(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]butanoic acid

• ChemBase ID: 132169
• Molecular Formular: C71H99N17O16
• Molecular Mass: 1446.65006
• Monoisotopic Mass: 1445.74557017
• 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)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N
• 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)O)Cc1ccccc1)Cc1ccccc1)C(C)C)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)CCC(=O)O)Cc1nc[nH]c1)Cc1nc[nH]c1)CCC(=O)N
• InChI: InChI=1S/C71H99N17O16/c1-39(2)29-52(68(100)88-60(41(5)6)69(101)84-53(31-42-15-9-7-10-16-42)65(97)86-56(71(103)104)32-43-17-11-8-12-18-43)82-62(94)49(19-13-14-28-72)80-63(95)50(24-26-57(74)90)81-66(98)54(33-45-35-75-37-77-45)83-67(99)55(34-46-36-76-38-78-46)85-70(102)59(40(3)4)87-64(96)51(25-27-58(91)92)79-61(93)48(73)30-44-20-22-47(89)23-21-44/h7-12,15-18,20-23,35-41,48-56,59-60,89H,13-14,19,24-34,72-73H2,1-6H3,(H2,74,90)(H,75,77)(H,76,78)(H,79,93)(H,80,95)(H,81,98)(H,82,94)(H,83,99)(H,84,101)(H,85,102)(H,86,97)(H,87,96)(H,88,100)(H,91,92)(H,103,104)/t48-,49-,50-,51-,52-,53-,54-,55-,56-,59-,60-/m0/s1
• InChIKey: VCLPDRBVMCWMCN-JQNWNMCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]butanoic acid
• Synonyms: Amyloid β-Protein Fragment 10-20

Database IDs

• CAS Number: 152286-31-2
• MDL Number: MFCD00467025
• PubChem SID: 162226446
• PubChem CID: 71308529

CALCULATED PROPERTIES

• Acid pKa: 3.28947
• H Acceptors: 20
• H Donor: 18
• LogD (pH = 5.5): -6.8482027
• LogD (pH = 7.4): -5.5292554
• Log P: -5.570772
• Molar Refractivity: 375.6812 cm^3
• Polarizability: 147.11847 Å^3
• Polar Surface Area: 538.32 Å^2
• Rotatable Bonds: 45
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.1% TFA: soluble1 mg/mL
• Apperance: lyophilized 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

• Compostion: Protein content, ≥70%

DETAILS

Sigma Aldrich - A6825

Amino Acid Sequence
Tyr-Glu-Val-His-His-GlnLys-Leu-Val-Phe-Phe
Biochem/physiol Actions
Amyloid β protein fragment containing the α-secretase processing site (Lys16-Leu17 bond). It also contains the HHQK domain (residues 13-16) responsible for binding to microglial cells. This fragment is also a substrate for matrix metalloproteinase-2 (MMP-2 or gelatinase A).