(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylpentanamido]-3-methylpentanamido]-3-carbamoylpropanamido]-3-phenylpropanamido]-4-carboxybutanamido]hexanamido]-4-methylpentanoic acid; trifluoroacetic acid

• ChemBase ID: 154690
• Molecular Formular: C49H77F3N10O16
• Molecular Mass: 1119.1882896
• Monoisotopic Mass: 1118.54711109
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCC(=O)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[C@H](C(=O)O)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H](CCC(=O)O)N)CC(=O)N)Cc1ccccc1)CCC(=O)O
• InChI: InChI=1S/C47H76N10O14.C2HF3O2/c1-7-26(5)38(57-46(69)39(27(6)8-2)56-40(63)29(49)17-19-36(59)60)45(68)54-33(24-35(50)58)44(67)53-32(23-28-14-10-9-11-15-28)43(66)52-31(18-20-37(61)62)42(65)51-30(16-12-13-21-48)41(64)55-34(47(70)71)22-25(3)4;3-2(4,5)1(6)7/h9-11,14-15,25-27,29-34,38-39H,7-8,12-13,16-24,48-49H2,1-6H3,(H2,50,58)(H,51,65)(H,52,66)(H,53,67)(H,54,68)(H,55,64)(H,56,63)(H,57,69)(H,59,60)(H,61,62)(H,70,71);(H,6,7)/t26-,27-,29-,30-,31-,32-,33-,34-,38-,39-;/m0./s1
• InChIKey: OAOVWFXRXDBOSX-YUPPFQQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylpentanamido]-3-methylpentanamido]-3-carbamoylpropanamido]-3-phenylpropanamido]-4-carboxybutanamido]hexanamido]-4-methylpentanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylpentanamido]-3-methylpentanamido]-3-carbamoylpropanamido]-3-phenylpropanamido]-4-carboxybutanamido]hexanamido]-4-methylpentanoic acid; trifluoroacetic acid
• Synonyms: Glu-Ile- Ile -Asn-Phe-Glu-Lys-Leu trifluoroacetate; L-a-glutamyl-L-isoleucyl-L-isoleucyl-L-asparaginyl-L-phenylalanyl-L-a-glutamyl-L-lysyl-L-Leucine trifluoroacetate; OVA - E1 Peptide; EIINFEKL trifluoroacetate salt

Database IDs

• CAS Number: 153316-01-9(freebase)
• MDL Number: MFCD17215955
• PubChem SID: 162248828
• PubChem CID: 71311939

CALCULATED PROPERTIES

• Acid pKa: 3.17175
• H Acceptors: 16
• H Donor: 13
• LogD (pH = 5.5): -6.9294806
• LogD (pH = 7.4): -8.700487
• Log P: -5.8831596
• Molar Refractivity: 253.8155 cm^3
• Polarizability: 100.387375 Å^3
• Polar Surface Area: 410.73 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: water: ~1 mg/mL ((60/40))
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C47H76N10O14 · xC2HF3O2

DETAILS

Sigma Aldrich - E3285

Amino Acid Sequence
Glu-Ile- Ile -Asn-Phe-Glu-Lys-Leu
Biochem/physiol Actions
EIINFEKL is an antagonist variant of SIINFEKL [OVA (257-264)] [it induces positive selection T-cells].