(3S)-3-{2-[(2S)-2-amino-5-carbamimidamidopentanamido]acetamido}-3-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}propanoic acid

• ChemBase ID: 133247
• Molecular Formular: C15H27N7O8
• Molecular Mass: 433.41698
• Monoisotopic Mass: 433.19211086
• SMILES: C(C[C@@H](C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)O)N)CNC(=N)N
• Canonical SMILES: OC[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)N
• InChI: InChI=1S/C15H27N7O8/c16-7(2-1-3-19-15(17)18)12(27)20-5-10(24)21-8(4-11(25)26)13(28)22-9(6-23)14(29)30/h7-9,23H,1-6,16H2,(H,20,27)(H,21,24)(H,22,28)(H,25,26)(H,29,30)(H4,17,18,19)/t7-,8-,9-/m0/s1
• InChIKey: NNRFRJQMBSBXGO-CIUDSAMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{2-[(2S)-2-amino-5-carbamimidamidopentanamido]acetamido}-3-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-{2-[(2S)-2-amino-5-carbamimidamidopentanamido]acetamido}-3-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}propanoic acid
• Synonyms: Arg-Gly-Asp-Ser

Database IDs

• CAS Number: 91037-65-9
• MDL Number: MFCD00076452
• PubChem SID: 162227524; 24891220
• PubChem CID: 107775

CALCULATED PROPERTIES

• Acid pKa: -0.77673435
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): -9.26485
• LogD (pH = 7.4): -9.405291
• Log P: -9.266645
• Molar Refractivity: 108.9005 cm^3
• Polarizability: 38.612175 Å^3
• Polar Surface Area: 270.05 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 ... ITGA2B(3674), ITGB3(3690)mouse ... Itgb3(16416)

Product Information

• Purity: ≥95% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - A9041

Amino Acid Sequence
Arg-Gly-Asp-Ser
Biochem/physiol Actions
Tetrapeptide which supports fibroblast attachment and inhibits fibronectin binding to platelets. Target sequence for syphilis spirochete adherence.