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Magainin 2

CAT: 0013-GTR19157606-01Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19157606-01Size:200 mg
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Description
Magainin II is a member of the antimicrobial peptides familyMagainin 2 exhibits bactericidal effects and induces morphological changes in Escherichia coli regarding early apoptosis. Magainin 2 induces the expression of a bacterial protein with affinity for the caspase substrate and effects the expression of RecA as a caspase-like protein. Magainin 2 kill bacteria by permeabilizing the cell membranes without exhibiting significant toxicity against mammalian cells. The main target of the peptide is considered to be the lipid matrix of the membranes. Application of 10 μg /mL magainin 2 to Paramecium caudatum, a protozoan, in pond water caused an osmotic swelling of the cell and a subsequent cell burst, suggesting that the peptide could perturb membrane functions responsible for osmotic balance. Magainin 2 permeabilizes bacterial and mammalian membranes in significantly different ways. The peptide forms pores with a diameter of about 2.8 nm (less than 6.6 nm) in B. megaterium, and translocates into the cytosol. In contrast, the peptide significantly perturbes the membrane of CHO-K1 cells, permitting the entry of a large molecule (larger than 23 nm) into the cytosol, accompanied by membrane budding and lipid flip-flop, mainly accumulating in mitochondria and nuclei
CAS Number
108433-95-0
Purity
>98% (HPLC)
Solubility
In Vitro: H2O : 50 mg/mL (20.27 mM)
Smiles
O=C (N[C@@H] (CCCCN) C (=O) N[C@@H] (C) C (=O) N[C@@H] (Cc1ccccc1) C (=O) N[C@H] (C (=O) NCC (=O) N[C@@H] (CCC (=O) O) C (=O) N[C@H] (C (=O) N[C@@H] (CCSC) C (=O) N[C@@H] (CC (N) =O) C (=O) N[C@@H] (CO) C (=O) O) [C@@H] (C) CC) C (C) C) CNC (=O) [C@H] (Cc2ccccc2) NC (=O) [C@H] (CCCCN) NC (=O) [C@H] (CCCCN) NC (=O) [C@H] (C) NC (=O) [C@H] (CO) NC (=O) [C@@H] (NC (=O) [C@H] (CC (C) C) NC (=O) [C@H] (Cc3ccccc3) NC (=O) [C@H] (CCCCN) NC (=O) CNC (=O) [C@@H] (NC (=O) CN) [C@@H] (C) CC) Cc4cncn4
Molecular Formula
C114H180N30O29S
Molecular Weight
2466.9
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Magainin 2 peptide, Xenopus

Magainin 2 peptide, Xenopus has been reported in Xenopus laevis with data available.

CAS Number108433-95-0
PubChem CID16130189
IUPAC Name(4S)-4-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]acetyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]hexanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-5-[[(2S,3S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-1,4-dioxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
Molecular FormulaC114H180N30O29S
Molecular Weight2466.9
XLogP-7.4
Topological Polar Surface Area982
Hydrogen Bond Donor Count33
Hydrogen Bond Acceptor Count36
Rotatable Bond Count86
Heavy Atom Count174
Formal Charge0
Complexity5180
SMILES
CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CO)C(=O)O)NC(=O)CN
InChI
InChI=1S/C114H180N30O29S/c1-12-65(7)94(142-88(148)55-119)112(170)124-59-90(150)129-74(38-24-28-45-116)100(158)137-81(51-70-33-19-15-20-34-70)106(164)135-79(49-63(3)4)105(163)138-83(53-72-56-121-62-125-72)107(165)140-85(60-145)110(168)127-67(9)96(154)131-75(39-25-29-46-117)101(159)132-76(40-26-30-47-118)102(160)136-80(50-69-31-17-14-18-32-69)98(156)122-57-89(149)128-73(37-23-27-44-115)99(157)126-68(10)97(155)134-82(52-71-35-21-16-22-36-71)109(167)143-93(64(5)6)111(169)123-58-91(151)130-77(41-42-92(152)153)104(162)144-95(66(8)13-2)113(171)133-78(43-48-174-11)103(161)139-84(54-87(120)147)108(166)141-86(61-146)114(172)173/h14-22,31-36,56,62-68,73-86,93-95,145-146H,12-13,23-30,37-55,57-61,115-119H2,1-11H3,(H2,120,147)(H,121,125)(H,122,156)(H,123,169)(H,124,170)(H,126,157)(H,127,168)(H,128,149)(H,129,150)(H,130,151)(H,131,154)(H,132,159)(H,133,171)(H,134,155)(H,135,164)(H,136,160)(H,137,158)(H,138,163)(H,139,161)(H,140,165)(H,141,166)(H,142,148)(H,143,167)(H,144,162)(H,152,153)(H,172,173)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,93-,94-,95-/m0/s1
InChIKey
MGIUUAHJVPPFEV-ABXDCCGRSA-N
Chemical Structure
2D Structure
2D structure of Magainin 2 peptide, Xenopus
CAS: 108433-95-0
CID: 16130189
Formula: C114H180N30O29S
MW: 2466.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight2466.9
XLogP3-7.4
Hydrogen Bond Donor Count33
Hydrogen Bond Acceptor Count36
Rotatable Bond Count86
Exact Mass2466.3286758
Monoisotopic Mass2465.3253210
Topological Polar Surface Area982 Ų
Heavy Atom Count174
Formal Charge0
Complexity5180
Isotope Atom Count0
Defined Atom Stereocenter Count21
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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