(2S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]-2-acetamidopentanediamide

• ChemBase ID: 155279
• Molecular Formular: C42H63N9O8
• Molecular Mass: 822.00512
• Monoisotopic Mass: 821.47996002
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)N)NC(=O)C
• 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)Cc1ccccc1)Cc1ccccc1)C(C)C)CC(C)C)NC(=O)[C@@H](NC(=O)C)CCC(=O)N
• InChI: InChI=1S/C42H63N9O8/c1-25(2)22-33(49-38(55)30(18-12-13-21-43)47-39(56)31(46-27(5)52)19-20-35(44)53)41(58)51-36(26(3)4)42(59)50-34(24-29-16-10-7-11-17-29)40(57)48-32(37(45)54)23-28-14-8-6-9-15-28/h6-11,14-17,25-26,30-34,36H,12-13,18-24,43H2,1-5H3,(H2,44,53)(H2,45,54)(H,46,52)(H,47,56)(H,48,57)(H,49,55)(H,50,59)(H,51,58)/t30-,31-,32-,33-,34-,36-/m0/s1
• InChIKey: DDXTVYDSGCHGAN-PITCCTKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]-2-acetamidopentanediamide
• IUPAC Traditional name: (2S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]-2-acetamidopentanediamide
• Synonyms: Ac-QKLVFF-NH2; amyloid blocker; Acetyl-Amyloid β-Protein Fragment 15-20 Amide

Database IDs

• CAS Number: 189064-06-0
• MDL Number: MFCD17215285
• PubChem SID: 162249417
• PubChem CID: 71312114

CALCULATED PROPERTIES

• Acid pKa: 11.749939
• H Acceptors: 9
• H Donor: 9
• LogD (pH = 5.5): -3.111082
• LogD (pH = 7.4): -2.690024
• Log P: -0.087138206
• Molar Refractivity: 220.0823 cm^3
• Polarizability: 86.435165 Å^3
• Polar Surface Area: 286.8 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... APP(351)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C42H63N9O8

DETAILS

Sigma Aldrich - A6933

Amino Acid Sequence
Ac-Gln-Lys-Leu-Val-Phe-Phe-NH2
Biochem/physiol Actions
Amyloid plaques characteristic of the Alzheimer brain contain fibrils composed of amyloid beta aggregates. Short peptides containing the sequence KLVFF have been shown to bind specifically to the homologous region in Aβ and are used to prevent full length amyloid fibril formation.