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

• ChemBase ID: 132190
• Molecular Formular: C9H18N4O4
• Molecular Mass: 246.26362
• Monoisotopic Mass: 246.13280508
• SMILES: C[C@H](C(=O)O)N[C@@H](CCCNC(=N)N)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+/m1/s1
• InChIKey: IMXSCCDUAFEIOE-RITPCOANSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 34522-32-2
• MDL Number: MFCD00078080
• PubChem SID: 162226467; 24898005
• PubChem CID: 108172

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: Off-White Solid
• Melting Point: 263-268°C; 283-284 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Toronto Research Chemicals - O239850

A nitrogenous compound from octopus muscles. It is used for producing seasoning and food additive.

REFERENCES

• Brown, A., et al.: J. Gen. Microbiol., 72, 589 (1972)
• Larher, F., et al.: Plant Physiol. Biochem., 41, 657 (1972)