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

• ChemBase ID: 154803
• Molecular Formular: C47H75F3N10O15
• Molecular Mass: 1077.1516096
• Monoisotopic Mass: 1076.53654641
• 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](CO)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](CO)N)CC(=O)N)Cc1ccccc1)CCC(=O)O
• InChI: InChI=1S/C45H74N10O13.C2HF3O2/c1-7-25(5)36(55-44(66)37(26(6)8-2)54-38(60)28(47)23-56)43(65)52-32(22-34(48)57)42(64)51-31(21-27-14-10-9-11-15-27)41(63)50-30(17-18-35(58)59)40(62)49-29(16-12-13-19-46)39(61)53-33(45(67)68)20-24(3)4;3-2(4,5)1(6)7/h9-11,14-15,24-26,28-33,36-37,56H,7-8,12-13,16-23,46-47H2,1-6H3,(H2,48,57)(H,49,62)(H,50,63)(H,51,64)(H,52,65)(H,53,61)(H,54,60)(H,55,66)(H,58,59)(H,67,68);(H,6,7)/t25-,26-,28-,29-,30-,31-,32-,33-,36-,37-;/m0./s1
• InChIKey: BRUCWCULSHVYBQ-VPZPQSBKSA-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-3-hydroxypropanamido]-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-3-hydroxypropanamido]-3-methylpentanamido]-3-methylpentanamido]-3-carbamoylpropanamido]-3-phenylpropanamido]-4-carboxybutanamido]hexanamido]-4-methylpentanoic acid; trifluoroacetic acid
• Synonyms: L-seryl-L-isoleucyl-L-isoleucyl-L-asparaginyl-L-phenylalanyl-L-a-glutamyl-L-lysyl- L-Leucine trifluoroacetate; OVA (257 - 264); Ovalbumin (257-264) (chicken); Ser-Ile-Ile-Asn-Phe-Glu-Lys-Leu trifluoroaceate; pOV8; SIINFEKL trifluoroacetate salt

Database IDs

• CAS Number: 138831-86-4(freebase)
• MDL Number: MFCD18452854
• PubChem SID: 162248941
• PubChem CID: 71311993

CALCULATED PROPERTIES

• Rotatable Bonds: 34
• Lipinski's Rule of Five: false
• Acid pKa: 3.280796
• H Acceptors: 15
• H Donor: 13
• LogD (pH = 5.5): -6.2611527
• LogD (pH = 7.4): -6.466894
• Log P: -6.2630396
• Molar Refractivity: 244.5688 cm^3
• Polarizability: 96.775505 Å^3
• Polar Surface Area: 393.66 Å^2

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: white to off-white lyophilized powder

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C45H74N10O13 · xC2HF3O2

DETAILS

Sigma Aldrich - S7951

Amino Acid Sequence
Ser-Ile-Ile-Asn-Phe-Glu-Lys-Leu
Biochem/physiol Actions
SIINFEKL is a class I (Kb)-restricted peptide epitope of ovalbumin (OVA); the ovalbumin fragment is presented by the class I MHC molecule, H-2Kb.