(4S)-4-{[(1S)-3-carbamoyl-1-{[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid

• ChemBase ID: 132637
• Molecular Formular: C92H150N22O25
• Molecular Mass: 1964.3078
• Monoisotopic Mass: 1963.11424841
• 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)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@H](Cc1ccccc1)CO)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(=O)C
• Canonical SMILES: OC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)C)(C)C)(C)C)C)(C)C)C)CCC(=O)N)(C)C)(C)C)CC(C)C)(C)C)(C)C)(C)C)CCC(=O)O)CCC(=O)N)Cc1ccccc1
• InChI: InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54+,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1
• InChIKey: LGHSQOCGTJHDIL-SLKIUSOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-3-carbamoyl-1-{[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-3-carbamoyl-1-{[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid
• Synonyms: Antibiotic U-22324; Alamethicin from Trichoderma viride; (3S,12R)-1-((S)-1-((6S,12S,15S,21S,30S)-1-((R)-1-(2-Acetamido-2-methylpropanoyl)pyrrolidin-2-yl)-15-(3-amino-3-oxopropyl)-30-isobutyl-21-isopropyl-3,3,6,9,9,2,18,18,24,24,33,33-dodecamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaoxo-2,5,8,11,14,17,20,23,26,29,32-undecaazatetratriacontan-34-oyl)pyrrolidin-2-yl)-12-(((R)-5-amino-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1,5-dioxopentan-2-yl)carbamoyl)-3-isopropyl-6,6,9,9-tetramethyl-1,4,7,10-tetraoxo-2,5,8,11-tetraazapentadecan-15-oic Acid; Alamethicin

Database IDs

• CAS Number: 27061-78-5
• MDL Number: MFCD00151517
• Beilstein Number: 5213858
• PubChem SID: 162226914; 24890893
• PubChem CID: 53229968

CALCULATED PROPERTIES

• Acid pKa: 4.0946937
• H Acceptors: 25
• H Donor: 22
• LogD (pH = 5.5): -7.242025
• LogD (pH = 7.4): -8.925522
• Log P: -5.8232164
• Molar Refractivity: 499.6144 cm^3
• Polarizability: 195.59917 Å^3
• Polar Surface Area: 708.13 Å^2
• Rotatable Bonds: 53
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥50% (main component, HPLC); ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - A4665

Antibody Adsorbant
Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH2)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH2)-phenylalaninol
Biochem/physiol Actions
Monovalent cation ionophore; can mimic nerve action potential across artificial membranes.
Quality
A mixture of alamethicin homologs
Application
Alamethicin is a monovalent cation ionophore which can mimic nerve action potential across artificial membranes. Alamethicin has also been used to study membrane interactions of antimicrobial peptides.

Sigma Aldrich - 05125

Antibody Adsorbant
Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH2)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH2)-phenylalaninol
Other Notes
Alamethicin-mediated fusion of lecithin vesicles1

Toronto Research Chemicals - A470700

Alamethicin is a peptide antibiotic, produced by the fungus Trichoderma viride. Alamethicin contains the non-proteinogenic amino acid 2-aminoisobutyric acid (Aib), which strongly induces helical peptide structures. In cell membranes, it forms voltage-depe

REFERENCES

• Afonin, S., et al.: Chembiochem., 4, 1151 (2003)
• Henriques, S., et al.: Biochem. J., 399, 1 (2003)
• Almeida, P., et al.: Biochemistry, 48, 8083 (2003)
• Heitz, F., et al.: Br. J. Pharmacol., 157, 195 (2003)