(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-phenylpropanamido]butanedioic acid

• ChemBase ID: 153617
• Molecular Formular: C33H43N5O8
• Molecular Mass: 637.72322
• Monoisotopic Mass: 637.31116336
• SMILES: CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(=O)O)C(=O)O)N
• Canonical SMILES: CC(C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)Cc1ccccc1)Cc1ccccc1)N)C
• InChI: InChI=1S/C33H43N5O8/c1-20(2)16-23(34)32(44)38-15-9-14-27(38)31(43)36-25(18-22-12-7-4-8-13-22)29(41)35-24(17-21-10-5-3-6-11-21)30(42)37-26(33(45)46)19-28(39)40/h3-8,10-13,20,23-27H,9,14-19,34H2,1-2H3,(H,35,41)(H,36,43)(H,37,42)(H,39,40)(H,45,46)/t23-,24-,25-,26-,27-/m0/s1
• InChIKey: RALAXQOLLAQGTI-IRGGMKSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-phenylpropanamido]butanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-phenylpropanamido]butanedioic acid
• Synonyms: [Pro18, Asp21]-Amyloid β Protein Fragment 17-21 trifluoroacetate salt

Database IDs

• CAS Number: 182912-74-9
• MDL Number: MFCD01862668
• PubChem SID: 162247756
• PubChem CID: 10146049

CALCULATED PROPERTIES

• Acid pKa: 3.3199766
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.4375296
• LogD (pH = 7.4): -3.264789
• Log P: -0.8933652
• Molar Refractivity: 166.323 cm^3
• Polarizability: 65.33854 Å^3
• Polar Surface Area: 208.23 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C33H43N5O8

DETAILS

Sigma Aldrich - A3097

Amino Acid Sequence
Leu-Pro-Phe-Phe-Asp
Biochem/physiol Actions
Inhibits amyloid formation in vitro, prevents amyloid neurotoxicity in cell culture, reduces in vivo cerebral amyloid deposition and completely blocks amyloid fibrial formation in rat brain.