1-{6-amino-2-[3-carboxy-2-(2-acetamido-3-hydroxypropanamido)propanamido]hexanoyl}pyrrolidine-2-carboxylic acid

• ChemBase ID: 134250
• Molecular Formular: C20H33N5O9
• Molecular Mass: 487.50412
• Monoisotopic Mass: 487.22782766
• SMILES: CC(=O)NC(CO)C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)O
• Canonical SMILES: NCCCCC(C(=O)N1CCCC1C(=O)O)NC(=O)C(NC(=O)C(NC(=O)C)CO)CC(=O)O
• InChI: InChI=1S/C20H33N5O9/c1-11(27)22-14(10-26)18(31)24-13(9-16(28)29)17(30)23-12(5-2-3-7-21)19(32)25-8-4-6-15(25)20(33)34/h12-15,26H,2-10,21H2,1H3,(H,22,27)(H,23,30)(H,24,31)(H,28,29)(H,33,34)
• InChIKey: HJDRXEQUFWLOGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{6-amino-2-[3-carboxy-2-(2-acetamido-3-hydroxypropanamido)propanamido]hexanoyl}pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: 1-{6-amino-2-[3-carboxy-2-(2-acetamido-3-hydroxypropanamido)propanamido]hexanoyl}pyrrolidine-2-carboxylic acid
• Synonyms: Acetyl-Ser-Asp-Lys-Pro

Database IDs

• CAS Number: 127103-11-1
• MDL Number: MFCD00076849
• PubChem SID: 162228527; 24891089
• PubChem CID: 4409396

CALCULATED PROPERTIES

• Acid pKa: 3.3448923
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -7.7256107
• LogD (pH = 7.4): -9.361124
• Log P: -6.527974
• Molar Refractivity: 114.4137 cm^3
• Polarizability: 45.206135 Å^3
• Polar Surface Area: 228.46 Å^2
• Rotatable Bonds: 14
• 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

Pharmacology Properties

• Gene Information: human ... GCG(2641)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - A6433

Amino Acid Sequence
Ac-Ser-Asp-Lys-Pro
Biochem/physiol Actions
Acetyl Ser-Asp-Lys-Pro is formed in bone marrow cells by enzymatic processing of thymosin β4. It inhibits the entry of pluripotent hemopoietic stem cells into S-phase of the cell cycle and protects against Ara-C lethality in mice. It is a specific substrate for the N-terminal active site of angiotensin converting enzyme, which is responsible for its degradation in vivo.