CHEBI:6925 - microcystin-LR

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ChEBI Name microcystin-LR
ChEBI ID CHEBI:6925
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formulae C49H74N10O12
C49H74N10O12
Net Charge 0
Average Mass 995.174
Monoisotopic Mass 994.549
InChI InChI=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
InChIKey ZYZCGGRZINLQBL-GWRQVWKTSA-N
SMILES C([C@H](OC)[C@@H](C)/C=C(\C)/C=C/[C@@]1(NC([C@H](CCCNC(=N)N)NC([C@H]([C@H](C(O)=O)NC([C@H](CC(C)C)NC([C@@H](C)NC(C(N(C(CC[C@@H](NC([C@H]1C)=O)C(O)=O)=O)C)=C)=O)=O)=O)C)=O)=O)[H])C=2C=CC=CC2
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
cyanotoxin
Any toxin produced by cyanobacteria (blue-green algae).
(via microcystin )
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
(via microcystin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
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
cyanoginosin LR ChemIDplus
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
microcystin LR ChEBI
Microcystin-LR KEGG COMPOUND
Microcystis aeruginosa toxin ChemIDplus
toxin-LR ChemIDplus
Database Links Databases
C05371 KEGG COMPOUND
Microcystin-LR Wikipedia
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Registry Numbers Types Sources
101043-37-2 CAS Registry Number KEGG COMPOUND
101043-37-2 CAS Registry Number ChemIDplus
4779759 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
21 March 2016