopyr	aromatic ether; chloropyridine; monocarboxylic acid	agrochemical; environmental contaminant; herbicide; xenobiotic	low
prenalterol	aromatic ether		low
st 1059	aromatic ether; primary amino compound; secondary alcohol	alpha-adrenergic agonist; sympathomimetic agent; vasoconstrictor agent	low
paroxetine	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor	low
acifluorfen	aromatic ether; benzoic acids; C-nitro compound; monocarboxylic acid; organochlorine compound; organofluorine compound	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
bopindolol	aromatic ether; benzoate ester; methylindole; secondary amino compound		low
fenpropathrin, (+-)-isomer	aromatic ether; cyclopropanecarboxylate ester	agrochemical; pyrethroid ester acaricide; pyrethroid ester insecticide	low
triflumuron	aromatic ether; benzoylurea insecticide; monochlorobenzenes; organofluorine compound		low
flutolanil	(trifluoromethyl)benzenes; aromatic ether; benzamides; benzanilide fungicide	antifungal agrochemical; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor	low
fenoxaprop ethyl	aromatic ether		low
triclabendazole	aromatic ether		low
4,5-amino-3,5-dichloro-6-fluoro-2-pyridinyloxyacetic acid	aminopyridine; aromatic ether; monocarboxylic acid; organochlorine compound; organofluorine compound	environmental contaminant; herbicide; xenobiotic	low
fluvalinate	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; nitrile; organochlorine acaricide; organochlorine insecticide; organofluorine acaricide; organofluorine insecticide	agrochemical; pyrethroid ester acaricide; pyrethroid ester insecticide	low
haloxyfop	aromatic ether; monocarboxylic acid; organochlorine compound; organofluorine compound; pyridines		low
fluazifop-butyl	aromatic ether; carboxylic ester; organofluorine compound; pyridines		low
fomesafen	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
fenoxycarb	aromatic ether; carbamate ester	environmental contaminant; insecticide; juvenile hormone mimic; xenobiotic	low
quizalofop-ethyl	aromatic ether; ethyl ester; organochlorine compound; quinoxaline derivative		low
cetamolol	aromatic ether		low
atomoxetine	aromatic ether; secondary amino compound; toluenes	adrenergic uptake inhibitor; antidepressant; environmental contaminant; xenobiotic	low
methyl bensulfuron	aromatic ether; methyl ester; N-sulfonylurea; pyrimidines	agrochemical; EC 2.2.1.6 (acetolactate synthase) inhibitor; herbicide	low
itraconazole	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor	low
loxtidine	aromatic ether; piperidines; primary alcohol; triazoles	H2-receptor antagonist	low
disoxaril	aromatic ether		low
chlorimuron ethyl	aromatic ether; ethyl ester; N-sulfonylurea; organochlorine pesticide; pyrimidines; sulfamoylbenzoate	agrochemical; EC 2.2.1.6 (acetolactate synthase) inhibitor; proherbicide	low
tepoxalin	aromatic ether; hydroxamic acid; monochlorobenzenes; pyrazoles	antipyretic; apoptosis inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; immunomodulator; lipoxygenase inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
esmolol	aromatic ether; ethanolamines; methyl ester; secondary alcohol; secondary amino compound		low
pioglitazone hydrochloride	aromatic ether		low
aripiprazole	aromatic ether; delta-lactam; dichlorobenzene; N-alkylpiperazine; N-arylpiperazine; quinolone	drug metabolite; H1-receptor antagonist; second generation antipsychotic; serotonergic agonist	low
sulfametrole	aromatic ether; substituted aniline; sulfonamide antibiotic; thiadiazoles		low
propamidine	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug	low
hexamidine	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug	low
o-4-methylthymine	aromatic ether; methylthymine	human metabolite	low
fenclofenac	aromatic ether		low
tetraiodothyroacetic acid	2-halophenol; aromatic ether; iodophenol; monocarboxylic acid	apoptosis inducer; human metabolite; thyroid hormone	low
fluazuron	aromatic ether; chloropyridine; monochlorobenzenes; N-acylurea; organochlorine acaricide; organofluorine acaricide; phenylureas	acaricide; mite growth regulator	low
etiroxate	aromatic ether		low
etofamide	aromatic ether		low
d 888	aromatic ether; nitrile; tertiary amino compound	anti-arrhythmia drug; calcium channel blocker; vasodilator agent	low
esreboxetine	aromatic ether		low
guaethol	aromatic ether; phenols; volatile organic compound	flavouring agent	low
spiramide	aromatic ether; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	dopaminergic antagonist; serotonergic antagonist	low
5'-nitro-2'-propoxyacetanilide	aromatic ether; C-nitro compound		low
suberosin	aromatic ether; coumarins	anticoagulant; plant metabolite	low
4-methoxyestradiol	17beta-hydroxy steroid; 3-hydroxy steroid; aromatic ether; phenols	estrogen; human metabolite; rat metabolite	low
toltrazuril	aromatic ether		low
plafibride	aromatic ether		low
cinitapride	aromatic ether; C-nitro compound		low
isoscopoletin	aromatic ether; hydroxycoumarin	plant metabolite	low
ethofenprox	aromatic ether	pyrethroid ether insecticide	low
uk 68798	aromatic ether; sulfonamide; tertiary amino compound	anti-arrhythmia drug; potassium channel blocker	low
hp 873	1,2-benzoxazoles; aromatic ether; aromatic ketone; methyl ketone; monoamine; organofluorine compound; piperidines; tertiary amino compound	dopaminergic antagonist; second generation antipsychotic; serotonergic antagonist	low
fenoxypropazine	aromatic ether		low
fluphenacur	aromatic ether; benzoylurea insecticide; dichlorobenzene; N-acylurea; organofluorine compound		low
amezinium	aromatic ether; primary arylamine; pyridazinium ion	adrenergic uptake inhibitor; antihypotensive agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; sympathomimetic agent	low
rubrofusarin	aromatic ether; benzochromenone; phenols; polyketide	biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; fungal metabolite	low
triasulfuron	1,3,5-triazines; aromatic ether; N-sulfonylurea; organochlorine compound	agrochemical; herbicide	low
dauricine	aromatic ether; bisbenzylisoquinoline alkaloid; isoquinolines; phenols; tertiary amino compound	plant metabolite	low
uvaretin	aromatic ether; dihydrochalcones; polyketide; resorcinol	antineoplastic agent; plant metabolite	low
fangchinoline	aromatic ether; bisbenzylisoquinoline alkaloid; macrocycle	anti-HIV-1 agent; anti-inflammatory agent; antineoplastic agent; antioxidant; neuroprotective agent; plant metabolite	low
prochloraz	amide fungicide; aromatic ether; conazole fungicide; imidazole fungicide; imidazoles; trichlorobenzene; ureas	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic	low
stictic acid	aromatic ether		low
pramoxine hydrochloride	aromatic ether		low
4-methoxybenzylamine	aralkylamino compound; aromatic ether; primary amino compound		low
xanthurenic acid 8-methyl ether	aromatic ether; monohydroxyquinoline; quinolinemonocarboxylic acid	carcinogenic agent; metabolite; mouse metabolite	low
adriamycinol	aminoglycoside; anthracycline antibiotic; aromatic ether; deoxy hexoside; p-quinones; phenols; polyol; tetracenequinones	cardiotoxic agent; drug metabolite	low
difenoconazole	aromatic ether; conazole fungicide; cyclic ketal; dioxolane; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic	low
a 8947	aromatic ether; biaryl; N-sulfonylurea; pyrazole pesticide; tetrazoles	EC 2.2.1.6 (acetolactate synthase) inhibitor; herbicide	low
thifluzamide	1,3-thiazoles; anilide fungicide; aromatic amide; aromatic ether; dibromobenzene; organofluorine compound	antifungal agrochemical; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor	low
ethylhydrocupreine	aromatic ether; cinchona alkaloid	EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor	low
7,8-dihydromethysticin	2-pyranones; aromatic ether		low
4,5-dimethoxy-2-nitrobenzaldehyde	aromatic ether; C-nitro compound		low
bisphenol f diglycidyl ether	aromatic ether; diarylmethane; epoxide		low
oryzemate	1,2-benzisothiazole; aromatic ether; benzothiazole fungicide; sulfone	antifungal agrochemical; plant activator	low
bitertanol	aromatic ether; biphenyls; secondary alcohol; triazoles		low
fluazifop	aromatic ether; monocarboxylic acid; organofluorine compound; pyridines		low
diflufenican	(trifluoromethyl)benzenes; aromatic ether; pyridinecarboxamide	carotenoid biosynthesis inhibitor; environmental contaminant; herbicide; xenobiotic	low
hexafluoron	aromatic ether; benzoylurea insecticide; dichlorobenzene; N-acylurea; organochlorine insecticide; organofluorine insecticide		low
diethofencarb	aromatic ether; carbamate ester; carbanilate fungicide	antifungal agrochemical	low
pyriproxyfen	aromatic ether; pyridines	juvenile hormone mimic	low
methyl 2-(((((4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoate	aromatic ether; benzoate ester; diamino-1,3,5-triazine; methyl ester; N-sulfonylurea	EC 2.2.1.6 (acetolactate synthase) inhibitor; herbicide	low
dpx e9636	aromatic ether; N-sulfonylurea; pyridines; pyrimidines; sulfone	environmental contaminant; herbicide; xenobiotic	low
aclonifen	aromatic ether; C-nitro compound; monochlorobenzenes; primary amino compound; substituted aniline	agrochemical; carotenoid biosynthesis inhibitor; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
cinosulfuron	aromatic ether		low
clodinafop-propargyl	aromatic ether; carboxylic ester; organochlorine compound; organofluorine compound; propyzamide; pyridines	agrochemical; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; herbicide	low
triflusulfuron-methyl	1,3,5-triazines; aromatic ether; benzoate ester; methyl ester; N-sulfonylurea; organofluorine compound; tertiary amino compound	agrochemical; EC 2.2.1.6 (acetolactate synthase) inhibitor; proherbicide	low
vestitol	aromatic ether; hydroxyisoflavans; methoxyisoflavan	anti-inflammatory agent; phytoalexin; plant metabolite	low
laudanine	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; phenols; racemate		low
cryptopleurine	alkaloid antibiotic; alkaloid; aromatic ether; organic heteropentacyclic compound	antineoplastic agent; antiviral agent; protein synthesis inhibitor	low
6-hydroxymethylmexiletine	aromatic ether		low
4-hydroxymexiletine	aromatic ether; phenols		low
novaluron	aromatic ether; benzoylurea insecticide; monochlorobenzenes; organofluorine compound		low
bursehernin	aromatic ether; benzodioxoles; butan-4-olide; lignan	plant metabolite	low
allocryptopine	aromatic ether; cyclic acetal; cyclic ketone; dibenzazecine alkaloid; organic heterotetracyclic compound; tertiary amino compound		low
sporidesmin	aromatic ether; cyclic ketone; diketone; organic disulfide; organic heteropentacyclic compound; organochlorine compound; secondary alcohol; tertiary alcohol; tertiary amino compound	mycotoxin; Wnt signalling activator	low
syringaresinol	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite	low
p-methoxy-n-methylphenethylamine	aromatic ether; secondary amino compound	metabolite	low
aflatoxin q1	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human xenobiotic metabolite	low
u 73122	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor	low
cyfluthrin	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound; organofluorine compound	agrochemical; pyrethroid ester insecticide	low
norverapamil	aromatic ether; nitrile; polyether; secondary amino compound		low
fumitremorgin a	aromatic ether; diol; indole alkaloid; organic heterohexacyclic compound; organic peroxide	mycotoxin	low
deguelin	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite	low
aristolochic acid ii	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin	low
tephrosin	aromatic ether; cyclic ketone; organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; pesticide	low
alpha-hydroxymetoprolol	aromatic ether		low
5-(tetradecyloxy)-2-furancarboxylic acid	aromatic ether; furoic acid	antineoplastic agent; apoptosis inducer; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; PPARalpha agonist	low
tafenoquine	(trifluoromethyl)benzenes; aminoquinoline; aromatic ether; primary amino compound; secondary amino compound		low
5-hydroxymethylomeprazole	aromatic ether; benzimidazoles; pyridines; sulfoxide	drug metabolite	low
mosapride	aromatic ether; benzamides; monochlorobenzenes; monofluorobenzenes; morpholines; secondary carboxamide; substituted aniline; tertiary amino compound		low
ym 12617	aromatic ether; secondary amino compound; sulfonamide		low
gefitinib	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist	low
cgp 28392	aromatic ether		low
sodium-binding benzofuran isophthalate	1-benzofurans; aromatic ether; crown compound; tetracarboxylic acid	fluorochrome	low
garenoxacin	aromatic ether; cyclopropanes; isoindoles; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic	antibacterial drug; non-steroidal anti-inflammatory drug	low
ay 25545	acetate ester; aromatic ether; C-glycosyl compound; naphthoisochromene; olefinic compound; phenols; tertiary amine	antimicrobial agent; antineoplastic agent; bacterial metabolite	low
reboxetine	aromatic ether		low
b 823-08	aromatic ether		low
cyclazosin	aromatic amide; aromatic ether; furans; monocarboxylic acid amide; quinazolines; quinoxaline derivative	adenosine A2A receptor antagonist	low
ivabradine	aromatic ether; benzazepine; carbobicyclic compound; tertiary amino compound	cardiotonic drug	low
febuxostat	1,3-thiazolemonocarboxylic acid; aromatic ether; nitrile	EC 1.17.3.2 (xanthine oxidase) inhibitor	low
marsupsin	1-benzofurans; aromatic ether; polyphenol	antilipemic drug; hypoglycemic agent; metabolite	low
6,6'-bieckol	aromatic ether; oxacycle; phlorotannin	anti-HIV-1 agent; metabolite; radical scavenger	low
xibenolol	aromatic ether		low
cicloprolol	aromatic ether		low
chs 828	aromatic ether		low
2-(4-methoxyphenoxy)propanoic acid	aromatic ether; carboxylic acid		low
moxifloxacin	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug	low
rp 73401	aromatic ether; benzamides; chloropyridine; monocarboxylic acid amide	anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; phosphodiesterase IV inhibitor	low
varespladib	aromatic ether; benzenes; dicarboxylic acid monoamide; indoles; monocarboxylic acid; primary carboxamide	anti-inflammatory drug; antidote; EC 3.1.1.4 (phospholipase A2) inhibitor	low
schizandrin b	aromatic ether; cyclic acetal; organic heterotetracyclic compound; oxacycle; tannin	anti-asthmatic agent; anti-inflammatory agent; antilipemic drug; antioxidant; apoptosis inhibitor; hepatoprotective agent; nephroprotective agent; neuroprotective agent; plant metabolite	low
s 23121	aromatic ether; dicarboximide; monochlorobenzenes; monofluorobenzenes; pyrroline; terminal acetylenic compound		low
acrovestone	acetophenones; aromatic ether; olefinic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite	low
corytuberine	aporphine alkaloid; aromatic ether; organic heterotetracyclic compound; polyphenol; tertiary amino compound	plant metabolite	low
actinodaphine	aporphine alkaloid; aromatic ether; organic heteropentacyclic compound; phenols; secondary amino compound	antibacterial agent; antifungal agent; antineoplastic agent; apoptosis inducer; plant metabolite; platelet aggregation inhibitor; topoisomerase inhibitor	low
isohomovanillic acid	aromatic ether; phenols; phenylacetic acids	metabolite	low
3,5-diiodothyropropionic acid	aromatic ether; monocarboxylic acid; organoiodine compound; phenols		low
7,8-dihydro-5,6-dehydrokawain	2-pyranones; aromatic ether		low
4-amino-2-methoxypyrimidine	aminopyrimidine; aromatic ether; methylcytosine	metabolite	low
aristolochic acid D	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; nephrotoxin; toxin	low
myricanone	aromatic ether; cyclic ketone; diarylheptanoid; methoxybenzenes; phenols	antineoplastic agent; plant metabolite	low
pannarin	aldehyde; aromatic ether; depsidones; organic heterotricyclic compound; organochlorine compound; phenols	antimicrobial agent; antineoplastic agent; apoptosis inducer; lichen metabolite	low
aminopotentidine	aromatic ether; benzamides; guanidines; nitrile; piperidines; substituted aniline	H2-receptor antagonist	low
aristolochic acid c	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin	low
pluviatolide	aromatic ether; benzodioxoles; butan-4-olide; lignan; phenols	plant metabolite	low
erysodine	aromatic ether; diether; Erythrina alkaloid; organic heterotetracyclic compound; phenols	antiparasitic agent; nicotinic antagonist; phytogenic insecticide	low
erlotinib	aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound	antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor	low
rubrofusarin B	aromatic ether; benzochromenone; naphtho-gamma-pyrone; phenols; polyketide	Aspergillus metabolite	low
ly 293111	aromatic ether		low
enrasentan	aromatic ether; benzodioxoles; indanes; monocarboxylic acid; monomethoxybenzene; primary alcohol	antihypertensive agent; endothelin receptor antagonist	low
quizalofop	aromatic ether; monocarboxylic acid; organochlorine compound; quinoxaline derivative		low
cyhalofop-butyl	aromatic ether		low
cyperin	aromatic ether		low
aflatoxin b1	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite	low
5-o-methyllicoricidin	aromatic ether; hydroxyisoflavans; methoxyisoflavan	antibacterial agent; plant metabolite	low
pronuciferine	aromatic ether; cyclic ketone; isoquinoline alkaloid; isoquinolines; organic heterotetracyclic compound	plant metabolite	low
dronedarone	1-benzofurans; aromatic ether; aromatic ketone; sulfonamide; tertiary amino compound	anti-arrhythmia drug; environmental contaminant; xenobiotic	low
famoxadone	aromatic ether; carbohydrazide; oxazolidinone		low
cimicoxib	aromatic ether; imidazoles; organochlorine compound; organofluorine compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug	low
sorafenib	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor	low
dabuzalgron	aromatic ether; imidazoles; monochlorobenzenes; sulfonamide	alpha-adrenergic agonist	low
fonsecin	aromatic ether; cyclic hemiketal; heptaketide; naphtho-gamma-pyrone; phenols	Aspergillus metabolite; marine metabolite	low
lasofoxifene	aromatic ether; N-alkylpyrrolidine; naphthols; tetralins	antineoplastic agent; bone density conservation agent; cardioprotective agent; estrogen receptor agonist; estrogen receptor antagonist	low
(+-)-Dihydromethysticin	2-pyranones; aromatic ether		low
2-[2-[2-(2-aminophenoxy)ethoxy]ethoxy]aniline	aromatic ether; substituted aniline		low
chondocurine (1beta)-(+-)-isomer	aromatic ether		low
1-methyl-4-prop-2-enoxy-2-pyrimidinone	aromatic ether; pyrimidone		low
noscapine	aromatic ether; benzylisoquinoline alkaloid; cyclic acetal; isobenzofuranone; organic heterobicyclic compound; organic heterotricyclic compound; tertiary amino compound	antineoplastic agent; antitussive; apoptosis inducer; plant metabolite	low
4-[4-(3-methyl-4-nitrophenoxy)butoxy]benzonitrile	aromatic ether; C-nitro compound		low
lariciresinol	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite	low
tryptoquivaline	aromatic ether; indole alkaloid; organic heteropentacyclic compound	breast cancer resistance protein inhibitor; mycotoxin	low
2-methoxyestrone	17-oxo steroid; 3-hydroxy steroid; alicyclic ketone; aromatic ether; phenolic steroid; phenols	human metabolite; mouse metabolite	low
win 54954	aromatic ether		low
silychristin	1-benzofurans; aromatic ether; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	lipoxygenase inhibitor; metabolite; prostaglandin antagonist; radical scavenger	low
cleomiscosin a	aromatic ether; delta-lactone; organic heterotricyclic compound; phenols; primary alcohol	anti-inflammatory agent; metabolite	low
bispyribac	aromatic ether; benzoic acids; monocarboxylic acid; pyrimidines	herbicide	low
petunidin-3-glucoside	anthocyanin cation; aromatic ether; beta-D-glucoside	antioxidant; metabolite	low
malvidin-3-glucoside	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite	low
dioncophylline c	aromatic ether; biaryl; isoquinoline alkaloid; isoquinolines; methoxynaphthalene; methylnaphthalenes; naphthols	antimalarial; antiplasmodial drug; metabolite	low
stigmatellin	aromatic ether; chromones; olefinic compound; phenols	bacterial metabolite; quinol oxidation site inhibitor	low
roflumilast	aromatic ether; benzamides; chloropyridine; cyclopropanes; organofluorine compound	anti-asthmatic drug; phosphodiesterase IV inhibitor	low
teniposide	aromatic ether; beta-D-glucoside; cyclic acetal; furonaphthodioxole; gamma-lactone; monosaccharide derivative; phenols; thiophenes	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
prinomastat	aromatic ether; hydroxamic acid; pyridines; sulfonamide; thiomorpholines	antineoplastic agent; EC 3.4.24.35 (gelatinase B) inhibitor; matrix metalloproteinase inhibitor	low
posaconazole	aromatic ether; conazole antifungal drug; N-arylpiperazine; organofluorine compound; oxolanes; triazole antifungal drug; triazoles	trypanocidal drug	low
gancaonin I	1-benzofurans; aromatic ether; resorcinols	antibacterial agent; plant metabolite	low
glycyrin	aromatic ether; coumarins; hydroxyisoflavans	antibacterial agent; metabolite; plant metabolite	low
glyasperin D	aromatic ether; hydroxyisoflavans; methoxyisoflavan	plant metabolite	low
licoricidin	aromatic ether; hydroxyisoflavans; methoxyisoflavan	antibacterial agent; plant metabolite	low
egonol	1-benzofurans; aromatic ether; benzodioxoles; primary alcohol	plant metabolite	low
N-ethylharmine	aromatic ether; beta-carbolines; semisynthetic derivative	anti-HIV agent	low
pf 1163a	aromatic ether; lactam; macrolide antibiotic; secondary alcohol	antifungal agent; Penicillium metabolite	low
pf 1163b	aromatic ether; lactam; macrolide antibiotic	antifungal agent; Penicillium metabolite	low
licocoumarone	1-benzofurans; aromatic ether; resorcinols	antibacterial agent; apoptosis inducer; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite	low
4-(4-chloro-2-methylphenoxy)-n-hydroxybutanamide	aromatic ether		low
LSM-22807	aromatic ether		low
N-[2-(3-methylphenoxy)ethyl]-1H-1,2,4-triazole-5-carboxamide	aromatic ether		low
piperlactam s	alkaloid; aromatic ether; gamma-lactam; organic heterotetracyclic compound; phenols	anti-inflammatory agent; antioxidant; plant metabolite	low
5,5-dioxo-1-(4-phenoxyphenyl)-3a,4,6,6a-tetrahydro-3H-thieno[3,4-b]pyrrol-2-one	aromatic ether		low
antofine	alkaloid antibiotic; alkaloid; aromatic ether; organic heteropentacyclic compound	angiogenesis inhibitor; anti-inflammatory agent; antimicrobial agent; antineoplastic agent; antiviral agent; phytotoxin; plant metabolite	low
xanthohumol	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite	low
2-phenoxy-N-(2-pyridinyl)butanamide	aromatic ether		low
6-amino-4-(2-ethoxyphenyl)-3-propyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile	aromatic ether; pyranopyrazole		low
N-[4-[4-[[1-oxo-2-(1-pyrrolidinyl)ethyl]amino]phenoxy]phenyl]-2-(1-pyrrolidinyl)acetamide	aromatic ether		low
2-(3,4-diethoxyphenyl)-5-(2-furanyl)-1,3,4-oxadiazole	aromatic ether		low
2-[[5-(phenoxymethyl)-4-(2-phenylethyl)-1,2,4-triazol-3-yl]thio]acetamide	aromatic ether		low
1-(8-methyl-2,5,11,14-tetraoxa-8-azabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)ethanol	aromatic ether		low
3-[2-(3-phenoxypropyl)-5-tetrazolyl]pyridine	aromatic ether		low
1-cyclohexyl-5-(2-phenoxyethylthio)tetrazole	aromatic ether		low
N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-[[5-[(3-methylphenoxy)methyl]-1,3,4-oxadiazol-2-yl]thio]acetamide	aromatic ether		low
6-amino-4-[3-ethoxy-4-[2-(4-morpholinyl)ethoxy]phenyl]-3-ethyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile	aromatic ether; pyranopyrazole		low
2-[[5-[(2,3-dimethylphenoxy)methyl]-4-methyl-1,2,4-triazol-3-yl]thio]-1-thiophen-2-ylethanone	aromatic ether		low
(1-methyl-2-imidazolyl)-(4-phenylmethoxyphenyl)methanol	aromatic ether		low
5-(3-butoxyphenyl)-1,3,4-thiadiazol-2-amine	aromatic ether		low
3-(2-ethoxy-6-methyl-3-pyridinyl)-5-(2-pyridinyl)-1,2,4-oxadiazole	aromatic ether		low
6-(3,4,5-triethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole	aromatic ether; triazolothiadiazole		low
4-(1-benzotriazolyl)-5-(2-methoxyphenoxy)benzene-1,2-dicarbonitrile	aromatic ether		low
4-cyclohexyl-3-[(3-methylphenoxy)methyl]-1H-1,2,4-triazole-5-thione	aromatic ether		low
7-ethoxy-9-nitro-5H-benzo[b][1,4]benzoxazepin-6-one	aromatic ether		low
4-[4-(2-quinoxalinyl)phenoxy]benzene-1,2-dicarbonitrile	aromatic ether		low
1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(phenoxymethyl)-4-triazolecarboxylic acid ethyl ester	aromatic ether		low
2-(4-ethylphenoxy)-N-(1H-1,2,4-triazol-5-yl)acetamide	aromatic ether		low
2-(4-chloro-3-methylphenoxy)-N-(1H-1,2,4-triazol-5-yl)acetamide	aromatic ether		low
5-[(4-ethylphenoxy)methyl]-N-(2-pyridinylmethyl)-2-furancarboxamide	aromatic ether		low
7-methoxy-3,5-dimethyl-2-thiazolo[4,5-d]pyrimidinethione	aromatic ether		low
N-[4-(4-ethylphenyl)-2-thiazolyl]carbamic acid phenyl ester	aromatic ether		low
2-(2-bromo-4-methylphenoxy)-N-(2-pyridinylmethyl)acetamide	aromatic ether		low
1-[[3-(4-chlorophenoxy)phenyl]methyl]-4-ethylpiperazine	aromatic ether		low
2-methoxy-4-[(4-methyl-1,4-diazepan-1-yl)methyl]-6-nitrophenol	aromatic ether; C-nitro compound		low
4-[[4-(ethylamino)-6-(methylthio)-1,3,5-triazin-2-yl]oxy]benzoic acid ethyl ester	aromatic ether		low
5-ethyl-3-[[4-(2-methylpropoxy)phenyl]methylthio]-1H-1,2,4-triazole	aromatic ether		low
[4-[(2-fluorophenyl)methoxy]phenyl]-(1-pyrrolidinyl)methanethione	aromatic ether		low
5-[(2-chlorophenoxy)methyl]-3-pyridin-4-yl-1,2,4-oxadiazole	aromatic ether		low
4-(4-phenylmethoxyphenyl)thiadiazole	aromatic ether		low
N-methyl-2-[[4-methyl-5-[(4-nitrophenoxy)methyl]-1,2,4-triazol-3-yl]thio]acetamide	aromatic ether; C-nitro compound		low
2-[[5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl]thio]-1-(4-morpholinyl)ethanone	aromatic ether		low
4-(3-pyridinyloxy)benzene-1,2-dicarbonitrile	aromatic ether		low
N-tert-butyl-2-(4-chloro-3-methylphenoxy)acetamide	aromatic ether		low
1-(2-furanylmethyl)-3-(4-phenoxyphenyl)thiourea	aromatic ether		low
1-(2-methylpropyl)-3-(4-phenoxyphenyl)thiourea	aromatic ether		low
1-cyclopentyl-3-(4-phenoxyphenyl)thiourea	aromatic ether		low
5-[(4-ethoxyphenoxy)methyl]-N-(3-pyridinyl)-2-furancarboxamide	aromatic ether		low
2-(2,3-dimethylphenoxy)-N-pyridin-4-ylacetamide	aromatic ether		low
5-[(2-chlorophenoxy)methyl]-N-(2-thiazolyl)-2-furancarboxamide	aromatic ether		low
N-[5-[(4-chlorophenoxy)methyl]-1,3,4-thiadiazol-2-yl]-2-furancarboxamide	aromatic ether		low
N-(4,5-dihydrothiazol-2-yl)-2-(2-methylphenoxy)acetamide	aromatic ether		low
5-(2-fluorophenoxy)-1-methyl-3-nitro-1,2,4-triazole	aromatic ether		low
1-methyl-5-(1-naphthalenyloxy)-4-nitroimidazole	aromatic ether		low
curcumin	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger	low
1-(3,4-dimethoxyphenyl)-3-(2-methoxy-5-nitrophenyl)urea	aromatic ether; C-nitro compound		low
1-cyclopentyl-3-(2-phenoxyphenyl)thiourea	aromatic ether		low
N-(1-ethyl-2-benzimidazolyl)-5-[(4-methyl-2-nitrophenoxy)methyl]-2-furancarboxamide	aromatic ether; C-nitro compound		low
2-chloro-12-(4-methoxyphenyl)sulfonylquinoxalino[2,3-b][1,4]benzoxazine	aromatic ether		low
1-(3-methoxy-5-nitrophenyl)-3-(4-methylphenyl)urea	aromatic ether; C-nitro compound		low
2-(2-bromo-4-chlorophenoxy)-N-cyclohexyl-N-methylacetamide	aromatic ether		low
2-furanyl-[4-(4-phenoxyphenyl)sulfonyl-1-piperazinyl]methanone	aromatic ether		low
4-(2-methoxyphenoxy)-N-(3-pyridinyl)benzenesulfonamide	aromatic ether		low
1-(3-chlorophenyl)-3-(2-phenoxyphenyl)thiourea	aromatic ether		low
N-[3-[2-(1-azepanyl)-4,5-dicyanophenoxy]phenyl]acetamide	aromatic ether		low
2,5-dimethoxy-N-(4-phenoxyphenyl)benzenesulfonamide	aromatic ether		low
4-[[4-(dimethylamino)-6-(4-morpholinyl)-1,3,5-triazin-2-yl]oxy]benzoic acid methyl ester	aromatic ether		low
N-[5-[(4-chlorophenoxy)methyl]-1,3,4-thiadiazol-2-yl]-5-methyl-3-phenyl-4-isoxazolecarboxamide	aromatic ether		low
1-[4-[[4-(2-chloro-6-nitrophenoxy)phenyl]methoxy]phenyl]ethanone	aromatic ether		low
N-[4-[[2-(4-hydroxyphenyl)-1,3-dioxo-5-isoindolyl]oxy]phenyl]-2,2-dimethylpropanamide	aromatic ether		low
N-[[4-(4-chlorophenoxy)anilino]-sulfanylidenemethyl]benzamide	aromatic ether		low
2-(4-fluorophenoxy)-N-(5-pyridin-4-yl-1,3,4-thiadiazol-2-yl)acetamide	aromatic ether		low
4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]-N-propan-2-ylbenzenesulfonamide	aromatic ether		low
4-(4-tert-butylphenoxy)-5-methoxy-2-phenylpyrimidine	aromatic ether		low
4-phenoxy-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester	aromatic ether		low
Src Inhibitor-1	aromatic ether; polyether; quinazolines; secondary amino compound	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
N-[2,5-dioxo-6-(4-phenoxyphenyl)-3-pyrano[3,2-c]pyridinyl]benzamide	aromatic ether		low
2-(4-chlorophenoxy)-4-(dimethylamino)-3-pyridinecarbonitrile	aromatic ether		low
6-methyl-5-[2-(2-methylphenoxy)ethyl]-2-sulfanylidene-1H-pyrimidin-4-one	aromatic ether		low
4-(4-chlorophenoxy)-1-(4-morpholinyl)-1-butanone	aromatic ether		low
N4-ethyl-6-[2-(4-methylphenoxy)ethylthio]-N2-propan-2-yl-1,3,5-triazine-2,4-diamine	aromatic ether		low
4-(phenylmethyl)-3-[2-(4-propoxyphenyl)ethyl]-1H-1,2,4-triazole-5-thione	aromatic ether		low
1-[[1-oxo-3-(4-propan-2-yloxyphenyl)propyl]amino]-3-(phenylmethyl)thiourea	aromatic ether		low
N-[3-(3-methylphenoxy)-5-nitrophenyl]-2-(3-nitro-1,2,4-triazol-1-yl)acetamide	aromatic ether		low
N-bis(2-fluorophenoxy)phosphoryl-3,4-dimethylaniline	aromatic ether		low
2-[[4-(2-ethoxyanilino)-6-(4-ethoxyanilino)-2-pyrimidinyl]methylidene]propanedinitrile	aromatic ether		low
5-methyl-3-[(4-pentoxyphenyl)methylthio]-1H-1,2,4-triazole	aromatic ether		low
4,5-dichloro-1-[2-(4-chlorophenoxy)ethyl]imidazole	aromatic ether		low
1-butyl-3-(4-phenoxyphenyl)thiourea	aromatic ether		low
N-(3-cyano-2-thiophenyl)-2-[4-(1,3,4-oxadiazol-2-yl)phenoxy]acetamide	aromatic ether		low
2-(2-bromophenyl)-5-[(2-chlorophenoxy)methyl]-1,3,4-oxadiazole	aromatic ether		low
5-(4-ethoxyphenyl)-N-(3,4,5,6-tetrahydro-2H-azepin-7-yl)-1,3,4-oxadiazol-2-amine	aromatic ether		low
4-(4-chloro-2-methylphenoxy)-1-(4-morpholinyl)-1-butanone	aromatic ether		low
N9-(4-butoxyphenyl)-6,8,10-triazaspiro[4.5]deca-6,9-diene-7,9-diamine	aromatic ether		low
2-[2-(4-chlorophenoxy)ethylthio]pyrimidine	aromatic ether		low
5-(3-phenoxypropyl)-3-(3-pyridinyl)-1,2,4-oxadiazole	aromatic ether		low
N-[(3-ethoxy-2-prop-2-enoxyphenyl)methyl]-2-thiazolamine	aromatic ether		low
2-(2-bromophenoxy)-N-(2-pyridinylmethyl)acetamide	aromatic ether		low
4-[2-[(4-chlorophenyl)thio]ethoxy]-3-ethoxybenzaldehyde	aromatic ether		low
1-(3-fluorophenyl)-4-(4-hydroxy-3-methoxy-5-nitrophenyl)-4H-pyridine-3,5-dicarboxylic acid diethyl ester	aromatic ether; C-nitro compound		low
5-(2-ethoxyphenyl)-3H-1,3,4-oxadiazole-2-thione	aromatic ether		low
N-tert-butyl-4-(2-fluorophenoxy)-1-butanamine	aromatic ether		low
N-butyl-4-phenoxy-1-butanamine	aromatic ether		low
N-[3-[[diethylamino(sulfanylidene)methyl]thio]-1-oxopropyl]carbamic acid (4-methylphenyl) ester	aromatic ether		low
1,3-dimethyl-5-[[2-[2-(4-nitrophenoxy)ethoxy]phenyl]methylidene]-1,3-diazinane-2,4,6-trione	aromatic ether; C-nitro compound		low
4-[2-[2-(4-bromo-2-chlorophenoxy)ethoxy]ethyl]morpholine	aromatic ether		low
2-[2-(3-ethylphenoxy)ethyl]propanedioic acid diethyl ester	aromatic ether		low
2,3-dihydro-1,4-dioxin-5-carboxylic acid [2-[4-[4-(2-methylbutan-2-yl)phenoxy]anilino]-2-oxoethyl] ester	aromatic ether		low
1-[3-(2-bromo-4-chlorophenoxy)propyl]-4-methylpiperidine	aromatic ether		low
N4-(2-methoxyphenyl)benzene-1,4-diamine	aromatic ether; substituted aniline		low
4-(1H-benzimidazol-2-ylthio)butanoic acid [2-oxo-2-(4-phenoxyanilino)ethyl] ester	aromatic ether		low
2-phenoxybenzoic acid [2-(2-furanylmethylamino)-2-oxoethyl] ester	aromatic ether		low
1-[2,5-dimethyl-1-(phenylmethyl)-3-pyrrolyl]-2-[4-(1,3,4-oxadiazol-2-yl)phenoxy]ethanone	aromatic ether		low
N-[6-amino-1-(2-methylpropyl)-2,4-dioxo-5-pyrimidinyl]-2-(2-methylphenoxy)-N-(2-methylpropyl)acetamide	aromatic ether		low
4-[[6-[(2-methyl-5-thieno[2,3-e][1,3]benzothiazolyl)oxy]-3-pyridinyl]sulfonyl]morpholine	aromatic ether		low
5-(3-fluorophenoxy)-8-nitroisoquinoline	aromatic ether		low
1-[4-(2-prop-2-enylphenoxy)butyl]pyrrolidine	aromatic ether		low
2-(2,4-dibromophenoxy)-N-[oxo-(propan-2-ylamino)methyl]acetamide	aromatic ether		low
4-phenoxyphenyl 4-hydroxypiperidine-1-carboxylate	aromatic ether		low
N'-benzoyl-5-(3,5-dichlorophenoxy)-2-furancarbohydrazide	aromatic ether		low
1-[2-[(4-chlorophenoxy)methyl]-4-thiazolyl]ethanone	aromatic ether		low
5-(benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one	aromatic ether		low
2-(4-aminophenoxy)isophthalonitrile	aromatic ether		low
N5-(2-chloro-6-phenoxybenzyl)-1H-1,2,4-triazole-3,5-diamine	aromatic ether		low
N-[(2-chloro-6-phenoxyphenyl)methyl]benzenesulfonamide	aromatic ether		low
N-[5-(tert-butyl)-3-isoxazolyl]-N'-[2-(trifluoromethoxy)phenyl]urea	aromatic ether		low
6-(4-methoxyphenoxy)-2-imidazo[1,2-b]pyridazinecarboxylic acid ethyl ester	aromatic ether		low
2-fluoro-N-[2,2,2-trichloro-1-[[(4-methoxy-2-nitroanilino)-sulfanylidenemethyl]amino]ethyl]acetamide	aromatic ether; C-nitro compound		low
2-amino-4-(4,5-dimethoxy-2-nitrophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-1-benzopyran-3-carbonitrile	aromatic ether; C-nitro compound		low
2,4-dichloro-N-[2,2,2-trichloro-1-[[(4-methoxy-2-nitroanilino)-sulfanylidenemethyl]amino]ethyl]benzamide	aromatic ether; C-nitro compound		low
1-anilino-3-[4-(3-anilino-2-hydroxypropoxy)phenoxy]-2-propanol	aromatic ether		low
1-[4-(3-ethoxyphenoxy)butyl]imidazole	aromatic ether		low
N-[5-[(4-chlorophenoxy)methyl]-1,3,4-thiadiazol-2-yl]-2-oxolanecarboxamide	aromatic ether		low
1-[[2-(2,4-difluorophenoxy)-1-oxopropyl]amino]-3-(2-oxolanylmethyl)thiourea	aromatic ether		low
N-[[(5-bromo-6-methyl-2-pyridinyl)amino]-sulfanylidenemethyl]-2-(2-chlorophenoxy)acetamide	aromatic ether		low
2-[(4-chlorophenyl)sulfonyl-methylamino]-N-(4-methoxy-2-nitrophenyl)acetamide	aromatic ether; C-nitro compound		low
4-oxido-3-(4-phenoxyphenyl)-4a,5,6,7,8,8a-hexahydroquinoxalin-1-ium 1-oxide	aromatic ether		low
1-(2-fluorophenyl)-3-(4-methoxy-2-nitrophenyl)urea	aromatic ether; C-nitro compound		low
2-[[5-[(2-fluorophenoxy)methyl]-4-prop-2-enyl-1,2,4-triazol-3-yl]thio]-N-[(2-furanylmethylamino)-oxomethyl]acetamide	aromatic ether		low
cyclopropanecarboxylic acid [2-oxo-2-(4-phenoxyanilino)ethyl] ester	aromatic ether		low
toremifene	aromatic ether; organochlorine compound; tertiary amine	antineoplastic agent; bone density conservation agent; estrogen antagonist; estrogen receptor modulator	low
dieckol	aromatic ether; oxacycle; phlorotannin	anticoagulant; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; metabolite; radical scavenger	low
2-[(2-ethoxyphenoxy)-phenylmethyl]morpholine	aromatic ether		low
naproxol	aromatic ether	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
tamoxifen n-oxide	aromatic ether; tertiary amine oxide	anti-estrogen; metabolite	low
diafenthiuron	aromatic ether; thiourea acaricide; thiourea insecticide	oxidative phosphorylation inhibitor; proinsecticide	low
ospemifene	aromatic ether; organochlorine compound; primary alcohol	anti-inflammatory agent; antineoplastic agent; estrogen receptor modulator	low
tandutinib	aromatic ether; N-arylpiperazine; N-carbamoylpiperazine; phenylureas; piperidines; quinazolines; tertiary amino compound	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
adefovir	aromatic ether; aromatic ketone; biaryl; cyclic ketone; naphtho-gamma-pyrone; organooxygen heterocyclic antibiotic; polyphenol	antimalarial; Aspergillus metabolite; marine metabolite	low
3-chloro-N-[2,2,2-trichloro-1-[[(4-methoxy-2-nitroanilino)-sulfanylidenemethyl]amino]ethyl]benzamide	aromatic ether; C-nitro compound		low
N-(2-hydroxyethyl)-4-[2-nitro-4-(trifluoromethyl)phenoxy]benzamide	aromatic ether		low
N'-[2-[(4-amino-5-cyano-2-pyrimidinyl)thio]-1-oxoethyl]-2-(4-methylphenoxy)acetohydrazide	aromatic ether		low
N-[(2-methyl-4-thiazolyl)methyl]-4-phenoxybenzenesulfonamide	aromatic ether		low
6-amino-4-(2-ethoxy-4-hydroxyphenyl)-3-propyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile	aromatic ether; pyranopyrazole		low
1-[(2-ethoxyphenyl)methyl]-3-thiophen-2-ylurea	aromatic ether		low
nafadotride	aromatic ether; naphthalenecarboxamide; nitrile; pyrrolidines; tertiary amino compound	dopaminergic antagonist	low
1-(1-naphthalenyl)-3-[[2-(2-nitrophenoxy)-1-oxoethyl]amino]urea	aromatic ether; C-nitro compound		low
2-methyl-1,3-bis(phenylmethoxy)benzene	aromatic ether		low
1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethoxyphenoxysulfonyl)urea	aromatic ether		low
3-[(4-ethylphenoxy)methyl]-4-(6-methylheptan-2-yl)-1H-1,2,4-triazole-5-thione	aromatic ether		low
2-chloro-N-(2-methyl-6-oxo-5H-benzo[b][1,4]benzoxazepin-8-yl)acetamide	aromatic ether		low
5-(benzenesulfonyl)-4-(2,6-dimethylphenoxy)-2-phenylpyrimidine	aromatic ether		low
4-(2-methylphenoxy)-6-phenylfuro[2,3-d]pyrimidine	aromatic ether		low
1-[4-(2-chlorophenoxy)butyl]imidazole	aromatic ether; imidazoles; monochlorobenzenes		low
N-(2-chlorophenyl)-4-[[(2-methoxy-4-nitroanilino)-sulfanylidenemethyl]hydrazo]-4-oxobutanamide	aromatic ether; C-nitro compound		low
N-(2-methoxy-4-nitrophenyl)-2-[(1-methyl-2-imidazolyl)thio]acetamide	aromatic ether; C-nitro compound		low
N-[4-(phenoxymethyl)-2-thiazolyl]-1-adamantanecarboxamide	aromatic ether		low
hydroxypioglitazone	aromatic ether; pyridines; thiazolidinediones	human xenobiotic metabolite	low
sc 560	aromatic ether; monochlorobenzenes; organofluorine compound; pyrazoles	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; cyclooxygenase 1 inhibitor; non-steroidal anti-inflammatory drug	low
sc-19220	aromatic ether		low
5-methyl-4-(3-phenoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-6-carboxylic acid ethyl ester	aromatic ether		low
8-[4-(4-fluorophenoxy)-3-nitrophenyl]-7-(2-hydroxyethyl)-3-(phenylmethyl)purine-2,6-dione	aromatic ether		low
2-phenoxybenzoic acid [2-oxo-2-(propan-2-ylamino)ethyl] ester	aromatic ether		low
2-(4-bromophenoxy)-N'-[2-[(4-methyl-1,2,4-triazol-3-yl)thio]-1-oxoethyl]acetohydrazide	aromatic ether		low
2-(2-methoxyanilino)-2-(2-phenylmethoxyphenyl)acetonitrile	aromatic ether; substituted aniline		low
N-(4-phenoxyphenyl)-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)acetamide	aromatic ether		low
5-(3,4-dimethoxyphenyl)-3-(2-furanylmethyl)-4-imino-5H-[1]benzopyrano[2,3-d]pyrimidin-8-ol	aromatic ether		low
3,3-dimethyl-1,5-dinitro-6-phenoxy-3-azoniabicyclo[3.3.1]non-6-ene	aromatic ether		low
fraxin	aromatic ether; beta-D-glucoside; hydroxycoumarin	anti-inflammatory agent; hepatoprotective agent; plant metabolite	low
fraxetin	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent	low
5,6-dehydrokawain	2-pyranones; aromatic ether		low
jtk-303	aromatic ether; monochlorobenzenes; organofluorine compound; quinolinemonocarboxylic acid; quinolone	HIV-1 integrase inhibitor	low
coniferin	aromatic ether; cinnamyl alcohol beta-D-glucoside; monosaccharide derivative	plant metabolite	low
daphnoretin	aromatic ether; hydroxycoumarin	antineoplastic agent; antiviral agent; metabolite	low
kavain	2-pyranones; aromatic ether		low
methysticin	2-pyranones; aromatic ether		low
yangonin	2-pyranones; aromatic ether		low
hinokiflavone	aromatic ether; biflavonoid; hydroxyflavone	antineoplastic agent; metabolite; neuroprotective agent	low
gentiacaulein	aromatic ether; polyphenol; xanthones	plant metabolite	low
gentisin	aromatic ether; polyphenol; xanthones	plant metabolite	low
isogentisin	aromatic ether; polyphenol; xanthones	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite	low
mangostin	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite	low
1,8-dihydroxy-3,7-dimethoxyxanthone	aromatic ether; polyphenol; xanthones	plant metabolite	low
swerchirin	aromatic ether; phenols; xanthones	hypoglycemic agent; metabolite	low
1,2,8-trihydroxy-6-methoxyxanthone	aromatic ether; polyphenol; xanthones	antioxidant; plant metabolite	low
wedelolactone	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; apoptosis inducer; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; hepatoprotective agent; metabolite	low
cyhalothrin	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound; organofluorine compound	agrochemical; pyrethroid ester acaricide; pyrethroid ester insecticide	low
sofalcone	aromatic ether; chalcones; monocarboxylic acid	anti-ulcer drug; antibacterial agent; gastrointestinal drug; plant metabolite	low
neticonazole	aromatic ether; benzenes; conazole antifungal drug; enamine; imidazole antifungal drug; imidazoles; methyl sulfide	antifungal drug; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor	low
pibutidine	aromatic ether; cyclobutenones; olefinic compound; piperidines; primary amino compound; pyridines; secondary amino compound	anti-ulcer drug; H2-receptor antagonist	low
purmorphamine	aromatic ether; morpholines; purines; secondary amino compound	osteogenesis regulator; SMO receptor agonist	low
8-(2-chlorophenyl)-3-(4-ethoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile	aromatic ether		low
ro 41-5253	aromatic ether; benzoic acids; sulfone; thiochromane	apoptosis inducer; retinoic acid receptor alpha antagonist	low
glycycoumarin	aromatic ether; coumarins; resorcinols	antispasmodic drug; plant metabolite	low
isoginkgetin	aromatic ether; biflavonoid	antineoplastic agent; EC 3.4.24.35 (gelatinase B) inhibitor; plant metabolite	low
neoglycyrol	aromatic ether; coumestans; delta-lactone; polyphenol	antineoplastic agent; plant metabolite	low
rhamnazin	aromatic ether; dimethoxyflavone; phenols; trihydroxyflavone	antineoplastic agent; plant metabolite	low
bosutinib	aminoquinoline; aromatic ether; dichlorobenzene; N-methylpiperazine; nitrile; tertiary amino compound	antineoplastic agent; tyrosine kinase inhibitor	low
bw b70c	aromatic ether; hydroxamic acid; organofluorine compound; ureas	EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor	low
lichexanthone	aromatic ether; phenols; xanthones	plant metabolite	low
alternariol monomethyl ether	aromatic ether; benzochromenone	antifungal agent; fungal metabolite; mycotoxin	low
decussatin	aromatic ether; phenols; xanthones	plant metabolite	low
dimethomorph	aromatic ether; enamide; monochlorobenzenes; morpholine fungicide; tertiary carboxamide		low
benanomicin b	aromatic ether; disaccharide derivative; L-alanine derivative; polyketide; polyphenol; pradimicin; secondary alcohol		low
pradimicin b	aromatic ether; L-alanine derivative; monosaccharide derivative; polyketide; polyphenol; pradimicin; secondary alcohol		low
1,7-dihydroxy-4-methoxyxanthone	aromatic ether; phenols; xanthones	metabolite; plant metabolite	low
pradimicin a	aromatic ether; carboxylic acid; disaccharide derivative; L-alanine derivative; p-quinones; polyphenol; pradimicin; secondary alcohol		low
clodinafop	aromatic ether; monocarboxylic acid; organochlorine compound; organofluorine compound; pyridines	EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; phenoxy herbicide	low
ici 118551	aromatic ether; indanes; secondary alcohol; secondary amino compound	beta-adrenergic antagonist	low
ochnaflavone	aromatic ether; biflavonoid; hydroxyflavone	anti-inflammatory agent; antiatherogenic agent; antibacterial agent; EC 3.1.1.4 (phospholipase A2) inhibitor; leukotriene antagonist; plant metabolite	low
3-(4-fluorophenoxy)-6-methoxy-2-(4-methoxyphenyl)-1-benzothiophene 1-oxide	aromatic ether		low
flavasperone	aromatic ether; naphtho-gamma-pyrone; phenols	acyl-CoA:cholesterol acyltransferase 2 inhibitor; antiviral agent; Aspergillus metabolite; marine metabolite	low
4-hydroxycordoin	aromatic ether; chalcones; polyphenol	anti-inflammatory agent; antibacterial agent; plant metabolite	low
n-feruloylserotonin	aromatic ether; cinnamamides; hydroxyindoles; phenols; secondary carboxamide	plant metabolite	low
tyrphostin ag825	aromatic ether; benzothiazoles; enamide; nitrile; organic sulfide; phenols; primary carboxamide	epidermal growth factor receptor antagonist	low
kresoxim-methyl	aromatic ether; methoxyiminoacetate strobilurin antifungal agent; methyl ester; oxime O-ether	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; xenobiotic	low
5-methoxy-3,6-diphenyl-1,2,4-triazine	aromatic ether		low
pyrachlostrobin	aromatic ether; carbamate ester; carbanilate fungicide; methoxycarbanilate strobilurin antifungal agent; monochlorobenzenes; pyrazoles	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; xenobiotic	low
piericidin a	aromatic ether; methylpyridines; monohydroxypyridine; secondary allylic alcohol	antimicrobial agent; bacterial metabolite; EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor; mitochondrial respiratory-chain inhibitor	low
2-(4-fluoro-3-(trifluoromethyl)phenoxy)-n-(phenylmethyl)butanamide	(trifluoromethyl)benzenes; aromatic ether; monocarboxylic acid amide; monofluorobenzenes		low
b 43	aromatic amine; aromatic ether; cyclopentanes; primary amino compound; pyrrolopyrimidine	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector	low
5-(4-phenylbutoxy)psoralen	aromatic ether; benzenes; psoralens	geroprotector; immunosuppressive agent; potassium channel blocker	low
5-ia-85380	aromatic ether		low
yunaconitine	acetate ester; aromatic ether; benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound	antifeedant; human urinary metabolite; phytotoxin; plant metabolite; xenobiotic	low
ru 58668	17beta-hydroxy steroid; 3-hydroxy steroid; aromatic ether; organofluorine compound; sulfone	anti-estrogen; antineoplastic agent; estrogen receptor antagonist	low
altenusin	aromatic ether; carboxybiphenyl; catechols; hydroxybiphenyls; polyphenol	antifungal agent; fungal metabolite	low
gw 501516	1,3-thiazoles; aromatic ether; aryl sulfide; monocarboxylic acid; organofluorine compound	carcinogenic agent; PPARbeta/delta agonist	low
bay 58-2667	aromatic ether; benzoic acids; dicarboxylic acid; tertiary amino compound	antihypertensive agent; soluble guanylate cyclase activator; vasodilator agent	low
camostat	aromatic ether; phenols		low
nsc 716970	aromatic amine; aromatic ether; indolecarboxamide; organochlorine compound	antineoplastic agent	low
lobeglitazone	aromatic ether		low
noviflumuron	aromatic ether; benzoylurea insecticide; dichlorobenzene; organofluorine compound		low
etomoxir	aromatic ether		low
fr 148083	aromatic ether; macrolide; phenols; secondary alcohol; secondary alpha-hydroxy ketone	antibacterial agent; antineoplastic agent; metabolite; NF-kappaB inhibitor	low
9-methoxycanthin-6-one	aromatic ether; indole alkaloid; organic heterotetracyclic compound	antineoplastic agent; antiplasmodial drug; metabolite	low
sb 3ct compound	aromatic ether		low
varespladib methyl	aromatic ether; benzenes; indoles; methyl ester; primary carboxamide	anti-inflammatory drug; antidote; EC 3.1.1.4 (phospholipase A2) inhibitor; prodrug	low
dapagliflozin	aromatic ether; C-glycosyl compound; monochlorobenzenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor	low
naveglitazar	aromatic ether		low
tivozanib	aromatic ether		low
zm 447439	aromatic ether; benzamides; morpholines; polyether; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; apoptosis inducer; Aurora kinase inhibitor	low
ustiloxin b	aromatic ether; heterodetic cyclic peptide; macrocycle; phenols; secondary alcohol; secondary carboxamide; sulfoxide	Aspergillus metabolite; microtubule-destabilising agent; mycotoxin	low
hypothemycin	aromatic ether; diol; enone; epoxide; macrolide; phenols; polyketide; secondary alpha-hydroxy ketone	antifungal agent; antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; fungal metabolite	low
tryprostatin a	aromatic ether; dipeptide; indole alkaloid; indoles; pyrrolopyrazine	breast cancer resistance protein inhibitor	low
cediranib	aromatic ether		low
3-iodothyronamine	aromatic ether		low
n,n-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride	aromatic ether; hydrochloride; methoxybenzenes; tertiary amino compound	antipsychotic agent; receptor modulator	low
rubraxanthone	aromatic ether; polyphenol; xanthones	antibacterial agent; antineoplastic agent; metabolite	low
7,8-Dihydroyangonin	2-pyranones; aromatic ether		low
sch 51344	aromatic amine; aromatic ether; primary alcohol; pyrazoloquinoline; secondary amino compound	antineoplastic agent	low
ancistroealaine a	aromatic ether; biaryl; isoquinoline alkaloid; isoquinolines; methoxynaphthalene; methylnaphthalenes	antileishmanial agent; antiplasmodial drug; metabolite; trypanocidal drug	low
pimavanserin	aromatic ether; monofluorobenzenes; piperidines; tertiary amino compound; ureas	5-hydroxytryptamine 2A receptor inverse agonist; antipsychotic agent; serotonergic antagonist	low
tolfenpyrad	aromatic amide; aromatic ether; organochlorine compound; pyrazole insecticide	agrochemical; antifungal agent; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor	low
SIS3 free base	aromatic ether; enamide; isoquinolines; monocarboxylic acid amide; pyrrolopyridine; tertiary carboxamide	Smad3 inhibitor	low
apixaban	aromatic ether; lactam; piperidones; pyrazolopyridine	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor	low
bibw 2992	aromatic ether; enamide; furans; monochlorobenzenes; organofluorine compound; quinazolines; secondary carboxamide; tertiary amino compound	antineoplastic agent; tyrosine kinase inhibitor	low
dihydrokavain	2-pyranones; aromatic ether		low
troglitazone sulfate	aromatic ether; thiazolidinone		low
arisugacin	aromatic ether; delta-lactone; enone; organic heterotetracyclic compound; tertiary alcohol	antimicrobial agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite; Penicillium metabolite	low
saracatinib	aromatic ether; benzodioxoles; diether; N-methylpiperazine; organochlorine compound; oxanes; quinazolines; secondary amino compound	anticoronaviral agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; radiosensitizing agent	low
fonsecinone a	aromatic ether; aromatic ketone; biaryl; cyclic ketone; naphtho-gamma-pyrone; polyphenol	antibacterial agent; Aspergillus metabolite	low
aiphanol	aromatic ether; benzodioxine; lignan; stilbenoid	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor	low
nigerloxin	aromatic ether; benzamides; benzoic acids; phenols; styrenes	antioxidant; Aspergillus metabolite; EC 1.1.1.21 (aldehyde reductase) inhibitor; lipoxygenase inhibitor; radical scavenger	low
msdc-0160	aromatic ether		low
dihydroxanthohumol	aromatic ether; dihydrochalcones; polyphenol	EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite	low
PB28	aromatic ether; piperazines; tetralins	anticoronaviral agent; antineoplastic agent; apoptosis inducer; sigma-2 receptor agonist	low
7-phloroeckol	aromatic ether; phlorotannin	antioxidant; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; metabolite	low
3,5-dimethoxy-4-hydroxybenzyl alcohol-4-O-beta-D-glucopyranoside	aromatic ether; benzyl alcohols; beta-D-glucoside; monosaccharide derivative; primary alcohol	antineoplastic agent; metabolite	low
PDGF receptor tyrosine kinase inhibitor III	aromatic ether; N-arylpiperazine; N-carbamoylpiperazine; phenylureas; quinazolines; tertiary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
fluoxastrobin	aromatic ether; dioxazine; monochlorobenzenes; organofluorine compound; oxime O-ether; pyrimidines; strobilurin antifungal agent	antifungal agrochemical; mitochondrial cytochrome-bc1 complex inhibitor	low
flumorph	aromatic ether; enamide; morpholines; organofluorine compound; tertiary carboxamide		low
regorafenib	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; monofluorobenzenes; phenylureas; pyridinecarboxamide	antineoplastic agent; hepatotoxic agent; tyrosine kinase inhibitor	low
erastin	aromatic ether; diether; monochlorobenzenes; N-acylpiperazine; N-alkylpiperazine; quinazolines; tertiary carboxamide	antineoplastic agent; ferroptosis inducer; voltage-dependent anion channel inhibitor	low
brivanib	aromatic ether; diether; fluoroindole; pyrrolotriazine; secondary alcohol	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; drug metabolite; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; fibroblast growth factor receptor antagonist	low
fg-4592	aromatic ether; isoquinolines; N-acylglycine	EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; EC 1.14.11.29 (hypoxia-inducible factor-proline dioxygenase) inhibitor	low
picoxystrobin	aromatic ether; enoate ester; enol ether; methoxyacrylate strobilurin antifungal agent; organofluorine compound; pyridines	antifungal agrochemical; mitochondrial cytochrome-bc1 complex inhibitor	low
cenicriviroc	aromatic ether; benzazocine; diether; imidazoles; secondary carboxamide; sulfoxide	anti-HIV agent; anti-inflammatory agent; antirheumatic drug; chemokine receptor 2 antagonist; chemokine receptor 5 antagonist	low
mandipropamid	aromatic ether; monocarboxylic acid amide; monochlorobenzenes; terminal acetylenic compound		low
glyceryl ferulate	1-monoglyceride; aromatic ether; enoate ester; phenols	antioxidant; plant metabolite; ultraviolet filter	low
ki 8751	aromatic ether		low
azd 8931	aromatic ether; monochlorobenzenes; monofluorobenzenes; piperidines; quinazolines; secondary amino compound; tertiary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist	low
bay94 9172	(18)F radiopharmaceutical; aromatic ether; polyether; secondary amino compound; stilbenoid; substituted aniline	radioactive imaging agent	low
olodaterol	aromatic ether; benzoxazine; phenols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent	low
dorsomorphin	aromatic ether; piperidines; pyrazolopyrimidine; pyridines	bone morphogenetic protein receptor antagonist; EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} inhibitor	low
cj-042794	aromatic ether		low
hu 308	aromatic ether; bridged compound; carbobicyclic compound; primary allylic alcohol; synthetic cannabinoid	anti-inflammatory agent; antihypertensive agent; apoptosis inhibitor; bone density conservation agent; CB2 receptor agonist	low
apremilast	aromatic ether; N-acetylarylamine; phthalimides; sulfone	non-steroidal anti-inflammatory drug; phosphodiesterase IV inhibitor	low
PF-00835231	aromatic ether; indolecarboxamide; L-leucine derivative; primary alcohol; pyrrolidin-2-ones; secondary carboxamide	anticoronaviral agent; drug metabolite; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor	low
3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine	aminopyridine; aromatic ether; dichlorobenzene; organofluorine compound; pyrazolylpiperidine; racemate	antineoplastic agent; biomarker; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
chir-265	aromatic ether		low
aminocandin	aromatic ether; echinocandin; homodetic cyclic peptide	antiinfective agent	low
zk 756326	aromatic ether		low
bay 60-6583	aminopyridine; aromatic ether; aryl sulfide; cyanopyridine; cyclopropanes; monocarboxylic acid amide	adenosine A2B receptor agonist; anti-inflammatory agent; cardioprotective agent	low
empagliflozin	aromatic ether; C-glycosyl compound; monochlorobenzenes; tetrahydrofuryl ether	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor	low
4-[5-(4-ethoxyphenyl)-3-isoxazolyl]-N-[(4-methylphenyl)methyl]butanamide	aromatic ether		low
bgt226	aromatic ether; imidazoquinoline; N-arylpiperazine; organofluorine compound; pyridines	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor	low
n-desmethylrosiglitazone	aromatic ether		low
4-(5-methyl-3-nitro-1-pyrazolyl)-N-[3-(4-methylphenoxy)-5-nitrophenyl]butanamide	aromatic ether		low
verruculogen	aromatic ether; diol; indole alkaloid; organic heterohexacyclic compound; organic peroxide	Aspergillus metabolite; GABA modulator; mycotoxin; Penicillium metabolite; potassium channel blocker	low
1-O-feruloyl-beta-D-glucose	aromatic ether; beta-D-glucoside; cinnamate ester; phenols	antioxidant; plant metabolite	low
l-798106	aromatic ether; bromobenzenes; N-sulfonylcarboxamide	prostaglandin receptor antagonist	low
aflatoxin m1	aflatoxin; aromatic ether; aromatic ketone; tertiary alcohol	Aspergillus metabolite; human xenobiotic metabolite; mammalian metabolite	low
e 7050	aromatic ether		low
N-[(5-chloro-2-thiophenyl)methyl]-5-[(2,6-difluorophenoxy)methyl]-3-isoxazolecarboxamide	aromatic ether		low
dafadine C	aromatic amide; aromatic ether; difluorobenzene; isoxazoles; N-acylpiperidine; pyridines	P450 inhibitor	low
dafadine B	aromatic amide; aromatic ether; isoxazoles; monochlorobenzenes; monofluorobenzenes; N-acylpiperidine; pyridines	P450 inhibitor	low
3-[5-(5-methyl-2-thiophenyl)-1,3,4-oxadiazol-2-yl]-N-[2-(3-pyridinyloxy)propyl]propanamide	aromatic ether		low
violaceol II	aromatic ether; catechols; resorcinols	mycotoxin	low
pamapimod	aromatic amine; aromatic ether; difluorobenzene; diol; primary alcohol; pyridopyrimidine; secondary amino compound	antirheumatic drug; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
gsk690693	1,2,5-oxadiazole; acetylenic compound; aromatic amine; aromatic ether; imidazopyridine; piperidines; primary amino compound; tertiary alcohol	antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
cnf 2024	2-aminopurines; aromatic ether; organochlorine compound; pyridines	antineoplastic agent; Hsp90 inhibitor	low
uk 453,061	aromatic ether		low
8-{1-[4-(dimethylamino)phenyl]-3-(pyrrolidin-1-yl)propyl}-5,7-dimethoxy-4-pentyl-2H-chromen-2-one	aromatic ether; coumarins; pyrrolidines; tertiary amino compound		low
zm323881	aromatic ether; benzyl ether; fluorophenol; halophenol; monofluorobenzenes; organic cation; quinazolines; secondary amino compound; substituted aniline	vascular endothelial growth factor receptor antagonist	low
compound w	aromatic ether		low
2-[[4-[2-[(2-methylpropan-2-yl)oxy]anilino]-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	aromatic ether		low
interiotherin b	aromatic ether; fatty acid ester; lignan; organic heteropentacyclic compound; oxacycle	anti-HIV agent; metabolite	low
5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-6-methoxychroman-4-one	aromatic ether; homoisoflavonoid; polyphenol	angiogenesis modulating agent; plant metabolite	low
diorcinol	aromatic ether; phenols	fungal metabolite; marine metabolite; metabolite	low
2-[[4-(2-phenoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	aromatic ether		low
2-[[4-(1-pyrrolidinyl)-6-[2-(trifluoromethoxy)anilino]-1,3,5-triazin-2-yl]amino]ethanol	aromatic ether		low
2-[[4-(5-chloro-2-ethoxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	aromatic ether		low
2-[[4-(5-chloro-2-propan-2-yloxyanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	aromatic ether		low
mk 5108	aromatic ether		low
lde225	aminopyridine; aromatic ether; benzamides; biphenyls; morpholines; organofluorine compound; tertiary amino compound	antineoplastic agent; Hedgehog signaling pathway inhibitor; SMO receptor antagonist	low
1-azepanyl-[5-[(4-chloro-3,5-dimethylphenoxy)methyl]-3-isoxazolyl]methanone	aromatic ether		low
4-(1-((5-((2,6-dimethylphenoxy)methyl)-3-isoxazolyl)carbonyl)-4-piperidinyl)pyridine	aromatic amide; aromatic ether; isoxazoles; N-acylpiperidine; pyridines	geroprotector; P450 inhibitor	low
dafadine D	aromatic amide; aromatic ether; isoxazoles; N-acylpiperidine; organofluorine compound; pyridines	P450 inhibitor	low
1-[(1-ethyl-3-methyl-4-pyrazolyl)methyl]-N-[4-(2-fluorophenoxy)phenyl]-4-piperidinecarboxamide	aromatic ether		low
dafadine O	aromatic amide; aromatic ether; isoxazoles; N-acylpiperidine; pyridines; ring assembly	P450 inhibitor	low
5-[(3,4-dimethylphenoxy)methyl]-N-methyl-N-(4-oxanylmethyl)-3-isoxazolecarboxamide	aromatic ether		low
pci 32765	acrylamides; aromatic amine; aromatic ether; N-acylpiperidine; pyrazolopyrimidine; tertiary carboxamide	antineoplastic agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
florbetapir f 18	(18)F radiopharmaceutical; aromatic ether; organofluorine compound; pyridines; substituted aniline	radioactive imaging agent	low
6-methoxyspirotryprostatin b	aromatic ether; azaspiro compound; indole alkaloid; indolones	antineoplastic agent; Aspergillus metabolite	low
poziotinib	acrylamides; aromatic ether; dichlorobenzene; diether; monofluorobenzenes; N-acylpiperidine; quinazolines; secondary amino compound; substituted aniline	antineoplastic agent; apoptosis inducer; epidermal growth factor receptor antagonist	low
gsk 1363089	aromatic ether		low
1-[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl(methylsulfonyl)amino]methyl]-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-8-yl]-3-propan-2-ylurea	aromatic ether		low
1-[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl(methylsulfonyl)amino]methyl]-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-10-yl]-3-propan-2-ylurea	aromatic ether		low
3-cyclohexyl-1-[[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-8-[[oxo-(propan-2-ylamino)methyl]amino]-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-1-methylurea	aromatic ether		low
3-cyclohexyl-1-[[(2S,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-10-[[oxo-(propan-2-ylamino)methyl]amino]-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-1-methylurea	aromatic ether		low
N-[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl-[(4-phenoxyphenyl)methyl]amino]methyl]-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-10-yl]-4-pyridinecarboxamide	aromatic ether		low
1-(3,5-dimethyl-4-isoxazolyl)-3-[(2R,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-(methylaminomethyl)-6-oxo-2,3,4,7-tetrahydro-1,5-benzoxazonin-9-yl]urea	aromatic ether		low
monepantel	(trifluoromethyl)benzenes; aromatic ether; aryl sulfide; nitrile; secondary carboxamide	anthelminthic drug; nematicide	low
an2728	aromatic ether; benzoxaborole; nitrile	antipsoriatic; non-steroidal anti-inflammatory drug; phosphodiesterase IV inhibitor	low
grazoprevir	aromatic ether; azamacrocycle; carbamate ester; cyclopropanes; lactam; N-sulfonylcarboxamide; quinoxaline derivative	antiviral drug; hepatitis C protease inhibitor; hepatoprotective agent	low
hordatine a	aromatic ether; benzofurans; dicarboxylic acid diamide; guanidines; phenols	adrenergic antagonist; metabolite	low
kavain	2-pyranones; aromatic ether		low
5-chloro-2-(3,5-dimethylphenyl)-4-(4-methoxyphenoxy)-3-pyridazinone	aromatic ether		low
tak-632	(trifluoromethyl)benzenes; aromatic ether; benzothiazoles; cyclopropylcarboxamide; monofluorobenzenes; nitrile; secondary carboxamide	antineoplastic agent; apoptosis inducer; B-Raf inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; necroptosis inhibitor	low
lrrk2-in1	aromatic amine; aromatic ether; N-acylpiperidine; N-alkylpiperazine; pyrimidobenzodiazepine; secondary amino compound; tertiary amino compound	antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
quinolobactin	aromatic ether; monohydroxyquinoline; phenols; quinolinemonocarboxylic acid	bacterial metabolite; siderophore	low
AZD1979	aromatic ether; azaspiro compound; carboxamide; N-acylazetidine; oxadiazole; oxaspiro compound; oxetanes	melanin-concentrating hormone receptor antagonist	low
ML240	aromatic amine; aromatic ether; benzimidazoles; primary amino compound; quinazolines; secondary amino compound	antineoplastic agent	low
aripiprazole lauroxil	aromatic ether; delta-lactam; dichlorobenzene; dodecanoate ester; N-alkylpiperazine; N-arylpiperazine; quinolone	H1-receptor antagonist; prodrug; second generation antipsychotic; serotonergic agonist	low
abt-199	aromatic ether; C-nitro compound; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; N-sulfonylcarboxamide; oxanes; pyrrolopyridine	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor	low
xl765	aromatic amine; aromatic ether; benzamides; quinoxaline derivative; sulfonamide	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor	low
2-methoxy-N-[3-[4-[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]anilino]-6-quinazolinyl]prop-2-enyl]acetamide	aromatic ether; methylpyridines; olefinic compound; quinazolines; secondary amino compound; secondary carboxamide; toluenes		low
pf 4800567	aromatic ether; monochlorobenzenes; oxanes; pyrazolopyrimidine	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
propenylphosphonic acid	aromatic ether		low
naloxegol	aromatic ether; organic heteropentacyclic compound; phenols; polyether; tertiary alcohol	cathartic; mu-opioid receptor antagonist	low
ceritinib	aminopyrimidine; aromatic ether; organochlorine compound; piperidines; secondary amino compound; sulfone	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
MK-8353	aromatic ether; dihydropyridine; indazoles; methyl sulfide; N-alkylpyrrolidine; pyridines; pyrrolidinecarboxamide; secondary carboxamide; tertiary carboxamide; triazoles	antineoplastic agent; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
HG-10-102-01	aminopyrimidine; aromatic ether; monocarboxylic acid amide; morpholines; organochlorine compound; secondary amino compound	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
N-[(5-methyl-2-furanyl)methylideneamino]-2-phenoxybenzamide	aromatic ether		low
saroglitazar	aromatic ether; methyl sulfide; monocarboxylic acid; pyrroles	hypoglycemic agent; PPARalpha agonist; PPARgamma agonist	low
fertaric acid	aromatic ether; cinnamate ester; dicarboxylic acid; phenols; tetraric acid derivative		low
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; tertiary alcohol; triazoles		low
pf-06463922	aminopyridine; aromatic ether; azamacrocycle; benzamides; cyclic ether; monofluorobenzenes; nitrile; organic heterotetracyclic compound; pyrazoles	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
DDR1-IN-1	(trifluoromethyl)benzenes; aromatic ether; benzamides; N-alkylpiperazine; oxindoles; secondary carboxamide	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
ldc4297	aromatic ether; piperidines; pyrazoles; pyrazolotriazine; secondary amino compound	antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor	low
MLI-2	aromatic ether; cyclopropanes; indazoles; morpholines; pyrimidines; tertiary amino compound	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
ap20187	aromatic ether; carboxylic ester; N-acylpiperidine; tertiary amino compound	ligand	low
methysticin	2-pyranones; aromatic ether		low
biliatresone	aromatic ether; aromatic ketone; benzodioxoles; enone; phenols	plant metabolite; toxin	low
tak 491	1,2,4-oxadiazole; aromatic ether; benzimidazoles; carboxylic ester; cyclic carbonate ester; dioxolane	angiotensin receptor antagonist; antihypertensive agent; prodrug	low
azilsartan	1,2,4-oxadiazole; aromatic ether; benzimidazolecarboxylic acid	angiotensin receptor antagonist; antihypertensive agent	low
hydrazinocurcumin	aromatic ether; olefinic compound; polyphenol; pyrazoles	angiogenesis modulating agent; antineoplastic agent; EC 2.3.1.48 (histone acetyltransferase) inhibitor; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
mirodenafil	aromatic ether; N-alkylpiperazine; primary alcohol; pyrrolopyrimidine; sulfonamide	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent	low
cerulomycin	aldoxime; aromatic ether; bipyridines; pyridine alkaloid	antineoplastic agent; bacterial metabolite; marine metabolite	low
undecylprodigiosin	alkaloid; aromatic ether; tripyrrole	antibacterial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite; biological pigment; immunosuppressive agent; radiosensitizing agent	low
sb-590885	aromatic ether; imidazoles; ketoxime; pyridines; tertiary amino compound		low
2-[[4-(trifluoromethoxy)phenyl]methylthio]-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-one	aromatic ether		low
PF-07304814	aromatic ether; indolecarboxamide; L-leucine derivative; phosphate monoester; pyrrolidin-2-ones; secondary carboxamide	anticoronaviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; prodrug	low
threo-alpha-methylisocitrate	methylisocitric acid; tertiary alcohol; tricarboxylic acid		low
meglutol	3-hydroxy carboxylic acid; dicarboxylic acid; tertiary alcohol	anticholesteremic drug; antimetabolite; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; human metabolite; plant metabolite	low
bicalutamide	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol		low
biperiden	piperidines; tertiary alcohol; tertiary amino compound	antidote to sarin poisoning; antidyskinesia agent; antiparkinson drug; muscarinic antagonist; parasympatholytic	low
cyclopentolate	carboxylic ester; tertiary alcohol; tertiary amino compound	diagnostic agent; muscarinic antagonist; mydriatic agent; parasympatholytic	low
cycrimine	piperidines; tertiary alcohol; tertiary amino compound	antidyskinesia agent; antiparkinson drug; muscarinic antagonist	low
diphenidol	benzenes; piperidines; tertiary alcohol	antiemetic	low
fluconazole	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic	low
haloperidol	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist	low
heptaminol	tertiary alcohol		low
loperamide	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	anticoronaviral agent; antidiarrhoeal drug; mu-opioid receptor agonist	low
oxybutynin	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic	low
pridinol	piperidines; tertiary alcohol	antiparkinson drug; muscle relaxant	low
procyclidine	pyrrolidines; tertiary alcohol	antidyskinesia agent; antiparkinson drug; muscarinic antagonist	low
venlafaxine	cyclohexanols; monomethoxybenzene; tertiary alcohol; tertiary amino compound	adrenergic uptake inhibitor; analgesic; antidepressant; dopamine uptake inhibitor; environmental contaminant; serotonin uptake inhibitor; xenobiotic	low
chlorobutanol	tertiary alcohol		low
vincristine	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator	low
norethindrone	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive	low
tert-butyl alcohol	tertiary alcohol	human xenobiotic metabolite	low
tert-amyl alcohol	aliphatic alcohol; tertiary alcohol	protic solvent	low
linalool	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component	low
hydroxycitronellal	tertiary alcohol	allergen; fragrance	low
3-hydroxy-3-methylbutene	olefinic compound; tertiary alcohol	animal metabolite; fragrance; pheromone; plant metabolite	low
dicofol	monochlorobenzenes; organochlorine acaricide; tertiary alcohol		low
hematoxylin	organic heterotetracyclic compound; oxacycle; polyphenol; tertiary alcohol	histological dye; plant metabolite	low
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component	low
2-phenyl-2-propanol	benzyl alcohols; tertiary alcohol	human xenobiotic metabolite; Mycoplasma genitalium metabolite	low
ethylestrenol	17beta-hydroxy steroid; tertiary alcohol	anabolic agent	low
tridihexethyl	quaternary ammonium ion; tertiary alcohol	anti-ulcer drug; antispasmodic drug; muscarinic antagonist	low
camptothecin	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite	low
stanozolol	17beta-hydroxy steroid; anabolic androgenic steroid; organic heteropentacyclic compound; tertiary alcohol	anabolic agent; androgen	low
ancymidol	pyrimidines; tertiary alcohol	cellulose synthesis inhibitor; gibberellin biosynthesis inhibitor; plant growth retardant	low
butaclamol	amino alcohol; organic heteropentacyclic compound; tertiary alcohol; tertiary amino compound	dopaminergic antagonist	low
vindesine	methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; primary carboxamide; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent	low
fenarimol	monochlorobenzenes; pyrimidines; tertiary alcohol		low
irinotecan	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug	low
cedrol	cedrane sesquiterpenoid; tertiary alcohol		low
hexaconazole	dichlorobenzene; tertiary alcohol; triazoles	chelator	low
voriconazole	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor	low
warburganal	tertiary alcohol		low
brazilin	catechols; organic heterotetracyclic compound; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; apoptosis inducer; biological pigment; hepatoprotective agent; histological dye; NF-kappaB inhibitor; plant metabolite	low
tebuconazole	monochlorobenzenes; tertiary alcohol; triazoles		low
cyproconazole	cyclopropanes; monochlorobenzenes; tertiary alcohol; triazoles		low
metconazole	conazole fungicide; cyclopentanols; monochlorobenzenes; tertiary alcohol; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor	low
(1-hydroxycyclopentyl)phenylacetic acid	monocarboxylic acid; tertiary alcohol		low
beta-eudesmol	carbobicyclic compound; eudesmane sesquiterpenoid; tertiary alcohol	volatile oil component	low
flutriafol	monofluorobenzenes; tertiary alcohol; triazoles		low
elemol	olefinic compound; sesquiterpenoid; tertiary alcohol	fragrance; plant metabolite	low
biperiden hydrochloride	hydrochloride; piperidines; tertiary alcohol	antiparkinson drug; muscarinic antagonist; parasympatholytic	low
spathulenol	carbotricyclic compound; olefinic compound; sesquiterpenoid; tertiary alcohol	anaesthetic; plant metabolite; vasodilator agent; volatile oil component	low
alpha-eudesmol	eudesmane sesquiterpenoid; octahydronaphthalenes; tertiary alcohol	volatile oil component	low
aeroplysinin i	tertiary alcohol		low
sn 38	delta-lactone; phenols; pyranoindolizinoquinoline; tertiary alcohol	antineoplastic agent; apoptosis inducer; drug metabolite; EC 5.99.1.2 (DNA topoisomerase) inhibitor	low
paxilline	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker	low
cafestol	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; plant metabolite	low
kahweol	diterpenoid; furans; organic heteropentacyclic compound; primary alcohol; tertiary alcohol	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite	low
megestrol acetate	bridged compound; organic heterotetracyclic compound; secondary alcohol; sesquiterpene lactone; spiro compound; tertiary alcohol; tetrol	GABA antagonist; neurotoxin; phytogenic insecticide; plant metabolite	low
aclacinomycin	aminoglycoside; anthracycline; deoxy hexoside; methyl ester; monosaccharide derivative; phenols; polyketide; tertiary alcohol; tetracenequinones; zwitterion	antimicrobial agent; antineoplastic agent; metabolite	low
columbianetin	furanocoumarin; tertiary alcohol		low
aklavinone	anthracycline; methyl ester; tertiary alcohol; tetracenequinones	antineoplastic agent	low
t-cadinol	cadinane sesquiterpenoid; carbobicyclic compound; octahydronaphthalenes; tertiary alcohol	plant metabolite; volatile oil component	low
withanolide d	20-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; secondary alcohol; tertiary alcohol; withanolide	antineoplastic agent	low
diplopterol	hopanoid; pentacyclic triterpenoid; tertiary alcohol	plant metabolite	low
inuviscolide	gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone; tertiary alcohol	anti-inflammatory agent; plant metabolite	low
diflomotecan	epsilon-lactone; organic heteropentacyclic compound; organofluorine compound; organonitrogen heterocyclic compound; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor	low
vincaleukoblastine	acetate ester; indole alkaloid fundamental parent; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; immunosuppressive agent; microtubule-destabilising agent; plant metabolite	low
Ovalicine subst.	tertiary alcohol		low
homoharringtonine	alkaloid ester; enol ether; organic heteropentacyclic compound; tertiary alcohol	anticoronaviral agent; antineoplastic agent; apoptosis inducer; protein synthesis inhibitor	low
deltaline	acetate ester; cyclic acetal; diterpene alkaloid; organic polycyclic compound; tertiary alcohol; tertiary amino compound		low
phorbol	cyclic ketone; enone; tertiary alcohol; tertiary alpha-hydroxy ketone; tetracyclic diterpenoid		low
picrotin	diol; epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	plant metabolite	low
picrotoxinin	epoxide; gamma-lactone; organic heteropentacyclic compound; picrotoxane sesquiterpenoid; tertiary alcohol	GABA antagonist; plant metabolite; serotonergic antagonist	low
cinnamodial	tertiary alcohol		low
theogallin	gallate ester; monocarboxylic acid; tertiary alcohol		low
kt 5720	carboxylic ester; gamma-lactam; hemiaminal; indolocarbazole; organic heterooctacyclic compound; semisynthetic derivative; tertiary alcohol	EC 2.7.11.11 (cAMP-dependent protein kinase) inhibitor	low
ravuconazole	1,3-thiazoles; fluorobenzenes; nitrile; tertiary alcohol; triazoles	antifungal drug; antileishmanial agent; EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor; ergosterol biosynthesis inhibitor	low
16beta,17-dihydroxy-ent-kaurane-19-oic acid	bridged compound; diol; ent-kaurane diterpenoid; hydroxy monocarboxylic acid; primary alcohol; tertiary alcohol	anti-HIV agent; metabolite	low
rubitecan	C-nitro compound; delta-lactone; pyranoindolizinoquinoline; semisynthetic derivative; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug	low
efinaconazole	conazole antifungal drug; olefinic compound; organofluorine compound; piperidines; tertiary alcohol; tertiary amino compound; triazole antifungal drug	EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor	low
manool	labdane diterpenoid; tertiary alcohol	antibacterial agent; antineoplastic agent; plant metabolite	low
t-muurolol	cadinane sesquiterpenoid; carbobicyclic compound; octahydronaphthalenes; tertiary alcohol	bacterial metabolite; fungicide; marine metabolite; plant metabolite; volatile oil component	low
blister	cyclic ketone; pyrroloquinoline; tertiary alcohol; tertiary alpha-hydroxy ketone	inhibitor	low
senecionine	lactone; pyrrolizidine alkaloid; tertiary alcohol	plant metabolite	low
azadirachtin	acetate ester; azadirachtin; cyclic hemiketal; enoate ester; epoxide; methyl ester; organic heterotetracyclic compound; secondary alcohol; tertiary alcohol	hepatoprotective agent	low
ophiobolin a	cyclic ketone; enal; oxaspiro compound; sesterterpenoid; tertiary alcohol		low
josamycin	acetate ester; aldehyde; disaccharide derivative; glycoside; macrolide antibiotic; tertiary alcohol; tertiary amino compound	antibacterial drug; metabolite	low
ethisterone	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	drug metabolite; progestin	low
naloxone	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist	low
lasalocid	beta-hydroxy ketone; monocarboxylic acid; monohydroxybenzoic acid; oxanes; oxolanes; polyether antibiotic; secondary alcohol; tertiary alcohol	bacterial metabolite; coccidiostat; ionophore	low
rhodopin	carotenol; tertiary alcohol	bacterial metabolite	low
manumycin	enamide; epoxide; organic heterobicyclic compound; polyketide; secondary carboxamide; tertiary alcohol	antiatherosclerotic agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; marine metabolite	low
squalestatin 1	acetate ester; cyclic ketal; oxabicycloalkane; polyketide; tertiary alcohol; tricarboxylic acid	EC 2.5.1.21 (squalene synthase) inhibitor; fungal metabolite	low
riddelliine n-oxide	diol; macrocyclic lactone; olefinic compound; organic heterotricyclic compound; primary alcohol; pyrrolizine alkaloid; tertiary alcohol; tertiary amine oxide	carcinogenic agent; genotoxin; human xenobiotic metabolite; Jacobaea metabolite; mutagen; rat metabolite	low
asukamycin	enamide; epoxide; organic heterobicyclic compound; polyketide; secondary carboxamide; tertiary alcohol	antibacterial agent; antifungal agent; antimicrobial agent; antineoplastic agent; bacterial metabolite	low
bacterioruberin	C50 carotenoid; tertiary alcohol; tetrol	bacterial metabolite; biological pigment	low
prothioconazole	cyclopropanes; monochlorobenzenes; tertiary alcohol; thiocarbonyl compound; triazoles		low
isavuconazole	1,3-thiazoles; conazole antifungal drug; difluorobenzene; nitrile; tertiary alcohol; triazole antifungal drug	EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; ergosterol biosynthesis inhibitor; orphan drug	low
grayanotoxin i	acetate ester; pentol; secondary alcohol; tertiary alcohol; tetracyclic diterpenoid	antihypertensive agent; metabolite; neuromuscular agent; phytotoxin	low
n-demethylloperamide	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	drug metabolite	low
tmc-95a	indoles; lactam; macrocycle; phenols; secondary alcohol; tertiary alcohol	antimicrobial agent; antineoplastic agent; bacterial metabolite; fungal metabolite; proteasome inhibitor	low
yw 3548	olefinic compound; terpene lactone; tertiary alcohol	fungal metabolite; glycerophosphoinositol synthesis inhibitor	low
alpha-cadinol	cadinane sesquiterpenoid; carbobicyclic compound; octahydronaphthalenes; tertiary alcohol	fungicide; plant metabolite; volatile oil component	low
hydroxyibuprofen	hydroxy monocarboxylic acid; tertiary alcohol	drug metabolite	low
tmc-95b	indoles; lactam; macrocycle; phenols; secondary alcohol; tertiary alcohol	antimicrobial agent; antineoplastic agent; fungal metabolite; proteasome inhibitor	low
homocamptothecin	epsilon-lactone; organic heteropentacyclic compound; organonitrogen heterocyclic compound; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor	low
ossamycin	cyclic hemiketal; macrolide antibiotic; organic heterotetracyclic compound; secondary alcohol; spiroketal; tertiary alcohol	antineoplastic agent; bacterial metabolite	low
vibrioferrin	carboxylic ester; N-acyl hemiaminal; pyrrolidin-2-ones; tertiary alcohol; tricarboxylic acid	marine metabolite; siderophore	low
bms 477118	adamantanes; azabicycloalkane; monocarboxylic acid amide; nitrile; tertiary alcohol	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent	low
cubebol	carbotricyclic compound; sesquiterpenoid; tertiary alcohol		low
myrocin a	tertiary alcohol	metabolite	low
diversonol	phenols; tertiary alcohol	antibacterial agent; metabolite	low
zaragozic acid c	acetate ester; cyclic ketal; oxabicycloalkane; polyketide; tertiary alcohol; tricarboxylic acid	EC 2.5.1.21 (squalene synthase) inhibitor; fungal metabolite	low
viridiflorol	carbotricyclic compound; sesquiterpenoid; tertiary alcohol	anti-inflammatory agent; antifeedant; antimycobacterial drug; plant metabolite; volatile oil component	low
oplodiol	carbobicyclic compound; octahydronaphthalenes; secondary alcohol; sesquiterpenoid; tertiary alcohol	plant metabolite	low
kt 5926	gamma-lactam; hemiaminal; indolocarbazole; methyl ester; organic heterooctacyclic compound; tertiary alcohol	EC 2.7.11.18 (myosin-light-chain kinase) inhibitor	low
methampicillin	monochlorobenzenes; tertiary alcohol; triazoles	brassinosteroid biosynthesis inhibitor	low
vibsanin b	cyclic terpene ketone; enone; tertiary alcohol; vibsane diterpenoid	plant growth retardant; plant metabolite	low
gdc-0973	aromatic amine; difluorobenzene; N-acylazetidine; organoiodine compound; piperidines; secondary amino compound; tertiary alcohol	antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
germacradienol	germacrane sesquiterpenoid; tertiary alcohol		low
azd 7545	benzamides; monochlorobenzenes; organofluorine compound; secondary carboxamide; sulfone; tertiary alcohol; tertiary carboxamide	EC 2.7.11.2 - [pyruvate dehydrogenase (acetyl-transferring)] kinase inhibitor; hypoglycemic agent	low
benzoylaconine	benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound; tetrol	phytotoxin; plant metabolite	low
berkeleydione	beta-diketone; cyclic terpene ketone; meroterpenoid; methyl ester; organic heterotetracyclic compound; terpene lactone; tertiary alcohol; tertiary alpha-hydroxy ketone	antineoplastic agent; cysteine protease inhibitor; Penicillium metabolite	low
berkeleytrione	beta-diketone; carbopolycyclic compound; cyclic terpene ketone; meroterpenoid; methyl ester; tertiary alcohol; tertiary alpha-hydroxy ketone	cysteine protease inhibitor; Penicillium metabolite	low
caribenol a	organic heterotetracyclic compound; terpene lactone; tertiary alcohol	antimalarial; antitubercular agent; metabolite	low
benzoylmesaconine	benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound; tetrol	analgesic; antiinfective agent; plant metabolite	low
papuamide b	cyclodepsipeptide; olefinic compound; secondary alcohol; tertiary alcohol	anti-HIV-1 agent; antineoplastic agent; marine metabolite	low
staphyloferrin b	oxo carboxylic acid; tertiary alcohol; tricarboxylic acid amide; tricarboxylic acid	bacterial metabolite; siderophore	low
staphyloferrin a	D-ornithine derivative; pentacarboxylic acid; tertiary alcohol; tricarboxylic acid amide	bacterial metabolite; siderophore	low
eurycomanone	cyclic ether; delta-lactone; enone; organic heteropentacyclic compound; pentol; quassinoid; secondary alcohol; secondary alpha-hydroxy ketone; tertiary alcohol	antimalarial; antineoplastic agent; metabolite	low
gardenoside	beta-D-glucoside; cyclopentapyran; enoate ester; methyl ester; monosaccharide derivative; tertiary alcohol	metabolite	low
asperfuranone	2-benzofurans; cyclic ketone; diol; polyketide; secondary alcohol; tertiary alcohol; tertiary alpha-hydroxy ketone	antineoplastic agent; fungal metabolite	low
praliciguat	aminopyrimidine; isoxazoles; monofluorobenzenes; organofluorine compound; pyrazoles; secondary amino compound; tertiary alcohol	anti-inflammatory agent; antihypertensive agent; soluble guanylate cyclase activator; vasodilator agent	low
ambrein	tertiary alcohol; triterpenoid	hypoglycemic agent; mammalian metabolite	low
enasidenib	1,3,5-triazines; aminopyridine; aromatic amine; organofluorine compound; secondary amino compound; tertiary alcohol	antineoplastic agent; EC 1.1.1.42 (isocitrate dehydrogenase) inhibitor	low
aurachin a	A-type aurachin; furoquinoline; quinoline N-oxide; tertiary alcohol	antibacterial agent; bacterial metabolite	low
cyclooctatin	carbotricyclic compound; diterpenoid; primary alcohol; secondary alcohol; tertiary alcohol	bacterial metabolite; EC 3.1.1.5 (lysophospholipase) inhibitor	low
grayanotoxin ii	tertiary alcohol		low
8-hydroxy-2-(di-n-propylamino)tetralin	phenols; tertiary amino compound; tetralins	serotonergic antagonist	low
sk&f 77434	benzazepine; catechols; tertiary amino compound	dopamine agonist	low
pd 173074	aromatic amine; biaryl; dimethoxybenzene; pyridopyrimidine; tertiary amino compound; ureas	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; fibroblast growth factor receptor antagonist	low
ethylisopropylamiloride	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker	low
amiodarone	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug	low
amodiaquine	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug	low
antazoline	aromatic amine; imidazolines; tertiary amino compound	cholinergic antagonist; H1-receptor antagonist; xenobiotic	low
azelastine	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor	low
benefin	C-nitro compound; organofluorine compound; substituted aniline; tertiary amino compound	agrochemical; herbicide	low
bupivacaine	aromatic amide; piperidinecarboxamide; tertiary amino compound		low
carbinoxamine	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antiparkinson drug; H1-receptor antagonist; muscarinic antagonist	low
chlorambucil	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent	low
chloroquine	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug	low
chlorpheniramine	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor	low
citalopram	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound		low
clofedanol	diarylmethane; tertiary amino compound	antitussive	low
diphenhydramine	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative	low
dipyridamole	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent	low
disopyramide	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug	low
1-phenyl-2-palmitoylamino-3-morpholino-1-propanol	benzyl alcohols; fatty amide; morpholines; secondary alcohol; tertiary amino compound		low
doxepin	dibenzooxepine; tertiary amino compound	antidepressant	low
profenamine	phenothiazines; tertiary amino compound	adrenergic antagonist; antidyskinesia agent; antiparkinson drug; histamine antagonist; muscarinic antagonist	low
flavoxate	carboxylic ester; flavones; piperidines; tertiary amino compound	antispasmodic drug; muscarinic antagonist; parasympatholytic	low
flurazepam	1,4-benzodiazepinone; monofluorobenzenes; organochlorine compound; tertiary amino compound	anticonvulsant; anxiolytic drug; GABAA receptor agonist; sedative	low
vanoxerine	ether; N-alkylpiperazine; organofluorine compound; tertiary amino compound	dopamine uptake inhibitor	low
gbr 12935	ether; N-alkylpiperazine; tertiary amino compound	dopamine uptake inhibitor	low
hydroxychloroquine	aminoquinoline; organochlorine compound; primary alcohol; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; dermatologic drug	low
lidocaine	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic	low
isothipendyl	aromatic amine; tertiary amino compound		low
ketotifen	cyclic ketone; olefinic compound; organic heterotricyclic compound; organosulfur heterocyclic compound; piperidines; tertiary amino compound	anti-asthmatic drug; H1-receptor antagonist	low
lofepramine	aromatic ketone; dibenzoazepine; monochlorobenzenes; tertiary amino compound	antidepressant	low
4-(dimethylamino)-n-(7-(hydroxyamino)-7-oxoheptyl)benzamide	benzamides; hydroxamic acid; secondary carboxamide; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor	low
meperidine	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	low
mesoridazine	phenothiazines; sulfoxide; tertiary amino compound	dopaminergic antagonist; first generation antipsychotic	low
methadone	benzenes; diarylmethane; ketone; tertiary amino compound		low
methiothepin	aryl sulfide; dibenzothiepine; N-alkylpiperazine; tertiary amino compound	antipsychotic agent; dopaminergic antagonist; geroprotector; serotonergic antagonist	low
metoclopramide	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic	low
minoxidil	dialkylarylamine; tertiary amino compound		low
monodansylcadaverine	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent	low
mosapramine	azaspiro compound; dibenzoazepine; organochlorine compound; tertiary amino compound		low
nefopam	benzoxazocine; tertiary amino compound		low
nicardipine	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound		low
nizatidine	1,3-thiazoles; C-nitro compound; carboxamidine; organic sulfide; tertiary amino compound	anti-ulcer drug; cholinergic drug; H2-receptor antagonist	low
orphenadrine	ether; tertiary amino compound	antidyskinesia agent; antiparkinson drug; H1-receptor antagonist; muscarinic antagonist; muscle relaxant; NMDA receptor antagonist; parasympatholytic	low
benoxinate	amino acid ester; benzoate ester; substituted aniline; tertiary amino compound	drug allergen; local anaesthetic; topical anaesthetic	low
pheniramine	pyridines; tertiary amino compound		low
pipamperone	aromatic ketone; bipiperidines; monocarboxylic acid amide; organofluorine compound; tertiary amino compound	dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist	low
piromidic acid	monocarboxylic acid; pyridopyrimidine; pyrrolidines; quinolone antibiotic; tertiary amino compound	antibacterial drug; DNA synthesis inhibitor	low
pj-34	phenanthridines; secondary carboxamide; tertiary amino compound	angiogenesis inhibitor; anti-inflammatory agent; antiatherosclerotic agent; antineoplastic agent; apoptosis inducer; cardioprotective agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; neuroprotective agent	low
procaine	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug	low
propiomazine	aromatic ketone; phenothiazines; tertiary amino compound	dopaminergic antagonist; histamine antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; sedative; serotonergic antagonist	low
psilocin	hydroxyindoles; phenols; tertiary amino compound; tryptamine alkaloid	drug metabolite; fungal metabolite; hallucinogen; human xenobiotic metabolite; serotonergic agonist	low
7-chloro-3-methyl-1-phenyl-1,2,4,5-tetrahydro-3-benzazepin-8-ol	benzazepine; organochlorine compound; tertiary amino compound	dopaminergic antagonist	low
setiptiline	tertiary amino compound; tetracyclic antidepressant	alpha-adrenergic antagonist; serotonergic antagonist	low
sibutramine	organochlorine compound; tertiary amino compound	anti-obesity agent; serotonin uptake inhibitor	low
spiperone	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist	low
tetracaine	benzoate ester; tertiary amino compound	local anaesthetic	low
tosufloxacin	1,8-naphthyridine derivative; amino acid; aminopyrrolidine; monocarboxylic acid; organofluorine compound; primary amino compound; quinolone antibiotic; tertiary amino compound		low
n,n,n',n'-tetrakis(2-pyridylmethyl)ethylenediamine	N-substituted diamine; pyridines; tertiary amino compound	apoptosis inducer; chelator; copper chelator	low
trimethobenzamide	benzamides; tertiary amino compound	antiemetic	low
trimipramine	dibenzoazepine; tertiary amino compound	antidepressant; environmental contaminant; xenobiotic	low
zotepine	dibenzothiepine; tertiary amino compound	alpha-adrenergic drug; second generation antipsychotic; serotonergic drug	low
phentolamine	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent	low
aminopyrine	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	low
tetrabenazine	benzoquinolizine; cyclic ketone; tertiary amino compound		low
acepromazine	aromatic ketone; methyl ketone; phenothiazines; tertiary amino compound	phenothiazine antipsychotic drug	low
egtazic acid	diether; tertiary amino compound; tetracarboxylic acid	chelator	low
gramine	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist	low
thenyldiamine	dialkylarylamine; tertiary amino compound		low
4-(dimethylamino)benzaldehyde	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound	low
2-diethylaminoethanol	ethanolamines; primary alcohol; tertiary amino compound		low
triethanolamine	amino alcohol; tertiary amino compound; triol	buffer; surfactant	low
4-nitrosodimethylaniline	dimethylaniline; nitroso compound; tertiary amino compound		low
triethylenediamine	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent	low
galantamine	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite	low
beta-erythroidine	delta-lactone; indole alkaloid; organic heterotetracyclic compound; tertiary amino compound	muscle relaxant; plant metabolite	low
psilocybin	organic phosphate; tertiary amino compound; tryptamine alkaloid	fungal metabolite; hallucinogen; prodrug; serotonergic agonist	low
neutral red base	aromatic amine; phenazines; primary amino compound; tertiary amino compound	acid-base indicator; dye; two-colour indicator	low
4-dimethylaminopyridine	dialkylarylamine; tertiary amino compound		low
prothipendyl	aromatic amine; tertiary amino compound		low
dymanthine	tertiary amino compound		low
azaperone	aminopyridine; aromatic ketone; monofluorobenzenes; N-alkylpiperazine; N-arylpiperazine; tertiary amino compound	antipsychotic agent; dopaminergic antagonist	low
glaucine	aporphine alkaloid; organic heterotetracyclic compound; polyether; tertiary amino compound	antibacterial agent; antineoplastic agent; antitussive; muscle relaxant; NF-kappaB inhibitor; plant metabolite; platelet aggregation inhibitor; rat metabolite	low
glyphosphine	glycine derivative; phosphonic acids; tertiary amino compound	plant growth retardant	low
c.i. solvent yellow 56	azobenzenes; substituted aniline; tertiary amino compound	dye; mutagen	low
4-dimethylaminophenol	dialkylarylamine; tertiary amino compound		low
ethyl 4-dimethylaminobenzoate	benzoate ester; ethyl ester; tertiary amino compound		low
mopidamol	dialkylarylamine; tertiary amino compound		low
thenalidine	dialkylarylamine; tertiary amino compound		low
oryzalin	aromatic amine; C-nitro compound; sulfonamide; tertiary amino compound	agrochemical; antimitotic; herbicide	low
pirimicarb	aminopyrimidine; carbamate ester; tertiary amino compound	agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic	low
dihydro-beta-erythroidine	delta-lactone; organic heterotetracyclic compound; tertiary amino compound	nicotinic antagonist	low
propamocarb	carbamate ester; carbamate fungicide; tertiary amino compound	antifungal agrochemical; environmental contaminant; xenobiotic	low
tridemorph	morpholines; tertiary amino compound	antifungal agrochemical	low
amitraz	formamidines; tertiary amino compound	acaricide; environmental contaminant; insecticide; xenobiotic	low
2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	isoquinolinol; tertiary amino compound	human metabolite; neurotoxin; rat metabolite	low
vx	organic thiophosphate; tertiary amino compound	EC 3.1.1.7 (acetylcholinesterase) inhibitor; neurotoxin	low
miglustat	piperidines; tertiary amino compound	anti-HIV agent; EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor	low
loceryl	morpholine antifungal drug; tertiary amino compound	EC 1.14.13.132 (squalene monooxygenase) inhibitor; EC 1.3.1.70 (Delta(14)-sterol reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor	low
mifepristone	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive	low
carmoxirole	indolecarboxylic acid; tertiary amino compound; tetrahydropyridine	antihypertensive agent; dopamine agonist; platelet aggregation inhibitor	low
naxagolide	organic heterotricyclic compound; phenols; tertiary amino compound	anticonvulsant; antiparkinson drug; dopamine agonist	low
temafloxacin	amino acid; monocarboxylic acid; N-arylpiperazine; organofluorine compound; quinolone antibiotic; quinolone; secondary amino compound; tertiary amino compound		low
tiagabine	beta-amino acid; piperidinemonocarboxylic acid; tertiary amino compound; thiophenes	anticonvulsant; GABA reuptake inhibitor	low
eliprodil	monochlorobenzenes; monofluorobenzenes; piperidines; secondary alcohol; tertiary amino compound		low
carfentanil	methyl ester; piperidines; tertiary amino compound; tertiary carboxamide	mu-opioid receptor agonist; opioid analgesic; tranquilizing drug	low
acridine orange	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye	low
tenocyclidine	piperidines; tertiary amino compound; thiophenes	central nervous system stimulant; hallucinogen; neuroprotective agent; NMDA receptor antagonist	low
nelfinavir	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor	low
plerixafor	azacycloalkane; azamacrocycle; benzenes; crown amine; secondary amino compound; tertiary amino compound	anti-HIV agent; antineoplastic agent; C-X-C chemokine receptor type 4 antagonist; immunological adjuvant	low
nile red	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye	low
cephalotaxine	benzazepine alkaloid fundamental parent; benzazepine alkaloid; cyclic acetal; enol ether; organic heteropentacyclic compound; secondary alcohol; tertiary amino compound		low
4-(diethylamino)benzaldehyde	aromatic amine; benzaldehydes; tertiary amino compound	EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor	low
propildazine	dialkylarylamine; tertiary amino compound		low
tubulosine	beta-carbolines; isoquinoline alkaloid; isoquinolines; phenols; secondary amino compound; tertiary amino compound		low
voacamine	alkaloid ester; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; plant metabolite	low
rivastigmine	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent	low
dimethylformamide-dimethylacetal	acetal; tertiary amino compound	chromatographic reagent	low
n-(3-(dimethylamino)propyl)methacrylamide	tertiary amino compound		low
n,n-diisopropylethylamine	tertiary amino compound		low
spiroxamine	dioxolane; spiroketal; tertiary amino compound	antifungal agrochemical; environmental contaminant; sterol biosynthesis inhibitor; xenobiotic	low
mor-14	hydroxypiperidine; piperidine alkaloid; tertiary amino compound	anti-HIV agent; cardioprotective agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite	low
ecgonine methyl ester	methyl ester; tertiary amino compound; tropane alkaloid	analgesic; central nervous system depressant; metabolite; mouse metabolite; opioid analgesic; peripheral nervous system drug	low
ecteinascidin 743	acetate ester; azaspiro compound; bridged compound; hemiaminal; isoquinoline alkaloid; lactone; organic heteropolycyclic compound; organic sulfide; oxaspiro compound; polyphenol; tertiary amino compound	alkylating agent; angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; marine metabolite	low
aporphine	aporphine alkaloid; isoquinoline alkaloid fundamental parent; tertiary amino compound		low
efonidipine	C-nitro compound; carboxylic ester; dihydropyridine; tertiary amino compound		low
n-(4-(7-diethylamino-4-methylcoumarin-3-yl)phenyl)maleimide	benzenes; coumarins; maleimides; tertiary amino compound	fluorescent dye	low
lofentanil	methyl ester; piperidines; tertiary amino compound; tertiary carboxamide	mu-opioid receptor agonist; opioid analgesic	low
1-(1-(2-benzo(b)thienyl)cyclohexyl)piperidine	1-benzothiophenes; piperidines; tertiary amino compound	dopamine uptake inhibitor	low
desvenlafaxine	cyclohexanols; phenols; tertiary amino compound	antidepressant; drug metabolite; marine xenobiotic metabolite	low
ulipristal acetate	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; steroid ester; tertiary amino compound	contraceptive drug; progesterone receptor modulator; progestin	low
sr 57227a	dialkylarylamine; tertiary amino compound		low
2,8-dinitroimipramine	C-nitro compound; dibenzoazepine; tertiary amino compound		low
sk&f 83959	benzazepine; catechols; organochlorine compound; tertiary amino compound	dopamine agonist	low
5,6-didehydrosparteine	organic heterotetracyclic compound; quinolizidine alkaloid; tertiary amino compound	human xenobiotic metabolite	low
stephenanthrine	cyclic acetal; organic heterotetracyclic compound; tertiary amino compound		low
hydromethylthionine	aromatic amine; phenothiazines; tertiary amino compound	bacterial xenobiotic metabolite; fluorochrome; mouse metabolite; rat metabolite	low
nbi 27914	dialkylarylamine; tertiary amino compound		low
top 53	furonaphthodioxole; gamma-lactone; organic heterotetracyclic compound; phenols; tertiary amino compound	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
antalarmin	pyrrolopyrimidine; tertiary amino compound	corticotropin-releasing factor receptor antagonist	low
alpha-putrescinylthymine	N-substituted putrescine; pyrimidine nucleobase; pyrimidone; secondary amino compound; tertiary amino compound		low
2-(4-morpholinoanilino)-6-cyclohexylaminopurine	morpholines; purines; secondary amino compound; tertiary amino compound	adenosine A3 receptor antagonist; antineoplastic agent; Aurora kinase inhibitor; cell dedifferentiation agent	low
l 778,123	imidazoles; monochlorobenzenes; nitrile; piperazinone; tertiary amino compound	antineoplastic agent; EC 2.5.1.58 (protein farnesyltransferase) inhibitor; EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor	low
azaleucine	alanine derivative; leucine derivative; non-proteinogenic alpha-amino acid; tertiary amino compound		low
nsc 23766	aminopyrimidine; aminoquinoline; primary amino compound; secondary amino compound; tertiary amino compound	antiviral agent; apoptosis inducer; EC 3.6.5.2 (small monomeric GTPase) inhibitor; muscarinic antagonist	low
gant 61	aminal; dialkylarylamine; pyridines; substituted aniline; tertiary amino compound	antineoplastic agent; apoptosis inducer; glioma-associated oncogene inhibitor; Hedgehog signaling pathway inhibitor	low
conessine	steroid alkaloid; tertiary amino compound	antibacterial agent; antimalarial; H3-receptor antagonist; plant metabolite	low
rocuronium	3alpha-hydroxy steroid; acetate ester; androstane; morpholines; quaternary ammonium ion; tertiary amino compound	drug allergen; muscle relaxant; neuromuscular agent	low
oxyacanthine	bisbenzylisoquinoline alkaloid; isoquinolines; macrocycle; phenols; tertiary amino compound		low
ergonovine	ergot alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound; primary alcohol; secondary amino compound; tertiary amino compound	diagnostic agent; fungal metabolite; oxytocic; toxin	low
colforsin daropate	acetate ester; carboxylic ester; cyclic ketone; diol; organic heterotricyclic compound; tertiary amino compound	adenylate cyclase agonist; antihypertensive agent; cardiotonic drug; vasodilator agent	low
cocaine	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic	low
afimoxifene	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite	low
n-nonyl-1-deoxynojirimycin	hydroxypiperidine; tertiary amino compound	antiviral agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.2.1.45 (glucosylceramidase) inhibitor	low
3-(4-chlorophenyl)-6-(1-pyrrolidinyl)-1,2,4,5-tetrazine	dialkylarylamine; tertiary amino compound		low
n-methylproline	L-alpha-amino acid zwitterion; L-proline derivative; tertiary amino compound	human metabolite; plant metabolite	low
5-[3-(dimethylamino)phenyl]-N-methyl-1,3,4-thiadiazol-2-amine	dialkylarylamine; tertiary amino compound		low
N4-(2-furanylmethyl)-N2-(3-methylphenyl)-6-(4-morpholinyl)-1,3,5-triazine-2,4-diamine	dialkylarylamine; tertiary amino compound		low
7-(2-methyl-2,3-dihydroindol-1-yl)-3-(phenylmethyl)triazolo[4,5-d]pyrimidine	aromatic amine; tertiary amino compound		low
tiamulin	carbotricyclic compound; carboxylic ester; cyclic ketone; organic sulfide; secondary alcohol; semisynthetic derivative; tertiary amino compound; tetracyclic diterpenoid	antibacterial drug	low
2-amino-4-(cyanomethyl)-6-(N-methylanilino)pyridine-3,5-dicarbonitrile	aromatic amine; tertiary amino compound		low
N-[4-(diethylamino)phenyl]-N'-phenylurea	dialkylarylamine; tertiary amino compound		low
4-bromo-2-phenyl-5-(1-piperidinyl)-3-pyridazinone	dialkylarylamine; tertiary amino compound		low
N4,N4-dimethyl-N1-(4-nitro-1,1-dioxo-2,5-dihydrothiophen-3-yl)benzene-1,4-diamine	dialkylarylamine; tertiary amino compound		low
N-methyl-2-(4-methylphenyl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine	piperidines; quinazolines; tertiary amino compound; toluenes		low
4-(2,3-dihydro-1H-indol-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine	aromatic amine; tertiary amino compound		low
4-[methyl-(4-thiophen-2-yl-2-thiazolyl)amino]phenol	aromatic amine; tertiary amino compound		low
4-[[4-bromo-5-(4-morpholinyl)-2-furanyl]methylideneamino]phenol	dialkylarylamine; tertiary amino compound		low
4-chloro-5-(dimethylamino)-2-(4-methylphenyl)-3-pyridazinone	dialkylarylamine; tertiary amino compound		low
N,N-dibutyl-2-(pyridin-4-yl)quinazolin-4-amine	pyridines; quinazolines; tertiary amino compound		low
2-[5-(4-chlorophenyl)-1,3,5-dithiazinan-2-ylidene]-2-diethoxyphosphorylacetonitrile	dialkylarylamine; tertiary amino compound		low
2-[[4-(4-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	dialkylarylamine; tertiary amino compound		low
2-(2,4-dioxo-1H-pyrimidin-6-yl)-N-[2-(4-morpholinyl)ethyl]acetamide	morpholines; pyrimidone; secondary carboxamide; tertiary amino compound		low
2-chloro-N-[4-(N-propan-2-ylanilino)phenyl]acetamide	aromatic amine; tertiary amino compound		low
tamoxifen	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator	low
3-(1-pyrrolidinyl)-5-(trifluoromethyl)pyridine-2-carbothioamide	dialkylarylamine; tertiary amino compound		low
2-[[2-oxo-2-[4-[5-(trifluoromethyl)-2-pyridinyl]-1,4-diazepan-1-yl]ethyl]thio]acetic acid	dialkylarylamine; tertiary amino compound		low
3-(4-ethyl-1-piperazinyl)-5-methylpyridazino[3,4-b][1,4]benzoxazine	aromatic amine; tertiary amino compound		low
4-(5,6-diphenyl-1,2,4-triazin-3-yl)morpholine	dialkylarylamine; tertiary amino compound		low
3-[[5,5-dimethyl-3-(4-morpholinyl)-1-cyclohex-2-enylidene]amino]-N,N-dimethylaniline	dialkylarylamine; tertiary amino compound		low
ranitidine	C-nitro compound; furans; organic sulfide; tertiary amino compound	anti-ulcer drug; drug allergen; environmental contaminant; H2-receptor antagonist; xenobiotic	low
stenusin	piperidine alkaloid; tertiary amino compound		low
dasatinib	1,3-thiazoles; aminopyrimidine; monocarboxylic acid amide; N-(2-hydroxyethyl)piperazine; N-arylpiperazine; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor	low
noribogaine	monoterpenoid indole alkaloid; organic heteropentacyclic compound; secondary amino compound; tertiary amino compound	kappa-opioid receptor agonist; NMDA receptor antagonist; psychotropic drug; serotonin uptake inhibitor	low
2-[[4-(3-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	dialkylarylamine; tertiary amino compound		low
2-(N-ethylanilino)-4-thieno[3,2-d][1,3]thiazinone	aromatic amine; tertiary amino compound		low
N-[3-(N-ethylanilino)propyl]-2,4-dimethyl-6-oxo-3-pyrancarboxamide	dialkylarylamine; tertiary amino compound		low
5-(1-azepanyl)-1,3,4-thiadiazol-2-amine	dialkylarylamine; tertiary amino compound		low
3-(5-chloro-2-methylphenyl)-6-(2,6-dimethyl-4-morpholinyl)-1H-pyrimidine-2,4-dione	dialkylarylamine; tertiary amino compound		low
N4-ethyl-N6,1,2-trimethyl-N4-phenylpyrimidin-1-ium-4,6-diamine	aromatic amine; tertiary amino compound		low
clopidogrel carboxylic acid	monocarboxylic acid; monochlorobenzenes; tertiary amino compound; thienopyridine	drug metabolite; marine xenobiotic metabolite	low
LY-310762	aromatic ketone; monofluorobenzenes; oxindoles; piperidines; tertiary amino compound	receptor modulator; serotonergic antagonist	low
ly 367265	dihydropyridine; fluoroindole; tertiary amino compound; thiadiazoloquinoline	antidepressant; geroprotector; serotonergic antagonist; serotonin uptake inhibitor	low
N-(1-benzylpiperidin-4-yl)-2-(pyridin-3-yl)quinazolin-4-amine	aromatic amine; piperidines; pyridines; quinazolines; secondary amino compound; tertiary amino compound		low
3-[4-(dimethylamino)phenyl]-N-methyl-5-(4-methylphenyl)-3,4-dihydropyrazole-2-carbothioamide	dialkylarylamine; tertiary amino compound		low
mycophenolate mofetil	carboxylic ester; ether; gamma-lactone; phenols; tertiary amino compound	anticoronaviral agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; immunosuppressive agent; prodrug	low
cassaine	enoate ester; organic hydroxy compound; tertiary amino compound; tricyclic diterpenoid	antihypertensive agent; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; local anaesthetic; plant metabolite; poison	low
acetylspiramycin	acetate ester; aldehyde; disaccharide derivative; ether; macrolide; tertiary amino compound	antibacterial drug; antimicrobial agent; bacterial metabolite	low
n,n-dimethylsphingenine	aminodiol; sphingoid; tertiary amino compound	EC 2.7.1.91 (sphingosine kinase) inhibitor; metabolite	low
alvocidib	dihydroxyflavone; hydroxypiperidine; monochlorobenzenes; tertiary amino compound	antineoplastic agent; antirheumatic drug; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor	low
17-(dimethylaminoethylamino)-17-demethoxygeldanamycin	1,4-benzoquinones; ansamycin; carbamate ester; secondary amino compound; tertiary amino compound	Hsp90 inhibitor	low
morphine	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic	low
kn 93	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector	low
su 11652	olefinic compound; organochlorine compound; oxindoles; pyrrolecarboxamide; tertiary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor	low
palbociclib	aminopyridine; aromatic ketone; cyclopentanes; piperidines; pyridopyrimidine; secondary amino compound; tertiary amino compound	antineoplastic agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor	low
catharanthine	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound		low
oripavine	ether; morphinane alkaloid; organic heteropentacyclic compound; organic hydroxy compound; tertiary amino compound	bacterial xenobiotic metabolite; opioid analgesic	low
cinanserin	aryl sulfide; cinnamamides; secondary carboxamide; tertiary amino compound	anticoronaviral agent; antiviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor	low
DPI2	benzenes; morpholines; secondary carboxamide; tertiary amino compound; thiazolidinone	ferroptosis inducer	low
7-hydroxy-2-(n-n-propyl-n-(3-iodo-2'-propenyl)-amino)tetralin	organoiodine compound; phenols; tertiary amino compound; tetralins	dopamine agonist	low
sdz eaa 494	monocarboxylic acid; olefinic compound; phosphonic acids; piperazinecarboxylic acid; tertiary amino compound	anticonvulsant; neuroprotective agent; NMDA receptor antagonist	low
demycarosylturimycin h	aldehyde; disaccharide derivative; ether; macrolide; tertiary amino compound	antibacterial drug; antimicrobial agent; bacterial metabolite	low
ro 25-6981	benzenes; phenols; piperidines; secondary alcohol; tertiary amino compound	anticonvulsant; antidepressant; neuroprotective agent; NMDA receptor antagonist	low
eaa-090	dialkylarylamine; tertiary amino compound		low
prasugrel	acetate ester; cyclopropanes; ketone; monofluorobenzenes; tertiary amino compound; thienopyridine		low
muromonab-cd3	alkaloid; macrocycle; organic heteropentacyclic compound; organonitrogen heterocyclic compound; oxacycle; tertiary amino compound	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; IP3 receptor antagonist; marine metabolite	low
px-866	acetate ester; delta-lactone; organic heterotetracyclic compound; tertiary amino compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor	low
pi103	aromatic amine; morpholines; organic heterotricyclic compound; phenols; tertiary amino compound	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor	low
selexipag	aromatic amine; ether; monocarboxylic acid amide; N-sulfonylcarboxamide; pyrazines; tertiary amino compound	orphan drug; platelet aggregation inhibitor; prodrug; prostacyclin receptor agonist; vasodilator agent	low
tofacitinib	N-acylpiperidine; nitrile; pyrrolopyrimidine; tertiary amino compound	antirheumatic drug; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
mre 269	aromatic amine; ether; monocarboxylic acid; pyrazines; sulfonamide; tertiary amino compound	drug metabolite; orphan drug; platelet aggregation inhibitor; prostacyclin receptor agonist; vasodilator agent	low
NNC 55-0396 (free base)	benzimidazoles; cyclopropanecarboxylate ester; organofluorine compound; tertiary amino compound; tetralins	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; neuroprotective agent; potassium channel blocker; T-type calcium channel blocker	low
pateamine a	1,3-thiazoles; macrodiolide; olefinic compound; primary amino compound; tertiary amino compound	antineoplastic agent; antiviral agent; eukaryotic initiation factor 4F inhibitor; marine metabolite	low
edoxaban	chloropyridine; monocarboxylic acid amide; tertiary amino compound; thiazolopyridine	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor; platelet aggregation inhibitor	low
akuammicine	methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	plant metabolite	low
abt-737	aromatic amine; aryl sulfide; biphenyls; C-nitro compound; monochlorobenzenes; N-arylpiperazine; N-sulfonylcarboxamide; secondary amino compound; tertiary amino compound	anti-allergic agent; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor	low
azd 1152	anilide; monoalkyl phosphate; monofluorobenzenes; pyrazoles; quinazolines; secondary amino compound; secondary carboxamide; tertiary amino compound	antineoplastic agent; Aurora kinase inhibitor; prodrug	low
pf 00299804	enamide; monochlorobenzenes; monofluorobenzenes; piperidines; quinazolines; secondary amino compound; secondary carboxamide; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist	low
finafloxacin	cyclopropanes; monocarboxylic acid; nitrile; organofluorine compound; quinolone; secondary amino compound; tertiary amino compound	antibacterial drug; antimicrobial agent	low
sarpagine	indole alkaloid; phenols; primary alcohol; secondary amino compound; tertiary amino compound		low
5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-methyl)-piperidinyl)-4h-1-benzopyran-4-one	alkaloid; chromones; hydroxypiperidine; resorcinols; tertiary amino compound	anti-inflammatory agent; anti-ulcer drug; anticholesteremic drug; antileishmanial agent; antineoplastic agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; fungal metabolite; plant metabolite	low
azd 1152-hqpa	anilide; monofluorobenzenes; primary alcohol; pyrazoles; quinazolines; secondary amino compound; secondary carboxamide; tertiary amino compound	antineoplastic agent; Aurora kinase inhibitor	low
ku 0063794	benzyl alcohols; monomethoxybenzene; morpholines; pyridopyrimidine; tertiary amino compound	antineoplastic agent; mTOR inhibitor	low
flupyradifurone	butenolide; enamine; monochloropyridine; organofluorine insecticide; tertiary amino compound	insecticide; nicotinic acetylcholine receptor agonist	low
alcaftadine	aldehyde; imidazobenzazepine; piperidines; tertiary amino compound	anti-allergic agent; H1-receptor antagonist	low
deoxyaconitine	acetate ester; benzoate ester; bridged compound; diol; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary amino compound	plant metabolite	low
2-[[4-(4-methylanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	dialkylarylamine; tertiary amino compound		low
2-[[4-(2-chloroanilino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]ethanol	dialkylarylamine; tertiary amino compound		low
2-[[4-(2-hydroxyethylamino)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]amino]phenol	dialkylarylamine; tertiary amino compound		low
vindolinine	methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	plant metabolite	low
tenovin-6	monocarboxylic acid amide; tertiary amino compound; thioureas	antineoplastic agent; p53 activator; Sir2 inhibitor	low
sch772984	biaryl; indazoles; N-acylpiperazine; N-alkylpyrrolidine; N-arylpiperazine; pyridines; pyrimidines; pyrrolidinecarboxamide; secondary carboxamide; tertiary amino compound; tertiary carboxamide	analgesic; antineoplastic agent; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
navitoclax	aryl sulfide; monochlorobenzenes; morpholines; N-sulfonylcarboxamide; organofluorine compound; piperazines; secondary amino compound; sulfone; tertiary amino compound	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor	low
n-(cyanomethyl)-4-(2-((4-(4-morpholinyl)phenyl)amino)-4-pyrimidinyl)benzamide	aminopyrimidine; benzamides; morpholines; nitrile; secondary amino compound; tertiary amino compound	anti-anaemic agent; antineoplastic agent; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
(5-(2,4-bis((3s)-3-methylmorpholin-4-yl)pyrido(2,3-d)pyrimidin-7-yl)-2-methoxyphenyl)methanol	benzyl alcohols; morpholines; pyridopyrimidine; tertiary amino compound	antineoplastic agent; apoptosis inducer; mTOR inhibitor	low
N-[[(2R,3S)-10-(dimethylamino)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-N-methylmethanesulfonamide	dialkylarylamine; tertiary amino compound		low
(2S,3R)-8-(dimethylamino)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl(pyridin-4-ylmethyl)amino]methyl]-3,4-dihydro-2H-1,5-benzoxazocin-6-one	dialkylarylamine; tertiary amino compound		low
N-[[(2S,3S)-10-(dimethylamino)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-N,3,5-trimethyl-4-isoxazolesulfonamide	dialkylarylamine; tertiary amino compound		low
(2S,3S)-10-(dimethylamino)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-2-[[methyl(pyridin-4-ylmethyl)amino]methyl]-3,4-dihydro-2H-1,5-benzoxazocin-6-one	dialkylarylamine; tertiary amino compound		low
3-cyclohexyl-1-[[(2S,3S)-10-(dimethylamino)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-1-methylurea	dialkylarylamine; tertiary amino compound		low
1-[[(2S,3S)-10-(dimethylamino)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-6-oxo-3,4-dihydro-2H-1,5-benzoxazocin-2-yl]methyl]-1-methyl-3-propan-2-ylurea	dialkylarylamine; tertiary amino compound		low
cblc137	aromatic ketone; carbazoles; methyl ketone; secondary amino compound; tertiary amino compound	antineoplastic agent; apoptosis inducer; NF-kappaB inhibitor; p53 activator	low
1-[3-[(5-bromo-2-pyridinyl)-butylamino]propyl]-3-[3-(1H-imidazol-5-yl)propyl]thiourea	dialkylarylamine; tertiary amino compound		low
tubastatin a	hydroxamic acid; pyridoindole; tertiary amino compound	EC 3.5.1.98 (histone deacetylase) inhibitor	low
pracinostat	benzimidazole; hydroxamic acid; olefinic compound; tertiary amino compound	antimalarial; antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor	low
delgocitinib	azaspiro compound; N-acylazetidine; nitrile; pyrrolopyrimidine; tertiary amino compound; tertiary carboxamide	anti-inflammatory drug; antipsoriatic; antiseborrheic; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
pf 956980	N-acylpiperidine; N-acylpyrrolidine; pyrrolopyrimidine; tertiary amino compound	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor	low
AZD3463	aminopiperidine; aminopyrimidine; indoles; monomethoxybenzene; organochlorine compound; secondary amino compound; tertiary amino compound	antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	low
gsk2879552	benzenes; benzoic acids; cyclopropanes; monocarboxylic acid; piperidines; secondary amino compound; tertiary amino compound	antineoplastic agent; EC 1.14.99.66 (lysine-specific histone demethylase 1A) inhibitor	low
osimertinib	acrylamides; aminopyrimidine; biaryl; indoles; monomethoxybenzene; secondary amino compound; secondary carboxamide; substituted aniline; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist	low
as 1842856	organofluorine compound; primary amino compound; quinolinemonocarboxylic acid; quinolone; secondary amino compound; tertiary amino compound	anti-obesity agent; antineoplastic agent; apoptosis inducer; autophagy inhibitor; forkhead box protein O1 inhibitor; hypoglycemic agent	low
BDA-366	anthraquinone; epoxide; secondary alcohol; secondary amino compound; tertiary amino compound	antineoplastic agent; apoptosis inducer	low
5-(2-chloro-6-fluorobenzyl)-6-methyl-2-morpholinopyrimidin-4-ol	dialkylarylamine; tertiary amino compound		low
2-hydroxy-3-(5-((morpholin-4-yl)methyl)pyridin-2-yl)-1h-indole-5-carbonitrile	hydroxyindoles; morpholines; nitrile; pyridines; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; tau aggregation inhibitor	low
sotorasib	acrylamides; methylpyridines; monofluorobenzenes; N-acylpiperazine; phenols; pyridopyrimidine; tertiary amino compound; tertiary carboxamide	antineoplastic agent	low

Substance	Classes	Roles	Relationship Strength
pyrazinamide	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug	low
pyrazinoic acid	pyrazinecarboxylic acid	antitubercular agent; drug metabolite	low
isoniazid	carbohydrazide	antitubercular agent; drug allergen	low
lomefloxacin	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent	low
aminosalicylic acid	aminobenzoic acid; phenols	antitubercular agent	low
cycloserine	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist	low
azomycin	C-nitro compound; imidazoles	antitubercular agent	low
hentriacontane	long-chain alkane	antitubercular agent	low
ethambutol hydrochloride	hydrochloride	antitubercular agent	low
ethambutol	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic	low
lomefloxacin hydrochloride	hydrochloride	antimicrobial agent; antitubercular agent; photosensitizing agent	low
ethionamide	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug	low
rifamycin sv	acetate ester; cyclic ketal; lactam; macrocycle; organic heterotetracyclic compound; polyphenol; rifamycins	antimicrobial agent; antitubercular agent; bacterial metabolite	low
caribenol a	organic heterotetracyclic compound; terpene lactone; tertiary alcohol	antimalarial; antitubercular agent; metabolite	low
s-ethylcysteine	S-alkyl-L-cysteine zwitterion; S-alkyl-L-cysteine	antitubercular agent	low
viomycin	heterodetic cyclic peptide; peptide antibiotic	antitubercular agent	low
rifampin	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor	low
rifapentine	N-alkylpiperazine; N-iminopiperazine; rifamycins	antitubercular agent; leprostatic drug	low
carbonyl cyanide p-trifluoromethoxyphenylhydrazone	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore	low
dicyclohexylcarbodiimide	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent	low

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
caribenol a	0	organic heterotetracyclic compound; terpene lactone; tertiary alcohol	antimalarial; antitubercular agent; metabolite	0	0		low	0	0	0	0	0	0
carbonyl cyanide p-trifluoromethoxyphenylhydrazone	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore	0	0		low	0	0	0	0	0	0

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	2000's	2010's	post-2020
catechol	1	catechols	allelochemical; genotoxin; plant metabolite	2019	2019	5.0	low	0	0	1	0
hydroquinone	1	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent	2019	2019	5.0	low	0	0	1	0
pyrazinamide	2	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug	2007	2013	14.0	low	0	1	1	0
catechin	1	hydroxyflavan		2019	2019	5.0	low	0	0	1	0
amantadine	1	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic	2019	2019	5.0	low	0	0	1	0
arotinolol	1	aromatic amide; thiophenes		2022	2022	2.0	low	0	0	0	1
azelastine	1	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor	2020	2020	4.0	low	0	0	1	0
verapamil	1	aromatic ether; nitrile; polyether; tertiary amino compound		2022	2022	2.0	low	0	0	0	1
clofazimine	6	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug	2013	2022	6.0	low	0	0	5	1
isoniazid	26	carbohydrazide	antitubercular agent; drug allergen	2007	2022	8.2	low	1	2	20	4
manidipine	1	diarylmethane		2020	2020	4.0	low	0	0	1	0
mefloquine hydrochloride	1	organofluorine compound; piperidines; quinolines; secondary alcohol		2013	2013	11.0	low	0	0	1	0
metronidazole	2	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic	2015	2017	8.0	low	0	0	2	0
ofloxacin	1	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline		2019	2019	5.0	low	0	0	1	0
aminosalicylic acid	1	aminobenzoic acid; phenols	antitubercular agent	2016	2016	8.0	low	0	0	1	0
periciazine	1	hydroxypiperidine; nitrile; phenothiazines	adrenergic antagonist; first generation antipsychotic; sedative	2020	2020	4.0	low	0	0	1	0
ono 1078	1	chromones		2022	2022	2.0	low	0	0	0	1
resorcinol	1	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser	2019	2019	5.0	low	0	0	1	0
rimantadine	1	alkylamine		2019	2019	5.0	low	0	0	1	0
gatifloxacin	2	N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antiinfective agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	2009	2012	13.5	low	0	1	1	0
thioridazine	1	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist	2022	2022	2.0	low	0	0	0	1
triclosan	2	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic	2014	2014	10.0	low	0	0	2	0
chloramphenicol	1	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor	2014	2014	10.0	low	0	0	1	0
kanamycin a	1	kanamycins	bacterial metabolite	2022	2022	2.0	low	0	0	0	1
cycloserine	1	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist	2022	2022	2.0	low	0	0	0	1
hesperidin	1	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen	2019	2019	5.0	low	0	0	1	0
dicyclohexylcarbodiimide	1	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent	2015	2015	9.0	low	0	0	1	0
2-nitrofluorene	1	nitroarene	carcinogenic agent; mutagen	2019	2019	5.0	low	0	0	1	0
2-anthramine	1	anthracenamine		2019	2019	5.0	low	0	0	1	0
ethambutol	4	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic	2009	2019	10.0	low	0	1	3	0
antimycin a	1	benzamides; formamides; macrodiolide; phenols	antifungal agent; mitochondrial respiratory-chain inhibitor; piscicide	2016	2016	8.0	low	0	0	1	0
streptomycin	2	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor	2017	2019	6.0	low	0	0	2	0
camptothecin	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite	2014	2014	10.0	low	0	0	1	0
sodium azide	1	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen	2019	2019	5.0	low	0	0	1	0
amoxicillin	1	penicillin allergen; penicillin	antibacterial drug	2014	2014	10.0	low	0	0	1	0
amikacin	2	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin	2009	2019	10.0	low	0	1	1	0
mefloquine	1	[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol	antimalarial	2022	2022	2.0	low	0	0	0	1
nitazoxanide	1	benzamides; carboxylic ester		2022	2022	2.0	low	0	0	0	1
idarubicin	1	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative		2020	2020	4.0	low	0	0	1	0
sulfometuron methyl	1	benzoate ester; N-sulfonylurea; pyrimidines	EC 2.2.1.6 (acetolactate synthase) inhibitor; herbicide	2005	2005	19.0	low	0	1	0	0
cabergoline	1	N-acylurea	antineoplastic agent; antiparkinson drug; dopamine agonist	2020	2020	4.0	low	0	0	1	0
dup 105	1			2012	2012	12.0	low	0	0	1	0
sparfloxacin	1	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone		2014	2014	10.0	low	0	0	1	0
nelfinavir	1	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor	2020	2020	4.0	low	0	0	1	0
epigallocatechin gallate	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite	2019	2019	5.0	low	0	0	1	0
lercanidipine	1	diarylmethane		2020	2020	4.0	low	0	0	1	0
fropenem	1	faropenem		2022	2022	2.0	low	0	0	0	1
4(5)-phenylimidazole	1			2020	2020	4.0	low	0	0	1	0
uk 68798	1	aromatic ether; sulfonamide; tertiary amino compound	anti-arrhythmia drug; potassium channel blocker	2020	2020	4.0	low	0	0	1	0
ljc 10627	1	carbapenems; organic sulfide; pyrazolotriazole	antibacterial drug	2022	2022	2.0	low	0	0	0	1
talampicillin	1	penicillanic acid ester	prodrug	2020	2020	4.0	low	0	0	1	0
gentamicin c1a	1	gentamycin C		2019	2019	5.0	low	0	0	1	0
5-nitro-1,10-phenanthroline	1			2022	2022	2.0	low	0	0	0	1
2-(salicylideneamino)phenol	1			2019	2019	5.0	medium	0	0	1	0
clarithromycin	1	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic	2009	2009	15.0	low	0	1	0	0
lopinavir	1	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor	2020	2020	4.0	low	0	0	1	0
efonidipine	1	C-nitro compound; carboxylic ester; dihydropyridine; tertiary amino compound		2020	2020	4.0	low	0	0	1	0
2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile	1			2021	2021	3.0	low	0	0	0	1
cd 437	1	adamantanes; monocarboxylic acid; naphthoic acid; phenols	apoptosis inducer; retinoic acid receptor gamma agonist	2019	2019	5.0	low	0	0	1	0
levofloxacin	1	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor	2019	2019	5.0	low	0	0	1	0
moxifloxacin	11	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug	2007	2022	9.4	low	0	2	7	2
naproxen	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	2019	2019	5.0	low	0	0	1	0
lapatinib	1	furans; organochlorine compound; organofluorine compound; quinazolines	antineoplastic agent; tyrosine kinase inhibitor	2020	2020	4.0	low	0	0	1	0
azd2563	2			2012	2014	11.0	low	0	0	2	0
nu 6027	1			2022	2022	2.0	low	0	0	0	1
meropenem	1	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen	2022	2022	2.0	low	0	0	0	1
linezolid	8	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor	2012	2022	7.2	low	0	0	7	1
doxorubicin hydrochloride	1	anthracycline		2016	2016	8.0	low	0	0	1	0
resveratrol	1	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger	2019	2019	5.0	low	0	0	1	0
pa 824	12			2005	2022	9.2	low	0	2	8	2
bm 212	2			2005	2020	11.5	low	0	1	1	0
u 100480	6			2005	2022	8.2	medium	0	1	3	2
3,3',4,5'-tetrahydroxystilbene	1	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor	2019	2019	5.0	low	0	0	1	0
curcumin	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger	2019	2019	5.0	low	0	0	1	0
fatostatin	1	thiazoles		2014	2014	10.0	low	0	0	1	0
ethionamide	2	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug	2014	2022	6.0	low	0	0	1	1
silybin	1			2019	2019	5.0	low	0	0	1	0
sq 109	6			2009	2022	7.5	medium	0	1	3	2
quercetin	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger	2019	2019	5.0	low	0	0	1	0
apigenin	1	trihydroxyflavone	antineoplastic agent; metabolite	2019	2019	5.0	low	0	0	1	0
luteolin	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist	2019	2019	5.0	low	0	0	1	0
quercetin 3-o-glucopyranoside	1	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite	2019	2019	5.0	low	0	0	1	0
rutin	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite	2019	2019	5.0	low	0	0	1	0
kaempferol	1	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite	2019	2019	5.0	low	0	0	1	0
genistein	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor	2019	2019	5.0	low	0	0	1	0
baicalein	1	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger	2019	2019	5.0	low	0	0	1	0
chrysin	1	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite	2019	2019	5.0	low	0	0	1	0
diosmin	1	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant	2019	2019	5.0	low	0	0	1	0
galangin	1	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite	2019	2019	5.0	low	0	0	1	0
morin	1	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent	2019	2019	5.0	low	0	0	1	0
daidzein	1	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite	2019	2019	5.0	low	0	0	1	0
indinavir sulfate	1	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor	2020	2020	4.0	low	0	0	1	0
citreoviridin	1	2-pyranones		2019	2019	5.0	low	0	0	1	0
piroxicam cinnamate	1	cinnamate ester		2020	2020	4.0	low	0	0	1	0
sri 286	1			2020	2020	4.0	low	0	0	1	0
opc-67683	5	piperidines		2009	2022	7.6	low	0	1	3	1
sri 224	1			2020	2020	4.0	medium	0	0	1	0
thioacetazone	1			2020	2020	4.0	low	0	0	1	0
tebipenem	1			2022	2022	2.0	low	0	0	0	1
dup 721	1			2012	2012	12.0	medium	0	0	1	0
perampanel	1	bipyridines; nitrile; pyridone	AMPA receptor antagonist; anticonvulsant	2020	2020	4.0	low	0	0	1	0
n-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-(2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexan-2-carboxamide	1	tripeptide; ureas	antiviral drug; hepatitis C protease inhibitor; peptidomimetic	2020	2020	4.0	low	0	0	1	0
forapin	1	peptidyl amide; polypeptide	animal metabolite; antineoplastic agent; apoptosis inducer; EC 2.7.11.13 (protein kinase C) inhibitor; hepatoprotective agent; neuroprotective agent; venom	2019	2019	5.0	low	0	0	1	0
btz 043	8			2012	2022	6.0	high	0	0	5	3
btz 043	1			2014	2014	10.0	low	0	0	1	0
novobiocin	1	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent	2014	2014	10.0	low	0	0	1	0
tipranavir	1	sulfonamide	antiviral drug; HIV protease inhibitor	2020	2020	4.0	low	0	0	1	0
lymecycline	1			2022	2022	2.0	low	0	0	0	1
pbtz169	5			2014	2022	4.4	medium	0	0	2	3
ceritinib	1	aminopyrimidine; aromatic ether; organochlorine compound; piperidines; secondary amino compound; sulfone	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	2022	2022	2.0	low	0	0	0	1
4,6-dichloro-n-(4,4-dimethylcyclohexyl)-1h-indole-2-carboxamide	1			2022	2022	2.0	medium	0	0	0	1
s 8932	1	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug	2020	2020	4.0	low	0	0	1	0
rifampin	21	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor	2007	2022	9.1	low	1	4	14	3
rifapentine	1	N-alkylpiperazine; N-iminopiperazine; rifamycins	antitubercular agent; leprostatic drug	2009	2009	15.0	low	0	1	0	0
rifabutin	1			2014	2014	10.0	low	0	0	1	0
amg531	1			2022	2022	2.0	low	0	0	0	1

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	2000's	2010's	post-2020
glyoxylic acid	1	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2020	2020	4.0	low	0	0	1	0
naphthalene	1	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component	2018	2018	6.0	low	0	0	1	0
phosphorylcholine	1	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite	2015	2015	9.0	low	0	0	1	0
pyrazinamide	41	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug	2006	2023	7.5	low	5	7	25	9
pyridine	1	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound	2019	2019	5.0	low	0	0	1	0
pyridoxine	1	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2020	2020	4.0	low	0	0	1	0
acetaminophen	1	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	2017	2017	7.0	low	0	0	1	0
verapamil	8	aromatic ether; nitrile; polyether; tertiary amino compound		2014	2019	7.5	low	0	0	8	0
clofazimine	66	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug	2012	2023	5.3	medium	3	0	46	20
dapsone	1	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug	2012	2012	12.0	low	1	0	1	0
deferoxamine	1	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore	2021	2021	3.0	low	0	0	0	1
fenfluramine	1	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor	2007	2007	17.0	low	0	1	0	0
glyburide	1	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent	2020	2020	4.0	low	0	0	1	0
miltefosine	1	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor	2015	2015	9.0	low	0	0	1	0
isoniazid	27	carbohydrazide	antitubercular agent; drug allergen	2007	2023	6.9	low	2	4	17	6
2-propanol	1	secondary alcohol; secondary fatty alcohol	protic solvent	2019	2019	5.0	low	0	0	1	0
manidipine	1	diarylmethane		2021	2021	3.0	low	0	0	0	1
miconazole	1	dichlorobenzene; ether; imidazoles		2020	2020	4.0	low	0	0	1	0
nevirapine	4	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor	2014	2019	7.5	low	1	0	4	0
nitromide	1			2016	2016	8.0	low	0	0	1	0
ofloxacin	2	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline		2012	2018	9.0	low	1	0	2	0
aminosalicylic acid	3	aminobenzoic acid; phenols	antitubercular agent	2017	2020	5.0	low	0	0	3	0
propranolol	1	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic	2014	2014	10.0	low	0	0	1	0
gatifloxacin	1	N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antiinfective agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	2017	2017	7.0	low	0	0	1	0
tyrphostin a9	1	alkylbenzene	geroprotector	2011	2011	13.0	low	0	0	1	0
reserpine	1	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic	2014	2014	10.0	low	0	0	1	0
alanine	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite	2016	2016	8.0	low	0	0	1	0
uridine	1	uridines	drug metabolite; fundamental metabolite; human metabolite	2016	2016	8.0	low	0	0	1	0
kanamycin a	6	kanamycins	bacterial metabolite	2018	2021	4.5	low	0	0	4	2
carbostyril	3	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite	2013	2015	10.0	low	0	0	3	0
leucine	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite	2021	2021	3.0	low	0	0	0	1
methionine	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical	2006	2006	18.0	low	0	1	0	0
cycloserine	5	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist	2012	2021	5.8	low	1	0	4	1
tryptophan	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite	2016	2016	8.0	low	0	0	1	0
propionamide	1	monocarboxylic acid amide; primary fatty amide		2019	2019	5.0	low	0	0	1	0
quinoline	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines		2017	2017	7.0	low	0	0	1	0
xanthenes	5	xanthene		2012	2019	8.0	low	0	0	5	0
trehalose	1	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite	2021	2021	3.0	low	0	0	0	1
pyrroles	1	pyrrole; secondary amine		2010	2010	14.0	low	0	1	0	0
adamantane	14	adamantanes; polycyclic alkane		2007	2019	11.1	low	0	5	9	0
isoxazoles	3	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene		2012	2019	7.3	low	1	0	3	0
oxazoles	117	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene		2008	2023	6.1	medium	2	2	93	22
alpha-aminopyridine	1			2016	2016	8.0	low	0	0	1	0
azomycin	152	C-nitro compound; imidazoles	antitubercular agent	2006	2023	6.5	medium	9	7	114	31
resazurin	5	phenoxazine		2012	2019	8.0	low	0	0	5	0
erythromycin	1	cyclic ketone; erythromycin		2012	2012	12.0	low	1	0	1	0
ethambutol	11	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic	2012	2023	6.1	low	1	0	9	2
streptomycin	2	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor	2006	2012	15.0	low	0	1	1	0
bromine	2	diatomic bromine		2008	2012	14.0	low	1	1	1	0
phenyl acetate	1	benzenes; phenyl acetates		2019	2019	5.0	low	0	0	1	0
azides	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor	2020	2020	4.0	low	0	0	1	0
amikacin	7	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin	2006	2021	6.1	low	0	1	4	2
pimonidazole	1			2007	2007	17.0	low	0	1	0	0
efavirenz	2	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor	2012	2013	11.5	low	2	0	2	0
lissamine rhodamine b	1			2019	2019	5.0	low	0	0	1	0
terizidone	3			2012	2019	7.3	medium	1	0	3	0
lercanidipine	1	diarylmethane		2021	2021	3.0	low	0	0	0	1
triazoles	1	1,2,3-triazole		2020	2020	4.0	low	0	0	1	0
fluorodeoxyglucose f18	1	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose		2015	2015	9.0	low	0	0	1	0
oxazolidin-2-one	20	carbamate ester; oxazolidinone	metabolite	2006	2023	9.8	low	2	5	14	1
clarithromycin	5	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic	2012	2021	7.8	low	2	0	4	1
lopinavir	4	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor	2014	2017	8.2	low	1	0	4	0
imipenem, anhydrous	3	beta-lactam antibiotic allergen; carbapenems; zwitterion	antibacterial drug	2019	2021	4.0	low	0	0	2	1
efonidipine	1	C-nitro compound; carboxylic ester; dihydropyridine; tertiary amino compound		2021	2021	3.0	low	0	0	0	1
carbapenems	5			2010	2018	8.6	low	0	1	4	0
beta-lactams	2	beta-lactam antibiotic allergen; beta-lactam		2017	2019	6.0	low	0	0	2	0
proline	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite	2021	2021	3.0	low	0	0	0	1
levofloxacin	7	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor	2014	2023	4.9	low	0	0	5	2
moxifloxacin	38	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug	2006	2023	7.7	low	5	6	25	7
azd2563	2			2014	2016	9.0	low	0	0	2	0
cholic acid	1	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite	2015	2015	9.0	low	0	0	1	0
trimethoprim, sulfamethoxazole drug combination	1			2018	2018	6.0	low	0	0	1	0
ritonavir	4	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic	2014	2017	8.2	low	1	0	4	0
dihydropyridines	1			2021	2021	3.0	low	0	0	0	1
meropenem	2	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen	2012	2023	6.5	low	0	0	1	1
linezolid	75	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor	2006	2023	5.0	low	8	4	41	30
betadex	1	cyclodextrin		2021	2021	3.0	low	0	0	0	1
zithromax	1	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic	2017	2017	7.0	low	0	0	1	0
pa 824	47			2006	2023	6.4	high	9	4	27	16
u 100480	5			2012	2017	9.0	medium	0	0	5	0
abt 492	2			2020	2021	3.5	low	0	0	1	1
prothionamide	1	pyridines		2018	2018	6.0	low	0	0	1	0
cinnarizine	1	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist	2019	2019	5.0	low	0	0	1	0
ethionamide	6	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug	2006	2020	8.5	low	0	2	4	0
sq-641	1			2016	2016	8.0	medium	0	0	1	0
ovalbumin	1			2016	2016	8.0	low	0	0	1	0
sq 109	14			2007	2019	11.1	high	0	5	9	0
clavulanic acid	1	oxapenam	antibacterial drug; anxiolytic drug; bacterial metabolite; EC 3.5.2.6 (beta-lactamase) inhibitor	2015	2015	9.0	low	0	0	1	0
montelukast	1	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist	2019	2019	5.0	low	0	0	1	0
menaquinone 6	1			2015	2015	9.0	low	0	0	1	0
sulfur	1	chalcogen; nonmetal atom	macronutrient	2023	2023	1.0	low	0	0	0	1
fumarates	1	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite	2023	2023	1.0	low	0	0	0	1
aurachin d	1	sesquiterpenoid		2015	2015	9.0	low	0	0	1	0
cgp-56697	1			2015	2015	9.0	low	0	0	1	0
sudoterb	1			2010	2010	14.0	medium	0	1	0	0
opc-67683	121	piperidines		2008	2023	5.9	high	3	2	92	27
acebutolol	1	alpha-D-glucosyl-(1->4)-D-mannopyranose		2021	2021	3.0	low	0	0	0	1
tedizolid	1	carbamate ester; organofluorine compound; oxazolidinone; primary alcohol; pyridines; tetrazoles	antimicrobial agent; drug metabolite; protein synthesis inhibitor	2020	2020	4.0	low	0	0	1	0
tedizolid phosphate	1	carbamate ester; organofluorine compound; oxazolidinone; phosphate monoester; pyridines; tetrazoles	antimicrobial agent; prodrug; protein synthesis inhibitor	2016	2016	8.0	low	0	0	1	0
crizotinib	1	3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine	antineoplastic agent; biomarker; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor	2013	2013	11.0	low	0	0	1	0
rifamycins	5			2005	2020	12.0	low	0	3	2	0
mefloquine	1			2017	2017	7.0	low	0	0	1	0
rwj-416457	1			2016	2016	8.0	medium	0	0	1	0
bivalirudin	1	polypeptide	anticoagulant; EC 3.4.21.5 (thrombin) inhibitor	2013	2013	11.0	low	0	0	1	0
cellulose	1	glycoside		2019	2019	5.0	low	0	0	1	0
vx-770	2	aromatic amide; monocarboxylic acid amide; phenols; quinolone	CFTR potentiator; orphan drug	2013	2014	10.5	low	0	0	2	0
chitosan	1			2018	2018	6.0	low	0	0	1	0
florbetapir f 18	1	(18)F radiopharmaceutical; aromatic ether; organofluorine compound; pyridines; substituted aniline	radioactive imaging agent	2014	2014	10.0	low	0	0	1	0
arabinogalactan	1			2021	2021	3.0	low	0	0	0	1
piperidines	5			2016	2021	5.0	low	0	0	4	1
colistin	1			2018	2018	6.0	low	0	0	1	0
tba-354	1			2015	2015	9.0	medium	0	0	1	0
abt-199	1	aromatic ether; C-nitro compound; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; N-sulfonylcarboxamide; oxanes; pyrrolopyridine	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor	2019	2019	5.0	low	0	0	1	0
minocycline	2			2014	2016	9.0	low	0	0	2	0
tigecycline	2			2014	2016	9.0	low	0	0	2	0
eravacycline	2	tetracyclines		2020	2021	3.5	low	0	0	1	1
rpx7009	1			2023	2023	1.0	low	0	0	0	1
pbtz169	2			2015	2016	8.5	low	0	0	2	0
cpzen-45	1			2016	2016	8.0	low	0	0	1	0
agar	1			2015	2015	9.0	low	0	0	1	0
hirudin	1			2013	2013	11.0	low	0	0	1	0
nitrophenols	1			2021	2021	3.0	low	0	0	0	1
cord factors	1			2021	2021	3.0	low	0	0	0	1
trehalose monomycolate	1			2021	2021	3.0	low	0	0	0	1
rifampin	70	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor	2006	2023	6.4	low	13	11	31	28
rifapentine	13	N-alkylpiperazine; N-iminopiperazine; rifamycins	antitubercular agent; leprostatic drug	2009	2020	10.7	low	2	4	9	0
PF-07304814	1	aromatic ether; indolecarboxamide; L-leucine derivative; phosphate monoester; pyrrolidin-2-ones; secondary carboxamide	anticoronaviral agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; prodrug	2021	2021	3.0	medium	0	0	0	1

Condition	Indicated	Studies	First Year	Last Year	Average Age	Relationship Strength	Trials	2000's	2010's	post-2020
2019 Novel Coronavirus Disease	0	1	2020	2020	4.0	low	0	0	1	0
Abscess	0	1	2023	2023	1.0	low	0	0	0	1
Acquired Immune Deficiency Syndrome	0	1	2022	2022	2.0	low	0	0	0	1
Acquired Immunodeficiency Syndrome	0	1	2022	2022	2.0	low	0	0	0	1
Acute Confusional Senile Dementia	0	1	2014	2014	10.0	low	0	0	1	0
Acute Liver Injury, Drug-Induced	0	3	2019	2023	3.7	low	0	0	2	1
Acute Myelogenous Leukemia	0	1	2021	2021	3.0	low	0	0	0	1
Adverse Drug Event	0	8	2013	2024	4.9	low	0	0	4	4
AIDS Seroconversion	0	2	2022	2023	1.5	low	0	0	0	2
AIDS-Related Opportunistic Infections	0	2	2017	2018	6.5	low	0	0	2	0
Alzheimer Disease	0	1	2014	2014	10.0	low	0	0	1	0
Anemia	0	2	2019	2020	4.5	low	0	0	2	0
Angiogenesis, Pathologic	0	1	2018	2018	6.0	low	0	0	1	0
Angioma	0	1	2014	2014	10.0	low	0	0	1	0
Anorexia	0	1	2015	2015	9.0	low	0	0	1	0
Anoxemia	0	1	2007	2007	17.0	low	0	1	0	0
Anterior Optic Neuritis	0	1	2019	2019	5.0	low	0	0	1	0
Apoplexy	0	1	2021	2021	3.0	low	0	0	0	1
Arrhythmia	0	4	2015	2018	7.2	low	0	0	4	0
Arrhythmias, Cardiac	0	4	2015	2018	7.2	low	0	0	4	0
Arthralgia	0	1	2015	2015	9.0	low	0	0	1	0
Atypical Mycobacterial Infection, Disseminated	0	23	2006	2022	5.8	low	1	1	15	7
Autoimmune Diabetes	0	1	2016	2016	8.0	low	0	0	1	0
Bacterial Skin Diseases	0	1	2020	2020	4.0	low	0	0	1	0
Body Weight	0	1	2016	2016	8.0	low	1	0	1	0
Buruli Ulcer	0	2	2016	2020	6.0	low	0	0	2	0
Buruli Ulcer Disease	0	2	2016	2020	6.0	low	0	0	2	0
Cancer of Lung	0	3	2018	2021	4.0	low	0	0	1	2
Cancer of Ovary	0	1	2023	2023	1.0	low	0	0	0	1
Carcinoma, Non-Small Cell Lung	0	2	2021	2021	3.0	low	0	0	0	2
Carcinoma, Non-Small-Cell Lung	0	2	2021	2021	3.0	low	0	0	0	2
Cardiac Toxicity	0	5	2018	2019	5.4	low	0	0	5	0
Cardiotoxicity	0	5	2018	2019	5.4	low	0	0	5	0
Cardiovascular Diseases	0	2	2019	2023	3.0	low	0	0	1	1
Cardiovascular Stroke	0	2	2013	2020	7.5	low	1	0	2	0
Cervical Tuberculous Lymphadenitis	0	1	2021	2021	3.0	low	0	0	0	1
Chemical and Drug Induced Liver Injury	0	3	2019	2023	3.7	low	0	0	2	1
Chronic Kidney Failure	0	1	2018	2018	6.0	low	0	0	1	0
Co-infection	0	16	2014	2021	5.6	low	2	0	14	2
Communicable Diseases	0	1	2023	2023	1.0	low	0	0	0	1
Complications of Diabetes Mellitus	0	1	2023	2023	1.0	low	0	0	0	1
Complications, Infectious Pregnancy	0	1	2017	2017	7.0	low	0	0	1	0
Congenital Zika Syndrome	0	1	2020	2020	4.0	low	0	0	1	0
Coronavirus Infections	0	1	2020	2020	4.0	low	0	0	1	0
Cystic Fibrosis	0	1	2014	2014	10.0	low	0	0	1	0
Cystic Fibrosis of Pancreas	0	1	2014	2014	10.0	low	0	0	1	0
Deaf Mutism	0	1	2019	2019	5.0	low	0	0	1	0
Deafness	0	1	2019	2019	5.0	low	0	0	1	0
Dermatitis Medicamentosa	0	1	2020	2020	4.0	low	0	0	1	0
Diabetes Mellitus, Adult-Onset	0	1	2016	2016	8.0	low	0	0	1	0
Diabetes Mellitus, Type 1	0	1	2016	2016	8.0	low	0	0	1	0
Diabetes Mellitus, Type 2	0	1	2016	2016	8.0	low	0	0	1	0
Diarrhea	0	1	2020	2020	4.0	low	0	0	1	0
Disease Models, Animal	0	27	2008	2022	8.9	low	0	5	18	4
Disease, Pulmonary	0	2	2019	2019	5.0	low	0	0	2	0
Drug Overdose	0	1	2019	2019	5.0	low	0	0	1	0
Drug-Related Side Effects and Adverse Reactions	0	8	2013	2024	4.9	low	0	0	4	4
Electrocardiogram QT Prolonged	0	16	2013	2023	4.2	low	1	0	9	7
Electrolytes	0	2	2022	2022	2.0	low	0	0	0	2
Emesis	0	2	2020	2020	4.0	low	0	0	2	0
Encephalopathy, Toxic	0	1	2020	2020	4.0	low	0	0	1	0
Exanthem	0	1	2020	2020	4.0	low	0	0	1	0
Exanthema	0	1	2020	2020	4.0	low	0	0	1	0
Extensively Drug-Resistant Tuberculosis	0	84	2011	2023	5.8	medium	3	0	65	19
Fever	0	1	2015	2015	9.0	low	0	0	1	0
Granuloma	0	2	2007	2021	10.0	low	0	1	0	1
Granulomas	0	2	2007	2021	10.0	low	0	1	0	1
Hansen Disease	0	3	2006	2023	11.3	low	1	2	0	1
Hemangioma	0	1	2014	2014	10.0	low	0	0	1	0
Hepatitis C	0	1	2018	2018	6.0	low	0	0	1	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted	0	1	2018	2018	6.0	low	0	0	1	0
HIV	0	3	2019	2022	3.3	low	0	0	1	2
HIV Coinfection	0	41	2012	2023	5.5	low	5	0	31	10
HIV Infections	0	41	2012	2023	5.5	low	5	0	31	10
Hypoxia	0	1	2007	2007	17.0	low	0	1	0	0
Incontinentia Pigmenti Achromians	0	1	2020	2020	4.0	low	0	0	1	0
Infection Reactivation	0	1	2023	2023	1.0	low	0	0	0	1
Infection, Mycobacterium avium-intracellulare	0	5	2015	2021	6.2	low	0	0	4	1
Infections, Coronavirus	0	1	2020	2020	4.0	low	0	0	1	0
Infections, Mycobacterium	0	3	2014	2017	8.7	low	0	0	3	0
Infections, Soft Tissue	0	1	2020	2020	4.0	low	0	0	1	0
Infectious Diseases	0	1	2023	2023	1.0	low	0	0	0	1
Inflammation	0	2	2017	2023	4.0	low	0	0	1	1
Injuries, Soft Tissue	0	1	2020	2020	4.0	low	0	0	1	0
Injury, Ischemia-Reperfusion	0	1	2021	2021	3.0	low	0	0	0	1
Innate Inflammatory Response	0	2	2017	2023	4.0	low	0	0	1	1
Iron Metabolism Disorders	0	1	2023	2023	1.0	low	0	0	0	1
Joint Pain	0	1	2015	2015	9.0	low	0	0	1	0
Kidney Failure, Chronic	0	1	2018	2018	6.0	low	0	0	1	0
Koch's Disease	0	111	2004	2024	8.1	low	5	22	66	23
Laryngeal Tuberculosis	0	1	2016	2016	8.0	low	0	0	1	0
Latent Tuberculosis	0	3	2011	2018	10.3	low	0	0	3	0
Leanness	0	1	2020	2020	4.0	low	0	0	1	0
Leprosy	1	3	2006	2023	11.3	low	1	2	0	1
Leukemia, Myeloid, Acute	0	1	2021	2021	3.0	low	0	0	0	1
Long QT Syndrome	0	16	2013	2023	4.2	low	1	0	9	7
Lung Diseases	0	2	2019	2019	5.0	low	0	0	2	0
Lung Neoplasms	0	3	2018	2021	4.0	low	0	0	1	2
Malnourishment	0	1	2020	2020	4.0	low	0	0	1	0
Malnutrition	0	1	2020	2020	4.0	low	0	0	1	0
Meningitis, Tuberculous	0	1	2016	2016	8.0	low	0	0	1	0
Metastase	0	1	2021	2021	3.0	low	0	0	0	1
MS (Multiple Sclerosis)	0	1	2016	2016	8.0	low	0	0	1	0
Multiple Sclerosis	0	1	2016	2016	8.0	low	0	0	1	0
Mycobacterium avium-intracellulare Infection	1	5	2015	2021	6.2	low	0	0	4	1
Mycobacterium Infections	0	3	2014	2017	8.7	low	0	0	3	0
Myocardial Infarction	0	2	2013	2020	7.5	low	1	0	2	0
Nausea	0	1	2015	2015	9.0	low	0	0	1	0
Neglected Diseases	0	1	2015	2015	9.0	low	0	0	1	0
Neoplasm Metastasis	0	1	2021	2021	3.0	low	0	0	0	1
Optic Neuritis	0	1	2019	2019	5.0	low	0	0	1	0
Orphan Diseases	0	1	2015	2015	9.0	low	0	0	1	0
Osteomyelitis	0	1	2021	2021	3.0	low	0	0	0	1
Ovarian Neoplasms	0	1	2023	2023	1.0	low	0	0	0	1
Peripheral Nerve Diseases	0	3	2019	2020	4.3	low	0	0	3	0
Peripheral Nervous System Diseases	0	3	2019	2020	4.3	low	0	0	3	0
Pneumonia, Viral	0	1	2020	2020	4.0	low	0	0	1	0
Pregnancy	0	7	2013	2023	4.4	low	0	0	3	4
Pulmonary Consumption	0	66	2005	2023	7.8	low	11	11	44	11
Pyrexia	0	1	2015	2015	9.0	low	0	0	1	0
Recrudescence	0	5	2011	2021	6.8	low	0	0	4	1
Reperfusion Injury	0	1	2021	2021	3.0	low	0	0	0	1
Sensitivity and Specificity	0	7	2008	2019	10.4	low	0	3	4	0
Skin Diseases, Bacterial	0	1	2020	2020	4.0	low	0	0	1	0
Soft Tissue Infections	0	1	2020	2020	4.0	low	0	0	1	0
Stroke	0	1	2021	2021	3.0	low	0	0	0	1
Torsade de Pointes	0	1	2018	2018	6.0	low	0	0	1	0
Tuberculosis	1	111	2004	2024	8.1	low	5	22	66	23
Tuberculosis, Drug-Resistant	0	364	2005	2024	5.5	high	26	6	240	118
Tuberculosis, Meningeal	0	1	2016	2016	8.0	low	0	0	1	0
Tuberculosis, Multidrug-Resistant	1	364	2005	2024	5.5	high	26	6	240	118
Tuberculosis, Pulmonary	1	66	2005	2023	7.8	low	11	11	44	11
Tuberculosis, Splenic	0	1	2009	2009	15.0	low	0	1	0	0
Vomiting	0	2	2020	2020	4.0	low	0	0	2	0
Zika Virus Infection	0	1	2020	2020	4.0	low	0	0	1	0

Safety/Toxicity (39)

Article	Year
A phase IIb, open-label, randomized controlled dose ranging multi-centre trial to evaluate the safety, tolerability, pharmacokinetics and exposure-response relationship of different doses of delpazolid in combination with bedaquiline delamanid moxifloxaci Trials, , Jun-06, Volume: 24, Issue:1	2023
Comparative safety of bedaquiline and delamanid in patients with multidrug resistant tuberculosis: A nationwide retrospective cohort study. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi, , Volume: 56, Issue:4	2023
Bedaquiline's Safety Profile Monitoring in India: Considerations for Future - A Systematic Review. Current drug safety, , Volume: 19, Issue:1	2024
Molecular mechanism for the involvement of CYP2E1/NF-κB axis in bedaquiline-induced hepatotoxicity. Life sciences, , Feb-15, Volume: 315	2023
Effectiveness and safety of bedaquiline-based, modified all-oral 9-11-month treatment regimen for rifampicin-resistant tuberculosis in Vietnam. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, , Volume: 126	2023
Effectiveness and safety of bedaquiline-containing regimens for treatment on patients with refractory RR/MDR/XDR-tuberculosis: a retrospective cohort study in East China. BMC infectious diseases, , Aug-29, Volume: 22, Issue:1	2022
Randomised trial to evaluate the effectiveness and safety of varying doses of linezolid with bedaquiline and pretomanid in adults with pre-extensively drug-resistant or treatment intolerant/non-responsive multidrug-resistant pulmonary tuberculosis: study BMJ open, , 08-29, Volume: 12, Issue:8	2022
TB-PRACTECAL: study protocol for a randomised, controlled, open-label, phase II-III trial to evaluate the safety and efficacy of regimens containing bedaquiline and pretomanid for the treatment of adult patients with pulmonary multidrug-resistant tubercul Trials, , Jun-13, Volume: 23, Issue:1	2022
Assessing Prolongation of the Corrected QT Interval with Bedaquiline and Delamanid Coadministration to Predict the Cardiac Safety of Simplified Dosing Regimens. Clinical pharmacology and therapeutics, , Volume: 112, Issue:4	2022
Pharmacokinetics and Safety of Bedaquiline in Human Immunodeficiency Virus (HIV)-Positive and Negative Older Children and Adolescents With Rifampicin-Resistant Tuberculosis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 11-14, Volume: 75, Issue:10	2022
Safety and Effectiveness Outcomes From a 14-Country Cohort of Patients With Multi-Drug Resistant Tuberculosis Treated Concomitantly With Bedaquiline, Delamanid, and Other Second-Line Drugs. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 10-12, Volume: 75, Issue:8	2022
Optimizing cardio, hepato and phospholipidosis toxicity of the Bedaquiline by chemoinformatics and molecular modelling approach. SAR and QSAR in environmental research, , Volume: 33, Issue:3	2022
A modeling-based proposal for safe and efficacious reintroduction of bedaquiline after dose interruption: A population pharmacokinetics study. CPT: pharmacometrics & systems pharmacology, , Volume: 11, Issue:5	2022
Safety of Treatment Regimens Containing Bedaquiline and Delamanid in the endTB Cohort. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 09-29, Volume: 75, Issue:6	2022
Exposure-safety analysis of QTc interval and transaminase levels following bedaquiline administration in patients with drug-resistant tuberculosis. CPT: pharmacometrics & systems pharmacology, , Volume: 10, Issue:12	2021
Safety, efficacy, and serum concentration monitoring of bedaquiline in Chinese patients with multidrug-resistant tuberculosis. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, , Volume: 110	2021
Analysis of the side effect of QTc interval prolongation in the bedaquiline regimen in drug resistant tuberculosis patients. Journal of basic and clinical physiology and pharmacology, , Jun-25, Volume: 32, Issue:4	2021
Effectiveness and Cardiac Safety of Bedaquiline-Based Therapy for Drug-Resistant Tuberculosis: A Prospective Cohort Study. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 12-06, Volume: 73, Issue:11	2021
Bedaquiline-containing regimens in patients with pulmonary multidrug-resistant tuberculosis in China: focus on the safety. Infectious diseases of poverty, , Mar-19, Volume: 10, Issue:1	2021
Effectiveness and safety of delamanid- or bedaquiline-containing regimens among children and adolescents with multidrug resistant or extensively drug resistant tuberculosis: A nationwide study from Belarus, 2015-19. Monaldi archives for chest disease = Archivio Monaldi per le malattie del torace, , Jan-14, Volume: 91, Issue:1	2021
Safety and Effectiveness of an All-Oral, Bedaquiline-Based, Shorter Treatment Regimen for Rifampicin-Resistant Tuberculosis in High Human Immunodeficiency Virus (HIV) Burden Rural South Africa: A Retrospective Cohort Analysis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 11-02, Volume: 73, Issue:9	2021
Treatment interruption patterns and adverse events among patients on bedaquiline containing regimen under programmatic conditions in India. Pulmonology, , Volume: 28, Issue:3
Outcomes and adverse events of pre- and extensively drug-resistant tuberculosis patients in Kinshasa, Democratique Republic of the Congo: A retrospective cohort study. PloS one, , Volume: 15, Issue:8	2020
Preserved Efficacy and Reduced Toxicity with Intermittent Linezolid Dosing in Combination with Bedaquiline and Pretomanid in a Murine Tuberculosis Model. Antimicrobial agents and chemotherapy, , 09-21, Volume: 64, Issue:10	2020
Early outcome and safety of bedaquiline-containing regimens for treatment of MDR- and XDR-TB in China: a multicentre study. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, , Volume: 27, Issue:4	2021
Effectiveness and safety of bedaquiline under conditional access program for treatment of drug-resistant tuberculosis in India: An interim analysis. The Indian journal of tuberculosis, , Volume: 67, Issue:1	2020
Drug-associated adverse events in the treatment of multidrug-resistant tuberculosis: an individual patient data meta-analysis. The Lancet. Respiratory medicine, , Volume: 8, Issue:4	2020
Bedaquiline in multidrug-resistant tuberculosis treatment: Safety and efficacy in a Korean subpopulation. Respiratory investigation, , Volume: 58, Issue:1	2020
Surveillance of adverse events in the treatment of drug-resistant tuberculosis: A global feasibility study. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, , Volume: 83	2019
Early efficacy and safety of Bedaquiline and Delamanid given together in a "Salvage Regimen" for treatment of drug-resistant tuberculosis. The Indian journal of tuberculosis, , Volume: 66, Issue:1	2019
Safety, efficacy, and pharmacokinetics of bedaquiline in Japanese patients with pulmonary multidrug-resistant tuberculosis: An interim analysis of an open-label, phase 2 study. Respiratory investigation, , Volume: 57, Issue:4	2019
Early safety and efficacy of the combination of bedaquiline and delamanid for the treatment of patients with drug-resistant tuberculosis in Armenia, India, and South Africa: a retrospective cohort study. The Lancet. Infectious diseases, , Volume: 18, Issue:5	2018
Supramolecular strategy for reducing the cardiotoxicity of bedaquiline without compromising its antimycobacterial efficacy. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, , Volume: 119	2018
Dose- and Time-dependency of the Toxicity and Pharmacokinetic Profiles of Bedaquiline and Its N-desmethyl Metabolite in Dogs. Toxicologic pathology, , Volume: 45, Issue:5	2017
Effectiveness and safety of bedaquiline-containing regimens in the treatment of MDR- and XDR-TB: a multicentre study. The European respiratory journal, , Volume: 49, Issue:5	2017
Long-term outcome and safety of prolonged bedaquiline treatment for multidrug-resistant tuberculosis. The European respiratory journal, , Volume: 49, Issue:3	2017
Adverse effects of oral second-line antituberculosis drugs in children. Expert opinion on drug safety, , Volume: 15, Issue:10	2016
Provisional CDC guidelines for the use and safety monitoring of bedaquiline fumarate (Sirturo) for the treatment of multidrug-resistant tuberculosis. MMWR. Recommendations and reports : Morbidity and mortality weekly report. Recommendations and reports, , Oct-25, Volume: 62, Issue:RR-09	2013
Safety, tolerability, and pharmacokinetic interactions of the antituberculous agent TMC207 (bedaquiline) with efavirenz in healthy volunteers: AIDS Clinical Trials Group Study A5267. Journal of acquired immune deficiency syndromes (1999), , Apr-15, Volume: 59, Issue:5	2012

Long-term Use (1)

Article	Year
Bedaquiline: a new hope to treat multi-drug resistant tuberculosis. Current topics in medicinal chemistry, , Volume: 14, Issue:16	2014

Pharmacokinetics (28)

Article	Year
Predictions of Bedaquiline and Pretomanid Target Attainment in Lung Lesions of Tuberculosis Patients using Translational Minimal Physiologically Based Pharmacokinetic Modeling. Clinical pharmacokinetics, , Volume: 62, Issue:3	2023
Pharmacodynamics and Bactericidal Activity of Combination Regimens in Pulmonary Tuberculosis: Application to Bedaquiline-Pretomanid-Pyrazinamide. Antimicrobial agents and chemotherapy, , 12-20, Volume: 66, Issue:12	2022
Population Pharmacokinetics of Delamanid and its Main Metabolite DM-6705 in Drug-Resistant Tuberculosis Patients Receiving Delamanid Alone or Coadministered with Bedaquiline. Clinical pharmacokinetics, , Volume: 61, Issue:8	2022
Pharmacokinetics and Safety of Bedaquiline in Human Immunodeficiency Virus (HIV)-Positive and Negative Older Children and Adolescents With Rifampicin-Resistant Tuberculosis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 11-14, Volume: 75, Issue:10	2022
Pharmacokinetics of bedaquiline in cerebrospinal fluid (CSF) in patients with pulmonary tuberculosis (TB). The Journal of antimicrobial chemotherapy, , 05-29, Volume: 77, Issue:6	2022
A modeling-based proposal for safe and efficacious reintroduction of bedaquiline after dose interruption: A population pharmacokinetics study. CPT: pharmacometrics & systems pharmacology, , Volume: 11, Issue:5	2022
Pharmacogenetics of Between-Individual Variability in Plasma Clearance of Bedaquiline and Clofazimine in South Africa. The Journal of infectious diseases, , 08-12, Volume: 226, Issue:1	2022
A Scoping Review of the Clinical Pharmacokinetics of Bedaquiline. Clinical pharmacokinetics, , Volume: 61, Issue:4	2022
Bacterial growth dynamics and pharmacokinetic-pharmacodynamic relationships of rifampicin and bedaquiline in BALB/c mice. British journal of pharmacology, , Volume: 179, Issue:6	2022
Population Pharmacokinetic Analysis of Bedaquiline-Clarithromycin for Dose Selection Against Pulmonary Nontuberculous Mycobacteria Based on a Phase 1, Randomized, Pharmacokinetic Study. Journal of clinical pharmacology, , Volume: 61, Issue:10	2021
Pharmacokinetics of bedaquiline, delamanid and clofazimine in patients with multidrug-resistant tuberculosis. The Journal of antimicrobial chemotherapy, , 03-12, Volume: 76, Issue:4	2021
Plasma pharmacokinetics of bedaquiline administered by nasogastric tube in an intensive care unit. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, , 01-01, Volume: 24, Issue:1	2020
Effect of Natural Phenolics on Pharmacokinetic Modulation of Bedaquiline in Rat to Assess the Likelihood of Potential Food-Drug Interaction. Journal of agricultural and food chemistry, , Feb-05, Volume: 68, Issue:5	2020
Safety, efficacy, and pharmacokinetics of bedaquiline in Japanese patients with pulmonary multidrug-resistant tuberculosis: An interim analysis of an open-label, phase 2 study. Respiratory investigation, , Volume: 57, Issue:4	2019
Long-term plasma pharmacokinetics of bedaquiline for multidrug- and extensively drug-resistant tuberculosis. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, , 01-01, Volume: 23, Issue:1	2019
Predicting the Outcomes of New Short-Course Regimens for Multidrug-Resistant Tuberculosis Using Intrahost and Pharmacokinetic-Pharmacodynamic Modeling. Antimicrobial agents and chemotherapy, , Volume: 62, Issue:12	2018
Pharmacokinetic interaction between bedaquiline and clofazimine in patients with drug-resistant tuberculosis. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, , 01-01, Volume: 22, Issue:1	2018
Dose- and Time-dependency of the Toxicity and Pharmacokinetic Profiles of Bedaquiline and Its N-desmethyl Metabolite in Dogs. Toxicologic pathology, , Volume: 45, Issue:5	2017
Confirming model-predicted pharmacokinetic interactions between bedaquiline and lopinavir/ritonavir or nevirapine in patients with HIV and drug-resistant tuberculosis. International journal of antimicrobial agents, , Volume: 49, Issue:2	2017
Population Pharmacokinetics of Bedaquiline and Metabolite M2 in Patients With Drug-Resistant Tuberculosis: The Effect of Time-Varying Weight and Albumin. CPT: pharmacometrics & systems pharmacology, , Volume: 5, Issue:12	2016
Pharmacokinetic Interactions for Drugs with a Long Half-Life—Evidence for the Need of Model-Based Analysis. The AAPS journal, , Volume: 18, Issue:1	2016
Evaluation of the pharmacokinetic interaction between repeated doses of rifapentine or rifampin and a single dose of bedaquiline in healthy adult subjects. Antimicrobial agents and chemotherapy, , Volume: 59, Issue:2	2015
Population pharmacokinetics of bedaquiline (TMC207), a novel antituberculosis drug. Antimicrobial agents and chemotherapy, , Volume: 58, Issue:9	2014
Bedaquiline: a review of human pharmacokinetics and drug-drug interactions. The Journal of antimicrobial chemotherapy, , Volume: 69, Issue:9	2014
Model-based estimates of the effects of efavirenz on bedaquiline pharmacokinetics and suggested dose adjustments for patients coinfected with HIV and tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 57, Issue:6	2013
Pharmacokinetics and pharmacodynamics of TMC207 and its N-desmethyl metabolite in a murine model of tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 56, Issue:3	2012
Safety, tolerability, and pharmacokinetic interactions of the antituberculous agent TMC207 (bedaquiline) with efavirenz in healthy volunteers: AIDS Clinical Trials Group Study A5267. Journal of acquired immune deficiency syndromes (1999), , Apr-15, Volume: 59, Issue:5	2012
Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 52, Issue:8	2008

Bioavailability (10)

Article	Year
Pharmacokinetics and Safety of Bedaquiline in Human Immunodeficiency Virus (HIV)-Positive and Negative Older Children and Adolescents With Rifampicin-Resistant Tuberculosis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 11-14, Volume: 75, Issue:10	2022
Active pulmonary targeting against tuberculosis (TB) via triple-encapsulation of Q203, bedaquiline and superparamagnetic iron oxides (SPIOs) in nanoparticle aggregates. Drug delivery, , Volume: 26, Issue:1	2019
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology, , Volume: 96, Issue:5	2019
Pharmacokinetic interaction between bedaquiline and clofazimine in patients with drug-resistant tuberculosis. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, , 01-01, Volume: 22, Issue:1	2018
Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units. Bioorganic & medicinal chemistry letters, , 12-01, Volume: 27, Issue:23	2017
Verapamil Increases the Bioavailability and Efficacy of Bedaquiline but Not Clofazimine in a Murine Model of Tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 62, Issue:1	2018
Novel, potent, orally bioavailable and selective mycobacterial ATP synthase inhibitors that demonstrated activity against both replicating and non-replicating M. tuberculosis. Bioorganic & medicinal chemistry, , Feb-15, Volume: 23, Issue:4	2015
Bedaquiline: a novel antitubercular agent for the treatment of multidrug-resistant tuberculosis. Pharmacotherapy, , Volume: 34, Issue:11	2014
Population pharmacokinetics of bedaquiline (TMC207), a novel antituberculosis drug. Antimicrobial agents and chemotherapy, , Volume: 58, Issue:9	2014
Synthesis and antimycobacterial activity of prodrugs of indeno[2,1-c]quinoline derivatives. European journal of medicinal chemistry, , Volume: 46, Issue:4	2011

Dosage (33)

Article	Year
Advances of new drugs bedaquiline and delamanid in the treatment of multi-drug resistant tuberculosis in children. Frontiers in cellular and infection microbiology, , Volume: 13	2023
A phase IIb, open-label, randomized controlled dose ranging multi-centre trial to evaluate the safety, tolerability, pharmacokinetics and exposure-response relationship of different doses of delpazolid in combination with bedaquiline delamanid moxifloxaci Trials, , Jun-06, Volume: 24, Issue:1	2023
Implementation of Bedaquiline, Pretomanid, and Linezolid in the United States: Experience Using a Novel All-Oral Treatment Regimen for Treatment of Rifampin-Resistant or Rifampin-Intolerant Tuberculosis Disease. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, , 10-05, Volume: 77, Issue:7	2023
Predictions of Bedaquiline and Pretomanid Target Attainment in Lung Lesions of Tuberculosis Patients using Translational Minimal Physiologically Based Pharmacokinetic Modeling. Clinical pharmacokinetics, , Volume: 62, Issue:3	2023
Assessing Prolongation of the Corrected QT Interval with Bedaquiline and Delamanid Coadministration to Predict the Cardiac Safety of Simplified Dosing Regimens. Clinical pharmacology and therapeutics, , Volume: 112, Issue:4	2022
A modeling-based proposal for safe and efficacious reintroduction of bedaquiline after dose interruption: A population pharmacokinetics study. CPT: pharmacometrics & systems pharmacology, , Volume: 11, Issue:5	2022
A Scoping Review of the Clinical Pharmacokinetics of Bedaquiline. Clinical pharmacokinetics, , Volume: 61, Issue:4	2022
Impact of drug-resistant tuberculosis treatment on hearing function in South African adults: Bedaquiline versus kanamycin. The South African journal of communication disorders = Die Suid-Afrikaanse tydskrif vir Kommunikasieafwykings, , Jan-26, Volume: 68, Issue:1	2021
Pharmacokinetics of bedaquiline, delamanid and clofazimine in patients with multidrug-resistant tuberculosis. The Journal of antimicrobial chemotherapy, , 03-12, Volume: 76, Issue:4	2021
Preserved Efficacy and Reduced Toxicity with Intermittent Linezolid Dosing in Combination with Bedaquiline and Pretomanid in a Murine Tuberculosis Model. Antimicrobial agents and chemotherapy, , 09-21, Volume: 64, Issue:10	2020
Understanding the drug exposure-response relationship of bedaquiline to predict efficacy for novel dosing regimens in the treatment of multidrug-resistant tuberculosis. British journal of clinical pharmacology, , Volume: 86, Issue:5	2020
The Lancet Respiratory Medicine Commission: 2019 update: epidemiology, pathogenesis, transmission, diagnosis, and management of multidrug-resistant and incurable tuberculosis. The Lancet. Respiratory medicine, , Volume: 7, Issue:9	2019
Daily Dosing for Bedaquiline in Patients with Tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 63, Issue:11	2019
Bedaquiline overdose: A case report. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, , Volume: 84	2019
Modelling the long-acting administration of anti-tuberculosis agents using PBPK: a proof of concept study. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, , 08-01, Volume: 22, Issue:8	2018
Mycobactericidal activity of bedaquiline plus rifabutin or rifampin in ex vivo whole blood cultures of healthy volunteers: A randomized controlled trial. PloS one, , Volume: 13, Issue:5	2018
Modelling of mycobacterial load reveals bedaquiline's exposure-response relationship in patients with drug-resistant TB. The Journal of antimicrobial chemotherapy, , Dec-01, Volume: 72, Issue:12	2017
Dose- and Time-dependency of the Toxicity and Pharmacokinetic Profiles of Bedaquiline and Its N-desmethyl Metabolite in Dogs. Toxicologic pathology, , Volume: 45, Issue:5	2017
Confirming model-predicted pharmacokinetic interactions between bedaquiline and lopinavir/ritonavir or nevirapine in patients with HIV and drug-resistant tuberculosis. International journal of antimicrobial agents, , Volume: 49, Issue:2	2017
Individualizing management of extensively drug-resistant tuberculosis: diagnostics, treatment, and biomarkers. Expert review of anti-infective therapy, , Volume: 15, Issue:1	2017
Preliminary Results of Bedaquiline as Salvage Therapy for Patients With Nontuberculous Mycobacterial Lung Disease. Chest, , Volume: 148, Issue:2	2015
Rifampicin and rifapentine significantly reduce concentrations of bedaquiline, a new anti-TB drug. The Journal of antimicrobial chemotherapy, , Volume: 70, Issue:4	2015
Verapamil increases the bactericidal activity of bedaquiline against Mycobacterium tuberculosis in a mouse model. Antimicrobial agents and chemotherapy, , Volume: 59, Issue:1	2015
Bedaquiline: a novel antitubercular agent for the treatment of multidrug-resistant tuberculosis. Pharmacotherapy, , Volume: 34, Issue:11	2014
Impact of lopinavir-ritonavir or nevirapine on bedaquiline exposures and potential implications for patients with tuberculosis-HIV coinfection. Antimicrobial agents and chemotherapy, , Volume: 58, Issue:11	2014
Principles for designing future regimens for multidrug-resistant tuberculosis. Bulletin of the World Health Organization, , Jan-01, Volume: 92, Issue:1	2014
Bedaquiline: a novel diarylquinoline for multidrug-resistant tuberculosis. The Annals of pharmacotherapy, , Volume: 48, Issue:1	2014
Model-based estimates of the effects of efavirenz on bedaquiline pharmacokinetics and suggested dose adjustments for patients coinfected with HIV and tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 57, Issue:6	2013
Rapid evaluation in whole blood culture of regimens for XDR-TB containing PNU-100480 (sutezolid), TMC207, PA-824, SQ109, and pyrazinamide. PloS one, , Volume: 7, Issue:1	2012
Pharmacokinetics and pharmacodynamics of TMC207 and its N-desmethyl metabolite in a murine model of tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 56, Issue:3	2012
Time to detection of the growth of Mycobacterium tuberculosis in MGIT 960 for determining the early bactericidal activity of antituberculosis agents. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology, , Volume: 29, Issue:12	2010
The diarylquinoline R207910 is bactericidal against Mycobacterium leprae in mice at low dose and administered intermittently. Antimicrobial agents and chemotherapy, , Volume: 53, Issue:9	2009
Hyphenation of reverse-phase HPLC and ICP-MS for metabolite profiling--application to a novel antituberculosis compound as a case study. Analytical and bioanalytical chemistry, , Volume: 389, Issue:3	2007

Interactions (11)

Article	Year
A phase IIb, open-label, randomized controlled dose ranging multi-centre trial to evaluate the safety, tolerability, pharmacokinetics and exposure-response relationship of different doses of delpazolid in combination with bedaquiline delamanid moxifloxaci Trials, , Jun-06, Volume: 24, Issue:1	2023
Population Pharmacokinetics of Delamanid and its Main Metabolite DM-6705 in Drug-Resistant Tuberculosis Patients Receiving Delamanid Alone or Coadministered with Bedaquiline. Clinical pharmacokinetics, , Volume: 61, Issue:8	2022
Novel Regimens of Bedaquiline-Pyrazinamide Combined with Moxifloxacin, Rifabutin, Delamanid and/or OPC-167832 in Murine Tuberculosis Models. Antimicrobial agents and chemotherapy, , 04-19, Volume: 66, Issue:4	2022
Evaluating the effect of clofazimine against Mycobacterium tuberculosis given alone or in combination with pretomanid, bedaquiline or linezolid. International journal of antimicrobial agents, , Volume: 59, Issue:2	2022
Effect of Natural Phenolics on Pharmacokinetic Modulation of Bedaquiline in Rat to Assess the Likelihood of Potential Food-Drug Interaction. Journal of agricultural and food chemistry, , Feb-05, Volume: 68, Issue:5	2020
No in vitro synergistic effect of bedaquiline combined with fluoroquinolones, linezolid, and clofazimine against extensively drug-resistant tuberculosis. Diagnostic microbiology and infectious disease, , Volume: 94, Issue:4	2019
Assessment of preclinical drug interactions of bedaquiline by a highly sensitive LC-ESI-MS/MS based bioanalytical method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, , Apr-01, Volume: 1112	2019
Drug-drug interactions between bedaquiline and the antiretrovirals lopinavir/ritonavir and nevirapine in HIV-infected patients with drug-resistant TB. The Journal of antimicrobial chemotherapy, , Volume: 71, Issue:4	2016
Bedaquiline: a review of human pharmacokinetics and drug-drug interactions. The Journal of antimicrobial chemotherapy, , Volume: 69, Issue:9	2014
Speciation analysis of bromine-containing drug metabolites in feces samples from a human in vivo study by means of HPLC/ICP-MS combined with on-line isotope dilution. Analytical and bioanalytical chemistry, , Volume: 402, Issue:1	2012
Synergistic activity of R207910 combined with pyrazinamide against murine tuberculosis. Antimicrobial agents and chemotherapy, , Volume: 51, Issue:3	2007