Compounds > massadine
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massadine

Description

massadine: a geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa.; structure in first source [MeSH]

massadine : An alkaloid isolated from Stylissa massa. [CHeBI]

Cross-References

ID SourceID
PubMed CID10953212
CHEBI ID73199
MeSH IDM0456286

Synonyms (4)

Synonym
CHEBI:73199
massadine
4,5-dibromo-n-[[(1s,2s,3s,4r,5s,6r,10r,12s)-8,14-diamino-3-[[(4,5-dibromo-1h-pyrrole-2-carbonyl)amino]methyl]-2,6-dihydroxy-11-oxa-7,9,13,15-tetrazatetracyclo[10.3.0.01,5.06,10]pentadeca-8,13-dien-4-yl]methyl]-1h-pyrrole-2-carboxamide
Q27140367

Roles (3)

RoleDescription
EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitorAn EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein geranylgeranyltransferase type I (EC 2.5.1.59).
animal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
marine metaboliteAny metabolite produced during a metabolic reaction in marine macro- and microorganisms.

Drug Classes (4)

ClassDescription
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
pyrrolecarboxamide
organobromine compoundA compound containing at least one carbon-bromine bond.

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's7 (58.33)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%
Other12 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
agmatine
0
guanidines;
primary amino compound		Escherichia coli metabolite;
mouse metabolite		00low000000
gamma-guanidinobutyric acid
0
guanidines;
monocarboxylic acid;
zwitterion		fungal metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		00low000000
creatine
0
glycine derivative;
guanidines;
zwitterion		geroprotector;
human metabolite;
mouse metabolite;
neuroprotective agent;
nutraceutical		00low000000
5-(n,n-hexamethylene)amiloride
0
aromatic amine;
azepanes;
guanidines;
monocarboxylic acid amide;
organochlorine compound;
pyrazines		antineoplastic agent;
apoptosis inducer;
odorant receptor antagonist;
sodium channel blocker		00low000000
ethylisopropylamiloride
0
aromatic amine;
guanidines;
monocarboxylic acid amide;
organochlorine compound;
pyrazines;
tertiary amino compound		anti-arrhythmia drug;
neuroprotective agent;
sodium channel blocker		00low000000
pimagedine
0
guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor		00low000000
apraclonidine
0
dichlorobenzene;
guanidines;
imidazolines		alpha-adrenergic agonist;
antiglaucoma drug;
beta-adrenergic agonist;
diagnostic agent;
ophthalmology drug		00low000000
arcaine
0
guanidines00low000000
bethanidine
0
guanidinesadrenergic antagonist;
antihypertensive agent		00low000000
camostat
0
benzoate ester;
carboxylic ester;
diester;
guanidines;
tertiary carboxamide		anti-inflammatory agent;
anticoronaviral agent;
antifibrinolytic drug;
antihypertensive agent;
antineoplastic agent;
antiviral agent;
serine protease inhibitor		00low000000
cimetidine
0
aliphatic sulfide;
guanidines;
imidazoles;
nitrile		adjuvant;
analgesic;
anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		00low000000
epinastine
0
benzazepine;
guanidines		anti-allergic agent;
H1-receptor antagonist;
histamine antagonist;
ophthalmology drug		00low000000
famotidine
0
1,3-thiazoles;
guanidines;
sulfonamide		anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		00low000000
guanethidine
0
azocanes;
guanidines		adrenergic antagonist;
antihypertensive agent;
sympatholytic agent		00low000000
guanidine
0
carboxamidine;
guanidines;
one-carbon compound		00low000000
guazatine
0
aliphatic nitrogen antifungal agent;
guanidines;
secondary amino compound		antifungal agrochemical00low000000
metformin
0
guanidinesenvironmental contaminant;
geroprotector;
hypoglycemic agent;
xenobiotic		00low000000
nafamostat
0
benzoic acids;
guanidines		00low000000
(n-(p-cyanophenyl)-n'-(diphenylmethyl)guanidine)acetic acid
0
glycine derivative;
guanidines		epitope;
sweetening agent		00low000000
phenyl biguanide
0
guanidinescentral nervous system drug00low000000
biguanides
0
guanidines00low000000
diphenylguanidine
0
guanidinesallergen00low000000
dicyandiamido
0
guanidines;
nitrile		curing agent;
explosive;
fertilizer;
flame retardant;
nitrification inhibitor		00low000000
methylguanidine
0
guanidinesEC 1.14.13.39 (nitric oxide synthase) inhibitor;
metabolite;
uremic toxin		00low000000
galegine
0
guanidines00low000000
amiloride
0
aromatic amine;
guanidines;
organochlorine compound;
pyrazines		diuretic;
sodium channel blocker		00low000000
guanazodine
0
guanidines00low000000
guanadrel
0
guanidines;
spiroketal		adrenergic antagonist;
antihypertensive agent		00low000000
zanamivir
0
guanidinesantiviral agent;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor		00low000000
propamidine
0
aromatic ether;
guanidines;
polyether		antimicrobial agent;
antiseptic drug		00low000000
hexamidine
0
aromatic ether;
guanidines;
polyether		antimicrobial agent;
antiseptic drug		00low000000
synthalin a
0
guanidineshepatotoxic agent;
hypoglycemic agent;
nephrotoxin		00low000000
guanidinopropionic acid
0
guanidines;
zwitterion		hypoglycemic agent00low000000
guanidinoethane sulfonate
0
guanidines;
organosulfonic acid;
zwitterion		00low000000
hydroxyguanidine
0
guanidines;
one-carbon compound		antineoplastic agent;
antiviral agent		00low000000
nopaline
0
amino acid opine;
D-glutamic acid derivative;
guanidines;
L-arginine derivative;
secondary amino compound;
tricarboxylic acid		00low000000
benzamil
0
guanidines;
pyrazines		00low000000
octopine
0
amino acid opine;
amino dicarboxylic acid;
D-alpha-amino acid zwitterion;
D-arginine derivative;
guanidines;
secondary amino compound		animal metabolite;
xenobiotic metabolite		00low000000
3',4'-dichlorobenzamil
0
guanidines;
pyrazines		00low000000
acetylphenylalanyl-prolyl-boroarginine
0
acetamides;
C-terminal boronic acid peptide;
guanidines		anticoagulant;
EC 3.4.21.5 (thrombin) inhibitor		00low000000
n,n-dimethylarginine
0
dimethylarginine;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor00low000000
e 64
0
dicarboxylic acid monoamide;
epoxy monocarboxylic acid;
guanidines;
L-leucine derivative;
zwitterion		antimalarial;
antiparasitic agent;
protease inhibitor		00low000000
omega-n-methylarginine
0
amino acid zwitterion;
arginine derivative;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid		00low000000
argininehydroxamic acid
0
guanidines;
hydroxamic acid;
L-arginine derivative		00low000000
bcx 1812
0
3-hydroxy monocarboxylic acid;
acetamides;
cyclopentanols;
guanidines		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor		00low000000
4-guanidinobenzoate
0
benzoic acids;
guanidines		00low000000
aminopotentidine
0
aromatic ether;
benzamides;
guanidines;
nitrile;
piperidines;
substituted aniline		H2-receptor antagonist00low000000
symmetric dimethylarginine
0
amino acid zwitterion;
dimethylarginine;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor00low000000
delta-n-methylarginine
0
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid		00low000000
nitroarginine
0
guanidines;
L-arginine derivative;
N-nitro compound;
non-proteinogenic L-alpha-amino acid		00low000000
argininamide
0
amino acid amide;
guanidines;
L-arginine derivative		00low000000
n(1)-guanyl-1,7-diaminoheptane
0
guanidines;
primary amino compound		antineoplastic agent;
EC 2.5.1.46 (deoxyhypusine synthase) inhibitor		00low000000
tosylarginine methyl ester
0
guanidines;
L-arginine ester;
methyl ester;
sulfonamide		00low000000
N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide
0
D-leucine derivative;
dichlorobenzene;
furoic acid;
glycine derivative;
guanidines;
pyrazolylpiperidine		00low000000
l803087
0
benzenes;
fluoroindole;
guanidines;
L-arginine derivative;
methyl ester;
phenylindole;
secondary carboxamide		somatostatin receptor agonist00low000000
mitoguazone
0
guanidines;
hydrazone		antineoplastic agent;
apoptosis inducer;
EC 4.1.1.50 (adenosylmethionine decarboxylase) inhibitor		00low000000
famotidine
0
1,3-thiazoles;
guanidines;
sulfonamide		anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		00low000000
gabexate methanesulfonate
0
benzoate ester;
guanidines;
methanesulfonate salt		00low000000
betrixaban
0
benzamides;
guanidines;
monochloropyridine;
monomethoxybenzene;
secondary carboxamide		anticoagulant;
EC 3.4.21.6 (coagulation factor Xa) inhibitor		00low000000
batzelladine a
0
alkaloid;
carboxylic ester;
guanidines;
organic heterotricyclic compound;
pyrrolopyrimidine;
triazaacenaphthylene		anti-HIV-1 agent;
metabolite		00low000000
vanchrobactin
0
catechols;
dipeptide;
guanidines;
monocarboxylic acid;
primary alcohol;
triol		bacterial metabolite;
marine metabolite;
siderophore		00low000000
decarbamylsaxitoxin
0
alkaloid;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
primary alcohol;
pyrrolopurine		bacterial metabolite;
marine metabolite;
neurotoxin;
toxin;
xenobiotic		00low000000
dibromophakellin
0
alkaloid;
guanidines;
organobromine compound		alpha-adrenergic agonist;
animal metabolite;
marine metabolite		00low000000
guanidinohydantoin
0
guanidines;
imidazolidine-2,4-dione		00low000000
hordatine a
0
aromatic ether;
benzofurans;
dicarboxylic acid diamide;
guanidines;
phenols		adrenergic antagonist;
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
saxitoxin
0
alkaloid;
carbamate ester;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
pyrrolopurine		cyanotoxin;
marine metabolite;
neurotoxin;
sodium channel blocker;
toxin		00low000000
callipeltin a
0
cyclodepsipeptide;
guanidines;
lactone;
oligopeptide;
phenols		anti-HIV-1 agent;
antifungal agent;
metabolite		00low000000
phleomycin d1
0
bi-1,3-thiazole;
chelate-forming peptide;
disaccharide derivative;
glycopeptide;
guanidines		antibacterial agent;
antifungal agent;
antimicrobial agent;
antineoplastic agent;
bacterial metabolite		00low000000
phenylamil
0
guanidines;
pyrazines		00low000000
tegaserod
0
carboxamidine;
guanidines;
hydrazines;
indoles		gastrointestinal drug;
serotonergic agonist		00low000000
n-methylphenylethanolamine
0
alkaloid;
phenylethanolamines		human metabolite;
plant metabolite		00low000000
phenethylamine
0
alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite		00low000000
epibatidine
0
alkaloid00low000000
colchicine, (+-)-isomer
0
acetamides;
alkaloid;
aromatic ether;
carbotricyclic compound		microtubule-destabilising agent;
plant metabolite		00low000000
eburnamonine
0
alkaloid00low000000
galantamine
0
alkaloid00low000000
muscimol
0
alkaloid;
isoxazoles;
primary amino compound		fungal metabolite;
GABA agonist;
oneirogen;
psychotropic drug		00low000000
trigonelline
0
alkaloid;
iminium betaine		food component;
human urinary metabolite;
plant metabolite		00low000000
vinca
0
alkaloid00low000000
colchicine
0
alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen		00low000000
dimethoxyphenylethylamine
0
alkaloid;
aromatic ether;
phenylethylamine		allergen;
plant metabolite		00low000000
dihydroberberine
0
alkaloid00low000000
cytisine
0
alkaloid;
bridged compound;
lactam;
organic heterotricyclic compound;
secondary amino compound		nicotinic acetylcholine receptor agonist;
phytotoxin;
plant metabolite		00low000000
anagyrine
0
alkaloid00low000000
pyrrolnitrin
0
alkaloid;
C-nitro compound;
monochlorobenzenes;
pyrroles		antifungal drug;
bacterial metabolite		00low000000
tetramethylpyrazine
0
alkaloid;
pyrazines		antineoplastic agent;
apoptosis inhibitor;
bacterial metabolite;
neuroprotective agent;
platelet aggregation inhibitor;
vasodilator agent		00low000000
trimethylcolchicinic acid methyl ether
0
acetamides;
alkaloid;
carbotricyclic compound		00low000000
LSM-22634
0
alkaloid00low000000
discretamine
0
alkaloid00low000000
dehydrocorydalin
0
alkaloid00low000000
11-bromovincamine
0
alkaloid00low000000
vinburnine
0
alkaloid00low000000
coptisine
0
alkaloidmetabolite00low000000
jatrorrhizine
0
alkaloid00low000000
5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
0
alkaloid00low000000
pretazettine
0
alkaloid00low000000
matrine
0
alkaloid00low000000
cryptopleurine
0
alkaloid antibiotic;
alkaloid;
aromatic ether;
organic heteropentacyclic compound		antineoplastic agent;
antiviral agent;
protein synthesis inhibitor		00low000000
quebrachamine
0
alkaloid00low000000
cularine
0
alkaloid00low000000
atherospermine
0
alkaloid00low000000
tuberostemonine
0
alkaloidmetabolite00low000000
demissidine
0
alkaloid;
organic heteropolycyclic compound;
steroid		00low000000
oxymatrine
0
alkaloid;
tertiary amine oxide		00low000000
stachydrine
0
alkaloid;
amino-acid betaine;
N-methyl-L-alpha-amino acid		food component;
human blood serum metabolite;
plant metabolite		00low000000
verticine
0
alkaloid00low000000
u-47929
0
alkaloid;
aziridines;
dipeptide;
pyrrolidines		antibacterial agent;
bacterial metabolite;
DNA synthesis inhibitor		00low000000
lycorenine
0
alkaloid00low000000
peiminine
0
alkaloid00low000000
caracurine v
0
alkaloid00low000000
demecolcine
0
alkaloid;
secondary amino compound		antineoplastic agent;
microtubule-destabilising agent		00low000000
norcoralydine
0
alkaloid00low000000
gamma-lumicolchicine
0
acetamides;
alkaloid;
carbotricyclic compound		00low000000
5-methoxycanthin-6-one
0
alkaloid;
organic heterotetracyclic compound		00low000000
Harringtonine
0
alkaloid00low000000
Amalorin
0
alkaloid;
organic heterotetracyclic compound		00low000000
acronine
0
acridone derivatives;
alkaloid		antineoplastic agent;
metabolite		00low000000
sampangine
0
alkaloid;
organic heterotetracyclic compound		antifungal agent;
plant metabolite		00low000000
crinine
0
alkaloid00low000000
18-Hydroxy-11,17-dimethoxyyohimban-16-carboxylic acid
0
alkaloid00low000000
elymoclavine
0
alkaloid00low000000
hemanthamine
0
alkaloid00low000000
carpaine
0
alkaloid;
macrodiolide		cardiovascular drug;
plant metabolite		00low000000
protoverine
0
alkaloid00low000000
hamayne
0
alkaloid00low000000
1-O-Acetyllycorine
0
alkaloid00low000000
vinpocetine
0
alkaloidgeroprotector00low000000
piperlactam s
0
alkaloid;
aromatic ether;
gamma-lactam;
organic heterotetracyclic compound;
phenols		anti-inflammatory agent;
antioxidant;
plant metabolite		00low000000
16-epivincamine
0
alkaloidmetabolite00low000000
antofine
0
alkaloid antibiotic;
alkaloid;
aromatic ether;
organic heteropentacyclic compound		angiogenesis inhibitor;
anti-inflammatory agent;
antimicrobial agent;
antineoplastic agent;
antiviral agent;
phytotoxin;
plant metabolite		00low000000
hirsutine, (16e,20beta)-isomer
0
alkaloidmetabolite00low000000
piperolactam a
0
alkaloid00low000000
croomine
0
alkaloidmetabolite00low000000
3-(4-methoxyphenyl)-3-[[2-(4-methoxyphenyl)-1-oxoethyl]amino]propanoic acid
0
alkaloid00low000000
annomontine
0
alkaloid;
aminopyrimidine;
beta-carbolines		antiparasitic agent;
metabolite		00low000000
8-hydroxymanzamine a
0
alkaloid;
beta-carbolines;
isoquinolines		anti-HSV-2 agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
metabolite		00low000000
toxiferine
0
alkaloid00low000000
erythraline
0
alkaloid00low000000
nostocarboline
0
alkaloid;
beta-carbolines;
organic cation;
organochlorine compound		antimalarial;
EC 3.1.1.8 (cholinesterase) inhibitor;
metabolite		00low000000
pipercallosidine
0
alkaloid;
benzodioxoles;
enamide;
secondary carboxamide		apoptosis inducer;
metabolite;
plant metabolite		00low000000
veratrine
0
alkaloid00low000000
pumiliotoxin a
0
alkaloid00low000000
manzamine a
0
alkaloid;
beta-carbolines;
isoquinolines		animal metabolite;
anti-HSV-1 agent;
antimalarial;
antineoplastic agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
marine metabolite		00low000000
muromonab-cd3
0
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		00low000000
ageladine a
0
alkaloid;
aromatic amine;
imidazopyridine;
organobromine compound;
pyrroles		angiogenesis inhibitor;
antineoplastic agent;
matrix metalloproteinase inhibitor;
metabolite		00low000000
acutumine
0
alkaloid00low000000
ceratamine a
0
alkaloid;
aromatic ether;
cyclic ketone;
organic heterobicyclic compound;
organobromine compound;
secondary amino compound;
tertiary amine		antimitotic;
metabolite		00low000000
neotuberostemonine
0
alkaloidmetabolite00low000000
5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-methyl)-piperidinyl)-4h-1-benzopyran-4-one
0
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		00low000000
LSM-24185
0
alkaloid00low000000
LSM-16753
0
alkaloid00low000000
lycojapodine a
0
alkaloid;
bridged compound;
cyclic ketone;
lactone;
organic heterotetracyclic compound		anti-HIV-1 agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
metabolite		00low000000
7-hydroxymitragynine
0
alkaloid00low000000
asperparaline a
0
alkaloid;
azaspiro compound;
dicarboximide		Aspergillus metabolite00low000000
leuconoxine
0
alkaloidmetabolite00low000000
undecylprodigiosin
0
alkaloid;
aromatic ether;
tripyrrole		antibacterial agent;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite;
biological pigment;
immunosuppressive agent;
radiosensitizing agent		00low000000
su 11652
0
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		00low000000
pha 665752
0
dichlorobenzene;
enamide;
indolones;
N-acylpyrrolidine;
pyrrolecarboxamide;
secondary carboxamide;
sulfone;
tertiary carboxamide		antineoplastic agent;
c-Met tyrosine kinase inhibitor		00low000000
bromhexine
0
organobromine compound;
substituted aniline;
tertiary amino compound		mucolytic00low000000
bromodiphenhydramine
0
organobromine compound;
tertiary amino compound		antimicrobial agent;
H1-receptor antagonist;
muscarinic antagonist		00low000000
bromisovalum
0
N-acylurea;
organobromine compound		00low000000
liquid crystal polymer
0
conazole fungicide;
dichlorobenzene;
organobromine compound;
oxolanes;
triazole fungicide;
triazoles		antifungal agrochemical;
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor		00low000000
halothane
0
haloalkane;
organobromine compound;
organochlorine compound;
organofluorine compound		inhalation anaesthetic00low000000
nsc 664704
0
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		00low000000
naled
0
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		00low000000
pipobroman
0
N-acylpiperazine;
organobromine compound;
tertiary carboxamide		alkylating agent;
antineoplastic agent		00low000000
sulfobromophthalein
0
2-benzofurans;
organobromine compound;
organosulfonic acid;
phenols		dye00low000000
tribromoethanol
0
alcohol;
organobromine compound		00low000000
bromthymol blue
0
2,1-benzoxathiole;
arenesulfonate ester;
organobromine compound;
polyphenol;
sultone		acid-base indicator;
dye;
two-colour indicator		00low000000
brompheniramine
0
organobromine compound;
pyridines		anti-allergic agent;
H1-receptor antagonist		00low000000
4-bromophenyl phenyl ether
0
aromatic ether;
organobromine compound		00low000000
1-bromo-2-chloroethane
0
haloalkane;
organobromine compound;
organochlorine compound		mutagen00low000000
bromphenol blue
0
2,1-benzoxathiole;
arenesulfonate ester;
organobromine compound;
phenols;
sultone		acid-base indicator;
dye;
two-colour indicator		00low000000
bromcresol purple
0
2,1-benzoxathiole;
arenesulfonate ester;
organobromine compound;
polyphenol;
sultone		acid-base indicator;
dye;
two-colour indicator		00low000000
bromacil
0
organobromine compound;
pyrimidone		00low000000
bromochlorodifluoromethane
0
one-carbon compound;
organobromine compound;
organochlorine compound;
organofluorine compound		00low000000
perflubron
0
haloalkane;
organobromine compound;
perfluorinated compound		blood substitute;
radioopaque medium		00low000000
eosine yellowish-(ys)
0
organic sodium salt;
organobromine compound		fluorochrome;
histological dye		00low000000
1-bromo-2,4-dinitrobenzene
0
C-nitro compound;
organobromine compound		00low000000
4-bromo-2-chlorophenol
0
halophenol;
monochlorobenzenes;
organobromine compound		00low000000
6-bromo-2-naphthol
0
naphthols;
organobromine compound		00low000000
cincreasin
0
benzoxazole;
organobromine compound		00low000000
8-bromo cyclic adenosine monophosphate
0
3',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
organobromine compound		antidepressant;
protein kinase agonist		00low000000
2,3,7,8-tetrabromodibenzo-4-dioxin
0
dibenzodioxine;
organobromine compound		00low000000
decamethrin
0
aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organobromine compound		agrochemical;
antifeedant;
calcium channel agonist;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
pyrethroid ester insecticide		00low000000
bromfenac
0
aromatic amino acid;
benzophenones;
organobromine compound;
substituted aniline		non-narcotic analgesic;
non-steroidal anti-inflammatory drug		00low000000
1,2-dibromo-2,4-dicyanobutane
0
aliphatic nitrile;
organobromine compound		allergen;
sensitiser		00low000000
5-bromo-4-chloro-3-indolyl beta-galactoside
0
beta-D-galactoside;
D-aldohexose derivative;
indolyl carbohydrate;
organobromine compound;
organochlorine compound		chromogenic compound00low000000
5-bromo-4-chloro-3-indoxyl phosphate
0
aryl phosphate;
indoles;
organobromine compound;
organochlorine compound		chromogenic compound00low000000
bromosuccinimide
0
dicarboximide;
organobromine compound;
pyrrolidinone		reagent00low000000
bromopyruvate
0
2-oxo monocarboxylic acid;
organobromine compound;
oxo carboxylic acid		alkylating agent;
antineoplastic agent		00low000000
gr 117289
0
1-benzofurans;
biaryl;
imidazolyl carboxylic acid;
monocarboxylic acid;
organobromine compound;
organochlorine compound;
tetrazoles		angiotensin receptor antagonist;
antihypertensive agent		00low000000
6-bromo-2-naphthyl-beta-galactopyranoside
0
beta-D-galactoside;
organobromine compound		chromogenic compound00low000000
2,2',4,4'-tetrabromodiphenyl ether
0
aromatic ether;
organobromine compound		00low000000
bromoacetaldehyde
0
organobromine compound00low000000
monobromobimane
0
organobromine compound;
pyrazolopyrazole		fluorochrome00low000000
dibromobimane
0
organobromine compound;
pyrazolopyrazole		fluorochrome00low000000
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene
0
monoterpenoid;
organobromine compound;
organochlorine compound		algal metabolite;
antineoplastic agent;
marine metabolite		00low000000
2,2',4,4',5,5'-hexabrominated diphenyl ether
0
aromatic ether;
organobromine compound		00low000000
eosine-5-isothiocyanate
0
isothiocyanate;
organobromine compound		00low000000
4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile
0
monochlorobenzenes;
nitrile;
organobromine compound;
organochlorine acaricide;
organochlorine insecticide;
organofluorine acaricide;
organofluorine insecticide;
pyrroles		acaricide;
antifouling biocide;
insecticide		00low000000
etravirine
0
aminopyrimidine;
aromatic ether;
dinitrile;
organobromine compound		antiviral agent;
HIV-1 reverse transcriptase inhibitor		00low000000
2-(4-bromophenyl)-5-(2-methylphenyl)-1,3,4-oxadiazole
0
organobromine compound00low000000
mitobronitol
0
alcohol;
organobromine compound		00low000000
pyrabactin
0
naphthalenes;
organobromine compound;
pyridines;
sulfonamide		abscisic acid receptor agonist;
hormone;
plant growth regulator		00low000000
2-amino-4-[(4-bromophenyl)methylthio]-3-azaspiro[5.5]undeca-1,4-diene-1,5-dicarbonitrile
0
organobromine compound00low000000
SMER 28
0
organobromine compound;
quinazolines;
secondary amino compound		autophagy inducer00low000000
2-(4-bromophenyl)-3,5-dimethyl-4-oxido-6-phenylpyrazin-1-ium 1-oxide
0
organobromine compound00low000000
2-(4-bromophenyl)thiazolidine
0
organobromine compound00low000000
wiskostatin
0
carbazoles;
organobromine compound;
secondary alcohol;
tertiary amino compound		00low000000
N-[1-(4-bromophenyl)ethyl]cyclobutanecarboxamide
0
organobromine compound00low000000
zd 6474
0
aromatic ether;
organobromine compound;
organofluorine compound;
piperidines;
quinazolines;
secondary amine		antineoplastic agent;
tyrosine kinase inhibitor		00low000000
bromohydrin pyrophosphate
0
alkyl diphosphate;
organobromine compound		phosphoantigen00low000000
mitolactol
0
alcohol;
organobromine compound		00low000000
bedaquiline
0
aromatic ether;
naphthalenes;
organobromine compound;
quinolines;
tertiary alcohol;
tertiary amino compound		antitubercular agent;
ATP synthase inhibitor		00low000000
metrafenone
0
aromatic ether;
aryl phenyl ketone fungicide;
benzophenones;
organobromine compound		antifungal agrochemical00low000000
1-azakenpaullone
0
lactam;
organic heterotetracyclic compound;
organobromine compound;
organonitrogen heterocyclic compound		EC 2.7.11.26 (tau-protein kinase) inhibitor;
Wnt signalling activator		00low000000
lonafarnib
0
benzocycloheptapyridine;
heteroarylpiperidine;
N-acylpiperidine;
organobromine compound;
organochlorine compound;
ureas		00low000000
5-bromouridine triphosphate
0
organobromine compound;
pyrimidine ribonucleoside 5'-triphosphate		00low000000
2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid
0
biphenyls;
organobromine compound		00low000000
jaspamide b
0
cyclodepsipeptide;
organobromine compound		animal metabolite;
antineoplastic agent;
marine metabolite		00low000000
chlorantranilipole
0
monochlorobenzenes;
organobromine compound;
pyrazole insecticide;
pyrazoles;
pyridines;
secondary carboxamide		ryanodine receptor agonist00low000000
laurinterol
0
organobromine compound;
phenols;
sesquiterpenoid		antibacterial agent;
apoptosis inducer;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
metabolite		00low000000
cyantraniliprole
0
nitrile;
organobromine compound;
organochlorine compound;
pyrazole insecticide;
pyridines;
secondary carboxamide		ryanodine receptor agonist00low000000
2,2',4,5'-tetrabromodiphenyl ether
0
aromatic ether;
organobromine compound		00low000000
hexabromodiphenyl ether 154
0
aromatic ether;
organobromine compound		00low000000
bde 183
0
aromatic ether;
organobromine compound		00low000000
macitentan
0
aromatic ether;
organobromine compound;
pyrimidines;
ring assembly;
sulfamides		antihypertensive agent;
endothelin receptor antagonist;
orphan drug		00low000000
bromophycolide a
0
diterpenoid;
macrolide;
organobromine compound;
phenols;
tertiary alcohol		anti-HIV agent;
antibacterial agent;
antifungal agent;
antimalarial;
antineoplastic agent;
metabolite		00low000000
ph 797804
0
aromatic ether;
benzamides;
organobromine compound;
organofluorine compound;
pyridone		anti-inflammatory agent;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor		00low000000
act-132577
0
aromatic ether;
organobromine compound;
pyrimidines;
sulfamides		antihypertensive agent;
drug metabolite;
endothelin receptor antagonist;
xenobiotic metabolite		00low000000
(E,E)-1-bromo-2,5-bis-(4-hydroxystyryl)benzene
0
organobromine compound;
polyphenol		fluorescent dye00low000000
lesinurad
0
aryl sulfide;
cyclopropanes;
monocarboxylic acid;
naphthalenes;
organobromine compound;
triazoles		uricosuric drug00low000000
AZ3451
0
benzimidazoles;
benzodioxoles;
nitrile;
organobromine compound;
secondary carboxamide		anti-inflammatory agent;
autophagy inducer;
PAR2 negative allosteric modulator		00low000000
8-bromocyclic gmp
0
3',5'-cyclic purine nucleotide;
organobromine compound		muscle relaxant;
protein kinase G agonist		00low000000
8-bromo-2'-deoxyguanosine
0
guanosines;
organobromine compound		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
l 778,123
0
hydrochlorideantineoplastic agent;
EC 2.5.1.58 (protein farnesyltransferase) inhibitor;
EC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor;
radiosensitizing agent		00low000000
l 778,123
0
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		00low000000
ggti-2133
0
organoammonium saltEC 2.5.1.59 (protein geranylgeranyltransferase type I) inhibitor00low000000
trimethylsulfonium
0
sulfonium compoundanimal metabolite00low000000
alpha-methylhistamine
0
aralkylamino compound;
imidazoles		animal metabolite;
H3-receptor agonist		00low000000
xanthurenic acid
0
dihydroxyquinoline;
quinolinemonocarboxylic acid		animal metabolite;
iron chelator;
metabotropic glutamate receptor agonist;
vesicular glutamate transport inhibitor		00low000000
methyl n-methylanthranilate
0
benzoate ester;
methyl ester;
secondary amino compound;
substituted aniline		animal metabolite;
fungal metabolite;
plant metabolite		00low000000
beta-glucono-1,5-lactone
0
aldono-1,5-lactone;
gluconolactone		animal metabolite;
mouse metabolite		00low000000
2,5-xylenol
0
phenolsanimal metabolite;
volatile oil component		00low000000
diethyl ketone
0
pentanoneanimal metabolite00low000000
acetophenone
0
acetophenonesanimal metabolite;
photosensitizing agent;
xenobiotic		00low000000
3-hydroxy-3-methylbutene
0
olefinic compound;
tertiary alcohol		animal metabolite;
fragrance;
pheromone;
plant metabolite		00low000000
benzyl cyanide
0
benzenes;
nitrile		animal metabolite;
pheromone		00low000000
isovanillin
0
benzaldehydes;
monomethoxybenzene;
phenols		animal metabolite;
antidiarrhoeal drug;
antifungal agent;
EC 1.2.3.1 (aldehyde oxidase) inhibitor;
HIV protease inhibitor;
plant metabolite		00low000000
pentadecane
0
long-chain alkaneanimal metabolite;
plant metabolite;
volatile oil component		00low000000
2-undecanol
0
secondary alcohol;
undecanol		animal metabolite;
flavouring agent;
pheromone;
plant metabolite;
volatile oil component		00low000000
cysteic acid
0
alanine derivative;
amino sulfonic acid;
carboxyalkanesulfonic acid;
cysteine derivative;
non-proteinogenic alpha-amino acid		animal metabolite00low000000
2,3,5-trimethylpyrazine
0
pyrazinesanimal metabolite;
bacterial metabolite;
flavouring agent;
pheromone;
plant metabolite		00low000000
norsalsolinol
0
isoquinolinolanimal metabolite;
apoptosis inducer;
human metabolite;
marine metabolite		00low000000
fluoren-9-ol
0
hydroxyfluorenes;
secondary alcohol		animal metabolite00low000000
n-acetylhistidine
0
L-histidine derivative;
N-acetyl-L-amino acid;
N-acetylhistidine		animal metabolite00low000000
2-acetamido-2-deoxy-d-glucono-(1,5)-lactone
0
deoxygluconolactoneanimal metabolite;
EC 2.3.2.52 (beta-N-acetylhexosaminidase) inhibitor;
pheromone		00low000000
phospho-l-arginine
0
L-arginine derivative;
non-proteinogenic L-alpha-amino acid;
phosphagen;
phosphoamino acid		animal metabolite00low000000
melezitose
0
trisaccharideanimal metabolite00low000000
octopine
0
amino acid opine;
amino dicarboxylic acid;
D-alpha-amino acid zwitterion;
D-arginine derivative;
guanidines;
secondary amino compound		animal metabolite;
xenobiotic metabolite		00low000000
anserine
0
beta-alanine derivative;
dipeptide;
zwitterion		animal metabolite;
mouse metabolite		00low000000
n-acetyltyramine
0
acetamides;
tyramines		animal metabolite;
Aspergillus metabolite;
bacterial metabolite;
marine metabolite;
quorum sensing inhibitor		00low000000
epietiocholanolone
0
17-oxo steroid;
3beta-hydroxy steroid;
androstanoid		androgen;
animal metabolite;
human blood serum metabolite;
mouse metabolite;
rat metabolite		00low000000
isomaltulose
0
glycosylfructoseanimal metabolite;
plant metabolite;
sweetening agent		00low000000
dolichodial
0
dialdehyde;
iridoid monoterpenoid;
olefinic compound		animal metabolite;
plant metabolite;
volatile oil component		00low000000
methionine sulfone
0
L-alpha-amino acid zwitterion;
L-methionine derivative;
methionine sulfone;
non-proteinogenic L-alpha-amino acid		animal metabolite00low000000
coniferyl alcohol
0
guaiacols;
phenylpropanoid		animal metabolite;
monolignol;
mouse metabolite;
pheromone;
plant metabolite;
volatile oil component		00low000000
farnesoic acid
0
farnesoic acidanimal metabolite00low000000
astaxanthine
0
carotenol;
carotenone		animal metabolite;
anticoagulant;
antioxidant;
food colouring;
plant metabolite		00low000000
echinenone
0
carotenoneanimal metabolite;
bacterial metabolite;
cofactor;
marine metabolite		00low000000
brassicasterol
0
3beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		algal metabolite;
animal metabolite;
biomarker;
EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor;
human metabolite;
marine metabolite;
plant metabolite;
sterol biosynthesis inhibitor		00low000000
cembrene a
0
cycloalkatriene;
diterpene;
macrocycle		animal metabolite;
bacterial metabolite;
coral metabolite		00low000000
10-hydroxy-2-decenoic acid
0
alpha,beta-unsaturated monocarboxylic acid;
hydroxy monounsaturated fatty acid;
omega-hydroxy-medium-chain fatty acid;
straight-chain fatty acid		animal metabolite;
geroprotector		00low000000
civetone
0
cyclic ketone;
macrocycle		animal metabolite;
fragrance;
pheromone		00low000000
ecdysterone
0
14alpha-hydroxy steroid;
20-hydroxy steroid;
22-hydroxy steroid;
25-hydroxy steroid;
2beta-hydroxy steroid;
3beta-sterol;
ecdysteroid;
phytoecdysteroid		animal metabolite;
plant metabolite		00low000000
tetrodotoxin
0
azatetracycloalkane;
oxatetracycloalkane;
quinazoline alkaloid		animal metabolite;
bacterial metabolite;
marine metabolite;
neurotoxin;
voltage-gated sodium channel blocker		00low000000
manzamine a
0
alkaloid;
beta-carbolines;
isoquinolines		animal metabolite;
anti-HSV-1 agent;
antimalarial;
antineoplastic agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
marine metabolite		00low000000
laulimalide
0
carboxylic ester;
epoxide;
macrolide;
secondary alcohol;
secondary allylic alcohol		animal metabolite;
antimitotic;
antineoplastic agent;
marine metabolite;
microtubule-stabilising agent		00low000000
bufalin
0
14beta-hydroxy steroid;
3beta-hydroxy steroid		animal metabolite;
anti-inflammatory agent;
antineoplastic agent;
cardiotonic drug		00low000000
dolastatin 10
0
1,3-thiazoles;
tetrapeptide		animal metabolite;
antineoplastic agent;
apoptosis inducer;
marine metabolite;
microtubule-destabilising agent		00low000000
jasplakinolide
0
cyclodepsipeptide;
phenols		actin polymerisation inducer;
animal metabolite;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
marine metabolite;
neuroprotective agent		00low000000
dysiherbaine
0
amino dicarboxylic acid;
furopyran;
hydroxy carboxylic acid;
secondary amino compound		animal metabolite;
excitatory amino acid agonist;
marine metabolite;
neurotoxin		00low000000
dysidenin
0
1,3-thiazoles;
organochlorine compound;
secondary carboxamide;
tertiary carboxamide		animal metabolite;
marine metabolite;
toxin		00low000000
carmine
0
C-glycosyl compound;
monocarboxylic acid;
tetrahydroxyanthraquinone		animal metabolite;
histological dye		00low000000
12-epi-scalarin
0
scalarane sesterterpenoidanimal metabolite00low000000
jaspamide b
0
cyclodepsipeptide;
organobromine compound		animal metabolite;
antineoplastic agent;
marine metabolite		00low000000
validoxylamine a
0
amino cyclitol;
secondary amino compound		animal metabolite;
antibiotic insecticide;
bacterial metabolite;
EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor		00low000000
neodysiherbaine a
0
amino dicarboxylic acid;
diol;
furopyran;
hydroxy carboxylic acid		animal metabolite;
excitatory amino acid agonist;
marine metabolite		00low000000
adonixanthin
0
carotenone;
cyclic ketone;
secondary alcohol		algal metabolite;
animal metabolite;
antineoplastic agent;
bacterial metabolite;
marine metabolite;
plant metabolite		00low000000
forapin
0
peptidyl amide;
polypeptide		animal metabolite;
antineoplastic agent;
apoptosis inducer;
EC 2.7.11.13 (protein kinase C) inhibitor;
hepatoprotective agent;
neuroprotective agent;
venom		00low000000
dinophysistoxin 1
0
ketalanimal metabolite;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
marine metabolite;
toxin		00low000000
scalaradial
0
acetate ester;
carbotetracyclic compound;
dialdehyde;
enal;
scalarane sesterterpenoid		animal metabolite;
anti-inflammatory agent;
apoptosis inducer;
EC 3.1.1.4 (phospholipase A2) inhibitor;
marine metabolite;
TRP channel blocker		00low000000
dibromophakellin
0
alkaloid;
guanidines;
organobromine compound		alpha-adrenergic agonist;
animal metabolite;
marine metabolite		00low000000
dehydroluciferin
0
1,3-thiazolemonocarboxylic acid;
benzothiazoles;
biaryl;
phenols		animal metabolite;
luciferin		00low000000
dimethyl sulfide
0
aliphatic sulfidealgal metabolite;
bacterial xenobiotic metabolite;
EC 3.5.1.4 (amidase) inhibitor;
Escherichia coli metabolite;
marine metabolite		00low000000
2,4,6-tribromophenol
0
bromophenolenvironmental contaminant;
fungicide;
marine metabolite		00low000000
methylene bromide
0
bromohydrocarbon;
bromomethanes		algal metabolite;
marine metabolite		00low000000
methyl bromide
0
bromohydrocarbon;
bromomethanes;
methyl halides		algal metabolite;
fumigant insecticide;
marine metabolite		00low000000
methyl chloride
0
chloromethanes;
methyl halides		marine metabolite;
mutagen;
refrigerant		00low000000
dichloroacetic acid
0
monocarboxylic acid;
organochlorine compound		astringent;
marine metabolite		00low000000
acetopyrrothine
0
acetamides;
dithiolopyrrolone antibiotic		angiogenesis inhibitor;
antibacterial agent;
antifungal agent;
antineoplastic agent;
bacterial metabolite;
chelator;
EC 2.7.7.6 (RNA polymerase) inhibitor;
marine metabolite;
protein synthesis inhibitor;
toxin		00low000000
2-bromophenol
0
bromophenolmarine metabolite00low000000
2,4-di-tert-butylphenol
0
alkylbenzene;
phenols		antioxidant;
bacterial metabolite;
marine metabolite		00low000000
4-bromophenol
0
bromophenolhuman urinary metabolite;
human xenobiotic metabolite;
marine metabolite;
mouse metabolite;
persistent organic pollutant;
rat metabolite		00low000000
ethylene dibromide
0
bromoalkane;
bromohydrocarbon		algal metabolite;
carcinogenic agent;
fumigant;
marine metabolite;
mouse metabolite;
mutagen		00low000000
indole-3-carbaldehyde
0
heteroarenecarbaldehyde;
indole alkaloid;
indoles		bacterial metabolite;
human xenobiotic metabolite;
marine metabolite;
plant metabolite		00low000000
2,6-dibromophenol
0
bromohydrocarbon;
dibromophenol		marine metabolite00low000000
2,4-dibromophenol
0
brominated flame retardant;
bromophenol;
dibromobenzene		marine metabolite00low000000
dibromoacetic acid
0
2-bromocarboxylic acid;
monocarboxylic acid		apoptosis inducer;
geroprotector;
marine metabolite		00low000000
dimethylpropiothetin
0
sulfonium betainemarine metabolite;
osmolyte		00low000000
4-amino-2,6-dinitrotoluene
0
amino-nitrotolueneexplosive;
fungal xenobiotic metabolite;
marine metabolite		00low000000
pyoluteorin
0
aromatic ketone;
beta-hydroxy ketone;
diol;
organochlorine compound;
organochlorine pesticide;
polyketide;
pyrroles;
resorcinols		antibacterial agent;
antifungal agent;
apoptosis inducer;
bacterial metabolite;
marine metabolite		00low000000
norharman
0
beta-carbolines;
mancude organic heterotricyclic parent		fungal metabolite;
marine metabolite		00low000000
viridicatin
0
hydroxyquinolineantibacterial agent;
Aspergillus metabolite;
marine metabolite;
Penicillium metabolite		00low000000
orsellinic acid
0
dihydroxybenzoic acid;
resorcinols		fungal metabolite;
marine metabolite;
metabolite		00low000000
beta-aminoglutaric acid
0
dicarboxylic acidalgal metabolite;
marine metabolite		00low000000
caldopentamine
0
polyazaalkane;
primary amino compound;
secondary amino compound		marine metabolite00low000000
n-acetyldopamine
0
acetamides;
catechols;
N-(fatty acyl)-dopamine;
secondary carboxamide		human urinary metabolite;
marine metabolite		00low000000
arsenocholine
0
arsonium ion;
organoarsenic compound		human urinary metabolite;
marine metabolite;
xenobiotic		00low000000
geographutoxin i
0
organic heterotricyclic compoundmarine metabolite00low000000
ecteinascidin 743
0
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		00low000000
11-hydroxytestosterone
0
11beta-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid;
C19-steroid		bacterial xenobiotic metabolite;
human xenobiotic metabolite;
marine metabolite		00low000000
echinuline
0
2,5-diketopiperazines;
indole alkaloid;
indoles;
olefinic compound		Aspergillus metabolite;
marine metabolite;
plant metabolite		00low000000
ovothiol c
0
aryl thiol;
L-alpha-amino acid zwitterion;
L-histidine derivative		antioxidant;
marine metabolite;
radical scavenger		00low000000
ovothiol a
0
aryl thiol;
L-alpha-amino acid zwitterion;
L-histidine derivative;
non-proteinogenic L-alpha-amino acid		antioxidant;
marine metabolite;
radical scavenger		00low000000
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene
0
monoterpenoid;
organobromine compound;
organochlorine compound		algal metabolite;
antineoplastic agent;
marine metabolite		00low000000
n-palmitoylglycine
0
fatty amide;
N-acylglycine 16:0		human metabolite;
marine metabolite		00low000000
altritol
0
hexitolalgal metabolite;
marine metabolite		00low000000
allocholic acid
0
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
allo-bile acid;
C24-steroid		human metabolite;
marine metabolite;
rat metabolite		00low000000
deferrioxamine e
0
cyclic desferrioxamine;
cyclic hydroxamic acid;
macrocycle		antineoplastic agent;
bacterial metabolite;
marine metabolite;
siderophore		00low000000
albicanol
0
carbobicyclic compound;
homoallylic alcohol;
primary alcohol;
sesquiterpenoid		antifeedant;
antifungal agent;
antineoplastic agent;
fungal metabolite;
mammalian metabolite;
marine metabolite;
plant metabolite		00low000000
fonsecin
0
aromatic ether;
cyclic hemiketal;
heptaketide;
naphtho-gamma-pyrone;
phenols		Aspergillus metabolite;
marine metabolite		00low000000
adrenosterone
0
11-oxo steroid;
17-oxo steroid;
3-oxo-Delta(4) steroid;
androstanoid		androgen;
EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor;
human urinary metabolite;
marine metabolite		00low000000
bromodeoxytopsentin
0
aromatic ketone;
bromoindole;
imidazoles;
indole alkaloid		antibacterial agent;
EC 2.7.1.40 (pyruvate kinase) inhibitor;
marine metabolite		00low000000
okadaic acid
0
polycyclic ethercalcium ionophore;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
marine metabolite		00low000000
gamma-sitosterol
0
3beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite		00low000000
epipinoresinol
0
pinoresinolmarine metabolite;
plant metabolite		00low000000
adefovir
0
aromatic ether;
aromatic ketone;
biaryl;
cyclic ketone;
naphtho-gamma-pyrone;
organooxygen heterocyclic antibiotic;
polyphenol		antimalarial;
Aspergillus metabolite;
marine metabolite		00low000000
t-muurolol
0
cadinane sesquiterpenoid;
carbobicyclic compound;
octahydronaphthalenes;
tertiary alcohol		bacterial metabolite;
fungicide;
marine metabolite;
plant metabolite;
volatile oil component		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
antheraxanthin
0
epoxycarotenolbiological pigment;
marine metabolite;
plant metabolite		00low000000
domoic acid
0
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid;
tricarboxylic acid		algal metabolite;
hapten;
marine metabolite;
neuromuscular agent;
neurotoxin		00low000000
flavasperone
0
aromatic ether;
naphtho-gamma-pyrone;
phenols		acyl-CoA:cholesterol acyltransferase 2 inhibitor;
antiviral agent;
Aspergillus metabolite;
marine metabolite		00low000000
4-hydroxyretinal
0
enal;
retinoid;
secondary allylic alcohol		marine metabolite00low000000
pectenotoxin 2
0
polycyclic ether;
spiroketal		marine metabolite00low000000
pectenotoxin 1
0
polycyclic ether;
spiroketal		marine metabolite00low000000
bryostatin 2
0
bryostatins;
cyclic hemiketal;
enoate ester;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol		antineoplastic agent;
marine metabolite;
protein kinase C agonist		00low000000
manumycin
0
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		00low000000
pectenotoxin 6
0
polycyclic ether;
spiroketal		marine metabolite00low000000
meso-zeaxanthin
0
carotenolanti-inflammatory agent;
antioxidant;
human xenobiotic metabolite;
marine metabolite		00low000000
Ala-Lys
0
dipeptidemarine metabolite00low000000
cyclo(leucyl-prolyl)
0
dipeptide;
homodetic cyclic peptide;
pyrrolopyrazine		bacterial metabolite;
marine metabolite		00low000000
plitidepsin
0
didemninanticoronaviral agent;
antineoplastic agent;
marine metabolite		00low000000
muromonab-cd3
0
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		00low000000
emindole SB
0
terpenoid indole alkaloidAspergillus metabolite;
marine metabolite;
Penicillium metabolite		00low000000
pateamine a
0
1,3-thiazoles;
macrodiolide;
olefinic compound;
primary amino compound;
tertiary amino compound		antineoplastic agent;
antiviral agent;
eukaryotic initiation factor 4F inhibitor;
marine metabolite		00low000000
holomycin
0
acetamides;
dithiolopyrrolone antibiotic		antibacterial agent;
antineoplastic agent;
bacterial metabolite;
chelator;
EC 2.7.7.6 (RNA polymerase) inhibitor;
marine metabolite		00low000000
iejimalide b
0
ether;
formamides;
macrolide		antineoplastic agent;
marine metabolite		00low000000
vibrioferrin
0
carboxylic ester;
N-acyl hemiaminal;
pyrrolidin-2-ones;
tertiary alcohol;
tricarboxylic acid		marine metabolite;
siderophore		00low000000
vanchrobactin
0
catechols;
dipeptide;
guanidines;
monocarboxylic acid;
primary alcohol;
triol		bacterial metabolite;
marine metabolite;
siderophore		00low000000
pyranonigrin a
0
cyclic ketone;
enol;
gamma-lactam;
pyranopyrrole;
secondary alcohol		antioxidant;
Aspergillus metabolite;
marine metabolite		00low000000
decarbamylsaxitoxin
0
alkaloid;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
primary alcohol;
pyrrolopurine		bacterial metabolite;
marine metabolite;
neurotoxin;
toxin;
xenobiotic		00low000000
diorcinol
0
aromatic ether;
phenols		fungal metabolite;
marine metabolite;
metabolite		00low000000
marinopyrrole a
0
aromatic ketone;
organochlorine compound;
phenols;
pyrroles		antibacterial agent;
antimicrobial agent;
antineoplastic agent;
bacterial metabolite;
marine metabolite		00low000000
papuamide b
0
cyclodepsipeptide;
olefinic compound;
secondary alcohol;
tertiary alcohol		anti-HIV-1 agent;
antineoplastic agent;
marine metabolite		00low000000
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
tropodithietic acid
0
cyclic ketone;
monocarboxylic acid;
organic disulfide;
organic heterobicyclic compound;
organosulfur heterocyclic compound		antibacterial agent;
bacterial metabolite;
marine metabolite;
signalling molecule;
toxin		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
gonyautoxin v
0
organic heterotricyclic compound;
paralytic shellfish toxin		marine metabolite00low000000
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
aspulvinone E
0
4-hydroxy-5-(4-hydroxybenzylidene)-3-(4-hydroxyphenyl)furan-2(5H)-one;
aspulvinone		antiviral agent;
Aspergillus metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
marine metabolite		00low000000
saxitoxin
0
alkaloid;
carbamate ester;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
pyrrolopurine		cyanotoxin;
marine metabolite;
neurotoxin;
sodium channel blocker;
toxin		00low000000
gonyautoxin ii
0
organic heterotricyclic compound;
paralytic shellfish toxin		marine metabolite00low000000
chrysogine
0
cyclic amide;
quinazoline alkaloid;
quinazolines;
secondary alcohol;
secondary amide		Aspergillus metabolite;
biological pigment;
marine metabolite		00low000000
cerulomycin
0
aldoxime;
aromatic ether;
bipyridines;
pyridine alkaloid		antineoplastic agent;
bacterial metabolite;
marine metabolite		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
octopine
0
amino acid opine;
amino dicarboxylic acid;
D-alpha-amino acid zwitterion;
D-arginine derivative;
guanidines;
secondary amino compound		animal metabolite;
xenobiotic metabolite		00low000000
manzamine a
0
alkaloid;
beta-carbolines;
isoquinolines		animal metabolite;
anti-HSV-1 agent;
antimalarial;
antineoplastic agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
marine metabolite		00low000000
jaspamide b
0
cyclodepsipeptide;
organobromine compound		animal metabolite;
antineoplastic agent;
marine metabolite		00low000000
dibromophakellin
0
alkaloid;
guanidines;
organobromine compound		alpha-adrenergic agonist;
animal metabolite;
marine metabolite		00low000000
6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene
0
monoterpenoid;
organobromine compound;
organochlorine compound		algal metabolite;
antineoplastic agent;
marine metabolite		00low000000
muromonab-cd3
0
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		00low000000
vanchrobactin
0
catechols;
dipeptide;
guanidines;
monocarboxylic acid;
primary alcohol;
triol		bacterial metabolite;
marine metabolite;
siderophore		00low000000
decarbamylsaxitoxin
0
alkaloid;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
primary alcohol;
pyrrolopurine		bacterial metabolite;
marine metabolite;
neurotoxin;
toxin;
xenobiotic		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
saxitoxin
0
alkaloid;
carbamate ester;
guanidines;
ketone hydrate;
paralytic shellfish toxin;
pyrrolopurine		cyanotoxin;
marine metabolite;
neurotoxin;
sodium channel blocker;
toxin		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
chlorine
1
halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite		2007200717.0low000100
pyrroles
12
pyrrole;
secondary amine		2003201813.7high000570
cyclopentane
1
cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent201520159.0low000010
sceptrin
1
pyrroles;
secondary carboxamide		2014201410.0medium000010
1,2,4-trioxane
1
2011201113.0low000010
palau'amine
2
2011201113.0medium000020
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020