microcystin-LR   Click here for help

GtoPdb Ligand ID: 4735

Synonyms: toxin-LR
Compound class: Natural product
Comment: Microcystin-LR is a cyclic peptide that is produced by blue-green algae. It is the agent responsible for the effects of human and animal poisoning from ingestion of water contaminated by algal blooms. Mechanistically it is reported as an inhibitor of the protein phosphatases PP1 and PP2A [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 22
Hydrogen bond donors 10
Rotatable bonds 15
Topological polar surface area 343.14
Molecular weight 994.55
XLogP 0.55
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES COC(C(C=C(C=CC1NC(=O)C(CCCN=C(N)N)NC(=O)C(C)C(NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC(=O)C1C)C(=O)O)C)C)C(=O)O)C)C)Cc1ccccc1
Isomeric SMILES CO[C@H]([C@H](/C=C(/C=C/[C@@H]1NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C)C)C(=O)O)\C)C)Cc1ccccc1
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
InChI Key ZYZCGGRZINLQBL-GWRQVWKTSA-N
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(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
Synonyms Click here for help
toxin-LR
Database Links Click here for help
CAS Registry No. 77238-39-2 (source: Scifinder)
ChEBI CHEBI:6925
ChEMBL Ligand CHEMBL444092
GtoPdb PubChem SID 178101446
PubChem CID 445434
Search Google for chemical match using the InChIKey ZYZCGGRZINLQBL-GWRQVWKTSA-N
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UniChem Compound Search for chemical match using the InChIKey ZYZCGGRZINLQBL-GWRQVWKTSA-N
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Wikipedia Microcystin-LR