Compounds > cay 10580
Page last updated: 2024-08-03 15:05:55

cay 10580

Description

CAY 10580: a E-prostanoid EP4 receptor agonist [MeSH]

2-(3-hydroxyoctyl)-5-oxo-1-pyrrolidineheptanoic acid : A pyrrolidin-2-one substituted by 6-carboxyhexyl and 3-hydroxyoctyl groups at positions 1 and 2, respectively. It is a potent prostaglandin EP4 receptor agonist (Ki=35 nM). [CHeBI]

Cross-References

ID SourceID
PubMed CID44269516
CHEMBL ID15096
CHEBI ID194210
MeSH IDM0562113

Synonyms (16)

Synonym
7-[2-(3-hydroxy-octyl)-5-oxo-pyrrolidin-1-yl]-heptanoic acid
bdbm50125403
CHEMBL15096 ,
2-(3-hydroxyoctyl)-5-oxo-1-pyrrolidineheptanoic acid
cay 10580
CHEBI:194210
64054-40-6
7-[2-(3-hydroxyoctyl)-5-oxopyrrolidin-1-yl]heptanoic acid
cay-10580
cay10580
DTXSID10658096
AKOS027288931
7-(2-(3-hydroxyoctyl)-5-oxopyrrolidin-1-yl)heptanoic acid
CS-0110313
HY-135259
mfcd11976917

Roles (1)

RoleDescription
prostaglandin receptor agonistAn agonist that binds to and activates prostaglandin receptors.

Drug Classes (3)

ClassDescription
pyrrolidin-2-onesA pyrrolidinone in which the oxo group is at position 2 of the pyrrolidine ring.
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Thromboxane A2 receptor Homo sapiens (human)Ki13.0000AID161215
Prostaglandin E2 receptor EP1 subtypeHomo sapiens (human)Ki13.0000AID160687
Prostaglandin E2 receptor EP4 subtypeHomo sapiens (human)Ki0.0350AID161075
Prostaglandin F2-alpha receptorHomo sapiens (human)Ki13.0000AID160705
Prostaglandin E2 receptor EP3 subtypeHomo sapiens (human)Ki2.0000AID160689
Prostaglandin E2 receptor EP2 subtypeHomo sapiens (human)Ki3.0000AID160688
Prostacyclin receptorHomo sapiens (human)Ki13.0000AID160763
Prostaglandin D2 receptorHomo sapiens (human)Ki13.0000AID160535

Bioassays (14)

Assay IDTitleYearJournalArticle
AID160689Binding affinity towards EP3 receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID161075Binding affinity towards EP4 receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID1146116Binding affinity to prostaglandin receptor in Charles River CD-1 mouse ovary assessed as increase in cAMP accumulation using [8-14C]adenine at 100 ug/ml after 30 mins relative to control1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
AID160688Binding affinity towards EP2 receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID1146113Dissociation constant, pKa of the compound1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
AID1146115Binding affinity to prostaglandin receptor in Charles River CD-1 mouse ovary assessed as increase in cAMP accumulation using [8-14C]adenine at 25 ug/ml after 30 mins relative to control1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
AID161215Binding affinity towards TP receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID1146112Retardation factor, Rf of the compound1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
AID160763Binding affinity towards IP receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID160705Binding affinity towards FP receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID160535Binding affinity towards DP receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID1146114Binding affinity to prostaglandin receptor in Charles River CD-1 mouse ovary assessed as increase in cAMP accumulation using [8-14C]adenine at 1 ug/ml after 30 mins relative to control1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
AID160687Binding affinity towards EP1 receptor expressed in HEK293 ebna cells recombinantly expressing the corresponding human prostanoid cDNAs2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
ISSN: 0960-894X		Discovery of a potent and selective agonist of the prostaglandin EP4 receptor.
AID1146117Displacement of [3H-PGE1] from Sprague-Dawley rat kidney prostaglandin receptor after 60 mins by scintillation counting analysis1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
ISSN: 0022-2623		Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (11.11)18.7374
1990's0 (0.00)18.2507
2000's1 (11.11)29.6817
2010's7 (77.78)24.3611
2020's0 (0.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
pyrrolidonecarboxylic acid
0
oxoproline;
pyrrolidin-2-ones;
pyrrolidinemonocarboxylic acid		human metabolite00low000000
aniracetam
0
N-acylpyrrolidine;
pyrrolidin-2-ones		00low000000
doxapram
0
morpholines;
pyrrolidin-2-ones		central nervous system stimulant00low000000
rolipram
0
pyrrolidin-2-onesantidepressant;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor		00low000000
n-vinyl-2-pyrrolidinone
0
pyrrolidin-2-ones00low000000
2-pyrrolidone
0
pyrrolidin-2-onesmetabolite;
polar solvent		00low000000
n-methylpyrrolidone
0
lactam;
N-alkylpyrrolidine;
pyrrolidin-2-ones		polar aprotic solvent00low000000
1-lauryl-2-pyrrolidone
0
pyrrolidin-2-onesepitope00low000000
fradafiban
0
carboxamidine;
monocarboxylic acid;
pyrrolidin-2-ones		platelet glycoprotein-IIb/IIIa receptor antagonist00low000000
hydroxycotinine
0
N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		00low000000
1-[4-carboxy-2-(3-pentylamino)phenyl]-5,5-bis(hydroxymethyl)pyrrolidin-2-one
0
benzoic acids;
primary alcohol;
pyrrolidin-2-ones;
secondary amino compound		00low000000
cotinine
0
N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite		00low000000
levetiracetam
0
pyrrolidin-2-onesanticonvulsant;
environmental contaminant;
xenobiotic		00low000000
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
0
benzyl ester;
isoxazoles;
pyrrolidin-2-ones;
tripeptide		anticoronaviral agent;
antiviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor		00low000000
ik 682
0
hydroxamic acid;
pyrrolidin-2-ones;
quinolines		00low000000
3,3-diethyl-2-pyrrolidinone
0
pyrrolidin-2-onesanticonvulsant;
geroprotector		00low000000
rolapitant
0
azaspiro compound;
ether;
organofluorine compound;
piperidines;
pyrrolidin-2-ones		antiemetic;
neurokinin-1 receptor antagonist		00low000000
vibrioferrin
0
carboxylic ester;
N-acyl hemiaminal;
pyrrolidin-2-ones;
tertiary alcohol;
tricarboxylic acid		marine metabolite;
siderophore		00low000000
PF-00835231
0
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		00low000000
ivosidenib
0
cyanopyridine;
monochlorobenzenes;
organofluorine compound;
pyrrolidin-2-ones;
secondary carboxamide;
tertiary carboxamide		antineoplastic agent;
EC 1.1.1.42 (isocitrate dehydrogenase) inhibitor		00low000000
N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide
0
aldehyde;
indolecarboxamide;
oligopeptide;
pyrrolidin-2-ones;
secondary carboxamide		anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor		00low000000
3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
0
aldehyde;
indolecarboxamide;
monofluorobenzenes;
oligopeptide;
pyrrolidin-2-ones;
secondary carboxamide		anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor		00low000000
PF-07304814
0
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		00low000000
nirmatrelvir
0
azabicyclohexane;
nitrile;
organofluorine compound;
pyrrolidin-2-ones;
pyrrolidinecarboxamide;
secondary carboxamide;
tertiary carboxamide		anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor		00low000000
fluorescite
0
benzoic acids;
cyclic ketone;
hydroxy monocarboxylic acid;
organic heterotricyclic compound;
phenols;
xanthene dye		fluorescent dye;
radioopaque medium		00low000000
1-hydroxy-2-naphthoic acid
0
hydroxy monocarboxylic acid;
naphthoic acid;
naphthols		bacterial xenobiotic metabolite;
fungal xenobiotic metabolite		00low000000
shikimic acid
0
alpha,beta-unsaturated monocarboxylic acid;
cyclohexenecarboxylic acid;
hydroxy monocarboxylic acid		Escherichia coli metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		00low000000
glycyrrhetinic acid
0
cyclic terpene ketone;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		immunomodulator;
plant metabolite		00low000000
phloretic acid
0
hydroxy monocarboxylic acidplant metabolite00low000000
oleanolic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite00low000000
2-hydroxyphenylacetic acid
0
hydroxy monocarboxylic acid;
phenols		human metabolite;
mouse metabolite		00low000000
pravastatin
0
3-hydroxy carboxylic acid;
carbobicyclic compound;
carboxylic ester;
hydroxy monocarboxylic acid;
secondary alcohol;
statin (semi-synthetic)		anticholesteremic drug;
environmental contaminant;
metabolite;
xenobiotic		00low000000
ursolic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite		00low000000
betulinic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite		00low000000
platanic acid
0
hydroxy monocarboxylic acid;
methyl ketone;
pentacyclic triterpenoid		anti-HIV agent;
metabolite		00low000000
dihydrobetulinic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
antileishmanial agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
metabolite		00low000000
cyclobutyrol
0
hydroxy monocarboxylic acidbile therapy drug00low000000
pulsatilla saponin a
0
disaccharide derivative;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid;
triterpenoid saponin		anti-inflammatory agent;
plant metabolite		00low000000
arjunolic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite		00low000000
indole-3-lactic acid
0
hydroxy monocarboxylic acid;
indol-3-yl carboxylic acid		human metabolite00low000000
delta(9)-tetrahydrocannabinolic acid
0
benzochromene;
diterpenoid;
hydroxy monocarboxylic acid;
phytocannabinoid;
polyketide		anti-inflammatory agent;
biomarker;
metabolite;
neuroprotective agent		00low000000
quillaic acid
0
aldehyde;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory agent;
metabolite		00low000000
3-chloro-4-hydroxyphenylacetic acid
0
hydroxy monocarboxylic acid;
monochlorobenzenes;
phenols		mammalian metabolite00low000000
3,7,12-trihydroxycoprostanic acid
0
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
cholestanoic acid;
hydroxy monocarboxylic acid		human metabolite00low000000
3,7,12-trihydroxycholestan-26-oic acid
0
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
hydroxy monocarboxylic acid;
steroid acid		human metabolite00low000000
leukodopachrome
0
hydroxy monocarboxylic acid;
indoles		metabolite00low000000
maprounic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		HIV-1 reverse transcriptase inhibitor;
plant metabolite		00low000000
anacardic acid
0
hydroxy monocarboxylic acid;
hydroxybenzoic acid		anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
apoptosis inducer;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
neuroprotective agent;
plant metabolite		00low000000
3-o-(alpha-l-arabinopyranosyl)hederagenin
0
alpha-L-arabinopyranoside;
hydroxy monocarboxylic acid;
monosaccharide derivative;
pentacyclic triterpenoid;
triterpenoid saponin		plant metabolite00low000000
16beta,17-dihydroxy-ent-kaurane-19-oic acid
0
bridged compound;
diol;
ent-kaurane diterpenoid;
hydroxy monocarboxylic acid;
primary alcohol;
tertiary alcohol		anti-HIV agent;
metabolite		00low000000
euscaphic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid;
triol		plant metabolite00low000000
23-hydroxytormentic acid
0
hydroxy monocarboxylic acid;
pentacyclic triterpenoid;
tetrol		anti-inflammatory agent;
plant metabolite		00low000000
3,7,12,24-tetrahydroxycholestanoic acid
0
12alpha-hydroxy steroid;
24-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
hydroxy monocarboxylic acid		bile acid metabolite00low000000
carboprost
0
hydroxy monocarboxylic acidabortifacient;
oxytocic		00low000000
17-phenyltrinorprostaglandin e2
0
alicyclic ketone;
beta-hydroxy ketone;
hydroxy monocarboxylic acid;
olefinic compound;
oxo monocarboxylic acid;
prostanoid;
secondary alcohol		human metabolite;
prostaglandin receptor agonist		00low000000
20-hydroxy-5,8,11,14-eicosatetraenoic acid
0
HETE;
hydroxy monocarboxylic acid		human metabolite;
mouse metabolite		00low000000
fluprostenol
0
(trifluoromethyl)benzenes;
hydroxy monocarboxylic acid;
prostaglandins Falpha		abortifacient;
antiglaucoma drug;
antihypertensive agent;
female contraceptive drug;
prostaglandin receptor agonist		00low000000
thermozymocidin
0
alpha-amino fatty acid;
hydroxy monocarboxylic acid;
non-proteinogenic alpha-amino acid;
sphingoid		antifungal agent;
antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor;
fungal metabolite;
immunosuppressive agent		00low000000
phxa 85
0
hydroxy monocarboxylic acid;
prostaglandins Falpha		antiglaucoma drug;
antihypertensive agent;
EC 4.2.1.1 (carbonic anhydrase) inhibitor		00low000000
hydroxyibuprofen
0
hydroxy monocarboxylic acid;
tertiary alcohol		drug metabolite00low000000
triptotriterpenic acid a
0
diol;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite00low000000
etnangien
0
hydroxy monocarboxylic acid;
macrolide antibiotic		antibacterial agent;
metabolite		00low000000
nbi 31772
0
aromatic ketone;
benzenediols;
hydroxy monocarboxylic acid;
isoquinolines;
tetrol		insulin-like growth factor-binding protein inhibitor00low000000
monoisopropanolamine
0
amino alcohol;
secondary alcohol		Escherichia coli metabolite00low000000
2,3-butylene glycol
0
butanediol;
glycol;
secondary alcohol		00low000000
isocitric acid
0
secondary alcohol;
tricarboxylic acid		fundamental metabolite00low000000
menthol
0
p-menthane monoterpenoid;
secondary alcohol		volatile oil component00low000000
alprenolol
0
secondary alcohol;
secondary amino compound		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
sympatholytic agent		00low000000
bisoprolol
0
secondary alcohol;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
sympatholytic agent		00low000000
carteolol
0
quinolone;
secondary alcohol		anti-arrhythmia drug;
antiglaucoma drug;
antihypertensive agent;
beta-adrenergic antagonist;
sympatholytic agent		00low000000
carvedilol
0
carbazoles;
secondary alcohol;
secondary amino compound		alpha-adrenergic antagonist;
antihypertensive agent;
beta-adrenergic antagonist;
cardiovascular drug;
vasodilator agent		00low000000
cgp 12177
0
aromatic ether;
benzimidazoles;
secondary alcohol;
secondary amino compound		beta-adrenergic antagonist00low000000
chlorphenesin carbamate
0
carbamate ester;
monochlorobenzenes;
secondary alcohol		muscle relaxant00low000000
cyclandelate
0
carboxylic ester;
secondary alcohol		vasodilator agent00low000000
1-phenyl-2-palmitoylamino-3-morpholino-1-propanol
0
benzyl alcohols;
fatty amide;
morpholines;
secondary alcohol;
tertiary amino compound		00low000000
berotek
0
resorcinols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
sympathomimetic agent;
tocolytic agent		00low000000
formoterol fumarate
0
formamides;
phenols;
phenylethanolamines;
secondary alcohol;
secondary amino compound		00low000000
2-propanol
0
secondary alcohol;
secondary fatty alcohol		protic solvent00low000000
isoproterenol
0
catechols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
sympathomimetic agent		00low000000
labetalol
0
benzamides;
benzenes;
phenols;
primary carboxamide;
salicylamides;
secondary alcohol;
secondary amino compound		00low000000
mefloquine hydrochloride
0
organofluorine compound;
piperidines;
quinolines;
secondary alcohol		00low000000
metaproterenol
0
aralkylamino compound;
phenylethanolamines;
resorcinols;
secondary alcohol;
secondary amino compound		00low000000
methocarbamol
0
aromatic ether;
carbamate ester;
secondary alcohol		00low000000
metoprolol
0
aromatic ether;
propanolamine;
secondary alcohol;
secondary amino compound		antihypertensive agent;
beta-adrenergic antagonist;
environmental contaminant;
geroprotector;
xenobiotic		00low000000
midodrine
0
amino acid amide;
aromatic ether;
secondary alcohol		alpha-adrenergic agonist;
prodrug;
sympathomimetic agent;
vasoconstrictor agent		00low000000
practolol
0
acetamides;
ethanolamines;
propanolamine;
secondary alcohol;
secondary amino compound		anti-arrhythmia drug;
beta-adrenergic antagonist		00low000000
propafenone
0
aromatic ketone;
secondary alcohol;
secondary amino compound		anti-arrhythmia drug00low000000
salmeterol xinafoate
0
ether;
phenols;
primary alcohol;
secondary alcohol;
secondary amino compound		00low000000
sotalol
0
ethanolamines;
secondary alcohol;
secondary amino compound;
sulfonamide		anti-arrhythmia drug;
beta-adrenergic antagonist;
environmental contaminant;
xenobiotic		00low000000
cycloheximide
0
antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor		00low000000
2-butanol
0
secondary alcohol00low000000
pseudoephedrine
0
phenylethanolamines;
secondary alcohol;
secondary amino compound		anti-asthmatic drug;
bronchodilator agent;
central nervous system drug;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		00low000000
benzohydrol
0
benzyl alcohols;
secondary alcohol		bacterial xenobiotic metabolite;
human urinary metabolite;
human xenobiotic metabolite;
rat metabolite		00low000000
1,3-dichloro-2-propanol
0
organochlorine compound;
secondary alcohol		cross-linking reagent;
protic solvent		00low000000
ethyl lactate
0
ethyl ester;
lactate ester;
secondary alcohol		metabolite00low000000
12-hydroxy stearic acid
0
hydroxyoctadecanoic acid;
secondary alcohol		bacterial xenobiotic metabolite;
plant metabolite		00low000000
cyclohexanol
0
cyclohexanols;
secondary alcohol		solvent00low000000
diisopropanolamine
0
aminodiol;
secondary alcohol;
secondary amino compound		buffer;
emulsifier;
surfactant		00low000000
3,3,5-trimethylcyclohexanol
0
cyclohexanols;
secondary alcohol		EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor00low000000
2-methyl-5-(1-methylethenyl)cyclohexanol
0
p-menthane monoterpenoid;
secondary alcohol		acaricide;
plant metabolite;
volatile oil component		00low000000
2-hexanol
0
hexanol;
secondary alcohol		human metabolite;
plant metabolite;
semiochemical		00low000000
2-nonanol
0
nonanol;
secondary alcohol		bacterial metabolite;
flavouring agent;
pheromone;
plant metabolite;
rat metabolite;
volatile oil component		00low000000
ethyl mandelate
0
ethyl ester;
secondary alcohol		00low000000
hexafluoroisopropanol
0
organofluorine compound;
secondary alcohol		drug metabolite00low000000
3-quinuclidinol
0
quinuclidines;
secondary alcohol;
tertiary amine		00low000000
2-undecanol
0
secondary alcohol;
undecanol		animal metabolite;
flavouring agent;
pheromone;
plant metabolite;
volatile oil component		00low000000
spectinomycin
0
cyclic acetal;
cyclic hemiketal;
cyclic ketone;
pyranobenzodioxin;
secondary alcohol;
secondary amino compound		antibacterial drug;
antimicrobial agent;
bacterial metabolite		00low000000
2,5-hexanediol
0
glycol;
secondary alcohol		00low000000
2-octanol
0
octanol;
secondary alcohol		plant metabolite;
volatile oil component		00low000000
sulcatol
0
secondary alcoholpheromone00low000000
1-indanol
0
aromatic alcohol;
indanes;
secondary alcohol		xenobiotic00low000000
helenalin
0
cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite		00low000000
colterol
0
catechols;
ethanolamines;
secondary alcohol;
secondary amino compound;
triol		anti-asthmatic drug;
beta-adrenergic agonist;
bronchodilator agent		00low000000
ornidazole
0
C-nitro compound;
imidazoles;
organochlorine compound;
secondary alcohol		antiamoebic agent;
antibacterial drug;
antiinfective agent;
antiprotozoal drug;
antitrichomonal drug;
epitope		00low000000
1-chloro-2-propanol
0
organochlorine compound;
secondary alcohol		00low000000
du-21220
0
benzyl alcohols;
polyphenol;
secondary alcohol;
secondary amino compound		00low000000
bitolterol
0
carboxylic ester;
diester;
ethanolamines;
secondary alcohol;
secondary amino compound		anti-asthmatic drug;
beta-adrenergic agonist;
bronchodilator agent;
prodrug		00low000000
diisopropanolnitrosamine
0
diol;
nitrosamine;
secondary alcohol		carcinogenic agent00low000000
triadimenol
0
aromatic ether;
conazole fungicide;
hemiaminal ether;
monochlorobenzenes;
secondary alcohol;
triazole fungicide		antifungal agrochemical;
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor;
xenobiotic metabolite		00low000000
st 1059
0
aromatic ether;
primary amino compound;
secondary alcohol		alpha-adrenergic agonist;
sympathomimetic agent;
vasoconstrictor agent		00low000000
ractopamine
0
benzyl alcohols;
polyphenol;
secondary alcohol;
secondary amino compound		00low000000
ranolazine
0
aromatic amide;
monocarboxylic acid amide;
monomethoxybenzene;
N-alkylpiperazine;
secondary alcohol		00low000000
lisofylline
0
dimethylxanthine;
secondary alcohol		00low000000
esmolol
0
aromatic ether;
ethanolamines;
methyl ester;
secondary alcohol;
secondary amino compound		00low000000
eliprodil
0
monochlorobenzenes;
monofluorobenzenes;
piperidines;
secondary alcohol;
tertiary amino compound		00low000000
nelfinavir
0
aryl sulfide;
benzamides;
organic heterobicyclic compound;
phenols;
secondary alcohol;
tertiary amino compound		antineoplastic agent;
HIV protease inhibitor		00low000000
calanolide a
0
cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite		00low000000
cephalotaxine
0
benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
cyclic acetal;
enol ether;
organic heteropentacyclic compound;
secondary alcohol;
tertiary amino compound		00low000000
16-hydroxytestosterone
0
16alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid;
C19-steroid;
diol;
secondary alcohol		androgen00low000000
nebivolol
0
chromanes;
diol;
organofluorine compound;
secondary alcohol;
secondary amino compound		00low000000
secnidazole
0
C-nitro compound;
imidazoles;
secondary alcohol		epitope00low000000
zaluzanin C
0
gamma-lactone;
guaiane sesquiterpenoid;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
metabolite		00low000000
beta-amyrin
0
pentacyclic triterpenoid;
secondary alcohol		Aspergillus metabolite;
plant metabolite		00low000000
alpha-amyrin
0
pentacyclic triterpenoid;
secondary alcohol		00low000000
mandelamide
0
benzyl alcohols;
monocarboxylic acid amide;
secondary alcohol		00low000000
fluoren-9-ol
0
hydroxyfluorenes;
secondary alcohol		animal metabolite00low000000
loganin
0
beta-D-glucoside;
cyclopentapyran;
enoate ester;
iridoid monoterpenoid;
methyl ester;
monosaccharide derivative;
secondary alcohol		anti-inflammatory agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
EC 3.4.23.46 (memapsin 2) inhibitor;
neuroprotective agent;
plant metabolite		00low000000
1-cyano-2-hydroxy-3-butene
0
secondary alcohol00low000000
bitertanol
0
aromatic ether;
biphenyls;
secondary alcohol;
triazoles		00low000000
taraxerol
0
pentacyclic triterpenoid;
secondary alcohol		metabolite00low000000
4,4'-oxydi-2-butanol
0
secondary alcohol00low000000
lactamide
0
monocarboxylic acid amide;
secondary alcohol		00low000000
sporidesmin
0
aromatic ether;
cyclic ketone;
diketone;
organic disulfide;
organic heteropentacyclic compound;
organochlorine compound;
secondary alcohol;
tertiary alcohol;
tertiary amino compound		mycotoxin;
Wnt signalling activator		00low000000
erythrodiol
0
diol;
pentacyclic triterpenoid;
primary alcohol;
secondary alcohol		plant metabolite00low000000
6,6-dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol
0
carbobicyclic compound;
pinane monoterpenoid;
secondary alcohol		GABA modulator;
mouse metabolite;
plant metabolite;
volatile oil component		00low000000
4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol
0
nitrosamine;
pyridines;
secondary alcohol		biomarker;
carcinogenic agent;
human urinary metabolite		00low000000
4-hydroxydebrisoquin
0
carboxamidine;
isoquinolines;
secondary alcohol		metabolite00low000000
tabtoxin
0
dipeptide;
L-threonine derivative;
monobactam;
secondary alcohol		bacterial metabolite;
toxin		00low000000
florfenicol
0
organochlorine compound;
organofluorine compound;
secondary alcohol;
secondary carboxamide;
sulfone		antimicrobial agent00low000000
megestrol acetate
0
bridged compound;
organic heterotetracyclic compound;
secondary alcohol;
sesquiterpene lactone;
spiro compound;
tertiary alcohol;
tetrol		GABA antagonist;
neurotoxin;
phytogenic insecticide;
plant metabolite		00low000000
paliperidone
0
1,2-benzoxazoles;
heteroarylpiperidine;
organofluorine compound;
pyridopyrimidine;
secondary alcohol		00low000000
taraxasterol
0
pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory agent;
metabolite		00low000000
cubebin
0
benzodioxoles;
cyclic acetal;
lactol;
lignan;
secondary alcohol		analgesic;
anti-inflammatory agent;
antimicrobial agent;
histamine antagonist;
plant metabolite;
trypanocidal drug		00low000000
bw 245c
0
imidazolidine-2,4-dione;
monocarboxylic acid;
secondary alcohol		00low000000
conduritol b
0
cyclitol;
secondary alcohol;
tetrol		00low000000
withanolide d
0
20-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
enone;
epoxy steroid;
ergostanoid;
secondary alcohol;
tertiary alcohol;
withanolide		antineoplastic agent00low000000
ml 236a
0
2-pyranones;
carbobicyclic compound;
hexahydronaphthalenes;
polyketide;
secondary alcohol		antiatherosclerotic agent;
anticholesteremic drug;
antilipemic drug;
antimicrobial agent;
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor;
fungal metabolite		00low000000
corynoline
0
benzophenanthridine alkaloid;
cyclic acetal;
isoquinolines;
organic heterohexacyclic compound;
secondary alcohol		antineoplastic agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
hepatoprotective agent;
metabolite		00low000000
fumagillol
0
secondary alcohol;
sesquiterpenoid;
spiro-epoxide		antimicrobial agent00low000000
lupeol
0
pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite		00low000000
withaferin a
0
27-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
enone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		antineoplastic agent;
apoptosis inducer		00low000000
2-hydroxypropylphosphonic acid
0
phosphonic acids;
secondary alcohol		mouse metabolite00low000000
xv 638
0
1,3-thiazoles;
benzamides;
diazepanone;
diol;
secondary alcohol;
secondary carboxamide;
ureas		HIV protease inhibitor00low000000
hippeastrine
0
delta-lactone;
indole alkaloid;
organic heteropentacyclic compound;
secondary alcohol		antineoplastic agent;
metabolite		00low000000
decursinol
0
cyclic ether;
delta-lactone;
organic heterotricyclic compound;
secondary alcohol		analgesic;
antineoplastic agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
metabolite		00low000000
lactucin
0
azulenofuran;
cyclic terpene ketone;
enone;
primary alcohol;
secondary alcohol;
sesquiterpene lactone		antimalarial;
plant metabolite;
sedative		00low000000
yersiniabactin
0
monocarboxylic acid;
phenols;
secondary alcohol;
thiazolidines		bacterial metabolite;
siderophore		00low000000
prostaglandin h2
0
olefinic compound;
oxylipin;
prostaglandins H;
secondary alcohol		mouse metabolite00low000000
(north)-methanocarbathymidine
0
C-glycosyl pyrimidine;
carbobicyclic compound;
primary alcohol;
pyrimidone;
secondary alcohol		00low000000
mupirocin
0
alpha,beta-unsaturated carboxylic ester;
epoxide;
monocarboxylic acid;
oxanes;
secondary alcohol;
triol		antibacterial drug;
bacterial metabolite;
protein synthesis inhibitor		00low000000
costatolide
0
cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite		00low000000
pf 1163a
0
aromatic ether;
lactam;
macrolide antibiotic;
secondary alcohol		antifungal agent;
Penicillium metabolite		00low000000
tiamulin
0
carbotricyclic compound;
carboxylic ester;
cyclic ketone;
organic sulfide;
secondary alcohol;
semisynthetic derivative;
tertiary amino compound;
tetracyclic diterpenoid		antibacterial drug00low000000
wiskostatin
0
carbazoles;
organobromine compound;
secondary alcohol;
tertiary amino compound		00low000000
galanal a
0
secondary alcohol00low000000
brl 15572
0
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
secondary alcohol		geroprotector;
serotonergic antagonist		00low000000
australifungin
0
carbobicyclic compound;
enol;
enone;
secondary alcohol		antifungal agent;
EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor;
HIV-1 integrase inhibitor;
metabolite		00low000000
bryostatin 1
0
acetate ester;
bryostatins;
cyclic hemiketal;
enoate ester;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol		alpha-secretase activator;
anti-HIV-1 agent;
antineoplastic agent;
marine metabolite;
protein kinase C agonist		00low000000
cholecalciferol
0
D3 vitamins;
hydroxy seco-steroid;
seco-cholestane;
secondary alcohol;
steroid hormone		geroprotector;
human metabolite		00low000000
leukotriene e4
0
amino dicarboxylic acid;
L-cysteine thioether;
leukotriene;
non-proteinogenic L-alpha-amino acid;
secondary alcohol		00low000000
9-deoxy-9,10-didehydro-12,13-didehydro-13,14-dihydroprostaglandin d2
0
prostaglandins J;
secondary alcohol		antineoplastic agent;
antiviral agent		00low000000
previtamin d(3)
0
D3 vitamins;
hydroxy seco-steroid;
seco-cholestane;
secondary alcohol		human metabolite00low000000
azadirachtin
0
acetate ester;
azadirachtin;
cyclic hemiketal;
enoate ester;
epoxide;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol;
tertiary alcohol		hepatoprotective agent00low000000
strigol
0
indenofuran;
secondary alcohol;
strigolactone		00low000000
eupatolide
0
gamma-lactone;
germacranolide;
homoallylic alcohol;
secondary alcohol		antineoplastic agent;
plant metabolite		00low000000
l 683590
0
ether;
lactol;
macrolide;
secondary alcohol		antifungal agent;
bacterial metabolite;
immunosuppressive agent		00low000000
2,3-dinor-6-ketoprostaglandin f1alpha
0
4-oxo monocarboxylic acid;
prostanoid;
secondary alcohol		metabolite00low000000
8-isoprostaglandin e2
0
cyclic ketone;
diol;
prostanoid;
secondary alcohol		bronchoconstrictor agent;
human metabolite;
rat metabolite;
vasoconstrictor agent		00low000000
sirolimus
0
antibiotic antifungal drug;
cyclic acetal;
cyclic ketone;
ether;
macrolide lactam;
organic heterotricyclic compound;
secondary alcohol		antibacterial drug;
anticoronaviral agent;
antineoplastic agent;
bacterial metabolite;
geroprotector;
immunosuppressive agent;
mTOR inhibitor		00low000000
calcipotriene
0
cyclopropanes;
hydroxy seco-steroid;
seco-cholestane;
secondary alcohol;
triol		antipsoriatic;
drug allergen		00low000000
bay u9773
0
benzoic acids;
dicarboxylic acid;
organic sulfide;
polyunsaturated fatty acid;
secondary alcohol		leukotriene antagonist00low000000
iloprost
0
carbobicyclic compound;
monocarboxylic acid;
secondary alcohol		platelet aggregation inhibitor;
vasodilator agent		00low000000
andrographolide
0
carbobicyclic compound;
gamma-lactone;
labdane diterpenoid;
primary alcohol;
secondary alcohol		anti-HIV agent;
anti-inflammatory drug;
antineoplastic agent;
metabolite		00low000000
oridonin
0
cyclic hemiketal;
enone;
ent-kaurane diterpenoid;
organic heteropentacyclic compound;
secondary alcohol		angiogenesis inhibitor;
anti-asthmatic agent;
antibacterial agent;
antineoplastic agent;
apoptosis inducer;
plant metabolite		00low000000
lasalocid
0
beta-hydroxy ketone;
monocarboxylic acid;
monohydroxybenzoic acid;
oxanes;
oxolanes;
polyether antibiotic;
secondary alcohol;
tertiary alcohol		bacterial metabolite;
coccidiostat;
ionophore		00low000000
pederin
0
cyclic ketal;
diol;
oxanes;
polyketide;
secondary alcohol;
secondary carboxamide		antimitotic;
antineoplastic agent;
bacterial metabolite;
vesicant		00low000000
streptogramin a
0
1,3-oxazoles;
cyclic ketone;
enamide;
lactam;
macrolide antibiotic;
macrolide;
pyrroline;
secondary alcohol;
secondary carboxamide;
tertiary carboxamide		antibacterial drug;
Mycoplasma genitalium metabolite		00low000000
benanomicin b
0
aromatic ether;
disaccharide derivative;
L-alanine derivative;
polyketide;
polyphenol;
pradimicin;
secondary alcohol		00low000000
pradimicin b
0
aromatic ether;
L-alanine derivative;
monosaccharide derivative;
polyketide;
polyphenol;
pradimicin;
secondary alcohol		00low000000
poricoic acid a
0
dicarboxylic acid;
secondary alcohol;
tricyclic triterpenoid		fungal metabolite00low000000
poricoic acid g
0
dicarboxylic acid;
secondary alcohol;
tricyclic triterpenoid		fungal metabolite00low000000
pradimicin a
0
aromatic ether;
carboxylic acid;
disaccharide derivative;
L-alanine derivative;
p-quinones;
polyphenol;
pradimicin;
secondary alcohol		00low000000
l 685458
0
carbamate ester;
monocarboxylic acid amide;
peptide;
secondary alcohol		EC 3.4.23.46 (memapsin 2) inhibitor;
peptidomimetic		00low000000
ici 118551
0
aromatic ether;
indanes;
secondary alcohol;
secondary amino compound		beta-adrenergic antagonist00low000000
uniconazole
0
monochlorobenzenes;
secondary alcohol;
triazoles		00low000000
diniconazole
0
dichlorobenzene;
olefinic compound;
secondary alcohol;
triazoles		00low000000
lumefantrine
0
fluorenes;
monochlorobenzenes;
secondary alcohol;
tertiary amine		antimalarial00low000000
bryostatin 2
0
bryostatins;
cyclic hemiketal;
enoate ester;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol		antineoplastic agent;
marine metabolite;
protein kinase C agonist		00low000000
everolimus
0
cyclic acetal;
cyclic ketone;
ether;
macrolide lactam;
primary alcohol;
secondary alcohol		anticoronaviral agent;
antineoplastic agent;
geroprotector;
immunosuppressive agent;
mTOR inhibitor		00low000000
terpestacin
0
secondary alcohol00low000000
chaetoviridin a
0
azaphilone;
beta-hydroxy ketone;
enone;
gamma-lactone;
organic heterotricyclic compound;
organochlorine compound;
secondary alcohol		antifungal agent;
Chaetomium metabolite		00low000000
ro 25-6981
0
benzenes;
phenols;
piperidines;
secondary alcohol;
tertiary amino compound		anticonvulsant;
antidepressant;
neuroprotective agent;
NMDA receptor antagonist		00low000000
beraprost
0
enyne;
monocarboxylic acid;
organic heterotricyclic compound;
secondary alcohol;
secondary allylic alcohol		anti-inflammatory agent;
antihypertensive agent;
platelet aggregation inhibitor;
prostaglandin receptor agonist;
vasodilator agent		00low000000
yunaconitine
0
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		00low000000
laulimalide
0
carboxylic ester;
epoxide;
macrolide;
secondary alcohol;
secondary allylic alcohol		animal metabolite;
antimitotic;
antineoplastic agent;
marine metabolite;
microtubule-stabilising agent		00low000000
indacaterol
0
indanes;
monohydroxyquinoline;
quinolone;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent		00low000000
grayanotoxin i
0
acetate ester;
pentol;
secondary alcohol;
tertiary alcohol;
tetracyclic diterpenoid		antihypertensive agent;
metabolite;
neuromuscular agent;
phytotoxin		00low000000
fr 148083
0
aromatic ether;
macrolide;
phenols;
secondary alcohol;
secondary alpha-hydroxy ketone		antibacterial agent;
antineoplastic agent;
metabolite;
NF-kappaB inhibitor		00low000000
tmc-95a
0
indoles;
lactam;
macrocycle;
phenols;
secondary alcohol;
tertiary alcohol		antimicrobial agent;
antineoplastic agent;
bacterial metabolite;
fungal metabolite;
proteasome inhibitor		00low000000
solabegron
0
carboxybiphenyl;
monochlorobenzenes;
secondary alcohol;
secondary amino compound;
substituted aniline		beta-adrenergic agonist00low000000
monacolin j
0
2-pyranones;
carbobicyclic compound;
hexahydronaphthalenes;
polyketide;
secondary alcohol		antimicrobial agent;
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor;
fungal metabolite		00low000000
ustiloxin b
0
aromatic ether;
heterodetic cyclic peptide;
macrocycle;
phenols;
secondary alcohol;
secondary carboxamide;
sulfoxide		Aspergillus metabolite;
microtubule-destabilising agent;
mycotoxin		00low000000
glutinol
0
pentacyclic triterpenoid;
secondary alcohol		00low000000
3-epi-fagomine
0
amino monosaccharide;
hydroxypiperidine;
primary alcohol;
secondary alcohol;
secondary amino compound;
triol		EC 3.2.1.10 (oligo-1,6-glucosidase) inhibitor;
EC 3.2.1.23 (beta-galactosidase) inhibitor;
plant metabolite		00low000000
ly 411575
0
dibenzoazepine;
difluorobenzene;
lactam;
secondary alcohol		EC 3.4.23.46 (memapsin 2) inhibitor00low000000
manassantin b
0
benzodioxoles;
dimethoxybenzene;
lignan;
oxolanes;
secondary alcohol		antineoplastic agent;
metabolite		00low000000
tmc-95b
0
indoles;
lactam;
macrocycle;
phenols;
secondary alcohol;
tertiary alcohol		antimicrobial agent;
antineoplastic agent;
fungal metabolite;
proteasome inhibitor		00low000000
ossamycin
0
cyclic hemiketal;
macrolide antibiotic;
organic heterotetracyclic compound;
secondary alcohol;
spiroketal;
tertiary alcohol		antineoplastic agent;
bacterial metabolite		00low000000
2,3-dihydro-3beta-methoxy withaferin A
0
27-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		metabolite;
plant metabolite		00low000000
migrastatin
0
ether;
macrolide antibiotic;
piperidones;
secondary alcohol		antineoplastic agent;
metabolite		00low000000
allobetulinol
0
cyclic ether;
secondary alcohol;
triterpenoid		00low000000
brivanib
0
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		00low000000
alpha-onocerin
0
diol;
olefinic compound;
secondary alcohol;
triterpenoid		plant metabolite00low000000
olodaterol
0
aromatic ether;
benzoxazine;
phenols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent		00low000000
cortistatin a
0
cortistatins;
diol;
secondary alcohol		00low000000
amrubicinol
0
diastereoisomeric mixture;
quinone;
secondary alcohol;
tetracenes		antineoplastic agent;
apoptosis inducer;
topoisomerase II inhibitor		00low000000
cytotrienin a
0
cyclopropanecarboxylate ester;
ether;
hydroquinones;
lactam;
macrocycle;
secondary alcohol		antibacterial agent;
antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
metabolite		00low000000
pyrostatin a
0
1,4,5,6-tetrahydropyrimidines;
carboxamidine;
iminium betaine;
monocarboxylic acid;
secondary alcohol		00low000000
oplodiol
0
carbobicyclic compound;
octahydronaphthalenes;
secondary alcohol;
sesquiterpenoid;
tertiary alcohol		plant metabolite00low000000
simalikalactone D
0
cyclic ether;
delta-lactone;
enone;
organic heteropentacyclic compound;
quassinoid;
secondary alcohol;
secondary alpha-hydroxy ketone;
triol		antimalarial;
antineoplastic agent;
antiviral agent;
metabolite		00low000000
monacolin l
0
2-pyranones;
hexahydronaphthalenes;
polyketide;
secondary alcohol		anticholesteremic drug;
Aspergillus metabolite;
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor		00low000000
2,3-dihydrowithaferin A
0
27-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		plant metabolite00low000000
adonixanthin
0
carotenone;
cyclic ketone;
secondary alcohol		algal metabolite;
animal metabolite;
antineoplastic agent;
bacterial metabolite;
marine metabolite;
plant metabolite		00low000000
3'-hydroxyechinenone
0
carotenone;
enone;
secondary alcohol		bacterial metabolite;
biological pigment;
cofactor		00low000000
tubocapsanolide a
0
4-hydroxy steroid;
delta-lactone;
enone;
epoxy steroid;
ergostanoid;
secondary alcohol;
withanolide		antineoplastic agent;
NF-kappaB inhibitor		00low000000
pyranonigrin a
0
cyclic ketone;
enol;
gamma-lactam;
pyranopyrrole;
secondary alcohol		antioxidant;
Aspergillus metabolite;
marine metabolite		00low000000
benzoylaconine
0
benzoate ester;
bridged compound;
diterpene alkaloid;
organic heteropolycyclic compound;
polyether;
secondary alcohol;
tertiary alcohol;
tertiary amino compound;
tetrol		phytotoxin;
plant metabolite		00low000000
tricin 4'-o-(threo-beta-guaiacylglyceryl) ether
0
dimethoxybenzene;
flavonolignan;
polyphenol;
primary alcohol;
secondary alcohol		plant metabolite00low000000
lucidenic acid n
0
cyclic terpene ketone;
dioxo monocarboxylic acid;
secondary alcohol;
tetracyclic triterpenoid		antineoplastic agent;
EC 3.1.1.8 (cholinesterase) inhibitor;
metabolite		00low000000
deoxyaconitine
0
acetate ester;
benzoate ester;
bridged compound;
diol;
diterpene alkaloid;
organic heteropolycyclic compound;
polyether;
secondary alcohol;
tertiary amino compound		plant metabolite00low000000
4'-epichaetoviridin A
0
azaphilone;
beta-hydroxy ketone;
enone;
gamma-lactone;
organic heterotricyclic compound;
organochlorine compound;
secondary alcohol		Chaetomium metabolite00low000000
eliglustat
0
benzodioxine;
carboxamide;
N-alkylpyrrolidine;
secondary alcohol		EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor00low000000
borrelidin
0
aliphatic nitrile;
diol;
macrolide;
monocarboxylic acid;
secondary alcohol		antifungal agent;
antimalarial;
antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite		00low000000
aspergillide b
0
bridged compound;
cyclic ether;
macrolide;
secondary alcohol		antineoplastic agent;
Aspergillus metabolite		00low000000
delanzomib
0
C-terminal boronic acid peptide;
phenylpyridine;
secondary alcohol;
threonine derivative		antineoplastic agent;
apoptosis inducer;
proteasome inhibitor		00low000000
benzoylmesaconine
0
benzoate ester;
bridged compound;
diterpene alkaloid;
organic heteropolycyclic compound;
polyether;
secondary alcohol;
tertiary alcohol;
tertiary amino compound;
tetrol		analgesic;
antiinfective agent;
plant metabolite		00low000000
papuamide b
0
cyclodepsipeptide;
olefinic compound;
secondary alcohol;
tertiary alcohol		anti-HIV-1 agent;
antineoplastic agent;
marine metabolite		00low000000
albiflorin
0
benzoate ester;
beta-D-glucoside;
bridged compound;
gamma-lactone;
monoterpene glycoside;
secondary alcohol		neuroprotective agent;
plant metabolite		00low000000
antroquinonol d
0
enol ether;
enone;
secondary alcohol		antineoplastic agent;
fungal metabolite		00low000000
bacillaene
0
enamine;
monocarboxylic acid amide;
polyene antibiotic;
polyketide;
secondary alcohol		antibacterial agent;
antimicrobial agent;
bacterial metabolite		00low000000
fumonisin b4
0
diester;
fumonisin;
primary amino compound;
secondary alcohol		Aspergillus metabolite00low000000
debromoaplysiatoxin
0
aplysiatoxins;
cyclic hemiketal;
ether;
organic heterotricyclic compound;
phenols;
secondary alcohol;
spiroketal		algal metabolite;
carcinogenic agent;
cyanotoxin;
marine metabolite;
protein kinase C agonist		00low000000
aplysiatoxin
0
aplysiatoxins;
bromophenol;
cyclic hemiketal;
ether;
organic heterotricyclic compound;
secondary alcohol;
spiroketal		algal metabolite;
carcinogenic agent;
cyanotoxin;
marine metabolite;
protein kinase C agonist		00low000000
eurycomanone
0
cyclic ether;
delta-lactone;
enone;
organic heteropentacyclic compound;
pentol;
quassinoid;
secondary alcohol;
secondary alpha-hydroxy ketone;
tertiary alcohol		antimalarial;
antineoplastic agent;
metabolite		00low000000
crambescidin 800
0
alkaloid;
carboxylic ester;
guanidines;
monocarboxylic acid amide;
organic heteropentacyclic compound;
primary amino compound;
secondary alcohol;
spiro compound		anti-HIV-1 agent;
anti-HSV-1 agent;
antimalarial;
marine metabolite		00low000000
afidopyropen
0
cyclopropanecarboxylate ester;
organic heterotetracyclic compound;
pyridines;
secondary alcohol		agrochemical;
insecticide;
TRPV channel modulator		00low000000
orobanchol
0
indenofuran;
secondary alcohol;
strigolactone		plant metabolite00low000000
asperfuranone
0
2-benzofurans;
cyclic ketone;
diol;
polyketide;
secondary alcohol;
tertiary alcohol;
tertiary alpha-hydroxy ketone		antineoplastic agent;
fungal metabolite		00low000000
aspergillide a
0
bridged compound;
cyclic ether;
macrolide;
secondary alcohol		antineoplastic agent;
Aspergillus metabolite		00low000000
capilliposide b
0
alpha-L-arabinopyranoside;
bridged compound;
cyclic ether;
diol;
hexacyclic triterpenoid;
hexanoate ester;
lactol;
secondary alcohol;
tetrasaccharide derivative;
triterpenoid saponin		antineoplastic agent;
plant metabolite		00low000000
myriaporone 3
0
beta-hydroxy ketone;
epoxide;
lactol;
oxanes;
primary alcohol;
secondary alcohol		antineoplastic agent;
metabolite		00low000000
BDA-366
0
anthraquinone;
epoxide;
secondary alcohol;
secondary amino compound;
tertiary amino compound		antineoplastic agent;
apoptosis inducer		00low000000
cyclooctatin
0
carbotricyclic compound;
diterpenoid;
primary alcohol;
secondary alcohol;
tertiary alcohol		bacterial metabolite;
EC 3.1.1.5 (lysophospholipase) inhibitor		00low000000
entecavir
0
2-aminopurines;
oxopurine;
primary alcohol;
secondary alcohol		antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor		00low000000
chrysogine
0
cyclic amide;
quinazoline alkaloid;
quinazolines;
secondary alcohol;
secondary amide		Aspergillus metabolite;
biological pigment;
marine metabolite		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
travoprost
0
(trifluoromethyl)benzenes;
isopropyl ester;
prostaglandins Falpha		antiglaucoma drug;
antihypertensive agent;
ophthalmology drug;
prodrug;
prostaglandin receptor agonist		00low000000
17-phenyltrinorprostaglandin e2
0
alicyclic ketone;
beta-hydroxy ketone;
hydroxy monocarboxylic acid;
olefinic compound;
oxo monocarboxylic acid;
prostanoid;
secondary alcohol		human metabolite;
prostaglandin receptor agonist		00low000000
fluprostenol
0
(trifluoromethyl)benzenes;
hydroxy monocarboxylic acid;
prostaglandins Falpha		abortifacient;
antiglaucoma drug;
antihypertensive agent;
female contraceptive drug;
prostaglandin receptor agonist		00low000000
beraprost
0
enyne;
monocarboxylic acid;
organic heterotricyclic compound;
secondary alcohol;
secondary allylic alcohol		anti-inflammatory agent;
antihypertensive agent;
platelet aggregation inhibitor;
prostaglandin receptor agonist;
vasodilator agent		00low000000
tafluprost
0
isopropyl ester;
organofluorine compound;
prostaglandins Falpha		prostaglandin receptor agonist00low000000
beraprost sodium
0
organic sodium saltanti-inflammatory agent;
antihypertensive agent;
platelet aggregation inhibitor;
prostaglandin receptor agonist;
vasodilator agent		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
17-phenyltrinorprostaglandin e2
0
alicyclic ketone;
beta-hydroxy ketone;
hydroxy monocarboxylic acid;
olefinic compound;
oxo monocarboxylic acid;
prostanoid;
secondary alcohol		human metabolite;
prostaglandin receptor agonist		00low000000
fluprostenol
0
(trifluoromethyl)benzenes;
hydroxy monocarboxylic acid;
prostaglandins Falpha		abortifacient;
antiglaucoma drug;
antihypertensive agent;
female contraceptive drug;
prostaglandin receptor agonist		00low000000
beraprost
0
enyne;
monocarboxylic acid;
organic heterotricyclic compound;
secondary alcohol;
secondary allylic alcohol		anti-inflammatory agent;
antihypertensive agent;
platelet aggregation inhibitor;
prostaglandin receptor agonist;
vasodilator agent		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
ay 23626
1
1977197747.0high010000
dinoprostone
1
prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic		2003200321.0low000100
alprostadil
1
prostaglandins Eanticoagulant;
human metabolite;
platelet aggregation inhibitor;
vasodilator agent		1977197747.0low010000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
carbachol
1
ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic		201520159.0low000010
thiophenes
1
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent201520159.0low000010
triazoles
1
1,2,3-triazole201520159.0low000010
dinoprostone
7
prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic		201120189.3high000070
alprostadil
3
prostaglandins Eanticoagulant;
human metabolite;
platelet aggregation inhibitor;
vasodilator agent		2011201610.0medium000030
deamino arginine vasopressin
1
heterodetic cyclic peptidediagnostic agent;
renal agent;
vasopressin receptor agonist		201620168.0low000010
sulprostone
1
prostanoid201520159.0low000010
l-161982
1
biphenyls201520159.0low000010
pituitrin
1
2011201113.0low000010
butaprost
3
2011201610.0medium000030
interleukin-8
1
201520159.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acquired Nephrogenic Diabetes Insipidus0
1
2011201113.0medium000010
Elevated Cholesterol0
1
201820186.0medium000010
Hypercholesterolemia0
1
201820186.0medium000010
Muscle Contraction0
1
201520159.0medium000010
Peritonitis0
1
201520159.0medium000010
Primary Peritonitis0
1
201520159.0medium000010