Structure via PubChem · Public domain (PubChem)
mycolactone
Sign in to saveMycolactone is a polyketide-derived macrolide produced and secreted by a group of very closely related pathogenic mycobacteria species including M. ulcerans, M. liflandii (an unofficial designation), M. pseudoshottsii, and some strains of M. marinum. These mycobacteria are collectively referred to as mycolactone-producing mycobacteria or MPM.
Chemical data
- Formula
- C44H70O9
- Molecular weight
- 743 g/mol
- IUPAC name
- [(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
- SMILES
- C[C@H]1C/C(=C/C[C@@H](OC(=O)CCC[C@@H]1OC(=O)/C=C/C(=C/C(=C/C=C/C(=C/[C@@H]([C@H](C[C@H](C)O)O)O)/C)/C)/C)[C@@H](C)C/C(=C/[C@@H](C)[C@@H](C[C@@H](C)O)O)/C)/C
- InChIKey
- WKTLNJXZVDLRTJ-QRRXZRELSA-N
- XLogP
- 8.7
- Polar surface area
- 154 Ų
- H-bond donors
- 5
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Wikidata facts
- Instance of
- toxin
- Mass
- 742.501984
Show 3 more facts
- chemical formula
- C₄₄H₇₀O₉
- isomeric SMILES
- C[C@H]1C/C(=C/C[C@@H](OC(=O)CCC[C@@H]1OC(=O)/C=C/C(=C/C(=C/C=C/C(=C/[C@@H]([C@H](C[C@H](C)O)O)O)/C)/C)/C)[C@@H](C)C/C(=C/[C@@H](C)[C@@H](C[C@@H](C)O)O)/C)/C
- canonical SMILES
- CC1CC(=CCC(OC(=O)CCCC1OC(=O)C=CC(=CC(=CC=CC(=CC(C(CC(C)O)O)O)C)C)C)C(C)CC(=CC(C)C(CC(C)O)O)C)C
Sources (1)
via Wikidata · CC0
~17 min read
Encyclopedic overview
25 sectionsContents
- History
- Early observations
- Discovery and characterization
- Evolving understanding (2000s - Present)
- Structure and reactivity
- Molecular Architecture
- Isomerism and Stereochemistry
- Physical Properties and Stability
- Structure-Activity Relationship (SAR)
- Variants
- Synthesis
- Biosynthesis
- Chemical Synthesis
- Mechanism of Action
- Metabolism
- Distribution and Transport
- Pharmacokinetics
- Biotransformation
- Persistence and Clearance
- Indications
- Buruli ulcer
- Analgesia
- Anticancer activity
- Immunosuppressive
- References
Mycolactone is a polyketide-derived macrolide produced and secreted by a group of very closely related pathogenic mycobacteria species including M. ulcerans, M. liflandii (an unofficial designation), M. pseudoshottsii, and some strains of M. marinum. These mycobacteria are collectively referred to as mycolactone-producing mycobacteria or MPM.
In humans, mycolactone is the toxin responsible for Buruli ulcers, doing so by damaging tissues and inhibiting the immune response.
Excerpted from Wikipedia’s “mycolactone” article, available under the CC BY-SA 4.0 licence.