3-[2-(2-amino-5-carbamimidamidopentanamido)-3-phenylpropanamido]-3-[(1-carboxy-2-hydroxyethyl)carbamoyl]propanoic acid

• ChemBase ID: 103849
• Molecular Formular: C22H33N7O8
• Molecular Mass: 523.53952
• Monoisotopic Mass: 523.23906105
• SMILES: NC(CCCNC(=N)N)C(=O)NC(Cc1ccccc1)C(=O)NC(CC(=O)O)C(=O)NC(CO)C(=O)O
• Canonical SMILES: OCC(C(=O)O)NC(=O)C(NC(=O)C(NC(=O)C(CCCNC(=N)N)N)Cc1ccccc1)CC(=O)O
• InChI: InChI=1S/C22H33N7O8/c23-13(7-4-8-26-22(24)25)18(33)27-14(9-12-5-2-1-3-6-12)19(34)28-15(10-17(31)32)20(35)29-16(11-30)21(36)37/h1-3,5-6,13-16,30H,4,7-11,23H2,(H,27,33)(H,28,34)(H,29,35)(H,31,32)(H,36,37)(H4,24,25,26)
• InChIKey: SAGYNNXCQOFQHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(2-amino-5-carbamimidamidopentanamido)-3-phenylpropanamido]-3-[(1-carboxy-2-hydroxyethyl)carbamoyl]propanoic acid
• IUPAC Traditional name: 3-[2-(2-amino-5-carbamimidamidopentanamido)-3-phenylpropanamido]-3-[(1-carboxy-2-hydroxyethyl)carbamoyl]propanoic acid
• Synonyms: ARG-PHE-ASP-SER; Arg-Phe-Asp-Ser

Database IDs

• CAS Number: 102567-19-1
• MDL Number: MFCD00076457
• PubChem SID: 24890475; 162090961
• PubChem CID: 5236782

CALCULATED PROPERTIES

• Acid pKa: -0.75627905
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): -7.0396466
• LogD (pH = 7.4): -7.177486
• Log P: -7.040786
• Molar Refractivity: 138.0134 cm^3
• Polarizability: 49.854553 Å^3
• Polar Surface Area: 270.05 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: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C22H33N7O8

DETAILS

Sigma Aldrich - A1675

Biochem/physiol Actions
Blocks integrin-binding and nonbinding of fibronectin fragments
Other Notes
Peptide analog of Arg-Gly-Asp-Ser

REFERENCES

• Auffray, C. and Novotny, J., Human Immunol., 15: 381, (1986).