Structure via PubChem · Public domain (PubChem)
Microcystin-LR
Sign in to saveMicrocystin-LR (MC-LR) is a toxin produced by cyanobacteria. It is the most toxic of the microcystins.
Chemical data
- Formula
- C49H74N10O12
- Molecular weight
- 995.2 g/mol
- IUPAC name
- (5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
- SMILES
- C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C
- InChIKey
- ZYZCGGRZINLQBL-GWRQVWKTSA-N
- XLogP
- 2.3
- Polar surface area
- 343 Ų
- H-bond donors
- 10
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 994.548767808
Show 6 more facts
- found in taxon
- Anabaena
- canonical SMILES
- CC1C(NC(=O)C(NC(=O)C(C(NC(=O)C(NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)C=CC(=CC(C)C(CC2=CC=CC=C2)OC)C
- isomeric SMILES
- C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C
- chemical formula
- C₄₉H₇₄N₁₀O₁₂
- subject has role
- enzyme inhibitor
- Commons category
- Microcystin-LR
Sources (2)
via Wikidata · CC0
~16 min read
Encyclopedic overview
26 sectionsContents
- Structure
- Biosynthesis
- Mechanism of toxicity
- Effects
- Human poisonings
- Short-term effects
- Long-term effects
- Animal effects
- Exposure Routes
- Disposition and metabolism
- Disposition
- Metabolism
- Toxicity
- Acute subacute toxicity
- Repeated oral administration
- Carcinogenicity
- Microcystin alone
- Interaction with tumors
- ''In vivo'' animal experiments
- Developmental effects
- Genotoxicity
- ''In vitro'' studies
- Biodegradation
- History
- References
- External links
Microcystin-LR (MC-LR) is a toxin produced by cyanobacteria. It is the most toxic of the microcystins.
==Structure== Microcystins are cyclic heptapeptides. The seven amino acids that are involved in the structure of a microcystin include the unique amino acids ADDA and D-β-methyl-isoaspartate (D-β-Me-isoAsp). Furthermore, microcystins contain two variable residues, which make the differentiation between variants of microcystins. These two variable functionalities are always standard proteinogenic amino acids - In microcystin-LR these are leucine and arginine.
Excerpted from Wikipedia’s “Microcystin-LR” article, available under the CC BY-SA 4.0 licence.