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

• ChemBase ID: 132422
• Molecular Formular: C116H185N31O27S
• Molecular Mass: 2477.9666
• Monoisotopic Mass: 2476.37769082
• 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](C)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)N[C@@H](C)C(=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)N[C@@H](C)C(=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)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[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[C@H](C(=O)N)CO)CC(=O)N)CCSC)[C@H](CC)C)CCC(=O)O)C)C(C)C)Cc1ccccc1)C)CCCCN)C)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)C)C)CCCCN
• InChI: InChI=1S/C116H185N31O27S/c1-15-65(7)94(145-90(150)58-121)114(172)125-60-91(151)132-76(40-26-30-47-117)103(161)141-84(54-73-36-22-18-23-37-73)111(169)139-82(52-63(3)4)110(168)142-86(56-75-59-124-62-126-75)109(167)129-67(9)97(155)127-68(10)98(156)134-78(42-28-32-49-119)104(162)136-79(43-29-33-50-120)105(163)140-83(53-72-34-20-17-21-35-72)108(166)130-69(11)99(157)133-77(41-27-31-48-118)102(160)128-70(12)101(159)138-85(55-74-38-24-19-25-39-74)113(171)146-93(64(5)6)115(173)131-71(13)100(158)135-80(44-45-92(152)153)107(165)147-95(66(8)16-2)116(174)137-81(46-51-175-14)106(164)143-87(57-89(122)149)112(170)144-88(61-148)96(123)154/h17-25,34-39,59,62-71,76-88,93-95,148H,15-16,26-33,40-58,60-61,117-121H2,1-14H3,(H2,122,149)(H2,123,154)(H,124,126)(H,125,172)(H,127,155)(H,128,160)(H,129,167)(H,130,166)(H,131,173)(H,132,151)(H,133,157)(H,134,156)(H,135,158)(H,136,162)(H,137,174)(H,138,159)(H,139,169)(H,140,163)(H,141,161)(H,142,168)(H,143,164)(H,144,170)(H,145,150)(H,146,171)(H,147,165)(H,152,153)/t65-,66-,67-,68-,69-,70-,71-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,93-,94-,95-/m0/s1
• InChIKey: KKNMJWFWBZQVFT-JHWRQTFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-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-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]propanamido]hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]propanamido]-4-{[(1S,2S)-1-{[(1S)-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-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-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]propanamido]hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]propanamido]-4-{[(1S,2S)-1-{[(1S)-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• Synonyms: [Ala8,13,18]-Magainin II amide

Database IDs

• CAS Number: 117665-48-2
• MDL Number: MFCD00133058
• PubChem SID: 162226699
• PubChem CID: 24755324

CALCULATED PROPERTIES

• Acid pKa: 3.6668928
• H Acceptors: 33
• H Donor: 32
• LogD (pH = 5.5): -22.082901
• LogD (pH = 7.4): -18.051401
• Log P: -10.436362
• Molar Refractivity: 641.1191 cm^3
• Polarizability: 252.21043 Å^3
• Polar Surface Area: 942.69 Å^2
• Rotatable Bonds: 85
• 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

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - M8155

Amino Acid Sequence
Gly-Ile-Gly-Lys-Phe-Leu-His-Ala-Ala-Lys-Lys-Phe-Ala-Lys-Ala-Phe-Val-Ala-Glu-Ile-Met-Asn-Ser-NH2
Biochem/physiol Actions
Magainin analog with greater anti-microbial activity.