(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanamido]-N-[(1S)-1-carbamoyl-3-methylbutyl]hexanamide

• ChemBase ID: 155643
• Molecular Formular: C21H42N6O5
• Molecular Mass: 458.59538
• Monoisotopic Mass: 458.32166847
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N)CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)N)CO
• InChI: InChI=1S/C21H42N6O5/c1-12(2)9-14(23)19(30)27-17(11-28)21(32)25-15(7-5-6-8-22)20(31)26-16(18(24)29)10-13(3)4/h12-17,28H,5-11,22-23H2,1-4H3,(H2,24,29)(H,25,32)(H,26,31)(H,27,30)/t14-,15-,16-,17-/m0/s1
• InChIKey: YOKXDNNIFSAXBY-QAETUUGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanamido]-N-[(1S)-1-carbamoyl-3-methylbutyl]hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanamido]-N-[(1S)-1-carbamoyl-3-methylbutyl]hexanamide
• Synonyms: LSKL-NH2; Leu-Ser-Lys-Leu-NH2

Database IDs

• MDL Number: MFCD03093441
• PubChem SID: 162249781
• PubChem CID: 71312184

CALCULATED PROPERTIES

• Acid pKa: 11.983528
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -7.177309
• LogD (pH = 7.4): -5.0724926
• Log P: -1.6658013
• Molar Refractivity: 120.4148 cm^3
• Polarizability: 47.982025 Å^3
• Polar Surface Area: 202.66 Å^2
• Rotatable Bonds: 16
• 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: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C21H42N6O5

DETAILS

Sigma Aldrich - L5538

Amino Acid Sequence
Leu-Ser-Lys-Leu-NH2
Biochem/physiol Actions
Used to study the activation of TGF-β1
Leu-Ser-Lys-Leu-NH2 (LSKL-NH2) is found at the C-terminal of the neurotoxic wasp venom α-pompilidotoxin (α-PMTX). A similar peptide Leu-Ser-Lys-Leu (LSKL) is a used to study the activation of TGF-β1 via thrombospondin.