Record Information
Version1.0
Creation Date2009-11-17 20:49:41 UTC
Update Date2016-11-09 01:08:54 UTC
Accession NumberCHEM002589
Identification
Common NameMicrocystin-LW
ClassSmall Molecule
DescriptionMicrocystin-LW is a hydrophobic microcystin. Microcystins (also known as cyanoginosins) are a class of toxins produced by certain freshwater cyanobacteria. Microcystins are chemically stable over a wide range of temperature and pH, possibly as a result of their cyclic structure. The toxins are also resistant to enzymatic hydrolysis (in guts of animals) by some general proteases, such as pepsin, trypsin, collagenase, and chymotrypsin.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Bacterial Toxin
  • Ether
  • Microcystin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC54H72N8O12
Average Molecular Mass1025.196 g/mol
Monoisotopic Mass1024.527 g/mol
CAS Registry Number157622-02-1
IUPAC Name(5R,8S,11R,12S,15S,18S,19S,22R)-3,6,9,13,16,20-hexahydroxy-15-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6R)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid
Traditional Name(5R,8S,11R,12S,15S,18S,19S,22R)-3,6,9,13,16,20-hexahydroxy-15-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6R)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid
SMILESCO[C@H](CC1=CC=CC=C1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1N=C(O)[C@H](CC2=CNC3=CC=CC=C23)N=C(O)[C@@H](C)[C@@H](N=C(O)[C@H](CC(C)C)N=C(O)[C@@H](C)N=C(O)C(=C)N(C)C(=O)CC[C@@H](N=C(O)[C@H]1C)C(O)=O)C(O)=O
InChI IdentifierInChI=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
InChI KeyCJIASZBWXIFQMU-JCEGHRTGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Cyclic hybrid peptide
  • Macrolactam
  • 3-alkylindole
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Cyclic carboximidic acid
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility0.00467 mg/mL [Predicted by ALOGPS]
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP3.45ALOGPS
logP8.15ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area315.47 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity278.98 m³·mol⁻¹ChemAxon
Polarizability108.93 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-076r-9002000067-943a3b45d2e73027c908Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1110100729-ea069a663105b9d4f35aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-5244654935-bbab143cab93b924d5cbSpectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityThe site of action of microcystins is the hepatocyte, the commonest cell type in the liver. They act by disrupting the cytoskeleton, the adaptable protein framework that constantly shapes and reshapes the cell as it responds to the environment. The cells die and this destroys the finer blood vessels of the liver leading to massive hepatic bleeding. The molecular target are a group of enzymes called protein phosphatases that play a role in regulating protein interactions and activities. Very well-defined types of protein phosphatase (type 1 and type 2A) are inhibited very specifically by very low concentrations of microcystins. This enzyme removes phosphate from a protein, a common step in many biochemical pathways. This inhibition, with subsequent build up of phosphorylated proteins, is believed to be a mechanism by which microcystins destroy livers. Microcystins also activate the enzyme phosphorylase b, which plays a very important role in the affairs of the hepatocyte. The combination of inhibition and activation is rapidly lethal to the cell. The specificity of some of these toxins makes them valuable research tools.
MetabolismMicrocystins are extremely stable and resist common chemical breakdown such as hydrolysis or oxidation under conditions found in most natural water bodies. These toxins can break down slowly at high temperature (40 °C or 104 o F ) at either very low (<1) or high (>9) pH. The half-life, the time it takes for one-half of the toxin to degrade, at pH 1 and 40 oC is 3 weeks; at typical ambient conditions half-life is 10 weeks.
Toxicity ValuesLD50 for rats and mice are in the range 36-122 micrograms/kg with the inhalation toxicity 180 mg/min/m3 or 43 micrograms/kg.
Lethal DoseIn comparing the available indications of hazards from cyanotoxins with other water-related health hazards, it is conspicuous that cyanotoxins have caused numerous fatal poisonings of livestock and wildlife, but no human fatalities due to oral uptake hav
Carcinogenicity (IARC Classification)Microcystis extracts: Group 3, not classifiable as to their carcinogenicity to humans. (1)
Uses/SourcesMicrocystins are produced by the cyanobacterial cells. When the algae dies, the cell walls burst, releasing the toxin into the water.
Minimum Risk LevelWHO developed a drinking water concentration limit of 1.5 μg/L for microcystin LR. They assumed that a 60 kg (132 lbs.) person drinks two liters of water each day and that 80% of the two liters is from a contaminated source.
Health EffectsLiver damage. While microcystin-LR does not cause cancer, microcystin may stimulate the growth of cancer cells.
SymptomsThe most common sign of human poisoning with microcystins is liver damage.
TreatmentMicrocystins can be broken down by some bacterial proteases.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available