(4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid

• ChemBase ID: 131007
• Molecular Formular: C114H181N31O28S
• Molecular Mass: 2465.91284
• Monoisotopic Mass: 2464.34130531
• SMILES: CC[C@@H](C)[C@H](C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](Cc1c[nH]cn1)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](Cc1ccccc1)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](C)C(=O)N[C@H](Cc1ccccc1)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)N)NC(=O)CN
• Canonical SMILES: NCCCC[C@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N)CO)CC(=O)N)CCSC)[C@@H](CC)C)CCC(=O)O)C(C)C)Cc1ccccc1)C)CCCCN)Cc1ccccc1)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H]([C@@H](CC)C)NC(=O)CN)CCCCN)Cc1ccccc1)CC(C)C)Cc1nc[nH]c1)CO)C)CCCCN
• InChI: InChI=1S/C114H181N31O28S/c1-12-65(7)94(143-88(149)55-119)113(172)125-59-90(151)130-74(38-24-28-45-116)101(160)138-81(51-70-33-19-15-20-34-70)107(166)136-79(49-63(3)4)106(165)139-83(53-72-56-122-62-126-72)108(167)142-86(61-147)111(170)128-67(9)97(156)132-75(39-25-29-46-117)102(161)133-76(40-26-30-47-118)103(162)137-80(50-69-31-17-14-18-32-69)99(158)123-57-89(150)129-73(37-23-27-44-115)100(159)127-68(10)98(157)135-82(52-71-35-21-16-22-36-71)110(169)144-93(64(5)6)112(171)124-58-91(152)131-77(41-42-92(153)154)105(164)145-95(66(8)13-2)114(173)134-78(43-48-174-11)104(163)140-84(54-87(120)148)109(168)141-85(60-146)96(121)155/h14-22,31-36,56,62-68,73-86,93-95,146-147H,12-13,23-30,37-55,57-61,115-119H2,1-11H3,(H2,120,148)(H2,121,155)(H,122,126)(H,123,158)(H,124,171)(H,125,172)(H,127,159)(H,128,170)(H,129,150)(H,130,151)(H,131,152)(H,132,156)(H,133,161)(H,134,173)(H,135,157)(H,136,166)(H,137,162)(H,138,160)(H,139,165)(H,140,163)(H,141,168)(H,142,167)(H,143,149)(H,144,169)(H,145,164)(H,153,154)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,93-,94-,95-/m1/s1
• InChIKey: VBHOTDXAQOWLHQ-ONJVDTHJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• Synonyms: D-Magainin II amide

Database IDs

• CAS Number: 129696-25-9
• PubChem SID: 162225285
• PubChem CID: 71308376

CALCULATED PROPERTIES

• Acid pKa: 3.609873
• H Acceptors: 34
• H Donor: 33
• LogD (pH = 5.5): -24.266697
• LogD (pH = 7.4): -20.235832
• Log P: -12.620802
• Molar Refractivity: 633.675 cm^3
• Polarizability: 249.21127 Å^3
• Polar Surface Area: 962.92 Å^2
• Rotatable Bonds: 86
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - M8535

Application
The all-D maganin peptides were resistant to enzymatic degradation and caused equivalent amounts of electrical conductivity when tested in planar lipid bilayers. The D enantiomers were equally active against representative Gram-negative and Gram-positive species.
Biochem/physiol Actions
Antibiotic peptide. Thought to preferentially bind to anionic phospholipids abundant in bacterial membranes with the formation of dynamic peptide-lipid supramolecular pore and cell permeabilization, magainins are positively charged and amphiphatic. Binding to artificial neutral membranes has also been demonstrated.