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Microcystin-LF (Standard)

CAT: 0804-HY-N11680RSize: InquireDry Ice: NoHazardous: No
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CAT#:0804-HY-N11680RSize:Inquire
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
154037-70-4
UNSPSC Description
Microcystin-LF (Standard) is the analytical standard of Microcystin-LF. This product is intended for research and analytical applications. Microcystin-LF is a bacterial metabolite. Microcystin-LF is a phenylalanine variant of Microcystin-LR. Microcystin-LF has cellular toxicity on Caco-2 cells[1][2].
Target Antigen
Bacterial
Type
Reference Standards
Related Pathways
Anti-infection
Field of Research
Cancer
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=CC=CC=C3
Molecular Weight
986.16
References & Citations
[1]Lawton LA, et al. Isolation and characterization of microcystins from laboratory cultures and environmental samples of Microcystis aeruginosa and from an associated animal toxicosis. Nat Toxins. 1995;3(1):50-7. |[2]Vesterkvist PS, et al. Comparative cellular toxicity of hydrophilic and hydrophobic microcystins on Caco-2 cells. Toxins (Basel). 2012 Oct 25;4(11):1008-23.
Shipping Conditions
Room temperature
Clinical Information
No Development Reported

Chemical Information

Microcystin LF

Microcystin LF is a microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-beta-aspartyl, L-phenylalanyl, (2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. It has a role as a xenobiotic, a bacterial metabolite and an environmental contaminant.

CAS Number154037-70-4
PubChem CID16760563
IUPAC Name(5R,8S,11R,12S,15S,18S,19S,22R)-15-benzyl-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
Molecular FormulaC52H71N7O12
Molecular Weight986.2
XLogP5.1
Topological Polar Surface Area279
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count12
Rotatable Bond Count13
Heavy Atom Count71
Formal Charge0
Complexity1960
SMILES
C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CC2=CC=CC=C2)/C=C/C(=C/[C@H](C)[C@H](CC3=CC=CC=C3)OC)/C
InChI
InChI=1S/C52H71N7O12/c1-29(2)25-40-50(66)58-44(52(69)70)33(6)46(62)56-41(27-36-17-13-11-14-18-36)49(65)54-38(22-21-30(3)26-31(4)42(71-10)28-37-19-15-12-16-20-37)32(5)45(61)55-39(51(67)68)23-24-43(60)59(9)35(8)48(64)53-34(7)47(63)57-40/h11-22,26,29,31-34,38-42,44H,8,23-25,27-28H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,61)(H,56,62)(H,57,63)(H,58,66)(H,67,68)(H,69,70)/b22-21+,30-26+/t31-,32-,33-,34+,38-,39+,40-,41-,42-,44+/m0/s1
InChIKey
FEVBMCJUKWWWBT-QVWKUIOOSA-N
Chemical Structure
2D Structure
2D structure of Microcystin LF
CAS: 154037-70-4
CID: 16760563
Formula: C52H71N7O12
MW: 986.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight986.2
XLogP35.1
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count12
Rotatable Bond Count13
Exact Mass985.51607073
Monoisotopic Mass985.51607073
Topological Polar Surface Area279 Ų
Heavy Atom Count71
Formal Charge0
Complexity1960
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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