(2S)-2-amino-4-carbamimidamidobutanoic acid

• ChemBase ID: 175571
• Molecular Formular: C5H12N4O2
• Molecular Mass: 160.17438
• Monoisotopic Mass: 160.09602564
• SMILES: NC(=N)NCC[C@H](N)C(=O)O
• Canonical SMILES: NC(=N)NCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H12N4O2/c6-3(4(10)11)1-2-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
• InChIKey: IFPQOXNWLSRZKX-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-carbamimidamidobutanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-carbamimidamidobutanoic acid
• Synonyms: (2S)-2-Amino-4-[(aminoiminomethyl)amino]butanoic Acid; L-2-Amino-4-guanidinobutyric Acid; L-α-Amino-γ-guanidinobutyric Acid; L-Norarginine

Database IDs

• CAS Number: 14191-90-3
• PubChem SID: 164231481
• PubChem CID: 11389551

CALCULATED PROPERTIES

• Acid pKa: 2.305783
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -6.455877
• LogD (pH = 7.4): -4.9606295
• Log P: -3.6662374
• Molar Refractivity: 49.2785 cm^3
• Polarizability: 15.084841 Å^3
• Polar Surface Area: 125.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N661045

An Arginine (A769500) homolog. Used in the synthesis of derivatives and peptides of α-amino-β-guanidinopropionic acid and α-amino-γ-guanidinobutyric acid.

REFERENCES

• Rossiter, S., et al.: J. Med. Chem., 48, 4670 (2005)