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Alamethicin F50

CAT: 0931-T38296Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-T38296Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
56165-93-6
Target
Antifungal, Antibacterial, Others, Antibiotic
Related Pathways
Others, Microbiology/Virology
Bioactivity
Alamethicin F50 is a peptaibol isolated from Trichoderma. It is a polymer of 20 amino acids that includes modified and non-proteinogenic amino acids. Alamethicin F50 is a mixture of 13 different peptides, with the most abundant designated as alamethicin F50/5. Alamethicin F50 forms voltage-dependent ion channels in lipid membranes and acts as a lytic agent. It induces lysis of leukocytes (IC50 = 54 and 80 μM for rat mast cells and mouse spleen lymphocytes, respectively) and exhibits antibacterial activity against a panel of 8 mollicutes (MICs = 1.56-12.5 μM) .
Smiles
CC(C)C[C@H](NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H](NC(=O)C(C)(C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]1CCCN1C(=O)C(C)(C)NC(C)=O)C(C)C)C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](CO)Cc1ccccc1
Molecular Formula
C92H151N23O24
Molecular Weight
1963.32
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

alamethicin F50

Alamethicin F-50 has been reported in Trichoderma longibrachiatum with data available.

CAS Number56165-93-6
PubChem CID16181015
IUPAC Name(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-N-[1-[[(2S)-1-[[1-[[2-[[(2S)-1-[[1-[(2S)-2-[[(2S)-1-[[1-[[1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]pentanediamide
Molecular FormulaC92H151N23O24
Molecular Weight1963.3
XLogP-2.5
Topological Polar Surface Area714
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count24
Rotatable Bond Count53
Heavy Atom Count139
Formal Charge0
Complexity4520
SMILES
C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NC(C)(C)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CC=CC=C2)CO)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C
InChI
InChI=1S/C92H151N23O24/c1-47(2)43-58(72(127)109-92(24,25)84(139)114-41-29-33-59(114)73(128)104-65(48(3)4)75(130)112-90(20,21)82(137)113-89(18,19)80(135)103-56(36-39-62(94)119)70(125)102-55(35-38-61(93)118)69(124)99-54(46-116)44-53-31-27-26-28-32-53)100-64(121)45-96-77(132)85(10,11)111-76(131)66(49(5)6)105-81(136)88(16,17)108-71(126)57(37-40-63(95)120)101-67(122)50(7)97-78(133)86(12,13)107-68(123)51(8)98-79(134)87(14,15)110-74(129)60-34-30-42-115(60)83(138)91(22,23)106-52(9)117/h26-28,31-32,47-51,54-60,65-66,116H,29-30,33-46H2,1-25H3,(H2,93,118)(H2,94,119)(H2,95,120)(H,96,132)(H,97,133)(H,98,134)(H,99,124)(H,100,121)(H,101,122)(H,102,125)(H,103,135)(H,104,128)(H,105,136)(H,106,117)(H,107,123)(H,108,126)(H,109,127)(H,110,129)(H,111,131)(H,112,130)(H,113,137)/t50-,51-,54-,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1
InChIKey
YPZSDWIWYLTCKG-UTXLBGCNSA-N
Chemical Structure
2D Structure
2D structure of alamethicin F50
CAS: 56165-93-6
CID: 16181015
Formula: C92H151N23O24
MW: 1963.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1963.3
XLogP3-2.5
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count24
Rotatable Bond Count53
Exact Mass1962.13023278
Monoisotopic Mass1962.13023278
Topological Polar Surface Area714 Ų
Heavy Atom Count139
Formal Charge0
Complexity4520
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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