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CHEBI:133298 - microcystin LW

ChEBI IDCHEBI:133298
ChEBI Namemicrocystin LW
Stars
DefinitionA microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-β-aspartyl, L-tryptophanyl, (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.
Last Modified4 November 2016
SubmitterCeri
DownloadsMolfile
FormulaC54H72N8O12
Net Charge0
Average Mass1025.214
Monoisotopic Mass1024.52697
SMILES[H][C@@]1(/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](Cc2cnc3ccccc23)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/C54H72N8O12/c1-29(2)24-42-52(69)61-46(54(72)73)33(6)48(65)59-43(27-37-28-55-40-19-15-14-18-38(37)40)51(68)57-39(21-20-30(3)25-31(4)44(74-10)26-36-16-12-11-13-17-36)32(5)47(64)58-41(53(70)71)22-23-45(63)62(9)35(8)50(67)56-34(7)49(66)60-42/h11-21,25,28-29,31-34,39,41-44,46,55H,8,22-24,26-27H2,1-7,9-10H3,(H,56,67)(H,57,68)(H,58,64)(H,59,65)(H,60,66)(H,61,69)(H,70,71)(H,72,73)/b21-20+,30-25+/t31-,32-,33-,34+,39-,41+,42-,43-,44-,46+/m0/s1
InChIKeyCJIASZBWXIFQMU-LNXRSHCCSA-N
Species of MetaboliteComponentSourceComments
Microcystis aeruginosa PCC 7820 (ncbitaxon:267867) - PubMed (24642434) Strain: PCC 7820
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:
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 LW (CHEBI:133298) has role bacterial metabolite (CHEBI:76969)
microcystin LW (CHEBI:133298) has role environmental contaminant (CHEBI:78298)
microcystin LW (CHEBI:133298) has role xenobiotic (CHEBI:35703)
microcystin LW (CHEBI:133298) is a microcystin (CHEBI:48041)
IUPAC Names 
cyclo[D-alanyl-L-leucyl-(3S)-3-methyl-D-β-aspartyl-L-tryptophanyl-(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]
(5R,8S,11R,12S,15S,18S,19S,22R)-15-[(1H-indol-3-yl)methyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-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-heptaazacyclopentacosane-11,22-dicarboxylic acid
Synonym  Source
MC-LWChEBI
Manual XrefsDatabases
101683967PubChem Compound
Registry NumbersSources
Reaxys:8753673Reaxys
Citations