(2S)-5-carbamimidamido-2-{[(1S)-1-carboxyethyl]amino}pentanoic acid

• ChemBase ID: 159658
• Molecular Formular: C9H18N4O4
• Molecular Mass: 246.26362
• Monoisotopic Mass: 246.13280508
• SMILES: NC(=N)NCCC[C@H](N[C@@H](C)C(=O)O)C(=O)O
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)O)N[C@H](C(=O)O)C
• InChI: InChI=1S/C9H18N4O4/c1-5(7(14)15)13-6(8(16)17)3-2-4-12-9(10)11/h5-6,13H,2-4H2,1H3,(H,14,15)(H,16,17)(H4,10,11,12)/t5-,6-/m0/s1
• InChIKey: IMXSCCDUAFEIOE-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-2-{[(1S)-1-carboxyethyl]amino}pentanoic acid
• IUPAC Traditional name: (2S)-5-carbamimidamido-2-{[(1S)-1-carboxyethyl]amino}pentanoic acid
• Synonyms: L-(+)-Allooctopine; N2-[(1S)-1-Carboxyethyl]-L-arginine; N2-(1-Carboxyethyl)-L-arginine; L-Allooctopine

Database IDs

• CAS Number: 63358-47-4
• PubChem SID: 162253793
• PubChem CID: 12313676

CALCULATED PROPERTIES

• Acid pKa: 2.675843
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.109854
• LogD (pH = 7.4): -5.1610627
• Log P: -5.1095414
• Molar Refractivity: 69.2762 cm^3
• Polarizability: 23.03181 Å^3
• Polar Surface Area: 148.53 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A546800

A competitive inhibitor of Octopine (O239850). Inhibits callus proliferation in apple.

REFERENCES

• Sagisaka, S. et al.: Biosci. Biotech. Bioch. 58, 978 (1994)
• Biellmann, J. et al.: Bioorg. Chem. 6, 89 (1977)