(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-methylpentanamido]-3-methylpentanamido]hexanamido]acetamido}-4-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]acetamido}-N-[(1S)-1-{[(1S,2S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-carbamoyl-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]hexanamide; trifluoroacetic acid

• ChemBase ID: 155018
• Molecular Formular: C116H177F3N30O23S
• Molecular Mass: 2448.8939896
• Monoisotopic Mass: 2447.32756773
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](Cc1ccccc1)NC(=O)CN.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[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)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N)C(C)C)CC(C)C)Cc1nc[nH]c1)[C@H](CC)C)CCSC)CCCCN)C)Cc1nc[nH]c1)Cc1ccccc1)CC(C)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)CN)Cc1ccccc1)Cc1nc[nH]c1
• InChI: InChI=1S/C114H176N30O21S.C2HF3O2/c1-17-67(11)94(113(164)139-86(51-75-55-119-61-125-75)101(152)124-60-92(148)132-82(47-65(7)8)108(159)140-93(66(9)10)98(118)149)141-103(154)80(42-45-166-16)133-102(153)79(41-31-33-44-116)129-90(146)58-122-99(150)71(15)128-104(155)87(52-76-56-120-62-126-76)136-106(157)84(49-73-36-26-22-27-37-73)135-105(156)81(46-64(5)6)131-91(147)59-123-100(151)78(40-30-32-43-115)134-111(162)96(69(13)19-3)144-114(165)97(70(14)20-4)143-110(161)88(53-77-57-121-63-127-77)137-107(158)85(50-74-38-28-23-29-39-74)138-112(163)95(68(12)18-2)142-109(160)83(130-89(145)54-117)48-72-34-24-21-25-35-72;3-2(4,5)1(6)7/h21-29,34-39,55-57,61-71,78-88,93-97H,17-20,30-33,40-54,58-60,115-117H2,1-16H3,(H2,118,149)(H,119,125)(H,120,126)(H,121,127)(H,122,150)(H,123,151)(H,124,152)(H,128,155)(H,129,146)(H,130,145)(H,131,147)(H,132,148)(H,133,153)(H,134,162)(H,135,156)(H,136,157)(H,137,158)(H,138,163)(H,139,164)(H,140,159)(H,141,154)(H,142,160)(H,143,161)(H,144,165);(H,6,7)/t67-,68-,69-,70-,71-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,93-,94-,95-,96-,97-;/m0./s1
• InChIKey: XLUXDFYRYMKELD-GFEQIIKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-methylpentanamido]-3-methylpentanamido]hexanamido]acetamido}-4-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]acetamido}-N-[(1S)-1-{[(1S,2S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-carbamoyl-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]hexanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-methylpentanamido]-3-methylpentanamido]hexanamido]acetamido}-4-methylpentanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]acetamido}-N-[(1S)-1-{[(1S,2S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-carbamoyl-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]hexanamide; trifluoroacetic acid
• Synonyms: Epinecidin-1 trifluoroacetate salt; Epinecidine-1 trifluoroacetate salt

Database IDs

• MDL Number: MFCD18633329
• PubChem SID: 162249156
• PubChem CID: 71312053

CALCULATED PROPERTIES

• Acid pKa: 11.897212
• H Acceptors: 27
• H Donor: 27
• LogD (pH = 5.5): -12.263056
• LogD (pH = 7.4): -7.537878
• Log P: -1.7830948
• Molar Refractivity: 617.5792 cm^3
• Polarizability: 242.2793 Å^3
• Polar Surface Area: 789.19 Å^2
• Rotatable Bonds: 78
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C114H176N30O21S·C2HF3O2

DETAILS

Sigma Aldrich - SML0013

Biochem/physiol Actions
Epinecidin-1 is an antimicrobial peptide (AMP) with antitumor and antiviral activity, which was cloned from orange-spotted grouper (Epinephelus coioides). Apparently epinecidin-1 binds to microbial surface and next destroys microbial membrane. Epinecidin-1 was effective in protecting grouper larvae from nervous necrosis viral (NNV) disease.