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CHEBI:6925 - microcystin-LR

ChEBI IDCHEBI:6925
ChEBI Namemicrocystin-LR
Stars
DefinitionA microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-β-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-γ-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.
Last Modified8 October 2018
DownloadsMolfile
FormulaC49H74N10O12
Net Charge0
Average Mass995.189
Monoisotopic Mass994.54877
SMILES[H][C@@]1(/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@H](C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@H](C(=O)O)NC(=O)[C@H]1C
InChIInChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1
InChIKeyZYZCGGRZINLQBL-GWRQVWKTSA-N
Wikipedia
Roles Classification
Chemical Roles:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor  Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
xenobiotic  A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
hepatotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
cyanotoxin  Any toxin produced by cyanobacteria (blue-green algae).
ChEBI Ontology
Outgoing Relation(s)
microcystin-LR (CHEBI:6925) has role bacterial metabolite (CHEBI:76969)
microcystin-LR (CHEBI:6925) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
microcystin-LR (CHEBI:6925) has role environmental contaminant (CHEBI:78298)
microcystin-LR (CHEBI:6925) has role xenobiotic (CHEBI:35703)
microcystin-LR (CHEBI:6925) is a microcystin (CHEBI:48041)
IUPAC Name 
cyclo[D-alanyl-L-leucyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-γ-glutamyl-2,3-didehydro-N-methylalanyl]
Synonyms  Source
Microcystin-LRKEGG COMPOUND
Microcystis aeruginosa toxinChemIDplus
cyanoginosin LRChemIDplus
toxin-LRChemIDplus
1,7-anhydro[D-alanyl-L-leucyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-γ-glutamyl-2,3-didehydro-N-methylalanine]ChEBI
cyclo[2,3-didehydro-N-methylalanyl-D-alanyl-L-leucyl-erythro-3-methyl-D-β-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-γ-glutamyl]ChEBI
Manual XrefsDatabases
C05371KEGG COMPOUND
Microcystin-LRWikipedia
Registry NumbersSources
Reaxys:4779759Reaxys
CAS:101043-37-2KEGG COMPOUND
CAS:101043-37-2ChemIDplus
Citations