CHEBI:6925 - microcystin-LR

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C49H74N10O12
Net Charge 0
Average Mass 995.174
Monoisotopic Mass 994.54877
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.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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
Manual Xrefs Databases
C05371 KEGG COMPOUND
Microcystin-LR Wikipedia
View more database links
Registry Numbers Types Sources
101043-37-2 CAS Registry Number KEGG COMPOUND
101043-37-2 CAS Registry Number ChemIDplus
4779759 Beilstein Registry Number ChemIDplus
4779759 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10903983 PubMed citation Europe PMC
17125460 PubMed citation Europe PMC
18246549 PubMed citation Europe PMC
21489775 PubMed citation Europe PMC
22071605 PubMed citation Europe PMC
22301162 PubMed citation Europe PMC
22837451 PubMed citation Europe PMC
22956115 PubMed citation Europe PMC
23131420 PubMed citation Europe PMC
23506857 PubMed citation Europe PMC
23586662 PubMed citation Europe PMC
23999063 PubMed citation Europe PMC
24268348 PubMed citation Europe PMC
24280256 PubMed citation Europe PMC
24318164 PubMed citation Europe PMC
24462717 PubMed citation Europe PMC
24631598 PubMed citation Europe PMC
28648727 PubMed citation Europe PMC
Last Modified
08 October 2018
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag