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Microcystin-LW

CAT: 0804-HY-N11679Size: InquireDry Ice: NoHazardous: No
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CAS Number
157622-02-1
UNSPSC Description
Microcystin-LW is a bacterial metabolite. Microcystin-LW is an analog of microcystin-LR. Microcystin-LW has cellular toxicity[1][2].
Target Antigen
Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Field of Research
Others
Solubility
10 mM in DMSO
Smiles
O=C(N[C@H]([C@@H](C(N[C@H](CCC(N(C1=C)C)=O)C(O)=O)=O)C)/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H](NC1=O)C)=O)CC(C)C)=O)C(O)=O)C)=O)CC3=CNC4=CC=CC=C34
Molecular Weight
1025.20
References & Citations
[1]Stanić D, et al. Microcystin production and ecological physiology of Caribbean black band disease cyanobacteria. Environ Microbiol. 2011 Apr;13(4):900-10. |[2]Ward CJ, et al. Comparative toxicity of four microcystins of different hydrophobicities to the protozoan, Tetrahymena pyriformis. J Appl Microbiol. 1999 May;86(5):874-82.
Shipping Conditions
Room temperature
Clinical Information
No Development Reported

Chemical Information

15-(1H-indol-3-ylmethyl)-18-[(1Z,3E)-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

Microcystin-LF is analog of Microcystin-LR with Phe substituted in place of Arg. It is believed to be more cell-permeable than other microcystins. 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.

CAS Number157622-02-1
PubChem CID6442262
IUPAC Name15-(1H-indol-3-ylmethyl)-18-[(1Z,3E)-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
Molecular FormulaC54H72N8O12
Molecular Weight1025.2
XLogP5.2
Topological Polar Surface Area295
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count12
Rotatable Bond Count13
Heavy Atom Count74
Formal Charge0
Complexity2090
SMILES
CC1C(NC(=O)C(NC(=O)C(C(NC(=O)C(NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CC2=CNC3=CC=CC=C32)/C=C\C(=C\C(C)C(CC4=CC=CC=C4)OC)\C
InChI
InChI=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+
InChIKey
CJIASZBWXIFQMU-ZVXOBQGSSA-N
Chemical Structure
2D Structure
2D structure of 15-(1H-indol-3-ylmethyl)-18-[(1Z,3E)-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
CAS: 157622-02-1
CID: 6442262
Formula: C54H72N8O12
MW: 1025.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1025.2
XLogP35.2
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count12
Rotatable Bond Count13
Exact Mass1024.52696976
Monoisotopic Mass1024.52696976
Topological Polar Surface Area295 Ų
Heavy Atom Count74
Formal Charge0
Complexity2090
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count10
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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