Page last updated: 2024-08-01 11:22:43

mycolactone

Description

mycolactone: toxin from Mycobacterium ulcerans required for virulence [MeSH]

Mycolactone : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID5282079
SCHEMBL ID1229472
CHEBI ID31871
MeSH IDM0300994

Synonyms (10)

Synonym
C12151 ,
mycolactone
[(6s,7s,9e,12r)-12-[(e,2s,6r,7r,9r)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl] (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate
AC1NQZGK ,
222050-77-3
SCHEMBL1229472
CHEBI:31871
DTXSID10415207
[(6s,7s,9e,12r)-12-[(e,1s,5r,6r,8r)-6,8-dihydroxy-1,3,5-trimethyl-non-3-enyl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl] (2e,4e,6e,8e,10e,12s,13s,15s)-12,13,15-trihydroxy-4,6,10-trimethyl-hexadeca-2,4,6,8,10-pentaenoate
Q6947140

Drug Classes (1)

ClassDescription
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.

Research

Studies (165)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (0.61)18.2507
2000's44 (26.67)29.6817
2010's86 (52.12)24.3611
2020's34 (20.61)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.60%)5.53%
Reviews22 (13.17%)6.00%
Case Studies1 (0.60%)4.05%
Observational0 (0.00%)0.25%
Other143 (85.63%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
hexadecanolidemacrolide00low000000
ethylene brassylatemacrolide00low000000
taleranolmacrolide00low000000
Zearalanonemacrolide;
resorcinols
00low000000
(7R)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-onemacrolide00low000000
exaltolidemacrolide00low000000
roxithromycinerythromycin derivative;
macrolide;
semisynthetic derivative
antibacterial drug00low000000
latrunculin acyclic hemiketal;
macrolide;
oxabicycloalkane;
thiazolidinone
actin polymerisation inhibitor;
metabolite;
toxin
00low000000
zeranolmacrolide00low000000
zearalenonemacrolide;
resorcinols
fungal metabolite;
mycoestrogen
00low000000
platyphyllinemacrolide00low000000
retrorsinemacrolide00low000000
senkirkinemacrolide00low000000
soraphen acyclic hemiketal;
ether;
macrolide;
olefinic compound
bacterial metabolite;
EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor;
teratogenic agent
00low000000
10-deoxymethynolidemacrolidemetabolite00low000000
l 683590ether;
lactol;
macrolide;
secondary alcohol
antifungal agent;
bacterial metabolite;
immunosuppressive agent
00low000000
acetylspiramycinacetate ester;
aldehyde;
disaccharide derivative;
ether;
macrolide;
tertiary amino compound
antibacterial drug;
antimicrobial agent;
bacterial metabolite
00low000000
alpha-zearalenolmacrolide00low000000
muskmacrolide00low000000
streptogramin a1,3-oxazoles;
cyclic ketone;
enamide;
lactam;
macrolide antibiotic;
macrolide;
pyrroline;
secondary alcohol;
secondary carboxamide;
tertiary carboxamide
antibacterial drug;
Mycoplasma genitalium metabolite
00low000000
filipinmacrolide;
olefinic compound;
polyol
bacterial metabolite;
fluorescent probe
00low000000
latrunculin bcyclic hemiketal;
macrolide;
oxabicycloalkane;
thiazolidinone
actin polymerisation inhibitor;
metabolite;
toxin
00low000000
beta-zearalenolmacrolide00low000000
demycarosylturimycin haldehyde;
disaccharide derivative;
ether;
macrolide;
tertiary amino compound
antibacterial drug;
antimicrobial agent;
bacterial metabolite
00low000000
goniodomin amacrolide00low000000
rimocidinmacrolide00low000000
albocyclinemacrolide00low000000
laulimalidecarboxylic ester;
epoxide;
macrolide;
secondary alcohol;
secondary allylic alcohol
animal metabolite;
antimitotic;
antineoplastic agent;
marine metabolite;
microtubule-stabilising agent
00low000000
fr 148083aromatic ether;
macrolide;
phenols;
secondary alcohol;
secondary alpha-hydroxy ketone
antibacterial agent;
antineoplastic agent;
metabolite;
NF-kappaB inhibitor
00low000000
LL-Z1640-1macrolide;
resorcinols
metabolite00low000000
zotarolimuslactam;
macrolide
00low000000
hypothemycinaromatic ether;
diol;
enone;
epoxide;
macrolide;
phenols;
polyketide;
secondary alpha-hydroxy ketone
antifungal agent;
antineoplastic agent;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
fungal metabolite
00low000000
protylonolidediol;
enone;
macrolide
metabolite00low000000
pyrenophorolmacrolide00low000000
iejimalide bether;
formamides;
macrolide
antineoplastic agent;
marine metabolite
00low000000
zk-219477macrolide00low000000
lactimidomycinmacrolide00low000000
doramectinmacrolide00low000000
methylamphotericin bmacrolide;
methyl ester;
monosaccharide derivative
antifungal agent;
antiinfective agent;
metabolite
00low000000
dehydrocurvularinmacrolide00low000000
kujimycin bmacrolide00low000000
isomigrastatinmacrolide00low000000
cruentaren amacrolide00low000000
ly-146032heterodetic cyclic peptide;
lipopeptide antibiotic;
lipopeptide;
macrocycle;
macrolide
antibacterial drug;
bacterial metabolite;
calcium-dependent antibiotics
00low000000
iriomoteolide-1amacrolide00low000000
archazolid bmacrolide00low000000
bromophycolide aditerpenoid;
macrolide;
organobromine compound;
phenols;
tertiary alcohol
anti-HIV agent;
antibacterial agent;
antifungal agent;
antimalarial;
antineoplastic agent;
metabolite
00low000000
umirolimuslactam;
macrolide
00low000000
ecklonialactone amacrolide00low000000
borrelidinaliphatic nitrile;
diol;
macrolide;
monocarboxylic acid;
secondary alcohol
antifungal agent;
antimalarial;
antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite
00low000000
lienomycinmacrolide00low000000
aspergillide bbridged compound;
cyclic ether;
macrolide;
secondary alcohol
antineoplastic agent;
Aspergillus metabolite
00low000000
latrunculol amacrolidemetabolite00low000000
euonineacetate ester;
dihydroagarofuran sesquiterpenoid;
macrolide;
pyridine alkaloid;
sesquiterpene alkaloid
immunosuppressive agent;
insecticide;
plant metabolite
00low000000
aigialomycin dmacrolide00low000000
mirosamicinmacrolide00low000000
ce-108macrolide00low000000
aspergillide abridged compound;
cyclic ether;
macrolide;
secondary alcohol
antineoplastic agent;
Aspergillus metabolite
00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
carbamatesamino-acid anion2014201410.0low000010
methanealkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound
bacterial metabolite;
fossil fuel;
greenhouse gas
202220222.0low000001
3-hydroxybutyric acid(omega-1)-hydroxy fatty acid;
3-hydroxy monocarboxylic acid;
hydroxybutyric acid
human metabolite202120213.0low000001
glycerolalditol;
triol
algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent
201820186.0low000010
clofaziminemonochlorobenzenes;
phenazines
dye;
leprostatic drug;
non-steroidal anti-inflammatory drug
201520159.0low000010
deferoxamineacyclic desferrioxaminebacterial metabolite;
ferroptosis inhibitor;
iron chelator;
siderophore
2010201014.0low000100
carbostyrilmonohydroxyquinoline;
quinolone
bacterial xenobiotic metabolite2011201113.0low000010
1,2-dipalmitoylphosphatidylcholine201920195.0low000010
1,2-dihydroxybenzene-3,5-disulfonic acid disodium saltorganic molecular entity2010201014.0low000100
oxazoles1,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
201820186.0low000010
acetylcysteineacetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid
antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
202020204.0low000010
streptomycinantibiotic antifungal drug;
antibiotic fungicide;
streptomycins
antibacterial drug;
antifungal agrochemical;
antimicrobial agent;
antimicrobial drug;
bacterial metabolite;
protein synthesis inhibitor
201320188.7low000030
tetradecanoylphorbol acetateacetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester
antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
201520159.0low000010
alkenes2010201113.5low000110
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acidchromanol;
monocarboxylic acid;
phenols
antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
2010201014.0low000100
clarithromycinmacrolide antibioticantibacterial drug;
environmental contaminant;
protein synthesis inhibitor;
xenobiotic
201520187.5low000020
fibrinpeptide201520225.5low100011
epothilone aepothilone;
epoxide
antineoplastic agent;
metabolite;
microtubule-stabilising agent;
tubulin modulator
2003200321.0low000100
capsaicincapsaicinoidnon-narcotic analgesic;
TRPV1 agonist;
voltage-gated sodium channel blocker
201620168.0low000010
wiskostatincarbazoles;
organobromine compound;
secondary alcohol;
tertiary amino compound
2013201311.0low000010
mycobactin201820186.0low000010
rifamycins2011201113.0low000010
cotransin202320231.0medium000001
mycolactone b2005201711.8high000140
thromboplastin202220222.0low100001
rifampincyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion
angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
201320188.7low000030
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
2019 Novel Coronavirus Disease0202320231.0low000001
Ache0201520197.0low000020
Anasarca02011201411.5low000020
Atrophy02013201311.0low000010
Atrophy, Muscle02009201114.0low000110
Atypical Mycobacterial Infection, Disseminated01999202116.4low0021631
Bacterial Skin Diseases01999201816.0low001110
Benign Neoplasms02007200717.0low000100
Bleeding02008200816.0low000100
Buruli Ulcer0200820238.2high100114917
Buruli Ulcer Disease0200820238.2high100114917
Chronic Disease0201520159.0low000010
Chronic Illness0201520159.0low000010
Cicatrix02000200024.0low001000
Cicatrization02000200024.0low001000
Cirrhosis02009201114.0low000110
Communicable Diseases, Emerging02013201311.0low000010
Contracture02011201113.0low000010
Delayed Hypersensitivity02009200915.0low000100
Disease Exacerbation02000202312.5low001001
Disease Models, Animal02007202110.5low000381
Edema02011201411.5low000020
Extravascular Hemolysis0202120213.0low000001
Fibrosis02009201114.0low000110
Fish Diseases02006201214.8low000220
Hemolysis0202120213.0low000001
Hemorrhage02008200816.0low000100
Hyperesthesia02008200816.0low000100
Hypesthesia02008201611.3low000120
Infections, Mycobacterium02006202110.4low000131
Infections, Staphylococcal0202120213.0low000001
Inflammation0200920238.8low000221
Injuries02011201113.0low000010
Innate Inflammatory Response0200920238.8low000221
Koch's Disease0201820186.0low000010
Muscle Contraction02013201311.0low000010
Muscle Weakness02009200915.0low000100
Muscular Atrophy02009201114.0low000110
Muscular Weakness02009200915.0low000100
Mycobacterium Infections02006202110.4low000131
Necrosis01999201517.5low002530
Neglected Diseases0201120189.5low000020
Neoplasms02007200717.0low000100
Nerve Degeneration02011201610.5low000020
Nerve Pain0201720177.0low000010
Neuralgia0201720177.0low000010
Pain0201520197.0low000020
Remission, Spontaneous0201620168.0low000010
Scrofuloderma02009200915.0low000100
Sensation Disorders02011201113.0low000010
Sensitivity and Specificity0200620209.8low000130
Skin Diseases, Bacterial01999201816.0low001110
Skin Ulcer02000201417.0low001410
Staphylococcal Infections0202120213.0low000001
Tuberculosis0201820186.0low000010
Wounds and Injuries02011201113.0low000010

Safety/Toxicity (3)

ArticleYear
Inhibition of Sec61-dependent translocation by mycolactone uncouples the integrated stress response from ER stress, driving cytotoxicity via translational activation of ATF4.
Cell death & disease, , 03-14, Volume: 9, Issue:3
2018
Mycolactone cytotoxicity in Schwann cells could explain nerve damage in Buruli ulcer.
PLoS neglected tropical diseases, , Volume: 11, Issue:8
2017
Antioxidants protect keratinocytes against M. ulcerans mycolactone cytotoxicity.
PloS one, , Nov-04, Volume: 5, Issue:11
2010